Chapter Text
Tubbo laughs when Tommy first brings it up.
"Really? That's the serious news you wanted to talk about, big man?" Tubbo says.
"Toby," Tommy whines, drawing out the name, "It is serious! It's not like I can do what any other kid in college does and find a girlfriend or hook up at a party. I'm not even fuckin' out yet, and I'm not really interested in my first shag getting thrown onto the internet."
Tubbo sobers at that, "Ah... yeah, that is kind of a problem."
"You think?" Tommy snaps back, slumping in his chair and staring at Tubbo's discord icon miserably.
"Well, do you really have to? I mean, loads of people don't have sex till their older," Tubbo offers, "I'm sure you'll have like, boyfriends and shit in the future."
"But that's the point, Toby!" Tommy flails his arms out even though Tubbo can't see his dramatic gesturing, "I don't want to get into a relationship and embarrass myself by fumbling through sex because I became a celebrity when I was 16 and never had the chance to shag anyone!"
"Tommy, it's not going to be like that--"
"Yes it fuckin is, and I've been panicking about it for weeks now. I just want to get it over with, okay!" Tommy interrupts.
"Well if that's how it is then just hire a hooker or something, I don't know. It's not like you don't have the money."
"Tubbo."
"What?" Tubbo says defensively, "It's a perfectly fine idea."
"Toby, I'm not hiring a fucking hooker to take my virginity," Tommy deadpans, and Tubbo laughs.
The conversation devolves after that, and Tommy's problem never actually gets solved. It isn't until after Tubbo's left the call that Tommy thinks back to his friend's comment.
...what if he did hire someone?
Would it really be so bad? Sure it's kind of weird, but Tommy bets they shag way more weird people and creepy old men and shit so a nice 17 year old kid would probably be relaxing, right? Are male hookers even a thing?
Tommy tries to convince himself he's just curious as he opens an incognito tab. It's good information to have! He flicks through sites and reviews and recommendations trying to make sense of the poorly organized thoughts and directions.
It isn't easy, but by the end of it Tommy feels like this might actually be possible.
He sits back in his chair, hand pressed over his mouth as he stares at the website on the screen. Holy fuck, he's actually considering this.
In the end, it's simple enough, really. He finds Wilbur's profile disturbingly fast. He's an attractive bloke with curly hair, and Tommy feels his stomach flip in anticipation.
He can't do this--he's an influencer, not to mention a minor. Yeah, he's only a few months off of being 18 and it's not technically illegal, but Tommy figures if he has to use the phrase not technically illegal to convince himself to do something it's probably not the best idea.
…It's his money and his decision though, and he mulls it over for all of twenty minutes before he decides to contact Wilbur.
There's an email listed under Wilbur's charming portrait. He’s just reaching out, it doesn’t mean Tommy’s actually going to schedule anything.
His fingers fly over the keys as he types out a generic message asking about rates and (embarrassingly) mentions how it's his first time. He conveniently leaves out his age and occupation, hoping he can avoid it when the time comes. (Ha, comes, he laughs to himself. Maybe he isn't old enough to be hiring an escort after all.)
He clicks send before he can think about it any further, and it's a done deal.
He stretches back in his chair and turns his attention towards more pressing things. He might not know how to suck dick, but he can fall into the rhythm of making a funny video any day.
He opens the Premiere Pro file and stares at it, with its array of color-coded clips and lack of being fucking finished.
The vlog stares back at him, with its 'last edited three days ago.' He drags a couple clips back and forth, applying audio cross-fades at the cuts. He previews his work area, noting where he needs to readjust the cut for timing, and then watches it again. And again.
His hand itches to scroll mindlessly through Reddit.
He watches it again. And again. And again.
By the time he goes to sleep that night, he's completely forgotten about any conversation regarding hookers and escorts.
----
That is, until Wilbur answers his email the next morning.
The man is polite and professional, reassuring Tommy that it being his first time, "won't be an issue in the slightest," and he's really... surprised? That Wilbur's so normal?
He doesn't know why, but now that he's thinking about it, he realizes he was expecting Wilbur to be something like the adverts, typing with every word capitalized and constantly advertising, like Enlarge Your Guinea Pig (Hot!) or Local Russian Honey in Your Area Looking For Love! But Wilbur is--well, he just seems real.
Wilbur proposes some dates, and a couple align with Tommy's schedule. Then the weight of it actually hits him.
He's asking a hooker to take his virginity. And the hooker seems nice!
Tommy picks a date. Wilbur sends an address and some rules regarding payment and other things. It's to be paid in cash, half up front the rest at the end, and both of them have the right to stop the evening at any time.
He's given instructions for how to prepare for the evening. (Tommy wonders if Wilbur always does that or if it's just because it's his first time). Wilbur also lists some limits, and Tommy stares at them blankly because people actually do that and think its SEXY what the fuck?
He hastily agrees to Wilbur's terms, and then it's done.
There are officially 8 days left until Tommyinnit loses his virginity. He can't decide if the swirling in his stomach is excitement or nausea.
----
The next 8 days are both the slowest and the fastest of Tommy's life.
