Staying with Mrs Wentworth Day 1

This is my first story and it develops a little slowly.

Some people don't like that but I like a slow
development. I hope you do to. It is obviously meant
to be continued so if you have suggestions about
things, I'd be happy to hear them and maybe make
changes to make the story or characters better. I hope
you enjoy this situation.
I'm 18 years old and should be old enough to stay by
myself for a week when my single mom is off
somewhere. I don't know why she can't see that. I
heard my mom talking to her friend, an old teacher of
mine.
"Doris, I know he's 18 but I can't leave him alone. I
don't think he's prepared. He's sort of a young 18,
really. I really appreciate you taking him in while I go
away. I'll drop him off tomorrow afternoon on my
way to the airport."
I fought with my mom over this but she was always
over protective. I might not be the most experienced
guy and she didn't exactly encourage independence
but when a guy's 18, he doesn't want a babysitter,
right? But my mom insisted. "You'll stay with Mrs
Wentworth and I won't worry about you while I'm off
on my business trip. This is not open for discussion."
 Not that Doris was a babysitter. Mrs Doris
Wentworth was the old lady who had been my
teacher in fourth grade. There wasn't a Mr.
Wentworth. In fact, I don't know if there ever had
been. Maybe that's why she and my mom got along.
Neither had a husband. She was an old lady who was
always nice. Now I say old lady but really she just
seemed old when I was in fourth grade. That was nine
years ago and she was probably in her later 30s. She
was in her forties and actually looked pretty good for
her age. She was in good shape, dressed nice and was
always nice to me even when she tutored me in high
school. She might be kind of old, I thought, but she
was nice.
When Mom dropped me off, Mrs Wentworth lived
more than an hour away but on the way to the nearest
big airport. I took in a suitcase with some clothes and
Mom talked to Doris. Doris teased her about her trip
and told her to be a good girl and try not to get in
trouble. Then they both laughed in a way that made
me uncomfortable. I think they were probably talking
about sex or drinking. I knew my mom probably had
a sex life but I didn't think about it much. I did think
about sex itself a lot. I was 18 and as horny as any 18
year old you'd meet. I thought about sex day and
night. I didn't have much experience at all first hand
but it didn't stop me from having a fantasy life.
 Then mom got serious and gave me a kiss but it was
like when she was going out and I was 12. I was an
adult now and she didn't treat me like one. "Now,
Stephen, you be a good boy and listen to Mrs
Wentworth. While I'm gone, she's in charge of you. I
will be very angry if you're a bad boy. You listen to
her, help her out, do anything she tells you to, and
show her how nice and obedient you are. Make
mommy proud and be a nice young man." I felt like
she didn't notice I was a grown man. I was an adult
not 12.
"Aw, mom, c'mon. You're embarrassing me. I'll be
fine. I would have been fine at home and we're not
even near any of my friends...."
"Stephen!"
"All right, okay, I'll be fine. This will be fine.
Everything's fine. Don't worry. Have a good time."
Mom smiled. "That's better, but it's not to have a
good time, I'm just going because I have to go for
work"
Doris smirked and Mom gave her a dirty look.
But Mrs Wentworth put her arm around mine and
said "Don't worry, Stevie and I are old friends and
we'll be great. Run along or you'll miss your plane." I
didn't like being called "Stevie" but I liked her
attitude and we watched mom go.
 Then Mrs Wentworth told me to grab my suitcase
and led me up the stairs to my room for the week.
Following her, I realized she wasn't that old really and
actually had a nice ass at least how her skirt which
was a little tight cupped it. I kind of liked following
her even if it was weird to like looking at the
surprisingly tight ass of the "old" lady who was my
ex-teacher. We walked past a big bedroom which was
hers, really nice with a giant bed with posts and then
down the hall to the room for me. It wasn't exactly
masculine, like no sports pictures or anything
definitely manly but at least it wasn't pink or girly,
just kind of blue. I put my suitcase on the bed and she
told me she cleared out half the dresser for me. But it
isn't like I had a lot of clothes so I just put the suitcase
on the floor when she said "come down to the kitchen
when you're settled."
I walked out maybe 60 seconds behind her, pretty
much "settled." She smiled in the kitchen and had me
sit at the table while she gave me lunch.
While she cooked some soup and made a sandwich,
she talked about how nice it was to have me and how
it was like playing house. Then she laughed. I
laughed too but mostly I stared at her ass the whole
time. I liked it and I noticed every time she bent down
(and she bent down a whole lot of times, a lot more
than I hoped for) I could see the lines of her panties
bumping out. I liked that. When she gave me lunch,
she put a plate in front of me bent over and I noticed
from my angle her blouse wasn't real closed. I mean I
could see in and saw a pretty good look at a black
lace bra. I didn't expect that. I was surprised and tried
real hard not to react even though it made me hard.
She didn't notice me staring down her blouse and I
thought it was probably an accident. But we had a
nice late lunch and just talked about how things were
going with me. I hadn't started college and didn't
know what I wanted so we mostly talked about that.
Then she grabbed my hand across the table and held
it (which I liked) and said "now, sweetie, I hate to do
this and run off on you just as we've started our little
time together but I have to go out to a charity dinner
as a favor to a friend. I didn't know you were coming
yet when I made this date but I won't be late I
promise." Then she laughed at me, I guess I looked
funny. "Oh sweetheart," she patted my hand. "Are
you jealous? It's not a real date, I'm just going with
friends."
I don't know why she said that so I said "What? No,
of course not. What do you mean jealous? Oh you're
kidding. No, I don't care what you do. I'll just hang
out and do whatever." She smiled and said "that's a
good boy. I promise I won't be late. I'll be home by
9:00. You can hold me to that. I don't want to be
spanked for being bad so I won't be late." Then she
laughed again. "Now I have to go get ready so you
make yourself at home. Think of this as our house for
the week." And she went upstairs.
It was really weird. I didn't think I looked jealous.
That would be stupid. What do I care what some old
lady I'm staying with does? And what the hell did she
mean getting spanked? That was weird. Probably
some older person joke. It wasn't like I'd let her spank
me if I was late. And did she think I would bend her
over and spank that gorgeous ass of hers? Ridiculous.
I sat there thinking about it for ten minutes, though.
That was weird but thinking about it was at least a
little sexy.
I heard her up taking a shower so I guess she was
going to change to go out. I wandered around
downstairs realizing I couldn't call anyone and have
them come over or anything. We were way far away.
Not that I did a lot socially on a normal week but I
was feeling sorry for myself. I looked around the
backyard, couldn't see any neighbors or anything, just
a lot of land. I was turning on the TV when she came
down stairs and called out that she was going to go. I
turned and was speechless. She stood there smiling.
She was wearing a really red tight satin dress. It was
shiny and it hugged her. You could tell she had a nice
ass and I saw she had a nice figure everywhere too
and nice breasts. I couldn't believe I was noticing this
about a lady who was even older than my mom. But
she was very hot and the dress made her super hot. I
just stared and found myself wondering what was
under it and how come I never noticed how hot she
was. I mean maybe in fourth grade I sort of liked her
like a kid likes his teacher but wow! She asked me if
it looked OK? It did but I just nodded not able to
speak. "Oh, are you sure Stevie dear? You look
surprised. Is it the wrong style for an old lady? Do
you hate it?"
"Gosh no, Mrs Wentworth, it looks amazing and
you're not old or anything. You look awesome." She
smiled and said, "aren't you the sweetest little guy?"
Again I liked the attention but both she and my mom
had a way of making me feel 12. I mean what adult
18 year old wants to be called a sweet little guy?
I was kind of hard and horny because I was 18 and
always horny actually and I had just realized that
whatever else happened she was totally hot for a
woman her age. Hell, in that dress she was hot for
anyone. I didn't want to just sit on the couch and play
with myself so when she left I decided to explore. So
I walked around. It was a pretty big house. But very
orderly and not messy at all. There were a lot of
books but whatever I felt like doing, reading wasn't it.
I walked into her room. I felt kind of weird, sort of
forbidden like it was a private place I shouldn't be.
Which it probably was. She was very neat and
nothing out of place with her bed completely made. I
did open a drawer or two and even one with her
panties in them. I looked them like they were a basket
of jewels. And there were lots of colors and they
weren't boring. But I was afraid to touch because
everything was so neat.
So I wandered in the bathroom. This was a little
messier. But not a lot. A hairdryer was out and the tub
was wet still but it was a hell of lot cleaner than mine
at home. Then I saw the black bra I had stared at
earlier laying on the floor. I picked it up and stared
like it was magic. I have a total thing for women's
lingerie. It's so erotic and mysterious. It was very
feminine and it was black which made me hard.
Lingerie always turns me on so since I was alone I
actually unzipped and let out my cock. I didn't have
much real experience with women but I masturbated
lots of times.
I pulled the bra and back and forth across me to feel
it against my skin but was about to leave when I saw
the panties. They matched. I picked them up and
smelled them. I could smell a hint of perfume and her
on them. I tried not to but I grabbed them and started
jacking off even though I knew I shouldn't. In a few
minutes, more like 45 seconds, I grunted and shot a
load, catching it with the panties. Oops. I looked at
the pool of white cum caught in black silk panties. I
liked it and liked doing her panties like that but
afterward kind of thought maybe I shouldn't have
done that. So I wadded them up and found the dirty
clothes hamper and pushed them down under stuff. I
threw the bra in too and figured she wouldn't notice.
I knew I was a perv but I felt better because I came.
She wouldn't know and I'd be more relaxed. But
quickly I left her room after rinsing my dick off in her
sink. I went back downstairs and watched TV. I just
watched ESPN for a while to get my mind
somewhere else. I figured she'd actually be pretty late.
No way you go out looking like that and get home at
9. But I was wrong. I heard a car outside at 8:45 and
then the garage door and hear her come in. In the
family room, I was in a chair and hear her heels
making clicking noises slowly across the floor as she
walked through the kitchen and dining area and
finally came into the living room, leaning against the
doorway and looking just as awesome as when she
left.
I sat in a chair with my feet in front of me on a stool
and looked at her and just stared. I didn't say anything
for like a minute and then I just said, "uh, hi." She
was standing there leaning against the doorway with
one hip out. Her legs looked awesome between the
heels and some white stockings. I hadn't notice every
detail before she left but wow she looked like some
fantasy woman in shiny satin. It was only a couple
hours since I had used her panties to get off but I was
instantly really hard in my pants.
She looked at the clock and said "not even 9 yet and
I'm home, that was the rule and I followed the rules.
It's good to the follow the rules isn't it Stevie?" Then
she walked into the room slowly and stood at the edge
of the chair looking down on me, smiling, and
making me a little self-conscious. "Um, yeah, I like
rules. Of course. So did you have...."
But she interrupted and told me to sit up, reaching
down and tapping the bulge I wasn't hiding. "Sit up
and cross your legs sweetie-pie. You need to be more
discreet about some things."
I turned super red and sat up and crossed my legs to
hide myself. I was more embarrassed than I'd ever
been but I didn't know what to say. "I'm sorry," I
mumbled.
She sat on the stool I had just been using and patted
my hand again. It made me feel little. "Don't be sad
my little sweetie. Mrs Wentworth is just trying to
teach you like I always do. You were always a good
little student and I know you'll be a good boy if
someone just shows you what to do. I know you'll be
a good for me won't you? Are you my good little
student, sweetie?" She smiled at me and I nodded.
But she kept looking. "Say it Stevie dear. Tell me"
I wasn't sure what was going on but I said what I
thought she wanted. "Yes. Sorry. Yes, ma'am. I'm
your good little student." She smiled.
I looked down kind of embarrassed. She was turned
with her legs crossed so I just stared at her legs. I
watched them from her heels and all the way up
noticing that her legs the way they were pointed
sideways made her skirt high. I could see all the way
up her thigh and to some white lace band at the top of
a stocking. She didn't notice how much she was
showing I guess. It made me harder to see it and to
know that it was an accident but I kept my bulge
hidden.
She smiled, half stood, leaned over and kissed my
forehead. Then she stood and said "OK, now it's
bedtime. We have a busy day tomorrow." As she
walked away, she stopped and looked at me and it
was clear she meant bedtime for me too. It wasn't
even 10:00 yet. But I followed her. She walked
slowly which I enjoyed from behind. She took the
steps real slow I guess because she was still wearing
heels which she really should have taken off to climb
the stairs but I loved it. I'm surprised I didn't cum in
my shorts.
 She went into her room and stopped me before I
could keep going. "Stevie, dear, remember about
helping me like mommy said...."
"Uh ok, sure." What now? I thought. And I wish she
didnt say "mommy" like I was some kid.
She stood in front of the dresser looking in the
mirror and said to me "Mrs Wentworth can't reach her
dress's zipper. Be a good little dear and help unzip
me. I'm sure you help your mommy that way too."
That seemed really really weird to me but I wanted
to be helpful so I reached and carefully pulled the
zipper down. I realized that I could see some skin and
her bra straps from the back and I was going a little
lower. But then she dropped something I think
because she suddenly bent over and down to the floor.
I lost my grip on the zipper and her backside pushed
out so that her beautiful satin covered ass pushed
back into me and against my rock hard bulge. Just for
a minute and then she stood back up. I finished
unzipping a few more inches down. But I could see
the top of red panties and also what I figured out was
a white garter belt. I had only read about those and
never seen them in person but it was hot. It was funny
that her bra and her panties were both red like the
dress even though no one was going to see them.
Well, almost nobody because I saw the back of them
at least. It was a lot more erotic to me than it would
have sounded.
She turned around, her dress still up but loose, and
kissed me very softly near my ear. "Thank you for
being my good little helper, now run off and put on
your jammies and get into bed." I was confused. It
was sort of seductive and sort of belittling. And it's
not like I wore "jammies" like some kid. I wore shorts
and a T shirt and I got into bed. A lot of nights I jerk
off thinking of someone my age named Julie but
tonight Julie was replaced by Mrs Wentworth. It was
weird but I came pretty fast and fell asleep and slept
great wondering what tomorrow would be like.
Staying with Mrs Wentworth Day 2
This is the second part of staying with Mrs
Wentworth. A lot of people gave me great feedback
and made suggestions I tried to use including more
details on the clothes which I tried to look into more,
doing some research and using some suggestions.
Thanks to all of them for making this better than it
would without the advice. I can see keeping going
with this story but I'm also trying to think of new
ideas for new stories too so if you have suggestions
like that I'd love to have them. Hope you enjoy. Just a
reminder, this is a kind of slow story more than a
quick action thing.
The next morning I woke up pretty early from the
sun coming in the window and just from being in a
strange place. I'd almost forgotten that my mom
forced me to go stay with her friend Mrs Wentworth
while she was gone on a trip for her work. Mrs
Wentworth was a teacher of mine a long time ago but
now that I was 18, almost 19 actually, I thought of
myself as an adult and found it pretty insulting to stay
with some old lady friend of mom's. OK, maybe she
wasn't completely an old lady. She wasn't really old,
maybe in her forties. And she seems mostly cool so
far and it isn't like I had anything else going on so I
shouldn't complain. Plus it turned out she was
actually pretty hot for her age. Actually for any age. I
tried to be subtle about it though. I wasn't going to
run around just staring at her.
Anyway, I woke up and she poked her head in the
spare room I was sleeping in. "Hey, sleepyhead, come
on down for breakfast as quick as you can."
I'm always hungry in the morning so you didn't have
to ask me twice. I got up. No reason to get dressed for
the day yet so I went downstairs in my shorts and T
shirt. She was busy getting stuff together and just said
over her shoulder, "have a seat, Stevie dear. I've got
some food for you." I liked that she was real friendly
but "Stevie dear" always seemed kind of belittling.
Not that she meant it that way and I didn't really mind
it that much.
I watched her because, well, why wouldn't I? She
wasn't dressed completely yet either. I'm not saying
she was undressed but she still in her pajamas. At
least, I assumed she had on her pajamas or nightgown
or something but all I could see was a satiny bathrobe
which came down to her knees but not over them. It
was a light purple in color and had lace cuffs on the
sleeves. It wasn't revealing or anything but it was real
elegant and more formal if a bathrobe can be that
way. It was also tied pretty tight so it didn't hide her
figure but showed it off.
 In fact, it showed it off real well. While she was
talking she was bending down and doing something
on the floor or in the cupboard I think. Anyway, when
she bent it cupped her ass real nice. I figured out the
night before what a fantastic butt she had and this was
really showing it off for me. It was an accident but I
enjoyed it since it happened three or four times. I was
almost disappointed when she brought me a glass of
orange juice and put down a plate of eggs for me. I
smiled and said thank you. I also looked at her and
even though she wasn't giving me a look down her
robe, the tightness reminded of how nice the top half
of her shape was too.
I think I might eat too fast because I ate the eggs
and three bacon pieces in about two minutes. The
orange juice didn't make it long either. So I got up
and took my plate out to the sink and tried not to stare
at Mrs Wentworth anymore. I didn't try real hard not
to stare but at least I wasn't obvious about it. She
finished messing with the coffee machine and
stretched as she turned around. I have to say that I
don't mind when a woman wearing a tight satin robe
arches her back and stretches. I might have stared
then but who wouldn't?
I'm not used to being around people in the morning I
guess because I didn't think about things. Suddenly,
she looked real seriously at me. "Stevie, honey, we
need to teach you a few things." Then she grabbed the
big tent in my shorts. My hardon was sticking up and
real obvious. I didn't know what was going on though
because I don't really get a lot of women grabbing me
by my hardon like it was a handle. It's not like she
was making a move or anything (of course). Instead
she was humiliating me just a little bit. She said, "I
understand how you young men are but little Stevie
here needs to behave in front of company so I want
you to take him upstairs and put on a pair of
underpants to keep him under control." Then she let
go of me and slapped me on the ass to push me along.
"Now hurry up so you can wait on me."
I was totally humiliated. I mean it was cool that she
touched me even through my shorts but it was
humiliating the way it happened. It was exciting
though. So I hurried up, threw on a pair of tighty
whities under everything and came back down. She
looked carefully at my crotch as I came into the
kitchen. Like she was examining me. I was sort of
aroused by being examined so carefully but really it
was more like a walk of shame. But then she smiled
and said "now be a good boy and bring me a bagel
and cream cheese and coffee. I'll take my breakfast on
the deck."I guess I looked surprised so she said,
"remember what your mommy said about behaving
like a good boy. Now, get to it." And she smiled and
went to the deck.
It annoyed me for some reason when she talked
about "what mommy said" like I cared what my
mother said. And I never called her mommy. But she
was right. I did want to be cooperative. Not because
my mom wanted me to but because I liked Mrs
Wentworth. I kind of wanted to take care of her After
all, she made me breakfast so I would repay the favor.
She had a bagel out on the counter so I just toasted it
and got a tub of cream cheese out of the fridge and
spread it on a plate. Simple. The coffee was in the
coffee maker already dripping. I was about to ask her
if she wanted a big mug or what when I saw she put
out a whole tray with pot and creamer and cups and
stuff. There was sugar in the bowl so I put some
cream in the creamer and poured the coffee into the
china pot. I put the plate on the tray and carried the
whole thing out like a waiter. I was actually pretty
proud of how I was taking care of her. Then I put it
down on the little table by her and said "your
breakfast, Mrs Wentworth." Like I was a waiter.
She smiled and had me pour her a cup with cream
and one sugar while she ate part of the bagel. I sat
down too and she told me to have coffee. I don't
really drink it but it seemed very polite so I did it. I
had a cup the same way and sipped it. I liked it a little
but what I liked more was looking at her legs the way
they came out of her bathrobe. She was laying back
on a chair with her legs spread out and crossed at the
ankles. Nice legs. Awesome legs. I think I like them
better in stockings but whatever. Her legs were great
anyway you looked. I guess I never thought about it
before but I was definitely a leg man.
After a few minutes, she reached her hand out to pat
my hand and said "thank you for being a good waiter.
I think the week is off to a good start." I was going to
say "it would be if you wear that awesome dress from
last night everyday" but of course I didn't. I just
enjoyed sitting there with her appreciating me and
staring at me a little bit.
The she let go of my hand and sat up a little bit. She
said "Stevie, dear, I want to ask you something." She
looked at me and said, "are you a virgin?"
I almost freaked. I mean who the hell just asks that?
Especially someone I hardly know. I almost got up
and walked out. I was angry, mostly angry, maybe a
little embarrassed. Like I'm going to talk about this
with some lady who used to be my teacher. "No.
What? I mean of course not. Why would you think
that? Why are we even talking about this? I'm not,
you know, I get around and all that."
She smiled but didn't laugh. "Stevie, don't be mad or
embarrassed. You know sweetie that you can tell Mrs
Wentworth anything and it will be just between us."
She smiled but I didn't say anything, I was almost
unable to talk. She patted my hand again and said,
"But you haven't actually had intercourse have you?
Mrs Wentworth knows these things." I didn't say
anything and I was just red and pissed. I mean I'd
done stuff, maybe not a lot of stuff and maybe she
was technically right but why were talking about it? It
was like she could hear my thoughts though. "It's
okay, darling. I don't think boys should have sex
when they are 15 or 16 or 17. I think it's good to wait
you turn 18. It's important to wait and we wouldn't
even be talking if you weren't an adult."
"I'm almost 19 actually and whatever I do or not is
because I decide to and want to and I don't need
anyone's permission. I don't know what my mom put
you up to but I'm my own man."
Then she patted my hand again. "Of course, my
sweet Stevie. Of course. You know your mommy and
I didn't even talk about this. I would never want to get
you in trouble with your mommy. But I know you
trust Mrs Wentworth and I know I can help. Wasn't I
a good teacher all those years ago and you learned to
read? You know you can trust Mrs Wentworth don't
you, honey?" She looked eager and
I couldn't really be mad so I just shrugged.
Actually I kind of did trust her anyway.
 She smiled and looked real happy. "Oh goodie. I
know this would work out! Mrs Wentworth will help
you be comfortable with women. I know. I know you
are but I'll help some more. Just little things. Nothing
too personal or intimate of course. How about you
and Mrs Wentworth have a nice little date tonight?"
She looked at me again and I didn't say no or run off
anyway.
"That's the spirit. That's my good boy. And we won't
even tell mommy about it. Now, we'll go somewhere
nice and have a nice dinner. That's all we'll do but it
will be fun, won't it? Of course it will. Did you bring
some nice clothes for your special date with me?"
I didn't know what to say and I had to humor her
anyway so I just went along and thought I might get a
few tips on small talk at dinner and stuff like that.
"But I only have like shorts and stuff so maybe
somewhere kind of casual."
She frowned and said, "No, no. That won't do. I
know. We will go to your mommy's house. It's only
an hour and you can pick up a suit or whatever you
have. I'll change and we can eat at a nice restaurant
near there. I don't get over that way much since I
stopped teaching. We'll have a long drive home to our
house but that's fine. No, it's settled. We'll leave in a
little while."
 We skipped lunch so we'd be hungry, she said. Then
she packed a small bag so she didn't have to be
completely ready for all day and we left.
Mrs Wentworth had a nice car, a Mercedes, and she
let me drive so already she was getting more
awesome in my book. When we got into my town,
she wanted coffee so we stopped at a Starbucks. I
ordered hers and I got a mocha drink for me because I
only like coffee a little. While I got the drinks, she
went to the ladies room and I ran into a girl I knew in
high school. Julie was hot mostly and I liked to dream
about her but she was not exactly super friendly. I
guess she was actually kind of rude to me most of the
time. She asked me what I was doing there like she
owned the place and laughed when I said I was just
getting a drink and I had a date later. I guess I was
trying to sound important but she was just being
bitchy. Something she was good at. "Sure you do
Steve. You going to take your hand out to dinner and
show it a good time? I'm working tonight so if your
hand gets hungry bring it to Anthony's." And then she
laughed and walked out.
I suddenly noticed Mrs Wentworth behind me and
she was watching Julie leave. "Stevie, honey, what's
the bitch's name? Is she always like that?" She looked
kind of angry too.
 I told her not to worry. Some people just like to
tease. We let it go and went to the house. Anyway, we
went to my room. I really only have one suit (and
even that I never wear almost ever). My mom likes it
and it's basic gray with a red tie. She says it goes with
anything. Mrs Wentworth said "it'll do. Let me do a
few things about reservations. I decided I want Italian
and maybe we'll go to Anthony's tonight."
I thought I didn't want to see Julie. But then again
maybe I did if I had Mrs Wentworth with me. Maybe.
But probably I just hoped we didn't see anyone.
Anyway, she left my room and got ready in my
mom's room and I got ready. I checked myself out in
the mirror. I don't know fashion exactly but I think I
looked good. I was like a banker or a CEO. I probably
looked ten years older. At least I thought so. I sat in
the living room downstairs waiting for Mrs
Wentworth because she took a little longer than me.
When she came downstairs, I can hardly describe it
but I could see why she took a lot longer than me. Let
me try to describe it. She almost floated down the
steps, not wearing shoes yet but she paused to put on
her high heels. Putting on heels while standing up
really forces the guy watching with his jaw open to
stare at your legs and try not to drool. The shoes were
great too. I think I really like high heels. Hers had
long pointy heels. The heels were black not metal or
anything and the shoe wasn't shiny it was dull, like it
was fabric not leather. The toe area was covered by a
sort of wrapped fabric, not quite a bow but gathered
together, and it left the toes open to show a little. I
saw because she waved her feet at me after she put
them on and asked "do you like new shoes, Stevie,
darling? I bought these special for you." I knew she
hadn't because it wasn't like we stopped at the store
but that's OK.
I smiled and nodded. She was great looking and
when she got closer I just said "holy shit!" She looked
mad but a fake mad and said "now, now, you watch
that mouth darling. Don't be a naughty boy!" And
then she laughed and told me to go outside. "You
need to knock on the door and pick me up silly."
So I went out and knocked and said "good evening,
may I escort you to dinner?" She liked me getting in
the spirit as we walked out to the car. She was
holding my arm and said "walk slow for your date,
sweetheart. Stop trying to look down my blouse. A
woman appreciates subtlety." I was going to say I
wasn't trying to look but I was. She gave me pointers
though. "Stephen, instead, let your arm drift to my
waist. There, hold me lightly and don't go too low to
be obscene. Are you ready for a secret?"
I stopped walking not sure what she meant. She said
"Move your fingers a little and tell me what you feel."
 "Uh, nothing really, just a skirt I think."
"Silly Stevie. No, dear, feel there? That's the top of
my panties. Feel the strap along here?" She moved
my hand. "That's a garter. They're not comfortable or
practical so if your date is wearing them she probably
went all out to dress up for you. Now pretend to be
subtle like I didn't notice anything and just help me
into the car."
I opened her door and she smiled as I helped her
into her seat. Her dress wasn't short exactly. It was
very expensive looking. It didn't have sleeves and it
was a little low in front but not too low to show off a
lot. The top was very form fitting which works when
you have an upper body like Mrs Wentworth but
makes it hard not to stare. The skirt had lacey stuff
over the top of an almost shiny black material. Like I
said it wasn't high but when she got into the car, it
went up a lot and I saw her legs almost completely up
her thigh including lace at the top of her stockings.
But I didn't see all the way up.
She adjusted like showing me so much leg was an
accident. Maybe. I drove to the restaurant and we
parked. Immediately, she ran off to the bathroom
while I went and got the table. She made the
reservation under Stephen so I felt good. But while I
was talking to the hostess getting ready to sit, that
Julie came by. I really was hoping to avoid her and
she was even more bitchy if that was possible. She
gave me a real bad time about being alone and about
what kind of person goes out to eat by himself.
Finally, the hostess glared at her and told her to stop.
She was about to go do her job when Mrs Wentworth
suddenly swept into the area all energetic and asked
loudly "did you get a nice private table honey?' She
took me by the shoulders and whispered, "don't ask
just put your hand on my ass and squeeze it right
now." I was shocked but did as I was told (and why
the hell not!) and she kissed me. Not softly either. She
grabbed and pulled me and kissed me long and hard
the most erotic kiss I ever had even without any
tongue.
The she let go and turned like it was something she
did everyday. My hand fell off her gorgeous ass and
she smiled at Julie as if she was our servant. "We'll
need a private table if you can." Julie was
dumbfounded (which was awesome!) and just said
"uh, do I know you?" Before I could explain, Mrs
Wentworth just said "I'm sure we don't. I'm Lana.
Stephen's lover." Then the hostess took us, glared
again at Julie and led us to a table. The whole time
I'm all casual and trying to look like this is just the
way I am on the outside but inside I'm screaming
"what just happened? Did she really have me grope
her and that kiss was incredible. And why did she say
I was her lover? Lover? And since when did she
become Lana, I thought she was Doris Wentworth?"
Julie wasn't our waitress but she would look over
when she could and Mrs Wentworth got real close to
me. We were in a corner booth type table so she could
slide pretty close. I was about to explode when
"Lana" leaned over like we were whispering like
lovers do. But she said, "now don't panic, Stevie dear.
I had to do that. Your little friend is a bitch and I
wasn't about to stand by and let her treat you like she
tried to do. We watch out for each other don't we,
darling? And it wasn't so awfully terrible to be kissed
by Mrs Wentworth was it, sweetie?" Then she giggled
I smiled and felt more at ease and so grateful for her
caring enough to hate Julie. She was right. Julie was a
bitch. But I had to ask, "I mean, wow, it was hot. I
mean you're hot. It was amazing. But who's Lana? I
don't understand."
She playfully grabbed my knee and said "oh, I never
come into this area anymore but it's possible she was
a student a long time ago. So to be careful I decided I
want her to think I'm your somewhat older girlfriend
not your old teacher. I think it worked. Did you see
how she looked when I kissed you and when I said I
was your lover." I laughed but to be honest I didn't
look at anyone else or notice anything.
 I know Julie was staring at us the whole time we
were eating and I didn't care. Finally she found a way
to come over to our table even though she wasn't our
waitress. I could tell Mrs Wentworth was pissed
though. Her eyes looked very very angry. Julie
ignored her and tried to start talking to me. So Mrs
Wentworth leaned over and started licking the side of
my face. She whispered in my ear "trust me and act
calm and natural."
I was distrated by her tongue in my ear but almost
immediately, she reached down and unzipped me and
reached in and pulled out my cock. I was still
perpetually hard from earlier and I knew Julie
couldn't actually see but she knew. For some reason it
made Julie really mad. I didn't know what to do until
I felt Mrs Wentworth not just stroking me but start to
massage my balls and whisper "let it go, don't hold
back." I tried not to be completely obvious but I came
into her hand and she stopped sucking on my ear.
She smiled at Julie, wiped her hand with the napkin
below the table and then handed it to Julie. "Run
along and take care of this for us." and with that Julie
was dismissed and speechless. Mrs Wentworth
suggested we leave without dessert and quietly
slipped me cash under the table to pay for the meal. I
was speechless and just zipped up before the waitress
came back.
 As we were leaving, Julie came over not quite able
to be bitchy anymore but still looking curious and a
little dazed. "Aren't you guys having dessert?" she
asked. Mrs W was totally into the Lana character
when she leaned over and whispered but not too
softly "I need something sweet with a nice gooey
cream filling so Stephen is going to fulfill me which
he's so good at." Julie completely froze. We walked
out, got in the car and drove off. It was incredible!
I was feeling awesome as I drove. "Stevie, honey,
head back to our house, no need to go back to your
mommy's place." She looked into my eyes while I
was driving and looked worried. She didn't say
anything for a long time and I felt weird. I wasn't sure
if I should say something or apologize or what she
expected. Then she reached over and grabbed my
hand and squeezed it.
"Stevie, darling. I feel terrible. That shouldn't have
happened. I didn't mean for anything to happen. Are
you mad at me?"
I just stared at her. But I was driving so I couldn't
stare long. And I said, "Mad? Why would I be mad?
hat was awesome. I mean Julie was totally put in her
place and you were amazing. I didn't know that
anything, well, you know, in public and all."
