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Steve hadn’t meant to find the pictures.
At the time, he was just trying to look something up, and Tony’s tablet had been the closest, so he’d grabbed that. When he was done, he figured a few minutes of Angry Birds would probably be pretty fun, so he poked around, looking for where Tony kept his games. The unlabeled folder had piqued his interest because it was unusual for Tony to leave things unmarked. So out of curiosity, he opened it.
Instantly, he realized his mistake, face growing warm as he looked as the thumbnail images. He’d been told that it wasn’t that unusual for people to have collections of erotic material—porn, his brain supplied—and it should come as no surprise that Tony had his own. He couldn’t help but wonder if Tony need this stuff because he wasn’t getting enough from Steve, but a quick check of the dates showed that no material had been added since they got together. He supposed that was okay, that maybe Tony just hadn’t deleted it yet.
Biting his lip, he looked around to make sure he was alone, and decided to look through the images.
Steve had been expecting pictures of women. He knew Tony liked both sexes, and he couldn’t blame him for wanting to look at women since he was with Steve now. But the pictures weren’t of women, they were of men...dressed up like women. Steve goggled at the pictures of smooth-shaven men, hair and makeup done like the classiest of dames he’d ever known and also like the most brazen of hussies, dressed in every type of outfit from lingerie to formal gowns to what Tony called bondage gear. This was what Tony liked? He couldn’t...Steve couldn’t do that. There was no way he’d ever look like the men in the pictures, most of them slim, willowy, and androgynous-looking. If someone tried to put him in a dress, he’d be a laughingstock.
“Hey, Steve, what’s up?” Tony asked as he walked up next to him and Steve was so startled he dropped the tablet.
“Whoa, didn’t mean to startle you.” Tony bent, grabbing the tablet before Steve could. He went to hand it back...and then froze as he took a quick glance at the screen. “I, uh...hey, listen, I can explain.”
“Do you like that?” Steve asked quietly.
“Yes....” Tony hesitated. “Yeah, but I like a lot of things, babe. Don’t worry about it. I’m sorry I didn’t get rid of this stuff sooner. Let me just....”
Steve reached up, catching Tony’s wrist in on hand as he moved to delete the file. “You don’t have to get rid of it.”
Tony raised an eyebrow. “Captain America’s cool with his boyfriend have a cross-dressing porn collection?”
“Steve Rogers is fine with his lover have erotica as long as he stays with him,” Steve muttered.
Pulling his hand away, Tony dropped down on the couch next to Steve. “You sure about that? It’s okay not to be. A lot of people aren't.”
“Yeah.” Steve said softly, nodding. “I don’t mind.”
“All right. I’ll keep it for now, just to prove a point, but say the word and it’s gone.” He bumped Steve’s shoulder with his own. “You’re too good for me, babe.”
Steve laughed, rubbing at the back of his neck, feeling the heat of the blush that remained. “That...that stuff,” he said, gesturing the tablet. “I mean, do you ever want me like that?”
“Steve, I like you exactly how you are. This stuff, it’s something I like, but what works for one person doesn’t work for everyone. I can’t exactly see you in formal wear and a pair of stilettos.”
“So you don’t mind that I’m not like those guys?”
“God, no, of course not.”
“Okay.” Steve leaned into Tony. He didn’t doubt Tony’s sincerity, or that he cared about him. The pictures just hadn’t been expected and they rattled him briefly. “I bet I coulda made a pretty good dame before the serum, though.”
Tony laughed, a warm, rich chuckle. “Oh, I don’t know. I’ve seen the film. You were small, I’ll give you that, but your face never screamed ‘dainty and feminine’ to me.” He wrapped an arm around Steve’s shoulders. “Probably would have looked killer in a garter belt and some stockings, though.”
They didn’t speak about the porn any further, though Tony had offered to get some high quality stuff if Steve ever wanted to do some exploring. Steve had turned him down, face burning with embarrassment. Even if he did want to look for something, he didn't want Tony hovering over his shoulder while he did it.