For a while it feels like it will never end, and then suddenly he's standing in front of an ATM pulling £450 of cash while he waits for his Uber to arrive. Wilbur wasn't the most expensive that Tommy saw, but he sure as hell wasn't cheap. It makes part of Tommy cringe to be spending this much just for a couple hours of time, but he figures losing his virginity isn't something he wants to be frugal on.
The Uber drops him off at the hotel 15 minutes later, and he feels like every eye is watching him walk through the doors of the middle class hotel and into the elevator.
Room 318, the email had said. Just knock.
The elevator rises to the third floor and Tommy wipes his sweaty hands on his trousers. He's not normally a nervous person, but this is enough to make him want to hit the lobby button and never come back. Maybe he can pretend he's sick and back out or block Wilbur or a million other things to avoid knocking on door 318.
He doesn't, though. He walks down the hallway with all the confidence he can muster and he stands in front of the door. He raises his hand to the door and hesitates before knocking twice.
The door swings open not a moment later and Wilbur looks... well, normal . He's got on a plain t-shirt and jeans just like Tommy and it weirdly relaxes him. It's not like he expected Wilbur to be naked or something at the door, but seeing Wilbur look like a normal guy helps.
"Tommy, right?" Wilbur asks as he gives him a onceover. Tommy thinks he might be prettier in person.
"Um, yeah," Tommy's already stuttering, but Wilbur gives him a genuine smile. Tommy doesn't think he's the first blushing virgin Wilbur's seen at his door.
"You can come in, you know," Wilbur gestures past him to the neatly made bed, and Tommy nearly trips over himself trying to get into the room.
Tommy fumbles for the bills in his pocket and thrusts them at Wilbur, "The money like you asked."
Wilbur looks at him appraisingly and tells him to put it on the nightstand.
When Tommy looks back, Wilbur looks like he might go to take off his shirt, and Tommy asks "Can we actually just um, talk first?" and Wilbur looks up at him in surprise that melts back into his schooled casual expression.
"Sure, Tommy," Wilbur replies smoothly. Tommy cringes at himself for asking, but he knows he won't be able to start right away. He's too overwhelmed.
He tries sorting through all the different threads of conversations he could go with, weighing their outcomes and how likeable he'd come off, and why the hell is he so worried about making a good first impression when this is the last time he'd ever see Wilbur--
But when he opens his mouth to speak, what's blurted out is, "Do you play Minecraft?"
Wilbur blinks owlishly at him.
Bye. Tommy's gone. He, ah, will elegantly rise from the bed. He will stride back out into the hallway, where he will proceed to bang his head on the wall until he rights himself. Then, he will buy a plane ticket to Antarctica and live out a new life as a penguin herder.
For Christ's sake, he's seventeen , not seven .
But then, Wilbur flashes a brilliant, genuine grin at him and says, "Yeah, actually! I don't quite like telling people because it's, y'know, got that reputation of being a children's game, but I like it," He shrugs, "Play with my friends, and all that."
What?
"And, you, Tommy? What d'you like about it?"
Tommy hesitantly swallows, mouth unreasonably dry, and then launches into his own opinions on the game, soon getting into the rhythm of it while ranting about the latest update split.
Conversation flows easily from there, like he just undammed a rushing whitewater river, and they hop from topic to topic: oh, the café across the street from that Tesco's is pretty good, oh, Wilbur plays in a band sometimes? Oh, did you know one time--
Tommy bursts out laughing at a dry joke Wilbur slips loose, fringe bouncing with his wheezes, and soon Wilbur joins in with his own, high-pitched and giggly. He's enjoying himself. Really, really enjoying himself.
He almost forgets why he's in this room 318 in the first place.
That is until he finishes laughing, looking up at Wilbur and freezing when he realizes how close he is. Wilbur has a soft, knowing smile on his face.
"Thank you for the conversation, Tommy, but--" He tilts his head towards the cheap digital clock on the nightstand, "--if we want to get to the main event I'll have to cut it short."
Tommy flush, "Oh. Yeah, yeah the uh... thing." He finishes lamely, and Wilbur chuckles.
"Yes, the thing. After all, you aren't paying me for my engaging personality," Wilbur teases, but Tommy feels an uncomfortable chill rush over him at the reminder.
Right. Paying him.
"How do I, um, what do you want me to do?" Tommy asks, feeling quite suddenly tossed from the shallow end into the deep without ever being taught to swim.
"That's normally my line," Wilbur says but moves on before Tommy can respond, "Did you read what I sent you?"
Tommy's blush deepens and he nods. The resources Wilbur had given him were... detailed to say the least. Wilbur looks pleased, and Tommy swallows down the satisfaction that he'd made the man happy.
"I think I want to be on the uh, the bottom," Tommy says hesitantly and Wilbur nods encouragingly.
"Okay," Wilbur steps back just enough to pull his shirt over his head, and maybe Tommy stares a little but certainly not enough to prompt the small smirk Wilbur's wearing when he looks back up.
Tommy scowls, "Shut up."
"What? It's very flattering--"
"Wilbur," Tommy whines, and he laughs. Tommy feels some of the tension melt away.
This is still Wilbur, the guy he was laughing and chatting with a few minutes ago.
Tommy takes a deep breath. He can do this. He reaches back and pulls off his shirt as well--albeit not as smoothly as Wilbur did, but at least his hands aren't shaking anymore. Wilbur runs a hand across Tommy's arm and collarbones making him shiver.
