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fic - jack finally convincing sam to pop his cherry after learning about sex and begging him forever, featuring major size kink, esp around sams muscles and dick, belly bulge, sam's hand over jacks mouth or stuffing something into his mouth to keep him quiet so dean doesnt end up hearing them, sam getting pretty rough cause jack feels so good and it's so wrong it just makes it even hotter
Combining this one with:
#1 @lilith-the-ancient: Sam gently teaching overeager Jack how to masturbate, which turns into him teaching Jack how to have sex (though please no bottom Sam).
#2 @lilith-the-ancient: Jack's birthday present is Sam's dick, which he takes very, very enthusiastically.
Warnings: rough sex, unsafe sex, age difference, sam sometimes drifts into trauma-related thoughts
Tags: first time, top!sam, bottom!jack, sam is not a good dad, sam monsterfucker winchester doing what he does best
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Sam glares but proceeds to pull his shirt over his head.
āI hope youāre happy with yourself.ā
Jack, who is blissfully unaware of the existence of sarcasm, nods enthusiastically as he steps closer and puts his hands where his eyes are glued to: Samās chest, the wide expanse of it and then down his ribs, his abs. He canāt take his eyes off all that newly-bare skin. Jack is already flushed just from this.
This might be a bad idea.
āCāmon.ā Sam plucks Jackās shirt out of his jeans. āGet a move on.ā
Heās locked the door. Dean is busy with his new issue of Busty Asian Beauties and maybe thatās part of why Jack brought this up again, seeing it laid out on the table before Dean was reprimanded to please take it to your room, seriouslyāwhat heād like to do with Sam, heās thought about it and he thinks heād enjoy it, a lot, and donāt they always say he needs to unwind, get less robotic? Sam begins to sweat, to heat up. His stomach is tense. Jackās soft touches arenāt helping.
Sam wants to hurry so itās over sooner.
Thereās saying no to someone and thereās saying no to Satanās spawn.
Okay, no, wrong train of thought; sex. Think about sex.
āCan we kiss?ā Jack peers up at him, lets Sam strip himāmilky-white underneath, barely any hair and Samās very sure he shouldnāt think about that too hard, either. Sam swallows, nods. Tosses Jackās shirt away and cups that pinked face in both hands, tips it up and leans down and kisses Jack on the mouth. Feels him inhaling, tensing. Hands on Samās own. A thumb to one of the popping veins on the back of Samās hand. Jack decides, āI like that,ā once he can. Sam kisses him again. Jack sighs happy.
Sam undoes Jackās belt for him. Pulls it out of those jeans and throws it away while Jack keeps looking at Samās face, licks his own lip. Dreamy eyes, already glazing over. Jesus. Heās young, isnāt he?
āYou ever touch yourself? Here?ā Jackās lips part for the cup of Samās hand flat over his crotch. He shakes his head. Of course.
āIsā¦is that bad?ā
āUh, no. No, just⦠Nothing. Thatās okay.ā
More kisses for distraction. Sam brings his tongue into the mix. Jack stumbles around it but eventually gets the hang of it. Like a calf looking for milk. Sam removes his own belt, unzips.
Sam gets a hold of Jackās wrist to shove that limp hand into his jeans. Jack gaspsāsqueezes, rubs.
āItās gonna get bigger,ā Sam explains. Rubs at Jackās dick through his underwear with emphasis. āLike yours. See?ā
āWow.ā
āFeels good?ā
āUh-huh.ā Jack licks his lips again. He tentatively begins to push up into Samās touches. His eyes swim back and forth between Samās. āMore. Sam, can we doā¦more?ā
Sam doesnāt verbalize but he does press a last kiss to Jackās mouth before he drops to his knees and tugs Jackās underwear just low enough.
Jackās dick is smooth and pretty like the rest of him. Sam switches to autopilot and catches the already-leaky tip with his lips, doesnāt think and just pushes on. He can take Jack all the way, no problem.
Jack gasps so loud Samās hair shocks to stand on end.
Hands in Samās hair; clasping, holding. He gets a grip on Jackās hips to push him back, pull off. So he can bob his head, let Jack feel it. Jack sure feels it, all right.
