#bottom!dean | Explore Tumblr posts and blogs

hellhoundsprey · 4 years ago

Note

For Jack's birthday - how about sweet little virgin boy (or maybe he's dark and twisted and needs to take it out on someone, I'm up for anything) decides to lose it on his birthday. And... Dean's a sex worker maybe? Unless we need something based in canon in which case I'll gladly send in something else 😉

Who says you can’t be dark and twisted AND a virgin?

Warnings: sex work, unsafe sex, stealthing

Tags: alternate universe – no powers, first time, top!jack, bottom!dean

Jack closes the door behind them.

‘Dean’ strolls right to the bed to unzip his jacket. He cracks the window and pulls the curtains closed. ‘Dean’ throws Jack a smile. Professional as it may be, it’s a good look on him.

Jack smiles back. His hands are clasped behind him, sandwiched between his ass and the door. His heart jackrabbits and the rush of his blood can’t quite decide what body part to prioritize.

So, this is it. Finally.

‘Dean’ takes off his jacket and hangs it over the back of the single chair. “So.” Dean inspects the room from where he stands, checks his watch. “Here we are. One hour.”

“One hour.”

“One hour.” Dean sets his watch. He peers up at Jack through the thicket of his girl-long lashes. His lips purse. He’s gorgeous. “A lot can happen in an hour.”

Jack is too excited to reply. It doesn’t seem necessary. Dean comes over to him and drags his cold hand over Jack’s shoulder, down Jack’s arm. Plucks his hands free from behind him and squeezes them, stands tall and beautiful and thick in front of Jack—the manifestation of all of Jack’s fantasies, really. Clearly a sign.

“Nervous? I was nervous,” admits Dean. Half a wink. “Been some time, but I remember just fine.”

Jack says, “Undress me?” and didn’t mean for his voice to rise in the end. But the corners of Dean’s eyes crinkle soft with his smile and he does as requested. Jack’s denim jacket. Jack’s sweater.

“This okay?” Dean’s fingertips pause on the buckle of Jack’s belt. Jack nods. His face is hot.

Dean is close enough that Jack can feel and taste his breath: mint and coffee and booze. The cold of his skin from standing outside for hours on end. A car pulls out of the parking lot in front of their motel room. Jack can hear the rain hitting the asphalt.

Jack’s, “Can I kiss you?” is met with Dean, nudging their mouths together. Jack’s breath stumbles. His first time kissing someone who is not his dad. Dean’s shave is just unclean enough for Jack to be aware of the rasp of stubble against his own, smooth skin.

Dean opens Jack’s jeans. Lifts Jack’s tee up his stomach and ends their kissing with a last, firm smooch before he pulls back to get rid of that shirt for good. Despite the ajar window, the room is overheated. Jack shivers for different reasons.

Hands on Dean’s chest; feeling. Squeezing. Dean chuckles knowingly.

“Touch all you want. Dealer’s choice.”

Dean kisses him again. Slides his hands around Jack’s hips and pushes into the back of Jack’s boxers, holds and pets him. Jack’s dick throbs against his leg. He tiptoes to better press against Dean’s mouth.

“Someone’s been waiting on this, huh?”

Jack nods, gulps. Dares to put his hands on Dean’s face and it’s Dean who starts walking them backwards, towards the bed. The room is small and the distance negligible. Dean hums against Jack’s mouth. Jack gets his jeans and underwear pushed down his ass, down his thighs. Dean grabs Jack’s ass again—easy, with the size of his hands.

“What do you need, sweetheart? Wanna take the edge off, first? My hand or my mouth, maybe?”

Jack heats with hearing all that. That it’s him who is asked, but also in general. He’s…yes, all of it, everything. He wants it all. Wants Dean to teach him everything, show him what he can do… “I—yes?”

