Work Text:
“Is that supposed to be a compliment?”
“No.” Jon folds his arms, tapping his fingers up and down the sleeve of his tweed jacket. “Just. Trying for honesty.”
“Step one of trying to pick up a hot guy,” Tim leans forward over his desk and holds up a finger demonstratively. “Never be honest.”
“Really, Tim.” Jon looks away, a faint color rising in his cheeks. “I’m trying to be serious here.”
And to Jon’s credit, Tim believes he is. But how can you not laugh at this whole situation? Your uptight asshole of a boss (actual tightness of actual asshole yet to be confirmed) comes up to you and propositions you for a literal one night stand. He even uses the word proposition like a Victorian lady in a historical romance novel.
I’ve recently found myself interested in intercourse, conceptually, he’d said.
But I wouldn’t feel comfortable picking up some random hanger-on at a late-night establishment, and I’m unlikely to engage in any kind of genuine romantic entanglement what with my work and general demeanor, he’d said.
You and I, however, do have a comfortable relationship, and your reputation for one-off occasions precedes you, he’d said.
After such heartfelt flattery, how could Tim say no?
Tim is honestly surprised Jon doesn’t break down and back out on the way to Tim’s apartment. He wouldn’t have been insulted or anything, he was mostly expecting it, and the flush that had started crawling up Jon’s neck when they first discussed it is now a permanent fixture of his face. He’s dug his fingers so tight into his thighs he’s gonna leave creases in his dress pants. Tim leans back and lets an arm fall carelessly over the back of Jon’s seat, just to see the visceral tensing of the muscles in Jon’s jaw. Really, this guy. How horny must he have been to actively approach Tim with this proposition? Well, it’s always the ones you least expect.
Tim doesn’t even have a chance to take off his shoes before Jon brushes past him into the apartment and opens his briefcase, rifling through his papers. He pulls out a box of condoms, a bottle of lube, another box of condoms of a separate brand, and so on and so on, stacking each neatly in a line on Tim’s end table. It’s practically a comedy bit the quantity of stuff that’s coming out of Jon’s bag. Tim barely holds in his laughter.
“Jon. Jon. Were you carrying around a whole sex store in your briefcase?”
Jon turns around, scowling. “It’s my first time, Tim, I wanted to be prepared.”
“Well fun fact, we only have two dicks between us so we’re not going to need four boxes of condoms.”
Jon’s scowl deepens and his nose scrunches in. It’s the same expression he makes when Elias reprimands him for his people skills, but in this particular situation it’s surprisingly adorable.
“And speaking of our two dicks, what were you hoping to do with yours?”
“Tim.” Jon smacks him on the arm. If he had pearls he’d probably be clutching them he looks so affronted.
“You’re the one who asked for this, Jon,” Tim reminds him, helpfully. He strides forward and grabs one of the boxes of condoms off the table to inspect, hopefully giving Jon a touch of privacy to gather himself. Uncomfortable with discussing it is one thing, but if Jon can’t express what he wants, Tim can’t give it to him.
Jon is quiet for a while, and Tim makes a big show of not looking up from his thorough investigation of each of the four boxes of condoms, trying to pick his favorite. He hears Jon take in a shaky breath through his nose and breathe it out. “...I was hoping to be penetrated.”
“Fuuuck me.” Tim grabs the edge of the table and curls in on himself like he’s been punched in the gut. “How do you make that textbook talk so arousing?”
“Is that alright with you? Being…” Jon furrows his brow, his mouth moving oddly around the unfamiliar term, “on top?”
Tim snorts, but regains his composure. “You’re the boss.”
Jon’s face blanches and he looks mildly horrified. “Please don’t.”
“Seriously though. This is your first time. I want to make sure you’re comfortable and enjoying yourself. I know what I enjoy, and it’s about 95% of things, so I’m sure whatever we do will be great. And if you trot out some kind of kink so crazy that even I’m not into it, well, I reserve the right to back out.”