Softest, āOh,ā when Sam pulls back to present Jack how hard he himself is. Shiny with Samās spit, throbbing and heated, and Sam makes a show of laving his tongue all around the sensitive head. Makes Jack moan a first time and purses his lips, eyes up to Jack; hollowed cheeks and shallow strokes, just engulfing the tip. He pulls off for good, licks his lip. Grabs between his own legs, holds Jack in place with one hand only, easy.
āWanna try that on me? Get me nice and hard, Jack?ā
Jack nods with his mouth pinched and his cheeks all lit up and Sam directs them over to Jackās bed, sits at the foot of it and pulls Jack with him. Jackās adorable in that clumsy kind of way. Eager, and thatāsāthatās something, at least. Flattering. Sam hasnāt had the chance for many hookups lately. Not the time nor the mood. Thatās part of this, too. Unwinding. Just for ten minutes.
āEasier if you get on your kneesāyeah. There you go.ā Sam pulls himself out of his underwear and Jackās eyes go a little wider in the dim light of the room. Sam sinks back, braces himself on his elbow, jerks himself with the other. āCareful with the teeth. Just see what⦠Jesus, yeah, something like thatā¦!ā
Jack does his best to be careful. Mostly tongue but thatās good, enough to tease. Sam keeps stroking the half-soft length of his cock, lets his knuckles bump against Jackās soft-soft lips up top. God, he wants that. Does a Nephil even need to breathe?
āDoing good.ā Jack hums in reply. Points his tongue and prods at Samās slit, and Sam groans for that, lets his head tilt back. āFuck. Try sucking on it? Like I did with yours?ā
Jack hums again and shuffles closer to the bed. Both hands on Samās thighs instead of touching himself, his jeans and briefs still hanging off his hips. Sam pushes his own clothes lower, gets rid of them entirely with Jackās help. Laces his fingers into Jackās silky hair and pets him, directs him. Jackās scalp is damp and hot with sweat. He looks up Samās body for further instructions and Samās nuts pull a little tighter with the eagerness in those eyesāthat absolute lack of embarrassment.
āSo good. Feels amazing.ā
Jack reluctantly lets Sam nudge him off his cock with his knuckles from below; Sam strokes himself, now fully erect, tingling with excitement, the slick warmth of Jackās spit. Jack huffs, wipes at his puffy mouth. Rubs Samās thighs, up his hips, his obliques. Sam hums and kneads his balls with his available hand, makes it good. Takes the edge off.
A point of his chin and, āGet up here,ā and Jack follows suit. Climbs him and Sam kisses him, tastes himself, lets Jack taste his own dick in return. He could makeāJesus, he could make this kid do everything. Not human; the lengths they could go toā¦! āLetās take this off. There you go.ā
Jack gasps but curls his now-naked ass right out for the searching push of Samās fingers between his cheeks. Trembles all soft and his dick smears against Samās thigh, and Sam lets go of his own cock to put that hand on Jackās ass, too, spreads him open to the room. Flirts three fingers up and down the tight pucker of Jackās asshole and Jack sighs for it, chases the touch. Sam scoffs. Rubs him firmer.
āGirls have another place, right here.ā Jack stares into Samās face in wonder as Sam rubs up-down his taint. āFor guys to put their dicks inside. But this works just fine.ā Back to Jackās asshole. Jack makes a small noise. āWorks just as good.ā
āCan we do that? I wanna do that.ā
Sam kisses that mouth. Speaks into it. āWhat? Put my dick in here?ā He presses down, breaches the kid just-so. Jack nods against him, slick and choppy. āYou sure? It might be a little weird, at firstā¦ā
āI want, Sam,ā so thatās that. Jesus. Oh, Jesus, Sam, what are you doing?
āOkay,ā and God, when had been the last time? Been a while, with a guy. Sam kisses Jack again to distract himself, keeps rubbing Jackās asshole. First time. No oneās everā¦! āLick my fingers. Here.ā Jack does. Sam watchesāhis dick throbs between their bodies. Back to Jackās ass, now slick with spit, and Jack obviously likes that. Gasps cute and his expression melts further. His brows flinch when Sam angles one finger in, breaches him just-so. āOkay?ā Slowly, Jack nods. āWait. Actually, letās⦠Here, lay down. Yes. Yeah.ā
Jack grabs the nearby pillow as Sam gets comfortable behind him, spreads his ass with his hands and dives right in. Eyes closed, tongue firm and proddingāJack gasps. Sam spreads him with both thumbs. Licks into him. God, yeah, been some time.
