Chapter Text
Title: Hollywood Pornstars - Anna Kendrick
Author: The Chemist
Characters (Sex): Anna Kendrick
Characters (Non-sex): John Krasinski, Madelaine Petsch, Lili Reinhart, Camila Mendes, Natalie Alyn Lind, Katherine McNamara, Peyton Roi List
Codes: MF, MFF, Anal, Bondage, Fist, Oral, Toy
Disclaimer: I make no money from this work of fiction. Do not read if under 18. These events did not happen, I do not know Anna Kendrick, John Krasinski, Madelaine Petsch, Lili Reinhart, Camila Mendes, Natalie Alyn Lind, Katherine McNamara, Peyton Roi List nor am I associated with them in any way. I also don’t know nor am I associated with any of the porn companies/studios mentioned
Summary: The initial chapter of Hollywood Pornstars starring Anna Kendrick, who gets things kicked off with a gangbang.
“So we are headed to a mansion to hear an announcement?” Anna Kendrick asked her driver.
“Yup,” John replied.
“And why can’t we do this like normal people? Over the fucking computer,” the sassy actress questioned.
“Theatrics. You and most of the girls there are actresses. I thought you’d appreciate that. Plus you get to be all dolled up,” John answered.
“I do love fancy dresses,” Anna agreed.
As they navigated the streets, John further explained the situation to his personal sex slave. Anyone influential enough could recommend a girl for contention. It could be a model, actress, or reality star. Anyone really, as long as the shadowy community thought they were famous and sexy enough. Then, the girls would be randomly chosen to have sex, be recorded with the shadowy community, made of mostly wealthy men, able to then purchase the steamy sessions at a steep price. Everyone one. The rich could see gorgeous celebrities having dirty sex, the women’s masters or pimps won by earning ridiculous sums of money. Though it looked like the women got nothing, in reality that then had the wealthy men helping to keep them relevant in Hollywood in order to make them bigger celebrities. Plus, the level of encryption on the videos made illegally sharing them nigh impossible.
“So let’s go inside, you mingle with the others and I’ll network with the other rich and powerful,” John told the actress as they got out of the vehicle.
Anna had a typical quippy response, but John was too numb to them by now to have it even register. The pair separated shortly after entering the mansion owned by some billionaire and it wasn’t long before Anna found other celebrities. Most were younger than she was, and she quickly learnt that while some were in a situation like her own (blackmail or manipulation), the majority were there under their own free will in order to advance their careers.
“Attention all. Please enter the conservatory where the selection process will begin.”
With the announcement made by one of the many butlers, the guests started moving to the rear of the house. Anna went with the flow, staying with the group of gorgeous actresses she had been talking with earlier. Inside the conservatory, apart from the several dozen wealthy and celebrities, were a raised stage with a microphone, several screens and a man, who would be acting as the master of ceremonies. After a few minutes, a loud beep was heard, followed by the left-most screen displaying a name on it: Hoby Buchanon.
“And the next model for Mike Adriano Mr. Buchanon will be...the Riverdale package - Camilla Mendes and Lili Reinhart,” the announcer cried out.
“Okay, okay,” Lili nodded in acceptance.
“Could have been much worse,” Camilla reasoned.
“And we do it together, bae,” Lili added with a warm smile.
As the Riverdale stars were talking, the next studio was shown on the screen. “Another that is fairly straightforward. They tie you up and 4+ men go to town on all your holes.”
“Bound Gangbangs will make a star of...Eliza Taylor,” the announcer stated.
“In Australia, we call gangbangs a regular Thursday night,” the busty blonde smiled, taking her announcement happily.
This earned a rare laugh from the majority of the women present. Up until this point, anxiety was the main emotion radiating from all the women, and for good reason. They were essentially being ransomed off by their sugar daddies, willingly given to porn studios were they were going to be recorded having sex. Being made into private porn stars where wealthy people would circulate the videos amongst themselves, or anyone who could afford it. Anna was lost in the joke and only just caught the next name up on the screen.
“Woodman is hardcore euro shit. Loads of anal, and loves dirty talk,” Anna explained. “And usually brings a friend or 3.”
“And the Spider will be hosting…Peyton Roi List!”