Dean chuckles. He spreads Jack’s ass just enough to be able to rub down his crack, touch his asshole. Jack shudders—Dean wraps his other hand around Jack’s cock and squeezes before he strokes. So so different from how Jack does it to himself, wrong way around and not his own hand, and it’s... Oh, that’s what Dean meant by edge. Jack flushes for the embarrassing noise he can’t hold back on and Dean tuts, kisses him some more.

“You’re all right. Let me take care of you.”

Jack holds onto Dean’s shirt, Dean’s flanks. He’s so firm underneath his clothes; Jack wants all that, too, to see and touch and kiss—Dean twists his hand and Jack groans it’s so good. Dean goes from petting Jack’s asshole to roaming up his stomach, his chest, to thumbing and then plucking on his nipple. Jack chases the touch, gets a chuckle.

“Sensitive all over, aren’t we, Jack?”

Jack moans. Tugs Dean’s shirt out of his jeans. “Can you…? Please?”

Dean lets go of Jack in favor of stripping out of his top. A single thick pendant dangling from a black leather string rests on his bare chest, and Jack realizes how there are freckles here, too—milky-light skin not much different from his own. He drags his hands over the newfound plane, gets a feel for how soft and warm exactly Dean is. No six-pack. Jack isn’t into those, anyway.

“Like what you see?” Dean smiles, gets his hand back on Jack’s cock. “Hm, yeah, you do. You think about this a lot? Kissing other dudes? Looking at each other naked?”

Jack mumbles, “Yes,” and licks his lip, can’t stop staring. Dean jacks him confidently, perfectly.

“You tell me when you’re close, okay?”

“Okay.”

“Awesome. Okay.”

Dean pushes Jack backwards so he can sink to his knees between Jack and the bed. Can rub his available hand up-down Jack’s thigh. Can ask Jack:

“You ever done this?”

Jack shakes his head, beet-red. He’s seen videos, of course. So many videos.

But nothing compares to—having it done to you. To watch Dean closing his eyes and leaning in and—wrapping his lips around Jack’s cock, held steady by the base with his skilled fingers. Dean takes him halfway down in one swift push, engulfs Jack in hotwetsoft and Jack gasps, shocked with how good it is, and the drag out is just as intoxicating. Dean suckles the tip and bats his lashes, peers up at Jack and Jack moans, didn’t expect to be watched. Dean chuckles around Jack’s cock and goes back down on it. Swallows it whole. Oh, gosh.

Jack’s hands can’t help but dig into Dean’s hair and hold on. Push him in, off, both—too much and not enough at the same time, making Jack’s balls draw tight and tingle. His cock fattens further in the confines of Dean’s beautiful throat. Dean lets him move his hips, lets him pump in and out of his mouth on his own accord. Jack groans, widens his stance. Oh, this won’t take long. Not long at all.

Dean reaches around to play with Jack’s asshole some more, and that’s that. Jack holds Dean’s skull firm and presses in, locks his hips—Dean startles, tries to pull back, but Jack is strong enough to keep him right where he is. Jack watches—fascinated, blurrily—how Dean struggles, how his face scrunches up and starts to go red. Jack lets him up once he’s done shooting down his throat. Dean gulps for air and coughs wetly.

Dean wipes his messy mouth and chin with the back of his hand. “Jesus, I said…! Not cool.”

Jack doesn’t tell him sorry. He huffs and grabs his cock instead, kneads the lingering swell of it. Dean’s spit makes the drag perfect, makes Jack’s toes curl inside his sneakers. Besides a small glare, Dean doesn’t protest getting Jack’s dick stuffed back into his mouth.

“On the bed. Take off your jeans.”

Again, “Jesus,” and a glint in Dean’s eye when he adds, “Bossy,” and then that grin again, wild and beautiful and Jack smiles back, bites his lip.

Jack climbs the bed, rids himself of the remnants of his outfit and watches Dean peeling himself out of his skin-tight jeans. He’s bare underneath. He toes off his boots, his socks. Dean crawls after Jack, hovers on all fours.

“This what you had in mind? Yeah?”

