Work Text:
He wasn’t ready for the sparkle in her eyes when he turned around.
“Not a word.”
The way her cheeks flushed so deeply when she finally got an up-close look at his face.
“Not even one?”
The way she leaned in, eyes wider than he’d ever seen them, like she was trying to commit every particle of light to memory in excruciating detail.
“No.”
Cloud expected a laugh, or at least a stifled giggle, something that laid bare the sheer absurdity of this plan that Aerith had concocted. The dance with Andrea had been mortifying enough, but then came the public makeover, the rabid, reverent reactions of the crowd (Aerith included), the closeness and intimacy of it all…that he wasn’t repulsed by that aspect of it was eye-opening and deeply troubling in its own right, separate from the way he felt upon emerging from the makeover, ready to be delivered to Don Corneo on a silver platter.
“But you’re so pretty…”
He’d nailed it. And that was the worst part of it all - aside from Aerith looking him up and down like…like…
Like she really believes that.
Cloud ducked around Aerith to escape her piercing gaze, stumbling rather inelegantly across the uneven stone walkways of Wall Market, learning on the fly how to walk when his heels were propped up two and a half inches off the ground. He couldn’t afford to fall and damage the frankly gorgeous dress that he’d been entrusted with, couldn’t risk messing up his meticulously styled hair, his makeup, any of it. He could feel himself retreating into survival mode already, ready to detach and coast his way through the next several hours until he could run the buster sword straight through Corneo’s sternum.
“Cloud, hey, wait, wait up!!”
Aerith, not having any of the mobility issues currently plaguing Cloud, caught up to him in short order, looping her arm around his and redirecting him towards an alleyway off the street, where the dim, flickering street lights reached just enough for the pair to see each other in the darkness. There, she gently propped Cloud up against the wall to keep him steady, then stepped back, hands on her hips.
“Where do you think you’re going, huh, mister?” Aerith chided, pouting a little. “We need to stick together, you know. That’s the only way we’ll get through all of this.”
“I - I know, I just…” Cloud stuttered, looking down at his hands, fixating on the pink polish adorning his nails. “I just need a minute to get it together.”
Aerith stepped forward, leaning in towards him, and Cloud looked away, unable to look directly at the flower girl standing before him. This seemed to be unacceptable for her, as she gently took hold of Cloud’s jaw to turn his face towards her, forcing him to look at her straight on. Even in the dim light of the alleyway, Cloud could see the deep flush on Aerith’s cheeks, her eyes still glimmering as she stared back at him. Something about her expression, however, said that she was feeling more than just amusement, or admiration. There was something more there, something…hungrier.
“Right now, you’re the most put together you’ve been since we met, I think.”
A muscle in Cloud’s jaw twitched at the brazen insult, but he decided against vocalizing it, choosing instead to let out a small huff of annoyance instead. At that, Aerith couldn’t help but giggle, but it faded quickly, and her lips remained slightly parted as her eyes drifted downwards a little, scoping out the rest of Cloud’s outfit.
“Mmmmh…I figured you would look pretty nice, but I didn’t really think you would deal this much damage to me with the end result…”
“Wh - what does that mean?”
Aerith didn’t answer right away, not with her words, at least - instead, her intentions grew clearer when she reached out to caress Cloud’s chest with her other hand, and the hand holding his jaw shifted over to cup his cheek. She pulled him close, pressing her lips to his ear to deliver a candid message.
“It means,” Aerith purred, “that you need to take some responsibility for me. Isn’t that right, bodyguard?”
The hand that was caressing Cloud’s chest slipped further downward, and he let out a noise somewhere between a yelp and a moan when Aerith confidently cupped his crotch in her hand, her fingers pressing firmly against Cloud’s balls through the thick fabric of his dress. There, unfortunately for him, Aerith was alerted to the other source of his discomfort and humiliation.
“Oh, my…” Aerith breathed, her eyes sparkling once more when she pulled back. “Looks like someone’s a little more excited about all this than he let on…”
“Aerith, please, not here…” Cloud whimpered, biting his lip in frustration. He didn’t even truly understand why he was hard, whether it was the cross-dressing, the eroticism of the dance beforehand, having Aerith so fucking close to him…regardless of the reason, the fact of the matter was that he now had a new problem to solve, though Aerith seemed plenty eager to do the solving herself.