“Spider?” Peyton asked.
“His nickname,” Anna answered.
“Oh! Next is something called Gonzo,” Natalie spoke up.
Gonzo is like Woodman but more intense. Guaranteed gangbangs with up to double digit men. No holds bar. Essentially you either have an elastic asshole entering their studio, or you leave with one,” the Pitch Perfect star explained.
“Gonzo will be making a star out of...Anna Kendrick!”
After that announcement, Anna was still performing the job of explaining the circumstances each girl was headed into, but she wasn’t focusing on who was going where. Instead, she was just curious about what she’d be getting into this weekend. Naturally she was curious and a little worried, but also a whole lot excited…
* * *
“I’m sorry to disturb you, but we need all seats in the upright position as we land,” the stewardess said to the sleeping Anna Kendrick.
“Oh right, thanks,” the petite actress replied.
In as classy a way one could possibly wipe away a small amount of drool from the side of her mouth, Anna did so as she replaced the seat to its upright position. While some of the other women that were raffled off got to stay in the good ol’ USA, Anna had to board a plane the next day for Europe. And not the resort area of Europe either. The Czech Republic.
“Oh my God, I’m in Eastern Europe,” Anna lightly gasped as she exited the airport.
Of course she didn’t have to walk aimlessly around the airport in order to find out where she was going. Presumably the same wealthy individuals who paid for her transAtlantic flight had also sprung for a private driver. At least she hoped so because as soon as she left the departures section of the airport, a man in a driver’s uniform holding a sign with her name on it was waiting for her.
“This way,” the man the size of a linebacker spoke in accented English.
“Lead on, my good man,” a tired but still upbeat Anna replied.
As she drove from the airport to the studio, Anna couldn’t help but get more and more excited. Today she was becoming a porn star! The mere thought alone was insane, but the fact that she could have her cake (doing porn with a major European studio) and eat it too (that her family and friends and public in general would never find out about it) was truly special. Plus, Anna was enough of an avid porn watcher to know what she was getting into with Gonzo. Multiple men with their big hard cocks filling her holes…
“God I’m so fucking wet,” Anna cooed, finding her hand sliding under the waistband of her travel sweatpants to play with her pussy.
“We are here,” the driver spoke over the intercom.
The driver was greeted to the sight of the lovely actress licking down several fingers when he came around to open her door. Anna merely flashed him a smile as he offered her a hand to get out of the vehicle before getting her bags from the trunk. The building they were outside was very much run down, but had a cool, almost haunted look about it.
“I guess this is where the magic happens,” Anna commented as she followed the hulking driver to the entrance.
“Ms Kendrick, great to meet you,” a handsome older man greeted.
“Nice to meet you too. And it’s just Anna,” the petite star replied as she was brought in for a hug and kisses to each cheek.
“Okay. In that case, Anna, you can use the room at the end of the hallway to shower, nap and change,” the man explained.
“All three of those things will be performed,” Anna nodded. “In that order.”
“Perfect. We will send someone for hair, makeup and costume when you are ready,” he added. “And it’s truly an honor to be hosting you.”
“Honestly, I’m so fucking jazzed to be here too,” Anna replied truthfully. “It’s kind of a dream come true.”
* * *
Anna had grown used to handling travel well. A combination of sleeping pills, melatonin and timing your meals was key. Therefore, by the time she arrived in the Czech Republic, she was doing pretty good. A long hot shower and 45 minute nap cured the pint-sized beauty of any remaining fatigue, leaving her chomping at the bit to get things started. A quick call to the man she met earlier occurred, and moments later a woman came into her room with a case of makeup and hair products.
“Well I guess we’re saving money on the costume and clothes,” Anna joked, staring at the two items she was to wear.
“At least they spared no expense on the props,” the woman doing her makeup commented. “You’ll see soon enough.”
Hair and makeup took a short time only. Anna was luckily naturally beautiful and only needed a few touch ups to be camera ready. Her hair was blow dried and, allowing her auburn locks to be worn flowing down to her mid back.
“Any advice?” Anna asked the woman as she stepped into her black heels.
“Try not to break. You may have big boobs but you are very tiny,” the makeup artist commented before leaving.
“Thanks...I guess?”
