this weekend we’re taking inspo from our favorite dad and doing the absolute bare minimum. write a story, draw some art, make an edit or come up with some other very low-effort way to celebrate the beauty of dadfucking. make sure to tag @dadfuckerfest and remember: it doesn’t have to be perfect — it’s the thought that counts :)
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But for now, it was summer, and Dean belonged only to John. For the next couple of months, Dean had no exterior obligations. No sneaky school counselors trying to get him to reveal where they lived, no nosy teachers pretending to care about bruises. John could do whatever he wanted with his boy, and he knew Dean would take it like the champ he’d always been.
i finally got around to posting my fill for @dadfuckerfest Fun in The Son 2025 <3
Rating: Explicit
Warnings: Underage Sex
Relationships: Dean Winchester/Sam Winchester, John Winchester/Sam Winchester, Dean Winchester/John Winchester, Dean Winchester/John Winchester/Sam Winchester
Additional Tags: John Winchester Finds Out About Dean Winchester/Sam Winchester, Threesome - M/M/M, Non-Consensual Voyeurism, Pre-Season/Series 01, Full House of Wincest, Double Penetration
"What would Dad think if he knew his baby boy was such a whore, that little Sammy is spreading his legs for his big brother?"
When Dean overhears Jack masturbating through the vent that connects their bunker bedrooms, he's too turned on to think about the fact that sound travels in two directions.
Lucky for him, Jack appreciates the auditory company.
Even luckier? He's eager to add sight, touch, and taste to the arrangement.
ft. voyeurism, daddy kink, creampie, blowjobs, anal fingering, anal sex, come swallowing, jack's nephilim powers, and guilty dean winchester
It's quarter past two in the morning when he first hears it. The high, rhythmic squeaking of mattress springs, slightly muffled. It's a familiar sound. Something Dean's heard countless times through thin motel walls, originating at times from the rooms of strangers (thrilling) and his brother (hilarious) and his dad (utterly mortifying). But this is the first time he's ever heard it here, in his room in the bunker. With good reason, too.
The bunker typically only has between five and six occupants, and all their rooms are spaced apart.
Dean himself is in room 11, and he's never brought anyone back for a hookup - it's supposed to be a secret, secure base of operations, after all. Even if it wasn't, anyone who'd agree to follow a one-night-stand back to his underground bunker in the middle of nowhere would have to be out of their mind, and he's not about to invite that kind of crazy into his life. He's already got enough to deal with.
Sam's room, number 21, is in a completely different hallway, so even though he does share his bed with Eileen on a semi-regular basis, they're far enough away that Dean has been blissfully unaware of anything that they get up to in the dark.
Mary uses room 15, but even though it's close in number to his own, it's situated at the other end of the hall on the other side of the bathroom and a storage closet. Regardless, Dean's pretty sure she's never brought anyone back here for the same reasons he hasn't.
When he isn't sitting vigil in the kitchen or the war room, Cas typically uses room number 1 - chosen specifically so that he could always be ready to stand between the rest of the people in the bunker and any threat foolish enough to come through the front door in the middle of the night. Even if he was getting down and dirty on the regular - extremely unlikely, in Dean's opinion, seeing as the guy completely clammed up the few times Dean tried in vain to find out where his preferences lay - Dean wouldn't be able to hear it.
And then there's Jack, who until three days ago, was all set up across the hall from Sam in room 22.
Until three days ago.
What happened three days ago was that Jack had returned from a week-and-a-half-long hunt with Cas, discovered a nest of spiders living inside his suddenly-faulty light fixture, and decided he'd rather switch rooms entirely than attempt to deal with it.
So now, he's in room 9.
Right next door.
And Dean can hear his bed squeaking, echoing through the ornate brass grate that covers the air vent that connects their rooms.
Rolling onto his side, Dean holds his breath, and listens.
At first, he tells himself he's listening just so that he can be sure of what he's hearing, just in case he's wrong and it's something more sinister than Jack jostling his mattress. For nearly a full minute, with nothing but the steady, rocking squeaks to fill his senses, the lie is almost believable. But then -
"Fffucck," Jack moans, trailing off into something high and breathy at the end, and the squeaking gets a little louder, a little faster, and Dean's blood rushes to fill his cock so fast that it makes his head spin, because this is what he was really listening for. Waiting for. Hoping for.
Pushing out of bed, Dean pads across the floor to kneel beside the air vent.
It's louder, here. If he tries, if he ducks in close, he can make out more noises. Jack panting. His blankets rustling. The slick, wet sound of his hand stroking fast. Dean listens, breath held and greedy for more as he tries to guess what, precisely, Jack is doing. Fuck, what must he look like? Is he fully naked, or is he still in his cute little batman pajamas, just his cock out as he chases his release? Is he on his back, knees spread wide as he fucks up into his fist? Is he watching his own reflection in the mirror over his sink like Dean does sometimes, thrilling at the sight of his swollen cockhead slipping through the tight grip of his hand? Is he touching his balls? His chest? His mouth?