She looked sad suddenly and I guessed I said the
wrong thing. "Oh, Stephen, dear sweet, Stephen. I
knew I shouldn't have done that but that silly little
bitch got to me. Sweetheart, please understand that
was just protecting my Stevie dear. I know it was
wrong of me to let you squeeze my ass tonight, and
you know it too? It was probably naughty of us and
we just did it to teach that little bitch a lesson. I don't
want you to get the wrong idea about Mrs Wentworth,
sweetie-pie." She didn't mention making me cum in a
napkin but I was guessing it wasn't the time to bring it
up.
"No, Stevie. I must apologize to you. It was wrong
of me to get carried away. Mrs Wentworth was a
naughty girl and broke the rules. And after I warned
you the other day. I feel terrible. I apologize
completely for teaching wrong and setting bad
example." And then she looked sad like she thought
I'd really be mad.
Talk about hot then cold. My head was almost
spinning so I didn't know what was going on. But I
guess I always knew it was not a real thing so I said,
"Yeah, no, sure of course. I know it was just a thing
we were doing. Like roleplaying or something, right?
A play or something like a trick. I didn't get the
wrong idea at all. No, you weren't naughty or
anything. Don't even think about it." Not that I
wouldn't be remebering it for a real long time but I
really sensed she wanted me to say what I said.
 She squeezed my thigh and said "I knew you
understood. Such a smart young man. Roleplaying is
exactly what it is like. Roleplaying." She paused
before continuing and looked thoughtful. "Oh, and of
course as part of your lesson you know that on a first
date you would never kiss that intensely in public or
grab a woman's ass in front of other people that way. I
haven't forgotten that I'm teaching you still. But it
doesn't change that I was naughty. Terrible." She
smiled though and it wasn't long before we got back
to her house or our house as she kept saying.
When I got out, she stayed in the car until I realized
I was supposed to open her door first. So I opened her
door like the gentleman I am (I was wearing a suit
after all) and let her out. I was very polite and tried to
be subtle as she wasn't careful with her dress and I got
a huge look at her thighs. I walked her to the door and
she stopped and said very formally "thank you for a
lovely evening, sir." I'm thinking I get the game now
and say "my pleasure, Ma'am" Then she leans in and
kisses me. It was a lot softer and maybe less erotic
than the restaurant but it was slow and soft with wet
lips. In some ways it was even better than the one
inside the restaurant.
The she giggled and said "lesson over" and grabbed
me and we went inside. The date was over.
 "Honey, be a dear and get me a glass of wine.
There's an open bottle in the fridge." Now we were
just people hanging out. Me visiting Mrs Wentworth
and waiting on her a little bit. She went and spread
out on the couch and waited for me to bring the bottle
and a glass. I poured her a glass and then went and sat
down and loosened my tie. She drank the one glass
pretty fast though and then stood up and said, "well, I
guess we should get this over with."
I have to confess I had no idea what she was talking
about. She stood in front of me and said, "Stephen, I
was a naughty girl and I am truly sorry and want to
formally apologize to you. I know what I did was
wrong and this is only what I deserve." Then she
pointed to a different chair and told me to sit in it. I
was confused. Very confused actually. So I said,
"what's going on?"
She looked at me like I was dense and said "my
spanking obviously."
I didn't see that coming. I had no idea what to say
but I just moved slowly and waited. I nodded my
head as if to say, "oh yeah, that." But inside I thought
"what the hell, does she really think, how strange is
this?"
She started to bend down and then thought for a
second and said "I can't ruin this dress that way." So
before I knew what was happening (not that I would
have tried to stop her), she reached behind her and
unzipped and took off her dress, folding it neatly on a
chair. I stared. Maybe I was subtle in my stare but
probably not. I was just going along at this point. She
stood there in some really pretty underwear. Her
stockings that I had seen most of were black and they
hooked by garters to a black garter belt. I think
garters and garter belts and stockings were my new
all-time favorite clothes. her bra and panties were
mostly black with some white silk on them too. I
think the black was sort of sheer and over the white.
But whan a gorgous woman in her underwear stands
in front of you ready to be spanked, the world moves
in slow motion.
She looked real sorry at me and then got down and
bent over my lap. The panties were mostly black in
back when they covered her ass. If I thought she had a
beautiful ass when I was following her up the stars,
this was even better. I was harder then I'd been the
whole time and that's saying something. The front of
her panties pressed against my leg, My hardon was in
an OK spot but when she squirmed, it pressed her
stomach a little. Her breasts were over the other leg
and she turned her head to look up and say, "I'm
ready to be punished Stephen."
I wasn't sure exactly how hard to spank so I
smacked down on her ass once a little hard but not
real hard. I liked the way it felt when I sort of slapped
her beautiful butt. She gave and I heard her say
"OWW" or maybe more like"ohhh." Like she was
surprised and squirmed to get comfortable. I probably
should have told her to stop squirming but I didn't
mind. I smacked her three more times each time
getting a slightly slower "Ohhhhh." I was going to
stop but she didn't move or get up at all. She was
breathing heavy too. So I smacked a little more. Not
harder and I might have let me hand rest for a minute
between smacks.
After about twelve smacks, her "Ohhhs" were very
long and coming from in her throat so I knew she
wasn't really hurt. She also wiggled a lot between
smacks. But after twelve, she got up quickly, very out
of breath and said quickly "Thank you, Stevi, I
deserved that. I'm going up. Say goodnight when you
walk by my room." and she ran quickly up the stars.
I sat there for a long time. I wasn't sure what
happened. But I wasn't complaining. After fifteen
minutes, I went up to bed myself. her door was open
so I looked in to say goodnight. She was already in
bed under the sheets and blanket. I didn't know what
to say so I just said "Ok, good night Mrs Wentworth."
She smiled and said "thank you for coming to say
good night, sweetie. I had a very nice date tonight
with a nice gentleman." I smiled and said thanks. I
wasn't sure what else to say.
"Stephen, honey, when someone is naughty that
person is punished and everything is forgotten. It's
erased and we never think of it again. Now do Mrs
Wentworth a favor and take her clothes and put them
in the hamper inside the bathroom over there." I
looked and found her underwear all in a heap right
next to the bed so I picked them and walked them to
the bathroom. I paused and thought a little when I
noticed how wet her panties were. The ones that were
in a pile on the floor of her otherwise spotless room.
Out of sight, I took a secret sniff of them before
throwing them in the hamper.
I walked about of the bathroom and said good night.
She said "night night sweetie, go put your jammies
on." Then as I was closing the door, she stopped me.
"No, no, honey. At our house, we don't close the door
on each other. My door is always open for you
because I told you that you can trust Mrs Wentworth.
My open door and your open door and symbols of
that." Then she blew me a kiss and I went into my
room and slept. I'm pretty sure I had the best dreams
I've ever had and it was only my second night there.
Staying with Mrs Wentworth Day 3
This is part three of the scenario. I'm enjoying
crafting Mrs Wentworth and I hope you do too. The
story and its development are very slow. I should say
I have benefitted from a lot of advice from
commenters even if the story doesn't always go
exactly like some suggestions. This is my first story
and it's a learning process. I hope you enjoy.
The sun woke me up again and it took me a few
seconds to remember where I was. I remembered that
my mom had forced me to go stay with her friend
Mrs Wentworth while she was gone for a week. I
resented it. I was almost 19 and old enough to live on
my own if I wanted but I humored my mom. Mrs
Wentworth was my teacher in fifth grade and that
made it more humiliating. I should be on my own not
staying with some old lady who used to teach me.
Actually, she wasn't that old really. A lot older than
me but probably around 40. And she turned out to be
very nice. I wouldn't admit it to my mom of course
but I didn't mind staying with Mrs Wentworth. I was
starting to like it really.
As the sleepiness wore off, I remembered the events
of the night before (see Day Two). I started thinking
about everything but mostly about Mrs Wentworth
taking off her dress and laying over my lap in her
very nice lingerie and having me spank her for
supposedly being naughty. I started thinking and
doing what I usually do in the morning which is
jerking off. I slipped off my shorts and used them
while I stroked to keep from making a mess. I was
living in my head the night before and not really
noticing anything else so it wasn't very long before I
came and emptied myself. I sopped it up with my
shorts and was catching my breath when I thought I
saw some movement by the door.
I forgot about Mrs Wentworth's open door policy.
Her door was always open symbolically she said so
our doors shouldn't be closed to each other. Maybe
she walked by or something. I hadn't noticed anyone
but then again I was in another place so would I have
noticed if anyone watched? I bet she'd have said
something if she saw me there doing my thing. A few
seconds later though, I heard her call out "Stevie,
honey, are you up?" I had only a split second to toss
the sticky shorts on the floor next to the bed and pull
up the covers to cover myself.
She came in with an arm full of laundry looking
rested and energetic. "Hi, sweetie. I'm just doing a
load of necessities so I thought I'd grab a few things
from you. Let's see." She looked around and I said I
was okay but she grabbed a shirt and shorts from the
chair and put them in her arm pile and then before I
could think of anything to say she bent over and
grabbed my fresh shorts off the floor. Her hand must
have squished and felt the pretty big load I had
sopped up. But she just squeezed it in her hand,
looked at me, smiled and kept a tight grip on the
shorts. Then she said "come down when you're ready,
dear."
I waited until I heard her going down then I got up,
took a quick shower and got ready. When I got
downstairs, she had breakfast going and was pouring
me a cup of coffee. "There's a bagel in the toaster if
you want it, I just finished and am enjoying my
coffee." So I got my bagel, sat down and put stuff in
my coffee and started sipping it. It wasn't great
because I still was not really used to coffee but it
made me feel sophisticated.
I was chewing a bagel when I noticed her looking at
me. "Stevie, honey, I know you're a virgin right now
but have you experienced other things like oral
pleasures?" My mouth was full so I couldn't yell at
her and say, "what the hell are you talking about?"
But I thought when she was pushing the whole virgin
thing yesterday, my reaction meant it wouldn't come
up again. But here she was with a total invasion of
privacy. When I finally finished chewing, I said "why
are we talking about this? You don't know me and
what I do and stuff like that. I do lots of things with
lots of people but, you know, it's private. I mean
c'mon!"
I was steamed but also puzzled. I mean this woman
was like a completely different person from one
minute to the next. In the morning she was one way
and at night another and I never knew what was
coming my way. Plus I didn't really like talking too
much about how many things I had done or not done.
She reached over and smiled, though, not offended at
all. She patted my hand and said, "It's okay honey. I
don't want to embarrass you. I am just trying to help. I
know that right now, as of today, you haven't had
intercourse with a real woman yet and that's fine. It's
a good thing actually. I just didn't know how far along
you were. I'm sure a nice gentleman like you doesn't
like to kiss and tell and you shouldn't. But sometimes
a teacher likes to know her students. Remember
you're my pupil, honey, and Mrs Wentworth can help.
It's okay though. A lot of boys haven't tasted a woman
yet." She smiled in a very reassuring way and I didn't
have to reply. I even stopped turning red.
Fortunately, she stood up and walked over to the
sink so I didn't have to feel awkward. I stared after
her thinking of what to say but instead found myself
just staring at her ass pressing against another silk
robe as she bent down at the sink. I took my dishes
over and was trying to walk around when she backed
up without seeing me and her tight silky butt made
direct contact with my bulge. She said "oops" and
giggled but managed to collide two more times as we
tried to get our signals right.
Finally, she walked away and headed upstairs. She
called down "I'll be ready to go in ten minutes."
What? Go where? I didn't know what she meant. She
was going out I guess. But I was wrong. It wasn't just
her.
She came down, dressed like a very nice lawyer or
something in a blue business suit which fitted her
tightly and whose skirt was over her knee but not
much over. She looked great. Not as good as the silk
dress but I guess in the daytime you can't go all out. I
was admiring her when she opened the door to the
garage and said "I'll drive today. Let's go."
I was going to ask where but I thought she told me
before and I forgot or something because she didn't
say. She talked about other things. "Stevie, darling,
I'm having the girls over for a late lunch or early
dinner." I must have looked surprised because she
said, "Oh I didn't mention it did I? Three of my
closest friends are coming over for tea and light meal
late this afternoon. I don't have anyone to help serve
so I thought you could be the waiter. I'll train you of
course but it will be fun. Like having a butler." I
didn't have any response but I thought, what the hell
it's better than mowing the lawn or doing something
else. I said, "oh yeah, okay."
We pulled into the parking lot behind a store and
got out. I followed her in. It was big store but sort of
private. Mostly clothes but no prices or signs of cash
registers or anything. A tall woman, even taller in
heels, with pulled back dark hair came over and
kissed Mrs Wentworth on both cheeks. "Good
morning, Mrs Wentworth, we're so happy to see you
again. Lisa has the items you ordered." The woman
almost completely ignored me. Her assistant Lisa
came over with three stacked boxes tied together.
Lisa was younger than the owner ( at least I think she
was the owner, she never talked to me so I wasn't
sure). She was much shorter and wearing a short
dress. She smiled and even winked at me. Mrs
Wentworth thanked her and said "I need a few things
for Stephen here. We're having company and I think
some shorts or something to hold everything would
be a good idea." The owner said, "well, Lisa can help
get one of the things we have in stock but we're
shorthanded today Mrs Wentworth so you'll have to
help with the sizing." I had no idea what was going
on or anything so I didn't even talk. I wasn't sure why
I needed shorts but Mrs Wentworth was doing this
without having talked to me first.
 Mrs Wentworth looked uncomfortable and like she
was going to protest but she didn't. Lisa smiled at me
again and the owner took my shoulders and pushed
me in front of a chair like the stools you try on shoes
with. I went to sit but Lisa pushed Mrs Wentworth
into it instead of me and whispered "go ahead." The
owner measured my waist and said "30" to Lisa and
then waited while she looked at Mrs Wentworth.
Mrs Wentworth looked at me and said "Now,
Stephen, dear, this is fine. It's just a measurement. It
is all very clinical." The way she looked, it was like
she was trying to reassure herself more than talking to
me. Then she undid my belt and pulled my shorts to
me ankles and looked at the owner nervously. I
couldn't speak and had no idea what was happening.
The owner looked at Mrs Wentworth with just a hint
of a smile and said "not good enough. They are fitted
and we need a better sizing or they won't hold right.
Take it out."
Mrs Wentworth then pulled my underwear down
and held my cock in her hand like she had before. I
started to get hard right away remembering things.
The owner whispered to me while looking at Mrs
Wentworth "let's see if you get larger, Stephen, while
your teacher helps out. I need to find out if it's bigger
than average or average or small when you're as big
as you get. Now don't get him too excited Mrs W. I
don't want a mess just a size." It was humiliating and
also very exciting. Mrs Wentworth was stroking me
and had her spare hand massaging my balls
underneath which had me pretty close to exploding.
She was very serious while she was doing it and
staring very hard at my cock as it throbbed so close to
her face except that she would look up at me every
minute or so which made me very close to cumming
right there. Then the owner handed a ruler to Mrs
Wentworth who had to let go of my balls and press
the ruler against me for a few seconds and say
"seven." The owner laughed, which made me feel
bad, and called out "seven, Lisa." Then she smirked
and said to Mrs Wentworth "you're a natural at that."
Then she said to me "according to research the
average male penis is 5.5 - 6 inches erect so
congratulations." She was a little condescending so I
was embarrassed but happy to learn I was bigger than
average.
Lisa came back with tight shorts that were almost
like biking pants. Then she explained to Mrs
Wentworth not to me that "when he wears them he
needs to hang it on the right side. See, it's looser there
but just a little. It will hold him but not cut anything
off." They handed them to me and I put them on.
Tight everywhere but there was a little looseness for
my now semi-hard cock to be tucked into. I didn't
know what to say so I just got dressed. Lisa handed
Mrs Wentworth two more boxes "for the waiter." I
took the two boxes and her three and we went to the
car without paying anyone.
In the car, I tried to talk not knowing what to say but
Mrs Wentworth interrupted. "Stevie, sweetie-pie, you
know how we talked about making sure little Stevie
doesn't surprise people? This is going to help us. I go
see Mrs Jones for a lot of things. She has quite a nice
collection so I knew she could fix this. I bet you feel
much better with little Stevie in a proper spot, don't
you?" With that, she reached over and patted my leg
right there. The whole thing seemed weird so I just
said "Yes, Mrs Wentworth. Thank you for thinking of
it."
She pulled in the driveway and said, "Back at our
house. Now we need to get ready for our little lunch
party." We went inside and she started right away
showing me what to do. How to answer the door and
act very official. How to show a lady into the dining
room. How to serve plates and a pot of tea. We
worked hard for a couple hours then she talked to me
more about having the right attitude.
While we talked, she had me follow her and we
went into a laundry room where a bunch of clothes
had been drying on air drying racks since before
breakfast I think. The first thing I saw was my
underwear that she had picked up earlier sitting there,
now washed and dry. Almost everything else was her
clothes. Actually mostly underwear. She picked up a
few blouses and folded them while we talked. Then
she told me to "be a dear and help me get these things
folded. We don't want all our undies out when we
have our guests at our house do we? I'm sure your
mommy makes you clean up too when friends are
coming over."
I started folding things but I wasn't sure where to
start. The things hanging closest to me seemed to be
only her panties and the other places had more
underwear. I started folding her panties because I
knew how to fold them anyway unlike some other
kinds of underwear. It was interesting because they
were all different colors but they were all silk or lace
or things like that. I folded slow because I kept
holding them too long. I tried to pay attention to what
she was saying but when I was folding a pair of black
lace-all-over panties I was distracted. It was the first
time I was glad I had the new underwear because it
made sure I wasn't just pointing up and out but was
held together.
Mrs Wentworth didn't seem to mind. She seemed
really happy actually. I didn't ask if she only had sexy
underwear but I did wonder. I mean my mom had
some things but most of what I saw in the laundry
anyway was cotton and regular. Maybe Mrs
Wentworth was just a lot sexier. I was pretty sure I
remembered seeing other things in her room when I
was snooping but maybe she washed them separately
or something.
She put the laundry in a basket and told me to leave
it on her bed. She then took out one of my boxes and
put it on top and told me to wear my uniform and get
ready quickly, guests would be here any minute. I
went up and changed. I was a little nervous at first
about what might be in the box but it was just a nice
white shirt, tight even though I'm pretty skinny. And
also a pair of black pants. You know, like a waiter.
The pants were dressy but a little tight in the legs and
much tighter on my ass than I wear anything. But
that's the way uniforms are.
I heard a car in the driveway as I came down the
stairs. Mrs Wentworth looked out of the kitchen and I
saw she had changed again. Gone was the cool
sensual lawyer. Now she was wearing a flowery dress
that came down halfway to her ankle and was
buttoned up on top pretty high with maybe a little
neck exposed. She looked less like a lawyer and more
like a schoolteacher. It was very different, I thought,
from the red satin tight dress that I dreamed of the
first night I stayed over.
 She went back in the kitchen and let me get the door
as soon as the doorbell rang. I opened the door on
three women. They all looked different but also all
looked sort of like Mrs Wentworth the way she was
dressed now. They were surprised to see me, I think. I
said "good afternoon, ladies. Mrs Wentworth is
expecting you. Would you care to follow me and I'll
lead you to the dining room." I was so good I could
have played a butler in a movie or something. I turned
and walked and they followed, whispering to
themselves.
I held the chair for the first one and let her sit before
following and doing the same for each in turn. Then I
carefully unfolded each napkin and placed it on their
laps. I knew my actions perfectly just like I was
shown. The ladies were almost speechless when Mrs
Wentworth breezed into the room. She walked around
and kissed each on the cheek but they were all
obviously old friends.
She nodded at me and said "please bring in lunch
now, Stephen." That was my cue to serve the food.
They giggled when I left and I heard one say, "Doris,
did you buy him or are you just renting him for the
day?" Then Mrs Wentworth's voice, "Janine, please,
he's a former student and the son of a friend." Then
another voice saying, "I'd like to teach him a few
things" followed by a nervous giggle and the person
named Janine saying "can I have my lunch off his
cute butt?" And Mrs Wentworth more authoritatively,
"stop it, he'll hear you and get the wrong idea. Stop it
now."
I came back into the room with two platters with
small sandwiches and cold salads to help themselves
to. As I leaned and placed them in the center of the
table, I felt a finger poke my ass like it was testing its
firmness. The lady next to me was smiling. It turned
out she was Janine. With her other hand she was
gently touching the skin under her neck and above her
cleavage. She wasn't low cut but lower than Mrs
Wentworth and had a teasing smile. I didn't say
anything but I went quickly back to where I left a
teapot and started pouring for everyone like I had
been taught. Mrs Wentworth was beaming with
approval, Janine was looking hungry and directly at
me. Another woman, a brunette, just looked nervous
but happy. She was the one that giggled and was a
little shorter and about fifty, dressed more
businesslike but it didn't come off quite as sexy as
Mrs Wentworth had done it earlier.
The fourth twirled a string of pearls in her fingers as
I poured. She had dark hair, a silk blouse and just
stared at me without speaking. Janine on the other
hand was talkative. When I poured for her last, she
kept finding reasons to touch my arm or bump me.
"Stephen, is it?" I nodded. "Stephen, I'm not your
grandmother. I'm going to need more than a cup of
tea. I notice the wine glass you set out for us. Are you
pouring wine soon? Janine's day out needs more than
tea." Her grin was like a predator surveying birds to
eat. The other ladies all smiled or giggled. I guess
Janine was known for being the bold one of their
group. Mrs Wentworth interrupted and said "You
may serve the wine that's chilling in the fridge. The
bottle on the left please." So I went to get it too.
In the few seconds I was gone, I could hear the
giggler tell Janine "you're saucy today, Janine!" and
Janine respond "and we just got started."
Everyone had wine except the giggler who said
something about driving. I had started with Janine but
by the time I got around she was almost empty and
holding out for more. Mrs Wentworth suggested I
place the second bottle from the fridge on the side
table and then join them. I sat with Janine on one side
and the giggling woman on the other. They talked a
little. I guess they all went to school together in the
past but soon the quieter third woman named Anita
asked about me. "Stephen, Doris tells us you're a
student of hers." Mrs Wentworth corrected "former
student from my last year in the last school I taught
at. Now he's just staying here while his mommy is
away." I just looked at her and thought it was a weird
way to say that. The giggler, Kim, asked in a half
whisper if I had a girlfriend and giggled. I was trying
to sound more sophisticated so I just said "not a
specific one right now, you know how it is." At the
same time, I felt someone's foot rubbing my leg and
Mrs Wentworth said "oh but he had a date with a
pretty girl last night, didn't you dear?" I didn't know
where she was going with this and wasn't sure how to
respond. I mean the pretty girl was her and obviously
she knew that.
While I was deciding what to say, she quickled
added, "Her name was Lana I think you said, wasn't
it?" I nodded, feeling better about it. "Yes, Lana it
was and she was very nice. I had a great time." With
that, I smiled at Mrs Wentworth who blushed even
though no one else noticed or would have understood.
Then I felt Janine's hand on my thigh when she leaned
over and asked suggestively "did you get lucky,
Stephen?" I didn't know how to respond when Mrs
Wentworth interrupted almost angrily "Of course not,
Janine, stop that. Stephen isn't going to kiss and tell.
He's a very sweet boy and knows better than that."
Then, almost like she was changing the subject, she
said, "Stephen can we start the other bottle?" The
ladies had finished the first bottle of wine and I
started pouring another while Janine said "you always
were a prude, Doris." But she laughed and so did the
others so it wasn't mean-spirited.
Janine rubbed my ass while I poured and reached
over and squeezed my thigh again when I sat back
down. Mrs Wentworth looked annoyed at Janine and
then got nervous when Anita asked if Lana and I were
serious. I said, truthfully, "It was our first date, really
so it's hard to say."
Mrs Wentworth becamse more at ease and said to
Anita "but they made a very cute couple so I hope
they go out again." I smiled and thought about what
that meant.
The second bottle was soon gone even though only
three of them were drinking it and Mrs Wentworth
sent me for a third which she had also put in the
fridge. I was surprised because it seemed like a lot of
wine but maybe she was expecting to drink that
much.
Janine didn't know I could hear everything when I
was in the kitchen and I heard her ask Mrs Wentworth
the minute I left, "Doris, he's adorable. Can I take him
upstairs and fuck him in your bed?" Kim giggled,
Anita said "I don't think your husband would
approve," and Mrs Wentworth said "you're such a
bitch, Janine." But then they all laughed.
Of course it made me hard as a rock. I was
contained but my bulge while not poking out was
outlined by shorts and I realized the waiter pants
weren't loose enough and so they showed it off
instead of hiding it. I realized this when Kim was
staring at my leg while I was serving Mrs Wentworth
and kept staring. Janine touched my ass again while I
was serving and then told me she thought Kim
wanted more tea. While I gave it to her, she didn't
giggle but just stared.
Mrs Wentworth didn't seem to notice her one friend
touching me and the other less bold one staring
openly at my bulge. I sort of resented that the pants
and shorts that Mrs Wentworth decided on actually
showed me off like that. But I guess she didn't think
about that and she didn't seem to notice anyway. We
stayed there talking for a while. Mrs Wentworth and
Janine had most of the third bottle. In fact, Mrs
Wentworth had a lot, Janine not quite as much and
Anita very little.
When they finally left it was getting dark. I held the
door. Kim gave me a hug and Janine accidentally
pushed her into me so my bulge pressed into her. She
giggled and left. Anita also hugged me but more
normally. Janine grabbed both of my ass cheeks,
pulled me close and kissed me passionately before
whispering "I wish I could take you home. I could
teach you a lot more than your old teacher could."
Then she walked past and slapped my ass, leaving me
staring.
Mrs Wentworth came back in after seeing them off
and I followed her into the other room where she
turned around and said "Stephen, my darling, you
were just wonderful. I was so proud of you and so
grateful!" And then she put both arms around me and
hugged me very tight. I was so surprised and actually
very happy to have helped that I didn't pay any
attention to how I was positioned and where my bulge
was. I was still pretty hard from Janine's good bye but
Mrs Wentworth didn't seem to notice it pressing into
her. At least that's my guess because of how long the
hug lasted.
She pulled me next to her on the couch. Then said
"wait a minute." And got up and brought back a new
bottle of wine and two clean glasses and poured us
each a glass. I don't usually have any but it made me
feel pretty sophisticated to be sharing with her. She'd
had a lot of the first three bottles so she was maybe a
little bit drunk. Not stupid drunk like your friends in
college might get but happy.
She stretched out her legs on the coffee table and
then tuned and said "help me off with my heels you
helpful man." I helped take both of them off. I think
women's high heels are rel sexy so I kind of enjoyed
it. Also I made her turn a little to get at them which is
actually a pretty good angle if you were trying to peek
up a very long skirt. I wasn't trying, at least not on
purpose, but since I could see I thought I would at
least look a little. Between seeing up her skirt and the
fact that the first foot I had let out of the shoe was
resting on the spot where my hardon and leg were
held tight together, I couldn't help staying pretty hard.
Then I noticed she was talking. I heard "...so I don't
usually wear this dress but with them I feel a need to
keep up a look. After all, Janine is the one who...well
it doesn't matter. Does the dress look OK, Stephen, or
is it boring?" She stood up and stared at me.
I decided to be honest. "It looks fine. You look
good, I mean. It is a little boring though but it isn't
like you could wear that red dress you wore the other
night here, right?" She playfully kicked me, still
standing up. "I thought so. I knew you liked that
dress. Oh well, help me change now." I must have
looked funny because she said "it's OK, silly boy. I'm
sure you help your mommy all the time dressing and
changing and finding things. I just need that kind of
help now. After all, you've been so very helpful to me
and my friends today."
Then she turned around and held up her hair. I
helped lower the zipper on her dress because that's
what she wanted obviously. With her back to me, she
wiggled her arms out and it fell first to her waist and
then to the floor. She stepped out of it with her back
to me still. She was wearing a white bra and her
panties were visible through sheer pantyhose. She
bent down to pick up the dress at her legs causing
once again her ass to collide with me. I wasn't
complaining though. Then she walked away and
started going up the stairs and asked "are you
coming?" I didn't know what was going on again but I
followed.
In her room, she started going through the closet
and drawers like she was looking for something. I just
stayed in the doorway and enjoyed the view. After a
few minutes she bent down with her back to me and
took down her pantyhose and took them off and
laughed a little like we were sharing a joke. I was
confused of course but maybe her being a little bit
drunk explained everything.
But I wondered what was next. It wasn't that late
and the dinner was more like a late lunch but it was
after 7:00. It wasn't bedtime but she was looking at
pajamas and nightgowns. She had me hold a few
short satin nightgowns and robes while she looked.
Then she took the black lace pair of panties I liked
out of the laundry basket that was still on her bed and
set them down. Turning to me, she looked up and
down like she was evaluating me. "Hmmm, I think
we'll watch a movie before bed or something so I
should probably be careful. I think shorts and a top
are the right thing. OK set the pile on the bed." I
turned to go but she called out "Wait!"
She reached out and held both my hands and looked
at me. "Darling, You look so much like a waiter and I
just know that our guests appreciated your service and
how perfect you looked." And then she hugged me
again. This time her beautiful body just in her
underwear pressing warm and tight against me. It's
amazing I didn't explode. But I might have throbbed a
little.
After a few seconds she looked concerned and
pulled back and stared at my leg. Then she touched
the lump in my pants. "Oh dear, he's been cooped up
all day hidden away nice and proper so no one notices
him. That's fine but I'm sure you shouldn't wear the
shorts all day. Why don't you change too?" Then she
patted my bulge and sent me along. It was weirdly
erotic but at the same time in a manner that wasn't
exactly seducing. It was a weird combination of
motherly or something like that and also sort of bold
because she touched what obviously hard even
though not in a date kind of way.
I almost closed her door but she wagged her finger
and said "open doors, always."
It felt good to let everything hang out. I liked being
held in but my cock and balls needed some breathing
space. I just changed into some loose shorts and
boxers and a not tight shirt and went downstairs. She
had gone first and was sitting on the couch with two
glasses of wine again and a tray with crackers and
cheese. I noticed she was wearing green shorts and a
matching long top that almost hid the shorts.
The whole thing seemed really very elegant and
sophisticated and grown up. That was really nice. It
was like she knew we were adults, equals sort of. And
she was treating me just like it. I sat down where she
patted a spot on the short couch. I liked the way she
looked. The pajamas were sexy in a way even though
they were shorts not a skirt and I couldn't look up
them. Not that I spend my life trying to look up skirts.
I'm not a total pervert all the time. But they were nice.
Green satin was sexy and we were close on the couch
like old friends.
I could kind of tell from the way her upper body
was that she wasn't wearing a bra under her nightshirt
because even though she was in good shape there was
a sagging sometimes in her upper body that made it
clear her breasts weren't held up. I did notice once
when I got up and was about to sit down that her legs
were stretched out on the coffee table and propped up.
She was less careful I guess because she was wearing
shorts so I could see the loose patch of satin that went
between her legs not completely covering the layer
underneath. That's how I could tell she had the black
lace panties I had folded and looked at on underneath
everything. The first time I noticed, it made me pretty
hard. I managed to stay pretty hard for a long time
because she kept doing things like reaching across
and touching me on the leg when something was
funny in the movie or turning and smiling and I
would see almost a little cleavage. Or she would stand
up to reach across the table for the wine bottle or
other things and the way she bent made her gorgeous
ass very noticeable and just a few inches from me. I
wanted to reach out and grab it but of course I didn't.
Because the whole time was like a sort of long tease
and I was just sitting there enjoying it, I didn't pay
much attention to the movie. It was an old movie.
Black and white with people I didn't know and I'm
glad there wasn't a test because I wasn't watching the
TV at all. At one point I completely stopped looking
at the TV because I noticed something. Mrs
Wentworth's pajama shirt was long but it was a little
tight in the chest. I could see bumps that told me she
had hard nipples. Maybe because it was cold a little
or I was hoping it was from just being with me or
something like that.
A few minutes later, there was a commercial in the
movie and she stood up and told me, "You know, my
nightshirt is long enough that I don't have to have
these shorts on. I think I'd be more comfortable
without them." And she carefully removed them in a
way I couldn't see anything. She was correct that
when standing up her shirt covered her panties. But it
wasn't by much and when she sat I saw a lot of leg
because we weren't very far apart. Then she asked me
to go get the remaining little bit of wine in the kitchen
that was almost empty even though her glass was
pretty full. When I came back, she still wasn't careful
how she sat, forgetting she took her shorts off I guess,
and I could see a lot. I tried hard not to stare but I saw
all her panties and they were almost completely in the
open. You have no idea how hard that made me. I
almost wished I wasn't just wearing loose shorts with
just boxers under them because I was really exposed.