Casting a quick glance towards the main road to see if anyone was watching or walking nearby, Aerith carefully crouched down into a squatting position, taking advantage of the generous slit in her dress to do so, then reached for the hem of Cloud’s dress and unceremoniously hiked it up, carefully bunching up the front to expose Cloud’s crotch to the cool open air. Upon seeing the undergarments specially picked out for him by Andrea, however, Aerith’s jaw dropped a little.
“Oh, wow, wow, wow…” Aerith gasped, her eyes nearly bulging out of her head as she feasted her eyes on the sight of Cloud’s privates. Andrea had insisted on authenticity down to the core, essentially forcing Cloud to complete his ensemble with a pair of delicate, lacy black panties. They were just barely able to keep him contained when he was soft; now, cursed by arousal, they had been rendered utterly useless, Cloud’s impressive girth ostentatiously forcing its way out from the side, the thin crotch fabric instead cupping his balls rather uncomfortably. He turned up his nose and shut his eyes, humiliated that they were doing this while he was dressed like this, dolled up for the benefit of a monster down the road.
“You’re super hard,” Aerith teased, delicately circling her thumb and forefinger around Cloud’s shaft, giving him a couple quick strokes and relishing the way he tensed up from it. “Way harder than last time. Does the dress do it for you as much as it does for me? Heheh…”
Cloud covered his face with one hand, shaking his head. They had done this before, a couple of times - first as a “thank-you” gift of sorts from an overly enthusiastic Aerith the night Cloud attempted to ditch her in accordance with Elmyra’s demands, then later on in the tunnels between Sector 5 and Sector 7. In those instances, just like now, Cloud had been overwhelmed by the sheer force of Aerith’s personality, finding himself a passenger to his own pleasure as Aerith used him the way she pleased. He hadn’t protested those times, and he now wondered, as Aerith began to jerk him off in earnest, if indulging her had been a catastrophic mistake.
“You really do look so, so pretty, you know,” Aerith breathed, staring up at Cloud with her wide green eyes, shimmering with excitement as she stroked his cock. “Andrea’s team did an amazing job. Of course, you’re always pretty easy on the eyes, but I think I like you even more like this…makes me want to devour you.”
“Wh - what - ghhhh -”
Aerith punctuated her declaration by engaging in a bit of devouring, taking Cloud’s cock firmly in her mouth, her tongue pressing firmly against the underside of his shaft. The sensation set his nerves on fire - he couldn’t imagine where she might have developed such visceral, exquisite technique, and the way she deployed it on him made his knees shake, threatening to dump him onto the dirty cobblestone and ruin Andrea’s hard work. Aerith, for her part, seemed like she absolutely couldn’t care less about that, singularly focused on servicing Cloud for her own enjoyment, expertly bobbing her head back and forth on his cock, her expression almost smug as she peered up at him, her face just visible over the bunched-up hem of Cloud’s dress.
“Shit, shit - Aerith, you - you can’t do this here -”
“Can’t I?” Aerith fired back, popping Cloud’s dick out of her mouth for a moment to put the man in his place. “This is Wall Market, Cloud. I’m surprised there weren’t two other girls doing this exact thing in this alleyway already when I pulled you back here. Trust me, no one’s going to give us a second look. Just lean back and relax - you’ll feel a lot better when I’m done here, and, frankly, so will I.”
Any attempt on Cloud’s part to protest Aerith’s treatment of him died in his throat as the flower girl resumed her aggressive fellatio, her lips effortlessly gliding down all the way to the base of Cloud’s cock, her throat constricting around its length, her eyes watering a little from the effort. While one hand kept his shaft steady, the other began to wander, first caressing Cloud’s firm, toned thigh, then curling around to his inseam, sliding up to cup his balls through the fabric of his lingerie, giving them a firm, loving squeeze. Cloud’s chest was heaving by this point, his humiliation and reservations steadily being drowned out by raw, instinctual arousal.
He was acutely aware that it wasn’t simply Aerith’s work on him that was driving him insane - it was the debauchery of doing this outside, in plain view of anyone who happened to pass by and look down the alleyway; it was that they were doing this when they needed to make it to Corneo’s mansion to save Tifa; it was the fact that he was dressed like a princess, tiara and all.