* * *
“Okay Anna. Show time in 5..4..3..2..” the director counted her down.
No longer in her room, Anna was out in the main shooting room. It was essentially a large open space with a large leather sofa taking up a good deal of floor space on one side of the room. However, Anna wasn’t on the piece of furniture. Instead, she was on the other side of the room which had undergone a large transformation for her shoot today. Astroturf had been laid over the ceramic tile with a large dog bed occupying half the turf, and a dog kennel meant for a large breed taking up the rest of it. Inside the black metal cage was Anna Kendrick, resting on hands and knees with a wide smile on her face. Apart from the back high heels strapped to her feet, the only other shred of clothing she wore was on her head in the form of a headband with floppy dalmatian-looking dog ears.
“Tell us what today is Anna,” the director asked the star.
“It’s a very special day,” she answered.
Anna’s head was at the far end of the kennel as she laid on her back with her feet resting up on the wall of the cage. The camera was at the door of the kneel, looking straight at her spread sex and asshole, though her asshole was currently not visible due to the presence of a black bushy tail. Anna was used to performing, albeit never in porn before, so she maintained a ton of eye contact as she lightly ribbed her wet pussy and tugged on the butt plug in her booty that ended with the tail.
The camera took its time to linger and slowly scan the actress’ body. Starting at her sex, Anna was used to shaving her bush right down to the skin, which was exactly what the studio wanted anyway. With the lens focused there, Anna showed her anal control by pushing and loosening her asshole, causing the butt plug to slowly slide in and out of her anal ring by an inch only. A few more seconds and the cameraman was focusing up on her key asset - her great tits. A solid C cup which were made to look even larger given her positively petite frame, Anna was proud of her boobs and for good reason.
“Why don’t you flip over for me and start to come on out, you good girl,” the director informed.
Always aiming to please, Anna rolled onto her hands and knees, more resembling the dog they wanted her to be. Playing into that, Anna did a few added gestures such as wiggling her ass to make it look like she was wagging her tail. She also licked her hand then rubbed her face. Though that was more of a cat motion, it worked well enough. Finally, as Anna went to back out of the cage and onto the doggy bed, the petite actress began to bark.
“Woof! Woof, woof!”
With several objects on the dog bed, Anna needed no instructions on what to do from there. As she was backing out, her knee had pressed down on a toy that let out a squeak. Not sitting on her booty, Anna took that same orange toy and placed it in her mouth with no hesitation. Once more the toy squeaked as she bit down on it several times before her hand found something else. As she placed the toy back on the bed, Anna brought what looked like a real dog bone towards her face. As she placed the white object in her mouth, the Pitch Perfect star swiftly realized it was an actual dog rawhide bone! Ignoring the meaty taste, Anna kept the bone in her mouth as she massaged her tits for the camera, moaning all the while.
“We hear that ass of yours is rather impressive,” the director commented to the girl now fingering herself. “Why don’t you show us?”
Anna kept the rawhide bone in her mouth as she rolled onto the side, her legs stacked on top of each other and her backside facing the camera. Reaching down, the actress grabbed the base of the toy where metal joined with the fake dog tail. In a practiced motion, Anna relaxed her anal ring and pulled with steady pressure until the 4-inch long butt plug roughly an inch-and-a-half wide popped out of her asshole.
“Mmmm,” Anna moaned as it came out.
Under instruction, Anna put the toy back into her ass and moved it around before pulling it out again. Feeling both loosened up and playful, the actress put the anal toy aside and opted for a dog toy beside her. This one looked like a mini soccer ball with a long red rope coming out of one end. Though most girls would have no hope in pushing a ball over 2 inches wide into their ass, Anna wasn’t most girls. Butting the ball against her sphincter, Anna pushed hard, even getting a helping hand from the director. It took a good half-minute and a lot of effort, but Anna eventually succeeded in fitting it inside her asshole.
“Good girl!” the director cheered. “Now slowly pull it out for us.”
“Ahhh...ohhhh...shhhhiiittt,” Anna moaned through the bone in her mouth.
Though it was a struggle fitting it in her ass, it was even harder coming out. Of course it eventually did, and the gape in her asshole it left in its wake was truly impressive. As Anna took her time bringing the ball towards her face, her asshole stayed yawning wide open, a great view of the first several inches of her bowels on display.