I sat back down and continued staring at Mrs
Wentworth's breasts while she watched the TV. I
couldn't exactly cover up myself but as long as she
looked at the TV, I was OK. She stood up again and
bent over causing her shirt to rise in back and expose
the panties. They had a black lace back almost like
netting. They looked better tightly covering her ass
than when I folded them. If this was a movie I'd have
jacked off and cum in about 10 seconds. But I tried to
stay cool. She sat down again but closer. Our legs
almost touched and she smiled at me and drank more
wine. I'd had about one full glass but she had had over
the last five hours a whole bunch more.
She looked directly at the pressing bulge in my
pants and sighed and patted it. "Oh, my sweet
Stephen, I feel so bad. The whole day must have been
hard for you with that awful Janine just teasing you
and you're still under pressure from it now! I feel
terrible. You need some room. Now don't worry,
sweetheart. Mrs Wentworth understands how men
and their parts work. Stand up and take off your
shorts so you aren't pressed so much. Don't be shy.
We're alone in our house and it's perfectly fine and
natural. Right now, please."
What could I say? I sort of agreed. And I couldn't
protest so I stood up and did it while she leaned
forward a little like she was watching and almost
staring. When I dropped the shorts, I only had on
boxers and my cock was poking straight out.
Dropping the shorts almost made it bounce.
Fortunately, it was away from the fly opening so I
didn't spring out. Mrs Wentworth reached a finger out
and poked the tip which was hidden but made a wet
spot with pre-cum. "Oh, look. Poor thing is actually
leaking. I'm glad we let him have some room." Then
she leaned back and watched the movie.
Talk about mixed signals. Oh well, I sat back down,
more comfortable even though I was sitting next to
this older woman with a practically throbbing hardon
almost visible. I was sure it would calm down with
fewer peeks at her and a slower evening. It started to
go down a lot pretty soon and she never looked
directly at it. But when she stood again and bent, the
tease of her panties was too much. It was worse when
she twisted as she sat. Her shirt rose more than she
probably thought and it was twisted so it was tight
enough on her breast and facing me that I almost had
to stare. And then she leaned and put her head against
me like she was tired. I had to close my eyes for a
second not to explode.
She was sort of whispering with her head against
my neck, "it's terrible what they did to you and made
you so frustrated all day long. I'm glad I was a perfect
lady at dinner and didn't contribute to that!" I couldn't
tell her that it wasn't just her friend at dinner but it
more her and her awesome look all day that did this
so I didn't say anything.
Then she looked down and poked my hard on and
giggled. She actually giggled. It was weird. "Hmmm.
It isn't healthy is it, darling? It's not good for a virile,
handsome, fit young man to be so frustrated and
backed up. And it was my friends so it's sort of my
fault." I just kept quiet because her hand went down
and reached in and pulled me out of my shorts. It was
all happening in slow motion like a dream. I mean her
hand actually had just pulled my throbbing cock out
of my shorts. Then her head moved down and
suddenly her tongue licked the tip and then I was in
her mouth. I was almost shocked.
I looked down and only saw the back of her head
but I could feel her warm and wet mouth all around it
until I felt her head pop off with a smacking noise.
"Yes," she whispered very roughly like she was
suddenly hoarse, "the only proper thing to do is
release the pressure." It was like she was talking to
herself though.
I'd love to say I lasted for like a half an hour. But I
didn't. This was the first time a woman, a real woman,
had even thought about sucking on me. It was
amazing and I had been so close to cumming off and
on all day. I didn't know at the time if she was good
or bad because it was my first blowjob ever but she
was actually really good. It was less than five minutes
before I was tense and started to spurt. Her hand
encouraged it all out even when she popped off.
When I was done, I sat there catching my breath but
she stayed there with her head down.
After a minute or two, I heard her say very quietly,
"I have to go to bed." The she stood up and turned
around and said "good night dear, thank you for all
your help today." It was as if nothing had happened
except she had a few spots on her nightshirt and
something on her chin. I didn't get a chance to say
anything, she just hurried away and up to bed.
After a few minutes, I got up and started cleaning up
things before going up. I was still in shock that it
happened. Mrs Wentworth had just given me a
blowjob. I had no idea what I was going to say to her
on the way to bed or in the morning.
It was about twenty minutes later when I went up. I
went to her room to say good night but she was under
her covers and obviously asleep so I just looked for a
minute and finally went on to my room. For the first
time there, I didn't masturbate before going to sleep. I
just tried to think of what to say in the morning and
how different everything was going to be tomorrow.
Mrs Wentworth At The Opera
This is actually the fourth part of the Staying with
Mrs Wentworth series. You might want to read the
day one through day three parts first. This is also
slow developing and maybe longer than it should be.
I'm really enjoying the characters so I got a little
long. I'm a new writer though so any feedback is
always appreciated.
I woke up later than I intended. It was the latest I
had slept at Mrs Wentworth's. I was starting to feel at
home in my bed in the spare room. I almost didn't
remember how mad I had been when my mom made
me stay there while she went away. I mean what 19
year old (almost 19) wants to be forced to be babysat
or watched over by some old lady who used to be his
fifth grade teacher? But I didn't mind anymore. After
all, Mrs Wentworth was really nice and actually kind
of hot for a woman her age. And actually her age
wasn't that old. She was maybe 40 which isn't exactly
old. And she treated me like an adult which after all I
was. Most of the time anyway.
Other mornings she had woken me up but today I
just slept through. It was already 9:30 and I was
looking forward to seeing her. Actually, I was curious
and nervous about what I would say but also looking
forward to it. After what had happened the night
before, I thought things were going to be really
different. I mean she actually pretty much gave me a
blowjob which changes things, doesn't it? (See the
story in Day Three of this series) I hadn't been super
sexually active in the past and it was probably
technically my first blowjob. So I didn't know the
next thing to do but I was sure we'd figure that out
together. I was pretty sure we were going to talk
about it and just go from there.
Anyway, I got ready and got dressed pretty fast to
get downstairs as soon as I could. However, on the
way past her room I stopped and saw her laying in her
bed. I went in and looked around not sure if I should
wake her. After all it was pretty late for her to still be
asleep. She woke me up at 6 the first morning and it
was almost 10 today. She was sleeping and her
clothes from last night were on the floor. The pajama
shorts and top she had been wearing, with the
addition of a few dried stains that gave me happy
memories, were laying there in a pile on the floor of
her usually really clean room.
I was thinking about whether she was naked under
the covers and how to find out when she woke up,
saw me and sat up in bed with a big smile. She wasn't
actually naked and had a blue nightgown on so I was
disappointed. I guess she had changed after
everything had happened last night. I smiled back and
tried to figure out what to say. I guess "thanks for
sucking on me" would have been a bad choice but I
wanted to say thanks. While I was trying to figure it
out, she saw the clock and said "10:00? Oh my
goodness! I never sleep this late. Oh my sweet Stevie
dear, you have to forgive me, I think Mrs Wentworth
made a big mistake last night."
I was a little shocked and said "well, I don't know
about that." But she shook her head and said "yes,
sweetheart, I set a bad example. I had much more
wine than I should have. I'm sure I didn't do anything
crazy because we didn't go out anywhere but I don't
remember a thing that happened after the girls left
and my head is aching. I'm sure I wasn't very good
company and I'm sorry."
I didn't know what to say. This was weird. Maybe it
all just happened because she was drunk. Wow, that
wasn't what I expected but I couldn't exactly remind
her of it. Instead I just said, "No everything was fine.
You know we saw a movie and we went to bed early.
I didn't even notice you were drunk. I don't mean that
you were drunk, just sleepy or whatever."
She smiled and said "How sweet. Always the
perfect gentleman. I'm so lucky to have found you.
Now be a good boy and run along so I can get dressed
and I'll make us some breakfast." So I went
downstairs and did some thinking. It was like she was
two different people sometimes and I was never
positive which one was going to come out. Still I
guess it was nice to be called a perfect gentleman.
Not that she "found me." My mom brought me over.
And while she did make me feel like an adult
sometimes, at other times her language was a little
funny. Be a good boy and run along isn't exactly what
some guy wants a super hot woman to say. Finally it
was weird that she didn't remember the most
memorable thing that had ever happened to me. Oh
well.
I was downstairs making a big pot of coffee because
I knew that coffee was a good thing after drinking.
That's what people said. When she came down, she
was really happy to see coffee and gave me a huge
hug and a big kiss before telling me "you're just the
sweetest thing taking care of me like that." It wasn't
sexy but it made me happy. She drank some coffee
and took a couple pills but seemed to recover pretty
fast while she was making us eggs and bacon. So I set
the table and she brought stuff over and we ate.
It was usually morning when she asked me
embarrassing questions so I jumped in first to avoid
them. "Um, Mrs Wentworth, are you on vacation or
do you have to go to work soon? I mean I hope you
aren't staying home because of me. After all, I'm an
adult and don't really even need supervision. I don't
want to be the one making you not go in."
She smiled again and leaned across and squeezed
my hand and told me "you're such a sweetie-pie to
think of that. Please don't worry, honey. I don't have a
job." I looked surprised and she quickly explained.
"Darling, I did teach for a few years but I think you
were in my very last class. The late Mr. Wentworth
didn't live very long but he did make a lot of money.
When he went, he didn't have any family, just little
old me. I finished out that school year and I haven't
needed to work since. I'm glad because it gives me so
much more time to spend with my dear, sweet
Stevie."
That explained a lot. I didn't ask how much exactly
she was worth but I guessed that her dead husband
had made a lot of money because she seemed pretty
loaded and had a big house and a real expensive car.
"Now, enough about that, Stevie. I have to ask
something important." That made me nervous.
"Sweetheart, I want to ask you to do something for
me, well with me really. A lot of men, I guess a lot of
people I should say, don't like to do it but I think you
should experience it and you might even like it. I
know I will like it and I think you will like it. In fact,
I'm pretty sure you will, a giving young man like you.
And I can walk you through it all because you won't
be familiar with doing it and obviously I am very
familiar. But it would make me happy if you and I
can do it together. That will be fun won't it?"
I was pretty sure I knew what she about to say and I
wanted to play it cool. So I waited while she
continued. "After our pretty little date at the
restaurant and how nice it was, I thought you might
be willing to try this. I know it will be fun for both of
us. I'm a little embarrassed to tell you but I've been
thinking about it and looking forward to showing you
since before you came here to our house."
She smiled at me and actually I had a huge erection
under the table. I was all set to crawl under the table
right there if she was ready. Maybe she wasn't really a
completely different person in the morning. I guess
she really did remember too and this was the next
step. It only seemed fair like the obvious thing after
last night. "Sure, I'd be happy to do anything for you,
Mrs Wentworth," I said. She was very surprised and
very excited I said yes. I can't believe I would ever
say no even if it wasn't something I had dreamed of
doing or tasting. It was partly a fantasy, obviously,
and partly an awesome sexual experience I had
thought a lot about in the past. I think I'd have done
anything for her right then. I knew I really liked her
even that quickly and I just got a kick out of seeing
her happy.
 She stood up and pulled me to my feet. Obviously
doing stuff under the kitchen table wasn't exactly
classy. It wasn't how a classy lady like her would start
her first time with me. She hugged me even though I
was pretty hard right then. I'm pretty sure she didn't
mind a huge tent in my shorts this morning because
we were actually talking about more advanced things.
Considering what we were about to do, it was fine to
be really worked up.
"Now I need to figure out what to wear. This is a
special occasion. And we need to decide what to put
you in too. I want us both to look just right." I never
thought a lot about clothes. At least my clothes. I
noticed everything she wore and all the details of her
underwear and her shoes and her dresses. I had spent
a lot of nights staring at catalogs and the real thing
was better. But I never thought what I wore mattered
a lot. But why not, right? I know I was definitely
extra turned on when she wore the right stuff so it
made sense that she might want me to wear
something special because we were talking about her
getting turned on. I was okay with that. I just didn't
know if she meant funky underwear or we were
talking costumes or something kinkier.
But whatever it was, I was up for it. "Mrs
Wentworth, whatever you want is okay with me.
Anything at all." She giggled and playfully swatted
me on the butt. "Careful what you say young man, ha
ha, I just might test you." And she laughed like she
told a joke. "Okay, darling, now obviously I'll dress
up from head to toe. I always do. For you, I don't
think we need a tuxedo. A lot of men wore business
suits last time I was at the opera so we'll work with
that."
I'm sure I looked really puzzled because she stared
at me and I mumbled "did you say opera?" She
looked and laughed and said "didn't I say that before?
That's so funny, Stevie. What did you think? You
didn't think I just meant some boring movie, did
you?" Well, I didn't tell her what I thought but I did
turn red and said "No I didn't really know. I mean I
wasn't completely sure. And, well, I've never been to
the opera."
She hooked our arms together and led me up the
stairs side by side up to her bedroom. "I won't waste
our time on silly movies. I really think you'll have fun
with me at the opera and I know we talked about how
you don't have a lot of experiences." We had talked
about that but usually she meant it in a sex way but I
guess not always. "And I know I'm your teacher right
now. I want to give you more experience so we can
have another fun date night. Maybe not exactly the
same as the last time though, right honey?"
 I said that I couldn't think about any part of the last
date I didn't like. She sat me on the edge of her bed
and smiled "Oh, I love that you're such a perfect
gentleman so you didn't mention that bitchy girl who
annoyed us. You're so right not to even think about
her, the obnoxious little tramp, or that part of that
night." I could feel Mrs Wentworth getting angry
again. It was cool that she got so angry when
someone was obnoxious toward me. Then she paused
and calmed down and went on with a smile, "We
were just two people having a nice meal and a quiet
evening together and coming home to our house. I
love that about you darling." With that she opened her
closet door and disappeared inside while I sat on the
bed.
I heard her making noises and opening and closing
drawers and humming. The she said, "where are you
sweetie? Come here." I walked just in the door. I
hadn't been in her closet before. It was big and had
lots of clothes hanging all over it and two pretty big
dressers in it too. And shoes everywhere.
But she was smiling at me and holding something in
her hand for me. It turned out to be two tickets. I don't
know exactly what I thought she was going to show
me. She read it out. It was La something at the Grand
Opera House. Italian, it turns out and it starred
someone named Sofia something who I guess I was
supposed to know. "Isn't it exciting, Stephen? I can't
imagine anything better for your first time and La
Belle Sofia is stunning. We're so lucky! I ordered the
tickets weeks ago."
She was so excited about it, it made me excited too.
I mean opera sounded like the last think I'd ever want
to do but she loved it so why not give it a try? And
she had the tickets for weeks. That was weird because
I don't think my mom even decided to bring me over
until a few days before I got there. But I guess Mrs
Wentworth was just glad now she had someone to use
that extra ticket.
She shooed me out and said "I'm not going to show
you my gown early. It will be a fun surprise and I'll
pick out the right things for you too. Now let's go
back down."
We walked downstairs and went in the living room
and she pulled out her phone while I crashed on a
chair nearby. "We almost forgot to call your mom to
check on her, Stevie hun. I'll talk first and then you
can say hello to your mommy." I hated it when she
talked that way but what can I do. The I guess Mom
answered and they started talking, "Hi sleepyhead, it's
me....Oh, we've been up for hours we probably got up
at 6 or 7...are you being a good girl....no Stephen's in
the other room, he can't hear us," and she made a face
and a shhhhh noise at me. So I tried to be quiet.
 "Yes, he's been a real sweetheart, very helpful....no
we haven't done much, mostly quiet nights. I had
some old friends for tea yesterday....of course he
wasn't in the way, he was very helpful....yes he was,
very. He was like a very skilled waiter....I'm sure he
might have been a little bored but he didn't show
it....maybe I'll take him to a movie one night...of
course and he helped drive me when I went shopping
yesterday too...yes, very boring but he took care of
the packages..he's a dear and if you aren't careful I
just might keep him....ha ha....how's is your
conference?" I noticed Mrs Wentworth said the word
conference with a little smile.
"Of course I know that, all business....yes, I'm sure
it's very grueling....conferences in Las Vegas are
always very difficult...I don't mean anything by
that...I hope you did manage to squeeze in some
fun.....oh that sounds nice, a lot of you?....oh did you?
That's interesting....Nothing at all, you're being
paranoid....oh i'll want to hear all the details
later....what? what was that noise?...I know I heard
something or maybe someone....I thought you were in
your room...Oh is that what it is? Well, I hope the air
conditioning wasn't banging like that all night...I'm
not implying anything but I know how these
conferences are....yes...oh well let me get him, he's in
the other room."
 She motioned to me to wait for a second or two then
handed me the phone. She said loudly "here Stevie,
it's your mommy, come say hi." I hated it when she
talked like that but I picked up the phone and said "hi,
mom, what's up?" Mom wasn't real talkative and
actually sounded out of breath a little. I guess she just
woke up. She said, "I'm fine honey. I want you to be
good for Doris." The she paused for a few seconds.
"Yes, please be very good. I don't want to hear about
any, oh wait a second." There was a short pause and it
sounded like she dropped the phone or something.
Then she said quickly, "I don't want to hear about any
trouble. Now be good and I'll see in a few days
probably. I have to go. Bye." And then it was over.
Something came up and mom signed off fast I guess.
Mrs Wentworth was frowning but didn't say
anything and didn't seem to want to talk about Mom.
That was fine with me. My mom annoyed me
sometimes. I said, "I guess it's going well." Mrs
Wentworth sighed and said "I'm sure your mom has
everything in hand. Enough about her though. We're
going to want to relax for a while, have a late lunch
and then get ready. It's a long drive and we need to be
there by 6 at the latest."
We ate and did some things around the house but it
was pretty early when Mrs Wentworth went up to get
ready and told me not to wait too long either. I had a
quick shower, shaved, and got ready. I wasn't sure
what to wear but I noticed she had laid clothes out on
my bed. All of it was very dressy and there was even
a pair of boxers. Not the new tight things she got me
before but they were new boxer briefs. I guess you
wear new underwear to the opera (joke). Anyway, it
was actually a new suit. My gray one was nice, I
thought, but this was a little dressier. It was dark
without a lot of pattern but there was just a little. The
tie was very bright with lots of purple but it looked
very sharp. I got dressed then I went downstairs. Of
course I was ready a long time before she was.
Finally, Mrs Wentworth came downstairs. Wow. I
mean, I admit I like loooking at a mature lady all
dressed up. In fact, I liked Mrs Wentworth in almost
anything but she was something else tonight. I
thought I looked sharp but she was amazing. The
dress had lace and sheer parts at the top but it wasn't
slutty at all. It was very fancy. The long flowing
bottom half was shiny and almost to the floor but you
could see it was cut a lot of the way up so she could
walk easier. Her legs showed when she walked
through the slit but it wasn't at all cheap looking. She
looked like a million bucks. I just stared.
She smiled as she came down, hair done, a lot of
makeup, a total knockout. "Good evening, sir, are you
my date for the opera this evening?"
 I said, "um, yeah." But then I caught myself and
bowed a little (I thought that was what I was
supposed to do) and said "Yes, I am, Mrs Wentworth.
Are you ready for an evening at the opera?"
She held her hand out and let me escort her to the
car. It was very formal but she seemed real happy
with it. I held the door and let her in the passanger
side. She wanted me to drive again which I was
happy to do because her car is awesome. While I let
her get in the seat and waited to close the door, I may
have noticed that her slit skirt sometimes showed off
more leg than she meant to. I didn't mean to stare but
I had to wait until she got in.
While I drove she reached over and patted my leg
and told me "you're a wonderful pupil and you're
learning very well to be a perfect gentleman. I just
know you'll love tonight's performance. Opera can be
so exciting." I admit I was expecting opera to be
terrible but I liked how happy she was and I wasn't
complaining about her patting my leg. I liked that part
even if her hand wasn't really near anything good.
It was a long drive and I couldn't really see her legs
in the car. She told me a lot about opera and what we
were going to see and why Italian was a romantic
language and perfect for opera and how very lucky I
was to get to hear this Sofia who wasn't Italian but
was born for the part. She was very excited so I tried
to be happy too but wasn't expecting to like it really.
She directed me to a valet parking downtown but
across the street from the Opera House. Opera houses
apparently don't have parking lots so you take what
you can get. This was connected by a walkway. We
got out. Mrs Wentworth said a few words, got a
ticket, gave it to me, and took my arm in hers and
walked me to an escalator, up and across and into the
Opera House lobby. Then she handed me the two
tickets subtly and I handed them to a usher who
bowed, smiled and directed us without words to a red
carpeted stairs.
It was actually pretty elegant and we walked up to a
bigger lobby with bars and lots of people, all of them
dressed as well as we were or better. Well not better
than Mrs Wentworth but some guys were dressier
than me. She told me to wait for a moment then she
walked to a bar and came back with two tall skinny
glasses with bubbling champagne. She handed me
one and said "Stephen, one always has champagne at
the opera." It was pretty cool.
She held my arm tight while we drank. I liked
champagne and we said a few words to people who
would walk by and smile. One oily guy in a white
bow tie came up and starting talking and eying Mrs
Wentworth too much. He was a weasel but older than
me by a lot and older than her by a lot too. When he
touched Mrs Wentworth's arm, I glared at him but he
didn't get the message. When he touched her arm
again, I thought it was a lot too much like putting a
move on her. I grabbed his arm and didn't let go.
When he looked at me, I just stared. I'm not a super
intimidating guy but with some oily opera guy I am.
He started to say something but just left.
Mrs Wentworth just kissed me on the cheek and
whispered "Stephen that was so sweet. I think you
were jealous." I didn't answer that but I did say "I
didn't like that guy or his attitude." She agreed
because she squeezed my arm and finished her
champagne then handed it to a hostess. Then she
pulled me toward the theater. The lights had flashed
which in opera land means we're about to start. We
got caught in a crush of people. Not a riot like thing
but still a lot of people trying to get through one spot.
Mrs Wentworth reached to grab my hand and when
doing it also pinched the butt right in front of me. The
lady in front of me didn't freak out but did turn her
head and look at me like I did it. I whispered to Mrs
Wentworth "what did you do that for?" But she
looked clueless and said "do what?" So I dropped it.
We got past the crowd and our seats were in what
they call a box. It means we were on the side and not
in a row but sort of separated. I mean we could see
people and they could see us but it was just a tiny bit
more private and exclusive. Mrs Wentworth told me
they were the very best seats. She was proud. I
thought it was really nice of her. I guessed they were
expensive or more than regular tickets cost anyway
and it felt real exclusive. We sat down just as things
started and she gave me a pair of binoculars. They
call them opera glasses.
Mrs Wentworth was obviously real excited. She
kept reaching over and squeezing my hand with a big
smile before turning back to watch. It wasn't terrible.
It was a lot of singing and not what you're used to
because you can't understand the words very well.
Even when you can, they're not English. But the
music is good and you get used to the singing. I was
using the glasses to get a better look at the singers and
maybe some of the audience. Actually mostly the
audience. Give a guy binoculars and sit him above
people and he can't help himself. Then Mrs
Wentworth squeezed over (our chairs could move)
and whispered "Amazing, don't you agree?"
I did agree but because I was looking right that
second at an older woman through my binoculars and
she had the kind of cleavage you can't look away
from. But I think Mrs Wentworth meant the opera. I
said truthfully, "I didn't know what to expect but it
really is an amazing show." She squeezed me more
and gave me a kiss on my cheek. "Such a sweet date,"
she said.
It was about this time I noticed the slit in her skirt
was pretty high and I could see almost her whole leg
if I looked. I could stockings, stocking tops, and
connecting garters because she had no idea she was
exposing herself. I know I shouldn't have looked. But
I did and I got pretty hard right away. So I took the
glasses and looked at the stage and the audience to
distract myself.
I few seconds later, she nudged me, "I know what
you're looking at, naughty boy." I was shocked and
felt bad. She was so nice to me and now she caught
me taking a cheap peek halfway up her skirt. I didn't
know what to say which happens to me a lot. So she
pinched my arm and said "a lot of men say Madame
Sofia has great lungs but we both know what that
means." And she was sort of twinkling not mad.
Before I answered I looked at the singer she meant,
the star of the thing. She was big and beautiful. I
know a lot was make up but she was very pretty and
also slightly larger, I guess the right look for a singer,
and had a very large set of lungs as Mrs Wentworth
said. And they were displayed as part of her costume.
I can see how a lot of opera fans might be thinking
less about her voice than the chest it came out of.
 Mrs Wentworth reached over and patted the large
bulge developing in my pants sort of playfully and
sort of scolding. She said "I'm sure it's the notes you
like not where they come from" and then she giggled.
I thought it was better to let her think that than say
"no it's your awesome legs and knowing you're
wearing garters that's driving me crazy."
In the first intermission (they had two), we went
back to the lobby and reception area. It was a little
more crowded but Mrs Wentworth managed to get us
two more champagne glasses. I decided that night I
liked champagne a lot. So did Mrs Wentworth. She
had two glasses in that intermission. We made small
talk with a few people for a few seconds. The lady
whose butt Mrs Wentworth had pinched when I was
behind her passed by/ Mrs Wentworth poked me and
said "isn't that your friend?" Then she laughed again.
It was all in fun, though. She was very happy and I
was actually enjoying myself. Opera was different but
fun and she just loved it when I said anything positive
about the night. So that made me happy.
Only one bad thing happened. When I came back
from the bathroom, that same oily guy had swooped
in and was trying to weasel his way into a
conversation. He left as I got closer and I asked Mrs
Wentworth, "Was that weasel bothering you again?"
She smiled and laughed. I think she was flattered that
I was protecting her but she wanted to tease me too.
"It's so cute when you get jealous. Don't worry my
sweet Stephen. I know who my date is." And she
kissed me on the cheek again.
It was a short intermission so we got stuck in a
crowd again and to my amazement she pinched the
same lady again. It's like she was trying to get me in
trouble. What was worse is that the lady was with a
pretty big guy. I really thought she was going to have
the guy hit me or something but she didn't. She just
looked at me and then at Mrs Wentworth and looked
funny and winked at me. I sort of turned a little red
and Mrs Wentworth was laughing a little when we
got past them and headed to our box seats.
The second part was better because I started to get
into it a little more and looked at the audience a little
less. Mrs Wentworth's legs though were still on
display and our seats were closer so I could really
watch her without being totally obvious. It didn't help
that she kept whispering stuff in my ear about the
opera. It was helpful in understanding the opera but a
woman you are lusting for whispering in your ear
with warm breath doesn't make the lump in your
shorts go down.
During the intermission I tried to think of things to
make myself soften so when we stood around I
wouldn't be obvious. Mrs Wentworth got champagne
quickly and then left me holding both while she went
to "freshen up." I was standing there waiting when the
lady I pinched walked by. Well I didn't pinch her but
she thought I had. I turned my head so she wouldn't
see me but she must have seen me anyway because
she came over and whispered "it's OK. I feel safer
with your hands full." And then she gave me a fun
smile and walked on.
I was staring after her not sure what exactly that
meant when Mrs Wentworth appeared out of nowhere
and asked with a giggle what I was staring at. I
stuttered. She laughed as she took her champagne
glass and said "now you have a free hand in case she
comes back." She finished her champagne and had
another one that she had obviously picked up coming
back from the bathroom. So I gave her mine so I
could make a quick stop at the bathroom myself. I
wasn't used to drinking champagne or anything else
so I was feeling different. When I came back that
weasely guy was there again. It made me mad. And
even madder when I saw he wasn't just talking to her
but really making his move. He was too close and had
moved a hand to her side. I got there and bumped him
and he let go. I grabbed his arm and said "get the fuck
away from us. If I see you again, I'm going to ram my
fist down your fucking throat and leave you bleeding
in the alley." It wasn't me. I was never like that and
didn't usually talk like that but I felt this rage when I
saw his hand on her and I was reminded of all the
jerks I knew in school and took it out on this weasel
who deserved it. I'm not a big guy at all but this guy
wasn't either and I wanted to smash him but I didn't. I
just scared him away and we never saw him again.
No one else really noticed. The only people who
might have heard were one really old couple and they
didn't seem like they heard well. Also that lady that I
didn't pinch and her giant husband. He didn't notice. I
guess he didn't notice much which is why I was alive
despite Mrs Wentworth's pranks pinching his wife. I
think she saw the whole thing but didn't say anything.
But the audience that mattered was Mrs Wentworth.
I think she probably could have handled the guy and
he didn't get far, he just touched her waist, but she
was looking at me with sort of wet eyes. She put her
arm around me and didn't tease me at all and just said
quietly "thank you, my sweet protector, you were
wonderful." I know I didn't really do anything but if it
made her happy that was great. I wasn't complaining
about her arm around me and her body close.
The lights flashed. At operas, they flash lights to say
"we're almost ready to start." So we quickly finished
our champagne. The pinching lady walked by behind
her husband and leaned over to say "very nice. Hi, I'm
Julie." I kind of blushed. I wasn't used to being
noticed. I said, "I'm Stephen and um...." I didn't know
how to introduce Mrs Wentworth. I couldn't say "This
is Mrs Wentworth, she used to be my teacher and is a
friend of my mom's." It would be lame. Fortunately,
she jumped in and said "and I'm Lana, his date. Nice
to meet you." I don't know why but I thought it was
cool that she called herself Lana again. It made it feel
different.
The woman who said her name was Julie didn't stay
because the opera was starting and she had to catch
up to her husband. We found a place for our glasses
and went into the traffic jam of people too.
Fortunately, we weren't right behind Julie again so
Mrs Wentworth wasn't tempted to pinch her and get
me in trouble again. As we got around the crowd
though I felt something pinch my butt which was
really unexpected. I looked at Mrs Wentworth but she
was looking behind us and I saw Julie back there with
a grin turning the other way.
We went back to the box and the rest of the opera
was fine except Mrs Wentworth got our chairs right
up against each other and snuggled up against me the
whole time, still happy from me yelling at the weasel
guy. It was nice. It made it harder to sneak peeks at
her leg but I felt the leg against me which was also
good.
 When we left, I kept an eye out for that guy but we
didn't see him. Which was good for him. Mrs
Wentworth held my hand which was kind of cool.
She said "Stephen, honey, a woman likes her date to
hold her hand so keep a tight hold of your Lana." I
know it's crazy but I kind of felt like she was really
was my girlfriend right at that moment.
We walked back across the walkway to where we
had dropped the car with valet parking. But before we
went down the escalator, she said "wait here while I
go take care of something." After all that champagne,
it was a good idea to go again before we hit the road
for a long car ride. So I stared at the city lights
through the walkway glass. It was very nice.
When she came back, she took my arm and said
"ready." Then she led me right past the escalator.
"Mrs Wentworth, I think we go down there," I said.
She smiled. "I'm Lana tonight remember? This is a
date. I thought that since it is such a long drive back
to our house and we both had a few drinks, it would
be smart to get a room and drive back in the
morning." It was only then that I noticed that this was
the lobby level of a hotel and actually a pretty nice
one. "Okay, Lana," I said. "That's pretty smart." She
was right. I never drink much and I was a little light
headed and she'd had even more.
 We went up in an elevator. I guess she had gotten a
key when I thought she was heading to the bathroom.
"Is your car, okay where we parked?" I asked. She
assured me, "oh yes, I told them when we dropped it
off that we were staying over."
So we got to our room on the 14th floor and I
immediately noticed the view and nothing else. Wow.
We were high up and it was nice. When I turned
around, I noticed only one bed and it had a suitcase
on it. "Uh, Mrs… I mean Lana, there's only one bed
and someone's suitcase is on it."
She acted pretty annoyed. "That's very annoying. I
know I told them I wanted two doubles and now it's
too late to do anything about it. I'm so sorry Stephen.
I hate it when they mess things up like that. Oh, but
the suitcase is ours. I told the valet when we parked
that it was in the trunk so I know they'd bring it up." I
was confused because I know we didn't leave the
house with a suitcase unless she had packed it hours
before which was impossible unless she thought there
was a chance we might need it and was being safe.
