Tony is 16 and at MIT and even here he's an outsider, just as he has been at every other school in his life. He copes by being the clown (it's expected anyway, because he's the baby and looks it) and by being tenacious (like a tick or a terrier, impossible to shake, always tagging along). Many of the older students think it's hilarious to get him drunk (he always plays it up for the audience; he can hold his liquor better than several of them) or try to convince him to hit on girls (they don't like it when he succeeds, so he's careful not to be caught too often).
He shows up at the frat party in a black buttoned shirt that's open far too low and tight-fitting pants, striped in red and black. He's already performing his part, even though he was doing equations and tinkering with code until five minutes before he left his dorm.
She's tall and blonde and eighteen and she unbuttons his shirt in the cool night air out in the garden, where it smells of roses and there are stars visible overhead. It falls to the ground and he never sees it again, but he does see her. Several times, and each time she steals little bits of him. A bit by discussing Asimov's Laws of robotics in bed, another by the way she touches his hair. By the way she talks to him like an equal – never a child and never an oddity - until he's in love for the first time. When she breaks it off (it was never really formal anyway), he builds a new robot prototype in three days without sleeping and then goes on a two-day bender.
At 23 Tony still looks like he's 19. Not like Rhodey who looks older than his years and acts it, too. His experience in the military has done things to him that make him exude calm and authority, while Tony is just a kid who doesn't know what the fuck he's doing with his life when he isn't working. He's only good with machines, not with people, something Obadiah never fails to remind him. He's deemed too immature for most board meetings and while he might be CEO of Stark Industries, his formal role is more like chief brain.
At least he has no problems getting laid or getting drunk - getting anything, in fact. Being a billionaire has its perks, and he's still not used to just how fucking awesome those perks are. Playing strip poker with three models (blonde, brunette, brunette) in the garden of someone's LA mansion is just a new and amusing form of foreplay now, and after that he can honestly say he's lost his shirt in a game of cards.
Costume parties are great. Especially when they're lavish, decadent, extravagant functions of the kind that only the eccentric Hollywood elite can put on, and which look like they are from a movie set. Tony loves this kind of thing. It's more effort than he cares to put into a party himself, but being there? Fuck yeah.
There are drinks and drugs and women, and he doesn't really care what he ingests or who he fucks, as long as it's fun. Tonight it's a hell of a lot of fun. Not least when he finds himself in the middle of a group of people, some of whom he knows are formally monogamous, and it's all about him. Because even here, he's willing to push things further in order to fascinate and attract, and it works to his advantage. It's still fun when he's running away from a few angry significant others. He's still laughing when he dives into the car, wearing only a black wig, and Happy drives off without saying a word.
The guy is not his usual type, and yeah, he has a type, although he doesn't discriminate if someone good comes his way. This guy is good, and he's so calm that Tony feels like a school boy with a respected teacher, even though he's nearly 30 now. This guy is shorter than him and has dark hair gone mostly gray, and he smells like whisky and cheap cologne. He picks Tony up at a bar and doesn't care who he is, but treats him like a lost puppy.
It's the first time someone fucks Tony like that, taking time and care and insisting on waiting till he's no longer drunk before even getting into his pants. All they do is tender and gentle, so different from anything since school. When he wakes up in the morning, the man is sitting in the next room, reading, and Tony wants to sneak out without him knowing, and he wants to go sit in his lap and ends up doing neither. He gets a very chaste kiss on the forehead before he's sent out into the gray morning, and feels like he might be worth it for once.
It was sex like Tony had never had it before, and he hides how much it affects him by burying it so deep down he forgets about it for many years. It isn't till several years later, when he's searching for that particular shirt (a wine red that really suits him), that he remembers. When he does, it floods him, vivid, strong, and fills him with such a sense of loss that he can't bear to wear that color again for another few years.
There's someone in his bed. He can't even remember her name and he knows she told him half an hour ago before they fucked. Now she's asleep, and he's out of bed again, restless and sleepless and listless.
Nothing is helping; not drinking, not working, not fucking. He's 30 years old. Technically speaking he has everything, but it feels like he has nothing because so little is solid, and once in a blue moon he can't shake that feeling, has to fight it off with all he has and all he can get.
He stands there, looking at her, wondering why he does this, if there's even a point to going on. A few minutes later he manages to find his pants and takes off, drives for hours with the top down as the sun rises to his right. He barely notices it, or how beautiful it is here. Everything feels distant and whited out. Around 8 am he sends Pepper a message about the girl and she doesn't reply, but he knows she's got his back. That's why he doesn't just swerve left, off the One, and into the Pacific Ocean.
He passes the routine medical check with flying colors, which means several things, all of them good. First and foremost that he keeps his pilot's license, second that he can get Pepper off his back for a while, and third that Rhodey will hopefully stop telling him he's burning the midnight oil too much. He's in better shape than he was last time he did this two years ago, probably owing to the fact that he's taken up martial arts alongside boxing with Happy.