"Pretty," Wilbur says simply, and Tommy stares at him with wide eyes, hands hovering aimlessly.
Wilbur takes pity on his inexperience and guides the hands to his shoulders, and Tommy slowly winds them around the older man's neck. In turn Wilbur places a hand on Tommy's jaw, tilting it up a tad.
"Tommy?" Jesus Christ no one's ever spoken to Tommy in that tone of voice before.
"Y-yeah?"
"Can I kiss you?"
"Yes," Tommy says, breathless, and Wilbur dips down and presses their lips together and oh . So that's what his mates were always going on about.
Tommy knows this is different than anything he's ever tried to do with a girl. He's fumbled around with them before, sure, but nothing compares to the way Wilbur's pushed into his space. Wilbur's hand has climbed its way into the curls at the base of Tommy's neck and Tommy breaks the kiss to whine when Wilbur tugs at them.
Tommy is immediately embarrassed at the breathy sound he just let out, red painting his cheeks. Wilbur smirks again while he brushes a thumb over Tommy's reddened cheek.
"Aw, did you like that?" Wilbur teases and Tommy's response is stuck in his throat so he simply nods. Wilbur's eyes flash appreciatively and Tommy feels warmth flood his stomach. Wilbur's gaze is trained on him, and Tommy thinks he can do this. He needs to do this.
Wilbur sits back on his heels and looks over Tommy again. He motions for Tommy to lie back on the pillows and Tommy complies instantly.
"We're going to go further now, okay?" Wilbur tells him, breath ghosting over Tommy's bare chest. Tommy feels weirdly cared for throughout this whole thing. Not once has Wilbur pushed him into anything he doesn't want to do.
"Okay," Tommy agrees and lets Wilbur pull his jeans off of him. Now he's lying in just his boxers on this starched bedspread in front of the prettiest man he's ever been this close to.
It's only when he's nearly naked that he clocks how hard he really is. There's a wet spot forming in his pants and Tommy logically knows this is nothing compared to what Wilbur's seen, but Tommy can't help but want to impress him. He doesn't want to be the virgin he knows he is.
Wilbur trails a finger along Tommy's hip, noting how Tommy unintentionally bucks up into the sensation. He finishes by palming Tommy's cock and Tommy whines again, louder and clearer than before.
"Someone's excited," Wilbur's voice hasn't lost its teasing lilt, and Tommy thinks he likes it. He likes the curl of heat the degradation gives him, and he’s sure Wilbur's picked up on it.
He's utterly fucked already, and Wilbur's not even gotten his cock out yet.
But, Wilbur seems content to leave it as it is. Tommy is nothing but grateful because, for some reason, the idea of Wilbur pulling his dick out makes him lightheaded and dizzy.
“Can you touch it?” He’s surprised with how level his voice is, and mentally fist-pumps. Tommy one, nervousness zero. He’s practically already won.
“‘Course,” Wilbur slides his boxers down until Tommy can kick them off to the side. “Tell me if you want me to stop, okay, Tommy?”
Tommy nods wordlessly, swallowing thickly as his nerves return with a fiery passion. It’s almost like this is the point of no return, where someone else lays their hands on his dick for the first time.
He’s prepared for Wilbur to hop straight to it, but then he starts littering light kisses and shallow nips with fleeting touches from his fingertips on his thighs, and Tommy jumps with each one, breathy gasps sounding without his permission.
“Feel good?” Wilbur asks between kisses, and Tommy gives a shaky answering hum.
“Really good,” He thinks he hears Wilbur murmur out a soft ‘cute’ and he’s about to protest, but then Wilbur bites somewhere in the soft junction between his thigh and arse, and Tommy jolts with a drawn-out moan, every other thought chucked out the door. “More, please?”
“As you wish.”
The line’s so cheesy, but it goes straight to his chest, melty and gooey. Wilbur moves, presumably to actually get his hand on Tommy’s dick, but then Tommy stops him with a foot.
“Actually, before you do that, can I…” he trails off, nervous again. Wilbur just tilts his head, non judgemental, and it pushes him to finish his question, “Can I have a kiss?”
Wilbur blinks, but then smiles, “Of course.”
He leans up to press his lips to Tommy’s, soft and chaste, and Tommy basks in the feeling before pulling away.
“Thanks.”
Wilbur flashes that small smile at him again and trails his hand down, circling Tommy’s cock with too-light touches. The anticipation makes him lightheaded again, and he leans back in for another kiss to ground himself, wrapping his arms around Wilbur’s neck.
It’s as he’s losing himself in the kiss that Wilbur finally brushes his dick. Wilbur’s hand feels like his own, but also doesn’t, with his feather-soft and fleeting touches. Wilbur rubs under his head and Tommy sighs into his mouth, hips twitching into Wilbur’s touch.
Wilbur smiles into their kiss, and his hand retreats. Tommy whines, but it soon returns with fingers slicked with cool lube, alternating between quick and satisfying pumps, and long and drawn out strokes that had Tommy crumbling in seconds.
It sends pleasure coiling in his gut faster than any other time Tommy’s tried getting himself off, and Tommy moans into Wilbur’s mouth, slackjawed and eyes squeezed shut.