But no matter how hard he tried, he couldn’t get the pictures or Tony’s words about looking killer in garters and stockings out of his head. Perverse curiosity led him to the internet where he learned that not all men who dressed like...that did it to actually look like women. There were a surprisingly large number of regular men who apparently just liked dressing up in women’s underwear.
That...that probably wouldn’t be so bad. Would it? It would all be hidden under clothes and what no one else knew couldn’t hurt him. He could maybe do it as a surprise for Tony? He bit his lip. He’s seen underwear for women and there was no way that was going to look right on him, if they even came in his size. But the men in pictures all had stuff that fit, so obviously they had to get it from somewhere.
He waited for a day when the tower was mostly empty, and then retreated to his old bedroom before he’d begun living with Tony, and making sure the door was closed and locked before turning on his laptop.
One hour and some careful searches later, he had his answers. There were entire websites and businesses that catered to that lifestyle, and while some of the items looked frankly ridiculous to him, there were a few things that caught his eye, things that wouldn't look too silly. Lace and frills and soft colors might appeal to some people, but he couldn’t picture himself in them.
For several weeks, he debated whether or not to go through with it, ultimately deciding that no one had to know and he could always throw everything away if he changed his mind. He thought about what he would be comfortable with and what Tony liked—JARVIS had discreetly shown Steve some of Tony’s most viewed images. In the end, he settled on a pair of black lace shorts. They were close enough to regular underwear that they wouldn’t look too absurd, and the lace was about as far as frilly as he was willing to get. He chose a pair of backless ones, blushing the entire time, because this was for Tony and if Tony liked them, well.... He also added a black satin garter belt and sheer, seamed black stockings, with a little bit of lace along the edge, to match the shorts. That really only left shoes, because if he were going to do this, he should go all the way and it felt wrong to wear these things and then stick his feet in a pair of sneakers.
He had less success. Nothing he found was quite what he wanted, the shoes all looking too dainty for him to actually walk in—no matter what size they came in—or not quite right to go with the lingerie. He frowned, going back to the choices that seemed the least offensive.
“If I may, sir?”
JARVIS’s quiet, respectful tone scared Steve so badly he almost fell off the bed. “God, JARVIS, don’t do that, you almost gave me a heart attack!”
“My apologies, sir, but you seem to be having some difficulty finding what you require. I believe I may be of assistance.”
“Wait, you’ve been watching me?”
“Yes, sir. I always keep an eye on the residents of the tower, so to speak.”
Steve groaned, covering his face in his hands. He thought he’d been safe here, alone. He’d forgotten that with JARVIS that was never really the case. “JARVIS, please, you can’t say anything to anyone. Especially Tony.”
“You have my word, sir, that everything you do in private is held in the strictest confidence. I only spoke up because you appeared to require assistance that I believe I can provide.”
“Oh?”
On the screen, a new window popped up for a website he hadn’t visited. He poked around and realized that it was a site that made custom shoes, for both men and women. He looked at the options, blanching at the staggering cost. “I can’t,” he said. “I can’t. JARVIS, this is too much money. I’ll just get one of the other pairs.”
“Steve,” JARVIS said gently, using his name like Steve had asked him to. “You have more than enough money to buy these. I assure you, with the expense accounts Mr. Stark has provided each of the Avengers, you could buy a thousand pairs of these shoes and still not make a sizable dent in your accounts. And if you are doing this for Mr. Stark, then your comfort with the items is paramount and he would not object to any amount spent to attain that goal.”
Steve closed his eyes, rubbing at them with one hand. He was sitting in his bedroom, talking to a machine about buying custom made high heels so that he could play dress up for Tony. “All right,” he muttered after a long moment. “All right. Um, what should I get?”
He and JARVIS worked their way through the options until they’d settled on something Steve felt comfortable with—a pair of black leather pumps, with a rounded toe, half-inch platform, and heels that were sturdier than the sharp spikes Pepper wore, but not thick enough to look clunky. “I hope he likes these,” he breathed as he clicked the button to confirm his order.