"Now, why don't you buy Lana one drink, a
nightcap before bed? If you like our view then you'll
love the bar at the top of the hotel." And without
waiting for an answer she grabbed me and took me
out the door and we took the elevator to the top.
There was a restaurant and the bar had seats on the
windows which had an amazing view. It was like you
could see the whole world.
She had ordered more champagne which was okay
with me. Then we sat there and she turned to look out
the window, twisting herself around. "Don't you just
love the view, dear?" she said. I was staring at the
huge amount of exposed leg she was showing. All the
way up, I could see stockings tops and garters and
even just on her hip the bottom edge of her panties. I
was lucky I heard the question and could say "uh, yes,
I really like the view too."
I was disappointed when she turned but liked it
when she leaned closer and put a hand on my thigh
and said "Stephen I was so very very happy to be able
to share this night with you. I think it was very fun to
be with you at the opera for your first time. I like
introducing you to new things and I like being your
date." It was very nice and nicer too when she leaned
in and gave me a very nice soft kiss on my lips not
my cheek. That even more than the leg show got me
very excited and obviously to anyone who could see
into my lap.
She took another drink on her champagne and
smiled. She was obviously happy. She said, "I could
tell you thought Julie's husband was going to come
after when she got pinched. That was funny." I was
going to protest but she leaned in again to say in a
little bit huskier voice "but it was just the most
exciting thing for me when you chased that man
away. It was so wonderful to be protected by you that
way." And I just got a little embarrassed.
She looked thoughtful for a few minutes before
saying, "I do have to say, however, that even though
your action was very gentlemanly and proper, I think
your language was very naughty. I never thought I
would hear such coarse words come out of my date's
mouth. I know you were provoked so you might not
have to be punished."
"Uh, okay. Great." I didn't know what to say. She
started to get up but then fell back down again and
actually almost fell on top of me. She actually just
missed crushing an important part of me and even
leaned on the bulge in my pants when she got herself
back up again. I thought she didn't notice what she
had touched until she giggled. No one much was in
the bar because it was pretty late but we decided to
leave anyway. I mean she decided and I followed her
back to the elevator.
When the elevator started in threw her off balance
and she actually fell backward which was okay
because I was between her and the wall. It cushioned
her so she didn't get hurt but it also meant her butt
pushed into my waist so her beautiful soft cushiony
butt was pressed against my erection. That happened
three or four times. I guess she was a little drunk.
But we got back to the room in one piece. I was
trying to figure out if I should sleep on the floor or I
could make a sort of bed out of two chairs. She
stopped me. "Stephen, honey, please. I know we
wanted two beds and that would be appropriate but
it's a big king-size bed it won't be a problem. I think
Stephen and Lana can share a bed like two mature
adults." I was never sure what it means when she
talked about us like we were two other people or
when she called herself Lana. I know it was sort of
still the date and she was Lana on the date but it was
still weird to talk about yourself that way. She was
right though. It was a big bed so why not. Then I
realized that I hadn't known I wasn't going home so I
didn't have spare clothes or anything to sleep in. I was
pretty sure she wouldn't approve of me sleeping with
her in just my underwear.
I tried to think of what to say but she had apparently
thought of it. She was opening the small suitcase on
the bed and saying "Now, my sweet Stevie I bought
you new jammies for tonight because the opera is
special and why not? If we are elegant people tonight,
we won't sleep in shorts and T shirts. I know you like
shorts though so I got you jammies with shorts,
sweetie." With one sentence my bulge was gone. She
got me jammies. I don't think I said the word jammies
in almost forever. But still it was nice and at least it
solved the problem.
She laid them on the bed and said "they are elegant
satin pajamas, dear. Very high society. I know you'll
like them." Actually they were pretty nice as far as
pajamas went. I had taken my coat off and now my tie
until she turned her back to me. "Now be a good little
helpes and take care of my zipper." She stood funny
and I pushed against her to get her zipper started. She
whispered, "Keep going, Stephen." and I pulled all
the way down past her waist. I could see the back of
her bra or longer than a bra actually, and the garter
belt that was holding up her stockings and the top half
of her panties. It was one of the sexiest moments of
my life.
The she took a step away an wiggled and the dress
fell down. "Help me hand the dress up, dear. Get the
hanger over there." I helped her and tried not to think
about it. She was out of her dress. I took a minute to
stare. She was wearing the sexiest underwear I ever
knew existed. I don't know why anyone needs garters
anymore but they are very hot. Her panties weren't
tiny but that's almost better. Most of it was black and
matched. On top she had something I had never seen
but I checked on the internet later and it was a bustier.
Wow.
 I wasn't very subtle because she said, "Oh, I don't
know what you think. Maybe my foundation
garments are too old fashioned but we were going to
the opera and they make me feel pretty. After all, no
one was ever going to see them. Except you of course
right now." I never heard anyone say foundation
garment before. But I didn't want her to think the
wrong thing. "No, actually Mrs Wentworth...." She
looked at me like she was going to scold me. "I mean,
Lana, you look awesome. What I mean is that you're
very pretty and I think your clothes are very nice."
She smiled and came over and gave me another
kiss. A big kiss, soft and long, with her body pressed
against me. And my body knew that an attractive
woman was kissing me in just her underwear, fancy
underwear. I didn't want it to stop but she was just
being nice. She turned with her bag and went into the
bathroom saying, "Now I better change so you can
have privacy to put your jammies on."
I quickly changed, took off everything and put the
pajamas on. They were a burgundy color and soft
shiny silk. They actually felt really good against me,
almost too good. I still had a hardon and having it
press against the thin silk was nice. Then Mrs
Wentworth came back out saying, "I got new jammies
too." She also had silk but a long, almost to the floor,
satin nightgown. It was so nice and lacey around her
breasts she could almost have worn it to the opera. I
just stared.
She smiled at me and said "which side do you like
best?" I loved that question and just stared at her,
comparing sides, until I said "I like both." She smiled
and said "well you have to pick one. I'll take the right
and you can have the left." Then she pulled down the
bed spread and I realized what she meant. So I
climbed into the bed before she got a quick drink of
water.
Before she climbed in, she pulled the covers back
and looked at me. "Oh they look darling on you. I
hope they feel as good as they look." Then she got on
her knees and elbows and leaned over and gently
stroked the shorts, not in that spot that would have
made me explode but on the thigh nearby it which
was still nice. I had a huge tent in my shorts but she
didn't say anything at all about it. I tried not to look at
the cleavage she was showing me but I just couldn't
help it. Her breats were hanging down because of her
odd position, sort of like she was on all fours. I kept
staring when she sat up and was frozen looking at the
bumps her nipples made in the silk and lace cups of
her nightgown. Even when you can;t see anything, the
bumps are really sexy. It was pretty cold in the hotel
room but maybe she was also still excited a little from
the evening. Anyway, she didn't notice that I was
staring even though I was obvious but she did turn
over and turn off the light ending the show.
Then we settled in. The only light in the room was
from outside. She had the curtains wide open and the
night glow of the city was almost like candlelight in
the room. I thought we'd just go to sleep but she
decided to talk. "Stephen, my sweet darling, I had
such a wonderful night. You were a wonderful date
for me. I want to thank you for this special time
together with me." I felt warm when she said that and
suddenly felt her hand fumbling under the overs
reaching for me. She accidentally bumped by
twitching erection but she was trying to find my hand
which she grabbed and squeezed. I had to respond, "I
had a great time too, Mrs Wentworth, I mean Lana. I
was happy to be your date and it was night full of
surprises and it made me happy to see you happy. I
mean I was happy too but it's really nice and cool to
know that the person, I mean that your date is happy."
I guess that was the right thing to say because she
turned a little and grabbed me and pulled me close to
her and gave me another nice tight kiss with our
bodies pretty scrunched together. I liked that even
more. My legs were bare so I could feel her
nightgown against them. And the only thing between
us was my layer and her layer of thin silk and satin.
I'm sure she was focused on being happy but my
mind was very aware of my hardness pressing into
her body and the silk. I was also very aware of her
soft breasts pushed against me and I swear I could
feel her nipples poking my chest. I had to actually try
not to explode and ruin the moment.
She let go but only after she rubbed her hands all
over my back and the rest of my body, especially my
butt. She said she just loved the way my new jammies
felt and that was why she had her hands all over me. I
just agreed and said "yeah, that feels very nice."
She rolled back over but not very far away even
though it was a big bed. "I'm so glad we didn;t try to
drive back to our house tonight. This is a lovely hotel
and also nice to share with a friend. It's very cold
though, isn't it, Stevie? It's warmer under the covers
with someone else there to keep the chill away.
Especially when he is my date and protector of the
evening." That made me happy to hear. Suddenly
though, she was back over and pressed against me,
one leg over mine, not ont top of me but we were
connected. She was whispering in my ear even
though were were alone in a room with no one we
knew within miles of us. "Stevie, honey, I just
thought of something. You know this is all very
innocent and we are just here because it would have
been wrong to drive after having so much
champagne, right? And you know that the room was a
mistake, we were supposed to have two beds right?
And it's a big bed so it doesn't matter because we're
both mature enough to be good, right?" She didn't
wait for answers and her mouth was right against my
ear so her warm breath was pushing into my mind.
"Stevie, I don't think we should tell your mommy.
Sometimes mommies don't understand or even listen
and I don't think yours cares anyway." I didn't know
what she meant exactly about my mom but I don't
know why she had to say "mommy" and be kind of a
buzzkill to my fantasy. But she was right so I said "Of
course. I mean I never told anyone about dates I had
before and I am not about to start now." I didn't feel
like mentioning that I hadn't had very many and none
of them really included anything like this before.
She said, "I knew we agreed about this." And then
she gave my ear a little kiss and a little lick and a
little bit of a bite. I know she was being playful or
friendly or whatever but I actually thought it was
erotic and it did the opposite of talking about
"mommy." That had deflated me and now I hardened
right back up. The in rolling over, she dragged her leg
sort of up and off me which made it rub and give a lot
of friction to my hardon. I was pretty calm about it at
first but I couldn't help actually groaning out loud.
She didn't say a word.
 Then we settled down to sleep, on our own sides but
kind of in the middle. When she turned, her leg would
bump me. I think we were just inches apart. I faced
away from her but I could feel her moving restlessly,
she was twisting and turning, trying to get
comfortable I think. I didn't mind and the sound of
her gown moving and rustling was kind of a cool
soundtrack. I quietly rolled back the other way
thinking why not stare at the beautiful woman laying
by me. She was on her back with her knees up and
squirming a little. She was half asleep but her side of
the covers were at her waist and I think her left hand
was on her breast and her other hand between her
legs. I thought she probably wasn't exactly going at it
but she might have been doing a little something. I
never knew because right after I rolled over, she
changed position and pulled the covers up. She
mumbled something about being cold and backed her
body into mine. The she yanwed and said "I'm
freezing, maybe this will be warmer."
And that's how we went to sleep. She pressed back
into me to keep warm and then pulled my arm over
her body. It was warm and my hand over her and on
her stomach wasn't bad. I think it helped her sleep but
it kept me awake. My hand on her could feel her deep
breaths as she fell asleep. Her hips moved a little but
since she was pressed against me, I could feel her
nightgown covered butt warm and soft against me. I
was embarrassed that my hardon, rockhard now, was
pressing into it. It meant that when she squirmed a
little it was like a small grind. We stayed like that a
while. When I whispered, "Mrs Wentworth, are you
awake still?" she didn't say anything.
I would have rolled over, probably, but our legs
were tangled a bit and she sort of had my arm. I don't
know why but I couldn't stop myself. When I looked
over her shoulder to see her face and that she was
asleep, I noticed she had my hand pressed pretty high.
I was just inches away. So when we moved, a little
restless adjustment, I pushed a little and my fingers
ended up on her breast, she had my wrist but the
fingers could move. I spread them a little and then
they were on each side of her right nipple or the bump
it made in her nightgown. So I closed the fingers and
opened them a little to gently squeeze her nipple. It
was incredible and didn't wake her up so I kept doing
it like a little scissors pulling on her.
It made her a little more restless which I guess
wasn't a surprise but she didn't wake. That made
things worse. Her restlessness caused her butt to
squirm more and I felt it. After about ten minutes of
that, I stopped with her nipple caught in between two
fingers tightly and my hips got tense and I had a
better orgasm than any masturbation with her
nightgown covered butt tight against my cock. I made
a mess in my pajamas. I think most of it stayed in
there but maybe some got on her nightgown. I relaxed
my hips but her tight grip on my wrist meant I
couldn't pull away. I also let go of her nipple, a little
ashamed of myself. Not long after that she seemed to
rest deeper. There was almost no squirming and I fell
asleep pretty fast too. The whole situation was almost
unbelievable. I had no idea what the morning would
bring.
Mrs Wentworth and a Useful Lesson
This story comes immediately after "Mrs Wentworth
and a Night the Opera" which followed the three
chapters of the "Staying with Mrs Wentworth" series.
I really appreciate all the comments people made
both publicly and privately on those stories. I benefit
a lot from the comments and thoughts that help me
understand how some characters are feeling
(especially the female ones) and some of the details
like fashion and things I have less experience with.
And I try to always reply to feedback. I hope you
enjoy reading as much I'm enjoying writing.
The morning after the opera, I woke up in the hotel
next to Mrs Wentworth (see Mrs Wentworth and a
Day at the Opera). This was only the fifth day I'd
been with her since the start but it already seemed like
a long time. When my mom had first made me go
stay with Mrs Wentworth, I was angry (see "Staying
with Mrs Wentworth"). After all, I'm an adult. I was
19 and grown up but my mom was making me stay
with an old teacher of mine. Actually Mrs Wentworth
wasn't really super old, she just had seemed that way
to me when I was in fifth grade so many years ago.
But still, I was an adult and just because I still lived
with my mom, she thought she could make me stay
somewhere when she went on a business trip. I had to
admit though, I was enjoying it now and really liked
Mrs Wentworth. It wasn't just a crush, I didn't think. I
felt like I really cared about her and liked being with
her.
The night at the opera was a lot of fun even though
it was opera. I felt like she was treating me mostly
like a grown up. And now I was next to her. It was
sort of an accident. After all, it was a coincidence she
had thought to pack an overnight bag and put it in the
car. And we were lucky she thought to rent a room in
the hotel just in case we had a few drinks. And even
though she was a little drunk, she told me she had
asked for two beds. It was a mistake the hotel gave us
just one. I was lucky she had packed new silk
pajamas for me. It was thoughtful. Still, all those
coincidences led to me sleeping next to her even if it
was mostly innocent.
I had been surprised how fast she fell asleep and
how tight she held my arm in her sleep. I felt guilty
about playing with her nipple. My fingers ended up
against that part of her nightgown by accident of her
sleep movements. And when I came in my new
pajamas while pressed against her I would have
cleaned up if her sleep grip wasn't holding me there.
Anyway, when I woke up it was from feeling the
covers pulled back and watching her slink out of bed,
trying not to wake me up. I enjoyed the view of her
getting up and didn't say a word. But when she
returned from the bathroom, I pretended to be waking
up. She didn't notice until she had climbed back in
bed and squished next to me.
"Good morning sleepyhead," She said. Did my
sweet Stevie have a good night's sleep in his darling
new jammies?" She kept the covers down and looked
at me. I don't think she noticed the staining which had
dried but she must have noticed my morning
hardness. I wake up most morning with an erection.
And I knew my morning wood was making a tent.
I didn't want to call attention if she didn't and I also
felt weird, like usual, when she said things like
jammies. I'm a grown up and she sometimes treated
me like a kid. So all I did was smile and say "Good
Morning."
she reached over and started rubbing my pajama
shirt and said, "I just love the way silk feels against
skin. These are so soft of slippery and wonderful
feeling, don't you agree? Don't you love the way this
feels?" She kept rubbing my shirt softly on shoulders
and chest and even stomach.
This was killing me, I loved it. I could feel my cock
twitch in my pajamas and I wanted to hide it but I
didn't want to call attention to it. She just lay there
rubbing my pajamas shirt and smiling without
realizing what she was causing I guess. All I could
say was "Yes, I agree. It feels great Mrs Wentworth."
She didn't need to know what I meant.
Then she stopped and looked past me at the night
stand on the other side. "Wait," She said. "Let me
grab the program." She meant the program from the
opera the night before. She moved to reach over me
or crawl over me. I was pushed onto my back and she
was on top of me leaning over. It was awkward. Her
breasts were hanging partly in my face really but that
wasn't the worst of it. Or best of it. Because she was
stretching, trying to grab the program and having
trouble, her body was sort of squishing my hardon.
Her hips pushed on it and her reaching and stretching
made her sort of wiggle around on me. I groaned
silently and tried to pretend nothing was happening
but really I wanted to just grab her and do something
right there. I think if I had been more experienced in
the sex department I might have.
I concentrated and tried hard not to explode and
embarrass myself. Finally she found it and slid slowly
off me. She showed me the program and I didn't hear
what she said because I was staring at her nipples
making bulges in her nightgown and trying not to be
obvious.
Finally, she said something about a shower and she
got out of bed and went to take a quick shower.
Eventually, we both had showers. Mine was a little
cold to calm me down. But we got dressed. She had
packed clothes for me for today too. Not a suit but not
jeans either. My pants were dressier and it seemed
kind of adult. But by the time I got ready, she had
packed everything and we headed downstairs. In the
lobby she had me give the suitcase to a worker there
who took it to the car and we went to have breakfast.
While we ate, she said we were going to spend the
day together in the city and have a nice time together.
I was happy knowing that I would be happy just being
with her. It was different but I really didn't care at all
what we did. I just liked spending time with her.
After breakfast, we were walking to the car but she
wanted to cross back over to the opera house first.
Obviously I came too. It wasn't very early because we
hadn't made it out of bed and down to breakfast very
early. But it was around 11 in the morning so the
information window was open. While she talked to
them, I looked around. I didn't know what she lost but
I just wanted to look at the impressive building.
Anyway, she came back with a big smile and put
her arm in mine and walked around with me. In fact,
she pushed us out of the main hall and into the area
where the boxes were. I still think the boxes were one
of the coolest parts of the whole thing. We went into
the one we sat in before. We stood there looking at
the empty theater and she said, "here it is sweetheart:
our box, our special place to watch the opera and all
the people."
I have to admit I liked it. Here I was with this
person I was getting to know better all the time and
feel happier to be with all the time. And we were in
this luxury kind of place, a private opera box. She had
her arm in mine and was squeezing me close to her
and I loved it. She really did something to my insides
in a way I would not have predicted when I first came
over to her house and was annoyed at having to stay
with her.
I also liked when she called me sweetheart instead
of some other things that were more demeaning.
Sometimes she seemed to treat me like I was less
mature than her even though I was absolutely an
adult, just a younger adult than she was. But
sometimes women talk that way about jammies for
example. Sometimes though, we had a much more
mature relationship. After all, a couple very sexual
things had happened between us. The circumstances
were always a little odd but they were still very
erotic. Sweetheart was one of the words that could be
taken different ways but I took it like a word she
might say on a date with a guy she liked.
It may seem weird but feeling her pressing close to
me and moving her arm around my waist as we stared
at the empty theater made me a little bit horny.
Actually, something about her always seemed to
make me horny. It didn't hurt that her hand wasn't
exactly on my waist but had slipped down a little and
she was using my back pocket for her fingers. It
sounds perfectly innocent and I'm sure it was for her
but her fingers in my pocket right there actually made
me a little bit hard. It didn't last because some
security guard poked his head in and told us they
were closed and we shouldn't be there.
That was okay, though. We walked away and back
out of the building. She had her arm in mine all the
way to the car which was waiting for us. I wasn't sure
what was next but we drove a few miles away and
went shopping. Obviously I didn't need anything but
Mrs Wentworth was looking in a lot of different
shops. She didn't buy anything at first. We walked
arm in arm like she needed support but I think she
was just keeping me close.
We ended up in a shop that sold a lot of dresses
after visiting five or six others. A very nice woman
helped her out and showed her dresses while I waited.
After what seemed like forever, she looked at me and
said "I don't buy a thing unless Stephen approves of
it. Honey, will you tell which of these three you like
best? It's what I'm going to wear tomorrow night." Of
course I had no idea what tomorrow night was but I
went along and thought I'd figure it out.
 The saleslady smiled and everyone seemed happy.
The two of them went into a dressing area and finally
came back out with Mrs Wentworth wearing a long
dress. It was some kind of plaid and had a high neck
and was kind of boring. They both looked at me and I
just shrugged and said "it's nice I guess." They went
back.
Then they came out with a very different dress. It
was a lot shorter and pink and very tight. It may have
even been too tight. Mrs Wentworth said "I know you
can see my underwear lines and tell what I'm wearing
underneath but ignore that and pretend I'm not
wearing anything under it." I didn't say anything
because I was imagining what she just said about
wearing nothing under it.
She frowned and said "I can tell he doesn't like it."
And then she turned and went back and the other lady
followed.
They came out a third time and I liked it much
better. She could tell by my smile but I said, "wow!
That's nice."
She smiled and so did the other lady. "I knew he'd
like it better," Mrs Wentworth said. It was a nice blue
dress. Not slutty or anything but it had a lower neck
and sort of hung down looser. The skirt was not tight
at all. It was actually longer and real loose but it just
seemed better on her.
 While the other lady went to get some shoes or
something, Mrs Wentworth bent over to the chair I
was sitting in and kissed me on the cheek. "I'm glad
you like what you see," she said. I did like what I saw
because when she bent down, the dress hung loose
and I could see down her neckline and see her whole
bra practically. It really did look good on her but that
definitely sealed the deal for me.
She went back and changed back to her other
clothes and we left after paying. It was nice although
she made me carry the box they put her dress in and
then another box from a shoe store we went to next
and then a smaller box with cookies and then a fourth
box with a purse in it. I felt like a servant at that
point.
We had shopped for hours and skipped lunch. But I
really didn't mind. I had fun. But now my hands were
very fell and so we went back to the car. The car was
in a parking garage because street parking is almost
impossible in the city. We loaded the trunk with the
boxes and then I held the door so she could get in.
She likes it a lot when I hold the door. But I think she
brushed against something and she asked me to help
brush her off.
I didn't see much but I brushed some lint or
something off the back of the blouse she was wearing.
I was gentle of course but when you brush you can
feel everything. I kind of liked brushing and feeling
her bra through her blouse. It was the back of it but it
was fun.
She said, "No, Stephen," and I worried I was too
forward. But then she added "the blouse isn't so bad. I
need you to do the skirt, dear. Be a good boy and help
me out." When she said it, she put her hands on the
side of the car and bent so her butt side stuck out and
the skirt was tight against it.
I wanted to be helpful to Mrs Wentworth and I
didn't mind the opportunity to place my hand on her
butt too. So I brushed a little slowly. She didn't notice
or she didn't mind. I didn't want to go too long so I
stopped pretty soon. But then she told me, "please be
very thorough. Make sure you get everything." Then
she bent a little more to give me a better angle I
guess. I liked that. He skirt got tight from stretching
and I could see and feel her panty lines while I
brushed her off. It was pretty sexy and I got pretty
hard. I think I brushed a little slow and cupped my
hand a little so it was a lot like feeling her. Finally I
stopped. I loved doing it but I didn't want to push my
luck or make her think I was taking advantage of her.
When I stopped she almost seemed disappointed.
"Oh, did you finish? Thank you, dear Stephen."
Then we got in the car and I started driving. She
told me where to go and I realized we were done with
the city. On the way back to where we lived, I mean
where Mrs Wentworth's house was, she directed me a
small shop in a quiet shopping plaza. When we
parked, I went in with her. It was a little embarrassing
because it was a store for ladies underwear and
lingerie. I was allowed in because I was with her and
no one seemed to mind but Mrs Wentworth was
looking for something special. The sales helpers were
all well dressed women. I guess I didn't know what to
expect. It's not like they'd all just be wearing
underwear or nightgowns. But the mannequins were
all very sexy. I even found myself staring at one and
thinking how cool it would be to take the mannequin
home and do whatever I wanted.
But when I stopped daydreaming, I found an older
lady talking to me. "Please sir, if you would follow
this way while Madame tries on some clothing." I
followed her and realized I wasn't paying attention
and hadn't seen Mrs Wentworth wander into a helping
area. The older lady found me a chair and placed it
right near the door to the dressing room.
I tried not to look but then couldn't help it. The
room had a curtain and it was open a crack so I
couldn't help look through. I kept leaning forward to
tie my shoe because when I was bent forward like that
I could subtly look through the curtain's narrow
opening. Unfortunately, Mrs Wentworth was in
another room inside that area. The sales helper was
talking to her and holding clothes and helping her
decide. Then, suddenly, I heard her say "oh that's a
good one to keep too. Come look at it in this mirror
by me." And then Mrs Wentworth came out of the
inner room and into the outer area. My eyes almost
popped out. She was wearing the greatest underwear.
It was black with white dots but everything matched
and it included panties and a bra and stockings and
even a garter belt.
I only got a short look because the older lady came
back right then and saw me bent down and asked, "is
everything okay?" I sat up real fast and sat back in my
chair and tried to act natural and just be relaxed. She
smiled and almost laughed. I think maybe I was
busted. But she sat down and asked me if I liked to go
shopping. "I don't think I've seen you in my store
before. Is this your first time or is she buying
something for you?"
I got red a little from being angry but also a little
embarrassed. "No, of course it isn't for me. I mean I
never come here at least I didn't before and I'm just
helping."
I'm sure I was a little hyper but it was good that Mrs
Wentworth came out right at that second. She hadn't
gotten dressed again and didn't notice me when she
went by to bend down and look at some shoes on the
next shelf over. She stayed bent for a while so I really
had no choice but to have a very close up view of her
gorgeous full butt in flimsy, very sheer, but with a full
back piece silk panties.
She slipped the shoes on and admired her feet in a
low mirror before walking back into the dressing
area. She noticed me just at the end and added as an
afterthought, "oh hi there sweetie-pie, almost done
and we can pack up my purchases and go." The she
disappeared.
The older lady gave a soft laugh, kissed me on my
cheek, and said "see you later, sweetie-pie." Then she
left giggling.
Minutes later, Mrs Wentworth came out and walked
quickly past so I had to get up to follow her and her
helper. We went up to the front and the older lady
checked us out, taking the money from Mrs
Wentworth, handing me the bags, and winking at me.
To Mrs Wentworth she just said, "I hope we get to
see a lot more of you in the future. We want to thank
you for your business and look forward to fulfilling
all your needs." Then we left.
I put everything in the trunk. We'd bought a lot that
day. As I started driving away, Mrs Wentworth was
returning a phone call. I didn't know who she was
calling or why then I realized we hadn't talked to my
mom. I mean I hadn't. I didn't want to really and
fortunately that isn't who she was calling. I heard her
say, "Hi Janine. Of course I didn't forget. We aren't
late are we? Why, I'm with Stephen of course. Now,
stop that. You really are very wicked. He's very
helpful. No. No. Stop it. I know you're kidding. Yes,
we were just about to head your way. Great. We'll see
you soon."
She hung up and frowned. "Darling, I have bad
news. My dear friend Janine had invited me over for
tea and I can't believe I forgot. I'm sure you remember
her from our tea party. I'm sorry but we have to go. I
hope you don't mind."
I did remember Janine (see Staying with Mrs
Wentworth, Day Three) but I didn't say what I
remembered just "yes of course. I don't mind at all.
I'm more than happy to go anywhere with you." It
was the right thing to say because she smiled real big
and kissed me even though I was driving.
When we got to Janine's, she had a nice house but
not as big as Mrs Wentworth's. It was nice though and
she let us in. She was alone but told us her husband
was at work but Kim was going to stop by in a little
while but no one else. Actually, she looked real good.
Her dress was lower cut than last time and I could see
the line of her cleavage. I liked Mrs Wentworth a lot
more but Janine was distracting. She hugged Mrs
Wentworth and winked at me over her shoulder while
she was doing it. Then she grabbed me and said
"come here you cute thing." Then she hugged me and
grabbed both cheeks of my butt and pulled our hips
tightly together.
Mrs Wentworth looks disapproving, like the teacher
she used to be and said, "stop that Janine. You'll set a
bad example."
We separated and everyone went into the kitchen
with Janine pinching my butt as I walked. We walked
through the kitchen where Janine had been cooking
and drinking too if the half empty bottle meant
anything. We went through to the dining room. I
guess these ladies had tea together a lot. While we sat
down, Janine rushed off to the door because Kim had
apparently arrived. While she was gone, Mrs
Wentworth whispered to me to be careful because
Janine was unpredictable and could be "mischievous
when she's been drinking. I don't want her to give you
the wrong idea."
I was about to sit down when Janine came back with
Kim behind her. "Kimmie, you remember the
delicious Stephen don't you? Give him a hug." Then
she pushed the shy Kim into me and we hugged each
other tighter than we might have because Janine was
pushing Kim into me.
We sat down and Mrs Wentworth helped Janine
pour the water for tea. The good news is there were
little cakes on the table and cookies. In addition to
tea, Janine gave each of them a martini. I noticed Mrs
Wentworth drank hers pretty quickly. Janine does that
to her I think. I didn't get a martini but I did have
some of the tea. I also was the first one to help myself
to the cookies. I guess no one wanted to be first but I
didn't mind.
Janine had arranged things so I was right next to her
around a small circle table. She reached next to me
and put her hand on my knee. Then she said loudly,
"He seems very hungry. I hope he doesn't just eat
cookies." Mrs Wentworth didn't react but she glared
at her again.
Janie said, "I'm glad everyone came. I hate to just
drink alone. Tea, I mean. Now that everyone is here
we can have martinis. Help yourself to the pitcher on
the table. No one wants just one do they? Now, dear
sweet Doris, please tell us all about how you've been
corrupting your delicious young man today." I sort of
liked being called delicious and she looked at me
almost like I was a steak she was going to eat.
On the other hand, Mrs Wentworth took things
differently. She did help herself to another martini.
But she was getting more annoyed with Janine. Or
maybe embarrassed. "Janine, please! We're all happy
to be here but you give Stephen such a bad idea of
how respectable ladies behave. We've done nothing of
the kind. I expanded Stephen's cultural education at
the opera last night and he accompanied me on some
shopping today. Then we joined the two of you for
tea. It's all very respectable."
Janine rolled her eyes. "Doris, could you be more
boring? Opera and shopping aren't exactly the wild
life kids are hoping for. You could have at least
stayed out all night at downtown bars or slept in the
park. Did you at least buy something fun? I'm
surprised our young stud didn't fall asleep last night
or today." Then she reached over again and squeezed
with a hand in my lap and on my thigh.
I stayed calm and had another cookie but Mrs
Wentworth got defensive. "Stayed out all night
indeed! We went home and got a good night's sleep."
She was lying. Not that it mattered but she tried not
to look at me before she continued. "Then this
morning we went to a few stores and bought a few
things I needed and some groceries." I guess she
didn't want to talk about where we went which was
okay with me but I didn't know why she didn't want
to say.
Janine turned to me. "Stephen, I'm sorry. Opera
wouldn't be on my list. I'd take you to a motel and
spend the afternoon giving you a completely different
education. In fact my husband won't be home for an
hour. We could ditch these two and go upstairs so I
can give you some private lessons unless you think
we should have Kimmie join us for a threesome?"
She grinned.
I knew she was teasing but Kimmie just giggled
while Mrs Wentworth yelled at her. "Janine!
Honestly, stop it. You're just trying to shock us now."
They were sort of mad at each other but not
completely. It seemed like it was a kind of teasing
they were used to. And they soon started talking
about something else as if nothing had happened. But
I was daydreaming about what they said and trying
not to look like I was picturing the whole thing in my
head.
They kept talking and I stared at each woman one
after another. It was fun being there with them even
though this was kind of boring. Janine was very flirty
and it annoyed Mrs Wentworth. I think she noticed
each time Janine reached over and patted my leg. She
did it a lot. I think Janine was teasing me on purpose.
And each time she talked to me, which was only a
few times, she turned in my direction and did it. The
last two times she actually reached over and grabbed
the bulge in my pants and squeezed. Mrs Wentworth
glared each time and on the last time actually hissed
angrily at her. I guess that stopped it.
