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They’ve discussed this before. In their dirty talk. Greg has always chalked it up to being a heat-of-the-moment hypothetical that they’d never actually follow through on. Like many things in the past, though, Greg is wrong about that. He should have known when the topic kept coming up and with the way Tom got especially excited and his breathing hitched when Greg brought it up himself.
Now, Greg is in Tom’s new office and sitting in his lap.
“Okay, well, I am a bit concerned about one thing. The logistics, so to speak? My, uh, limbs are longer than most and—” Greg clears his throat when Tom shoots him an annoyed look. “—I’m just thinking, I might not fit.”
“And I think, Gregory, I’ve turned you into a spoiled pillow prince. You never want to put in any hard work.”
Greg rolls his eyes because it’s an unfair statement. Tom’s never had any complaints before. In fact, he’s always been eager to please Greg. The first time they fucked Tom didn’t hesitate to drop to his knees and eat Greg out. He didn’t even have to ask, though he knows if he had it would’ve been a yes anyway. Everyone knows that Tom can never tell him no, even after the blackmailing and multiple betrayals in the past.
“Don’t you want to celebrate with me? Wouldn’t it be fun to try something new, Gregory ?” Tom tugs at Greg’s tie and does that thing with his voice that he knows makes him weak in the knees. It's made worse when Tom leans in to whisper in his ear. “I promise I’ll make it worth it. Give you anything you want.”
“Yeah?” Greg’s already breathless and bucking his hips against him. He doesn’t even know what he wants to ask for. He just knows he wants—no, scratch that—he needs Tom.
He’s always been needy. It started well before they started their relationship. He’s needed Tom to look after him, to dress him up and feed him and show him the ropes. It only makes sense that all it takes for him to convince Tom to fuck him is a little batting of his eyelashes and a please, Tommy?
And okay , so maybe that’s what Tom means when he calls him a pillow prince.
“Yeah,” Tom says, just as breathless. He looks like he knows he’s about to get exactly what he wants, though. Greg wants to kiss the proud smirk on his face right off, so he does while rocking their hips together. It feels so good to get it almost hurts.
“Fuck, Tommy,” Greg breaks the kiss and whines, a little too loud given their setting. “Okay, okay.”
“Yeah? Gonna suck me off?”
Greg doesn’t answer. He just climbs out of Tom’s lap and maneuvers the chair backwards to give himself room. The fight looks like it’s going to be tight, but doable. He knows that he won’t have to be under there for very long if he does what he normally does when he gets on his knees for Tom. By now he’s learned all the tricks. He knows exactly what to do to get him off fast.
Once he sinks to his knees and squeezes under the desk, he works on Tom’s belt. His hands are shaky, more nervous at the idea of someone walking in on them than the idea of sucking Tom’s cock. That ship sailed long ago. Probably by the second or third time they slept together.
By the time he’s got Tom’s slacks around his ankles there’s a wet spot in his boxers. It’s not often that Greg is confident, but right now he definitely is. The sight of a desperate, needy Tom really does it for him. This gives him the upper hand, so he decides to take advantage of it. He closes his eyes and leans in to suck on the fabric. He savors the taste of Tom until he tastes only wet fabric.
Above him, Tom is leaning back in his chair and breathing shakily. If Greg opened his eyes he’d be met with Tom’s own half shut eyes. His chest heaves up and down as he’s teased, a hand rests in Greg’s hair. He doesn’t pull just yet. Instead he strokes his hair, gently tugs at it until Greg finally raises his head.
He gently tugs at the older man’s boxers. Tom raises his hips immediately, watching as Greg finally tugs them down to meet his slacks around his ankles. It feels a little ridiculous that his upper half is fully covered. Under normal circumstances (those being that they are not at work and are instead in their new shared apartment) Greg would complain. One of his favorite features of Tom’s body is his tits. It’s something Tom makes fun of him for, though deep down he is grateful. Said tits are a feature he’s hated on himself due to the reality of his aging. It’s nice that they’re appreciated.
