#a whole lot of suit kink and some D/s if you squint
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Three-Piece Suit
This is 100% inspired by this picture of Chris Evans. Enjoy.
Posted on AO3.
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Bucky never thought that working for Mr. Steve Rogers would be quite like this. Sure, he’d heard the stories, just like everyone else—that Steve Rogers was cold and brutally efficient, that his job was his life, that he didn’t associate with anyone outside of the office, that he was a stoic bastard, too full of righteousness, that he was blinded by his stubbornness. The list could go on and on, really. Most of the gossip surrounding him was unflattering, bordering on rude. And Bucky had heard just about all of it.
And it’s pretty much all true is the thing. Bucky had learned that the hard way when he started working as Mr. Rogers’ assistant about six months ago. The first month had been a lesson in biting his tongue until it bled, in learning that late nights and little sleep were the new normal, that Steve Rogers in real life lived up to just about every expectation Bucky had of him. He had been so critical of everything—from Bucky’s suit (calling his $300 jacket ‘cheap’), to the way his hair had been styled (“cut your hair into something that won’t embarrass me”), to the volume Bucky typed, the way he organized files, how he answered phone calls, the scheduling of Steve’s meetings.
It had been so much, and Bucky hated him those first few months. But the pay was nice, and being able to look at Mr. Rogers when he wasn’t paying attention was even nicer. Because, prick he might be, he was also sexy as hell dressed in his very nicely fitting three-piece Tom Ford suits on the daily.
If Bucky’s being honest with himself, seeing Mr. Rogers in those suits, bossing him around with that trademark cool look on his face, did things to him. Bucky found himself by the end of the second month actually trying to improve himself—saving up for a nicer suit, going to a nicer joint for his monthly haircuts, trying to be more organized, seeking out Mr. Rogers’ approval.
The first time his boss had given him the approximation of a smile, Bucky had felt like his heart was going to beat out of his chest. It had gone on from there, Bucky trying desperately to get what little recognition and praise he could from Mr. Rogers, until something changed about two months ago.
Bucky stayed late because Mr. Rogers stayed late. That in itself wasn’t unusual, but Steve calling Bucky into his office, telling Bucky with all the poise afforded him, for Bucky to kneel down beside Mr. Roger’s desk—that, that was new. Bucky had done it without question, dropping down by the large wooden desk, the hardwood hurting his knees, but he’d stayed there for a little over an hour, until Mr. Rogers had reached out to pat at the side of Bucky’s head, telling him he did well, that he could go now—and to call him “Steve”.
It was innocuous, a one-time thing that Bucky spent way too much time over the next few days daydreaming about while sitting at the desk outside of Steve’s glass office doors, peeking at the other man from the corner of his eye.
But then it happened again at the end of the week, after everyone else had gone for the night, the floor just as hard and unforgiving as before, but this time, one of Mr. Rogers’—Steve’s—hands lay on the back of his neck the entire time. It soothed Bucky in a way, cleared out all of the tension and anxiety from the day’s work. And at the end of the night—two hours this time—Steve escorted Bucky out of the building, giving him a parting “Good night,” that Bucky thought about all the way home, until he finally collapsed into his bed.
It started happening more often after that, almost every night, Bucky on his knees beside Steve, Steve always touching him in some small way, showing him kindness that had eluded the other man all day, him barking out orders and critiques just like normal. And then it had started becoming more.
The first time Bucky sat under Steve’s desk between his legs, Bucky had been nervous. He wasn’t sure what to expect, because this—this was new, was different in whatever silent game they played. And then Steve had reached out—so gently, to bring Bucky’s face to rest against his thigh, his fingers just lightly pressing on Bucky’s cheek, and Bucky could’ve ended it there, could’ve stood up, walked out. But the fingers stroked back into his hair, sweet and gentle, and Bucky had just closed his eyes, leaning further against Steve’s strong thigh, the material of his suit pants softer than Bucky expected, and all the nerves had gone away, even when Steve eventually took his hand back to do more work.
It didn’t turn sexual right away. In fact, the first time had almost been an accident. With Bucky’s face pressed against Steve’s thigh, he’d shifted—his knee had been a little bruised from all the time on the floor, and he’d accidentally moved his head with the rest of his body, shifting up ever so much, until he felt the firm press of something against his jaw, and had stopped moving completely, freezing at the error he’d made.
And Steve had frozen too, legs going rigid under Bucky’s head. But when Bucky had tried to pull his face away from the juncture of Steve’s strong thighs, the other man reached a hand down to cup the back of Bucky’s head, keeping him in place for a moment. And then Bucky had felt Steve’s erection grow against the side of his face, and heat had flooded his entire body. It left him breathing raggedly while he waited for what came next.
And he was not expecting Steve to work his dick out of his thousand-dollar slacks and guide Bucky’s mouth to it.
“Don’t touch yourself,” his order was quiet, fierce, and Bucky had let out a shaky breath right before Steve guided himself between Bucky’s lips.
Steve had done most of the work, fucking into Bucky’s mouth with a hand still cradling the back of his head, keeping him still for Steve’s thrusts. Bucky opened his mouth wider, sucked as hard as he could with little movement, worked his tongue around the head every time Steve pulled back enough for him to, used his lips and tongue to play with the slit at Steve’s head, tasting him on his tongue, swallowing as best he could when Steve pushed into his throat, again and again, even when Bucky’s eyes stung with prickling tears, Steve using him for his own pleasure.
It was impersonal like this, Bucky never seeing Steve’s face, but the heat of the other man, the way his hand curled tightly, achingly, in Bucky’s hair, the way he pressed two fingers to Bucky’s cheek, tapping frantically to convey he was close, as his body started to go rigid once again, as the stoic, harsh breaths from above the desk turned to the softest moans—it went to Bucky’s head in a way he didn’t expect, in a way no one had in longer than Bucky could remember.
He’d come into his dress pants long before Steve came into his mouth, Bucky stubbornly not pulling back, despite Steve’s warning. And Steve had moved his other hand down, then, both hands tugging at Bucky’s hair, holding him on his cock as he came onto Bucky’s tongue, down his throat, filling Bucky’s mouth.
And then, when Bucky had still been blinking stupidly, swallowing the remains of Steve’s orgasm from the corners of his lips, Steve had backed up, hauling Bucky up to sit on Steve’s lap, looking at him in a way Bucky had never seen Mr. Rogers look at anyone, anything.
And then he’d reached toward Bucky’s pants, but Bucky sluggishly shook his head, biting his lip—Steve’s eyes tracking the movement—as he looked away, embarrassed that he’d come like that, like he had a hair-trigger connected to his dick.
Steve’s hand on his chin forced him back, forced their eyes to meet, Bucky face-to-face with that cool look he’d come to know so well once again, but before Steve could open his mouth, could think to say anything, Bucky did.
“I didn’t touch myself.” And damn, his voice sounded wrecked, throat sore and scratchy. But Bucky didn’t hate the sensation, liked knowing he’d have something more tangible than memories to remember this by when the night finally ended.
Steve blinked at him, off-guardedly, until something in his expression shifted—once again back to that unknown expression. “Fuck,” he mumbled, feelingly, and then he’d kissed Bucky, hard and deep, before he pulled back, looking at Bucky for the smallest moment, then kissed him once more, a chaste point of contact, their lips barely touching before he pulled away, tucked himself back into his pants even as Bucky continued to sit on his lap, dumbfounded, lips still tingling.
They didn’t do anything like that again for a while. Bucky went back to sitting silently between Steve’s knees under the desk, added by the addition of a small pillow that Steve brought the day after Steve’s blowjob. It helped a lot. Bucky thought he might be able to stay like that for a full work day, if Steve would ever let him.
The next time, though, when Steve called Bucky into his office, telling him to lock the doors behind him—Bucky knew something would be different. This time when Bucky kneeled down, Steve sat back from the desk, pulling out an extra tie from his top drawer. He’d looked down at Bucky, a question in his eyes, a heat there, and Bucky had nodded without thinking. Steve tied the slip of material around his wrists, keeping them behind Bucky’s back as he reached down to undo his pants. Bucky licked his lips at the sight of him, wanting so desperately to feel Steve in his mouth.