“After having watched Mr. Stark’s habits for years, I can assure you that he will like them.”
“Thanks, JARVIS.”
“My pleasure, sir.”
~*~
The lingerie came in a matter of days, and Steve took them immediately to his room, shoving the items in the back of a drawer until he had the chance to try them on. When he did get to it, it was...odd. It took him a few moments to work the clasps for the garter, and it was simple enough once he figured out how they worked. The lace of the shorts was stretch, clinging to every curve and line, and the extra material in front ensured that his cock and balls were held comfortably snug. The shape of the clothing and the way it fit did feel odd, especially the sensation of having his ass bare, framed by the shorts, but he couldn’t deny that the material felt good against his skin. He didn’t keep them on for very long, just long enough to get comfortable with them, and then put them back away in his drawer.
The shoes took a month to arrive, and Steve had to be impressed by the final product. They looked ridiculously large, but they fit perfectly. He practiced walking in them, tottering on the four inch heels at first until he got the hang of it. He was steadier on carpet than on tile and hardwood, the fabric offering extra grip. Eventually, with enough practice, he was comfortable moving on all surfaces, even managing a little strut once he’d completely gotten the hang of it. All that was left was to...show Tony.
A few days later, another small package arrived for him, and he opened it cautiously. He hadn’t ordered anything else and had no idea what it could be. Steve blushed when he saw the razor, shave gel and lotion sitting in the box. “JARVIS?” he asked.
“Merely in case you wanted them, sir. Feel free to get rid of them if you wish.”
“Um, thanks.”
“You’re quite welcome.”
It took Steve another couple of weeks to work up the courage to actually use all the items he’d bought. He was still unsure how Tony was going to react, and he didn’t want to risk any of the others being around. Finally, Clint and Natasha were off on a mission, Thor went back to Asgard to visit his family, and Bruce flew out to the west coast to attend a weeklong seminar, leaving just Steve and Tony alone in the tower. Steve let Tony get engrossed in a new project, and then after dinner one night, went upstairs to his room to get ready.
He took a long shower, scrubbing himself down and cleaning himself out because he really, really wanted tonight to end in sex and he always liked being prepared. Then he got the toiletry items JARVIS had sent him and locked himself in his bathroom. He read the instructions carefully and set to work.
It seemed to take forever. He felt like he’d used half the can of shave gel and he went through two of the razor blades, but by the time he was done, his legs were completely bare and smooth from his ankles to the tops of his thighs. For a moment, he eyed his groin, wondering if he should shave that, too. Then he shook his head. No. A little trimming like Tony did would be fine. He had no desire to take a sharp blade anywhere near those bits.
He rinsed his legs once more, dried them off, and massaged a generous amount of lotion into them. Once he was done, he finally emerged from the bathroom to get dressed.
It felt...weird. His skin was overly sensitive, every touch as his legs brushed together or against the material of the sheets as he sat down felt magnified in a way he’d never experienced before. He couldn’t help from exploring just a little, shivering slightly when he dragged his nails along his thighs. Finally, he shook himself and reached for the garments. He slipped the shorts on first, adjusting himself where he’d grown slightly hard, and then put on the garter belt. Once that was in place, he slid the stockings on, attaching them carefully to the belt.
Steve stood, looking at himself critically in the mirror. He didn’t look like those men in Tony’s pictures, not exactly. He still looked like Steve, just a bit more...something. He just hoped that something appealed to Tony. Knowing it was now or never—and he wasn’t sure how he was going to explain the shaved legs to Tony if he went with never—he pulled on a pair of jeans and a t-shirt. They effectively hid the the lingerie, the only sign of it being his stocking clad feet. Taking a deep breath, he slipped the shoes on and headed for Tony’s workshop.
Moving through the main areas, he was very self-conscious of the garments hidden beneath his clothing, and the shoes on his feet. Even the extra few inches in height were enough to make things look different. If anyone else were to see him now, he’d probably die of embarrassment. And to make matters worse, the jeans rubbed against his legs as he walked. Even through the stockings, it was enough to get him a bit hard. He’d be lucky not to be sporting a full erection by the time he made it to the workshop.