Janine was drunk I think. She'd had three martinis
which is a lot and I was sure she'd had a drink before
we got there. Mrs Wentworth had three too but she
didn't have anything first and she was still a little on
the drunk side.
Janine's dress was the kind that wraps around and
ties. It makes great cleavage but also when you sit
you can play with and expose lots of leg like Janine
did. In fact, she exposed a lot more. She moved a leg
outside the chair and pushed the bottom of the dress
up pretty high. I know she did it on purpose because
she looked at me and smiled and looked down so I
could see she was showing me her panties. They were
very blue and had lots of lace trim. I had to look.
Mrs Wentworth was real mad and Janine seemed to
be trying to make her madder. Suddenly she grinned
and said, "Doris, you said something about shopping.
I think I bought more fun things than you did. The
new undies I bought are probably better than
whatever you are wearing. Let me show you." Then
she stood up and untied her dress and unwrapped
herself. The bra matched her panties and she was
definitely right about looking good. Then she walked
over and showed herself to me but talked to Mrs
Wentworth even though she was looking at me.
"Doris, maybe we should all open our dresses and see
whose underwear your delicious pupil likes best?"
Then she leaned in and her breasts were six inches
from my head. "Does Stevie want to judge all his lady
friends? Hmmmm?"
I think I was smart to be quiet. Mrs Wentworth was
up and over and pushed Janine back. She seemed
pretty mad. "Sit down you drunken bitch and stop it.
You're just trying to make me angry and it won't
work."
Then Janine, who really was trying to make her mad
and had succeeded, just giggled and said, "Doris, my
love, I don't want you to be mad. I just want Stephen
on his knees to eat me. But if you want to lick instead,
I don't mind." And then she just started laughing.
Mrs Wentworth didn't react how I thought. That
didn't make her mad anymore. She just turned and
said "We should leave, Stephen. I think Janine needs
some alone time. Why don't you thank Janine for the
tea and we'll be on our way."
I thought would create another fight but it didn't.
We just got up and I said thank you and Mrs
Wentworth said "Thank you Janine. We'll have to do
this again soon. Oh, why don't we give Kim a ride,
she's had as much as I did."
With that, we all moved to the door and it was like
nothing had happened. Janine had completely
removed her dress but hugged both Mrs Wentworth
and Kim like friends. Then she grabbed me and
kissed me very hard rubbing her half naked body
against me. She let go and whispered in my ear "next
time we fuck." Then she smiled and we all left.
We got in the car with me driving. The others had
had a few too many. That's why we were driving Kim
home. She actually lived nearby and we dropped her
at her house. Mrs Wentworth walked her to her door
and they talked for about a minute before she came
back. Then Mrs Wentworth got in and we headed
home. I waited a few minutes and nothing was said so
I jumped in. "So, what was that all about? It was kind
of a weird afternoon, huh?"
Mrs Wentworth sighed and then looked at me while
she thought about what to say. "Stephen, you're such
a good sport to put up with all of us. Janine must have
been shocking to you."
I knew I should have been shocked I guess but I
wasn't really. In fact, it kind of turned me on but I
knew enough not to say that.
"Mrs Wentworth, I wasn't shocked at all. I mean I
have friends who are a lot like that so no big deal. I
just wasn't sure how everything went and how we
knew when to leave and stuff like that."
Mrs Wentworth smiled and said "you have friends
like Janine? A lot of the girls you know tease you,
grab your crotch, invite you to get on your knees and
take their dresses off? Maybe you lead a more
exciting life than I think Stevie dear."
 I knew she was kidding but I couldn't help being
embarrassed. "No, I didn't mean that. I don't know a
lot of girls who are into anything really. But, you
know, some people do stuff and talk certain ways. I
just mean I was cool with it."
She reached over and patted me on the knee and
laughed a little. "Yes, of course. Actually, sweetie,
Janine has always been a little wild and likes to get
crazy sometimes. She also likes to drink and that
makes her crazier. I could tell you stories about when
she and Kim and I were all younger. Never mind
though. I was a little worried that she was might have
been a little bit serious about trying to seduce you.
But most of it was just to try to make me angry. She
has always liked to tease me for fun. There was a time
in college when, well never mind. I knew it was time
to go."
Then Mrs Wentworth got less serious and playfully
slapped my arm. "Not that you seemed to complain
when one of my best friends was almost naked and
throwing herself at you. Maybe that's what you like,
dear. You like to have all your women strip to their
underwear and drape themselves on you." She was
laughing but made it sound like a crazy movie script.
I just laughed too and said "no, no. I don't like that. I
mean that isn't what I was thinking. I mean it hasn't
happened before. She's your friend and I was being
polite." She laughed and smiled at me.
By then we were home and she let me hold the door
open for her before she got out. It was a little like I
was her driver and a little like I was her date. But
while she opened the front door, I got most of the
bags and the little suitcase from the trunk and brought
them in. She took two of the bags and asked me to
take the others up to her room.
I took everything up. Since she was downstairs and
I had a few seconds, I took a minute or two and
looked at the silky bed sheets and then at her dresser.
I looked inside it but then decided to just head back
down.
She was on the couch and had opened a bottle of
wine. "Come to me sweetie. We're going to have a
lazy evening and drink too much wine. There's a tray
of little appetizers I'm reheating in the oven just to
give us something to bite. Now come here."
I went and sat by her. It was awesome. She and I
drinking wine, relaxing on the couch and just hanging
out with each other like there wasn't anyone else she
wanted to be with. Ten minutes later the oven bell
went off and I got up and put the appetizers on a
plate. There were a lot and I brought them over.
But as I was setting them down, she asked one of
her questions again. "Stevie, darling, I am wondering
something. You can tell me honestly, Stevie. Janie
said you should eat her and I wondered if you had
ever done that before? Now before you fly off the
handle, this is just private talk between friends. I
know a lot of men don't and I think you probably
never have, have you?"
I just stared at her for a really long time. Sometimes,
she seemed crazy. Did she want to embarrass me? I
mean it was really personal and not the thing you ask.
I guess she was a little drunk. Maybe that was it. Of
course I hadn't. I wanted to but I didn't ever have a
girlfriend where that was possible. I just wasn't
experienced so I admitted it. "Yeah, well I haven't
exactly done that. I mean I don't really remember
every date I ever had but I think I probably didn't get
around to that."
She giggled. "You'd remember my cutie. I guess a
man never really does that right away. He needs some
help."
But then she was looking thoughtful and sort of far
away in thought. "A man learns when someone shows
him. A teacher is what a man needs. He needs
someone who, for his own good, shows him what to
do. A good teacher does that." She didn't seem like
she was talking to me. It was more like she was just
talking and I happened to be there. She wasn't even
looking at me.
 I didn't want to keep talking about not being
experienced so I dropped it. She kept drinking wine
and I was drinking the glass she gave me and eating a
lot of the things she made. It wasn't dinner but I
wasn't super hungry anyway.
She pulled off both her shoes and stretched out her
legs which I almost had to stare at. I liked her legs a
lot. She could probably figure that out too. But pretty
quickly she got up and said "be right back." I heard
her go upstairs and knew she would change.
She came back down wearing a nice silk robe but it
was long. I liked her short ones better but I guess the
leg show was over. She sat down and started flipping
TV channels. Finally she stopped and shut the TV off.
She took a very big drink of wine and then turned to
me. "Stevie, I know we're friends now and your
mommy told you to help me when I need it. You've
been a wonderful helper but I can't forget that I was
and I still am your teacher. And I'm also really
embarrassed about what happened today with Janine.
But I have a solution. Stevie, sweetheart, will you
trust me?"
She looked so serious and so concerned, I didn't
know what to say. But of course I trusted her. "Mrs
Wentworth, of course I trust you a lot and I know that
I have learned a lot just talking to you so whatever
you say is okay with me."
 That made her happy, I guess. She then turned on
the couch and whispered. I don't know why she was
whispering. No one was watching but maybe she was
nervous. She put her feet up and bent her knees and
parted her legs. I could see a pair of white silk panties
covering her as her legs got wider. All I could do was
look at them in awe. She didn't mind.
"Stevie, darling, we're going to begin a lesson. This
is just a lesson. It's perfectly clinical, that's all.
Intimacy like this would often happen when your
partner was not clothed but I'll leave these very thin,
sheer panties on so you know we're just studying and
learning. Now I want you to bend over and gently
kiss my thigh near the panties leg hole. This is how a
man starts to orally please his partner."
I didn't believe this was happening and I didn't
speak because I was afraid I would mess things up. I
just followed.
I leaned in and kissed and licked gently all the way
to the edge of her panties. I liked the way she
smelled. Her smell was very strong and like a unique
kind of perfume.
By this point she had both hands on my hand
caressing the back of my head but one was gently
pulling me up further. "Now place small kisses up
and down the front of the panties. Yessss, just like
that. Now stop up here and spend a few minutes
kissing." Her panties were soft and a little wet but just
a little.
Her legs were a little wider and her speaking voice
was breathier, like she was having a little trouble with
her breath. "Stevie, that's a woman's clitoris.
Sometimes it's easier to notice a woman's clitoris
when I'm excited. It's very sensitive even through my
panties so be gentle but your partner will like the
attention you pay here."
I was trying to follow her instructions carefully but
it also made sense just to kiss and lick gently and
make sure she was responding. I knew she was
teaching me but I thought that getting a real response
would happen if I was doing it right.
She wasn't talking as much as when we started and
her hands on my head were holding it tight, almost
pulling my hair. Her body didn't stay still which made
it harder but I think it was because she was having
fun too. Sometimes she would talk between gritted
teeth: "yes, Stephen, OH, right, yes that's what I
meant." Other times, she wasn't very specific: "yes,
oh yes, thats a good idea."
She had loosened her grip and I lifted my head to
just look a bit and her back was arched backward
which made it hard for her to see what I was doing.
Also her eyes were closed but I think she could feel it.
 Her panties were even wetter which I could feel on
my chin. It was then that I figured out that arousal
makes a woman sometimes get wet. Mrs Wentworth
wasn't really speaking anymore, just making noises
and moving around.
Suddenly, I felt her body shaking and her legs
twitching and heard a muffled sound from her head
but I didn't want to stop tasting her. It wasn't long
after that though that she pulled on my head and
pulled me off her and slid me up so I wasn't doing it
anymore.
She held my head and seemed to be catching her
breath. I was pretty sure she had an orgasm even
though she was just teaching me. Actually her orgasm
made me feel better than almost any part of it. I got a
lot of pleasure inside just from knowing that I had
caused an orgasm in her no matter why it happened.
After a while, she moved back to her old position
and sat back up on the couch. I figured she would
have to go upstairs and change again but she didn't
leave.
A few minutes later, she didn't look at me became
all teacher-voiced again and said, "anyway, so you
can see that if you happen to be with a woman
sometimes and she has some interest in something
like that you'll know what to do. You can see why it
was very naughty of Janine to suggest something like
that today. I don't know what she was thinking."
I wasn't sure what would happen next so I just said,
"Yes, it was very surprising and not right of her to ask
that."
I wanted to be grateful but wasn't sure what to say
exactly so I added, "Um, thank you for the lesson for
me though." I wasn't sure what to say next because I
wanted her to know how much I enjoyed doing it for
her but not if she would think that was weird.
She finally turned to me and smiled and said "you're
just the sweetest young man, aren't you?" And then
she leaned over and kissed me. It was nice. Not too
quick either which was sort of funny because I bet my
mouth kind of tasted different because of where it had
just been.
I stayed pretty hard the rest of the night but all we
did was talk about other stuff, finish the wine, and the
appetizers. She kissed me goodnight, got up, walked
into the laundry room for a second and then to bed.
"Night night sweetie."
It wasn't late but I was actually pretty tired. I walked
by the laundry room too about fifteen minutes later. I
went in and found she had left the panties she was
just wearing on the top of a hamper in there. I could
tell because it was open and they sort of hung on the
edge. I couldn;t help myself and grabbed them. They
were still wet, obviously. I wasn't about to jack off in
the laundry room so I slipped them in my pocket and
went upstairs.
Mrs Wentworth's door was open because she has
that open door policy, as she calls it. I put my head in
and said good night. She was already in bed and said
"night night, Stevie. Thanks you for taking care of me
today. I hope you get to sleep easily."
I changed pretty quick and got under the covers and
masturbated right away. The panties were my
inspiration. The open door rule made me be nice and
quiet as much as I could so she didn't hear. But I
came pretty fast and the panties reminded me of the
new amazing that happened and all the amazing
things that had happened all day. It was a wild day
and I fell asleep smiling and looking forward to the
next day.
Mrs Wentworth Enjoys Act Three
This is the sixth part of the Mrs Wentworth series
and comes right after "Mrs Wentworth and a Useful
Lesson." You can find the other parts by clicking on
my name. I'm enjoying writing this and a lot of the
responses I get from people. I do reply to all
feedbacks that have a reply in them and I read all
comments. A lot of people have been very helpful in
helping me think through things and sometimes in
coming up with ideas for this or other stories so thank
you. P.S. The next episode is almost done too but I
wanted to end this one at the spot it ends.
The next morning I woke up slowly. I still had the
panties from the night before under the sheets and
they helped remind me of what had happened. I had
enjoyed licking Mrs Wentworth more than anything
that happened since I came to stay for a little while.
But I couldn't help being confused.
Mrs Wentworth was a mystery to me. Sometimes I
thought I understood her and sometimes I had no idea
where she was coming from. When my mom made
me come and stay with Mrs Wentworth, I was pissed.
I'm almost 19, a fully grown adult. I don't need
someone to watch me. But soon I realized it wasn't
like that and that Mrs Wentworth wasn't just some old
lady. She wasn't really that old but she was more than
twice my age. But I really liked her. I thought she was
nice and I guess I liked her more than that.
A few sexual things had happened since I got there
and last night was the best. But I wasn't sure what it
meant. I know I'm not the most experienced person so
I'm not always sure but sometimes Mrs Wentworth
seemed like two different people. Like the one night
she actually gave me a blowjob I thought was going
to change everything but she acted the next day like
nothing happened. Like she was two different people.
I was hard already but decided not to start the day
by cumming in her panties again. Instead I got
dressed and went downstairs. I walked by her room
and she was already up, the bed made, and started her
day.
I got downstairs and she greeted me with a big smile
and a "good morning, my sweet Stephen. Did you
have a good night?"
I wasn't going to be the first one to mention the
night before so I played it cool and just said "oh yeah,
I slept great. How about you?"
She smiled and said "I had very sweet dreams.
There's coffee just made and bagels on the counter."
I made myself a bagel and decided to take charge at
least a little. The morning is normally when she might
ask me something embarrassing and show up my lack
of experience. Not that I admitted to anything but she
could probably tell. Today, I decided maybe I'd take
charge or at least keep her from going there.
As I started eating I said, "So, Mrs Wentworth, I
want to ask you something."
She just leaned eagerly and said "oh ask me
anything, sweetheart. You know I want to help you in
any way I can and teach you and answer any question
even the kind you can't ask your mommy." And she
smiled very sweetly.
Damn. She threw me off again. When she refers to
my mom like that it makes me feel nervous. But I
decided to go ahead and learn more about her. "Okay,
Mrs Wentworth. I know you always ask me stuff like
what kind of things I've done or like to do or
whatever. But what about you? I mean I don't really
know a lot about you. Like, are you really that
experienced in things? Your friend Janine sure didn't
think so."
There I'd said it. Not as forceful as I wanted but I
put it out there.
I'm not positive but I think she looked a little
nervous. Maybe nervous is too strong a word but she
sure didn't answer immediately. She took her time.
She took a slow drink of her coffee before looking at
me. "Stephen, what an interesting question. I'm not
positive exactly what you want to know and why you
want to know it. I suppose I am not as experienced as
some people but it depends what you mean. Surely,
you don't want me to list in detail every sexual
experience I've ever had in my lifetime. I wasn't
married for very long but it was a few years. I'm not a
virgin, Stephen dear, if that's what you're wondering."
She looked at me with a smile on her face but it was
different from her previous smile.
I was a little more nervous but I really wanted to be
more forceful and not just let life happen. I kept going
but was maybe a little bit more nervous than I had
been. "I didn't mean I wanted a list or something. I
just meant that, well, I thought I'd ask." Then I
remembered Janine and realized she hadn't answered
that part and I felt more confident. "You know, Mrs
Wentworth, I was thinking about Janine. Janine said
that you, well she indicated that you were a prude.
Not that I think you're a prude, " I added quickly. "It's
just she seemed to mean that you weren't all that
experienced.
Mrs Wentworth took her time. She had frozen when
I brought up Janine and looked bothered. Then when I
said prude I knew I crossed the line. Now she seemed
to be moving slowly on purpose and getting herself
together.
"Stephen, I'm very surprised at you. I'm not hurt
because I don't think you mean to be hurtful. There's
nothing wrong with being inexperienced. Maybe your
own lack of experience is bothering you but it
shouldn't. You're only 19. I know you're an adult but
experience takes time of course. Now, I certainly
don't have the same level of experience as a
prostitute! No, no, I know you weren't suggesting
that. Do I seem to you like I don't know what I'm
doing?"
She looked at me, waiting for an answer. Her look
wasn't suggestive. It didn't say anything. I knew and
she knew that we had done a few things together even
if we didn't talk about them but her look clearly said
she wasn't going to mention them but I could if there
was a problem. Suddenly I was super nervous again
and had lost all the initiative. I was also upset because
I worried that I had come across as mean and I
realized that I didn't want to hurt almost more than I
cared about being hurt myself. My feelings were that
strong.
"Oh, no, Mrs Wentworth. I didn't mean to imply
anything. I was just making conversation, really."
She smiled. "I understand, Stevie, dear, why you
might be thinking about Janine a lot. That's what she
wants. That's why she was flirting with you. Some
women are like that."
I was thinking that Janine's actions were some kind
of flirting. At this point, Mrs Wentworth, though, was
calm and in control of the conversation.
 Now she leaned across the table and grabbed my
hands in hers. "Sweetie, you know it's okay. Janine is
a little lonely and sometimes she lashes out and says
things. We don't mind though because she's our friend
and we understand. Now, I'm sure you don't think I'm
a prude do you?" Then she looked into my eyes until I
shook my head.
"Good. This conversation has taken a lot out of me
so I think I'll get dressed unless you have something
else you want to say? No? Good."
She stood up and went upstairs and left me feeling
like a jerk.
I waited a couple minutes but I realized I needed to
apologize. I just was acting crazy because I really
didn't know exactly what was going on. I went up and
knocked on her door. It was open because she had the
policy about never closing doors.
I looked in and said "Uh, Mrs Wentworth?"
I heard a voice from the closet say, "what is it,
Stephen? Do you have more questions?"
She came out with a hand on her hip and looked at
me. She was getting dressed. She had a blouse on and
was dressed on the top but hadn't put a skirt on yet.
Her blouse was long but it was still really sexy. I tried
not to stare.
I said, "I'm sorry, Mrs Wentworth. I feel like a jerk
and want to say I'm sorry. I don't know what I was
saying this morning and I feel bad about asking what
I did and how I did. I'm really sorry."
She immediately changed into a different person.
She smiled as a big a smile as I've seen and came over
and hugged me. She squeezed me incredibly tight and
I could feel her soft breasts and cleavage pressing into
me and her bare legs. I was hard but I didn't care
because she felt better.
"Oh, Stephen, you sweet little man. I'm not mad but
it means so much to me to hear you say that. Now
let's not even think about it anymore. You didn't mean
anything and no one cares anymore. I'm not even
thinking about it. We will just get on with things and
have a very wonderful day together."
She let go of me and turned around, picked up her
jeans and slipped them on. It wasn't really that risqué.
I got a quick glimpse of the black panties across her
butt as she pulled the jeans up the last foot but only a
glimpse. Then she turned around. It was actually kind
of a casual sexy look. Over the jeans she had a long
white shirt, almost like a men's dress shirt. It was a
little thin. I know it was thin because underneath it
she had a black bra and it almost showed through. It
showed through enough I could tell it was there.
I think I was staring because she was smiling. I
think she secretly liked to draw my stare. "Come,
now, Stevie. I need some help making he bed. I hope
you'll be a good helper today."
"Of course I will." I grabbed the one side of the bed
and started to help. I wasn't much for chores but I
liked making her bed. Plus she had cool slippery satin
sheets I hadn't noticed before. I liked watching her
bend over but the slight cleavage wasn't even as sexy
as just seeing the black bra making itself known
under the white shirt. It was a sexy look.
She smiled at me and said, "do you like my sheets,
Stevie, honey? I don't know if you like rubbing your
hands up and down on satin like this but think how
nice it feels to have your whole body in satin all over
you and all around you. I'll have to let you try it out
sometime."
I rubbed my hand over it and said "I'd like that
sometime." Maybe she meant the sheets but in my
head I wasn't thinking about being in them alone.
We finished making the bed which was good
because too much more time with satin sheets and
staring at Mrs Wentworth wasn't good for the
tightness of my pants.
We went downstairs and I helped her with a few
things but she reminded me that we had to get ready
to go out before too long. Of course I had forgotten
that we were going anywhere.
 But she also mentioned we really should call my
mom. I don't know why but I kept forgetting my mom
was out of town. It's not like I called every day and I
guess part of me would have expected her to call me.
She never remembered and we called her. Which was
fine.
I sat in a big chair in the living room and waited
because Mrs Wentworth always talked first. She
whispered to me to be quiet as she dialed. Then she
sat on the arm of my chair and turned the volume all
the way up so I could hear almost everything. And
she giggled while it rang like we were doing
something secret instead of just calling my mom. But
it went to voicemail.
Mrs Wentworth looked annoyed and dialed again
right away. The third time she answered and Mrs
Wentworth said "Hi hun, it's me Doris. Remember me
and your son back here while you're off in Vegas?
Yes, yes I know it's business." She looked at me and
rolled her eyes and stood up.
Mrs Wentworth walked in a circle while she talked.
"I know. It can be hard to hear the phone sometimes.
Are you OK? You just sounded funny that's all." The
she came and sat on my lap. She held a finger up to
be quiet but turned the phone so I could hear most of
it.
 I was distracted by having Mrs Wentworth on my
lap. It doesn't sound like much and it wasn't sexy
exactly but it was warm and close and it made me feel
close to her. I also always liked being close to her and
feeling her body touching mine. That doesn't make
me a pervert. It just means I had strong feelings.
But on the other end of the phone, mom did sound
odd. She was distracted, not saying much, and
breathing funny. I could hear mom talking about just
killing time between work things as she called it. Mrs
Wentworth asked if she was alone and mom said of
course she was. It was probably just the TV but I
don't think she was alone.
Mom didn't ask about me that I heard but Mrs
Wentworth said "Stephen is in the next room, let me
go get him. She shushed for like ten seconds and then
handed me the phone saying a little loudly (even
though we were in the same chair) "Stephen, it's your
Mommy. She was asking about you."
While I was on the phone, Mrs Wentworth didn't sit
still. I guess she wasn't comfortable so she kept
squirming to sit right. That can be very distracting
and sexy which dangerous when a woman is sitting
on top of the part of you that gets hard.
Mom on the other hand didn't say much. I did most
of the talking and she just breathed heavy. She might
have just been tired but I actually think she really did
have someone with her and they either were doing
something or had just been doing something. She
didn't moan but she sounded like she wanted to. That
might have been my imagination.
I'd have talked more to find out but Mrs Wentworth
reached down and squeezed my bulge in her hands
which is also very distracting. She didn't say anything
or make faces but she squeezed three times and I sort
of ignored the phone call. Not completely, I mean I
still sensed my mom's weird breathing. I didn't think a
lot about it though. She said almost nothing. Which
was fine. I had never really been on my mom's mind
ever really.
She said "Okay, be a good boy for Doris and I'll see
you when I get back. I'm not sure when that will be
yet. The situation keeps changing here."
I said "Okay, see you when you're done. Bye." And
that was it. Mrs Wentworth took the phone and got up
and put it back in its charging station. She was
shaking her head and saying something under her
breath.
I asked her what she said but she just smiled.
"Nothing. I'm talking to myself. Now I need to get
ready. It will take me a while and then we have a very
long drive. I made dinner reservations so we can eat
first this time. I think that will help."
 Then she went upstairs and I realized I had forgotten
we were going back to the opera and to dinner first.
That would be good. The first time I was worried I'd
hate it but I realized how much Mrs Wentworth liked
it and I didn't mind. The music was okay and the
whole event was sort of fun and formal. Plus she was
really great looking dressed up like that.
It always took her a lot longer to get ready but
eventually I went up to change my clothes. I looked
in her room because the door was open but didn't see
her. I went back to my room and was going to decide
what to wear when I discovered it was all laid out
already. I guess she got it ready which was cool. It
saved me worrying what I should wear.
It was what I thought of as typical for the opera
now. It was a nice gray suit, one I'd worn already, and
another new tie. Everything else you'd expect
although I noticed she laid out boxer shorts for me. I
usually wore briefs but these were silk so I guess
they're considered more formal. Actually I liked
them.
I still got downstairs ahead of her even though I
shaved first too. Eventually she made it. I'd seen the
dress when she bought it the other day but it looked
awesome. It wasn't real tight but it was nice and she
looked awesome in it. When she got down, she
smiled and said "Can you put the suitcase over there
into the car? I packed a few things in case it got late
and we decided we had better stay in the city instead
of trying to drive all the way home. It's just in case."
I put it in the car. Last time I didn't even know about
it. I thought maybe we could drive home anyway but
I had enjoyed staying over the last time so I hoped
maybe we didn't.
I came back in and she gave me her arm. "Good
evening. Shall we go?" She got formal and I
remembered it was a date and she was teaching me
about dates.
So I took her arm and moved her toward the car
saying, "allow me to escort you miss." I know it
sounds weird but she loved it.
It was cool that I got to drive. Remember I love the
car. I concentrated on the road but I also enjoyed how
she sat with a lot of leg showing. She had nice legs
and I like women's legs anyway. I think she knows
that and was teasing me on purpose. It wasn't a bad
kind of tease but a friendly one. Almost like a reward.
On the way down, she turned and asked me real
seriously "Stephen are you OK about your Mom?"
I wasn't sure what she meant. I didn't really think
about my mom. We had one boring conversation and
mom doing who knows what on the other but not
talking to me but that wasn't really new. So I just said,
"yeah, I'm sure she's doing okay and I'm happier here
than I would be there. So, no problems."
She had this concerned look but seemed okay with
my answer. "I'm sorry we called her now. I guess I
didn't think that she would be like that. It doesn't
matter. You did what you had to do and now we'll
forget about her and whatever it is she's doing. I'm
going to have a lovely time with my date tonight and
not think about anything but having a nice night out
with a charming, handsome man that will make all the
other ladies jealous."
By the time we got downtown, we were both in a
great mood. She had a special way of making me feel
great.
She had me park at the parking garage that was
attached to the hotel we stayed in last time and also to
the opera theater. But we didn't go to either place. We
walked outside on the city street around one block to
a small restaurant. It was a small place, dark, fancy,
and very quiet. The waiters and waitresses weren't
friendly exactly but they were helpful like a servant in
a movie.
She helped order because I wasn't completely
familiar with a lot of the food. But I had a beef dish.
I'm not much of a wine drinker but she wanted a
bottle so we had it. It was good that the drinking age
had been lowered to 18 a few years before this.
 It was actually great. It was formal but very elegant
and adult, of course. A nice formal dinner in a
restaurant before the opera is the way it should be.
She had more of the wine than I did but I had a
couple glasses. The food was amazing.
She was happy and I was happy and the night had
just started. She kept reaching over and squeezing my
hand when she would tell me something. I liked that.
She told me two or three things about how to handle
your date, what women liked to talk about, and all the
little things you don't think about but make you
nervous.
Then she wanted to stop. She held up her hands and
said "enough about that. I'm going to stop being a
teacher. It's just you and me on a date having a nice
time." Then she smiled, grabbed my hand again, and I
also felt her foot which must have been out of her
shoe, playfully tease my ankle. It might have been
playful but I liked it a lot.
She told the waiter we couldn't stay for dessert
because we had tickets to the opera. He was
impressed and said something about the show they
were doing. I guess they got a lot of opera fans and
one night the star had come by.
I helped her walk. Not because she needed it but
because it was the way things are done. A lot of men
were walking their wives or dates on their arm. I
think I was one of the younger men there though. In
fact a lot of them were older, like grandfather aged.
That was okay with me though. It made me feel
better. I didn't feel young and out of place. I felt like
this was truly a date and Mrs Wentworth was treating
me like an adult. That's how she thought of me.
We walked up red carpeted steps to the foyer. Like
before I occupied a spot and looked around at the
arriving people while Mrs Wentworth went to the bar.
She came back with champagne for both of us. She
told me before that champagne at the opera is a
tradition.
We drank champagne and watched everyone. I
didn't see the people from before but I bet almost no
one goes twice in a week. For five minutes we said
hello to some couple passing by. The man looked like
he was easily 80, very skinny and not very tall really.
The lady was a little younger, maybe in her seventies,
but very made up. She was four inches taller than him
and a little bit heavy like he was skinny so opposites
sort of. Her makeup was almost like a layer of paint
but while she didn't carry herself like Mrs Wentworth,
she looked nice for her age. They were very nice to
both of us too.
At one point the man, George took Mrs Wentworth's
hand in his and raised it up and then kissed it. At the
same time, his wife Kitty held out her hand to me. I
was glad George moved faster because I didn't know
at first what to do but I followed his move and kissed
Kitty's hand. They talked for a few minutes and then
went to beat the crowd to their seats. Kitty kissed me
on both cheeks which was old fashioned and formal.
At the same moment, she reached behind and pinched
my butt which wasn't old fashioned.
Mrs Wentworth teased me about it so she must have
seen it. "I think she wants to take you home and keep
pinching you Stevie, dear. I'm glad they left so I
didn't have to slap her to keep her hands off you."
And she laughed and I laughed too. At that point the
lights flashed which is how they tell you to start so
we went in to find our box and sit down.
We had the same box as before. Mrs Wentworth
scooted right next to me and whispered "aren't you
glad I got our usual box, sweetie?" Then she handed
me the opera glasses and said "I know you need these
to keep an eye on La Belle Sofia and her lung power".
She was teasing me like last time that I was only
using the small binoculars to stare at the lead singer
and her impressive cleavage.
I blushed and tried to protest. "No of course not. I'm
not just staring at women."
She squeezed me close to her, our chairs almost
touching. "I'm just teasing my date tonight."
 The music was nice. I'm not a huge opera person but
I actually enjoyed it with her. And she enjoyed being
right against me. About halfway through the first act,
she grabbed my arm and whispered "there are George
and Kitty right below in about the tenth row." I
looked down and alternated between having my opera
glasses focused on the lead singer and on Kitty. I also
looked around the audience.
I enjoyed the music more than people might think
but I would also got distracted and found looking
around kept my interest more. Give me a set of small
binoculars and a spot above the rest of the audience
and it helped pass the time. I'm not a total pervert or
anything but looking down from that angle and all the
women had cleavage. Some of them were more
interesting than others too.
It was funny. Kitty's cleavage was more interesting
because I had met her. I don't know why that helped
but it did even though she was a lot older than me and
a lot older than Mrs Wentworth too. But I looked
around a lot. Mrs Wentworth was keeping very close
to me too. If I looked over at her the right way I could
see down her front when she leaned forward a little
but not when she leaned back. Also her dress wasn't
really short when she was standing but when she sat
and then crossed her legs it came way over her knee.
Her leg also kept bumping me because the wall at the
edge of our box was right there and the chairs were
set up closer to it.
When the first intermission came, we went back to
the lobby. Mrs Wentworth was very happy. She put
me by the post we always stood by and said
"champagne time! You guard our spot while I get us
drinks." It didn't take her long and she came back
with glasses for each of us.
"Tell me, my darling date, are you having a
wonderful time? Isn't this opera delightful?"
"Well, yeah. Actually it's pretty good. I like the
music anyway and all the people. It's an event."
She smiled. She was very happy. "I saw you spying
on your new friend Kitty and the rest of the audience.
