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Gerri hasn’t said anything about the pictures. Roman’s been sending more and more of them, can’t help himself. It really irritates him somehow, that she hasn’t said anything about them, even to tell him to fuck off and cut it out. The more he sends that she doesn’t respond to, the more it itches at him, and the more he sends, which in turn compels him to send even more, which she then in turn doesn’t respond to, setting off an endless feedback loop of sexual frustration.
And Roman’s sent her so many different kinds of pictures, too. He keeps varying it, switching it up to try and unlock some secret combination of elements that will make Gerri snap.
He’s sent her tasteful images of just his boxer-clad bulge, or ones where he’s still wearing his business pants, his erection tenting the already-tight fabric obscenely. He’s sent her pictures where just the head of his penis is peeking out from his underwear and images where you can see his full shaft in all its average-sized glory. He’s sent her pictures where it’s soft in its less-than-average-sized glory because Roman is a little bit of a grower, thinking it might tickle Gerri’s pickle to see his penis all flaccid and pathetic and useless.
He’s sent her pictures mid-ejaculation and pictures where he’s already let his spunk start to dry tacky on his skin, spattered all over his little tiny bump of a belly. He’s sent her pictures from his walk-in shower and pictures from the bathroom just down the hall from her office.
Lately, he’s gotten into sending her pictures where he’s using a variety of toys. He’d sent her a photo of him fucking a fleshlight, right on the verge of coming hard into it disgustingly lubed up depths, with the caption “practicing hard for when you decide you want to let me give it a go”, and he’d just last night sent a picture of him coming untouched as he rode a huge dildo that he’d suction-cupped to the floor of his shower. He’d been sure that that one was going to get her. But nope. No reaction whatsoever, and she’d acted totally normal in the email she’d sent him at six AM this morning about the upcoming shareholder meeting.
It’s really pissing him off, how unflappable she seems. So he figures it’s time to change tactics. Maybe Gerri doesn’t just want a glimpse of the thrilling action going on inside Roman’s pants. Maybe she wants to see the whole package, so to speak. Get a preview of the full experience.
Roman steps over to the window of his bedroom, looking all those floors down at the city. This is one of his favourite places to do this; here or at the office. Close runner up is against his bathroom door, humping his dressing gown and wishing that it were Gerri’s, wishing that he’d had the wherewithal to have seized Gerri’s in Tern Haven, to have spirited it away with him somehow.
He holds his phone in his left hand, angling it as best he can to give her a clear view, and with his right hand he pushes down the sweatpants he’d slept in and pulls his cock out.
He’s still mostly soft, but Roman can fix that quickly enough when he’s alone like this, has a little grab bag of tricks that work pretty reliably when there’s not a heavy-breathing, turned-on girlfriend anywhere near him to mess up his vibe and throw him off his game.
He leans forward, forces himself to rub the head of his cock against the glass, the coolness of it stinging the sensitive head, the slight pain of it enough in and of itself to get Roman most of the way erect. He rubs it there a few more times, wincing, before he allows himself to back off enough that he can get a good grip on his shaft and start pumping. Roman doesn’t fuck around with slow strokes, doesn’t see the point in teasing himself or pretending that he’s going to be able to drag this out, because he never can.
He never really—thinks about anything while he masturbates. He doesn’t enjoy fucking, of course, so thinking about fucking someone or being fucked or watching other people fuck would honestly turn him off more than turn him on. He’d tried, early in this thing they’ve got going, reflecting back on one of his special conference calls with Gerri, replaying the names she’d called him, and that had worked better, but it’s not really the same as when she’s doing it on the other end of the line, when he can hear her disdain in real time.
It doesn’t really matter. Just the sensation is enough, fucking hard and fast into his fist, rocking against the window, looking down at how his useles little prick is leaking all over the glass, making a mess that someone else is going to have to clean up. For some reason, Roman’s dick has always leaked more than most guys’ do—don’t ask him how he knows, he knows because of military school and college and the bathroom at his gym and the back of a limo that one time he’d had to close a business deal in Johannesburg and all the other times he’s had a cock in his mouth—and he kind of hates it and it kind of turns him on. It feels wrong, somehow, how slick his hand is getting, like he’s getting all wet like a girl.
Oh fuck. That’s going to do it. Oh fuck—he thinks he’s been pretty silent so far, but he can’t help groaning and whimpering as he feels his orgasm start to crest and his vision sort of whites out for a second and when he comes back to reality, he’s made a mess sure enough, has ejaculated all over his hand and all over the window. His cock gives one last weak spurt when he sees how much disgusting fluid he’s spread all over, the tip flushed a dark red from how fast Roman had been rubbing it against the cool glass.
It truly does disgust him, to see it there—all bodily fluids disgust him, make him instinctively revolted at the indignity of having a human body that has to piss and shit and cum—but this, at least, disgusts him in the deliciously wrong kind of way, especially because it just reminds him how much of a fuck-up he is. Everyone wants him to be able to fuck, well, everyone apparently but the one person he might actually sort of be able to pull it off with, but he can’t. This is the only place his cum ever ends up, has ever ended up, running down his fingers, a waste, just debris to be wiped away with a wet rag. Never has Roman managed to leave any part of himself inside someone’s mouth or cunt (ugh, gross) but he could cum on every window and door in New York if given the chance.
Fuck, that was more intense than usual. Probably because he’d known he was doing it for Gerri, that she was going to be watching this, sooner or later.
He tucks himself back into his soiled sweatpants, and presses pause.
The video, from start to explosive finish, is forty-two seconds long. That’ll get Gerri if nothing else does, he thinks. Surely she won’t be able to resist the temptation to make fun of him for that, at least.
He types out “morning exercise”, attaches the video and goes about his morning ablutions, enjoying an extra long shower and feeling so good about things that he stops at the cafe he knows Gerri likes on the way into the office and picks them both up a coffee.
She doesn’t say anything about the video, doesn’t even look at him funny when he hands her the coffee with an exaggerated little flourish, but she calls him that night, the first time in over a week.
She doesn’t mention the video on the call, either, but he can’t shake the certainty that they’re correlated.
It doesn’t exactly dissuade him, and he starts sending the items even more frequently than before.