The door wasn’t even locked. Steve walked right in, Tony’s attention completely engrossed in the holographic display he was standing in the middle of. “Hey, Cap,” he called distractedly, looking over briefly before turning back to his work. There was a momentary flash of disappointment as Tony failed to notice the shoes right away, but Steve pushed it away. He had to give the other man more than just five seconds. So instead of being annoyed, he wandered closer to Tony, leaning against a workbench and watching as Tony talked and muttered to himself as he worked.
Tony would glance over every so often, a habit he’d picked up when people began hanging out in his lab more frequently, to show that he was aware Steve was there and wasn’t ignoring him. He didn’t seem to notice anything was different until he went to reach by Steve to grab something and paused. He frowned, looking up at Steve, puzzled. “You seem...taller.” Before Steve could respond, Tony glanced down, then did a double take, his eyes flying wide open.
“Are you...no, you are. You’re wearing high heels.” He looked up, bewilderment showing on his face. “Steve, why are you wearing high heels?”
Not the reaction he was hoping for. Steve bit back his disappointment. “I thought you would...like it,” he mumbled. “I—sorry. I should have asked first. I’ll just go—”
“No!” Tony’s voice was strangled and he pushed Steve back against the bench. “Like it? I love it. Fuck, Steve, you’re incredible. This is because of the pictures, right? God, I didn’t make you feel like you had to do, did I?” He looked worried, almost panicked, and Steve couldn’t help but laugh.
“No, Tony, you didn’t. I couldn’t get the pictures out of my head and I thought maybe I could...try it.”
Tony groaned. “You’re too good for me. God, you look fantastic. I want to fuck you. Can I fuck you wearing the heels, Steve?”
Steve blushed. Tony was already this turned on and he hadn’t seen the rest of what Steve was wearing yet. He bent his head, capturing Tony’s lips in a kiss. “Yeah,” he breathed. “But I wanna go upstairs, to the bedroom.”
“Yeah, okay, that’s good. Hey, JARVIS, save everything, I’ll be back tomorrow.”
“Very good, sir.”
Taking him by the hand, Tony dragged Steve to the elevator and through their floor to their bedroom, touching and grabbing every chance he got. As soon as they were through the door, Tony was pulling at their clothes, shucking his own shirt and nearly ripping Steve’s off of him. He reached for the button of Steve’s jeans, but Steve grabbed his hands to stop him. “Tony, wait a minute.”
“What? Why wait? I want you now.”
“Yeah, but I have something else I want to show you. Just...have a seat on the bed, okay?”
“Sure.” Tony settled on the very edge of the bed, nervous energy apparent in the bouncing of his legs and the tapping of his fingers. Taking a steadying breath, Steve unbutton his jeans, unzipped the fly and pushed the jeans down, stepping out them quickly and only wobbling a little as he straightened up. He kicked the jeans to the side and then stood facing Tony, legs braced slightly apart, feeling horribly self-conscious again.
“Oh my god,” Tony breathed. “Oh my god, Steve, you...you....” Words failed him as he sat there gaping, but now Steve could see the definite bulge in his jeans, knew that Tony was a loss not because he was upset or repulsed, but because Steve had shocked him in a good way.
More confident now that he knew he hadn't erred, Steve held his arms out slightly, turning in a slow circle to show off everything, and the strangled sound Tony made when he saw the back of Steve’s shorts—or lack thereof—made him grin. “So you approve?”
“Yes. Yes, I very much approve. God, Steve, can I move now? Tell me I can move now because if I don’t touch you soon I might just die.”
In response, Steve held out his arms a little wider and Tony practically leapt from the bed. He pulled Steve into a bruising kiss, turning him and maneuvering him backward until he could push him onto the bed, kneeling between his legs once Steve had settled on the thick mattress. Leaning down, he kissed Steve hungrily, hands playing over the lace of his shorts, then the straps of the garter and finally running his fingers over the stockings. “You even shaved your legs,” he groaned. “I can’t believe you did this for me.”