Dean would be kidding himself if he claimed never to have thought about him like this before, but until never had anything beyond a vague, shameful memory of the sight of him that first night. His naked body shrouded in shadow as he'd faced them down in the house in North Cove.
He hadn't thought much about Jack's body at the time - he was too shattered by everything that had just gone down, too terrified of the danger Jack represented - but later. Later, when the worst parts of Jack's arrival into the world had been set back to rights, when Dean got to know him for who he was, and had settled into something like the role of his parent so completely that Jack had started referring to him along with Cas and Sam as dad, and he'd tried to convince himself that his discomfort with the label was purely due to his own troubled upbringing.
And then, one day, his eyes had caught on the sweet swell of Jack's lower lip as he'd taste-tested something Dean was cooking, and he'd recognized deep, covetous hunger in his own gaze. After that, he'd remembered Jack's body clearly. The smooth, light skin of his taut stomach. His long, delicate fingers. The brown curls framing his pink, surprisingly thick cock. He'd remembered it on accident, and then he'd thought of it on purpose, and he'd spent more time than he'd ever admit under pain of death imagining with no small amount of shame the sounds he might make if Dean sucked him into his mouth. If Dean fucked him.
He'd deliberately tried to keep those thoughts to his time in the shower and his nightly bedtime jerk off sessions, and up until a couple of weeks ago, he'd been successful. But then Jack had called Dean into the bathroom one morning, still wrapped in a towel post-shower, to ask if Dean would teach him to use a straight razor. Dean knew immediately that he should've said no and sent him to Sam instead.
But he was weak. Desperate. Covetous. He'd said, sure, kid, and set about lathering his face as Jack made small, pleased sounds under his breath, like being touched by Dean this way was something he'd craved. He'd taken his time, scraped the blade gently over Jack's tilted chin in the steam-thick air of the bathroom, and he'd kept himself in check right up until he was done. Right up until Jack, still naked under his towel and perched on the edge of the sink with Dean standing close, had gazed up at him, lifting his fingers to Dean's stubbled chin as he'd said, "Thank you, Daddy. I knew you'd be gentle."
Jack had hopped down, then, and he'd left the room as though he hadn't just obliterated every decent, coherent thought Dean had ever had, and Dean had waited all of twenty seconds before he locked the door and unbuttoned his jeans. He'd jerked off right there in the middle of the bathroom, right into the warm, damp hand towel he'd just used to wipe down Jack's pink cheeks, and convinced himself afterwards that Jack hadn't meant it to sound like it did. That he just didn't realize that there was a big difference between dad and daddy. That his own reaction was just an anomaly. A one-time thing.
It hadn't been.
That was two months ago, now. He's lost count of how often Jack has done something seemingly designed to tease him. Stopping by Dean's room on his way back from the shower, shifting to lie with his head in Dean's lap when they're watching TV, only ever calling him Daddy instead of Dad or Dean when they're out of anyone else's earshot. All of it has built up, one thing after another, and though he's been afraid to let himself think it might be intentional, he's let himself fantasize plenty. Has replayed thank you, Daddy in his mind over and over again, each time picturing Jack's wide blue eyes gazing up at him, and every time he's come hard to the thought of painting his lips white.
So now, Dean's hand slips between his thighs without hesitation. He doesn't even think about it. Just pulls his cock out through the front of his boxers, and spits into his palm, and lets out a deep, animal groan as he gives the first stroke.
In the next room, the squeaking abruptly stops, but Dean doesn't notice right away with the sound of his own wet hand on his cock echoing through his room. He just keeps fucking into his fist, low, helpless unh, unh, unhs building in his chest until he finally hears Jack's bare feet hitting the floor. Light footsteps rapidly cross the room toward the vent on the other side of the wall, and Dean stops stroking, freezing in place. His dick throbs in protest at the sudden lack of sensation. It throbs again, harder, when Jack whispers through the grate.
"Dean?"
Shit, Dean thinks, and tries not to move. On the other side of the wall, he hears Jack pushing something aside - his laundry hamper, Dean's pretty sure - to get closer. He speaks again.
"Daddy? Can you hear me?"
Squeezing his eyes closed, Dean presses his lips together and tightens his grip around the base of his cock to stave off the far-too-fast orgasm that threaten to rip through him at those words. Fuck, Jack sounds so close - a few feet away at most. Cool air flows from the vent, and Dean imagines it's his breath, ghosting over Dean's cock and balls. Precum drools from his tip at the thought. Drips over his fist. He can't suppress the sound that shakes through his chest.