Jack nods, pleased. Rubs Dean’s skin again, the baby-flush on his tits and the lightest sheen of sweat. Dean licks his puffed lips. Watches Jack’s face with lidded eyes.

“You still sure you want to…?”

Small, “Yes,” and Jack’s cock struggles to get ready again in his own grip. “Can I… Can I maybe suck you, too? To see what it’s like,” and Dean kisses him for that, licks fat into his mouth. Pushes himself up and kneels forward until he’s straddling Jack’s shoulders. Geez, his thighs. His pretty, fat cock.

Only chubbed, not fully there yet. Dean works himself rough but lets Jack take over. Lets him get a feel, get mesmerized by how thick he is, here, too. Cut, like Jack. Dean leans back to brace all his weight onto his hands. Sighs, relaxes. Lets Jack tease him full. Or, full enough.

Dean hums, “Easy,” when Jack tugs him forward, cranes his neck to get his lips on Dean’s cock. Dean cups the back of Jack’s head to support his neck and Jack laves his tongue around Dean’s glans—prods at the slit and closes his lips and pushes on, lets it poke into his mouth, pillow against his tongue. It’s—he likes this. He didn’t doubt he would. “Fuck. You have a cute mouth. You know that?”

Jack hums. Keeps exploring and circles his tongue, fucks at Dean’s frenulum. He imagines him growing fatter for it. Jack’s fist strokes the many inches his mouth can’t get to just yet.

Soft, “Fuck,” from above. Jack’s available hand gets plucked off Dean’s thigh, gets circled and pressed down below, fingers against Dean’s…! Jack’s fingers stiffen and rub eagerly. “There you go,” and a hitch to Dean’s hips when Jack sinks one finger inside—it’s all soft and slick already, well-used and ready for Jack. Jack’s cock surges for that idea—that either Dean’s had other customers before him today or that he just keeps himself available like this constantly. Jack stuffs a second digit next to the first and Dean gasps, purrs his chuckle. “Fuck. Greedy kid,” he jokes, without an ounce of an idea how right he is.

Jack wants. Jack craves.

Dad doesn’t know where Jack is right now, because of course Jack is at school, of course Jack wouldn’t skip class and fake Dad’s signature and cash out the savings account Jack’s grandparents started for him years ago. It’s Jack’s birthday. Jack is old enough to make his own decisions.

Dean’s asshole sucks at his fingers like his mouth did mere minutes ago. Clings to them soft and needy and Jack will put his cock in there, next, and it will feel so so good, better than he imagined it would be—so dirty, with another guy, but Jack always knew he’d prefer this. That when he laid eyes on Dean the first time, driving past that alley with Dad who insisted on hurrying it up, this part of town is no good news, Jack, and Jack understood that he could just purchase Dean’s time, buy him for a while, that his mind was already made up.

Jack churns his fingers in and up, pumps them steady with Dean’s cock shuddering in his mouth. Dean groans and lets him, rolls his hips just-so—careful, subtle, because this is for Jack, not for himself. Jack is paying him for this. Jack gets to call the shots.

“Can we put it in, now? Please?”

Dean snickers. “Good to go already? Wow. To be young again…!”

Jack demands, “Sit on it,” and Dean nods with gentle, practiced compliance. Dean grabs the travel pack of lube and one of the condoms he tossed onto the bed before getting rid of his jeans. He rips both open. Jack makes a face as Dean rolls the condom over his dick for him.

Dean slathers the lube on Jack’s wrapped cock and straddles him again. Holds it steady with one hand and slowly sinks down on it—it goes in without struggle, just like it did with Dean’s mouth, and Jack’s hands fly to Dean’s hips. Jack gasps and lifts his ass off the bed to get more, deeper—Dean chuckles and allows it, can let go of Jack to stem both hands into the mattress next to Jack’s head instead, balance his weight.

“Good?” Dean smirks. Jack moans. Grinds them together, up into Dean’s tight, perfect body. Dean hums, obviously enjoys himself. He’s crushing, swollen-hot inside—Jack’s cock parts the slick walls of his insides anew on each stroke, forces him back open every time. Bottomless. Jack can’t get enough of it. “I’ll start moving now, all right?” and Jack falters, confused, until—Dean moves.