“Fine, yes, that’s...fine. Fair.” Jon nods a few times, still looking faintly pink-tinged and lightheaded about the entire proceeding.
Tim grabs a box of condoms and a bottle of lube and pats Jon on the shoulder. “Bedroom?”
Jon nods mechanically, stiffly making his way into Tim’s bedroom. Tim wishes for a second that he’d had a bit of advanced notice, his bedroom isn’t necessarily a mess but it could be neater. His bed isn’t made, and a few pieces of laundry are scattered about or piled up on his chair haphazardly. Jon hardly seems to notice, though, in his single-minded panic. Tim can basically see the thoughts going through Jon’s head as he works his way through every possible scenario before sitting awkwardly on the edge of the bed.
“You know you can relax a little bit. You’re not going to have a good time if you’re this stressed out about it.”
“Mmm,” Jon forces out, nodding, but he seems even tenser than before.
“Would you like some alcohol?” Jon shakes his head. “A massage?”
“I think I would rather get this over with, please.”
“Yeah, I’m not going to do anything if you’re treating it like that.” Tim crosses his arms and leans against his doorframe. Jon looks up at him surprised, his eyes conflicted and confused. “This isn’t something I’m doing to you so you can have had sex. This is something we’re doing together because we both want to.”
Jon lets out a deep sigh and runs a hand through his hair. “You’re right. Of course. I do, I do want this, it’s just ...difficult for me to talk about. I’m not used to it. And I don’t like thinking about it.”
“I get it.” Tim plops down on the bed too, wrapping his arms around one of his legs and resting his chin on his knee. “I can take the lead, but you’re going to have to participate in the conversation. I need to know what you’re comfortable with and enjoying, yeah?”
“Right.” Jon nods again, but he seems more confident this time. “Right.”
“And hey, it’s just me.” Tim spreads his arms wide and grins his most disarmingly goofy smile. “No one’s ever been scared of me.”
Jon gives him a tight smile, and Tim feels the tension start bleeding out of the room. He scooches in closer and tucks a strand of hair behind Jon’s ear, letting it give him an excuse to leave his hand cupped against Jon’s cheek. He meets his eyes and god, Jon’s eyes are dark and wide and beautiful like this. He looks like he might shiver himself entirely apart with barely constrained anticipation.
“Mind if I kiss you?” Tim asks.
“Um. Not on the lips. Please.”
“Fair game.” Tim leans in, pulling Jon’s face up to meet him, and presses a soft kiss to Jon’s jaw. His skin is softer than it looks, and Tim takes a bit of time with it, letting each kiss linger deliberate and slow. He noses up under Jon’s ear and sucks at the sensitive flesh just beneath it. Next to him, Jon is already shaking from the stimulation, letting out soft gasps every time Tim presses in. It’s awfully flattering. Tim slowly makes his way down the side of Jon’s neck, enjoying the way he tilts his head to give him access, and lifts his hands to unbutton Jon’s shirt. He barely starts into it before Jon pulls away, suddenly.
“Wait, wait.” Jon sits back, his face flushed pleasantly, red all the way to the hairline, and the curve of his jaw shiny with spit. “Don’t, not, um.”
Tim takes Jon’s hand and puts it in his lap, rubbing his thumb against it in reassuring circles. “You want to stop?”
“No. I just…” Tim waits patiently as Jon fumbles his way through his mind for the proper explanation. “The human form is not...exceptionally pleasant to me. I don’t enjoy bodies. Nude bodies. I don’t like to think much of my own and I don’t...I don’t think I want to see yours either.”
Tim purses his lips. “Okay. That’s fine. That’s...yeah. Okay. Are you sure? I’ve been told as far as nude bodies go, mine’s rather aesthetically pleasing.”
“I don’t like looking. I don’t want to see, because the more I see the more I think about what’s happening, and the more I panic, and the more I have to think of myself as something sexual, and I just do not want to. I don’t want to know.”