The smile on the director’s face could only be described as beaming. With a wave of his hand, he was ready to move on from the solo teasing and into the main event. At his signal, a pack of 6 completely nude men came strutting towards the famous actress, their dicks already rock hard. Anna knew enough of the porn industry to know that these men had taken some pills to be able to stay rock hard for hours. This excited Anna quite a lot.
“Gonna leash you now,” the only black man present told her, the collar fastened around her neck. “Like a good little puppy.”
Reaching down, the black man used one hand to seize the end of the leash while the other delivered a powerful spank to Anna Kendrick’s slender ass. As he led her to the large L-shaped sofa, the spot his hand had struck was already turning red on the actress. Anna crawled along the tile before climbing atop the leather furniture, at which point she was surrounded. Opening her mouth, Anna seized the closest dick to her face into a blowjob, while the black man behind her didn’t hesitate to join her on the sofa and pushed his inhumanly thick dick into her loosened asshole.
“Fuck that’s a big dick, dude,” Anna moaned before resuming her blowjob.
Being on hands and knees atop the sofa, Anna was restricted in what she could do. So instead, she relied on the males to work around her, which they did with practiced ease. As the black man continued to hammer into her ass, the men took turns with her mouth by more or less face fucking the beauty. Anna was drooling all over the place as a result, but something told the actress that a lot worse fluids than spit had landed on the couch in the past.
After a solid minute of relentless thrusts, the black man pulled out of Anna’s asshole. Playing it up for the camera, the black man pulled apart Anna’s cheeks to show off her gape. Anna played her role by relaxing the sphincter, winking it even wider all while her face was passed from dick to dick. The hands on her cheeks fell away and a giant of a man took up the coveted spot behind the actress, wasting no time in greeting his huge cock with Anna’s colon.
“Open wide, babe,” Anna heard a man speak.
“With pleasure,” Anna cooed.
Meanwhile behind the quippy star, the giant was working more and more of his equally big dick into her well used asshole. Thrust after thrust was delivered until finally all 8 inches of rock hard cock was sliding in and out of her rectum, her cheeks jiggling each time his abs crashed against her booty. As the giant slowed down his fucking, likely to prepare to switch off to someone else, his dick remained fully inside her ass. This was noteworthy because at the other end of her body, a heavily tattooed man was balls deep in her mouth, halfway down Anna’s throat. Taking a dick fully into either end, Anna internally laughed about being so deeply spit-roasted.
“Good girl,” she heard someone say as she was emptied of all cock a moment later.
As the next man stepped up behind her, he had a different idea in mind. A hand between her shoulder blades had Anna being pushed down until her glorious tits were resting flat on the sofa, along with the rest of her body. Her face was positioned perfectly to be hanging off the edge of the sofa so she immediately put the closest dick into her mouth. Meanwhile, the tattooed man behind her climbed overtop and not only began to sodomize her once again, but pulled both her arms back so he could use them to drill even harder into her asshole. It left her completely at the mercy of the man face-fucking her as she was slammed in the ass from the prone-bone position.
“Fuck me like a bad dog,” Anna demanded, smiling all the while.
As the tattooed man’s turn in her ass came to a close, the man who had spat in her mouth was quickest to reach the hole. Leaning down, the man once more spat on her, this time right into Anna’s booty to use as lubrication. The spitter wasted little time after that to become the fourth different man to sodomize the actress, his eager dick pushing all 7 inches into her asshole.
“Fuck me! My ass is yours,” Anna all but begged when her mouth wasn’t occupied with a cock, which was rare.
This was apparently what the man wanted to hear. Pulling on her arms so hard, Anna was actually pulled up to all fours once more. This suited the man just fine as he actually climbed atop the sofa in order to hammer down into Anna’s asshole with renewed force and somehow even more depth. Anna moaned loudly as the men closed around her again, her mouth and hands pleasuring three different men. An eagled eyed man with a bit of a gut decided that a dick could also fit in her pussy, so for the first time during the gangbang a cock made its way into her pink slit.
“Oh fuckkkkk! So much dick!” Anna screamed as her mouth had a surprising break.