I think it's cute but don't forget you're all mine." Then
she laughed and I knew she was joking.
Actually, George and Kitty came up soon later.
They were very nice still. George didn't move very
fast. We talked about seats and they were excited to
hear we were in a box. Kitty said, "Oh we used to
always have a box. I liked to stare down at the people
from above and it can be a nice friendly place in the
dark up there." She smiled at Mrs Wentworth. "Now I
guess we're the people you stare down at from up
there." Then she looked at me with a wink and said
"Row H, seat 14." And then she poked me.
 She was kidding around and fun. I think Mrs
Wentworth liked her too. It was a fun part of the
opera for me that we got to know people who were so
different. Mrs Wentworth just said "I know the steps
up can be difficult, but we do like the peaceful
atmosphere up there."
We talked some more and Kitty said, "Lana, are you
and Stephen married by any chance?"
I noticed that Mrs Wentworth was going by Lana
again tonight. I liked it when she did. But I almost
laughed when Kitty asked if we were married. At
first, I thought it was just silly but then I thought more
and after all we were on a date. And it at the opera so
you might think anything really.
Mrs Wentworth put her arm around my waist and
said, "oh no, we're not married yet. Things aren't that
formal between us right now. You know how it is."
I wasn't sure what that meant or why Kitty was
asking. Just conversation I guess. She was still teasing
us a little bit I guess too. "Well you better keep a
close eye on him if he's up for grabs." She laughed
and reached over and pinched my butt.
I was surprised with George right there and Mrs
Wentworth right there but I guess because she was
older everyone thought it was just teasing and she got
away with it.
 At that point they left to get back to the seats.
George did look a little unsteady. But Mrs Wentworth
turned to me and laughed. "Isn't it funny that she
thought we were married? I thought it was cute."
Then she took my arm in hers and added, "I'm sure
she would be jealous though if such a handsome man
were my husband." And then we headed back to the
box.
Maybe it was weird but I liked it and I liked
everything she said. "I know it was sort of funny. I
guess if we were married, one of us would have a
wedding ring. I noticed she had one."
We were about to sit down but she stopped walking
and teased me. "Stephen, were you checking out
Kitty? I didn't realize she was your type. I don't want
to stop you. And I'm sure Kitty isn't the sort of
women who would let being married stop her if she
had her eye on you. Maybe you think I am better
suited for George."
I knew she was teasing but I was a little upset I
guess. "No, no of course not. Mrs Wentworth, I didn't
mean to imply anything. And I definitely wasn't
checking Kitty out. I mean I'm here with you and I'm
not like that at all. And George is definitely too old
for you!"
She grabbed me and held me tight as we sat down.
"Don't forget you have to call your date Lana. And
don't worry. I'm just teasing. Lana is very happy to be
spending her evening with Stephen. As for George, I
think age is just a number. I don't worry at all about
the difference in two adults ages. Although the men I
date tend to be younger than me not older." And as
she said it, she kissed me on the cheek.
I felt a little embarrassed and a little excited. But the
music was about to start so I looked to the stage and
got our opera glasses. Mrs Wentworth was leaning
forward watching but then sat back, crossed her legs
and was much more relaxed, almost sleepy even. I
stared at her legs as much as I could safely but also
scanned the audience.
I had five or six people I liked to stare at and even
into some of the box sections on the other side. I liked
looking at Kitty some because I knew her now. She
was also sitting differently so I had a better look at
her. She also knew where we were so sometimes she
would look up at us. One time she put her hand right
against her neck and wiggled her fingers toward me
which was funny, a wave just for someone peeking
through opera glasses.
In the meantime, Mrs Wentworth was very relaxed.
She wasn't sleeping but her eyes were closed so I
could look. There was no doubt she looked beautiful
and that her legs were enough to make me forget
almost everything else. She woke up or became more
alert right before intermission. On the way down the
stars she pinched my butt twice.
She also very quickly got us champagne. Kitty made
right for us and she and George got there as we had
started our champagne. She sent George to get
champagne while she went to the bathroom. Mrs
Wentworth handed me her glass and went with Kitty.
When George got back eventually (he was a slow
walker) we made small talk while we waited. He
didn't say much and was hard of hearing but very
nice.
Kitty stood right next to me when they got back and
drank her champagne pretty fast. "Lana, I have to say
that you and your fiancé are the most fun people
we've met here in months. I'm sorry there aren't any
more intermissions to get to know you more before
we head back to the hotel when things are done. We
usually stay over. Have you two ever done that?"
I wasn't sure what to say but Mrs Wentworth
quickly said, "we never have a firm plan and we often
just head home but once in a while we stay over. I
don't know what we'll do tonight. Stephen never lets
me know until the last minute." And they both started
laughing. Of course she was making it all up but I
went along.
 The lights flashed and they had to hurry because
George was a little slow walking. But Kitty smiled
and said "I'll wave from down below."
And we went ourselves. Mrs Wentworth always
finished her champagne even when I only had half. I
think she was having a nice time. As we walked back,
she pulled my arm around her. She said it was to help
her up the steps. My arm was on her waist but she
stopped and then whispered in my ear "a little lower
this late in the evening. Your date won't mind."
I wasn't sure if she was teaching or just talking
about herself but I moved my hand until it was on her
butt and sort of half-squeezed as we walked into our
box. We sat and she asked me "Stephen, at the
movies do you ever kiss your date if the movie's slow
or it's nice and dark?"
I was embarrassed to answer but she said
"shhhhhh." and then put her lips on mine and kissed
me softly, like at the end of the night on our first date.
I opened my lips slightly and kissed back. we kissed
like for a couple minutes and I felt her tongue teasing
my lips too. She paused for just a few seconds to say,
"this is the kind of kissing I was asking about. I
wanted to know if you did this."
But she wasn't interested in an answer. She kept
kissing and I tried to keep up, doing what she did.
Soon our tongues were twisted together exploring
each other. My hands were on her back holding her.
Her hands were rubbing my body so mine followed. I
could feel every seam of every piece of clothing she
had on under her dress. That's a very erotic feeling.
And when I felt her hand in my lap caressing my
throbbing bulge, I pretended it was natural and
exactly what I was expecting. I waited a few minutes
and found her breasts. I caressed them but softly. I
found that her nipples were very hard and obvious
even though her layers of clothes. When I touched
and pulled on them, pinching them through the layers,
she let go of my lips and made a very erotic sounding
groan.
She pulled on me and pushed me out of my seat so I
would go on the floor. The opera was going but it was
just background music for her right now. I knew what
she wanted and it was exciting. As she opened her
legs, I positioned between them and she pulled her
skirt higher.
I felt her hands on my head pulling me and I started
to lick her through her very wet panties. Her hands
were on my hair but not directing me, just holding
and gripping. My tongue raced up and down her
front, finding the sensitive places, paying special
attention to her clit like she had taught me.
She would squeeze me every few minutes, clamping
her thighs on my head and squeezing me between
them. I was part worried that she would scream out
loud but I also didn't care about people hearing. She
didn't scream but one hand pulled aside her panties to
give me better access.
After that it was only a few minutes before she
started shaking and I knew she as having an orgasm.
In the middle of her convulsions, she bent forward
and kissed the top of my head but pulled my head
away so I'd stop licking. We stayed like that for a few
minutes before she sat up straight and fixed herself.
I got back up into my chair and it was only a few
minutes before the opera was over. She leaned over
and kissed me on the lips and all over my face.
We took two steps toward the hallway behind the
boxes and she whispered, "I love the opera."
Mrs Wentworth Enjoys the Nightcap
This is part of the continuing Mrs Wentworth series.
It comes after "Mrs Wentworth enjoys the third act."
The series is a little slow for some people (in the first
six chapters, the two main characters didn't actually
have intercourse and it isn't clear yet what Mrs
Wentworth's intentions are, maybe not even to her).
Some people like slow and teasing, some don't. I
always appreciate comments and always reply to
anyone who comments in "feedback" with a way to
reply. The ideas of many readers have been helpful
for this and other stories too so thank you.
When we walked out of the box we had at the opera,
Mrs Wentworth was very happy and kissed me and
said "I love opera."
I think she was also happy from all the wine and
champagne and maybe because I had just spent the
final act of the opera on my knees between her legs
bringing her to an orgasm. I don't know how it
happened. I don't think either of us planned it. I bet
she didn't even think that our pretend date was going
to be anything real even though she did keep telling
me that she was teaching me and giving me advice.
I felt great too, though. The few times anything
sexual had happened between us, we didn't talk about
it. I thought partly because Mrs Wentworth was
almost like a different person when that happened and
by the time we could talk she had become her old self
again. But tonight, I didn't care and didn't want to
wonder why. I just enjoyed the mood and the feeling
knowing that my face was even still a little covered
with her taste.
We walked back to the lobby like we did for
intermission but this time the opera was over and
people were leaving. Before she had told our
intermission friends that we would probably go home
but sometimes we stayed over and we hadn't actually
decided. I wanted to ask what she thought but wasn't
sure how to bring it up.
We went across the walking bridge toward the
parking garage and the hotel. We didn't even talk
about a room. She just told me wait by the elevators
and went to get a key I think. I was glad.
When she came back, she was a lot calmer but still
very happy. I offered to go find the car and get the
overnight bag she had packed in case. But there was
no need she said, "Don't be silly darling, that was all
taken care of when we got here before dinner."
We got to the elevator and ran into George and
Kitty, our intermission friends. George looked older
as the night wore on. By this time he looked very
tired and I could tell he was in his eighties (or at least
that was my guess). Kitty on the other hand didn't
look tired at all. Earlier I thought she was 5 or 10
years younger than George. Now I would have
guessed a lot more. Still, she was probably in her
sixties but she was nice.
We talked to them as we got in the elevator. Well,
George didn't talk much but Kitty did a lot. She said,
"Stephen, it looks like your hair got messed up." I just
laughed because it's not like she could know why my
hair was messed up. Then she turned to Mrs
Wentworth and said, "Lana, I think we're going to go
to the room for a minute but then run up to the bar on
the top floor for a nightcap. The bar has a lovely
view."
Lana was the name Mrs Wentworth sometimes went
by when we were out even though her real name was
Doris. I was a little surprised but not much when Mrs
Wentworth said, "Oh, we might see you there.
Stephen likes that bar."
We got to out floor first and Kitty pinched my butt
as I was leaving. She'd been doing that all evening but
I didn't really mind. I just thought it was funny.
We walked and got into our room with me carrying
the bag. I put it on a table and then went and looked
out the big window. I wasn't as good a view as up top
but even on the 25th floor we could see a lot of the
city. Mrs Wentworth stood right behind me, actually
pushing against me a little, and whispered in my ear,
"isn't it a great view? The kind of thing that make a
girl feel romantic."
I really think she liked to whisper in my ear on
purpose because she knew it drove me crazy. But all I
said was "I'm glad we stayed over."
She grabbed my hand and pulled me toward the
door. "And since we're staying over, we can go to that
cute bar upstairs and not have to worry about
driving."
She pulled me along to the elevator then we went up
to the bar. The bar wasn't very crowded. I guess the
hotel wasn't that full and I'm sure the opera wasn't a
big part of their business. We sat in a nice booth right
by the windows. A whole wall of the places was
windows with an amazing view, even better than the
one in our room. I'm not sure we needed more drinks
but got us each a glass of brandy. I didn't really like it
but it is very sophisticated.
We were staring at the view when Kitty came up
behind us. I forgot she said they might join us.
She sat down without asking which was okay I'm
sure. She said, "just me tonight. George was very
worn out by the whole evening and he got into bed.
He gets tired very easily now."
Mrs Wentworth was very sympathetic and asked
about George's health. He had some kind of heart
condition. Kitty was saying, "Well, a lot of it is just
age. George is a lot older than me and that changes
some things. But that's all right. That's one reason he
likes going to things like this and meeting people.
Lana, he told me how much he liked meeting you and
to tell you how sorry he was not be joining us tonight.
Oh and he liked you too Stephen, I'm sure."
I laughed. I'm sure he was much more interested in
Mrs Wentworth even if he wasn't a dirty old man. "I
think he talked to um Lana more than me. I hope he
feels better in the morning."
She leaned over and squeezed my knee (I was in a
u-shaped booth between them) and said "don't be
jealous. I'm sure he just didn't appreciate your cute
butt as much as someone like me does" She laughed
but turned to Mrs Wentworth and added "Not that I
am stealing your man, Lana."
We were having fun and just talking. Kitty was easy
to get along with. At some point, Mrs Wentworth was
talking about relaxing and she said, "I like the dress
and everything I bought to wear with it. I like being
dressed up. A little part of me thought about changing
into something casual but Stephen was in a big hurry
to get up here so that answered the question for me.
I'm glad now because you didn't change either."
She smiled at me even though it wasn't true.
Kitty was having a great time and drinking as
heavily as Mrs Wentworth. She said "Oh, I didn't
think of changing. I didn't want to be late in case I
missed you and I was so looking forward to drinking
with you two. Besides my corset isn't a quick in and
out kind of thing." As she said the word corset she
lifted her breasts with her hands.
I didn't know much about corsets but her action
drew my attention to her chest. He breasts were lifted
nice and her cleavage was very good. I had been
distracted by it a few times all evening. Now that she
was calling attention to it I couldn't look away. I think
that might have been done on purpose.
Mrs Wentworth started to ask questions but I just
stared. I had had a lot to drink so I wasn't that careful
about my staring. But Mrs Wentworth said, "Oh, I've
thought abut a corset. Do you like it? I have to say it
is very flattering on you. You look beautiful."
Kitty said, "Oh, thank you Lana. That's very sweet."
She leaned closer to Mrs Wentworth which meant
much closer to me. They talked past me while Kitty
leaned forward and down showing off her stunning
cleavage almost under my nose. Kitty was whispering
now, "I love the way it holds me and takes care of me
and I think it helps me make the most of my assets."
She loosened a button. "And this little bit of lace at
the top, well some men can't keep their eyes off it."
Then she looked right at me and laughed.
 They both laughed and were looking at me. I was
embarrassed while they talked about the corset and
where Kitty bought it. Finally Kitty turned to me and
said, "Stephen, I'm so glad Lana was able to convince
you to stay over instead of driving home. George and
I were saying how nice it was to meet such nice
people at the opera. Most of the people are boring but
you and Lana seem so happy and energetic."
I wasn't sure what to say but I said, "Yes, we
thought the same of you two. Lana and I come often,
twice this week actually, and we really enjoyed you
guys." The way Mrs Wentworth was smiling, my
attempt to sound adult and cultured was working
pretty good. She looked very happy.
Kitty smiled and said, "well, I hope we can enjoy
your company again soon. Now they are closing here
so why don't you follow me and we'll leave." She said
it and then got up and left. Mrs Wentworth and I just
followed without thinking.
When we got the elevator, I said "I guess this is
good night then." As I said it, Kitty hugged me close
and then kissed me firmly.
Then we all got in the elevator, she pushed her
button and said "but you will both join me in our suite
for the nightcap we didn't have time to finish, I
insist." She looked Mrs Wentworth in the eye as she
held both her hands. "Just a quick drink and then you
can be on your way to do whatever it is you too have
planned."
We never really said yes but we got the elevator
with her and went into their suite. As we entered, I
noticed how big the room was. It was actually a few
rooms. A woman came out of a door and whispered
and smiled at Kitty. Then she went back into what
looked like a bedroom from the little I saw through
the door.
Kitty smiled and said, "That's our nurse. George
likes to travel with a nurse these days and it is
actually very helpful."
Mrs Wentworth and I were both looking around
amazed. I finally said, "wow, did get this just for the
night?"
Kitty smiled and laughed. "No, dear. We always
stay in this suite whenever we need to. Didn't you
know that this is one of the hotels George owns?"
"Wow, no I had no idea. I didn't know anything
about you guys. I just thought you were nice people
we met at the opera."
Kitty looked at Mrs Wentworth and smiled. "He's
very sweet and sexy at the same time. I can see why
you love him. Be careful or I might have to steal him
away." After saying that she gave me a hug and held
her body against mine longer than necessary.
 Mrs Wentworth looked funny but didn't speak. She
just looked at Kitty. Kitty went over closer and for a
minute I thought, well I wasn't sure. But Kitty seemed
to be coming on to me a little and I sort of thought
she was kind of coming on to Mrs Wentworth too.
But of course that was my very horny imagination
probably.
Kitty was speaking softly and saying, "Lana, were
you admiring my corset? You wanted to get one for
yourself too? Or did you want to borrow this one
from me? I think Stephen might like that."
Mrs Wentworth looked at her very directly and said
in a much stronger voice now, "No, I love the way
that looks on you and I would not want you to have to
take it off. But I do want to get one sometime."
Kitty took a breath and looked at Mrs Wentworth.
She ran one hand over here. I swear she ran a hand
over Mrs Wentworth's breasts but it was like I wasn't
there. The she rang a soft bell. The nurse we had seen
earlier came out and over to Kitty. She whispered
something and nurse left.
Kitty was suddenly very friendly and a little
different. She made small talk, poured us each one
last drink, and talked about the view and the hotel. It
was very nice after those few minutes of weirdness.
After about ten minutes, Mrs Wentworth stood up
and we all did too. It was time to go. Kitty grabbed
me and kissed me this time while also gripping my
butt tightly and even digging in her nails a little
through the pants. She kissed Mrs Wentworth on each
cheek and the nurse appeared. She handed Kitty a bag
which she gave to Mrs Wentworth. "I hope you two
have a good night's sleep. I'd love to get together
again with both of you. Maybe for breakfast if you
don't have to leave too early or we should plan to
have dinner one night before the opera. George would
love to see you again.
We thanked her and went on our way. We took the
elevator down to our room. Once inside, I said "that
was a little strange, wasn't it?"
Mrs Wentworth just said, "I think Kitty was being
very nice and enjoyed our company. With her age and
huge wealth she's just a little different from us
socially."
Then she opened up a suitcase. "Darling, I hope you
don't mind but I packed for both of us. I just thought
it would be easier."
Of course I didn't mind and I really liked it when
she called me darling. It felt like we were some
married couple but it felt mature and also
affectionate. And I realized now that I felt very
affectionate about her.
I took a couple of minutes and went into the
bathroom to get ready, brush my teeth and all that.
While I was gone she had laid out some pajamas on
the bed. She smiled and said, "now be a dear and get
into the nice jammies I brought for you while I
change."
Ok, I liked being called darling but I wasn't into my
clothes being called "jammies." But I put them on.
They were like the other ones. Dark red silk, very
expensive feeling. I also liked the way the silk felt
against me. Plus I was still a little hard and very
horny like I'd been all night. I put them on and stood
staring out the window. I loved the view. It better
higher up but it was still awesome where we were.
I didn't hear Mrs Wentworth come out. She snuck
up behind me and whispered "you look adorable in
your jammies, dear. Do you like them?"
I didn't turn around because she was pushed against
my back so she could see too. I just said, "They're
very nice Mrs Wentworth, thank you."
She said, "shhhhh" and turned me around. "No this
is still our date. You can call your date, Lana. Tell
me, do you like Lana's nightgown?"
She smiled and stepped back. I just stared. I loved it.
It was satin and the same color as my pajamas but
where mine had shorts this time, or boxers actually,
hers was down to almost the floor. It was like a sexy
gown but obviously for the night not for out. I just
said, "Wow, Lana. You look gorgeous. I feel like the
luckiest guy on the planet."
She turned around in it once and looked very happy.
The she paused and got serious and I got worried.
"Stephen I don't want you to be mad at me and I feel
terrible. I feel like you're probably mad at Lana."
I was confused. "What? How could I be mad? Lana,
I'm not mad at all. I'm having the best date of my
life."
She looked at me and pulled me over and we both
sat on the edge of the bed. "Stephen, that's right. This
is a date and we've discovered lots of things that
happen on a date at dinner and at the opera and the
bar. Stephen, my darling, Lana has been having a
most amazing time but I feel bad that I wasn't
thinking of you."
Now I knew. She must have figured out that I wasn't
a huge opera fan. "Don't think that way, Lana. I had
never experienced opera before and I admit I didn't
expect to like it but seeing you enjoy and being with
you made it all worth and I did enjoy it. But seeing
you enjoy it made me enjoy it more."
She turned and hugged me tight. In our embrace,
she whispered in my ear. "That's what I'm talking
about, my love. You made Lana happy. You thought
about me and I didn't think of you. You unselfishly
went down on the floor in our opera box." She was
describing something that had only happened an hour
before and reliving it made me excited again.
"Remember, Stephen? You were kissing Lana and I
got excited because you are such a very good kisser.
The you decided to go on the floor" I remembered her
pushing me down but I wasn't going to interrupt the
story. "And then your gently tongue made Lana have
a nice evening. I had a delicious orgasm, Stephen"
I knew all this but hearing her say it was very sexy.
She said it all into my ear without looking at me and
holding our bodies close.
She pulled her head back and looked into my eyes.
"Stephen, I feel so selfish. I almost thought I should
be spanked again." I didn't know what to say.
Her hand was between my legs. I realized I was
very hard and she was gripping me with my pajamas
around me. She whispered "get into bed."
I didn't need to be asked twice. I slid under the
cover and felt her turn the light off. The only light in
the room was a very dim glow from the lights of the
city reflecting through the window but it wasn't much
light at all.
She got into bed and started kissing me. At first
softly then with hunger. I felt her hand slide under the
shorts in the leg hole and stroke me while we kissed.
She rubbed her body against me. I kissed back and
felt her breasts through her gown. I enjoyed the
firmness of her nipples pressed against the satin and I
teased them.
She was unbuttoning the pajama shirt an kissing my
chest. Soon I felt her lips lower and lower. She kissed
my navel with the same passion she had used on my
mouth. I felt her hands pulling the shorts down and
freeing my cock from inside. She stopped for a
minute and looked up. "Stephen, Lana loves you."
The her mouth was on me. Kissing and licking my
throbbing cock, tasting the shaft, and then teasing my
balls with her tongue in an amazing way. It seemed to
last forever but it was probably only minutes. I
gasped and said, "I'm about to cum" and she pulled
her head back, gathered my cock in some of the
layers of her gown and collected my cum in her satin
folds. We lay there for a few minutes and she slid up,
putting her head on my chest and staying there with
me not speaking.
We were like that for ours. It was great. Sometime
in the night, she slipped, went to the bathroom and I
think cleaned up. She came back and we lay next to
each other all night.
The curtains open in wonderful in the night but they
make sure the sun wakes you up. As we awoke, Mrs
Wentworth said "stay there, I'll get this." She got up
and closed the curtains and went off to the bathroom.
 I lay there on my back thinking about the amazing
night and the amazing week it had been. I was laying
there in only the silk shorts because of everything that
happened. None of it as what I had imagined a week
ago.
Then I heard Mrs Wentworth say "Stephen, darling,
this date isn't over yet." And I looked and saw her
standing at the foot of the bed.
Mrs Wentworth and Stephen
This is the eighth part of the Mrs Wentworth series.
It comes right after Mrs Wentworth Enjoys Act Three
and Mrs Wentworth Enjoys The Nightcap. I think it's
more enjoyable if you have enjoyed the slow
development of the series. If you don't like slow
though, you won't like this. I am very grateful to
everyone who has commented publicly or sent
feedback. I always reply to feedback and appreciate it
even if critical. Advice has been very helpful to me so
thank you for it.
I was laying there in the morning, high above the
city, daylight streaming in and reminding me it had
not all been a dream. Just a week ago, I was annoyed
that my mom thought it necessary to have me, an
adult in every way, stay with her friend and my
former teacher (a long time ago) Mrs Wentworth. But
the boring old lady wasn't as old as I remembered and
wasn't boring. I was enjoying myself and growing
very fond of her. We had practice dates where she
was "Lana" and taught me things. We had sexual
encounters, not all the way or anything, but just the
day before I had eaten her on my knees at the opera.
And in the hotel she gave me the best blowjob I ever
had. I hadn't actually had many and my real life
sexual experience was not a lot but it was great.
 We shared a bed together, all night, in a hotel which
is so much stronger than you can imagine. In just a
week I had reached a point where I couldn't imagine
not being around her and wanting to help her and take
care of things she needed.
I lay there thinking of all that. Wearing only silk
pajama shorts she had bought. My top pajama got lost
in the night. Suddenly, I heard Mrs Wentworth return
from the bathroom. I had gotten used to her being
almost a different person in the morning. At night,
especially when we had a learning date, she was Lana
and was wilder and sexier. But the morning Mrs
Wentworth seemed to ignore or not remember even
what happened.
This morning, in a hotel, she had just come from out
of the bathroom and I heard her say, "Stephen,
darling, the date isn't over yet."
I looked up and saw her standing there, leaning
against the wall near the foot of the bed. She had
changed again but not into her regular clothes. It
turned out that Kitty from the night before had
actually given her a corset to try. It wasn't a full,
regular one that laces up in the back, not that I could
tell then. But it was amazingly sexy. It was red and
black and was satin. There were panties that matched
it, all of them shiny.
 Something about it sort of pushed up her breasts and
they were almost spilling out. They were covered but
pushed up and the fleshy tops of her breasts were
beautiful. The look on her face was very sort of
naughty and sexy combined.
I'm sure I looked shocked but she just said, "Lana's
not ready to go to breakfast." I loved when she called
herself Lana. It was always good.
She took a step and stood at the edge of the bed.
Then she pulled and untucked the sheet and fell down
to her knees. I looked down and saw her grinning still
before her head disappeared under the sheet. Quickly
I felt her tongue on my foot. I didn't dare move. She
licked my feet and sucked on my toes.
I know that isn't actually a sex act but I was amazed
at how incredibly exciting it was. I couldn't see her,
just a lump under the sheet but I felt her licking and
kissing her way up my leg. It was like a dream come
true. The only other time she had given me a blowjob,
she acted the next morning like it didn't happen but
today I thought I might get another one.
I felt her tongue on my thighs, her hands pushing
the leg of the shorts a tiny but higher. She wasn't
licking my erection yet but her face and hair were
crushing and stroking it. I felt her hair and face on my
belly, her tongue licking my navel like she was
French kissing it. Then the sheet was pushed back and
I saw her looking at me. She was very happy but also
looked a little intense like a hungry animal. It was
very sexy.
She looked straight into my eyes and licked with her
tongue all the way up my chest, along my neck and
then started kissing me. I was kissing back and then
feeling her body, my hands running all over her corset
and gripping her butt too.
She broke the kiss and squirmed, removing her
panties, moving them up and dragging them across
my face before she kissed me again. Then she sat up
sitting over me and started undoing her corset. It has
these hooks in the front that took a second or two and
made the whole thing slower and exciting.
She pulled it open and off with her back arched and
her breasts spilled out. Then she leaned down and fed
me a nipple, holding the breast to my face and pulling
my head up from the back to feed it to me. I loved
teasing it and chewing on it vigorously. I really liked
that it made her groan and squirm.
Then she reached behind her and grabbed onto my
cock. She pulled away from my face a little and
repositioned herself. I felt her guiding me, then I felt
her hair and my cock against her body. She pushed
down and I pushed up and She made a satisfied
"mmmmmmm" sound while she looked into my eyes.
 It seemed so perfect and natural but my head almost
exploded because I realized I was in her, this was it. I
don't know anything about the face I made but she
kept looking into my eyes and smiling and slowly
gyrating.
I was pumping up slowly until she whispered
"faster, dear." I started pumping faster and harder and
felt myself about to explode. I was about to warn her
when she bent down and whispered right into my ear,
"go ahead. Let go. Yesssssssssss."
I came and came. It was amazing. Then we just lay
there for a long time. Her warm body on top of me. I
could feel her chest and her breasts heaving on top of
mine. Her head was beside me and her lips behind my
ear. I think we almost went to sleep.
After a long time, she lifted herself off me, used part
of the sheet to clean up a little and then slipped her
panties back on. "Why don't you clean up sweetie? I
think Lana's lover boy needs a shower."
I went and she followed me in. While I got in the
shower, she got a washcloth wet and wiped up then
went out.
I finished and shaved and then went out to get
dressed. The bed was straightened up with a set of
clothes laid out for me. I didn't have an undershirt but
she stopped me, rubbed my chest and said "no
undershirt." I got dressed in nice blue khakis, a dressy
shirt and boxers.
She was fully dressed and we were all packed. She
looked nice too in a yellow blouse and a skirt and
heels. I didn't know what we'd do today and I didn't
care anymore.
Someone met us in the lobby and took our bag. We
went to the restaurant. Then they showed us to a table
where Kitty and George happened to be sitting. I
looked at Mrs Wentworth and she shrugged.
George had a lot more energy. He greeted me like
we were old friends, although grandson was more
likely. He kissed Mrs Wentworth's hand in a very old
fashioned way and then stared down her blouse in a
not old fashioned way.
Kitty was charming like the night before. I wasn't
think about how sexy she was this morning maybe
because I had just had sex! I kept thinking about that.
I kissed her hand like George had done but she pulled
it away and pulled me in for a big hug and bit my ear.
George smiled at that. She also came over and
grabbed Mrs Wentworth almost as affectionately. I
couldn't hear Mrs Wentworth but I hear Kitty answer
her, "I'm glad. Did you wear it?" Then, "No wonder
you were late to breakfast." I then saw her squeeze
Mrs Wentworth's butt before they both sat.
 We had a great time with them again which was
amazing because they were so much older and you
wouldn't think we had anything in common. I was
actually enough younger to be George's grandson but
we had a great breakfast. On a day like that, I'd have
had a great breakfast with anyone but it was still
really comfortable.
I got up and went to the bathroom and Kitty walked
with me because she had to check out or tell the desk
something. She walked arm in arm with me which
was nice and old fashioned in a way. She showed me
where it was and said "see you soon."
I was finished in the bathroom and looking in the
mirror while washing my hands wondering about how
much things had been changing. Then I saw Kitty in
the mirror and almost jumped. "Kitty, this is the men's
room."
I guess I wasn't shocked when she said, "I know"
and walked up behind me and put her arms around
me. She was talking to me and saying "Stephen, I'm
not as old as you think and I like you."
I wasn't surprised by what she said exactly. I mean I
could feel it starting last night at the opera and feel
her eyes on me and things. Although, to be honest,
part of me thought she was actually putting a move on
Mrs Wentworth. What did surprise me was her hands
around me which were also squeezing my bulge. I
looked at her but through the mirror and felt her unzip
my pants and watched her reach in and touch it. It
was even arousing to hear her say "Mmmmm, Kitty
likes."
I was turned on. I had found Kitty attractive from
when we met and age really didn't matter at all to me.
But I thought of Mrs Wentworth immediately. I
couldn't do this. I knew I couldn't and I told Kitty.
"Kitty, I can't. I think you're great but Lana is, well
right outside and I could never. I mean I'm really in
love with her and I can't.
I had never exactly admitted that to myself and
maybe I was a little strong but I knew how strong I
felt about Lana, Mrs Wentworth. And it felt good to
say it.
Kitty smiled. She wasn't mad at all. She said, "that's
so sweet. I knew you two were special. I should have
known I'd have to get her to give you to me or at least
share you. You leave it to me." And then she left.
It was a whole weird thing and I took a couple
minutes to get back to normal but then I went back
and sat at the table. Mrs Wentworth looked funny at
me but no one else did. She stood up to go to the
bathroom herself but leaned over before she went
saying "remind me to talk to you about George."
As she was leaving, Kitty got up and joined her. I
guess women head to the ladies room together no
matter what age they are. I thought it was a younger
woman thing.
George told me "I like your woman. She's feisty.
Had a lot of feisty ones before Kitty tamed me."
I didn't know what to say to that. I didn't think Mrs
Wentworth would like being described as "your
woman" but people let guys George's age get away
with a lot of stuff. George then proceeded to tell me
about a lot of the women who came before Kitty. The
ladies were in the bathroom a lot longer than I was so
George got to keep going.
After he told me about a woman who's "tongue was
three feet long ," I decided to cut in.
"George, why did you settle down with Kitty?"
"Well, she was great in bed, no question about that
there, friend. But simple: I loved her. Still do. We
understand each other."
I didn't know what to say. He got real soft spoken
and profound and you can't answer that.