Tommy’s body curls in on itself, thighs tensing and untensing as he feels release approach closer and closer, but then Wilbur’s clever fingers are leaving him again, and Tommy whines louder and more petulantly, tugging on his shoulder.
“C’mon, c’mon , I was so close ,” He ignores Wilbur’s chuckles, “Why’d you stop?”
“It’s your first time,” Wilbur smoothes Tommy’s hair back, but it’s a bit of a useless effort because his fringe flops back into place right after, “Don’t want to overstimulate you. Unless…?”
Tommy flushes at the idea of Wilbur bringing Tommy to orgasm again and again, past the point of Tommy going mindless with pain-pleasure… but he’s right.
“Maybe next time.”
Next time. He knows it’s echoing in Wilbur’s head too, with the way the man is staring at him, but instead of calling him out on the presumption Wilbur only hums.
He takes Tommy’s hands and puts them on his hips, with his thumbs at the waistband of Wilbur’s plain boxer briefs, “Would you like to do the honors?”
“Y-yeah, I can,” Tommy says, crackly and nervous. Fuck. He really is a blushing virgin, isn’t he? It’s nerve-wracking, though. Wilbur’s cock is right there, straining against the fabric stained with his pre-cum.
Tommy swallows, then tugs down his underwear.
It’s strange, seeing a dick that isn’t his up close like this. Wilbur’s hangs forward, a bit to the left, unlike Tommy’s, which curves back, head almost hitting his belly button. It’s flushed, and a little darker than his own.
That’s going up his ass. The thought makes him nervous again, and he knows he needs to stall a bit before that.
“Can I, um, I’ve never--I’ve never given a blowjob before.”
“Would you like to?” Wilbur asks with a bit of amusement, and Tommy flushes before nodding.
“Alright, then where do you want me?”
“Here is fine, I think,” Tommy fidgets, “Lie back?”
Wilbur complies while Tommy himself scooches down so that his face is level with his dick.
He looks up at Wilbur, who gives him a reassuring smile, “Take it easy, just be careful of your--”
“Teeth, I’ve heard. Don’t worry, can’t catch it on any braces--got ‘em off a while ago,“ Tommy bares his teeth to show him, and Wilbur laughs. It’s pleasant, and Tommy thinks his moans would sound just as nice.
“Comforting. And one more thing-- “
Tommy stops, mouth hung open over Wilbur’s dick. It hangs a bit awkwardly, so he closes it with a click, “Hm?”
“Relax. Don’t worry too much about it, okay?” He tucks a stray hair back into place, rubbing gently at his ears.
Tommy nods, “Got it.”
He stares at it for a moment, his tongue darting out to wet his lip, and he’s painfully aware of Wilbur’s eyes on him. God, Tommy wishes he had done more research or at least watched some porn or something, or maybe he shouldn’t have said anything to Wilbur at all… but Tommy’s always wanted to know, always wanted to learn.
Well, no time like the present.
When he wraps his lips around the top of Wilbur’s dick he expects it to be at least a little unpleasant--a bad taste, an uncomfortable stretch of his jaw--but instead he’s met with just… skin. It’s strange, but there is something inherently erotic about the way Wilbur’s hand slides through his hair. All in all it just… doesn’t seem so scary anymore.
Tommy tries bobbing a bit, but the lack of moisture makes the action a bit difficult. He pulls his head off and frowns slightly, for a second his eyes flick up to meet Wilbur’s.
“Try letting spit pool in your mouth a bit,” Wilbur suggests, “Be a little sloppy before you really try to do anything.”
“...okay,” Tommy says, and when he returns to his task he finds that Wilbur’s advice holds true.
A flush of embarrassment turns the back of his neck red as he fumbles through wetting Wilbur’s cock enough to even try sucking it, but just like before Tommy finds he likes the heat. Likes it enough to gain a bit of confidence.
Confidence he really shouldn’t have had only a few minutes into his first blowjob ever because as soon as Tommy tries to take most of Wilbur into his mouth he overcalculates and the dick knocks the back of his throat making Tommy reel back, eyes stinging and coughing to the side.
The hand in his hair moves to his back, and Wilbur rubs circles onto his skin until his coughs die down, assuring Tommy of… well, Tommy can’t really focus on his voice when he’s trying not to die so he doesn’t know what he’s saying but the tone is calming nonetheless.
When it seems his body’s involuntary responses have stopped tormenting him, he hiccups--
And burps.
Immediately, he wants to grab the duvet and hide under it. Mortified heat floods his cheeks, and he considers just slapping the rest of the money on the nightstand as a consolation fee and scurrying off into the night. They’ll make stories about him. He’ll be the next urban legend. The pasty midnight man, bum cheeks blindingly whiter than snow.
Wilbur’s just barely holding back a laugh, Tommy knows he fucking is, because his shoulders are shaking, and he’s ready to burn into ash right then and there.
"That was fucking--"
Gross. Cringe. I just remembered I have a doctor's appointment to go to, never mind the fact that it’s past midnight. Never contact me again, by the way. If you Google my name, maybe you’d see an obituary that says “Here Lies Tom Simons, Too Fucking Stupid, Can’t Suck Dick For Shit”.