Tom is quickly brought back to reality when Greg licks a stripe up his cock, then another down. Now Tom’s eyes are wide open, as is his mouth. He’s unable to close it at the sight of an eager Greg looking at him through his eyelashes. “You look so damn pretty like this. And you were so against it. Can’t believe you almost robbed me of this sight,” Tom can’t help but praise him.
Instead of stumbling through a reply, Greg drops his head down and takes the tip of Tom’s cock into his mouth. This earns him a more visceral response and encourages him to really do his best work. The aspect of Tom being unable to keep quiet and getting them caught makes it all the more exciting. Of course he doesn’t really want someone to walk in on him sucking dick, but the idea of it is hot.
Tom seems to think so too. He’s always understood Greg, almost as though he’s able to read his thoughts. “Look at you, sucking cock like a professional fucking whore. Christ , if the whole office saw you right now—but I bet you’d like that, hm? Someone walking in on you so eager to please me?”
Greg moans around his cock, then boldly takes him all the way in. Once the tip hits the back of Greg’s throat Tom has officially lost it. He’s got both of his hands in his hair, guiding him into a rhythm. To quiet himself, he pulls a hand away briefly, just to shove his tie into his mouth. The idea of being caught is one of the few things he wishes to keep a hypothetical. He's only just secured his new position. It would suck (pun unintended) to lose it so soon.
It’s a miracle that Tom hasn’t already cum.
Greg looks ridiculous in the most obscene, perverted way. Mouth stretched wide to fit Tom’s dick (because he was not kidding about it being the size of a red sequoia), spit dribbling down the sides of his mouth. Tom would tease him about being so sloppy if he didn’t find it so fucking arousing. There are times when he wishes he could snap a photo of Greg like this and cherish it forever. He can’t do that because of the risk of a leak. Other times he wishes he were an artist because then he’d just paint it. Sadly, there is a reason Tom stuck to business.
Not only is the sight enough to make a man lose his mind, the noises make it even more difficult. It’s like a porno that’s actually sexy and authentic. He’s called Greg his ‘little porn star’ before and it elicited a positive reaction. It fueled his ego mid-coitus and led to Greg riding Tom until the sun came up. They had to call in after that, Greg unable to walk and Tom unable to keep his eyes open afterwards.
Without any warning, Greg pulls his head up. Tom is annoyed, opening his mouth to make a snarky remark before he’s cut off. “Since you wanted this so bad, take what you want.”
Tom’s the speechless one this time. There’s a familiar lack of eloquence in his response when he says, “Huh?”
“Fuck my throat, Tommy.”
And there is no hesitation when Tom pushes Greg’s head back down to fill his mouth. He lets him adjust for a moment and waits for the signal for him to start. As soon as Greg looks up at him and gives him a slight nod, Tom tightens his grip on his head. He starts off by guiding Greg’s head up and down. If the sounds Greg made before were obscene, he wouldn’t even know what to call these new sounds.
He looks positively blissed out, like he was born to be on his knees and made to be used for Tom’s pleasure. His cartoonishly big blue eyes were rolled into the back of his head and his hands rested on Tom’s thighs. The sight is enough to have Tom gushing again.
“You— Christ —absolute fucking whore, goddamn temptress,” Tom hisses out. Greg opens his eyes, looking up at Tom as if to say say more, say more, say more , so Tom does. “You were fucking made for this. Made to suck cock—my cock. You are mine , you hear me?”
He pulls Greg’s head up by his hair and looks at him expectantly. “Yes, fuck, I’m all yours,” Greg sounds ruined and there’s no way he’s going to be able to finish the work day without any questions. Tom doesn’t say this, instead he pushes his head back down and holds it in place. Now, instead of guiding Greg’s head he’s thrusting into his mouth, fucking into it.