“But you still want to have sex,” Tim says again, just to doublecheck.
“If it’s still possible. If you still want to.” Jon runs a hand through his hair again, tangling his fingers in his dark curls.
“Of course, I still want to, Jon,” Tim shakes his head, “you do not even realize how incredibly sexy you are right now. It’s my goddamn privilege to get to take your virginity however you want me to.”
And Tim has to admit, he said that mostly to see just how red Jonathan Sims could possibly get. The answer is very. Incredibly. Tim almost wishes he didn’t mind being undressed so he could see how far down his chest it spreads. But his dark pupils are blown so wide and wild at the prospect of it that Tim is beyond turned on. By his fully-clothed boss. Fuck, he’s a lost cause.
“Wait, hold on.” Tim stands up and the bed resettles after the loss of his weight. Jon follows him with his eyes, still wide and waiting. “You’re in your work clothes, Jon. You’re going to wreck them.”
Jon looks down at himself as if only just realizing the reality of his pressed trousers and button down.
“Let me grab you something comfier. Bathroom’s down the hall, you can change there.” Tim doesn’t wait for Jon’s polite refusal, he starts rummaging through his pajama drawer and pulling out an old pair of gray sweats and a big t-shirt. Which will probably be gigantic on Jon but oh well, looks are not the goal here. He hands them to Jon and shoos him off to change so that Tim can get into something he doesn’t mind getting stained as well. In his head he’s running through the logistics of how this will work, trying to plan out the smoothest possible path so that he can continue appearing suave and confident. He has a reputation to protect, after all.
Tim pauses, suddenly thinking of something. “Hey, Jon?”
There’s a moment of silence and then Jon calls back from the bathroom, “yes?”
“Pro/con on me seeing your…” Tim searches for the word Jon would be comfortable with, “genitals?”
A longer moment of silence. “I would prefer you didn’t?”
“Cool. Can you bring a washcloth back when you’re finished?”
Tim was right, his clothes absolutely swallow Jon. The sleeves of the t-shirt hang almost to his elbows and the bottom hangs almost to his knees. He looks even smaller than usual, like a wet cat. It’s strangely compelling. He hands over a pale yellow washcloth.
“What’s this for?”
“It’s your first time having sex.” Tim hands the washcloth back and Jon accepts it, confused. “There’s no way in hell I’m letting this end without you finishing. Stick it down your pants. I’ve got some experience with blowing your load in your trousers and trust me, it sucks. This will be easier to clean.”
“This is ridiculous,” Jon protests, the tips of his ears burning red.
“Effective, though. We’re gonna have to MacGyver this a little if we’re going at it non-traditionally.”
Jon tucks his head. “It’s a pain, isn’t it.”
Tim reaches out and grabs Jon’s hand, bringing it up to his mouth so he can press a warm, lingering kiss to the center of Jon’s palm. “You’re worth the trouble.”
Jon smiles back, warmly, and lets himself get drawn slowly back to the bed. Tim sits down and pulls Jon with him so that he tumbles into straddling his lap.
“You’re only saying that because you like a challenge.”
“Maybe,” Tim says with a wink. “But a good time is the Tim Stoker guarantee.”
Tim winds a hand in the excess fabric of Jon’s t-shirt and pulls him close, kissing at the other side of his throat. Jon unravels much faster this time, planting his hands against Tim’s chest and breathing out approvingly. Tim’s other hand starts smoothing up and down Jon’s thigh, putting just a little more pressure than he normally would for light foreplay to make sure Jon can feel it through the sweatpants. It certainly seems like he can, from the way his fingers start digging into Tim’s chest.
Tim bites lightly at the side of Jon’s throat and feels his whole body twitch at once. Very interesting. Tim smiles into Jon’s skin and brings both his hands down to grip Jon’s thighs just at the crease of his hips before biting down a little harder.