“--adorable! It's sweet that I get to experience your firsts,” Wilbur brushes a stray hair behind Tommy's ear, thumbing at his still embarrassed-warm cheek.
Tommy makes a face, “What am I, your toddler? These my first steps? You just saw me crash and eat shit? Took a photo for the family album?”
Wilbur lets out a laugh, hearty and full-body, “I guess you could put it like that.”
He presses a kiss to Tommy’s forehead, brushing aside his fringe. Against the skin, he mumbles, "It's refreshing, being with someone so... genuine and vulnerable. Really makes me remember that sex is a form of intimacy .”
Then, Wilbur pulls away. Tommy sorta misses his soft lips against his temple. He wants to be held up in Wilbur’s arms, just to bask in his warmth on every square inch of his skin.
“I don’t remember the last time I laughed like this,” He gives him a small smile, “Thank you, Tommy.”
Something flutters in his stomach, all nervous and shit. He huffs, just for the sake of it, and mumbles with his chin almost tucked into his chest, “Yeah, okay, no problem.”
Tommy would have been content to avoid Wilbur’s eyes forever after that, but Wilbur lifts his chin and slots their lips together, lazily kissing Tommy until the tension and embarrassment unwinds.
"Would you like to try again?" Wilbur says softly, threading his fingers back through Tommy's hair.
"Can you talk me through it?" Tommy asks hesitantly.
"It would be my pleasure," Wilbur smiles, and Tommy pulls back, licking his lips. He moves until he's hovering over Wilbur's cock, looking up nervously. Wilbur's eyes darken at the sight, and he begins to instruct him with a low, soothing tone.
"Don't just go right to the main event, Tommy. Take your time. Use your tongue, lips, hand... it's not just about your mouth. Think about what feels good to you. Explore, experiment, watch my reactions."
Tommy tries to leverage some of his normal reckless confidence and drags his tongue up the side of Wilbur's cock. When Wilbur's hand tightens in his hair he does it again, mouthing around the tip a little. He hadn't noticed last time, but it's so... hot. Tommy could feel the weight and temperature of the cock on his tongue. He could trace the veins and ridges, mouthing over its terrain with the curiosity that had driven so much of his life.
"That's it, Tommy," Wilbur praises, a little breathless, "Now give me a little more, just a bit at a time."
He slips the head of Wilbur's cock into his mouth, careful to keep his teeth away, and gives an experimental suck. Wilbur's breath catches and he lets out a pleased hum. Tommy feels pride start to build. He's actually making Wilbur feel good, and he wants to do even better. Slowly he starts to bob his head, taking a bit more each time. It's not a lot, but Tommy wraps his hand around the untouched portion, using his spit to slick the way as he adjusts to the new sensation.
When he finally adjusts enough to do more than just bob, Tommy flattens his tongue against Wilbur's cock and drags it up as he rises, swirling it experimentally around the top, and Wilbur moans. Actually moans. It's soft enough that Tommy almost misses it, but when he hears the melodic sound it sends a flash of pride through him. Before he can get lost in his success, Wilbur pulls him off, and Tommy frowns.
"Did I fuck it up? I thought I was doing alright actually--"
"You were, fuck you were perfect, Tommy," Wilbur looks a little disheveled now and Tommy finds the flush on his cheeks addicting. He leans down to capture Tommy's lips in a kiss, almost sloppy compared to his earlier control. When he pulls back Tommy feels like he's burning.
"But I'd like to fuck you now."
Tommy's breath gets caught in his throat and he laughs, "O-okay, yeah. Fuck."
"Lay back for me, sweetheart."
Tommy scrambles to obey while Wilbur reaches over to the bedside table and grabs a bottle of lube. He fidgets and watches with wide eyes as Wilbur slicks up a few of his fingers.
"Have you ever fingered yourself before, Tommy?" Wilbur asks, and fucking hell how does he manage to say that so casually.
"Um, once. After I read the, uh, instructions. I didn't really know how to do it though," He admits, "Didn't get very far."
"Luckily, I do know how to do it," Wilbur says with a grin before continuing in a more serious tone, "It's going to feel a bit weird at first, maybe even uncomfortable, but it shouldn't be painful. I want you to feel good, Tommy, and I need you to tell me if that isn't happening."
Tommy nods, but he's tense and nervous. Wilbur sighs and presses a kiss to his lips, "Last bit of advice, relax. Let me take care of you, Tommy."
"You fuckin' relax, dickhead," Tommy spits out, all nerves. Wilbur snorts at his comeback and grabs a pillow.
"Here, put this under your hips, it'll help with the angle," Wilbur instructs as Tommy lifts himself off the bed once more.
He settles into the pillow and feels oddly exposed despite literally sucking off the man in front of him not two minutes before.
"Tommy, stop thinking," Wilbur reminds him as Tommy tries fruitlessly to feel less awkward.
"Can't--what if I make a weird noise or cum too fast or cry?" Tommy rattles off all his concerns while Wilbur idly warms up the lube with his hand.
"One, I've heard all sorts of noises and I promise you won't be the first one to sound weird. Two, it's your first time -- I'd be surprised if you didn't cum too fast. And three, crying during sex isn't always a bad thing," Wilbur smirks at the last part and something fizzles in Tommy's gut.