A sharp tug on her brown hair forced Anna’s head to look skyward, where the man fucking her ass was waiting. The angle wasn’t great but spitter lived up to his nickname and spat towards her mouth again. This time though, the majority of his wad took her on the cheek and nose, the star feeling it dribble slower towards her mouth after.
“Fuck yes. Use me as a slutty doggy slave,” Anna begged, reveling in the abusive, degrading behavior towards her.
As the men continued to pass her around like a bong at a college party. And once everyone had a go, they kept things moving so the audience wouldn’t get bored.
“Ready for more, girl?” the black man asked.
Following the tug of the leash, Anna got to her feet, but she wouldn’t be standing on her high heels for long. The black man took advantage of the vacated sofa to sit down on the leather surface. Anna knew exactly what to do at this point, especially since she felt his hands spinning her around so her back was to him. Steering his manhood into her ass once more, the black man took over by reclining against the back of the couch and bringing the petite girl with him. Her legs spread wide and soon the gape was filled with the chubby man as he invaded her cunt.
“Yes boys! Fuck me! Use me!” Anna demanded.
Despite the double penetration, it was Anna’s stellar tits taking center stage. The cameraman gave them their moment to shine as they bounced and jiggled with each thrust into her holes. They didn’t go unnoticed by the experienced porn actors either. Hands groped the natural globes regularly, squeezing them or tweaking the nipples. Some men had a more physical approach by actually slapping them, not too hard but hard enough. Anna whelped but didn’t stop them, nor did she stop them as the slaps to her tits moved up to her face. She simply smiled, which made the man fucking her pussy reached down, grip her throat and start to choke the petite woman.
“You liked being choked? Dominated by a bunch of men?” the choker asked, releasing his grip so she could breathe again.
While Anna was busy engaging in a series of dirty talk with the man that had been choking her, she was unaware of when the man stopped fucking her pussy. The black man remained thrusting up into her ass, but as the next man stepped up to her sex, tattooed man decided he wanted to also fuck her ass. Considering that the black guy had nowhere else to go, the second man figured they’d share.
“Ready for another Gonzo rite of passage, Anna?” the director commented.
“Get both those dicks inside me,” the Hollywood star answered.
Though the blowjob and choking were keeping her distracted, another man thought that the rawhide bone would allow her to be bit down on to help with having a second dick added into her asshole. It was the right call. Though Anna had put a lot of thick things in her beauty, having two porn-sized cocks burrow into her anal ring at the same time was a new experience. They took their time and were surprisingly gentle, and their hard work paid off as the head of the second man’s cock joined the entire shaft of the first man inside Anna Kendrick’s asshole.
“Oh God! Oh wow! I did it! Double anal!” Anna celebrated her achievement. “Now don’t just use the tip and actually fuck me!”
“Horny American,” one of the men commented, getting a laugh.
Though the beautiful girl must be in some discomfort, the porn actors had no intention of stopping their progress. The spitter continued to push into her filled backdoor, determined not to stop until both he and his fellow sodomizer were both balls deep in Anna’s asshole. The petite star had replaced the dog bone with an actual suck, bobbing on the fleshy pole while the other three men stroked their shafts and watched as the 90 pound girl took two cocks in her asshole at the same time.
When Anna had drawn this porn studio, she was fully anticipating this moment more than anything. Her constant craving to push her sexual boundaries, especially as a sub, was a large driving factor as was the fact being so horny made the double anal penetration surprisingly liberating.
“I think our little dog needs to be hosed down,” the director commented. “She’s panting, after all.”
The men knew what the director wanted and instantly pulled away from Anna and the sofa. It took a moment for the actress to get it, but she was soon off the couch as well but she was kneeling in front of it. Anna watched as the bald director opened a container and several bottles of champagne came into view.
A man handed her the water bowl and instructed her to hold it up just beneath her face as the other men went about popping the corks on the bottles. Anna knew she was about to get wet, but she was also excited for her first champagne shower at the same time. With a deep breath, Anna pulled in some air then opened her mouth wide.
“This doggy has been a very dirty girl and needs to be cleaned,” the girl in the dog-ear headband played along.