It was that it was Aerith, the sweet girl whose church he’d fallen into, whose mother had implored him to leave and never look back, for her daughter’s safety, because Aerith never knew when to stop, on her knees in front of him, intoxicated by his cock, showing him the kind of love he’d never received from anyone else. Even Tifa.
Cloud pressed a hand to his chest, grimacing at the tightness he was feeling behind his sternum. His knees shook, his ankles screaming at him for daring to walk in heels he’d never worn before, his brain filled with the fog of ecstasy. The pressure was building, pooling in his crotch, right at the base of his cock, and he knew that he needed to make sure Aerith knew, needed to make sure he didn’t ruin her makeup with a hot, sticky load of his cum all over her face, even if his cock painfully throbbed at the thought.
“Aerith - aaaahh - Aerith, seriously, I’m - fuck - I’m gonna -”
He conveyed the message about as poorly as he could, but Aerith understood all the same, and she doubled up her work on him, stroking Cloud’s cock from base to mid-shaft, cupping and squeezing his balls to encourage him along, her lips tightly suctioning around just the head of his cock. Peering up at him, the pair locked eyes, and all it took was a cheeky wink from Aerith to send Cloud over the edge.
“Nnnhhhhgghh -”
The release felt like a compressed spring uncoiling, Cloud shooting several thick, gooey ropes of his seed straight down Aerith’s throat, letting out a little whimper of effort with each one. Aerith kept her mouth tightly wrapped around him for the duration, not allowing a single drop to slip out, only pulling off of him when she was sure he was spent. Cupping her hand underneath her chin to catch any stray drops, Aerith turned her chin up towards Cloud and opened her mouth wide, showing him the product of her hard work before closing back up and swallowing it all down in one gulp, licking her lips in satisfaction afterwards.
“Even tastier than before.”
“Sheesh…” Cloud groaned, his face flushing deep crimson at the vulgar display. Grimacing, he reached down to stuff himself back into his panties, a nagging voice in the back of his mind prodding at him over the likelihood that he would stain them like this. Before he could fully re-adjust himself, however, Aerith grabbed his wrist to stop him, and he looked up at her incredulously, his eyes flitting towards the entrance to the alleyway.
“Aerith, come on,” he said. “We need to get going, what are you doing?”
Aerith smirked, her eyes narrowing a little.
“I’m not done with you yet.”
“What the hell do you - hey!”
As Cloud tried to protest, Aerith spun him around by the wrist and pushed him up against the wall of the alleyway. Bracing himself against the rough brick to keep from damaging his dress, Cloud let out a little yelp of surprise as he felt Aerith flip up his dress again, this time exposing his ass to the cool evening air. His disorientation was furthered when he felt her hands on his hips, looping her thumbs into the waistband of his panties so that she could slide them back down, dropping them around his ankles.
“Aerith, seriously, we don’t have time for this…” Cloud protested. He wanted to push back against whatever the hell she was trying to do, but now he had to worry about tripping over his own god damn lingerie, and he had to instead hope that Aerith would listen to reason for once in her life instead. The flower girl, however, seemed less than amenable to doing so, wrapping her arms around Cloud’s waist and pressing her chest against his back as she leaned in to whisper in his ear.
“We’re not going until I finish my meal, bodyguard.”
Cloud shuddered involuntarily as he felt Aerith’s hot breath on his ear, pressing his fingertips firmly against the brick wall in the absence of any other way to react without wrecking his ensemble. She reached down for his cock again, and Cloud was further embarrassed by how quickly he hardened back up in her grip, rocking his hips backwards to avoid scraping against the wall. Aerith had him utterly wrapped around her finger, and they both knew it.
If it was another quick orgasm she wanted out of him, then that was something Cloud could abide by, and at first, that seemed to be the case, as she contented herself with stroking him for a minute or so. When she dropped back into a crouch, however, Cloud was thrown off, and he was further shocked when he suddenly felt her tongue pressing against his asshole, the firm, wet muscle eagerly probing at his rear entrance.
“What the - hey, hold on a second - !!”
Aerith plowed forward, ignoring Cloud’s plea, and he braced himself further against the wall as the girl he was supposed to be protecting broke the plane of his rear end, her tongue wriggling in and taking inventory of his insides. The sensation was brand new, and he wasn’t entirely sure he was enjoying it, though his cock grew almost painfully hard in Aerith’s hand as she invaded him from behind, which to him felt like losing the battle.