“Ah! T-Tim!” Jon shivers deliciously, squeezing his eyes shut. Tim can feel Jon’s thighs tensing and jumping beneath his hands. He slides them just a bit farther until they’re clutching Jon’s ass, which he gives a generous squeeze. Jon lets his head fall to Tim’s shoulder with a groan. Against his belly, Tim can feel Jon starting to get hard.
“I haven’t even done anything yet,” he teases, lightly.
“Shut up.” Jon’s voice has the harsh quality of someone just on the edge of out of breath. “Keep going.”
“This is all incredibly flattering.” Tim takes Jon by the shoulder to push him away from his own chest, and leans in to run his nose down the front of Jon’s shirt, looking for the hard nub of his nipple. It’s not hard to find through the thin t-shirt. He slides his tongue over it, not minding the rough pull of the fabric (though the taste could be better), and Jon yelps again, almost twisting away.
“Ha!” Tim pulls back and sticks his tongue out at Jon. “Sensitive nipples. I win the betting pool with Sasha.”
“You do not have a bet going about this.” Jon looks horrified, but the red in his cheeks isn’t all from embarrassment.
“Nah, but I should really start one. I have the inside track now and she’d never believe you seduced your way into my bedroom.”
“Can we please take this seriously?”
“I am!” Tim says, and without warning, presses his fingers into the bulge in Jon’s sweatpants. Jon curses and doubles over, dropping his forehead to Tim’s shoulder again. He reaches around and clutches the back of Tim’s shirt like it’s his only lifeline.
It’s not the easiest thing to navigate, properly stroking Jon’s cock through both the sweatpants and the bulky mess of the washcloth, but from Jon’s twitches and cries he can’t be doing too bad a job of it. He’d never pictured Jon being so vocal in bed, but he supposes his voice has always been one of his better qualities. Tim catalogues the changes in it: his deep groan of pleasure when Tim wraps his hand around the shaft and squeezes tight, his whimpering moan as Tim pulls his fingernails up the entire length to force the sensation through the fabric. Between the noises and the way Jon is starting to rut needily against his stomach, Tim is enjoying himself plenty.
He slides a hand back to Jon’s ass, squeezing again, and then slipping his hand under Jon’s waistband. He pauses a moment, both his hand venturing under the clothes and the one still stroking Jon’s cock, waiting to see if he’s crossed any boundaries. But Jon just whines and presses himself back against Tim’s hand and now even Tim is a little flushed and flustered at it all.
“Have you ever put anything inside yourself?” Tim whispers in Jon’s ear as he slides a few fingers over Jon’s hole. Jon’s whole body shudders, either from the words or the touch, and he shakes his head against Tim’s shoulder.
“I’ve, ah, I’ve masturbated, but that all seemed awfully…acrobatic for me. A bit too much effort.” Jon presses his face into the side of Tim’s neck and Tim can feel his blush from the heat of his skin.
“Okay,” Tim says, trying to sound calm and in control. “We’ll take it slow, don’t worry.”
He pulls his hand out of Jon’s pants and reaches for the bottle of lube he brought in earlier. It’s still done up in plastic and Jon sits back, resting a bit with his hands on Tim’s thighs, as Tim struggles to get it open.
“I suppose I didn’t quite think through my preparations,” he says, apologetically.
“Nah, this is pretty par for the course.” Tim snaps the plastic finally and pops the cap, pouring a generous portion onto his fingers. “Sex is way slower and more awkward than most people think.”
“I guess I assumed everyone knew what they were doing except me.”
“No one ever knows what they’re doing, Jon.” Tim pats his chest. “Come here.”
Jon leans forward and curls up on Tim’s chest, tucking his head under his chin. Tim reaches around with his clean hand and pulls down Jon’s sweatpants just enough to expose his ass.