Sam grabs his cockānot very comfortable pressed into the bed, so he scoots low until he can kneel on the floor instead, pulls Jack with him to the edge of the bed. Jack lets him, trusts him. Sam works himself slow as he keeps eating Jackās ass. Squeezes and kneads one juicy globe of it and sucks, hums. Jackās pubes tickle soft against his lips, catch on his stubble. Jackās skin heats fast with the irritation. Beard burn. Samās nuts tingle with anticipation.
With Ruby, he neverāthey didnāt have to use protection. With her vessel dead and everything, there was no threat ofā¦well, anything. And technically, Jackās just a few weeks old. There couldnāt beāanything, right?
Samās thoughts double overāshame, want, pleasure, humiliation. He could just fish his wallet out of his jeans, grab the one condom heās got there or the bunch he keeps in his nightstand, together with the lube he has to grab sometime soon, anyway. But he could also justā¦not do that. Not like Jack would know any better.
Sam strokes his bare fist over his just-as-bare cock, spreads his precome over the sensitive head. God. God, heā¦wants.
Jack hums hot for the push of Samās thumb. Sam smiles, laps around the pumping digit.
āBetter, right?ā
Jack uh-hums and rolls his hips into the bed. Fucks himself back on Samās thumb, Samās tongue. āFeels nice.ā
āGood.ā Middle and ring instead of thumb. Tighter than just the thumb, but they do slide in. Sam peers up Jackās arched back. His cute bubble butt. āStill good? Yeah?ā
Jack mumbles, āMore,ā so Sam gives him that. Jackās face is turned to the side, barely-visible over the hitch of his shoulder, bedded on Samās squished pillow. Sam watches him closely, the tremors in his young face. The bite to his lip, feeling it out. He hums when Sam twists his fingers. When he drags them out, stuffs them back in. āāS good. I feel⦠Samā¦ā
āI got you.ā Sam lets go of his cock to unearth the lube from the very back of his bedside drawer. He drizzles some on his fingers, the tips still inside Jack, keeping him openāand feeds them back in with another gasp from Jack, a twitch to his legs. āGotta get you ready, first.ā
āThat, that isā¦!ā Jack groans, attempts to get his knees anchored to push back against Samās knuckles. Sam counter-pushes with his available hand on Jackās ass, keeps him pliant and right where he wants him to be. Jack huffs, frustrated. Complains, āSam,ā but Sam shushes, watches Jackās asshole stretch around three of his fingers. The slick makes it so much better. Easier.
āJust a little more, Jack.ā
A Nephil. They could use Jackās grace toāno, the boyās still too inexperienced, couldnāt control it enough. Sam licks his lip, is highly aware of the scrape of the sheets against the weeping tip of his cock. Just a little more. Jack can take him for sure. A Nephil. You canāt hurt him. Not permanently.
āSo soft,ā praises Sam, and pushes all the way to his knuckles to emphasize what he means. Jack moans into his pillow. Sam works the prostate apparently even only-half-humans are equipped with. āYou wanna try? I think youāre good to go.ā
Of course, āYes,ā and, āplease,ā and some more desperate blabbering Sam cuts short with a kiss. He pulls his fingers out, slicks his cock with the (generous) remnants of lube on his hand. Kid doesnāt even know what heās asking for, thinks Sam, and climbs the bed anew. Pulls Jack on top of him, makes him straddle Samās lap.
Kisses and, āEasy,ā and Sam holds his cock straight up but Jack needs a few tries to figure the angle out. Slips a couple of times and that feels good already, too good to be trueāand when Jack finally gets it, when Samās cock catches and gets swallowed up, itāsāoh, itās been way too long.
Sam groans, engulfed in too much slick heat at once. Jack trembles on top of him, circles his hips. Choppy, unsureāSam helps, guides him with his hands. Soft, careful, inch by inch. One step forward, two steps back. Jack gulps wet against Samās mouth. Sam swirls their tongues together, eyes closed.