“Aerith…fuck, Aerith…”
Pressing his forehead against the back of his hand to endure the intrusion, Cloud panted heavily while Aerith worked him over. The hand wrapped around his cock jerked him slowly and casually, setting a steady, even pace that contrasted sharply with the chaotic feeling at Cloud’s backdoor. It felt as though all of his wires were being crossed, his pleasure centers scrambled and re-aligned, and he briefly worried that this would start to feel something like normal.
As that thought began to settle in his mind, however, Aerith suddenly pulled away, and he heard the shuffling of cloth as she rose back to her feet.
“That should be enough prep…”
Cloud furrowed his brow, fear and confusion gripping him. Prep for what?
Just as he was about to vocalize that query, Cloud received his answer, feeling something cold and smooth press against his ass. Instinctively, he jerked his hips forward, groaning in pain when his cock made contact with the bare brick in front of him, and he whipped his head around to try and catch a glimpse of whatever the hell Aerith was doing.
“Aerith, what the fu - huh!?” Cloud exclaimed, eyes wide as saucers as he witnessed Aerith, dress hitched up to her waist and rather crudely tied off to stay in place, affixing to her crotch a…god, was that a strap-on?? Where could she have gotten something like that? Did she have that on her this entire time…?
“Shhh, shhh, shhhh, relax,” Aerith cooed, running her fingers through Cloud’s natural hair, careful not to snag them on his extensions. “This is gonna feel really, really good, I promise, just work with me a little here -”
“Feel good for me, or for you?”
Aerith’s grip in his hair got a little tighter.
“For both of us. If you stop struggling and just let me have this, Cloud, it’ll go a lot quicker. All I need is a few minutes, okay? I promise it’ll - it’ll be worth it.”
Truth be told, Cloud was not especially powerless here - even in heels that were too high, a stuffy, overly-elaborate dress that restricted his movement, and with the knowledge that remaining spotless (mostly) was absolutely vital to saving Tifa, he was certain that he could subdue Aerith and break free of this latest humiliation before it went to a place they couldn’t come back from. Aerith would be angry, probably, but she would get over it, for the good of the rescue mission. The positives significantly outweighed the negatives.
So why, then, was Cloud still allowing Aerith to violate him like this?
Maybe he really did want it.
The flower girl took Cloud’s silence as assent, and Cloud let out a guttural growl of surprise as he felt her shift her hips forward, spreading his rear hole around her pale pink tool. She had, fortunately, prepared for the occasion, as the wetness from her rimjob mixed with lube that she’d smeared across her shaft prior to entry and made penetration marginally less torturous. Cloud certainly wasn’t making it easier on himself by tightening up so sharply, but he couldn’t help the instinctual reaction, gritting his teeth as Aerith pushed through it to get to his core.
“There, there, that’s it, that’s it, you’re doing great…” Aerith breathed in Cloud’s ear, resting her chin on his shoulder, her right hand snaking back around to carefully, gently stroke his cock and stoke the fires of his arousal. The feeling of being invaded like this scratched at a part of Cloud’s mind that he didn’t quite like, but that feeling was quickly being overtaken by a base, instinctual pleasure bubbling up from deep in his core, and he could feel Aerith strike it over and over as she settled into a bit of a rhythm, thrusting in another inch or two, then pulling out a little and repeating the process, going a bit deeper each time. For an action that the girl had inflicted upon him without asking, she was being rather characteristically considerate otherwise.
Still, this was not what Cloud had pictured when Aerith first pulled him into the alleyway like this. He’d figured that she would want to ogle him a little, maybe get a sight of the goods under his dress, but to go this far was a new low. Or was it a new high…? He couldn’t be sure either way - the answer changed in his mind with every thrust, every scrape of Aerith’s synthetic cock against that spot deep inside. It changed with every rustle of his clothes, reminding him over and over that he was dressed as a woman in order to infiltrate the mansion of a horrible pervert to save the girl he…he…
Loved?
Or was that the girl whose hips kept bumping against his rear?
Cloud had no idea.