There's a sharp intake of breath as Jack hears him, and then - there. Wet strokes. Shallow gasps. Low, hungry whines as Jack starts touching himself again, spurred on by Dean's painfully obvious moan.
"Fuck," Dean breathes.
"Ohh," Jack replies, much too loud this time, and his strokes speed up faster than ever. "Oh, I can hear you."
"Shh," Dean tells him.
"Don't you want me?" Jack asks, sounding more needy than Dean's ever heard him, and he's helpless to keep from starting up again. He matches his rhythm to Jack's.
"No, I do. I do."
"Then why-"
"You just- you gotta stay quiet for me. It's gotta- gotta be a secret."
God, he hopes Jack doesn't ask why. Hopes he just accepts it at face value, so he doesn't have to admit aloud that if Sam or Mary caught Dean doing this with Jack, they'd throw him out on his ass. Cas might actually kill him. Guilt and shame war within him, and he knows he should put a stop to this now before it goes any further, but Jack is making such sweet little sounds, and begging him for more, and he's weak. He's so fucking weak.
"Want you for myself," he chokes out, and Jack's stroking gets frantic. God, he sounds so fucking wet. Must be leaking all over himself. Dean's fucking salivating at the thought.
"Me too," Jack gasps. "Just you, Daddy. Just want you."
"Fuck, Jack, you're- you got no idea what that does to me, kid," he says, though he's starting to wonder if that's true.
"You could show me."
"Yeah?"
"Please," Jack says, and the world around Dean dips out of sight for a split second before he's in Jack's room, zapped from one place to the other for the first time in years. He's still on his knees, but now he's on Jack's bed, with Jack looking up at him from the floor nearby with his hand on his dick. "Want you to show me."
He's naked, like Dean hoped, and as he stands to make his way closer to Dean, the light from his lamp makes his sweat-damp skin glisten. His cock is hard and curving up, the foreskin pulled back to reveal the glossy red crown, and as Dean watches, Jack fondles it. Slips his fingers down to tug lightly at his heavy balls before sliding them back up to the head, playing with his foreskin on the way.
"Baby, look at you," Dean murmurs, reaching for him as soon as he's close enough, and runs his fingers through the soft curls, teasing the base of Jack's cock. A thin strand of precum drips from his slit, wetting the sheets, and Dean tracks it with his eyes before dropping his hand to swipe through it. He raises it to his lips and sucks his finger clean - salty, sweet, bitter, perfect - and Jack wobbles where he's come to kneel on the mattress. Stares at Dean wide-eyed, like it never even occurred to him to taste it, so Dean wraps his hand around his cock, pumping it a few times until his fingers are slick and dripping. He raises them up in front of Jack's face.
"Open up for me, sweetheart. Stick out your tongue."
Jack does, mouth open wide, and Dean pushes three fingers in at once, smearing Jack's precum over his tongue.
"That's it, baby. See how good you taste?"
"Mm," Jack moans around his fingers, licking them clean, and Dean pulls his hand away, switching it for his mouth and kissing him deep. Jack is unpracticed - this is probably his first kiss, Dean realizes with a heady rush - and his technique is sloppy, desperate. Dean feels drool on his chin. Somehow, for the complete lack of finesse, it's the hottest fucking thing he's ever experienced. Jack is just hungry for it. Hungry for him. Uncaring about whether or not he's doing it right, because he just wants more, more, more.
He pulls Dean closer with a hand around his hip not because it's expected but because he needs it, wants it, never learned he had to be coy about it. His cockhead smears wet against Dean's stomach as they grind together, and Jack lets Dean push him to lay back, legs spread for Dean to nestle between them. The mattress starts to squeak again.
This could all be over too soon. They could both finish like this, just like this, and somewhere in the back of his mind Dean's still entertaining the notion that he's going to come to his senses any minute now. He's going to fully realize what a fucked up thing this is he's doing with his kid, and regret it, and weirdly, right now, the only part of that that's giving him pause is the fact that if he regrets it, he'll never get another chance to do it right. And he wants to. Needs to know how Jack feels on the inside; how soft and hot and smooth his ass will feel around Dean's aching cock. What sounds he'll make. If he'll beg. If he'll be demanding. If he'll be able to come just from Dean fucking him, or if Dean will get to suck him off after. Take his son's seed into himself after pumping him full of his own.
Sucking in a gasp, Dean pulls out of the kiss, and meets Jack's wild-eyed gaze. He already looks wrecked. His hair is a mess where it's been rubbing against the sheets, and his mouth is bitten red, and Dean doesn't want this to end. Not yet.
"You have lube?" he asks, and Jack just blinks, clearly having no clue what he's talking about. Dean swallows. Pushes back the voice in his head that's telling him that Jack's cluelessness is one of many reasons they shouldn't be doing this, and strokes a hand down Jack's stomach. "You wanna use that mojo of yours to grab if from my room? Purple bottle, under my pillow."