But as Steve rolled his chair closer, he gave Bucky a hard look. “Don’t make me come. I have work to do. And don’t come until I do.” And then he’d slid himself once again into Bucky’s mouth, already half-hard.
And Bucky wasn’t sure exactly what he should do—if he should suck or not, take him all the way in, nurse the head of his cock or the shaft. So he just opened his mouth, let Steve make the choice for him—he liked when Steve made the decisions, honestly.
His jaw ached by the time Steve decided he’d had enough. Bucky had been drooling for a while now, discovering that swallowing the mixture of spit and precome in his mouth had been a bad idea when Steve hissed when he had, hips thrusting, his taste getting stronger. So Bucky slacked his jaw, moving to gentle suckles and Steve had relaxed back into his work. He knew the spit covered his chin, must be a little puddle on the floor in front of his knees by now, and his wrists felt a little chaffed from the tie, but Bucky cared about none of it, especially when Steve rolled back, looking down at Bucky after a few hours, and started stroking his cock, Bucky’s saliva wetting the way.
Bucky didn’t think he’d ever forget that view, Steve looking down at him, his fist closing over his erection, dragging up and down so tightly Bucky’s own cock ached in sympathy, throbbing between his legs. And when Steve’s thighs started to tremble, when his strokes became more erratic, his throat emitting those small, soft moans that Bucky already couldn’t get enough of, Bucky just tilted his head back, opening his mouth.
As if that had been all Steve was waiting for, he’d come, letting himself go above Bucky’s face, coming into Bucky’s open mouth, on his cheek, his jaw, a few drops sliding down toward his neck.
And fuck, Bucky wanted to come so bad, wanted anything Steve would give him, swallowed down his come like it was the best thing he’d ever tasted, so, so desperate for any little thing from Steve, from this gorgeous, amazing man above him.
When Steve caught his breath, he reached out a still-sloppy hand toward Bucky, pushing it into his hair to grip the locks. “Can you come like this?”
Bucky nodded, feeling the desperation, the heat pooling in his gut, the way the front of his pants were so slick, ruined now, just like his other ones, pressed against his dick, trapping it.
Steve’s hand moved down to caress Bucky’s sore jaw. “Then do it. Come for me.”
Bucky did, moaning loudly, hips stuttering against nothing, his knees trembling, giving out on him as the orgasm overtook him. But Steve caught him, let Bucky fall against his open legs, trailed his fingers through Bucky’s hair, down to the back of his neck.
“That was so fucking good, Bucky. You’re so good for me. Thank you.”
The words had been soft, almost sweet, sounding like that expression Steve wore last time on his face. It didn’t escape Bucky’s notice that Steve’s still-exposed cock had hardened a bit at Bucky’s display, but the other man didn’t at all seem concerned with it. Bucky closed his eyes, never wanting the moment to end, and Steve seemed posed to let him.
It didn’t go beyond that for a while, until that one time that Steve had sat Bucky down on his lap, his knees on either side of Steve’s thighs in the chair, Steve’s hands on Bucky’s hips, their cocks rocking together through the material of their pants, Steve panting harshly against Bucky’s throat as he thrust his hips up, working himself off against Bucky. He’d come embarrassingly quick that time, moaning what might’ve been Steve’s name as he did. And then Steve had groaned—an actual, real sound, so different from the small noises Bucky’d become accustomed to—and his hips stuttered against Bucky’s.
Of course, that was when Steve had told Bucky to get onto his knees before he went to the bathroom, coming back out in just his crisp white shirt, jacket, vest, and tie all gone, and wearing different pants. He’d tossed the pants he’d been wearing at Bucky’s feet and told him to get rid of the come before it stained.
So Bucky had, tonguing the material for all he was worth, until Steve was deemed satisfied.
It happened with more frequency following that. Bucky never quite knew what to expect—sometimes he sad under the desk, innocently, sometimes with Steve’s cock in his mouth—one notable time with Bucky sucking on Steve’s balls—and sometimes Steve sat Bucky on his lap, Steve’s exposed erection sliding against the seam of Bucky’s pants as Steve somehow still managed to get work done even as he destroyed and remade Bucky’s existence, so painfully hard with the feeling of Steve’s warm cock sliding against the most sensitive parts of him, over his covered asshole, all the way down to where his balls had drawn up tight inside of his pants.
Bucky ruined more pants than he ever thought possible, until little, unassuming boxes started showing up at his desk in the mornings after they ‘worked late’ together, with high quality suit pants in varying styles and colors, the measurements just a little smaller than what Bucky wore—and when Steve started casually grazing his hand over Bucky’s ass during the work day when Bucky would bring him a file here, or a coffee there, Bucky understood exactly why that was.
He didn’t feel nearly as bad about ruining the pants Steve gave him. It was all his fault, after all. Until one of them had the smart idea to start actually undressing in advance. Bucky’s not sure if it was him or Steve, but the next thing Bucky knew, his pants had been taken off, lying in a puddle on the floor, abandoned.
Of course, Bucky forgot just about everything when Steve had then laid Bucky down on his stomach over the desk in front of his chair, ass exposed, on display, not at all expecting it when Steve started to eat him out, licking and nibbling and working his tongue in and out of Bucky’s body until he was a moaning, writhing mess, shirt sticking to his back with sweat, Bucky’s fingers clutching at the edge of the desk in vain, willing himself to be good, to stop moving for Steve, the man’s iron grip on his hips seeming to do nothing to keep him still.
He’d come clenching his ass around Steve’s tongue, moaning loudly, throat raw from begging for the orgasm every time Steve had pulled away, had pressed a thumb or a finger inside, until Bucky felt like he would go insane from the pressure building up inside of him.
And then Steve had stood up, looming over Bucky’s back, sliding his cock along Bucky’s slickk crack, over his hole, head almost catching on it with each slide, stealing what little breath Bucky could drag in, until Steve came over his ass cheeks, slapping his softening cock against Bucky’s hole once he finished as if to punctuate that he would try that out next.
They didn’t really talk about penetration—didn’t really talk about anything. Neither one mentioned their late night sessions, nor their one-time kissing; they simply went about as if things were normal. And then one day, just like the small boxes appearing at Bucky’s desk, a folded piece of paper greeted him, telling him Steve was clean in so many words.
Bucky left his own on Steve’s a few days later.
Everything since then had been a waiting game, amping up this thing between them to a new level. Each night, Bucky wondered if it would be tonight. He’d made sure to be thoroughly clean each evening just in case.
And then, one night, the waiting finally ended.
The intercom buzzed like normal, as soon as everyone else had left, and Bucky abandoned his desk, walking through the doors to Steve’s office without a word. Steve didn’t sit at his desk, giving off the pretence that this might be anything other than what it was. Instead, he stood in front of it, hands in his pockets, hips cocked, head tilted, that intense, unreadable look in his eyes, watching Bucky’s every movement.
Bucky stopped in front of him, their eyes locking for a long moment before Bucky dropped to his knees in front of his boss. When Bucky reached out to undo Steve’s pants, Steve didn’t stop him, just kept looking down at Bucky with that heavy gaze, watched him as Bucky took Steve into his mouth, as he started sucking Steve off for all he was worth, using every trick he’d learned over the last few months, knowing exactly what Steve liked and giving it to him. He wanted this to be good for Steve, wanted to be good for Steve. He swallowed him down, until his nose pressed against the soft hairs that trailed down Steve’s torso from his belly button, swallowing convulsively around the head of Steve’s cock before pulling back, tracing the vein on the underside of Steve’s cock with his tongue, worshiping the other man’s dick like this might be the last time he gets to do this, gets to feel the heavy, silky-hard length on his tongue, gets to taste his precom, feel how hot and hard Bucky makes him.
And then all too soon, Steve pulled Bucky off him, pulled him up to standing, surprising Bucky with a kiss that Bucky thinks might have flayed him alive, since he can no longer feel his own body.