Lift and drop of his ass, circles of his hips, knocking Jack’s cock around inside him. Flexing inside and milking at Jack, and Jack can’t splutter fast enough, “W-wait,” before he’s already coming, shuddering apart inside someone. Jack’s eyes roll and Dean laughs low, kisses Jack’s mouth, his face, his chin.

“Still a good fifty minutes to go, bud. No worries, you’re getting your money’s worth.”

Jack can’t protest or do much than submit to Dean’s kisses and touches. Still buried inside him with the condom now slippery from inside and Jack’s cock so sensitive every nudge and clench of Dean’s insides makes him jump. Dean coos at him. Pets his throat for him; his chest. Sucks on Jack’s earlobe, on Jack’s clavicle. Jack closes his eyes. Dean’s weight holds him down effortlessly. It’s—nice.

Jack sighs. Dean smells nice. The bed does, too. Clean. The lube. The latex. Jack’s come laced into Dean’s hot breath.

Jack wants to ask him—so many things. How long he has been doing this kind of work. If he likes it. What his most and least favorite parts are. What kind of music he likes. If that one time Jack spotted him in church was an accident and why Dean even went there in the first place (why he doesn’t go anymore). But: fifty minutes left. Jack’s paid for sex, this time.

“I want to do it from behind.”

Dean chuckles, grinds his hips. Jack grunts, squeezes him in an attempt to keep him still—uselessly so. “You’re overworking that poor dick, kid. Gotta let him breathe for a minute. Why don’t you lay back, let me spoil some other parts for a change?”

Jack reluctantly agrees. His load drips out of the condom once Dean pulls him out. Dean cleans him, discards the condom. Kisses and nuzzles Jack’s clean, floppy dick before he moves lower to mouth at Jack’s balls. Jack groans—they’re not any less sensitive than the rest of his junk. His knees draw up and out on their own, though. He keeps his dick in his hand just to protect it from Dean’s eager mouth.

Dean gets comfy on his stomach and goes to town on Jack’s balls. It’s nice, yes, but Jack would rather…! But he has to get hard again first, somehow, so he’s all out of ideas. Dean’s laps and kisses travel lower and lower until he’s making out with Jack’s asshole, and that is… Oh, that is good. Really good.

“You like that?”

Jack nods, groans. Squeezes his dick; wills it hard, hurry it up.

Dean hums. Laps at Jack’s hole again. “I can put something in here if you want. My fingers…my cock…!”

“No, just…” Jack huffs. Tugs harder on his dick. “Just—keep going. Get me hard again.”

Dean scoffs. Spreads Jack’s hole with his thumbs. “Sure thing.”

Doesn’t take much longer until Jack is hard enough to consider it ‘enough’. He nudges at Dean’s head. Dean complies, moves. On all fours, his ass towards Jack and the headboard, he’s—geez, he’s stunning. Waxed bare and freckled here, too. He shakes his ass and grins over his shoulder, dips his chest lower into the bed.

“C’mon,” he teases. Jack watches Dean’s hand grabbing his own cock, stroking it sweet and firm. “Like that? That’s what you wanted, right?”

“Yes.” Jack sits up. Kneels up behind Dean.

Dean gasps as Jack thumbs his cock into him without preamble. “Jesus, wait—!” No condom. Just the slick inside Dean.

“No,” says Jack, and bottoms out. “I’ll pay extra,” he adds, and Dean’s fury falters a little for that but he’s still not convinced. Not that he necessarily has to be. Jack pulls him back by his hips and churns his dick deep, makes Dean’s tense breath thud out of him—his pretty face is flushed from the position, from the humiliation of a high schooler telling him what to do. How to do his job.

“It’s…” Dean groans for the next thrust. His eyes slide smaller. His asshole wrings tight around the base of Jack’s bare cock. Dean licks his lip. He’s still stroking himself. “It’s not gonna be cheap.”