“I’m glad you like it.”
“How could I not like it?” Tony laughed. “The gorgeous man I love and one of my favorite kinks? What could be better?” He moved back a bit. “What about you? Do you like it?”
“It’s different,” Steve said. He ran a finger over the lace. “I think I’m still getting used to it, to be honest. And I don’t ever want to wear the heels where everyone can see. But the rest of it...I’d do it again. It makes me feel...naughty,” he confessed in a small voice.
“You’re too perfect for words,” Tony laughed. He reached down to cup Steve's groin. “Would you wear the panties again for me? During the day? So that I’m the only who knows what a naughty, naughty boy you’re being?”
“Tony,” Steve gasped, cock fully erect by now and finally stretching the lace of the shorts.
“Let me help you with that, sweetheart.” Tony slid back, bending over until he could get his mouth on Steve’s cock. He kept his hands firmly planted on Steve’s thighs, stroking the sheer material of the stockings over and over while his mouth went to work. He didn't bother pulling the underwear away, just sucked and licked through the thin barrier of lace. Like that, he couldn’t swallow Steve down, but he licked and sucked along the head and shaft with more than enough enthusiasm to make up for it. Steve buried his hands in Tony’s dark, urging him on and trying not to clamp his thighs to hold the other man in place.
“Tony,” Steve groaned. “I’m close. Tony—”
He came, Tony sucking his release through the lace of the shorts. When he finally pulled off, the material was soaked, rubbing roughly against his cock and he whimpered as Tony stroked him. “Tony, please.”
“Okay, babe.” Tony’s voice was hoarse and he pulled away. “You ready for me to fuck you now?”
“Yes.”
“Then turn over, on your hands and knees.”
Steve did, bracing his legs apart and settling his weight on his elbows so that his shoulders were lower than his hips. Behind him, Tony made a rough noise as he moved back to shed the rest of his clothes and grab a bottle of lube. “Fuck, Steve,” he said, coming back and snapping a garter strap again. “You have no idea how you look.”
Just as Steve was about to tell Tony to get on with it, there was a light, wet touch against his entrance before Tony gently breached him. That was something Steve loved about Tony, that no matter how desperate he was, no matter how hard he was, no matter how rough their actual sex was, he was always gentle in preparing Steve. Steve had a pretty good suspicion that not everyone in Tony’s past had been as careful, but Tony hadn’t said anything, and Steve hadn’t asked. Instead, he settled back, and concentrated on the feeling of Tony slowly opening him up, first one then two then three fingers, scissoring and stretching, brushing over his prostate every so often while his free hand played with the undergarments, occasionally reaching underneath Steve to stroke his cock or pinch a nipple.
Steve flexed, just a little, pushing back against Tony’s hand in an unspoken signal that he was ready and wanted more. “Yeah, okay,” Tony muttered, and there was the sound of more lube being squirted, and then the slick sounds of Tony stroking himself. A moment later, he felt the blunt head of Tony’s cock nudging his hole, and sighed in satisfaction as Tony slowly pushed into him.
“Feels so good,” he muttered.
“Yeah,” Tony agreed. “God, you’re tight,” he hissed, slowly withdrawing and then pushing in again. He only gave it to Steve slow for a few more strokes before picking up the pace and slamming into hard enough to make Steve grunt. Steve pushed back against him, knowing he could take whatever Tony wanted and relishing the punishing pace.
One hand still firmly on Steve’s hip, Tony slid to other around to rub at his re-hardening cock through the lace. It was still a bit scratchy against the sensitive skin, the lace still wet, but it felt good. Steve hissed, biting his lip, and gave himself over to the sensation.
Tony stroked him back into full hardness while pounding into his ass, and Steve rocked back and forth into both sensations. He could feel Tony mouthing over his back, nipping at the skin along his shoulders. He could also feel Tony playing with the shorts, slipping his fingers under the edges, rubbing the lace, occasionally running his blunt fingernails over the stockings. The sensation of it was still so odd, so new that he found himself gasping and at the edge of coming much sooner than usual.