The kiss didn’t last long before Steve reached out to strip Bucky of his clothes, those strong, steady fingers working at his buttons, pushing his jacket and shirt over his shoulder for the first time, his eyes hungrily raking over Bucky’s chest, even as his hands moved down to work Bucky’s tight pants from his hips, down his legs, until Bucky cursed at his shoes and did his best to step out of them along with his pants and underwear.
Steve began to undress then, taking care to fold each piece of his suit after it had been taken off, setting his cufflinks, watch, and tie down on top of the small pile when he finished. And then Steve reached behind himself, arm outstretched over the desk, and pushed all of its contents to the floor. Pens skidded across the hardwood, papers went everywhere, Bucky thought he heard the shatter of a paperweight. But Steve didn’t seem to care, just looked at Bucky as he sat atop the oversized desk, spreading his legs, his hard cock bobbing.
Bucky moved, almost pouncing on the other man, climbing up on the desk, his thighs cradling Steve’s hips, sitting back so Steve’s cock rubbed against Bucky’s ass, his arms wrapping around Steve’s neck, keeping them both upright.
Reaching back, Steve dug in a drawer, coming away with a bottle of lube—and Bucky felt his face flame at that, at Steve being so ready to take him. Steve’s eyes met Bucky’s again, leaning his head back to bring their lips together in something more bitey than sweet, even as he popped the cap of the lube, then brings his fingers to Bucky’s rim. Bucky shivered at the coolness, at the way Steve’s fingers circle his rim, warming the lube and Bucky’s body with his ministrations.
Bucky let out a long sigh when Steve slid the first finger inside of him. Steve had only done this the one time he ate Bucky out—memorable as it was, Bucky was ready for something more, had taken to stretching himself out every morning before work.
He told Steve this, felt the other man’s erection twitch against him, ground down on it, even as Steve added a little more lube and pushed in with two fingers. Bucky moaned at the feeling, Steve’s fingers filling him up better than his own could, getting to work at stretching him for Steve’s cock, working wet and firm inside of Bucky’s body, twisting and scissoring until he managed to push a third finger in. Bucky squirmed back against them, wanting them deeper, chasing the ghost of sensation when Steve dragged his fingers over Bucky’s prostate.
And then Steve’s fingers left, hands moving to guide Bucky down, Steve’s cock sliding again against him, catching at his rim, but this time sliding in, stretching Bucky out, filling him up until he’s so full, unable to move with the pleasure of finally, finally having Steve inside of him.
Bucky only came back to earth when Steve lifts his head, gazing at him, eyes dark, heavy-lidded. “Don’t touch yourself.”
And it’s like a repeat of their first time—Steve holding onto Bucky, taking his pleasure from him, chasing his own release. Grabbing at Bucky’s hips, Steve worked his hips up as he pulled Bucky down, taking him in hard, deep thrusts, rubbing relentlessly at Bucky’s prostate once he found the spot. Bucky clutched at Steve’s neck, fingers digging into his shoulders as Steve maneuvered him up and down, rocking their hips together in an almost desperate drive that left them both gasping into the space between them. Steve’s hands move eventually to splay over Bucky’s ass, pulling his cheeks apart, continuing to thrust, long, hard strokes that Bucky felt all the way to his core. He all but keened when Steve pressed a finger to his rim, to where Steve’s cock stretched him open, filling him up, rubbing at the rim until me managed to press just the tip of his finger inside.
Bucky came with a shout, his orgasm taking him by surprise, the heat flooding his body at being so full—so full of Steve—overcome by the feeling of Steve surrounding him, giving Bucky everything he wanted.
“Fuck.” Steve hisses, “Shit, Bucky—” And then Steve moved both hands back to Bucky’s hips, thrusting in earnest now with rough, long strokes, hips stuttering, his breath ragged, moaning, eyes closed as he gave himself over to it. Bucky watched in fascination, panting, their bodies slick with his come where they’ve pressed together. Steve’s mouth opened on a groan and Bucky didn’t think anything of leaning forward, closing the distance, of covering Steve’s mouth with his own.
This kiss was different—tender, almost. Steve cradled Bucky’s jaw in one of his palms when they’ve finally pulled away from each other.
Still panting, Steve opened his mouth, eyes open and staring into Bucky’s. “You’re fucking perfect, Bucky.” Steve pressed his forehead against Bucky’s, neither one of them in any rush for Steve to pull out, even as the sweat and come starts to cool on their skin. “I can’t believe I get to have you.”
Bucky wasn’t sure how, but he managed to find his voice, pressing one more chaste kiss against Steve’s lips. “Only you, Mr. Rogers. Just you.”
Steve swore again, bringing his lips back to Bucky’s as his hips rocked just the slightest bit inside of Bucky, making them both moan into the kiss. Bucky couldn’t wait for the next round.
No, Bucky never thought that working for Mr. Steve Rogers would be quite like this.
#stucky fic#stucky smut#stucky#freshwoods: fic#a whole lot of suit kink and some D/s if you squint#buckystan-plums
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𝐝𝐫𝐞𝐬𝐬 𝐮𝐩 🎀 louis ives x reader
𝐬𝐮𝐦𝐦𝐚𝐫𝐲 🎀 taking out the shy boy from the opera takes an unexpected turn, in the best possible way
𝐰𝐨𝐫𝐝 𝐜𝐨𝐮𝐧𝐭 🎀 9.4k
𝐰𝐚𝐫𝐧𝐢𝐧𝐠𝐬 🎀 smut (18+ only; penetration, oral sex m receiving), crossdressing/genderbending, louis uses primarily he/him pronouns but is still a genderqueer icon, reader is also gnc (and implied bi), feminization kink, praise kink, shy insecure babby louis is babby, slight d/s dynamic (with subby!louis and dom!reader, obviously)
Louis sighed as he leaned back against the wall, resting the back of his head on the ornate wallpaper with his hands stuffed into his suit pockets.
It was only his first time at the opera, but he liked it much more than he thought he would; so much so that he was a bit anxious for intermission to end so he could get back to it.
Waiting for Henry to finish in the men’s room was, obviously, pretty boring. Louis resorted to people-watching in the lobby to pass the time— mostly it was much older people… in fact it was exclusively much older people. He liked the way they were dressed though: tuxedos, evening gowns, silk shawls and gloves.
His posture straightened when he saw you, for a number of reasons (three, exactly). One, you were significantly closer to his age than anyone else here. Two, you were a pretty girl, in his personal opinion. And three, you were wearing a tailored three-piece suit and tie. Not the overly-curvy cut of a woman’s suit, not a blazer and slacks, this was a straight, slim, two-button jacket and the whole ordeal; even black leather oxford flats of a clearly masculine variety. He’d never seen a girl in a suit like that, he had to squint to look at your face and make sure he hadn’t just mistaken a more feminine man for a woman— but no, the makeup on your face and the feminine curve of your body (which couldn’t even be suppressed by men’s clothing) made it pretty clear you were at least some amount of female. He was impressed; he was intrigued… he was even a little intimidated.
And in a way he hadn’t expected at all, he was attracted to you. Not that being attracted to pretty girls was some kind of massive undertaking, but this was more than that. He was used to the natural draw to a good-looking woman, and to the odd jealousy he felt when he saw a woman wearing something that he wished he could. This was obviously more the reverse: he could wear suits, he was wearing one now, and somehow you seemed a lot more comfortable in yours than he felt in his. In the least perverted way possible, he imagined what kind of undergarments you might have on under that— a lacy bra, pink panties, nylons? Maybe something more practical? What a dream it would be to have something like those on under his suit…
You suddenly glanced his way, and he was so mesmerized by your eyes that he forgot to look away just a few seconds too late. Staring intently down at the floor as if there was anything to look at there, his heart started to beat a little faster as he saw you approaching in his peripheral.
His attempts to act nonchalant, even ignorant, to your presence were… pitiful. He started up and off to the side, as if the corner of the ceiling bore anything of note. You stopped just in front of him, giving him an expectant smirk as he, finally, met your gaze— acting as if he just now noticed you.
“Hey,” you greeted. “What were you staring for?”
“Oh—” he choked, “well, uh—”
“Don’t be scared,” you soothed, “I don’t bite, except when asked nicely.”
