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The first time Roman ever tries jacking off is nothing noteworthy. He’s fourteen years old and gets a hand down his pants before realizing he has no idea where to go from there. Because maybe he was supposed to think of a hot girl sucking him off, or wrapping slender fingers around his dick, which, gross.
Either way, he promptly zips his pants back up and glares at the wall, an empty, dull feeling in his gut. This was fucking stupid anyways, he figures, because he didnt even want to right now. You’ve gotta be in the mood, or some lame shit like that
The second time is nearly a year later, and he’s decided what he was lacking was imagination. So now he has man's second-best-friend loaded up on a private browser, ready to play.
But no matter what mood he was in, this clearly wont work because he is looking at these naked people on his screen and all he can think is how dirty it all looks and how awful he would feel if anyone touched him the way the girl was touching the guy. And so he closes the tab, shuts off his computer, and washes his hands, the same empty-gross feeling in his stomach.
When his brother comes home for the summer, he makes sure to brag about his various and sundry sexual conquests.
The fifth time is after three girlfriends broke up with him since he “couldn't perform”. But maybe fifth time’s the charm, or some shit. That's what he tells himself as he boots up his computer.
He’s got a strategy this time- as long as he doesn't look at the screen, he can just use the sound, or something like that. It’s two girls in the video this time, so he can adequately distance himself from the situation. He clicks play and shuts his eyes, head tilted back, hand frantically unzipping his pants when-
“Dude”
He snaps back up, slamming the laptop closed and yanks his hand back. Natalie, or whatever her name is, Shiv's friend, is standing in his previously shut door, a look of disgust on her face.
Which was fucking unfair since this was his house and his room, and he should be able to let off a little fucking steam in peace, he tells her, red coloring his cheeks. But he doesn't go back to it after she’s closed the door and left.
He sort of, forgets. About the whole sex thing. It had been easy enough to make up fake girlfriends and just get gross enough about it that his family learned to stop asking. And it's not like he’d never had an orgasm- he could force his way past the disgust to enjoy himself for a good… five minutes? It would always end with a pit in his stomach and shaky legs, but it worked mostly.
Not long after his 19th birthday, he’s attending a gala, and a (kind of attractive?) dude is sidling up to him and quite possibly propositioning him. And well, fuck it! Maybe the problem the whole time had been that it was girls, right?
And when the guy, probably at least a decade older than him, slams him against the bathroom door, and he feels a stir of- something- low in his gut he feels so relieved.
But the guy starts talking to him and all of a sudden theres a fucking hand on his fucking dick and its so gross and he has no idea what to do because the guy starts sliding his hand up and under Romans shirt and Roman shoves him away.
The guy growls and starts to call him a “fucking tease” but he’s done and his hands are shaking so he snaps back, “at least i’m not a fag” and sees a fist swinging at his face.
His head snaps back with the force of the assholes hit and he catches himself on the counter. The guy storms out as he brings a hand up to his already tender cheekbone.
It’ll definitely bruise, but he can come up with a story- tell his dad it's from his siblings, tell his siblings it's from dad. They all know not to question him at this point. He sits on a toilet seat for the rest of the evening, trying to erase the feeling of the warm hands from his memory
He has a couple of people over the years he tries with. Nothing comes of it. For all he fucking knows everybody is exaggerating how good all this sex business is.
Years and years later, he really does have a girlfriend. And sure, he cant tell everyone he met her at a fucking… sex party after she sucked off his brother-in-law, but its a functional relationship. They don't have sex, or whatever, so it's good. For him at least. He’s pretty sure Tabitha would say something along the lines of “fuck no, Roman, this is not functional, we kissed once” but what the fuck does she know.
But, shit, he’s gotta make it good for her too because this is the longest relationship he’s had to date and he is not going to fuck it. So when he has the chance and they’re in bed he rolls over and says “hey, wanna fuck?” and she says “sure, Roman” because she doesn't have any faith in him, he crawls on top of her, ignoring the anxiety swirling in his chest.
He’s learned, at least, how to touch people. When youre fucked up and cant have real sex you make do with what you have, right? He runs his hands up her thighs, over her hips. He ignores the shivers down his spine as she moans and tries to stay calm when she touches back .
It's overwhelming, and not in the fun way he thinks it’s supposed to be. Every fiber of his being is on edge as he fucking, takes her clothes off, sizes her up. He thinks maybe he’s going to vomit when she looks at him and asks if he’s okay.
He gets up and runs away, like a coward, and then he washes his hands and stares at himself in the mirror. He is so fucked up
He has this… thing with Gerri that he’s not sure about. But there's no expectations on him, and while he wouldn't really call it sex, he’s getting something out of it. Not having to look at her is an added bonus- not that she’s ugly or whatever. It just makes it less real.
And it's so easy, when the words she says match what he’s thinking anyways. He is gross. Sex is gross, but he’s not going to say that. He knows well enough that if he admits to it she wouldn't understand, so he says nothing and calls her, or shows up at her room.
He supposes he’s kind of cheating on Tabitha, just a bit.
The tabloids would fucking love this one. They’d probably title the articles “fucked up billionaire cant get any pussy and has phone sex with fathers assistant while abstaining from even kissing his girlfriend”. Which is actually the thought that makes him realize, hey, this is not going to work. Maybe nothing was going to work.
He breaks up with Tabitha the next day, and he kind of ghosts Gerri. She can yell at him about it some other time. Maybe Tabitha can fuck Tom again, he doesnt fucking care.