āFeels good,ā slurs Jack. Sam hums, sucks at Jackās lip. āYouāre all hot. Like your blood is right under the surfaceā¦ā
Sam wants to tell him that it is. That Jack feels just as good against him. That heās throbbing wet perfection inside, clenching and surrendering and letting Sam inside him so easilyāeasier than most humans had, before. His grace, for sure, making it better and easier and better without him even realizing, working in the background, helping things alongā¦
Sam lifts his ass to nudge deeper and Jack lifts on instinct; Sam firms his hold on Jackās hip and stops him from squirming. Jack whines, no paināSam sucks on his throat. Thrusts up into him in careful, shallow rolls of his hips. Buries himself deeper, makes the Nephil take him, Luciferās sonāSam stares up into Jackās pleasure-tense face, the flutter of his loosely shut eyes, the gape of his pink mouth. Trusting. Enjoying. Heās enjoying this. He likes it.
Sam switches his hold from Jackās hips to Jackās ass. Grabs a handful each and push-pulls the kid like that, guides him to bounce on his cock. Despite the lube and prep, of course heās tight inside, but the ride is smooth and slick and perfect, just loose enough. Sam huffs, snaps his hips rougher, choppier. Jack gulps, dips down for kisses. Sam gives him those. Sucks at Jackās soft, pink tongue.
āWanna get on your back, yeah? Here. Let meā¦ā
Jack keeps his arms around Samās neck as his mouth flies open further for the new angle, for the push of his own knees towards his armpits. Sam has to muffle Jack with his hand heās getting so loud.
āShh, okay? Gotta be quiet, remember?ā
Samās own goddamn brain doesnāt want to remember, not with something soft and warm underneath him. Sam pumps into Jackās ass with intent, all the way, balls slapping against Jackās tailbone on every stroke. Jackās breath pushes hot against his palm, his cute little moansāhe tries, hard, but he canāt keep it down completely (not that Sam would want him to).
Sam hears himself pant, āYou like it? You like getting fucked like this?ā and Jack sobs as he nods into Samās hand, his entire body jostling under Samās thrusts, under Samās power. Sam could go harder. Sam can.
With another human, it would hurt them for sureābut Jack merely whines louder, still soft, still relaxed, obviously enjoying it. Sam groans, tucks the kid tight against himself. Lets him cling and moan against his shoulder and just pistons into him, makes the bed wobble with the impact. Dean might hear that. Sam decides Sam canāt care.
Jackās voice rises and then thereās a shudder, deep inside, drawing Sam further in, and Jack gasps for air and thereās a spill between them, sticky between their stomachs and Sam growls, overwhelmed, and stumbles right along without further ado.
He holds himself as deep as he can and justālets go. Unloads for what feels like ages, and he churns them together while he does because Jack wonāt stop squirming, egging him on for more. Whimpers cute and sucks at the teeth marks he left in Samās shoulder. Sam blinks, huffs. Trembling. Tucked against the kid.
His cock gives a last, satisfied throb inside Jackās ass, and Sam groans his sigh. He lets Jack pet his head, card through his sweaty hair.
āFuck,ā he mumbles, his brain now slowly trickling back online. Unfortunately. āFuck, Jackā¦ā
āThat was awesome.ā
Jackās voice is all thick. All happy. When Sam peels them apart just enough to check, Jack is smiling at him.
Jack tucks a bunch of wet strands of hair behind Samās ear. Jackās eyes glint with splinters of gold.
dean / jack + beardy dean loudly and sloppily eating out jacks hole
Bro, I got you.
warnings: age difference
includes: top!dean, bottom!jack, beard!kink, bear daddy dean because I say so
Jack reluctantly replaces Deanās hand that he slapped across his mouthāwith his own.
Hears and feels him shushing sweet, gentle, before he returns his hand into the back of Jackās drooping knee. Dips his mouth back down, back there, and Jack suppresses his next whimper.
Dean groans into his ass. Shouldnāt be this pleased, really shouldnāt, as far as Jack can judge that. As far as Jack can judge anything.