Finally, Kitty and Lana came back. Kitty was
smiling at me and Lana looked a little different but
she was smiling. She didn't sit back down and George
looked disappointed. But she said, "Honey, I
remember you said you wanted to get back by Noon
so I guess we probably should go."
She wanted to leave, obviously, which was okay
with me. I said goodbye to George and then hugged
Kitty who whispered "can't wait to see you soon." I'm
pretty sure George squeezed Mrs Wentworth's butt as
she said goodbye but you can't blame a dirty old guy
for trying. It was nice and we went on our way with
promises to get together again soon.
Mrs Wentworth put her arm around me and said,
"I'm sorry. I didn't want to share you this morning."
I liked that a lot. It made me feel great. I said, "I like
them. They're very nice and I hope we see them again
but I was ready to leave. I'm just as happy with just
the two of us but I need to tell you something. Uh,
Kitty followed me into the bathroom and she kind of
made a move at me. I turned away but I wanted you
to know."
By this time we were walking across the pedestrian
walkway back to the opera house and Mrs Wentworth
stopped me and hugged me. "I'm so proud of you! I
thought she might try something but wasn't sure when
you were back so soon. I'm glad you said no even
though I like her."
We started walking again. She said, "You know I
like them too but they are funny. The whole time you
were in the bathroom, George kept putting his hand
between my legs and trying to run up them. It was a
little creepy but also kind of sweet." She saw my
anger and said "Don't be jealous sweetie. He's just an
old man who can't do much anymore and I had it
under control."
I settled down but said, "I guess it's okay but I don't
like him thinking that way. Or his wife thinking she
could go after me the same way."
We ducked into the opera house with no one around
and went back to what Mrs Wentworth liked to call
"our box." She kept talking on the way there.
"Kitty obviously liked you. I can't blame her for
wanting a piece of what's mine. I'm surprised more
people aren't trying to scoop you up all the time."
It made me feel good to hear her talk that way about
me. I also didn't mind that while she said it her hand
had moved to my butt and she kept squeezing me.
By now we were inside our box. Mrs Wentworth
said, "I love being here with you. It feels like our
special place. Another world where we belong and
where so much started."
Then she turned me and kissed me. Not a soft kiss
but a deep kiss. I kissed back. I was feeling it too. We
stayed there for three or four minutes locked together,
kissing, our tongues exploring each other.
When we took a break, we didn't let go but she told
me more. "Stephen," she was whispering and a little
bit breathless, "you know that Kitty doesn't just like
men, don't you? Do you wonder why I was gone so
long? She followed me to the bathroom and when I
came out of the stall, she grabbed me, maybe like she
grabbed you." As she said that, Mrs Wentworth
squeezed both ass cheeks very hard and pulled me
close.
"She's a beautiful woman and very aggressive. I was
surprised. She told me she knew George had had his
hands all over me and wanted to apologize that they
were George's hands not hers. While we talked, I was
nervous and most nervous of all when she started
kissing me. I don't spend a lot of time kissing other
woman and was shocked. Anyone could have walked
in. What if you had walked in right then and seen me
standing there locking an embrace like this one we
are in now and seen me with Kitty kissing me
passionately..." Mrs Wentworth demonstrated by
kissing me and thrusting her tongue into me. "...with
her hands groping me, exploring my body?" She
demonstrated by grabbing my own hands and moving
them to her chest and squeezing.
I didn't speak. I liked this. I massaged her chest and
did my part to manipulate her breasts and tease her
nipples for the sake of the story. I was actually very
excited. For some reason, thinking about Mrs
Wentworth being kissed by another woman was very
arousing not annoying.
"Stephen, dear, at the time I didn't even know she
had made any kind of move on you. I didn't realize
that just before she had tried to grope you." And with
that her hand was between us squeezing the very hard
bulge in my pants.
Finally, she whispered right into my ear, holding me
close, "honey, I didn't do anything else. I stopped
before it went too far. I could only think of earlier this
morning when we were making love and feeling you
deep inside me. I didn't want Kitty on her knees with
her tongue trying to lick every part of me to orgasm. I
was only thinking of how it would be to have
you..."and as she said it she grabbed and held a tight
squeeze on my throbbing cock, "...to have you inside
me."
Then we broke apart. She said "we better go. I don't
think they will let me take you down to the stage and
ride you for my pleasure."
We went hand in out and back not to the hotel but
the garage where we found the car and she had me
drive home.
We didn't talk a lot on the way but it didn't feel like
we had to. Mrs Wentworth made one call, to her
friend Janine. "Yes, sometime, maybe tomorrow. I'm
feeling tired and I think a night resting will do us both
good. What? Stop that, silly thing. Okay, see you
soon."
She laughed as she hung up. "Janine said to say
hello. I thought we'd stay in tonight."
 We were pulling her driveway and I said "Sure
thing, Mrs Wentworth, whatever you think."
She smiled as I stopped the car. "Stephen, there's no
reason when we're together you shouldn't call me
Lana."
She had never told me to call her by her first name
before even if it wasn't her real first name. I was glad
and walked around the car to open the door and let
her out. She still liked that. "Here we are, Lana, may I
take you into the house?"
And with that I escorted her in. It wasn't that late so
we didn't eat right away. In fact, she had a bunch of
things to catch up on so we didn't do anything
together at first. At least until I heard the doorbell
ring after it was dark.
I stood up and looked nervous but She came down
the stairs laughing and it was just a delivery guy with
Chinese food. She paid him and he left and we sat
down to dinner. She opened a bottle of wine which
was a new thing with Chinese food for me. It was
very nice and kind of normal.
I cleaned up the dishes and even though it wasn't
very late, she decided to go to bed. "I've had a very
busy day and very tiring day so I thought bed is the
best place for me." With that she kissed me and went
up.
 She made a very good case. I was tired too. So not
too much later I went up as well. I went by her room
and she wasn't there. The bathroom, probably. So I
went to my room to get ready for bed before saying
good night.
There were no blankets or sheets on the bed. It had
been stripped bare. Everything was probably being
washed.
I wasn't sure where the other sheets were so I went
back to Mrs Wentworth. She was back and in her bed
now.
"Um, Mrs… I mean Lana, I don't have any sheets. I
mean if you tell me..."
But she interrupted. "Don't worry about that. I think
you would be better off sleeping in here tonight. Go
ahead and strip to your shorts and get in here with
me." With that she uncovered the satin sheets and
patted a spot next to her.
Taking only a second to think, I quickly stripped to
a pair of boxer shorts and climbed in.
Mrs Wentworth Gets Comfortable
This is the ninth part of the Mrs Wentworth saga. It
comes after "Mrs Wentworth and Stephen." It moves
slowly and I like it that way. I always appreciate
comments and suggestions and thoughts and I reply
to every feedback that has a reply email in it. Enjoy.
The last week had been a whirlwind of emotions for
me. I started annoyed at my Mom. She hardly even
noticed I was alive but when she went away for some
sort of work trip she made me stay with Mrs
Wentworth who had been my teacher when I was
younger. I tried to resent her but I found out I liked
her a lot. I started to discover how sexy she was. She
had started out teaching me about dating but then I
sort of fell for her. In fact last night after the opera
was amazing. We had a very erotic night and then this
morning it went much further. We actually slept
together. It was the most amazing night of my life and
not just because I had sex but that was a big part of it.
Now we were back home, at Mrs Wentworth's
house that is. I was going to bed and found my sheets
were being washed. When I told Mrs Wentworth, she
said "Stephen you might as well climb into bed with
me for tonight and we'll worry about the rest in the
morning."
 I didn't need to be asked twice. I quickly stripped
down to my shorts, coincidentally they were boxer
shorts she had bought for me. I climbed between the
sheets she had held back for me and onto the spot on
the satin sheets she was patting with her hand. The
satin sheets felt very nice on my almost naked body. I
loved the slippery feeling and there's something just
plain sexy about satin.
Mrs Wentworth pulled the sheets up and then she
rolled over to turn out the only light left on. After she
turned it out she rolled back over and pulled me
closer to her. "There. This should be more
comfortable than sleeping in the spare room without
any sheets on the bed. Besides, I bet you have never
slept on satin before. Do you like the way it feels soft
against you? I think it's very sensual."
"No, Mrs W – I mean Lana. I've never slept on
satin. It really does feel nice."
While I was talking she reached over and took one
of my hands and rubbed it on her thigh so I could tell
she was wearing a satin nightgown. She kept moving
my hand across her thigh, then her stomach, then up
to her breasts. When she let go, I just kept massaging
her.
"Yes, Stephen the softness of silk and the way it
gently rubs against us is very erotic. The way two
lovers feels completely surrounded by and encased in
silk. The way, OH yesssssss."
The last part was because I suddenly decided to take
her nipples, hard and excited nipples, and pinch them
gently but a little firmly. She obviously liked it so I
kept doing it. I started to massage her breasts briefly
and then pinch her nipples. It made her squirm in the
bed and she was no longer talking. She made noises
but none of them were words.
After a few minutes she grabbed my head and
pulled me to her, pressing it down to find her nipples.
She was moving in every direction on the bed but
pulling my head to her nipple, holding it there and
watching to see my tongue poke at the bumps in her
nightgown. Then I decided to suck on her nipple
through the nightgown. She moved her head back and
started at the ceiling.
I reached up and moved her gown strap off her
shoulder and peeled the top of the nightgown back to
expose her breast. Then I attacked it with my tongue,
swirling around her nipple, touching it with my teeth
and finally sucking on it with lips and tongue
together. She responded by crying out, almost
screaming, and arching her back like a cat.
The whole scene was thrilling and made me want it
to continue. I paused for a minute and she pulled on
my head pulling it up and started to kiss me. She was
out of breath and excited. While she kissed me she
reached down and I felt her grabbing on my cock
bulging in the shorts. I don't have to tell you I was
already very hard. Then I felt her hands exploring and
pushing down on the shorts until they were shoved
off and out of the way, almost down to my knees.
She moved and I moved until we settled into the
right position but our lips never broke their lock.
Finally with her legs on either side of my body and
her hand tugging her nightgown higher and higher,
she broke our kiss and whispered out of breath, "fuck
me, my darling."
I moved slowly as she guided the tip just inside her.
I would have gone slower but she was hungry and
moaning and thrust her hips up to push onto me. I
didn't need much more encouragement and started
pushing in and out faster and faster. Underneath me
she was controlling the pace and squirming almost
out of control.
The noises coming out of her were strange and
wonderful. She was loud and soon I felt her pushing
upward on my chest until I was almost sitting up. Her
legs soon locked behind my back and she was arched
and bent backward a little, her arms spread out to
either side. I was trying really hard to last while she
gyrated every way you can think of.
 Finally, she stopped moving and her body got real
tense and her face froze in a position, mouth open. It
was like someone had stopped time but only for a
second or so and then she screamed louder than
anything I'd heard and her body started shaking over
and over and over again.
Within seconds of this fireworks starting, I couldn't
hold on and I let go and came inside her holding her
twitching body tightly against me.
It was amazing. After a few more seconds, without
moving her legs from their locked behind me position
she sat up a little and grabbed my shoulder and pulled
on me until I went down and lay on top of her with
our heads next to each other.
I was a little out of breath but she was still gasping
for air but also very happy. We lay like that for a very
long time with no need to speak or do anything but
feel our warm bodies next to each other and feel our
hearts beating a little fast.
I almost fell asleep like that but sometime later,
maybe an hour maybe it was less, she sighed and
squirmed a little. "I have to go freshen up, dear."
I got off her and carefully pulled out, half hard by
now. As I slid it out she used the silk of her gown to
wipe it off and then rolled out of the bed and
disappeared into the bathroom. I lay there naked now
and thought about getting up and finding pajamas
somewhere.
When Mrs Wentworth came back, she was wearing
a different nightgown but also satin. She climbed in
and told me to stay naked. Then we went to sleep next
to each other, my naked body cocooned by the satin
sheets and my lover.
I woke up in the morning after a great night's sleep.
Mrs Wentworth was looking at me and said "Good
morning, sleepy." I just smiled.
She said "I can't believe you're both up," and
giggled. I felt her hand on my morning hardness
which was making an embarrassing tent in the satin
sheets. I was about to say something when she turned
and kissed the tip of the sheet tent. Then I felt her
mouth close on it, still sheathed by the satin sheet.
She pushed a hand away and started giving me a
satin sheet blowjob. With her hands rubbing the satin
sheet where it came in contact with my balls, I knew I
wouldn't last long. She paused and said "don't hold
back." I didn't need any extra encouragement.
Within thirty seconds my first orgasm of the day
was on me and my cock released itself surrounded by
sheet and mouth. She sat up again and smiled. "I
should have saved some for my morning coffee." And
then she laughed a naughty little laugh.
 I looked down and could see a mess in the sheets
now.
She got up and started to dress. "Be a dear, after
your shower, bring the sheets for the washer."
Other than that and the fact that we had now had sex
twice and shared a bed and morning blowjobs were
now normal, it was a morning like most other ones.
We had a slow breakfast on the patio and enjoyed
the day.
I said out loud, "I wish this would never end."
She looked at me very intensely and said only, "it
doesn't have to."
I wouldn't have minded if we spent the whole day
alone but Mrs Wentworth had put off her friends
yesterday and today was their normal day for tea or
lunch. So they were scheduled to come over at 2:00.
Mrs Wentworth said, "maybe we should call your
mom before we get started?"
I just shrugged and said, "not today." She had a
mysterious smile on her face.
We went upstairs to get ready, together, in the same
room. I didn't mind when she picked out my clothes.
Since it was tea, she wanted me to serve again and
laid out the tight shorts to hold me in. "I don't know if
our friend can get hard again but you know how you
can be," she said playfully. Then she watched
carefully as I put them on and stood there waiting.
 Actually I liked the feel of the tight shorts, like
biking shorts but softer, almost silky like a
combination of spandex and satin. Mrs Wentworth
had bought them to keep my erections from surprising
people last time I acted as a waiter for her.
Today she smiled and said, "I like that." She
reached down and gently manipulated me, my
erection getting harder while she groped me, and
moved my cock so it was firm in the slightly looser
pocket just down the right leg for it.
Then she stopped. "I don't want you to make a
mess."
I waited while she took off all her clothes and put
others on. She started with a pair of black satin
panties which were very tight on her. "Originally, I
thought they were a size too small but I like them,
don't you?"
"I like them a lot," I said. And I meant it. I stared
while she didn't put anything else on. She had her
back to me and kept bending over and down looking
for stud on the floor. Every time she did, her beautiful
butt looked gorgeous encased in tight black satin.
She kept doing it then she crawled across the floor
to a dresser across the room. I finally figured out she
was partly doing it to tease me and it worked. I then
watched her put on a matching bra which she asked
me to help her hook. "Be a dear and fix me up,
honey," she said.
Then she put on stockings and garter belts. That is a
very sexy look and it drove me crazy. I watched each
garter strap as she put a leg up and hooked it, her
crooked leg drawing it tight. She got a dress out of the
closet but announced it needed to be ironed. She
thought she'd just put it in the dryer for a few minutes
instead so she handed it to me to hold. Then she put
on nice but not flashy black heels and walked ahead
of me downstairs. I followed her as she put it in the
dryer and she stayed like that in her underwear.
I thought it was super sexy and realized that actually
I only had my tight shorts on. She intended to stay
dressed like that but she had me run back up and put
my shirt and pants on. "They're on the bed in the
spare room," she said.
I dressed quickly and came back down. She was in
the kitchen checking last minute on a lot of the food
and showing me where everything is. "Wait a second,
honey, let me look at you and make sure you're
okay." She looked, walked around me, paused in the
back, ran a hand over my butt cheeks which were
prominent because the pants were cut real tight in the
back, and then said "yes, that will be fine."
She was still just in her underwear which was fine
with me. She took her dress from the dryer and put it
on a hanger but didn't put it on yet. "I want to be
careful of wrinkles." She finally put it on a minute or
two before the doorbell rang. I had just finished
helping her zip it up when the bell rang. Walking
around in her underwear had managed to keep me
hard for the last 45 minutes. I wasn't poking out but
remember that these pants were a little tighter in spots
and didn't exactly hide it.
I answered the door and it was her friend Janine.
She swept in and said, "oh hello darling, it's just me
and Kimmie today, I hope that's enough women for
you." With that she kissed me on the cheek and
swatted my butt and walked in. Kim was behind her
and was politer but also hugged me.
Mrs Wentworth welcomed them in and we all went
straight to the dining room. Janine got things started
by saying, "Stevie, darling, I know you're happy to
see me." She looked down at the visible outline of my
erection and winked while I blushed a lot. "But let's
not waste time today. Open the wine and skip the
tea."
I went to the kitchen to get the wine and they kept
talking. "Doris, I love this piece of man flesh you
have staying here. And I know Kimmie was staring at
the bulge he has for us, weren't you Kimmie?"
 Kim giggled and I could just hear her say "stop that
Janine." I expected Mrs Wentworth to say something
but she didn't.
I came in and did my best waiter impression and
served. Janine completely ignored me while I poured
but her hand, out of sight below table level, reached
over and squeezed my bulge while I poured. Kim
didn't ignore me and didn't touch me either but she
was friendly. Mrs Wentworth was talking to Janine
but paused to say, "thank you, dear" and give my
bulge a couple pats.
I wasn't sure who knew what or what they could see
or what Mrs Wentworth was expecting but I didn't
think about it while I got the lunch plates together and
out on the table before sitting down myself. Right
before I sat down, I tried to sound like a very official
servant. "Lunch is served."
Like most of the times they've gotten together, the
ladies talked a lot about a lot of things that I didn't
really know about. They talked about old times and
mutual friends. After a bit, Mrs Wentworth asked me
to get another bottle of wine. I did and started serving
it.
I started with Mrs Wentworth who said, "I could get
used to being waited on." She smiled and patted my
bulge again, this time giving it a couple of squeezes
just so it didn't get soft I guess. I'm sure she knew all
her friends could see the outline, after all she noticed
the last time we did this (see "Staying with Mrs
Wentworth, Part three."). But she still wanted to keep
me nice and hard, like she was showing off.
When I filled Janine's glass, I noticed her blouse
was practically half unbuttoned and she was almost
showing herself off. While I poured, she kept stroking
me the whole time and said "I have to get one of
these." The other ladies thought she meant a servant
which I was pretending to be today but from where I
was standing she might have meant something else.
Kim was last and said less but asked me a couple
questions about the wine and about lunch and about
how I was enjoying myself. She would ask a question
that needed a long answer every time I stopped
talking. It kept me there. She didn't make eye contact
and just stared the whole time at my bulge. It made
me nervous but it was also kind of arousing.
Out of the corner of my eye, I could see Mrs
Wentworth watching. She wasn't obvious and she
wasn't mad. As I finally finished and found my seat
again, Mrs Wentworth asked with a smile, "Is
everything okay, Kim?"
Kim blushed and muttered something.
The rest of the lunch nothing much happened.
That was okay though. I was just having fun being
around three women. They were all very nice. Kim
was very nice and it was cool that she kept staring at
my bulge. I kind of liked that. Janine was like a wolf
and had this really hungry look. I don't know if she
really wanted me bad or she was just teasing Mrs
Wentworth. I guess it didn't matter only Mrs
Wentworth didn't get upset at all today. In fact she
touched me more when people weren't looking than
any of the other women did.
When it was time to leave I got the door and was
there to help if anyone needed anything. Kim kissed
me on the cheek and was very nice. Janine kissed me
on the lips and kissed pretty good actually with her
body pressed against my bulge. She whispered in my
ear "next time maybe I can have that for lunch" and
then licked my ear.
Mrs Wentworth surprised me and them by saying
"don't I get a kiss from the waiter too?" Then she
grabbed me and kissed me more strongly than Janine
did, had both hands on my ass pulling me into her and
made me throb inside the tight pants while her friends
just stared.
Finally she let go and turned to them. "Thanks for
coming girls. Have a good night."
They left and were talking the whole way out to the
car.
Mrs Wentworth giggled a little. "I think maybe that
was bad but I liked it."
 I laughed and said "they're going to think it was
bad."
She turned and said, "oh no. It was very naughty. I
think you bring out the worst in Lana, darling. Do you
think Lana was a very naughty girl?"
I laughed and played along. "It's okay. Yes, Lana
was naughty but I don't mind."
She got a funny look on her face. "No, I know the
rules. I'm not supposed to be naughty. I know that
Lana must be punished." And then she took my hand
and led me into the family room and closed the
curtains.
Then she had me sit on the couch and got on her
knees in front of me. "I'm so sorry Stephen. I've been
very bad and I know you must be firm. I know that
Lana deserves a spanking."
Then she stood up and laid herself across my knees,
holding one leg. It happened to by the leg with my
cock hard in my pants and she seemed to squeeze me
a lot while she did it. She smoothed her legs out. She
had kept her heels on and her dress this time. But I
could see the outline of her garters while she lay there
smoothing her dress tight against herself. Then she
reached out and placed my hand on her ass.
I gave her two quick smacks. They weren't real hard
but they made noise and I know she felt them good. It
was also different from the first time I spanked her
(see "Staying with Mrs Wentworth, Day 2"). That day
I was confused and surprised. Today I knew her and I
knew I was going to enjoy it. I also knew she seemed
to enjoy a spanking too. I had never thought of
spanking as an erotic thing but somehow with Mrs
Wentworth it was.
I smacked her butt just hard enough but not too
hard. After each one I smoothed her skirt again. I
liked watching it get nice and tight across her butt, the
lines of her panties and the bumps from her garters
were all visible. I liked that.
After four smacks, she stood up. "No, Stephen, this
won't do. This is supposed to be a punishment for a
very bad girl, that's what I am. As I lay here on you, I
can feel that you're being punished too. Go ahead and
remove the tight underwear I made you wear. I don't
want you to be restricted like that. She waited while I
turned and took off my pants and the biker shorts
style underwear. I didn't want to take the time so I just
slipped the pants back on without underwear. There
was a lot of room and I felt a lot better.
"Now undo me please, sir." She turned and
obviously wanted her zipper released. I did that and
she took down her dress before walking back and
settling in my lap. "A naughty girl doesn't get to wear
her dress for the spanking."
 No she laid back down and squirmed. I stared at the
tight, shiny satin stretched across her and remembered
how she said they were probably a size too small. I
like the way a size too small looks and I took a few
seconds to just caress the shiny butt across my lap.
Her squirming was making me hard but I just focused
on her. Then I started spanking again. Smack.
I paused between smacks and listened to her
breathe, felt her squirm, and enjoyed the noises she
made. I knew I wasn't hurting her much so the groans
were different. Smack. Pause. And again and again
and again. I did twelve and was going to stop but she
suggested more.
In a very breathy voice like she was trying to hold
on and gasping for air she said "I think I've been
naughtier than that, sir."
I didn't disagree because I loved it. I smacked her
butt another eight times total. By that time, my cock
was throbbing in the pants and leaking a lot. She was
moaning each time and squirming a lot. When I
stopped she lay there for a minute and I sat back and
just stared at her. I watched her shaking slightly and
still squirming in my lap. I stared at the way the
panties were so tight across her butt. My cock was
twitching and she bumped it a few times with parts of
her body.
 Then she got off me. The part of my pants where
she had been laying was a little wet so I guess her
panties were a lot wet. She stood there on shaky legs
and I could tell she was breathing very hard. Her
nipples were very rock hard inside her bra and she
looked at me with a hungry and a little bit crazy look
on her face. She looked at my face for only a second
until she changed and looked down my body stopping
her eyes on my cock twitching and throbbing loose in
my pants. I had a good sized wet spot where the tip
was down the inside of my leg.
She reached behind her and pulled the coffee table
closer and lifted my leg so it was on the table with my
knee bent. Then she straddled my leg and started
rubbing up and down along it, grinding her hips at my
knee. She was using me to rub against and
masturbating herself. That was an incredible feeling. I
would have focused on it and how crazy she had
become that she was humping me but at that second
she reached down and gripped my cock throbbing in
my pants. She squeezed while she humped almost
like she was keeping time.
I was leaning back trying hard not to cum but
having trouble holding back. Soon though she was
sliding and grinding like she was possessed and it was
another minute before she cried out softly as she had
an orgasm. The hand on my pants never stopped and
within seconds I joined her and made a mess all over
the inside of my pants.
After a few minutes of catching our breath, she
stood up and said "you probably want to change your
pants, sweetie." With that, she walked out and into
the bathroom while I went up, washed myself off, and
changed my clothes.
I met her at the bottom of the stairs when I came
back down. She didn't say anything, just kissed me
and then walked up the stairs. I stood at the bottom
staring as she walked slowly up and looked back over
her shoulder when she got to the top.
She came back down about twenty minutes later.
Fully dressed again and acting like nothing had
happened over the last few hours. "Oh, Stevie, hun, I
noticed on my phone that we missed a call from your
mother again. We can call her back of you really want
to or we can just go ahead and eat dinner."
I didn't feel like talking to anyone else so I said I'd
prefer dinner. She didn't judge me but I think it made
Mrs Wentworth happy because she seemed so happy
the rest of the night.
We had a nice quiet dinner, some casserole she
made, and then spent the evening sitting on the couch
next to each other just watching TV. She got us some
wine and we had a very quiet evening. Nothing sexual
at all but I was enjoying just hanging out with her too.
 It was very early when she decided she wanted to go
to bed. She didn't say anything but I decided to go to
bed too. It wasn't really because I was expecting
anything. I just thought it would be nice to go up
when she did too. I went to the other bathroom and
got ready for bed and put on just shorts and a T shirt,
my usual sleeping clothes. I was pretty sure I was still
supposed to sleep in her room but not positive.
I went and she was still in the bathroom so I crawled
into bed. I still liked the sheets although they were
different set but still satin. She came in wearing a nice
top and shorts in silk that were pajamas. I thought
they were very sexy but they were also not super
sexual. She got real close to me and we went to sleep
like that.
In the morning after a real good sleep I had an
erection like I do almost every morning. It's a just a
thing about mornings but it helps I think to wake up
with a beautiful mature woman in silk next to you.
My hardon poked her and she laughed but said "down
boy, let's get some food in us today."
We both went downstairs without getting dressed
and got breakfast together. I got coffee and she got
food and we went and sat on the deck and ate. It was
nice being private but outside at the same time.
About an hour later the phone rang and she looked
at it and said "oh, it's the bitch." Then she stopped and
said "oh, I'm sorry hun. I shouldn't have said that. It's
your mom and I didn't mean it."
I smiled because we felt the same way, "Don't worry
Lana. It's the truth and how I feel too but I guess I
should answer it."
She smiled and answered it herself. "Oh, hi. Nice of
you to call. Are you in the middle of anyone today?
What? No, I meant in the middle of meetings, what
did you think? Anyway, I should get Stephen. What?
Don't even think of it. Stephen is a delightful
companion and I'm not even thinking about you
coming home. Opportunities are important aren't
they? Yes, anyway let me get Stephen. I know he was
going to go out later so let me make sure he's still
here."
Then she handed me the phone with a devilish grin.
I waited a few seconds and then got on. "Oh, hi mom.
Nothing right now, just finishing breakfast and
figuring out what's next today. Going out? Oh yes, I
wasn't sure where I was going but you know. How's it
going there?" I listened to her talk, made a face, and
Lana winked at me like we were conspirators.
Then she got on her knees and came right in front of
me. I was just saying yes to my mom on the phone
while she talked about Vegas. Lana kissed the front of
my shorts a few times until I was hard (it took about
ten seconds, I swear). Then she pushed me to stand up
and pulled them down until my cock popped out. She
grinned up at me and took it in her mouth and started
sucking up and down. I think I said before that she
was really good at blow jobs. Actually I hadn't had
many at that point in my life so I didn't know but she
really was good.
I tried talking to my mom. It was actually even more
arousing knowing she was doing that while I was on
the phone. There I was talking with my mom like
nothing was happening and the whole time I had my
cock in the mouth of my mom's friend. It was
incredible. "No, mom, it's fine. I don't think she
minds having me. I think we're getting along real
well. She's being very friendly anyway."
She popped my cock out and gripped it tight while
she carefully licked my balls for a few minutes. Then
she looked up at me and whispered or sort of mouthed
"give it to me."
I had to hold on for a second because I was talking
but only a second. I asked mom a question and she
went on for a bit which allowed me to relax and spray
with Lana directing my spray so that I came in spurts
all over her pajama top. The blue silk was sprayed
and wet with glob after glob sticking. She grinned and
licked the tip when I was done to clean me off.
Then she stood up and smiled at me as she stood
right in front of me showing the mess I made and
letting me watch it slowly drip down her while she
had the naughtiest look on her face. Soon, very soon,
I managed to end the conversation with my mom.
"OK, mom, anyway I have to go, have fun in Vegas."
I got off the phone and didn't know what to say.
Lana just stood there smiling. She seemed to enjoy
how surprised I was. "I'll take a shower and get
dressed. We told your mom we were going out so
maybe we better." Then she ran a finger through the
drips and globs and looked at the mess on her finger,
smiled and went upstairs.
She went up and started getting dressed. I had no
idea what to wear but nothing special I thought. I
waited a few minutes and then spent some time
cleaning up in the bathroom downstairs before going
up. By the time I got upstairs she was done with her
shower and walking around her bedroom in just a
bathrobe. She smiled and said she had put out some
clothes for me in the other bathroom in case I wasn't
sure what to wear.
I put mine on. Nice clothes but not a suit or
anything. Just nicer pants than jeans and a decent
shirt. I didn't mind being a little bit dressier because I
thought it gave me kind of an older look. I guess Mrs
W wasn't any dressier than me but she looked better
somehow. A skirt showed off her legs and I really
liked her legs. Just putting stockings on them was
always good and she looked casually nice. Not ready
for the opera but all set for any restaurant and almost
anywhere we might go shopping or whatever we
decided to do.
A few minutes later we were driving off, she had
put a couple small bags in the back "in case we get
hungry," she said. But we drove just a mile away to
her friend Kim's house "to run an errand," she said.
I came with her to the door and Kim wasn't
expecting us but was happy to see us. I could see she
wanted to ask Mrs Wentworth about the kiss she had
seen the day before but didn't. One time, Kim did say
"um, Janine and I were talking and we wondered,
um." Mrs Wentworth didn't help so Kim ended up
just saying "we just wondered when we'd get together
next."
Mrs Wentworth just said "soon, I hope. Just tell us
when." Then she said goodbye and we were on the
way. Oh, she also reached over and pinched my ass as
we walked away from the house. I think she did it just
because she knew we were being watched.
Back in the car, she told me, "drive to your old
neighborhood." I wasn't sure what she meant but she
explained, "I mean your mom's old house, that area
over there, it might be a change of pace for us."
I thought it was an odd way to put it but a nice area
to go for something different. It took us a while to get
there but that was okay. I liked driving with Lana and
not just so I could stare at her legs.
After we got to the area, we decided to get coffee
but drive by my mom's place first. I pulled over
across the street but wasn't sure about going in. I
noticed a for sale sign on the front lawn which
seemed really odd. I just looked at it for a minute
until I noticed Lana staring at me. "I'm sorry, hun,
didn't you know your mom put her place on the
market? She should have mentioned it I guess. You
still have a key I'm sure so if you want to go in we
could."
I thought about it and decided I didn't care. "No, no
reason to go in. There's nothing for me in there. I
don't even have any stuff I care about."
She reached over and grabbed my hand and
squeezed it. "You have new clothes and a new life,
don't you? If that woman wants to live there or not, it
doesn't matter to you. It shouldn't. Maybe she'll stay
in Vegas. What would it matter?"
I knew she was right and that I always thought of
her as that woman not like a mom. Besides, I was
living with Lana now and somehow I knew that was
not just for a few days but for a while. Before I knew
it I was driving away. We passed the Starbucks we
had stopped at before ("Staying with Mrs Wentworth,
Day 2") and I pulled in. I didn't care anymore if I saw
anyone I had known before. None of that mattered.
I didn't care. I was out with my friend, Lana. We got
coffees and a snack and sat there and had a nice time.
Of course it was inevitable that I would see Julie. I
guess she often stopped there on her way to work.