“Um,” he stalled, thrown by your slight innuendo. At least, he thought it might be an innuendo based on the sparkle in your eyes, but he was only tangential aware that biting could be a sexual reference. Do people really do that? Does she really do that? “Why are you wearing a suit?” he finally found the courage to ask aloud.
“Do you have a problem with me wearing a suit?” you returned.
“N-no, but, I just can’t see why you’d want to,” he explained. “They’re not especially comfortable. A dress seems more… breathable.”
“For the legs, sure, if it’s a ballgown— but the torso? Way too tight,” you grimaced, “you can feel it on you all the time. Makes it hard to relax.”
He took a mental note of that for later, a detail to help him accurately imagine how it would feel to wear one. You can feel it on you all the time… like a hug! That would be so nice…
“Suits are more fun,” you announced. “I think I look good in them.”
I think you look beautiful in them. “Do people look at you differently when you wear that?” he asked.
“Yeah, I pretend not to notice the rude ones,” you shrugged. “And every once in a while I get the attention of somebody cute, who may or may not stare at me from across the room creepily.”
Louis cleared his throat when he realized you were talking about him. You called him cute! That’s what that was, right? But you also called him creepy. So he wasn’t sure what to think. “I’m sorry,” he stuttered out, but he was smiling a bit from the compliment, which he worried made his apology less sincere.
“It’s alright, I didn’t mind,” you offered, and just as the conversation was really getting interesting, Henry suddenly appeared from the washroom; Louis tried not to show his disappointment so obviously on his face.
“Oh!” Henry smiled as he looked between you and Louis standing in front of each other. “I see you’ve met a lesbian,” he said to Louis.
Louis’ eyes went wide and he opened his mouth to chide Henry for his inappropriateness, but you jumped in first. “I’m not a lesbian, actually,” you corrected, “just progressive.”
Henry spitefully crossed his arms. “What’s the difference?”
“The difference is I like dick,” you explained; Louis was a little stunned by your bluntness, but amused by the way it threw Henry off of his game. “Maybe not exclusively, but…”
“Hmph!” Henry coughed disbelievingly.
“In fact, I was just about to ask your friend out for a coffee sometime,” you informed him, making Louis’ throat suddenly dry.
“I was… just about to do the same,” he bluffed.
Henry rolled his eyes and started to leave, mumbling a few gripes about ‘what’s this world come to?’ and ‘women don’t even wear women’s clothing anymore’, before turning back and looking at Louis with a furrowed brow— like he’d expected the young gentleman to follow him without question. “Come along, Louis,” he instructed.
“I… I’ll join you when I’m finished with my conversation,” Louis replied, puffing his chest up just a bit. Henry was obviously frustrated by Louis standing up to him, and Louis hated that all of this was happening in front of you. A tense silence passed, and when Louis didn’t relent, Henry scoffed and continued on— finally. “I’m… sorry about him,” Louis sighed, looking at you again. “He’s a bit old-fashioned.”
“I get the impression that you are, too,” you noticed, and he was impressed by your perception.
“Well, I suppose that I am, yes,” he agreed, “but more just aesthetically. He can be irritatingly conservative, even concerningly reductive at times. I’m sorry that he called you a lesbian.”
“Oh, it’s not insulting to me,” you assured, “and I’ve been accused of much less accurate things. And, I mean, basically everybody’s parents are irritatingly conservative.”
Louis was confused by the non-sequitur until he realized the nature of your assumption. “Oh! Henry isn’t my father, actually,” he corrected, “my parents, um… they’ve actually passed away.”
“Oh, I’m so sorry,” you sighed.
“It’s alright, that was a long time ago,” he shrugged. “Anyway, Henry is just my roommate. And maybe a bit of a mentor— he’s taking me to the opera, I’d never been to one before.”
“What do you think?” you asked.
“It’s amazing,” he beamed. “The performances and the atmosphere— and I don’t know if getting asked out by pretty girls during intermission is normal, but… I like that part, too.”
You smiled and, right on cue, the lights dimmed and brightened a few times.
“Guess we should go back to our seats,” Louis decided, looking up at the chandeliers for a moment until they’d returned to normal.
“Not before I get your phone number,” you reminded him.
“Right, uh—” he stammered, not sure how to transfer this information until you simply handed him your cellphone with the ‘new contact’ screen open. Yes, that seems like a good way to go about this…
His thumbs were a little shaky as he tried to select the numbers on the tiny keyboard, and he had to go back more than a few times to correct mistakes. However, thankfully, he managed to get it in eventually and hand the device back to you with a smile.
“Alright, I’ll call you later,” you smiled, glancing down at the screen for a second, “Louis.”
Oh goodness, you’d just learned his name from the contact— he’d been so flustered, he forgot to introduce himself. And he didn’t know your name, either. But he didn’t need to; he returned to his seat for the second act feeling like he was floating on a cloud because you were going to call him. And you were going to ask him out for coffee, apparently. This night couldn’t get any better.
~
He was probably overdressed for a coffee date. But you’d called him cute last time he wore a suit, so he was wearing a suit again if just to chase that high.
He’d arrived unreasonably early and already gotten through a latte— he was probably going to drink too much coffee and end up all jumpy and anxious. Actually, he was pretty jumpy and anxious without any coffee at all. So, more coffee couldn’t hurt too much.
Fifteen minutes before you were due to arrive, he was already looking at the door every time the bell chimed, watching business people come in with briefcases and laptops, couples and friends laughing together. He thought maybe he should go to the bathroom before you got here, but then, what if you came in while he was in the bathroom and didn’t see him so you simply left? Yes, perhaps best to just wait.
Ten minutes before, and he was trying not to bounce his leg while he sat, but he kept doing it without noticing and then suddenly noticing and having to stop himself. He stirred his coffee for no good reason.
Five minutes before, he looked at the door when the bell chimed, like he always did, even though he knew it wasn’t you— and then it was you, finally. His heart skipped a beat when he saw you: you were wearing a dress, a green one with buttons down the front. He was amazed, and envious, that you could look so good in men’s or women’s clothing. Not only that, but the dress had a vintage sort of look to it, and he could just imagine how good the two of you would look together. People on the street and in this cafe were going to see you with him and know that you were on a date… it was thrilling to picture.
He stood up, catching your attention as you smiled at him. Nodding, he grabbed your chair and pulled it out for you until you were close enough to sit down. “Thank you,” you smiled as he pushed it in for you as well before returning to his own seat, “so chivalrous.”
“Well, I try,” he hummed.
Over your first cup of coffee and his third, he learned so much more about you— your family and what it was like to grow up with them, what brought you to New York and what you hoped to accomplish here, your favorite pastimes, your pet peeves…
He tried not to overshare about himself, even though you pressed to know more. I’m just not as interesting as you, he insisted, but you weren’t so easily dissuaded. Really, he was just afraid that if he started talking too much about himself, he’d say too much and say the wrong thing and you’d look at him in that way people did when he said the wrong thing. Really, Louis didn’t like opening up to people very much at all. Maybe part of the reason he got along with Henry so well is that Henry was far too self-absorbed to ask anything too personal about Louis, preventing Louis from sharing the wrong secret and getting that dreaded glare.
When the coffees were depleted, Louis wondered if it was time to go back to his apartment. He didn’t want this to ever end, but he also didn’t want to keep you here longer than you wanted, which were two obviously-opposing goals.
“Maybe I should get back home soon,” he announced aloud, hoping that that ‘maybe’ would leave room for you to say he could stay longer. But he also braced for the possibility that you would tell him he should go, and that this would be the end of your first date. Instead, you said something he didn’t expect.
“Do you mind if I walk with you?” you asked.
He felt his face warming slightly, and hoped you couldn’t see it if he was getting flushed. “I should be the one walking you home,” he noticed.
“Don’t overthink it,” you winked, and he decided that for possibly the first time in his life, he was going to take that advice and not overthink it. Or at least, he was going to try not to.
Hands stuffed in his pockets, Louis followed by your side as the two of you strolled along. The conversation continued, though it drifted away from personal matters and onto books and stories; you seemed impressed that he was a former assistant professor of English, not focusing too much on the former part like most people did. (He was just relieved that you didn’t ask why he’d been let go.)