“I’m not looking, don’t worry,” he chides gently. He’s been around enough asses to have pretty decent aim. And if it gets a bit messy, well, no one minds that in the bedroom.
“I know,” Jon says, and his breath hitches a bit as Tim slowly circles his rim with a finger. “I trust you.”
Tim pushes a finger inside easier than he expected. Considering the way he was before, Jon has relaxed into this whole sex thing pretty amazingly. Tim sets up a slow pace, taking a moment to circle his finger and pull a bit at the rim on each pump.
“You’re doing really well,” he says softly and Jon squeezes his hands where they’re gripping Tim’s shirt.
“Can we not talk about it, please?”
“Sure. Here,” Tim lifts the hand that’s not inside Jon up and tangles his fingers in his hair. He pulls his head back gently and starts kissing Jon’s neck again, a bit more heated this time. When he stops to suck hard against the skin, Jon rumbles low in his throat. Tim uses the distraction to slip another finger inside, working them in together and splitting them apart to widen the stretch.
It continues like this for a few minutes before Tim feels confident that he could not possibly hurt Jon. He separates his mouth from Jon’s skin so he can look him in the eyes. Jon is panting and disheveled, a little red with his eyes half-lidded. Tim’s never seen him in a state like this before, so hazy and relaxed. His cock pulses with the thought of taking him apart even further.
“You ready?”
“In terms of generalized anxiety? Not really.” Jon grimaces. “In terms of informed consent? Yes.”
“It’s gonna be fine. Just keep looking at me, because I’m going to have to remove a tiny bit of clothing for this next part.”
Jon nods, and Tim can see some of the old tension sneaking back into his jaw. Tim doesn’t break eye contact as he sneaks a hand down and unzips his fly, finally giving some release to his poor dick that’s been half-crushed for the past few minutes. He slides on a condom and gives it a few strokes with a lube-covered hand for good measure, but honestly he’s never felt more ready in his life. He lifts Jon off his lap a bit to line things up and then catches the flash of panic that goes through Jon’s eyes.
“You okay, Jon?”
Jon works his answer over in his mouth. “I’m thinking about it now.”
“In a bad way?”
“In an I’d rather not be thinking about it way.”
“Okay. Hey, Jon.” Tim catches Jon’s eye and starts waggling his eyebrows suggestively.
“What are you doing?”
“I’m distracting you with my suave charms. Is it working?” Tim throws in a little head wiggle along with the eyebrows for good measure. Jon snorts out a laugh.
“Tim, you are absolutely ridiculoooooh.”
As soon as Jon laughed, Tim brought him down until the tip of his cock pushed into him. Jon gasps, and Tim stops pushing, letting gravity slowly inch him farther and farther down.
“Okay?”
“Better,” Jon says, although his voice is breathy and high. “Thank you.”
“No prob, boss.” It’s a testament to how overcome Jon is that he doesn’t even object to the nickname. He breathes quickly as Tim slowly slides deeper with lazy rolls of his hips. Pretty soon Tim’s cock is entirely sheathed, Jon practically sitting in his lap again.
“T-that’s all of it,” Tim says, his composure starting to actually crack. “Fuck, you feel good, Jon.”
Jon’s breath is coming in shivering bursts. “That’s…that’s a lot. This is a lot.”
“So the ladies tell me.”
Jon smacks Tim in the shoulder. “Don’t be crass.”
“I think the ship sailed on being crass when I buried myself in your ass, Jon.”
Jon turns very pale and then very red and his eyes start to creep down to where they’re joined together in a panicky sort of way. He stops himself and grabs Tim’s shirt, pulling the fabric up and hiding his face in it.
“Jon?” Tim taps at the top of Jon’s head but he refuses to look up. “Talk to me, what’s happening here.”
“You’re looking at me. And we’re having sex.”
“Yeah, I like looking at you.” Tim runs a hand soothingly through Jon’s hair. “And I’m pretty keen on having sex with you too.”