The spit-happy man was the first man up. After a vigorous shake of his bottle, he popped the cork and aimed the initial eruption of champagne at Anna’s insanely perfect tits. Anna let out a giggle as the cool, bubbly fluid smacked into her ivory-colored skin, with a large amount of the alcohol being collected in the massive dog water bowl between her thighs, having put it down. Anna was brave and kept her big eyes open, looking the porn star straight in the eyes as the bowl, and now her mouth, filled. The bowl and her mouth filled even faster now that not only was the Spitter shooting their champagne at her, but also 3 more porn stars. Spitter had stepped aside as the propulsion from his bottle waned, letting his three other recruits take over. The actress’s mouth and bowl soon were overflowing, even with Anna doing her best to swallow mouthful after mouthful of the bubbly fluid. The men became wilder with their aim, soaking Anna’s silky long hair and face extremely thoroughly, but the slender star took everything in stride as she rubbed down her amazing tits in the wetness.
“Time for your drink, little puppy,” the director spoke.
Anna was happy for the intervention as she risked being overcome by the alcohol. However, the teen stayed in character by placing the overflowing bowl on the wet floor before bending down towards it. A hand on the back of her head steered her face towards the huge dog water bowl of champagne where her adorable face was pushed fully into the fluid. The actress with the glorious tits drank some and then ended up blowing more bubbles in the full bowl, however they clearly wanted her to drink the entire content.
“Are you seriously assfucking me as I drink champagne from a dog bowl?” Anna commented after swallowing the bitter, bubbly fluid that was in her mouth.
“Hell yeah I am,” the porn star answered, thumping his pole even harder into Anna Kendrick’s asshole. “Problem?”
“Absolutely not,” the 35 year old replied with a toothy smile as she started to feel a little light headed from the alcohol.
They ended up all having a turn brutally assfucking the young actress as she continued to make headway with the bowl. However, after a few minutes, one of the men decided it was going to slow. Pulling out of her well-fucked asshole, the scarred porn star grabbed the bowl of champagne and dumped it all over Anna’s upturn face. While a good deal made it into her mouth, the majority drenched her face, body and hair, not to mention the dog ears which somehow were still on her head.
“You’re all wet baby,” the black man commented as a pair of dicks entered either of her holes.
“Wonder how that happened,” Anna quipped with a smile.
For the next hour Anna was fucked in all ways. Sometimes they would have a one on one session with her, most of the actors preferring to anally fuck her and ignore her pussy altogether. Other times it was back to a traditional double penetration, but a good deal of the time the men resorted to double anal once they knew that Anna could handle it. This ended up being Anna’s preferred position mainly because it felt good somehow, but also super degrading which was turning her on more by the second.
“Okay men. Finish time,” the director told them.
The actors had been prepped on how the director wanted them to cum so they all stepped away and allowed the black man to pick Anna up. Still in her heels, Anna was placed kneeling on the sofa with her ass hanging over the edge. While the black man started to rapidly sodomize the Pitch Perfect star.
“Fuck. Here it comes,” the black man warned before Anna felt a warmth splashing inside her rectum. “Uggghhhhh!!!”
“I’m next,” the tattooed man called, apparently ready to burst.
Each of the men took turns having a solo session with Anna Kendrick’s asshole until they were milked of their cum as well. In total, Anna received 6 consecutive cumshots into her asshole, a new record for the pint-sized star. Finally, it was the Spitter’s turn with Anna’s all but used up asshole and he performed a solid 5 minutes of the most savage, intense assfucking of Anna’s entire sexual life, which was really saying something. Finally he came with a roar and mighty ass slap before he too pulled out, contributing yet another load into her cavernous asshole.
“You were fucking amazing,” the director commented as the camera light went off.
“No kidding,” one man said. “You need to get into porn full-time,” another of the male talent added.
“Ahh...thank you,” Anna gushed under the praise.
“Seriously though. You loved being used and could handle everything we threw at you,” another man spoke the truth.
“You sure know how to make a girl blush,” Anna giggled. “But I seriously did cum like 4 times.”
“What are you doing tonight? We know a great club around here,” another of the actors offered.
“Let’s do it. I don’t fly home until tomorrow afternoon so I’m game for anything in the next 24 hours!”