This was normally a rather long walk, but talking with you made it go by in a blink— in fact, he was even a bit disappointed when he realized you were standing right in front of his building.
"This is me," he informed you as he gestured to the aging brownstone.
"Oh," you smiled, craning your neck to look up at the building.
"That's my window," he pointed upwards.
"Seems like you have a nice view," you noticed.
"Not as nice as the view I have now," he offered as he looked at you, and you playfully rolled your eyes.
"Wow, that's cheesy," you grinned. "Embarrassingly effective, but cheesy. Can I come up?"
It took him a second to realize you were asking to be invited into his apartment. Slightly overwhelmed but not quite stupid enough to let this opportunity pass, he nodded and you followed him to the steps as he opened the front door for you.
A sizable stair-climb later, he guided you into Henry's foyer.
"It's a bit cluttered, but, that's all my roommate's stuff," Louis explained as you stepped inside and looked around.
"He has an eclectic taste," you stated the obvious.
“I sleep in this little spare room here,” he continued, opening the door to it, only to find he’d left it in total disarray with a pair of boxers crumpled on the floor; he made a dash to throw everything out of the way and half-make-up his bed, but you appeared behind him and snorted out a little laugh. “I, uh, didn’t know you were going to come up,” he defended himself.
“But were you hoping that I would?” you asked, and honestly, he hadn’t even thought that far ahead.
“Yes,” he lied. Not that he hadn’t hoped you’d come into the apartment someday; it was just that he was really just trying to survive one thing at a time, and a coffee date was challenge enough for him. Now you were here and he’d barely managed to make his room presentable and—
He felt your hand on the back of his neck, and when he turned to look at you, you were already moving in to kiss him. Even though he was flustered by your forwardness, he gladly met you halfway and kissed you back. You tasted like spearmint chapstick and root beer— and most of all you tasted like you, and he heard himself just barely hum under his breath as he moved his lips with yours. It was sudden, and unexpected, but still perfect, even though he’d wished he had the confidence to kiss you first. He wanted to be romantic about it, and gentlemanly, so he planned to not even try to kiss you on the lips until the end of the second date; the plan for tonight was just a kiss on the cheek after he dropped you off at your door. This was… not the plan. Not that he was complaining. But he was a little confused.
Your hands rested on his shoulders as you breathed slowly through the kiss, tilting your head slightly. He knew it was weird, but he kept opening his eyes to look at you. You just looked so beautiful like this, so up-close with your eyes shut gently while you kissed him. He realized that his hands were still hovering around you, and he hesitantly lowered them to rest on your waist— though he still kept the pressure incredibly light, in case grabbing you too hard would be inappropriate. He heard you let out the smallest sigh and it made his heart swell.
Carefully, your tongue started to prod at his lips, and his heart started to race as he let you deepen the kiss and move your tongue alongside his.
As your hands started to move, slowly, down his chest through his blazer, he felt his own grip on your waist tighten. The fabric of your dress was so soft and delicate— so were your lips, and your tongue was gentle and sweet and exploring his mouth in a way that made his knees a little weak.
The kiss was suddenly a little hungrier, a little rougher, a little more desperate; both of you were breathing heavily, and when he instinctively pulled you closer, he heard (and felt) you moan. “Louis,” you gasped into the air between his mouth and yours, and he couldn’t help but let out a small whimper at how perfect his name sounded when you said it like that.
His heartbeat raced even faster as he felt his trousers getting tighter. The realization that he was getting hard made him instantly anxious— maybe it was okay to get a boner right now, maybe that was where this was going… and yet, that idea somehow made it even worse. All at once, the self-hating fears flooded his mind. What if I can’t do it right? I don’t know how to do this— I can’t do this. She’s going to know something’s wrong with me, something is so horribly wrong with me…
Breaking the kiss, he stumbled back suddenly. You started to follow him for a second, but stopped. “Are you okay?” you asked.
“I think I should walk you back to your apartment,” he decided suddenly, and you looked at him with confusion.
“Okay…” you agreed awkwardly. “Did I do something to upset you? I’m sorry if I did, I promise that I didn’t mean to.”
“I just,” he began, starting over again. “It’s not you. It’s just that— I don’t know how far you wanted this to go, but Henry says I’m not allowed to have sex in the apartment,” he explained, twisting his fingers in his hands.
“Your landlord decides if you're permitted to have sex?” you asked incredulously, raising your eyebrows.
“He is also my roommate, so, he has some say in it…”
“Listen, Louis— if the first date is too soon for you, that’s fine,” you assured.
“Well, that’s part of it,” he admitted. “I don’t want to take things too fast. I’m… trying to be a gentleman.”
You smiled slightly, stepping closer to him. “Oh, Louis, you don’t have to worry about that,” you purred. “You’ve been so sweet and respectful, it’s been wonderful… but to be entirely honest—”
He swallowed thickly as you got close enough to rest your hand on his lapel, looking up at him through your lashes. You were so pretty he didn’t know what to do with himself, and the look you were giving him could only be described as ravenous.
“— ever since I saw you, looking at me from across the ballroom, dressed up in your suit looking like the perfect gentleman,” you continued, clutching his jacket suddenly, “I’ve been thinking about all the very disrespectful things you could do to me.”
His eyes went wide. He was certainly out of his depth now— if you were looking for a dominant man, someone to ravish you, he was going to be totally useless. Of course he couldn’t give you what you wanted, he should’ve known better, he should’ve never even agreed to go out with you when it would only end in disappointment for both of you. You wanted a real man and he was just—
“Hey,” you soothed, apparently noticing the panic on his face, “don’t freak out. Nothing has to happen tonight. But, I’m sort of out on a limb here…”
“I’m sorry,” he sighed, “it’s not that I’m not attracted to you. It’s just that I want this to be perfect— you deserve nothing less. You deserve flowers, and candles, and not this tiny awful apartment when Henry could come back at any moment— or come back after and make some horrible comment about how it smells in here…"
You laughed, and he stopped his ramble to sigh slightly.
“I just think it might be better if we get to know each other a little better first,” he concluded. I just think I should give you a chance to realize I’m not what you think I am, so you can save yourself the trouble, he wished he could say honestly.
“Wow,” you nodded, “I know I pegged you as a little conservative but… this is new.”
“Please, don’t take it personally,” he began, but you shook your head reassuringly.
“No, I mean, it’s kinda nice,” you clarified. “I think there should be more guys like you out there— you know, traditional. You’re a dying breed.”
Guys like me, huh? Louis thought to himself, resisting the urge to laugh. If only you knew.
But you didn’t know, which was how he wanted things to stay— he didn’t want anyone to know.
~
In the last month, Louis had made two Herculean accomplishments: one, he’d managed to survive four more dates with you, with such success that each ended with the promise of another; two, he’d managed to keep your libido at bay in a month of dating. You never seemed disappointed, and by now you’d made it clear that you were waiting for him to make the first move when he felt he was ready. The problem was, he couldn’t imagine how he was ever going to be ready for you to see him without all his clothes, his image, his pretense. He had this strange feeling that if you saw him naked, you’d see right through him, see everything about himself that he locked deep down and far away. And he’d rather just keep making out than go further and lose you for good.
“I’m seriously gonna run out of vases, Lou,” you sighed with a smile once you’d opened your door, finding him waiting to pick you up with yet-another small bouquet of flowers. “And my house is turning into a plant mausoleum!”
“Next time, I’ll just bring you a new vase, then,” Louis offered, and you laughed; he loved your laugh, and when he was around, he heard it surprisingly often. You told him before that girls laugh at a guy’s jokes if they’re attracted to him, whether or not he’s funny; Louis didn’t care if you really thought he was funny, or just thought he was attractive— both were higher praise than he ever expected from someone as both as you.
“I’m not ready to go yet, sorry,” you apologized, walking quickly around the apartment as he followed you into your bedroom. “I can’t decide what to wear.”
“You look good in anything,” he insisted, sitting down on the side of your bed.