Jon digs his face deeper into Tim’s shirt. “I’m a mess.”
“Good thing I’m quite skilled with messes. Like that mess of a filing system Gertrude left us.”
“Tim!” Jon finally pulls his head out to stare at Tim horrified. “Do not talk about Gertrude while you’re inside me.”
Tim’s dick throbs at the sound of Jon saying inside me. He rolls his hips again and Jon frowns at him, in that put-upon way that he has.
“I think I’ve got a decent solution. Here, hold on.” Tim plants Jon’s hands on his shoulders and then cups his own under Jon’s ass so he can rise somewhat gracefully to his feet. The movement jostles him inside Jon and he hits a spot that makes Jon’s spine go very straight and his eyelids flutter, so he marks that down for later.
“Tim what the hell are you doing?”
“You weigh like nothing, Jon, Jesus, do you even eat?”
“Of course I eat!” Jon wraps his legs tight around Tim’s hips to support himself as Tim makes his way over to his dresser. He winds one arm under Jon to keep him up (does he have hollow bones or something?) and uses the other to rifle through his drawers until he grabs another oversized t-shirt. He makes his way back to the bed and sits with a potentially unnecessary bounce that has Jon shivering against him.
Tim takes the t-shirt by the sleeves and spins it around and around until it’s a tightly twisted rope of fabric, and then he presses it into Jon’s eyes and knots it around the back of his head.
“Voila,” he says, with a flourish that Jon cannot appreciate because he cannot see, “instant blindfold. No gross bodies, no seeing yourself. Just feelings and my charming voice.”
“Yes,” Jon’s voice is adorably contemplative. He lifts a hand and gently touches the bottom of the fabric wound around his eyes. “This is...this is better, actually. Thank you, Tim.”
“Stoker guarantee,” Tim reminds him with a smile.
Tim rolls his hips again, experimentally, and this time Jon lets out a long, slow moan, his body relaxing against Tim’s. He takes this as a good sign and grabs him by the hips, fucking up into him in earnest. He presses his face into Jon’s chest, rubbing his nose over the fabric until he slides against Jon’s nipple again.
“Ah, T-Tim, please,” Jon whines, and it doesn’t even matter what he’s begging for, because just the sound of Jon begging sends shivers down Tim’s spine, and he thrusts up into him desperately, chasing the pleasure of Jon squeezing around him. He brings a hand down to paw at Jon’s bulge again, embarrassingly unable to bring any of his usual finesse to it because the way Jon feels is driving him completely out of his head.
It’s a shame Jon can’t see his own climax, it’s a showy and impressive spectacle. His whole body tensing and shuddering, the slight drip of drool down his chin, the way his hands squeeze into Tim’s chest and his body tightens around Tim’s cock. The feeling of it around him sends Tim over the edge too, burying his face in Jon’s chest as he does.
They stay like that for a moment, panting against each other, before Tim slips out of Jon and pulls his sweatpants back up. Jon slides bonelessly off his lap, collapsing onto the pillows. He pushes the blindfold up off his face, blinking owlishly at Tim.
“You know, we could have just turned off the lights,” he says, sounding far too much like his usual composed and cranky self for how undone he was just a moment ago.
“Yeah, well, light switch was slightly farther than the drawer,” Tim answers, flopping down to lie next to Jon. “Besides. I liked watching you. You, Jonathan Sims, are incredibly sexy. And I have a lot of experience to pull from.”
Jon rolls his eyes, but it’s not as sarcastic as it usually would be. He reaches down into the front of his sweatpants and pulls out the soiled washrag. Tim gestures for him to just toss it on the ground and he does so. They can deal with it tomorrow.
“That worked surprisingly well, actually,” Jon grumbles as he crawls his way onto Tim’s chest, curling up in his arms.
“Hey, that’s why you come to me for these things,” Tim says, leaning down and pressing a kiss to the top of Jon’s head. “The Tim Stoker guarantee.”