“That’s okay.”

Jack makes him stay ass-up after he’s done loading him up. Makes him push Jack’s come back out so Jack can finger it back in, watch Dean’s asshole bloom and shudder and take whatever it’s given, how it swallows it all like a greedy mouth. Dean groans. He hasn’t come a single time and his dick is going soft yet again, irrelevant between his legs. Jack drags his tongue over the gape of Dean’s hole and tastes—lube, and ass, his own come. Moves deeper, to Dean’s audible delight, to suck at Dean’s balls. The underside of Dean’s cock. It swells under the attention. Jack nurses on Dean’s frenulum, that tight little bundle of skin right underneath the head—Dean groans, wriggles back against Jack’s face for that.

“You sure you don’t want me to fuck you, kid?” Sounds desperate. Jokingly, but desperate.

“Not this time,” admits Jack, his hand now milking Dean’s cock upside-down.

“Oh? There will be a next time?” Dean’s chuckle rumbles low. His asshole keeps mouthing at nothing and Jack stuffs his thumb inside just to give it something to work with. Dean groans like it feels good. “Jesus, kid. Killin’ me.”

Jack smiles. Keeps working him.

Eventually, soft: “You’re gonna make me blow if you keep that up…”

“That’s the plan.”

“Jesus… Jesus, are all kids your age this filthy? Did I miss something?”

“Shut up and let me get you off,” and that works.

Dean shifts cute in the sheets. His cock leaks wet in Jack’s fist and is all swollen and heavy with blood, every vein popped and tangible. Jack rubs his thumb over every single one of them, teases around the flared edge of the head, makes Dean growl into the sheets. Two fingers up his ass, massaging Jack’s load in deep. Jack licks his lip. His dick flinches but he’s too sore. No way he can get it up again. It doesn’t matter too much.

“Come,” orders Jack. “I want to see you do it. Come on my hands, Dean.”

With a tremble and a groan, Dean does.

He draws up inside, crushes Jack’s fingers—Jack adds a third despite the pressure to bang it soft again while Dean’s cock throbs hard in his grip, shoots thick into the bed.

“Fuck, fuck…!”

“You’re not done,” warns Jack. Keeps moving his hands. “All of it. Give it to me.”

Dean eventually grabs Jack’s wrist, trembling and panting and telling Jack no, for real, you’re killing me, and Jack scowls but does let up on him. Again, “Jesus,” and Jack’s stomach knots mean and he’s this close to reprimanding Dean for cursing so much. He’s too dizzy and sated and frustrated all at the same time, though. Too distracted by the lazy flop of Dean’s body, the way he squirms into the sheets like a sack of flour and just stays that way. He can’t be that old. Younger than Dad, for sure. “Gimme a minute… Phew.”

A minute turns into five. Into ten.

“We can shower together,” offers Dean. Jack declines. Jack goes by himself.

Dean consoles him. Talks about yeah, see how I told you you’re gonna burn yourself out? “I mean, I can’t blame you.” Dean smirks, winks; still naked, hugging Jack close. “I’m quite the motivation, huh?”

While Dean showers, Jack peels out the money from his backpack. He counts it and fans it out on the nightstand. Dean’s eyes dart towards it first thing once he’s back in the room.

Jack put his clothes back on and smiles up at Dean from where he sits on the edge of the (haphazardly re-made) bed. “Extra, like you said.”

“Hm.” Dean comes over, only a towel around his hips. He picks up the money to count, smacks his lips. He holds his hand out towards Jack without looking at him. “Another hundred.”

Jack gives him another hundred. Dean rolls up the money and stuffs it into his jeans’ pocket.

“So,” he says as he proceeds to wriggle into his jeans, “you mentioned a next time?”

#jacksbirthdayparty #hellhoundsprey #request #spn fanfiction #first time #top!jack #bottom!dean #sw!dean #dean/jack

31 notes · View notes