“Well, I wanna feel good too, and it’s so cold out,” you explained. “You can wait out here and I’ll be dressed in a second, alright?”
He nodded, and you smiled as you disappeared into your walk-in closet and shut the door.
Twiddling his thumbs, Louis entertained himself by looking around your bedroom; he’d been in here before, so he recognized some familiar objects and noticed the new trinkets lying around. There was a necklace on your bedside table, and a lone sock on the floor—
His breath caught slightly when he saw some clothes strewn over the corner of the bed, some you must have been trying on earlier while trying to pick what to wear. Of course, it wasn’t just momentarily-worn clothes that got his attention… it was the bra. Purple lace, thin straps, and a little silver heart charm dangling from between the cups; Louis was all but salivating looking at it, imagining how nice it would be to wear…
“How’s it going in there?” Louis asked you through the door. “No rush or anything, our reservation isn’t until 7…”
“This dress has, like, a billion buttons,” you replied, “it’ll be a while, sorry… I can get you some water or something?”
“No no, it’s fine,” he assured, and he felt his heart begin to race as he wondered if he would have enough time just to hold it for a moment and see how it felt.
Glancing from the garment to your closet door and back a few times, he gave in— he hopped from the side of the bed over to the end, glancing over his shoulder at the closet door one more time before picking up the bra. He sighed slightly as soon as he touched it, feeling the details of the lace under his fingertips. There was a long vanity mirror propped up against the wall, and he chewed his lip nervously as he looked into it. He was there in the reflection, in his suit with his hair slicked back, and he had one of those moments where he was surprised to see himself. He wasn’t ever sure what he expected to see in these moments, but it wasn’t the young gentleman he was looking at now.
He held up the bra to his chest, over his jacket and shirt, but it wasn’t really doing much for him with all these clothes in the way. He longed to see that lavender lace on his bare skin, he wanted to feel it under his shirt, he wanted to be pretty… pretty like you.
You’d look amazing in a bra like this, he was sure. He’d had thoughts of that nature late at night, staving off his physical interest in you in order to keep chaste lest you see the confusion he was hiding under his clothes. He’d imagined looking at you, touching you, being with you in a way his instability made impossible for the time being. In that moment, he couldn’t decide if he’d rather see you in something like this, or ditch you entirely and wear it himself.
See, that was exactly why he felt he wasn’t ready to take things further with you. He barely had any idea who he was, let alone how to be the person you wanted. The man you wanted. Louis was pretty sure he was a man— at least, most of the time— but he clearly wasn’t much of one, sitting here now with your bra held up to his chest.
He dropped it into his lap with a sigh. This little adventure hadn’t been very satisfying like he thought it would; he just needed a little more…
Before he even really had the thought, he watched himself in the mirror as a shaky hand started to reach up and unbutton his shirt. As he wondered if he was really going to do this, he slipped off his jacket and set it aside and before he knew it, his shirt was off too.
She said her dress had a billion buttons— I’ll be quick, I’ll only wear it for a second— he told himself, rushing to get this over with quickly. Maybe this would be enough to hold him over for a while; maybe he could do this, get it out of his system, and take you out tonight feeling much more normal and much less tempted to look at your clothes as you sat across the dinner table from him and wonder if he could wear them as well as you do.
Shirtless, he tried not to linger his gaze too long on his body— he didn’t care for it much, too lean to be masculine and too straight to be feminine— as he slipped the straps of the bra up to his shoulders. It was awkward, reaching around to try to clasp the back, but he eventually figured out how to do it and managed to get all three hooks latched (though, unbeknownst to him, one was latched on a different row than the others).
Adjusting it again now that it was clasped, he sighed and looked at his reflection again. It looked good— it felt good— but it didn’t look or feel quite… right. There were cups that he had nothing to fill, and the straps crossed over his broad and bony shoulders that were nothing like your smooth and delicate ones; the only part he really liked was the silver heart charm that dangled over his sternum… he toyed with it between a finger and thumb and smiled to himself, thinking that it was sort of like wearing a bra and jewelry at the same time.
No, it wasn’t perfect, but it was still nice, and he reached up to tuck a longer strand of his hair behind his ear— it wasn’t quite long enough, so it fell forward into his face again, but he had already forgotten that again as he turned slightly to try to see how it looked in the back.
It was right about then that the door behind him opened, and in that reflection he saw you staring out at him wide-eyed and open-mouthed.
He whipped around, blood pumping and eyes already starting to water as he fought to try to get off the bra, but obviously it was far too late. “Oh! I was just— I wasn’t— this isn’t—” he began and restarted several explanations, never settling on one for long.
“Louis,” you breathed, “it’s… it’s alright.”
“I didn’t mean to— wait,” he choked. “Alright?”
“Yes,” you agreed, stepping into the room with all the hesitance of one approaching a startled deer or something, “you can slow down, and just… tell me what’s going on.”
“I… I don’t know that I can,” he sighed, arms shaking a little where they self-consciously crossed his bra-clad chest. “I can’t explain it.”
“Well, maybe you can just start by telling me if you’re gay,” you suggested, “and that’s fine, I wouldn’t have a problem with that— except that, well, the problem that we probably couldn’t date anymore. But I would understand, of course. I’d be a little hurt if I was always just your beard, but—”
“I’m… not gay,” he interrupted. “I don’t have an interest in men… I like women, I’m fascinated by women, it’s just…”
“Sometimes you want to be one?” you wondered, finishing for him. “Are you, maybe, one?”
He glanced away. “I’m not sure. I don’t think so.”
"You just wanna look like one?"
"Something like that," he breathed. "You're just so pretty and— I wish I was pretty. Soft, and smooth, like you."
“Louis,” you cooed sympathetically, reaching up to touch his face, “you are pretty. And soft. I love that about you— I think it’s sexy.”
“Oh, uh—” he choked, but thankfully you interrupted him because he’d started talking before he knew what to say.
“Did you… start seeing me, because you wanted to wear my clothes?” you asked nervously.
“No! No, this has nothing to do with how I feel about you,” he assured. “This is just about how I feel about myself.”
“And how do you feel, now?” you pressed.
“Well, a little terrified,” he admitted, “and… and sort of pretty…”
“You are,” you agreed, and he started blinking rapidly, reaching up to cover the side of his face with his hand.
“Oh… really?” he mumbled.
“Yes, of course,” you insisted. “It’s just, I wish you would’ve asked first, because— well, you’re sort of stretching it out.”
“Oh, I’m sorry,” he mumbled, starting to try to peel your bra off hastily.
“No no,” you cooed, stepping up and stopping him with hands delicately placed on his shoulders. You reached around his back and undid the clasp for him, and he reached forward to let you slide the straps down his arms. “Now we can go find you one that fits.”
~
He sighed and let his eyes fall shut as you lightly swiped the brush over his cheek; it turned a little more peachy with each go of it, and you moved to the other when the color threatened to overpower his skin tone.
“What’s next after this?” he asked.
“Mascara,” you replied, voice sort of lilted as you focused on your work.
“Isn’t that uncomfortable to put on?”
“Well, you get used to it,” you shrugged.
“I think I will,” he agreed with a little smile.
“Your lashes are already really long,” you noticed, “this is really just to make them a little darker.”
“Right, okay…”
He managed to get through the mascara without his eyes squinting or watering, so his lashes stayed intact as you moved on to the finishing touch. Already you could see that he was getting excited, even quietly confident if still characteristically shy. Your heart hurt to imagine that he’d been hiding this from you for so long, apparently thinking you might actually reject him over something so trivial.
“Alright, which color do you want?” you asked as you held up three different lip glosses for him to choose from. You could tell just in the way that his eyes moved quickly over the tubes that he was hesitating. He lifted his hand but stopped for a second. “Whichever one you’d like,” you encouraged softly.
That seemed to give him the courage to reach up and tap his fingertip on the baby pink one with the gold glitter; you smiled and set the other two down before unscrewing the cap.