Steve came, suddenly, with an inarticulate cry, his semen soaking the shorts even further. And as he clenched around Tony, Tony’s thrusts stuttered. He tried to hold out a little longer, but didn’t last long, collapsing over Steve’s back, panting and gasping as his hips bucked a few last times before going still.
Steve let him rest there, able to hold his weight easily, even as blissed out as he was. When Tony finally did pull free, it was only to collapse on the bed next to Steve, who lowered himself and turned so that they were facing each other. By then, the mess in his shorts was cooling and he grimaced at the wet, sticky feel.
“We’ll clean up in a minute,” Tony murmured, pulling him close to nuzzle into his neck. “You’re fantastic. Thank you.”
“Thank you,” Steve said quietly, “for not making me feel like a fool.”
“Never, babe,” Tony muttered against his skin. “Whatever you wanna try, don’t care what it is, you never have to be ashamed and embarrassed around me. Never.”
Steve smiled against the top of Tony’s head. “Good to know.” He shifted to get more comfortable, and then grimaced again. “Can we take a shower now?”
Looking up with a bright gleam in his eyes, Tony asked, “Do I get to takes your panties off with my teeth?”
“Shorts,” Steve corrected absently. “But sure, if you want.”
“Then yes,” Tony replied, pushing Steve over onto his back. “We can definitely shower.”
~*~
Still damp from the shower, Steve walked out of the bathroom and into the bedroom to get some clothes. He paused when he saw the small decorative box sitting on his pillow, tied with a bright red brow. Puzzled he walked over and picked it up, frowning at its light weight. He tugged the bow free, lifted the top of the box off and then laughed when he removed the contents. A pair of red silk panties with lace on the sides. It had only been a few days; Tony wasn’t very patient. Or subtle.
Well, Tony had asked if Steve would wear the underwear beneath his clothes and Steve hadn’t said no, so.... He tossed the panties on the bed while he finished drying off and then selected his clothes. Then he slipped the underwear on, noting how well it fit, how cool the silk was, and it way it left the bottom half of his ass cheeks bare. Then he tugged his jeans and his shirt on and went to go find the others for breakfast.
The kitchen was ordered chaos when he entered, the entire team there and helping with breakfast, either cooking or setting the table. Steve took the stack of plates from Natasha’s hands and began to set them out when he felt a hand slip down the back of his jeans and a ragged gasp in his ear. “You like my present?” Tony whispered.
“I do. Now get your hand out my pants and go wash your hands,” Steve whispered back.
“Yes, sir,” Tony said, and pulled his hand out, but not before giving Steve a quick pinch.
Later that day, Tony cornered Steve against, pulling him into what seemed like a hug before he slid both hands down the back of Steve’s jeans to cup his ass. “So what do you think?”
“I think if this is going to result in your hands constantly down my pants, I’m not going to be wearing these very often.”
Tony made a face, but didn’t move his hands. “I’ll be good when we’re around the others, I promise. But seriously. Do you like this? Can I buy you more?”
Steve took a long look at Tony, at the raw desire and undisguised longing in his face. Tony was undoubtedly speaking the truth when he said he would never force Steve into something he wasn’t comfortable with, but it was just as clear that he liked it and wanted it. “Yes,” he replied, grasping Tony’s hips and pulling him closer. “You can buy me more.”
Tony shuddered against him. “Will you wear them out sometimes? When we go out? I admit, the thought of walking into a restaurant with you and sitting across from you for hours while you’re wearing your stockings and garters and pretty panties is really fucking hot.”
Steve’s breath caught in his throat and he forced himself to consider it, to think about what it would be to sit there, surrounded by unknowing strangers while underneath his perfectly normal clothes he was wore silk and satin and lace, the material rubbing smooth and tight against his skin. The image was arresting and he felt himself growing hard. “Yes,” he said thickly. “When we go out, I’ll wear them for you, Tony.”