"You done overthinking?" Wilbur continues as he lowers his hand to Tommy's hole. The sudden wetness makes Tommy flinch, but he lets Wilbur massage the muscle until one finger slips in.
Tommy gasps, but it's more in surprise than anything. He had tried it himself, but Wilbur's one finger already pushes against his walls better than three of his had managed.
Wilbur must be able to tell he's uncomfortable, because he starts to rub soothing circles into Tommy's hip. Tommy tries to melt under the touch, but he knows he's still too tense.
"Hey, Tommy, good thing there are no mobs nearby so we can do this, huh?" Wilbur jokes and Tommy lets out a sharp laugh that dissolves all the tension in his body.
While Tommy laughs, Wilbur slips a second finger in beside the first and Tommy finds it's not nearly as uncomfortable as it was before.
"I can't believe you made a Minecraft joke while you're fingering me."
"Worked, didn't it?"
Wilbur starts to scissor his fingers gently and the stretch is weird, but it doesn't hurt. Wilbur definitely subscribes to the concept of never too much lube as he pulls his fingers out to drizzle more on them.
Tommy suddenly feels empty and he says before he thinks about it, "Kinda feels like I've just had a shit."
As soon as he realizes what he's said, he slaps a hand over his mouth. He knew his lack of filter would catch up to him eventually, but he didn't think it would happen at such an inopportune time.
Wilbur pauses his movements while Tommy covers his face in mortification.
"You are really something else, Tommy," Wilbur shakes his head, but he seems no less interested in fucking Tommy. Tommy supposes it's what he's paid him to do, but he likes to think Wilbur might actually want to fuck him.
"Ready for more?" Wilbur's voice has dropped an octave, and Tommy's suddenly back into the heat of the moment.
"Y-yeah, okay," Tommy agrees. Wilbur resumes stretching him open all while murmuring to him what a good boy he is. Tommy thinks he might actually have passed away from embarrassment, and he's actually in heaven now.
Wilbur increases the number of fingers to three, and that's when he finally stretches enough to reach Tommy's prostate. Tommy knew he had been searching for something, and he sort of knows what the prostate is. It didn't prepare him for how good it felt.
Tommy squeaks more than moans, and Wilbur looks at him so fondly Tommy can barely stand it.
"Feel good, darling?" Wilbur asks as he presses further down, sending sparks of pleasure down Tommy's spine.
"Wilbur, please, more," Tommy's already been reduced to begging, knowing he's never felt this good before.
"Patience, love," Wilbur reassures as he finally pulls back from Tommy after bringing him to the edge for the second time that night.
"After all, we're just getting started."
“So, we can get a move on then, right?” Tommy knows he’s being whiny and bratty, but he can’t really find it in himself to care. He wants more now, appearances be damned. “Please, Wilby?”
The nickname had slipped out as less than an afterthought, but Wilbur goes wide-eyed. He collects himself in a blink, but it’s too late--the idea has been planted in Tommy’s head. He's played cutesy and innocent to slither out of punishment before, and he knows how to utilize it to its maximum potential.
He ducks his chin, glancing up at Wilbur through his lashes he knows are lush (some schoolmates have bemoaned their jealousy of said fullness), and says, "Pretty please?"
Embarrassing to do it fully nude, sure, but it's worth it when Wilbur takes a shuddering breath and crawls, no-- stalks towards him, even if he's on his hands and knees.
Every inch that Wilbur claims is one Tommy's rabbit pulse self wants to climb back, but he's locked in place by Wilbur's gaze. If he even breathes too loud, the tension will snap.
Wilbur ends up pushing him flat with just one palm against his chest, brushing his knuckles against Tommy's cheek. "Do you know," he murmurs, "how fucking pretty you are?"
Tommy swallows, something thick in his throat preventing words from bubbling out.
"Do you know," Wilbur continues, pushing the pad of his thumb into Tommy's mouth, "how hot that was?"
Tommy whimpers, tongue coiling around the digit. His eyes fall shut, taking in the feeling of Wilbur playing with his mouth and the rumble of his voice.
"I don't think you do," Wilbur pops his thumb out, and Tommy whines at the loss but quiets down when Wilbur smoothes his spit-slicked thumb across his bottom lip, "That's alright. I'll show you."
The head of Wilbur's lubed cock presses against him, and suddenly, his nerves are rearing up one more time. He tries opening his mouth to say something, but it won't work.
Oh shit, oh shit, oh shit. He's completely frozen and he hates it. Fucking lame.
"Hey, Tommy, you okay?" Wilbur brushes his fringe aside to press their foreheads together. Tommy licks his lips, and tries forcing out that it'd be fine. He just needs to fucking get over himself, but his voice refuses to sound.
Wilbur pulls away, and sits back on his heels. His dick is pointing straight out of his crotch like some sort of meaty laser beam, and the absurdity of it has him snorting despite his fear.
"There he is," Wilbur smiles, smoothing back Tommy's hair, the movement comforting and relaxing. He scratches at the back of his head just above the nape, and Tommy melts , "You good?"
Tommy nods. "Yeah, I just--needed a moment, you know how it is."