“Hold your mouth open just a bit,” you encouraged, making the expression you wanted him to so he could copy it. When he relaxed his lips just right, you ran the doefoot applicator over the bottom one first. “Oh, this color’s pretty on you,” you noticed, and you saw him struggle not to smile since he knew he was supposed to stay still while you applied the gloss. It was rather sheer, but with just enough color to really bring the whole thing together, especially with the blush which matched it well. “Okay, go like this,” you instructed as you pressed your lips together, and he copied you again. You moved the product around on his top lip just to make sure it covered all the right places, and finally you sighed as you felt your work was done.
You stood up and stepped back, and his eyes went a little wide as he straightened up; you could imagine he felt kind of strange and vulnerable being examined like this. He hadn’t even seen himself yet and here you were staring at him, but it was only because you were feeling rather proud of yourself. You kept the look subtle, not wanting to make him look gaudy or dramatic— he had so much natural beauty already, you just wanted to accentuate it slightly. He didn’t need foundation at all with such even skin, so you’d just put a little concealer under his eyes to brighten them up; and then it was just brown eyeliner and a clear gel for the brows (maybe someday you could talk him into tweezing them a bit but you knew that was a hard sell) before the finishing touches.
“Louis, you look great,” you beamed. “Not to brag or anything, but I’m sort of a genius.”
“Can I see?” he asked nervously, and you grabbed a hand mirror to give him as you sat by his side on the bed again. He found the angle to examine his face, and for a second or two you really couldn’t tell what he thought because his expression stayed blank. You could tell, finally, that he was happy by the way his fingers traced over the edge of the mirror while he gazed at himself.
“How do you feel?” you asked him softly, leaning in a little closer so you could see his reflection over his shoulder.
“Um, well,” he mumbled, “I think you did a nice job.”
“That’s not what I asked,” you noticed.
“I feel… beautiful,” he decided.
“You are beautiful,” you assured, and you caught his stare moving to your face before he set the mirror aside and looked down into his lap. “How do you feel in your new outfit?”
“I wouldn’t call it an outfit,” he chuckled awkwardly. “I mean, I couldn’t wear this out…”
Well, no, that isn’t the point of a lace bralette-and-panty set. “You could wear it under something,” you suggested, “and nobody would know. Except for you and I, if you told me.”
“Oh…” he breathed, and you spared a glance down to his panties and noticed them a little more… full, than usual, and couldn’t help but smile to yourself. The conversations you’d had about this with him had left it somewhat ambiguous if the desire to crossdress was sexual for Louis. It seemed like it was something that could be a bit of both, which made sense considering you absolutely had days where you hoped to dress in a way that would attract sexual attention, and other days where you wanted to look nice for much more personal reasons. Really, it seemed as normal to you as anything, even if Louis was so fearful of it. Maybe it was conquering his fear and quenching his desire all at once that was arousing him.
“Can I ask you an important, personal question?” you asked, and Louis nodded. “Are you a boy, or a girl? Right now, specifically. Neither or both are also acceptable answers, of course…”
“I’m… a boy,” he decided, “still. I just feel nice being a boy that sort of looks like a girl.”
“You should feel nice,” you agreed with a proud hum. “You’re a very pretty boy.”
He cleared his throat and you could see him getting flushed even with the blusher on.
“You’re gorgeous,” you continued.
“Oh, well, I don’t know about that…” he trailed off.
“I do,” you insisted. “You’re the most beautiful boy I’ve ever seen… and this brassiere looks so nice on you!” Trailing your hand down over his neck and collarbone, you traced the tip of your finger around the lace crossing his chest. “Do you know what this is for, Lou?”
He shook his head. You lowered your voice.
“It’s to cover your tits,” you explained, and you could see the shiver run up his spine. You smiled proudly, moving to trace your fingers over the hardening nipples just barely obscured by the pink lace. “Are your tits sensitive?”
“Y-yes,” he stammered, sighing and letting his head fall back slightly; his lips, parted for a whimpered moan, looked so delicious with that gloss on them.
“Then say it,” you encouraged.
“My… my tits,” he gasped it out, “are so sensitive… touch them more, please…”
You took your hands and splayed them out to grab handfuls of his chest, and he moaned out loud, finally. “Good boy,” you breathed, “make all those pretty noises for me, it’s supposed to feel good.”
“Feels really good,” he agreed in a sigh. “It feels really good when you play with them like that…”
“You want me to do it some more?”
He nodded, and you chuckled.
“Mm, you know you need to be a good boy and say it out loud,” you purred.
“Play with my tits more,” he panted, “please? And… and maybe you could kiss me?”
You were getting desperate, too; all you could do was nod breathlessly as you used your free hand to hold his face and kiss him— and he’d never kissed you like this before, it was always so innocent and chaste before (at least at the start). And that was sexy in its own way, but this? Whining into it, opening his mouth wide right away and letting you push your tongue between his lips? Sticky and sweet from the lip gloss, hungry and sloppy? It was fucking perfect.
He chased you for more when you pulled back, you had to hold his shoulders to keep him from following you (even though you wouldn’t have minded kissing him longer, especially when you saw how gorgeous he looked wearing that heavy-lidded, open-mouthed stare).
“Oops,” you grinned as you saw the way the lip gloss had smeared. “I messed up your makeup… but you look even prettier like this. You look so needy and cute… and a little slutty.”
He swallowed thickly and glanced down, and when you followed his gaze, you saw why.
“Your cock doesn’t fit in your panties anymore,” you noticed with a prideful smirk. His erection had burst right out of it and was red and leaking at the tip, flexing independently against his stomach. “Do you want me to touch it, Lou?”
He blurted it out before you’d even really finished your question: “Please.”
A choked moan fell from his lips as you wrapped your hand around his cock and began to stroke slowly— he started to buck up into your palm already, desperate for more. You’d imagined Louis would be the eager type, but this was better than you ever could’ve hoped for.
“O-oh, wow,” he breathed, watching your hand move over his cock, “your hand feels nice…”
“Mhm?” you encouraged, focusing for a second on the tip to spread the precum there. “Oh, you’re getting a little wet, honey…”
“Hng,” he groaned, eyes falling shut as he leaned his head back, “keep going, please, please—”
“Shh, I’m gonna keep going, don’t worry,” you cooed, guiding him to lay back on the bed; damn, he looked good spread out on your sheets, just like you’d wanted him since you first saw him.
Leaning in, you kissed down his neck, making a detour along his chest to pull the bralette aside and tease his nipple with the tip of your tongue. He moaned loudly when you did that, squirming underneath you.
"That's my good boy," you praised, "make those pretty noises for me while I suck your tits. You need to teach me how to make you feel good, so tell me when you like what I'm doing."
You wrapped your lips around his nipple and suckled harder, carefully letting your teeth graze over the delicate bud.
"Ohh, like that," he blurted out, "I like that— please don't stop."
You smiled and did it again, feeling him shiver and rock his hips up into your hand again. Moving across his chest to the other nipple, you teased it through the lace for just a second before pulling the fabric out of the way and sucking again; you soaked in the sound of his panting turning into whines, and even bit down just ever-so-slightly harder until he yelped for a second. You soothed him with a wide lick over the dusty-pink nipple, starting to slowly kiss your way down his stomach.
He lifted his head up to watch you go down, but it must’ve been realizing what you were doing that made him drop his head back down with a groan. “Oh,” he sighed, and you smiled as you kept going.
When you (finally) sucked his cock, he moaned louder than you'd ever heard him do anything before, and you just had to stop to tease him. "You like the way I eat you out?" you noticed, and he whined at the way you described what you were doing to him.
“Yes— don’t stop, please, p-put it in your mouth again…” he begged. You met his gaze as you wrapped your lips around the head of his cock, bobbing your head and hand together until you found your rhythm.
You wouldn’t mind doing this all night if he kept making such lovely noises, but as they grew louder and louder, you realized he probably couldn’t take much more; you noticed him gripping your sheets in his fists and wondered if he was already trying to hold himself back.
Releasing your mouth off of him with a pop!, you sat up straight and started to get your own clothes off. “Oh,” he sighed as he watched you, and you smiled a bit as you watched his eyes trail over every inch of skin as you exposed it.
“Were you thinking about this?” you wondered. “Those nights you kissed me for a while and then left because you’re a gentleman— did you go home and think about this?”