She ignored us at first but I know she saw us. After a
could minutes, she couldn't help herself and she
stopped at our table and decided to give me crap
again.
I just wanted to ignore the bitch. Lana though
seemed to enjoy it. Before Julie could say anything
directly to Lana, She jumped in and said, "oh, hi.
You're that funny waitress from that restaurant we
went to last week aren't you? I'm Lana, remember?"
Julie was still bitchy probably because Lana got the
best of her last time. "Oh yeah, you're hard to forget,
Lana, a real piece of work."
I was annoyed but Lana kicked me under the table.
"I try to be unforgettable. But I forget how jealous
you were last time. Try to get over that."
That made Julie really mad. "Jealous? Please! Of
him and you? Like I would ever even care at all."
Lana just smiled and said "ok, sure you're not
jealous of me at all. I can see that. It's so obvious that
you aren't." Then she moved her chair closer to me
and gave Julie a very evil smile and whispered
"Sweetie, I'm holding something you want but you
won't ever get away from me." As she said that I felt
her hand on my crotch.
To be honest, it was great. I had always sort of liked
Julie but maybe just because she was always kind of a
jerk to me and it made me feel great to see her get
annoyed by the amazing and very real, very sexy
woman I was lucky to be with.
Julie just sneered at us but she didn't leave.
Then Lana lifted her hand back up and licked her
fingers one at a time. "Maybe, it isn't me you're
jealous of. Maybe you're jealous of Stephen. Maybe
he has something you want." Then she slowly licked
her fingers and winked.
Julie just turned bright red and stormed out.
It was great. This girl who had tormented before
was suddenly speechless in front of my awesome
girlfriend.
We went back to my mom's house to change. Lana
said we had to be careful because we never knew if
someone would be coming to sell it but probably not
and we'd hear them anyway. She brought a bag in but
said she didn't need to change her clothes. She said
she just needed to freshen a few things up. She
thought I looked fine.
I went and looked around what used to be my room
and realized I didn't really have any stuff that I
wanted. While Lana was in the bathroom, I checked
out my Mom's room, just looking around. While I
was standing there, Lana came out of the bathroom
and smiled.
"Stephen, are you okay? You're not sad that that
woman is selling her house are you?"
"No, really I'm okay. Let's go eat."
She grabbed her small bag and we left the house.
We went to the restaurant that Julie worked at not
because it's good but I think Lana was just rubbing it
in. The hostess showed us to a seat and it turned out
that Lana had asked to be seated at one of Julie's
tables. But she pretended to be surprised. I knew she
wasn't because she said she wanted to get there early
because Julie got off at 7:00. I didn't mind rubbing it
in.
She made a big show of looking at her nametag
before she said "Yes, hello Julie. This will be nice to
have you waiting on me and bringing me everything I
need. But of course the one thing I really need you
don't have because I already have him."
Julie didn't respond except to say, "Bitch!"
Lana just smiled and said "now now, let's have no
more of that. I don't want to report you to the manager
and get you fired from your job just because you can't
stand the fact that I'm enjoying a man you want. Now
be a good little server and go get us a bottle of wine.
This one if you please."
Julie left and Lana moved closer to me. "I think
this'll be a lot of fun."
The rest of the meal, Julie was much better even
though Lana managed to kiss me each time she came
back. Toward the end of dinner, she told Julie, "Bring
us the check, dear. I'm so horny we can't stay for
dessert. As it is, I might have to have sex with my
boyfriend in the ladies room. Is that okay? Does the
restaurant have a policy about that? I hate to get you
in trouble because you watched one of your
customers enjoying each other."
Julie knew she was being teased but just said, "no"
very quietly. Then she took Lana's credit card and
went off to take care of the check.
When she came back, Lana signed the card and we
got up to go. Julie came back around the corner to our
table and Lana said, "you did a good job despite your
feelings so I left you a good tip." Then she grabbed
Julie and pulled her close and kissed her almost like
she kissed me. Julie was completely shocked and
couldn't speak which pleased Lana. She grabbed my
hand and said "you're a better kisser than she is" and
we walked to the door and out to the car.
I walked around the car and held her door so she
could get in. She paused and kissed me. Not a short
kiss but a long which kept getting longer as I kissed
back and out bodies pressed against each other. I was
moving against her and she was squirming and moved
her hand to squeeze my bulge. we kept kissing and
groping for a few more minutes until Lana broke off
the kiss and moved into the car. "I don't want you to
cum in the parking lot, dear."
I walked around and we drove. I wanted to head
home but Lana said let's hold back for a while.
Instead we drove about ten minutes away to a
shopping area. It wasn't a mall, it was upscale,
expensive shops. We got out and walked around.
Lana said it would be perfect for winding down after
dinner. It was good for me to walk because I had
gotten a little worked up between dinner and getting
in the car.
I decided that I enjoyed just being with Lana and
doing anything with her. She stopped and looked at
shoes in a small boutique. Stores stayed open late and
we'd had an early dinner. I had no interest in shoes
but Lana managed to make trying them on very sexy.
She had awesome legs and I liked looking at them.
The sales lady helped a little but Lana kept showing
them to me and showing me a lot of her leg at the
same time. It was like she was teasing me. She ended
up buying a pair which I had to carry.
 We mostly looked in the windows of other stores for
the next 45 minutes. Then we went into a dress store
that sold mostly elegant formal dresses, some prom
dresses, bride dresses, and things that Lana could
wear to the opera. We ignored the prom part of the
store obviously and moved to the most formal
section. Lana was focused on a black gown described
as a ball gown. She took one to try on while I was
looking out the window and the helpful lady who
owned the store brought other ones too. Then they
called me over.
Lana came out in a long black dress. It was all black
on the bottom and the top was black and green. It had
nothing above the top of her breasts and it was
incredible looking. The sales lady said it would be
better with something holding her up and got a white
underwear top that pushed her up. They went back in
for a minute and fixed things and came back out with
her breasts pushed up and together almost spilling
out. All I said was, "wow."
They laughed and the older lady said, "maybe he'll
like the other one too." They want back inside and I
waited.
Then the lady came back and said "now I made her
try this on but just for the style."
Lana came back out obviously still wearing the push
up underwear but wearing a white dress, the top was
satin and like the other dress it had nothing on the
shoulders. I realized it was actually a wedding dress.
Lana didn't say anything but the other lady said how
nice she looked and asked me if I agreed. I just
nodded. She said some couples buy something like
this to spice things up and winked at me. I didn't say
anything but realized that I was getting hard.
Lana turned and had the saleslady undo it right out
there and stepped out of it in front of me before she
went back in to change.
She and the sales lady talked for a few minutes
before finally we left.
We walked down the street some more when Lana
suggested we have a nightcap at a little café. Before
we got there we paused in front of a lingerie store.
We both looked for a few minutes while Lana rubbed
a finger on the palm of my hand.
Finally we sat at the sidewalk café and she ordered
two lattes and a piece of some fancy chocolate dessert
for us to split.
"Stephen do you like when I try on clothes for you?"
I just nodded so she patted my hand and said "I love
trying things on for you. I liked the shoes and when I
tried on the dresses I got so wet I wanted to have you
right in the store. I love feeling like I feel right now. It
feels wild and untamed like I am just one step away
from having sex with you almost anywhere and not
caring who knows."
I had to admit she was making me hard talking like
that. "Lana, I love that feeling and I feel the same way
right now. I like sitting here and knowing that I am
hard as a rock under the table while we drink coffee.
I'm glad it's dark."
Just then Julie from the restaurant was walking
down the sidewalk and Lana got a big grin on her
face. IT was like she knew it would happen. She
called out "hello, Julie." Of course Julie stopped.
Lana was feeling naughty. Maybe it was the wine
she had most of (I was driving) or the fact that her
coffee had a shot in it but I think she was just
inspired. "Julie, darling, we were just thinking about
you and our lovely dinner. Well I was anyway. Poor
Stephen can only think about how hard he is right
now and my hand reaching over and squeezing him."
Then I felt her actually squeeze. "I think he wants a
quickie in the alley by where we parked but we'll see.
How was your shift, sweetie?"
Julie sneered, "Like you care" but I noticed she
didn't leave. In fact she sat down as Lana moved
closer to me and indicated a free chair. She also
leaned slightly but couldn't see anything. I think she
was trying to see what Lana's hand was really doing.
Lana managed to also tell the waitress to bring a latte
for Julie then leaned over and said "I know you want
to see but I'm trying to be discreet. But he is very hard
like an iron bar, the kind of iron you want to be
pulsing inside you. Of course I mean inside me
because that's where he's going to be soon." Lana was
laying it on pretty thick but it was making me excited
and giving Julie a complete shocked look.
Julie was annoyed but a bigger part of her was in
awe of Lana. It was amazing for someone who
seemed to enjoy tormenting me not long ago. She just
drank her coffee and stared.
Lana leaned over and whispered "we can't stay
because we live so far away. I just can't decide
between the car and the alley though."
Julie looked at me and said "but Stephen I thought
you lived a mile from me?"
Before I could say anything Lana said, "No, the
woman he used to live with is selling that house. We
live an hour from here." She smiled at me and I
nodded my head.
Julie was confused but Lana put some money on the
table and said "good night Julie." Then we got up and
walked toward our car. Lana whispered to me not to
look back.
We stopped a few hundred feet ahead and I could
see out of the corner of my eye that Julie was getting
up to go but right then Lana puled me forward and we
kept going. Her Mercedes was just outside the area
with shops and she had me set the bag with shoes on
the car and then started kissing me again.
This time she kissed me with a hand on my pants
and I responded. We moved against the wall of a
building not very near any street lights. We stayed
there for a few minutes and I had a hand slipping
under her skirt.
She broke the kiss and said "come around this
corner." We moved around the corner of the same
building just feet away but out of sight of the main
lighted shopping neighborhood. She grabbed me by
the rear end and pulled me close, slowly grinding out
hips together. My lips went from her mouth to her
neck and then down lower as she pulled open her
blouse. I found her nipple and sucked on it while she
moaned quietly and ground into me. One hand went
inside her waist and then down to find the wetness
inside her panties.
With her hands on my shoulders I knelt down and
pushed my head up under her skirt which she covered
my head with. My hand lowered her panties while my
lips found her slit and licked up and down pressing
my tongue inside her. I felt her hand puling my hair
and her shaking meant she was close. Right now I
desperately wanted her to orgasm.
 It was only few minutes before she made a stifled
scream and shook and finally pulled my head away. I
came out from under her skirt and looked up to see
her smiling.
She kicked her panties off her leg and left them
there against the side of the building while we walked
the ten steps to her car. As I held the door for her, she
turned her head and said "good night, Julie." to
someone standing in the shadows. I got in the car and
we headed for home.
Mrs Wentworth is Naughty
This is the tenth episode in the Mrs Wentworth
series of stories. It follows after Mrs Wentworth and
Stephen. I'm sorry for the long break between this and
the last episode. I got busy and I'm still trying to
figure out exactly where to take the characters. I am
always grateful for ideas and suggestions and
comments and I reply to anyone who uses the
feedback function and leaves an email address to
reply to. I hope you enjoy Mrs Wentworth as much as
I do.
What started out as something annoying had
changed my life. When my mom made me stay with
Mrs Wentworth while she went off to some meeting, I
was originally annoyed that no one trusted me enough
to stay by myself. I was almost 19 and didn't need to
be babysat by some old lady who had been my
teacher. It turned out she wasn't as old as I thought
and she was really nice. And then, well read the first
nine chapters and you can see how well we got along.
I realized that I loved staying there and didn't want it
to end.
I was amazed when Mrs Wentworth had my on my
knees after dinner out the other night. But I don't want
you to think our life together was one sexual thing
after another. There was a lot of time when we just
enjoyed each other. In fact, she was often two
different people. In the mornings she much more like
the person she was when I first got there. She was
more quiet and more proper I guess. In the beginning
she almost seemed like two different people because
at night, or at least some nights, she became like the
person she pretended to be on our first pretend date.
She had me call her Lana in front of people and she
was wilder and everything.
But for the next few days she was mostly like the
morning person. We spend the next few days just
living mostly. We did a lot of things together at her
house and didn't leave the house at all almost but
nothing really sexual happened.
A few days later we had breakfast and after we ate
and cleaned up Mrs Wentworth asked me "are you
worried at all that no one has called?" When I looked
like I didn't know what she was talking abut she
added, "you know, remember the woman who
dropped you off here? Its been a while since she
called. Are you okay with that?"
I laughed. I had almost forgotten about my mom
and she hadn't called in a few days but I didn't care I
guess. So I said, "No, I'm not worried. I guess I don't
care if she calls or not."
That made her happy. I guess because I was happy
or didn't care. I'm not really sure why actually.
Anyway, she grabbed me and said "come on, let's get
ready." I had forgotten her friends were coming over
again.
She had tea or lunch with a few of her friends every
few days or least while I was there she did. An she
liked me to act like a waiter or butler or something
like that. It was really the only she ever asked of me
so I didn't really mind. Besides it as fun to wait on
three or four women as they slowly drank more and
told each other stories.
As we walked into her bedroom, she told me that I
needed to wear the tight shorts she got me before. "I
don't think we can trust your friend not poke out and
expose himself," she laughed. "It's important to make
a good impression for people. Anyway, since you'll
be in black, I'll wear white today." She tossed me the
black shorts that she had bought a week before to
hold me in and then she went into her closet.
When she came out I had my shorts on and had
tucked myself down the one leg in case I got bigger
and was slipping the pants on over the shorts. It was a
good thing I tucked in because she came out wearing
just a white bra and panties. The panties were these
thin white silky ones that were very tight. She thought
there were too small but said she liked the way they
looked. I know I really liked the way they looked. On
top she had a white lace and silk bra. The panties
weren't small. They had a full back and covered a lot
even though they were tight. The bra wasn't tiny. It
covered a lot. But they were really sexy together.
They were very feminine and elegant and nice.
She saw me staring but didn't get mad or cover up.
She started rubbing the front of her panties like it was
a natural thing and said, "I know what you're
thinking. They're small, right? And they are so thin
and silky that they seem fragile like if I'm not careful
they would just rip and fall right off. Is that what you
think?" I didn't want to tell her what I was thinking so
I just nodded.
"Don't worry, Stevie, dear. It is nice of you to be
concerned about my comfort but I'll be very careful.
I'm slipping on these thigh highs that don't need a
garter just to be careful. That should avoid chances
for ripping. And I'm going to wear this long cotton
dress to cover up everything. As she started to put it
on, she looked thoughtful and stopped. "I think for
now, I'll leave it off so we can clean and set the table.
I want to be careful with white and it's only right I
help you set up."
With that she walked slowly away, heels in one
hand and dress in the other while I quickly dressed to
catch up.
We spent the whole next hour getting everything
ready and Mrs Wentworth wore her underwear the
whole time and didn't put her dress on. It was killing
me. It was almost like a slow tease but she acted like
it was perfectly natural and nothing was unusual.
Every time she bent over it stretched those tight
panties even tighter across her butt. I stopped what I
was doing and stared. It seemed like she had to bend
over a lot. Then I watched her as she crawled around
on the floor of her dining room and her living room.
She said it helped her find things to pick up to be at
that level. It drove me crazy but I couldn't show it or
she'd be offended or think I was a pervert or
something.
By the time her friends got there I was as hard as a
telephone pole and of course the stupid waiter's
uniform and the tight underwear didn't hide it. Sure
the shorts kept it in place down my leg but between
the tight spandex shorts, even with a loose leg pouch,
and the tighter pants you could see if you were
looking for it.
When the doorbell rang, Mrs Wentworth almost
answered it then ran off to the laundry room because
she forgot her dress. "Stephen, please get the door. I
almost forgot. That would have been terrible and
what would people have thought! I'll be right out."
Close call I guess but I was happy to get the door and
do my butler act.
 I opened the door for Janine and Kim, just the two
of them today, and said, "Good afternoon, Madam.
Mrs Wentworth will be right with you. Please come
in." I was like a guy playing a butler on TV and I
think they were impressed and also thought it was
funny. Kim gave me a nice hug. Though when it was
Janine's turn she gave me a hug and reached down to
grab at my crotch and whisper "someone's glad to see
me. This makes me hungry."
I turned a little red but actually liked it. Janine let
me go though as Mrs Wentworth walked in. She
greeted them each with a kiss on the cheek and we all
went into the dining room. The three of them all sat
down and Mrs Wentworth said "you may serve." I
started by moving to each one of them with a plate
and placing some of the food on their plate. It was a
chicken and salad dish so it was easy. Kim was nice
and Janine managed to touch my bulge while I served
her. Mrs Wentworth pretended not to notice anything.
When they all had some food, Mrs Wentworth said
"let's start with the wine and skip the tea." I served
her first and they all drank pretty fast though.
I stayed and ate too but they talked mostly to each
other. Kim told Mrs Wentworth she liked her dress
but Janine started early. "It's nice and white and
boring. Is it show you can show Stevie here how
boring you are? It's like you're saying hi stevie, I'm
boring and even my clothes have no color. I bet he's
been bored the whole time he's been here. Have you
even gone out at night or does she make you stay here
and just be bored?" With that she looked at me but
Mrs Wentworth interrupted.
"Don't be ridiculous Janine. I'm a lot of fun and
Stephen is enjoying himself and learning new things."
Janine rolled her eyes and said, "yeah, I'm sure he
is. When was the last time you even went out when he
wasn't here?"
Mrs Wentworth wasn't offended but she said
"Remember the charity event I told you about and
also I took Stephen to the opera so that's a full social
life."
Janine almost laughed. "I'm sure the opera was very
exciting for a man like our Stevie. Everything he
dreamed of." She was being very sarcastic but she
was more right then she knew. She added, "oh and I
hate to tell you that a charity event by yourself is
thrilling. Did you make a late night of it?" When Mrs
Wentworth told her she had been home by 9, Janine
actually laughed but no one seemed offended.
They had finished the bottle of wine so I went to the
kitchen for another. Janine never realized I could hear
everything said when I was out of the room. I heard
her saying, "So what do you say we take your
houseguest and lay him on the table and have him for
dessert."
Kim laughed and told Janine she was naughty. I
thought Mrs Wentworth would be offended but she
just laughed too.
I stopped to pour Janine's wine first but she had me
wait while she drained her glass with one hand while
the other reached over and rubbed my bulge just
below the height of the table. I was embarrassed but
she didn't stop when she put her glass down and said
in a husky voice, "fill me up Stevie." I don't think Mrs
Wentworth was mad but she was staring a little.
When I moved to Kim, she kept her hands to herself
but spent the whole time staring at the bulge Janine
had made so much bigger in my pants. By the time I
moved to Mrs Wentworth her glass was empty and
she was breathing very hard but that's all. She did
drink her wine pretty fast though. She looked at my
bulge too but didn't say anything and didn't touch of
course.
They were all done pretty quickly after that and I
went back to kitchen where there was dessert ready to
be served. It was cheesecake for each person. I got
two plates at a time. I went back and had placed one
in front of Kim. I asked if she wanted coffee too but
she pointed to her still pretty full glass of wine. I
guess she was driving so she drank slow.
 Janine made me wait again while she finished
another glass. This time she didn't touch me but her
dress was up a little and was showing a lot of leg
which I liked. I poured her wine but there wasn't as
much left as I expected. I went back to kitchen for
mine and Mrs Wentworth's. As I grabbed them, Mrs
W came in saying, "Steve, honey, I saw we ran out of
wine. I had an extra glass so I used it up before you
gave the last little bit to Janine. You should bring
another bottle so she can have a full glass."
When I turned to tell her I would, I could tell she
was staring at me. She had a weird look in her eyes
and even looked a little unsteady on her feet. She
listened to me but didn't stop staring and just stood
there for a minute before rushing back into the other
room.
I followed with the cheesecake. I set one before Mrs
Wentworth and then the other across the table at my
seat before taking the wine over to Janine. "I'm sorry
to give you so little before but we opened another
bottle." I was enjoying sounding so official.
Janine leaned in and grabbed my crotch and said
"okay Stevie baby, give me what you got." I gulped
and poured and lingered a ittle until she let my
throbbing crotch go.
I was about to put the bottle on the side table when
Mrs Wentworth said, "as long as the bottle's open, I'll
have another little bit." So I went over, noticed her
glass was empty again even though she had had a lot
more earlier. I poured a little and she told me to "keep
going" until I poured another full glass. She still
looked strange to me but for some reason it was a
little exciting, not that anyone else noticed.
They talked some more and I made sure everyone
had some wine. when I would pour, Janine would
touch me each time and Kim would just stare. The
last time I poured I saw that Janine had her dress
riding very high and split open. It was a wrap around
dress like a coat that tied in front sort of. So the part
leading up to where it was buttoned and tied was like
a slit but in front. When she sat it showed a lot of leg.
By the end of the afternoon she had exposed more
and I could see her panties. They were blue and I am
positive she was showing them on purpose to tease
me.
The last glass I poured for Mrs Wentworth poured
slowly and noticed her hand behind me on my butt.
She just set it there but I was surprised. But it wasn't
long before we were done and they had to go. I went
to the door to say goodbye as each left. Once again as
Kim hugged me, Janine or someone shoved my hips
so I pushed against her. By this time I was very hard
and large and there's no way she didn't feel it. Kim
was quiet but I kind of think she liked it.
 Janine made a big show again and kissed me hard
and squeezed my bulge while she did. She said in a
loud whisper that everyone could hear, "I'd take you
right here if these other two weren't here. See you
soon, sexy."
Mrs Wentworth was right behind as they walked
out. She stood next to me as the two ladies walked
down the steps and I closed the door.
The minute the door closed something changed. Mrs
Wentworth grabbed me and showed me into the door
and started kissing me. It wasn't like Janine's flirting.
Mrs Wentworth was hungry and probably a little
drunk. She kissed long and with a lot of tongue and
with her hands all over me. I felt her pulling on my
belt and my pants. It was like she had more than two
hands.
She was panting and groping and excited. Soon my
pants were down to my knees. Soon after I was
exposed and her hands were on my cock as she was
moaning like she found something special. She
pushed me to the living room but my clothes were
around my ankles and I fell to the floor half in the
living room and half in the hall. There I was laying,
clothes around my ankles, naked up to my waist but
dressed waist up.
She stepped over me and lifted her dress much
higher than her waist. She pulled the tight and I think
really wet panties down and off one leg so they just
hung from one knee. Her thigh highs were on but she
started lowering herself on top of me. I felt a hand
grip my throbbing cock and slide it into her as she
lowered onto me with a moan. Then she sat and
kneeled on me and started to ride me up and down
and with an animal lust.
She was bouncing and moaning and I was trying
hard to last but it was pretty exciting. Behind my head
I heard the door open. I couldn't see but the lust
crazed Mrs Wentworth could. She didn't say anything
but just kept riding and squeezing me as she got more
and more into it. I don't know but just kept going and
tried to think about the door.
It turned out it was Janine who forgot something I
guess. I figured out later that Janine stood there and
watched and Mrs Wentworth just kept going. She was
noisier and noisier and I could tell what was coming.
Not long before Mrs Wentworth's orgasm, I heard
Janine say "isn't this different? It's like college but I'm
watching you get fucked." Just then Mrs Wentworth
started screaming through her orgasm and it seemed
like a pretty good one. Two other things happened. I
heard the door close again and I let go and came a lot
into Mrs Wentworth's quivering body.
She collapsed on top of me for a few minutes,
breathing heavily. I was amazed at how unexpected
and exciting it was to have sex right there on the floor
not even really undressed. After a few minutes, she
sat back up and was smiling. I think she was a little
drunk but also kind of drunk from the excitement not
just alcohol if you know what I mean. She was
grinning and slowly lifting herself off me and leaning
one side so she could grab her panties and slide them
all the way off the one leg they were still on. She
slowly stood up a bit until I came out with a squishy
popping noise. she was looking down the whole time
and watching my semi-hardness slide out. Then she
looked at me and smiled. my cock was coated and
then slowly some of the cum I had pumped started
sliding out of her and onto me. She took the panties,
still wet, and starting using them to clean the mess
we'd made. I liked that a lot.
Then she stood and I did too. She smiled in a funny
guilty kind of way. "Lana's a very bad girl I think. I
should have stopped when Janine came in but I
couldn't. We were very very naughty weren't we?"
She was almost laughing as she said it.
I was trying to be serious and also to play along.
"Yes, Lana is very bad. I guess bad girls have to be
punished."
She got a playful look on her face. "Oh, yes.
Punished. Lana needs to be punished good. Such a
naughty slut.
 Lana is a naughty, dirty, bad girl who needs
punishing." She said it slowly almost like a chant. I
liked the spanking part of the night. inever knew what
to expect but I knew now that she didn't mind it
either.
I also had a question. I remembered Janine saying
something and even though I couldn't see her when
she was talking, I wondered if it was a joke or what.
"Lana, what did Janine mean about this being like
college but the opposite? Did something go on back
then or what? I didn't really know what she meant but
I wasn't paying a lot of attention right then."
Mrs Wentworth looked embarrassed and not sure
how to respond. She didn't say anything at first and
just kept busy adjusting her clothes and going upstairs
to get dressed. But I could tell I was supposed to
follow and she was thinking.
We went into her bedroom and she started looking
through her drawers and her closet and finding some
clothes. She started talking without even looking at
me. "Stephen, when I first went to college I was
young and a little naïve I guess. In my second year,
Janine was assigned as my roommate and she wasn't
naïve at all. She was also very active and had a
system that made sure she had the room to herself if
she was going to need to. But one time, I was already
in bed and asleep when she came in with a guy. She
told him not to worry that I was a heavy sleeper,
which she knew wasn't true. In fact I think she knew I
was awake and was just being funny. I had a pretty
good view of her bed anyway from where mine was.
Our dorm room wasn't big. On top of that she talked a
lot and the guy actually kept saying to be quiet
because he didn't want to wake me. He couldn't tell
but a couple of times I actually lifted my head to look
a little more. The second time I noticed she could tell.
She was very noisy during it and I couldn't help
looking. She and I didn't talk about it but she did it
seven or eight more times that year. I think that's what
she might have meant."
Then she looked at me. "I hope you don't think it's
weird that I was a voyeur for a few years in college. I
guess today was the reverse of it. I didn't plan on
being an exhibitionist today but it just happened. And
I think I enjoyed it a lot. I hope you don't mind."
Who was she kidding? Of course I didn't and I said
it. "Mind? I thought it was awesome. Mrs Went, I
mean Lana, of course I don't mind and who cares
about college. I mean I think I'd have watched too. I
think a lot of people like watching people do things
like looking in a window and seeing your neighbor or
whatever. I mean that's what I hear. And a lot of times
sexual thoughts can be very different and it's just
going with whatever seems cool at the time. I did
kind of freak when I first heard Janine's voice but
what the hell, right? I mean I went with it and it was
real fun. Maybe knowing someone is watching is kind
of a turn on for some people."
That made her feel so much better I guess and she
said, "oh I knew you would understand! But it was
definitely still naughty. Very naughty I think and you
are right to think that Lana is a dirty girl who needs to
be punished right after dinner." She was very happy
and got dressed but not in anything comfortable. She
put on red underwear and more stockings and then
just a silk robe over everything and then led us both
downstairs.
I put comfortable clothes on from the bathroom
including boxers to give me some air. While I did it,
she ordered a pizza and opened more wine. we sat on
the couch but didn't say a lot until the pizza guy came.
then she gave me money and had me go to the door
which made sense.
But while I was paying, she came out and called
from where we could both see her, "make sure he
gives you the breadsticks, honey." I saw the guy look
funny and I turned to notice that she had let her robe
slip and one bra cup was completely exposed. She
looked really hot but disappeared quickly.
The guy left and I went back to the family room.
She was completely covered up and flipping TV
channels. I opened the pizza and put the breadsticks
on a plate and we proceeded to eat and watch some
show she picked out. For an hour we ate and watched
but the whole time she kept having trouble with her
robe. It kept coming open and then after she noticed
she'd cover back up. It happened six or seven times
and kept going on a little longer each time. I got hard
but tried to be cool about it. I didn't need to hide it but
I wasn't exactly flaunting my hardness.
After another glass of wine, she turned off the TV
and looked at me and sighed, saying "I guess it's time.
Lana is ready for her spanking. Can you do me a
favor though? I hate to lay on the rough material of
your pants during my punishment. I know you have
boxers on so can you take off the pants just so I don't
worry about the roughness?"
Of course since I was getting to spank her, I had no
complaints about anything and took them right off.
The boxers I had on were silky ones she had bought
me so they were smooth enough I was sure. She
decided to lie down and had to squirm a lot to get into
position. I don't mind her trying to find the right place
but to squirm with her satiny robe rubbing on my bare
skin was very exciting and it made me pretty hard.
She was just getting into position but it would have
been decent foreplay actually.
 So she was laying there and I started to spank. I
liked the feel of my hand hitting her robe. I didn't hit
very hard of course. This wasn't intense punishment
but more of a symbol I guess and I liked feeling the
soft silky satin with my hand. I would spank and then
rub a little across her rounded cheeks before sliding
off. She squirmed each time.
After just five times she stopped me. She got up but
it turned out we weren't actually done so soon. "I'm
sorry, sweetie, I shouldn't be wearing a robe for my
spanking. That wasn't right." She stepped to the other
side of the coffee table and then looked behind her.
She turned and opened the curtains on the backyard.
Her yard was very private so it probably wasn't risky
but it felt a little different. Then she took her robe and
let it fall. She was wearing red silk and lace panties
and bra along with white stockings, the kind that stay
up by themselves. I had already decided stockings
were probably my favorite lingerie of all time and
looked awesome on her. But the red and the white
and seeing her framed by the exposed window was
amazing.
She came back and laid across my lap again and
adjusted herself in such a way that made sure my very
hard cock was tucked just under her thigh, the end of
it pressing up against her. I put one hand on her thigh,
near where the lace top of her stocking was, not my
spanking hand, and I stared down at the silk tightly
covering her right where I would spank. She looked
incredible especially when she turned slightly and
looked back and up at me and whispered "I'm ready
for my lesson sir."
I would lightly smack her panties and then use my
free hand to slightly squeeze her thigh. Each time she
said "Ow." But it came out more like a soft moan. A
couple times she arched her back and I could tell she
was sort of pushing backward a little which made the
part of her I was squeezing higher and higher. I'm
also pretty sure I could tell she was squeezing her
own breast a few times even though I couldn't see
well.
On the eight spanking stroke, I decided to let me
fingers not squeeze her leg where it ended but I also
moved my fingers a little and lightly touched under
her and almost on her pussy through the panties to see
if she'd react. She shivered but not in a way that made
me want to stop.
On the next spank, I moved my fingers again and
stroked under her body and over her panties. I was
surprised at how wet she was already and loved
hearing her moan not too softly. I did that again and
again and again on the next three strokes. Really what
I was doing was switching between spanking and then
masturbating her. On the next stroke I felt her hands
reach back and caress my balls through the silk
boxers. I was twitching and the tip of my throbbing
member made my boxers wet pressed against her
belly.
With each stroke I was masturbating her longer,
enjoying how wet her panties were and how much she
squirmed at my touch and groaned. Finally she was
shaking and I didn't spank I just kept playing with
her, slowly touching her set slit through her panties
and gently teasing her hidden clit. Her head was
touching the floor now as she was bent down, looking
back under, her body squirming and wiggling back.
She wasn't moaning lightly anymore. She was almost
screaming. Her orgasm was very close. As she started
to scream I made one last smack on her ass, louder
than the others and she started crying out and losing
control.
After her body spasmed so much she pulled my
hand away and slid down on to the floor catching her
breath and trying to recover. In a minute she stood up
and straddled me, sitting on my like on a horse. She
kissed me passionately and reached back behind
herself with one hand to tug on my own throbbing
cock. It was about 30 seconds before I came inside
my boxers while her lips were pressed to me and her
tongue buried in my mouth.
 Finally she let go and smiled at me. Then she stood
up and looked at me. "I was a very naughty girl.
Thank you for punishing me." And she giggled. I was
too dazed to speak. She slipped off her panties and
tossed them into my lap. "These got a little wet,
Stevie." And then she walked away and went up to
bed.