The summer heats the wooden raised hide to a mess. Jackās sweating through his tee and his shirt. His boots are heavy on his feet, but Deanās got him. Keeps his legs folded out and away and Jack doesnāt have to think. Jackās jeans lie in a sad puddle, next to their rifles in the corner of the hide; forgotten.
Nothing but the birds, the faint wind in the trees just outside, surrounding them. The drippy mess of Deanās mouth working him wet, loud, like this is a porn vid. Like Jackās something delicious.
Jack gets a thumb, an appreciative sound deep from Deanās chest. More tongue; the rough ride of Deanās beard against his taint, his already-rawed skin. Spit drools down his tailbone, tickles like crazy but he canāt, he canāt.
When he squirms, Dean just holds him down harder.
Low, āYouāre doing so good,ā and Jack huffs into his palm.
Itās Sunday and Iām feeling this one. (Kind of a sequel to Young At Heart.)
warnings: age difference, barebacking
includes: size kink, bottom!jack, top!sam, pwp
Jackās mouth pulls to a smile before heās even fully awake.
āHm. Morning.ā
He gets a kiss, sweet and tame. Shifts his legs wider, underneath the covers, so he can feelāmore. All of it.
Samās large hand, wrapped around him dry and firm; the stubble of his beard catching on Jackās cheek and the reciprocated, rough, āMorninā,ā and Jack huffs, pleased. Humps Samās hand until that retreats, dips down to cradle Jackās balls instead. Jack pouts. Sam chuckles, āWhat?ā and rubs two stiff fingers lower, down his taint, over the tight-again clutch of his asshole. āYou need somethinā, huh?ā
Sleepy, āDonāt stop,ā and Sam kisses him again, rubs his fingers nice and low and Jack wants to tell him, āNo, not that,ā but Samās already scooting down, below the safety of the blanket and swallows the warm line of Jackās dick down his throat, easy as that, and Jackās hips truly rise off the bed for that.
Jack pushes the blanket away so he can watch better.
That effortless bob of Samās head.
Jack tucks some of that gorgeous hair behind one of those darling ears. Shifts, uncomfortable, for the dry finger threatening to breach him. Sam stops his efforts to reach across the bed, behind the pillows where theyād stored the lube last night. Squirts some on his fingers and Jack sighs with relief because Samās got his mouth back on his cock by then; sinks one finger into his ass so so slow and careful.
Jack tells him, āFeels good,ā one hand in that hair just to hold onto something and Sam doesnāt reply. Just swallows around him, makes his throat go all tight and dreamy-perfect and Jackās eyes roll back into his head and he holds Sam down, right there, and Sam allows it. Not much of a challenge for him, after all.
Sam comes up eventually to ask him, āTwo?ā and Jack nods, lip between his teeth. Plucks at his own nipple once Samās guided his limp hand towards it and winces for the stretch. Sam watches his face, suckles tight on the head of his dick while he does. Wants to know, āOkay?ā and Jack nods again, and Samās face dimples up for that, and the wrinkles around his eyes smile their very own smile.
Jack huffs. Lets his head drop back into the pillow, feels his cheeks heating up pink. Drifts, relaxes.
Sam doesnāt ask again for the third. Shushes Jack sweet, his free hand on the quiver of Jackās lower stomach. Keeps sucking him off through all of it, and that helps.
Again, āOkay?ā
Jack cringes. āBig.ā
Sam laughs. āWell, yeah. Sorry.ā
āYou wanna try again?ā
āYou donāt?ā
Jack admits, āI dunno,ā and Sam pushes himself higher for that, kisses him on the mouth for that. A there-there, itās okay. Wet and warm and his fingers keep flexing inside Jackās ass, pull apart and Jack grunts, off-guard.
āHurts?ā
āNo.ā Jack swallows, searches Samās morning-soft face. Cups it, rubs his thumb along one cheekbone. āI want it,ā
and Sam tells him, āI know,ā and kisses him again, and his knuckles grind flush with Jackās taint and it feels odd, a little; still. āI know, baby. Itās okay.ā
āYou can use my mouth if you want.ā
Sam hums happy. āLet me handle this. Keep playing with those tits for me, all right?ā
Jack nods, frowns. Has Sam kneeling his way down, take a seat between Jackās legsāpushes his leg back until it almost-touches Jackās shoulder and Jack gasps, folded up and struggling, and Sam tells him to,
āHere, hold onto this,ā
and he does, and.