The cute nurse is checking him out. Tony is very aware of that, although he can tell the guy is trying to hide it. But he's young and Tony has seen it all before, many times, and he knows sexual interest when he sees it. It's been a while since he fucked a guy, so when the nurse happens to write his number on Tony's receipt afterwards, Tony takes his hand instead. It's quick and hot and dirty and up against a wall and the guy gives the best moans when Tony thrusts into him. He's aware everyone in the clinic knows, but he also knows no-one will dare do a thing about it. So it really doesn't matter that he forgets his t-shirt.
Waking up in handcuffs isn't exactly pleasant. Especially not when they're metal and the weight of his arms are on them. Thank fuck he's sitting, or it would be worse – he could have had far more weight on. His hands are numb and he works his fingers to get circulation going again. He's not against bondage as such, it can be fun, but this isn't the kind he likes – mostly because he wasn't asked first.
Tony remembers having sex, remembers it was good, remembers passing out after, but he isn't sure why he's in this position. He's probably done something to deserve it, but fuck knows if he's done it now or ten years ago or more. That's the downside to being a playboy and running a company that's ruthless: people with grudges can come looking. He's pretty sure that's what's happened here. Further indications being that his clothes are nowhere in sight.
So he waits. His arms ache, he can't relax much like this, not without cutting off circulation again or risking damage to his tendons. When Happy finally comes looking for him it's such a relief that he's having trouble keeping his facade in place. It isn't till he's home again, hours later, that he can curl up in his bed, and then he shivers for hours. He never finds out why it happened, and he never gets his clothes back.
The cross-dressing is on a dare, not that Tony's ever thought there was anything wrong with it. He'd done it once before, when he was young, and the result was a lot cuter then, but then that's true of his usual appearance too. It creates a stir when he shows up at the party like that, and he loves the hell out of shocking people.
Stripping down to his pantaloons is a complete impulse and he sees no reason to fight that idea, especially not when it results in him being dragged away by an incredibly hot dancer who kisses him like there's no tomorrow. She’s a go-getter; he likes that. They end up in the backseat of Tony's car, which feels strangely teenaged, but it's some of the best sex he's had in years. He should wear a dress more often if it inspires this kind of passion. When he returns home he's still dressed only in pantaloons, but losing the dress was worth it.
It's over now, he's dying. Only 35 and his life is spent. Tony Stark, the man who has almost everything and can make what he doesn't have, is dying and he can't fix it. This time there's no easy way out, and no matter what he does, he can't get away from it. Can't drink, party or fuck his way out of this one, though he tries. He can’t get close to the one he needs, to Pepper, so he tries elsewhere.
The woman has the same kind of red hair, but she’s not Pepper and she’s not enough. It doesn’t work. Pepper still snubs him when he tries to talk to her, tell her what’s going on, that he needs her help now more than he ever did. He’s gone too far, asked too much of her, and now she can’t hear him. He’s like the boy who cried wolf.
He can feel it getting closer, it's in his bones, his cells are slowly getting poisoned. He isn't sure how long he has left, but it isn't much. A few days, probably. Tony wonders what other people would do with their last days on Earth. He doesn't have the answer, but he knows he doesn't want to go. The arc reactor is a curse now, it started out as a blessing he didn't want, a part of his body that had been added without his consent, and he's only just begun to view it as something that belongs – and now it's killing him. Just when he was finally getting along with himself, when his soul and body had found a way to coexist, it's over. He tears his shirt in anger, staring at the useless, deadly palladium cores. All he can think is how horribly cliché it is.
No-one can quite compare to Steve Rogers. He marches into Tony's life, righteous and moral and admirable, and he and Tony are instantly on edge around each other. It's only slowly that they start to get along; grudging respect turns to mutual tolerance, which morphs into a kind of liking until they find themselves laughing together while watching The Simpsons on TV.
The first time Steve kisses him it's like nothing Tony can remember since his school days, it's so tender and even romantic. Steve's blue eyes are almost gray in early morning light, his skin is always warm. It's surprisingly soft, too (apart from on his hands where he holds the shield), and the way he touches Tony is slow and deliberate, and Tony feels so safe against him. They make love in Steve's bed the first time, and Tony hasn't been loved like that ever before, though a few have come close. It’s as gentle and slow as the kisses. Steve is so aware of his strength that he's over-cautious. All Tony can think is how much control he has over himself to do this all the time, even when he's hot and hard and they are both aching to come. Steve holds him close for as long as he wants, doesn't flinch at seeing the arc reactor, he even touches it with a soft reverence that makes Tony dizzy. When Tony has to leave in the morning, Steve tosses him his shirt so he doesn't have to walk through the mansion half-naked. Tony tosses it back and promises to collect it later.