The only thing he could cling onto in the moment was the pleasure, raw and instinctual, clenching around Aerith’s shaft and throbbing in her hand. The more she got into the act of fucking him, the more her stroking degraded, her fingers loosening, her motions growing uneven and ragged. It was more than enough for Cloud, however, as the pressure was building, building, building in his crotch, shoved forward from his ass through to his cock, an oncoming tidal wave of ecstasy that he was now powerless to stop. His knees shook, his thighs tightening, his ankles burned, but he kept himself upright even as Aerith seemed to be doing everything in her power to knock him over.
“You’re doing great, Cloud…you’re amazing…you’re gorgeous like this, seriously…my pretty little princess…”
Aerith’s voice was pitchy and fluttery in his ear, taking on the tone that she had when she was on the brink of her own orgasm. He hadn’t even touched her once - was this really doing it for her that much?
“Mmmmmhh…you’re clenching up a bunch, I can tell…are you gonna cum?”
“A - Aerith…”
“You have to tell me if you’re there, Cloud…I want to make sure I see you shoot that big, hot load all over the wall in front of you…just make sure not to get it on your dress, okay?”
“Nnnnngh…Aerith…Aerith…”
Aerith let out a little giggle in his ear, nuzzling against his neck.
“Cum for me, hero.”
“Ghhk -”
Cloud’s legs nearly gave out, and his orgasm hit like a car accident, wringing out several long, thick ropes of semen out of him, his ass clenching tightly around Aerith’s strap with each shot. He splattered his love for her all over the brick wall in front of him, dribbling it all over Aerith’s immaculately manicured fingers, and he pressed his forehead against the wall in front of him, gritting his teeth as he rode the wave to the end. Once the flow subsided, and Cloud was well and truly tapped dry, Aerith gingerly let go of his cock and rocked her hips backwards, her strap sliding out of his ass like a bullet, leaving an uncomfortably noticeable feeling of hollowness in his rear.
His chest heaving, Cloud pushed himself up to a shaky, uncertain standing position, hastily stuffing his soft cock back into his panties and allowing his dress to drop back down, patting it smooth. Looking down at himself, he was a little surprised to see that it looked like nothing had ever happened - the only indicator of their deed was the pit of unease in Cloud’s stomach, and the layer of semen he’d left on Aerith’s hand, which she was examining with too much enthusiasm.
“You’d better clean that up quick,” Cloud grumbled, and he realized his mistake in speaking up a second too late, watching Aerith “clean up” by licking his cum right off of her hand, her long tongue sensually flicking across each finger, leaving not a single drop behind, maintaining deeply uncomfortable eye contact the entire time.
“Done,” she replied, smirking. “Now, for this…”
Reaching down to her hips, she quickly undid the fasteners holding her strap in place, disconnected the dildo from the harness, and wiped it down with a cloth from her clutch bag, wrapping the entire apparatus up and stuffing it in the bag when she was done. Cloud eyed the bag for a moment, unnerved by Aerith’s brazen storage method, but he knew that engaging in any sort of back and forth with her over it wasn’t worth the time or effort.
Once she was properly sorted out herself, her dress back in place and lipstick reapplied, Aerith stepped up to Cloud and gave him another once-over, reaching out to adjust the tightness of his corset and smooth out some of the wrinkles that had developed in his dress. Drifting up to his face, Aerith ran her fingers through Cloud’s hair to adjust his bangs, her thumb brushing across his cheek afterwards.
“So…how was it?” Aerith prodded. “It felt good, right? Do you feel a little more loosened up?”
Cloud’s lips pursed at the question. Now that the post-orgasm haze had fully lifted, he was shifting back into mission mode, the ordeal of just a couple of minutes ago already neatly tucked away in his mind, and he had no desire to open that box again.
“It was…fine.”
Aerith’s lips pursed together for a moment, and she gave him that stare again, the one that felt as though it pierced straight through to his soul. After a moment, though, she shifted into offering that shrewd, mischievous smile he simply couldn’t get enough of, sidled up next to Cloud, and looped her arm into his.
“Good enough for me. Come on, let’s get to the mansion.”
Smoothing out his dress one more time, Cloud ignored the discomfort in his rear, the wetness of his panties, the way that Aerith looked just a little bit more radiant in his eyes now, and set his focus on the mansion. The mission.
Saving Tifa was all that mattered now. The rest…the rest could wait.
“Let’s mosey.”