"Yeah, all too well," Wilbur runs his nails through Tommy’s hair one more time, "Ready?"
"Born ready," Tommy says. "But, uh, actually--"
"Hmm?"
"Can we…" Tommy holds out his hand expectantly.
"Like this?" Wilbur intertwines their fingers, and Tommy bobs his head.
"Yeah, like that."
Wilbur leans back down to press a chaste kiss to his lips, and puts himself back into position. "Good?"
This time, Tommy squeezes Wilbur's hand, and the warmth of his palm grounds him, letting him nod his consent.
Wilbur pushes in, and it's really not that different from his fingers at all--but also, it's really, really different. It almost feels like he's pushing into his lungs, which anatomically, makes no fucking sense, but Tommy's breath is leaving him either way.
Wilbur pauses to let him adjust to the stretch, and Tommy tightens around him, because that's what he does when there's something lodged up his ass.
"How's it feel?"
"Weird," Tommy says and opens his mouth to elaborate only to find he’s not really sure what to say, “Uh… yeah. Just. Weird.”
Wilbur laughs, and Tommy feels it through their point of connection. Is it good that he's making Wilbur laugh so much during sex? Whatever. He squeezes Wilbur's hand again.
"You can keep on going."
Wilbur squeezes back, then starts moving deeper until his pelvis is flush against Tommy's. Huh, that actually wasn't so bad. But it wasn't so good either. He really doesn't get what all the rage is about, but then Wilbur presses a soft kiss to his jaw, and that makes something in his stomach feel funny and all fluttery and shit. Before he can analyze it too much, Wilbur says, "I'm gonna start going now, okay?"
"Comprendo," Tommy says, pulling out seventh year Spanish class on Wilbur's ass and just barely resisting the urge to flash a thumbs up at him, and oh God, that's lame.
But the man just laughs again before setting a pace, pulling in and out in a steady rhythm.
Wilbur starts off slow, kindly letting Tommy get used to the feeling of something much bigger than fingers sliding in and out of him.
At first it's the only thing Tommy can really feel besides the nervous iron grip he has on Wilbur's hand, but soon more sensory information filters in. Wilbur's lips on his neck, his breath warm but loud, the firm grip Wilbur has on one of his thighs, bending the leg up enough to ease the way of his thrusting, the rustle and creek of the bed as they rock together.
It's a lot ... But it's also not enough. Tommy shifts under Wilbur, a slight squirm as he chases a little more contact, a little more friction. He swears he feels Wilbur smile against his skin.
"How do you feel, Tommy?"
It's an innocent question, but Wilbur manages to make it sound filthy as his voice rumbles next to Tommy's ear. Tommy flushes and tries to think amidst the stimulus.
"Right as fucking rain, big man," He manages, "Good, great, pog one could even-- fuck you," Tommy cuts off with a gasped moan as Wilbur lifts his leg a little higher, adjusts his angle, and hits the same bundle of nerves that had made Tommy melt a few minutes earlier.
"That's what we're doing," Wilbur responds smoothly, grinning as Tommy scowls.
"You're a bitch."
"Sorry, couldn't resist. You're so fucking talkative, Tommy..." He pauses, something genuine shining through, "Made me wonder if I could fuck you into a rambling mess."
"Oh," Tommy says, breath ripped right out of his lungs by the needy look in Wilbur's eyes. Wilbur kisses him again, and Tommy thinks he might never breathe the same.
"Can I try?" Wilbur says, looking into Tommy's eyes with a kind of need that makes him shiver.
"Fuck yes," Tommy blurts out with enthusiasm that shatters the soft sensuality of the moment. Wilbur doesn't seem to mind.
His only response is a smug expression, and Tommy would have told him he looked fucking stupid if he hadn't lost all ability to form insults a second later.
He had liked the fucking before. It was deep and slow and he felt like if Wilbur kept at it he was going to fall apart piece by piece, but his is an entirely different much better animal.
Tommy's hand spasms around Wilbur's as the man starts properly fucking him.
His free hand darts up to grab the iron bars on the bed frame, noises he would rather die than let anyone other than Wilbur hear tumbling from his lips.
"Wilbur, Wilby--" Tommy begs, and the man groans.
"I know, fuck, I know, baby. You're doing so good, such a perfect little slut for me--" Tommy whines, and Wilbur grins, "You like that don't you, Toms. Being my whore."
He does. He really does, but fuck if the self-satisfied tone in Wilbur's voice doesn't piss him off.
"Pretty sure you're the whore here, prick" Tommy pants, but he doesn't get a chance to hear Wilbur's reply because the bastard has a hand wrapped around his dick.
"Holy fuck , Wilbur. Please, please."
Between Wilbur's cock and the slow strokes Wilbur has started on Tommy's dick he knows he's not going to last another second if Wilbur doesn't stop. A mess of warnings fall out of Tommy's lips, but Wilbur doesn't stop at all, quite the opposite in fact. The slow strokes turn to fast pumps, matching pace with Wilbur's fucking.
"It's okay, Tommy. You can do it," Wilbur coaxes, "Be a good boy and cum for me."
And just like that Tommy tumbles head first into the best fucking orgasm he's ever had in his life. He can hardly think through the crash of pleasure, and he tightens around Wilbur, rocking into his last couple of thrusts on pure, desperate instinct.