Samās thighs underneath him help keeping his ass tilted up. Helps Sam to get his other hand down there, too, and he slips both his pointer fingers in and pulls him apart, and.
Jack gets a hold of his dick without being told to. Babbles, āSam,ā and Sam just crooks his fingers harder, pulls Jackās ass wider until it feels weird and then some. Purses his lips, and Jackās chest hitches with the fat line of spit that disappears inside of him, like this is normal, like this is what itās for, and the next time he meets Samās eyes theyāre dark and happy and Sam smiles, asks him,
āYeah?ā
and uses two fingers on each side, uses more force, pries Jack even further apart.
Jack canāt speak.
Can only stare up at his boyfriend, gape like a moron because oh, oh snap, he canāt.
āYou gonna come?ā
Jack nods, stupid.
āYou want me to try?ā
Again, āUh-huh,ā and Sam huffs relieved; gets more lube and Jackās hand is hurrying the heck up. Mutters, āPlease, please,ā before Sam can lower himself down, keep him quiet with his tongue in his mouth. Pushes Jackās leg even deeper and Jack feels it, then, the insane pressure and weight of his cock slipping where Jackās wet and baby-opened, just enough, and Sam grunts like it hurts him as well and heās popped the head of it inside, then, too-much and hot and slick and Jack comes on that high, shoots messy and choppy over his own hand.
Gasps wildly while Sam groans, rocks himself deeper through the clutch of Jackās orgasm, curses under his breath and Jack hiccups, gulps for air, because gosh, oh, gosh, itās, heās.
āFuck, youāre so fucking tight.ā
Jack whimpers for the next two inches pumping into him, solid and violent and his hand slips on the hard plane of Samās stomach, and his mouth is open and sore and Sam looks soābeautiful, right now, so lost in bliss and focus and a snarl dances around his lip and he grits again,
āShit,ā
and rolls his hips, bumps the few inches heās worked Jackās ass up to home once, twice.
Dips his head down to kiss Jack on the mouth, drink down his noises. Has Jack scrambling like a bug for inches seven and eight and he seizes, then, a spasm down Samās back and Jack fucking feels that, moans with him as his orgasm takes him by surprise, whips him around and has his hips stuttering deep, involuntary.
āFuck. Sorryā¦ā
Jack promises, āItās okay,ā and feels dizzy with it, with the warmth spreading in his insides, with the flush of Samās chest, his face.
Another kiss to Jackās mouth. āIāll pull out, okay?ā and Jack nods, and it hurts. Gets Samās fingers soothing and rubbing over the gape of his hole right after, spreading the wet and the heat and Sam murmurs, āHoly shit,ā and, āSorry,ā and fingers the mess back inside Jack, eats at Jackās mouth in the sweetest apology.
Tags: alternate universe ā normal life, high school student jack, college student sam, teacher dean, student/teacher, age difference, possessive dean, possessive sam, jealousy, top!dean, top!sam, bottom!jack, ace!cas, ass to mouth, felching, spitroasting, barebacking, cuckolding, unreliable narrator, grooming
Wordcount: 5.6 k (for this chapter)
Summary: Dean lets himself get seduced by his exās/longtime neighborās kid. Things donāt turn out quite the casual way he hoped.
Note: @azrielrose tagged this gif set with #bb jack goes to school #sleazy teacher dean #oblivious protective if he knew bf Sammy and, you know what? We deserve this.
Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
ā Live Streamingā Interactive Chatā Private Showsā HD Quality
Anya is LIVE right now
FREE
Free to watch ⢠No registration required ⢠HD streaming
It's a shame Jack ships aren't popular cos he's just so sweet and earnest and would look really darling sandwiched between the Winchesters!
I'm hoping Jack ships will get more popular as time goes on but that might depend on whether or not the SPN writers kill him off. You're right. He IS so sweet and earnest. And sandwiched between the Winchesters? Hello, corruption kink!
Speaking of... have you seen the nsfw Dean/Jack art I reblogged? Not quite a sandwich but perfect all the same, right????