By now he knows Greg’s jaw must be getting sore. Just the right amount of time has passed for Tom to cum and not feel embarrassed about, so he lets himself teeter over the edge. His thrusts are getting sloppy and Greg reaches up to grab his hips and pin him to the chair. He takes over the work again, fighting through the lockjaw by slowing his pace and paying extra attention to every sensitive spot he can think of. All it takes is a couple swipes of his tongue across the tip of Tom’s cock before he shoots his load down Greg’s throat.
By the time Tom’s eyes are open again, Greg is back on his feet and swallowing what he can. What he can’t, dribbles down his chin and he catches it with his fingers to lick off. Just another thing he does without thinking that drives Tom insane. To be completely fair, however, that is most of Greg’s existence. That’s how they even got to this point.
“Christ, Greg,” is all Tom manages once he’s pulled up his slacks.
“Yeah? Was that good?”
“ Was that good ?” Tom mocks Greg, affectionately of course. “Yes, that was fucking good. You’re always good.”
“How good?” Greg straddles Tom’s lap again, his hands gripping his shoulders.
“Oh, is this you trying to weasel your way back into your pillow prince position?”
“Like, maybe? I think I’ve earned it.”
“Yeah, you think so?” Tom reaches down and starts to unbuckle Greg’s belt. “I think so, too. You’ve been a perfect little slut for me today. My good boy.”
“Fuck, Tom,” Greg lets out a high-pitched whine. The noises he makes when it’s his turn to be played are always the best. If it weren’t for Tom’s age, he’s sure his cock would be twitching back to life just listening to Greg.
“Use your words,” Tom says in a shaky, but stern voice. This earns him a pout. He likes to work Greg up before he touches him if they’re in a time crunch. It’s easier that way because by the time Tom finally caves and touches Greg, he’s already so riled up he cums in minutes.
“Whatever you want, you can have. You just have to ask for it.”
“Touch me, please, Tommy. Want your fingers.”
Pleased at this, Tom quickly guides Greg out of his lap and on top of his desk. Once he’s there, he finishes undoing his slacks and slides them down his legs. He’s pleased at his choice of underwear for the day: a pair of tight black briefs that accentuate his figure. There really isn’t much there, at least not to Greg, but that could very well be because he’s so used to his own body. On the other hand, Tom would gladly spend hours worshiping his body.
Tom rolls his chair closer to Greg, his hands playing with the waistband of his underwear. In response, Greg’s hips jerk. He can’t help but chuckle at the sight of his lover’s desperation, but he decides against teasing him for much longer. Instead he takes pity on him and peels them off. Above him, there’s a sigh of relief.
Immediately, Greg spreads his legs and Tom is greeted by his glistening pussy. The sight leaves Tom breathless. Greg leans back, hands pressed flat against the desk and eyes closed while Tom finally puts his hands on him. He always starts off the same way: hands exploring his thighs, stroking and caressing them, moving closer, closer…
Until his fingers are finally spreading Greg’s lips to reveal his swollen clit. Tom wants to tease him about how clearly desperate he is and how he’s dripping all over his desk, but it wouldn’t be fair. It is his fault, after all. He keeps his mouth shut and shoves his fingers into Greg’s mouth, letting him suck on them until he feels as though they’re slick enough. Once that’s done, he slowly traces circles over his clit.
“Oh, fuck,” Greg lets out a shaky breath.
“That feel good, honey?” Tom asks, though he already knows the answer. He continues the slow pace until the spit dries up. He spits directly onto Greg this time and starts to rub him a little rougher.
“Tom, please, I can’t—” he’s clearly straining himself trying to be quiet. Not only is he always needy, he’s oversensitive. Just from the brief touching of his clit, he’s already squirming. Tom’s always thought about trying out overstimulation because of this. He’d probably have to bring it up tonight, maybe over dinner. For right now he just needs to finish this up so he can send Greg home and get on with his work day.
“Yes, you can. Be a good boy for me and take it quietly.”