"Fuck, Toms--" Wilbur moans, and Tommy feels him get dragged over the edge with him, spilling inside Tommy with a frankly bizarre, gut deep warmth.
When Tommy comes to his senses, Wilbur is breathing heavy above him, expression a bit shocked. Tommy's grin falters a bit.
"You good?" He asks as soon as he can breathe again, damning how shaky his voice sounds.
"Yeah, yeah, fuck, I just didn't," Wilbur stammers, "I'm sorry. I didn't mean to--I didn't ask if I could cum inside you, but when you..." He trails off and stares at Tommy like he's a puzzle Wilbur hadn't been aware he was solving.
Tommy jumps to reassure him, "No, no, it was good, really fucking good, Wilbur," His hand slips from the bed frame and thumps on the pillow as he swallows, "Very good."
His awkward praise seems to draw Wilbur back into himself. The insecurity Tommy had glimpsed disappears, and he smiles. He leans down to press a soft kiss to Tommy's lips before slipping out--God that's a fucking weird feeling--and falling to the side of Tommy. His head tips to the side to look at Tommy as he speaks.
"I'm glad."
----
Wilbur doesn't know what he's going to do with this kid. He watches as Tommy relaxes, heavy breaths turning to slow deep ones instead.
Tommy looks up at him, a contemplative expression on his face.
"I sort of liked that you finished in me," He says.
"Really?"
Wilbur scrunches up his nose at the thought -- he always thought it felt sort of gross, and it's a pain in the ass (no pun intended) to clean up afterwards.
"Makes this seem a little more real," Tommy replies sleepily, basking in the afterglow that Wilbur knows is stripping the filter from Tommy's thoughts (though Wilbur doubts Tommy ever had a filter to begin with).
"Oh," Wilbur whispers more to himself as he slips out of bed. He keeps wipes in his bag for quick clean-up and he wants to make sure Tommy doesn't have the experience of drying cum plastered on his back. Wilbur knows the feeling all too well.
"Where are you going?" Tommy's voice pitches higher with a note of worry and Wilbur curses himself for not remembering he's going to be more vulnerable now. This is a first time client, not one of his regulars.
"Just getting something to clean up with," Wilbur reassures and Tommy visibly relaxes at Wilbur's response.
"Can we... can we shower together instead?" Tommy sounds small and Wilbur doesn't normally do this extensive of aftercare unless prearranged (and prepaid).
He glances back at Tommy's naked frame wrapped in sheets Wilbur could never personally afford and he melts. Why does he think this might be the first of many exceptions he makes for Tommy?
"Yeah, I'll start the water," Wilbur grins more genuinely than he expects. Tommy mirrors his grin and Wilbur knows he's bound to cross a line or two or twelve by the end of the night.
----
The shower is nice .
With anyone else, Wilbur would be concerned they'd just use it as an excuse to weasel their way into a freebie, but Tommy doesn't touch - at least, not like he wants something from Wilbur. He just stands under the stream of water as Wilbur scrubs down his back.
Wilbur offers to wash Tommy's hair which startles him as soon as the offer leaves his lips, but Tommy blushes so prettily through the steam.
Tommy's hair is soft and Wilbur sort of wants to pull it again. He just takes the time to pull his fingers gently through the knots instead. His lewder desires wash down the drain with the remnants of soap.
"Do you... do you want me to wash yours?' Tommy asks timidly, fiddling with the shampoo bottle in his hands.
Wilbur isn't sure how this boy keeps surprising him, but he's so gentle and kind unlike anyone who has paid for Wilbur before. Wilbur doesn't trust himself to speak, so he just nods. Tommy beams again and Wilbur wants to drown in the sunshine radiating from that smile.
The process goes much the same with a whispered apology when Tommy tugs a bit too hard.
"Hey, you keep doing that and you'll owe me another fifty," Wilbur teases and Tommy huffs as he pushes Wilbur under the water.
They towel off in relative silence, but Tommy dresses in the same trousers from before and a clean shirt he had apparently squirreled away. He's so basic teenage boy it hurts, but for some reason it only makes Wilbur adore him more. Wilbur slips lazily into a new pair of sweatpants, eyes on Tommy.
Tommy pulls the remainder of the crumpled bills from his pocket and pushes them into Wilbur's hands. Tommy shifts back and forth anxiously as Wilbur counts them, not that he thinks Tommy would short him.
He's right. Tommy doesn't short him, quite the opposite in fact.
"Tommy? This is too much," Wilbur flattens the bills in his palms, and Tommy shrugs.
"It's a tip, innit? You deserve it for treating me so nice," Tommy doesn't let Wilbur hand back the extra.
"I can't-" Wilbur starts as Tommy closes Wilbur's hands around the bills.
'You can and you will. Consider it a deposit for next time if you want," Tommy grins again in his self-assured way that WIlbur's seen glimmers of the whole night.
"Next time?" Wilbur echoes. Tommy nods.
"You don't fuck a man's brains out and then not expect him to come back. I'll call you?" Tommy shuffles into his trainers and is out the door with a kiss pressed to Wilbur's lips before he has room to complain.
Since when did Tommy get the upper hand here? And why does Wilbur like it so much?