Breathing quickly through his mouth, eyes following your body, he nodded.
“Did you touch yourself?”
He nodded again.
“You did? I did too,” you purred proudly, stripped to nothing and suddenly straddling his hips. “And— be honest— after you did that, did you feel bad? You wondered if something was wrong with you, thought you might be a pervert or something?”
After swallowing thickly, he nodded one more time.
You leaned down and brushed some hair aside that had fallen into his face. “Sweetie,” you cooed, “you don’t need to feel bad. You’re not bad, and there’s nothing wrong with you. Actually, you’re so good.”
“Really?” he breathed, and this time, you nodded. You gave him a quick, soft kiss on the lips, and then another on his cheek.
"If you'll let me, I'd like to make love to you," you whispered into his ear, seeing him sigh shakily and nod. "Say it out loud so I know for sure."
"Please make love to me," he whispered.
Sitting up straight again, you looked down at him proudly. He looked like he was wondering what he should do, if this was alright, and you did your best to soothe him. "Just lay back, baby, I'm gonna do all the work," you grinned. "You can be my pillow princess."
You chuckled as his cock flexed in your hand.
"Is that what you are, you're my princess? You look like one with your pretty pink bra on,” you winked. “Pull it down for me, show me your little tits…”
His whole face was turning pink enough to match the bralette as he hooked a finger into each triangle of lace and pulled it aside to put his chest on display for you.
“Good boy,” you sighed as you guided his cock to your entrance and slowly sank down.
The shock of the feeling made him let go of his bra and grab tight onto your hips, holding you still for a second, as if he couldn’t take it yet if you moved at all; that thought was so wonderfully filthy that you felt your insides flex of their own accord.
"Oh my god, Louis," you gasped, "you feel so good inside me… your cock feels so good."
He simply whined through his teeth, gripping your hips tighter. The mascara-coated lashes were especially obvious when he shut his eyes tight, which he did for just a second before his face went slack when you finally started to move, a louder groan falling from candy-pink lips. He whispered your name, tinted with awe, and you grinned proudly.
"You're so deep," you groaned. "Do you feel how deep you are? Oh fuck, I can barely take it…"
"I-I'm not hurting you, right?" he breathed, and you smiled as he opened his eyes to look at you with gentle concern.
"Oh, sweet boy," you cooed as you stroked his cheek for a moment, "no— you're making me feel so good… you're so good, Louis."
He sighed, like he enjoyed hearing that, but like he also finally believed you.
"Tell me how you like it, Louis," you encouraged, "tell me how to move to make you feel good."
He hesitated for just a second before he grabbed your hips and started to guide them in slow circles, making you both moan lowly. "Like this," he breathed.
"Fuck, it feels good for me, too," you smiled. "Will you come if I keep doing this?"
"Yeah," he sighed, and you moved your hips just a little bit faster. "Yeah, I… I'll come…"
Leaning down and resting your arms at either side of his shoulders, you kissed his neck as you rode him, loving how desperate his moans became as you did it. From then on it was all about trying to make him louder and louder, doing whatever you could to hear that sweet voice break as he cried out from pleasure. He was so beautifully sensitive…
His eyes rolled back when you teased his nipples while he was inside you. "Oh, my god," he moaned.
"Does that feel good, baby?" you hummed. "It feels good to have your little titties played with while I ride your cock?"
"F-fuck," he grunted.
"I asked you a question, princess."
"Yes! Yes it feels good," he sobbed. "It feels so good, please don't stop— fuck!"
“You’re close, huh, baby?” you noticed in a quiet voice, and he bit his lip as he nodded. “Are you trying not to come right now?” He nodded again; poor thing.
“I— I don’t want it to be over,” he explained shakily.
“Mm, I know,” you cooed sympathetically, “but I wanna feel you come, okay? I wanna see how pretty you are when you come.”
He hissed in a breath through his teeth, eyes shut tight, fingers digging into your hips again.
“Can you do that for me?” you pressed. “Can you be my good princess and come for me?”
He nodded, and you smiled.
"Come inside me, Louis," you encouraged, "it's okay, go ahead."
Instantly, he made a choked sort of noise and you felt his hips move up to bury himself completely inside you; his mouth fell open and you felt his cock pulsing, pumps of come filling you. With a contented sigh, you relaxed a bit on top of him. You admired how good he looked with his makeup a bit disturbed from the sweat he’d worked up, panting as he blinked his eyes open and stared up at the ceiling, each rise and fall of his chest making the bralette shift slightly over his skin.
Eventually, you rolled off of him, and you smiled when a slightly-sweaty hand reached out to hold yours. “Was it dressing like this and wearing the makeup that turned you on?” you wondered aloud.
“Well, that was part of it,” he admitted, without looking back at you, which you figured made it easier to respond honestly, “but really it was just all the attention you were giving me…”
You smiled and bit your lip slightly. “Baby, you don’t need to wear a bra and put on makeup to get my attention… you’re always pretty, dressed up or not.”
He met your gaze then, and smiled back at you bashfully.
“See, that’s the prettiest thing you can wear: that smile,” you cooed, and he looked away as he smiled even wider.
“Stop,” he whined, but in that cutesy way that just made you want to compliment him more. You held his face so he couldn’t squirm away when you gave him a kiss on the cheek.
“Come on, you’re gonna wanna wash that makeup off so it doesn’t get on the pillowcases— or break you out,” you explained, sitting up, “and we could both use a shower after that…”
But you ended up electing for a bath, rather than a shower, which you found more comfortable to share. You washed his face with a washcloth, then helped him lean back into the water to wet his hair so you could lather some shampoo into it. He looked so relaxed as you massaged his scalp and carefully poured the water over his head; he even laid his head on your chest at one point and nearly dozed off, until you reminded him the water was getting cool and you’d need to get out and dry off soon.
You didn’t remember deciding to go to sleep, you just woke up the next morning with Louis in your bed, cuddled up close to you even while fast asleep. You smiled as you examined his peaceful expression, realizing how exhausting it must’ve been for him to try to always play the part of a ‘normal’ guy. This was the first time you saw him truly relaxed— he was always thinking when you were with him, you’d been trying to get him to loosen up and act natural, and he’d tell you that he was being natural, but he was lying. You knew there was more under the surface… of course, you hadn’t known it was this, specifically. But you felt pretty lucky because of all the things it could be, it ended up being so innocuous— and, if you were being totally honest, you thought it was sort of hot, too. Not in a fetishizing sort of way, because it wasn’t specifically Louis’ complicated gender discovery that turned you on in itself… it was seeing him accept something about himself, seeing him more comfortable and more open, seeing him give in to desire even when you knew he was more than a little fearful of being different.
And he really did look good in the makeup; you could only take so much credit for that.
~
He had no idea this was an option: that he could find someone who accepted and embraced the things about himself he still didn't understand entirely; that you could take on a more dominant role with such gentleness, and relieve him of that pressure to be the perfect gentleman.
He still got to play the part, though; he picked you up from your apartment in his suit, with flowers for you, and you smiled and kissed him on the cheek. He held your hand and gave you his jacket if you got chilly. But when he needed it most, you took charge and he simply followed your lead.
After a while, he became brave enough to kiss you first much more, to touch you without asking explicit permission, even to ask you to help him put on makeup or pick out something new to wear. He learned to accept being a little spoiled by you, and stopped getting worried that you were doing too much of the work— because you insisted that you enjoyed it.
Over time, he came to appreciate that feeling beautiful actually had a lot less to do with women’s underwear and getting made up with your borrowed cosmetics. He felt most beautiful when he wasn’t wearing anything and you just told him that you thought he was perfect (which he still couldn’t quite believe, but he was trying); it wasn’t a matter of the way he looked anymore— it was the way you looked at him.
So, yes, he could still wear a suit out into the city and not feel horribly out of place; he could put on pretty underwear with you and not worry if he was a woman or a man or neither or both. Most impressively, he could be with you and not convince himself that any day now, you would figure out what he ‘really’ was and leave him. You did so much more than see him, you discovered him, and you always seemed to like what you found. Crazy enough, Louis himself was starting to like it, too.
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