“Just fuck me already, please.”
Tom grins up at him, “Since you asked so nicely.”
He’s barely slipped one finger in before Greg’s whimpering again. He has to reach up with his free hand and shove his tie in his mouth like he did to himself to shut him up. Greg continues to moan, though it’s muffled now, as Tom experimentally curls his finger. Once he feels comfortable doing so, a second finger is added. Now it’s clear that Greg won’t be able to control himself. He’s trembling already and somehow, he’s even more wet.
Tom starts to move his fingers in and out of Greg now, curling them and working them in the way he knows drives his lover crazy. This, of course, gives him the results he wants because he can barely contain himself. Quickly, he feels ready enough for a third finger. Tom starts off slow once the third is added, listening to the noises Greg makes as a cue, then he moves them in and out once more.
Greg is mewling above him now, rocking his hips and practically riding Tom’s fingers. “Please, please don’t stop. Tommy, fuck, that feels so good. You fuck me so good,” he whines out despite the tie still being stuffed in his mouth. “Harder—fuck, faster, please. Talk to me. Need to hear you.”
“Yeah? You want it hard, baby?” Tom decided to stand up and his fingers curl into Greg’s g-spot. This elicits a guttural noise from him.
“Fuck, yes.”
“Wanna be fucked like the whore you are? I could take this tie out of your mouth and let the whole fucking office hear you,” his fingers start up. Greg’s head is thrown back now, hips struggling to match the pace. He looks so damn pretty like this. Tom does exactly what he says and yanks the tie from Greg’s mouth. A loud moan escapes and he immediately slaps a hand over his mouth. “Shut the fuck up.”
“Oh, God , Tommy,” Greg’s close. Tom recognizes the tone of his voice and the way he clenches around his fingers. Instead of slowing down and dragging it out he speeds up. He revels in the noises he’s hearing, silently wishing they’d decided to do this after work instead of in the middle of the day so he could actually hear him without being afraid of being caught.
There’s no warning when Greg’s body jerks and he thrashes his stupidly long limbs about. There isn’t a warning when instead of just simply cumming on Tom’s fingers, he soaks Tom’s desk, hands, and subsequently his shirt. Well, fuck, this is new , is Tom’s first thought. He stares at Greg with wide eyes, shocked and amazed at this new discovery.
“Gregory John Hirsch, I had no idea you were a squirter !”
“Wh —huh ?” Greg opens his eyes, chest heaving as he pants.
“You little minx, hiding this from me!” Tom is grinning wide, like an archeologist who’s just discovered evidence Atlantis exists.
“Fuck off!” Greg’s cheeks flush and he hops off of the desk. Before he pulls his pants up, he finds Tom’s box of tissues and wipes himself down.
“Why didn’t you tell me, huh?”
“I didn’t know—obviously.”
“Ooh, testy. Are you embarrassed?”
“Dude, obviously ,” he huffs. When his eyes finally meet Tom’s again, he feels himself become even more flustered.
“It’s hot, Greg. There is absolutely no need to be embarrassed. C’mere,” Tom motions for Greg to come back over to him.
He reluctantly does so, allowing Tom to cup his face and pull his head down to kiss him on the forehead. This soothes him immediately. “I love you, Tommy.”
“I love you, too, Greg,” Tom says his name in sing-song. He’s still got that proud smile on his face. It’s almost disgusting. Greg chooses to ignore it and just presses his lips onto his. It’s slow, passionate, but doesn’t last very long because they’ve already taken up way too much time.
“Alright, you’re going home,” Tom says once they pull apart.
“I am?”
“Uh huh. Stomach bug, you probably ate something bad for breakfast.”
“Um, okay. Got it, boss man.”
“Good. Now, get out of here. I can’t have my slutty ex-assistant in here for too long. People will start talking.”
Greg rolls his eyes and they kiss one last time before he finally leaves the office.
And as soon as Tom got home from work, he worked on repeating the events of earlier.