The air shifts slightly. Jack holds up the bottle.
"Perfect," Dean tells him. Jack beams like he's just been given a gold star.
"What is it for?"
"How about I show you?"
Biting his lip, Jack nods, and he's looking up at Dean with such trust, his eyes so bright and guileless, that Dean has to take a moment. Take a breath. He worries the lid of the bottle with his thumb.
"You want to be close to me, right?"
"Yes, Daddy," Jack says.
Dean takes a shuddering breath.
"Okay. This is... I'm gonna use this to open you up, and then I'm gonna- I'm gonna push inside you. Right here," he says, reaching down to rub over Jack's furled hole. It's warm and velvety under his fingers. Tight and sweet. Jack nods, but something in his eyes is strained now. Uncertain. Dean leans down to kiss him, softer than before. He sucks Jack's lip between his own before he pulls back. "You nervous, baby?"
"No," Jack lies, and then, looking away, sheepish. "Maybe a little. Is it going to hurt?"
"Let me take care of you."
"You do. I trust you."
"How about I kiss you there, first?"
"Mm, I like kissing," Jack murmurs, almost sounding drunk with it, and Dean takes it at permission. Kisses him once more before he starts trailing down, sucking and tonguing at every inch of skin he passes until he gets to Jack's cock, and slides his hands under his thighs to lift them as he licks a strip from root to crown, teasing his tongue along the ridge as he goes, and almost goes cross-eyed at the sound Jack makes. He doesn't linger there, though he thinks he could suck Jack's dick all fucking night, could spill all over himself just with the sound of Jack's breathless gasping. Just gives one last, deep suck to the tip before he shifts lower, spreading Jack's cheeks to get a good look at his tight pink hole.
He runs his thumb over the silky skin of his taint, staring as Jack's asshole pulses, like it's already begging to be filled, and dives in. Licks and sucks and works it over until it's soft and pliant under his tongue, spit-slick and shiny, and Jack is writhing, grasping at the sheets and begging him to stop, to keep going, to do something, and Dean clicks open the lube. Wets his fingers and slips one inside in a smooth, steady motion that has Jack arching up off the bed, digging in with his heels.
He moves quickly, then. Thrusts his finger deep into Jack's hot core until he can fit another alongside it, and another, and another, until he's got four fingers stretching him wide, middle finger rubbing relentlessly against his prostate. Jack's cock is lying against his stomach in a puddle of precum that keeps on growing, and Dean can't resist leaning down to suck it back into his mouth, savoring the taste of Jack's desperation.
"Daddy, please, please-" Jack whimpers, getting too loud again, and as much as Dean wants to stay right where he is, torturing Jack's prostate and until he bursts warm into Dean's mouth, he takes that as his cue. Slips his fingers free of Jack's sloppy hole and shuffles back to kneel between his thighs. With one hand tight under Jack's knee, spreading him wide, Dean grasps his own cock and guides it into him, pushing deep in a single, heavy thrust that envelops him in perfect, aching heat. Jack cries out with the force of it, and Dean ups the ante. Pulls out to the tip and then drives back in just as hard, quickly setting a frantic pace until the squeaking mattress is the least of their worries, the entire bedframe knocking against the wall and rattling the contents of Jack's bedside table.
Let them catch us, Dean thinks wildly, plunging deep into Jack's body, the slick grip around his cock making him mad with lust. Desperate to come. To fill this boy. Let them see. He's mine, he's mine, he's-
"Mine," he growls, and Jack whines, clutching Dean's ass with one hand and the headboard with the other, scrambling for purchase as his dick pulses between them, spurting come all over his taut belly, coating his smooth chest. With his free hand, Dean swipes his fingers through it, lifting it to smear over Jack's open mouth. Feeding it to him before he leans down to suck it from his tongue.
"Fuck, I could live on your come," he says, drawing Jack's lower lip between his teeth and tugging before he lets go and licks back into him as Jack goes loose-limbed, rendered barely conscious in his pleasure.
"It's yours, Daddy," Jack mumbles, grasping ineffectually at Dean's arms, his eyes hazy. "Dad."
Somehow, that's what does it.
Not the Daddy.
Dad.
Jack called him Dad. Dean's cock is spearing into him, and Dean's feeding him his own come, and the room is a cacophonous whirlwind of sex and sweat and desperation, and Jack called him Dad.
"Ohh, fuck, sweetheart," Dean hisses, and his body seizes as he pumps his load deep into Jack's pulsing asshole. Pumps again, again, feeling like it's draining everything out of him, and when he slides out, pulls free, he doesn't hesitate to push Jack's thighs to his chest and dive in with his tongue, sucking his own come from Jack's sloppy, puffy hole as Jack sobs in thigh-twitching, overstimulated pleasure. He only relents when Jack's fingers find his hair, tugging sharply, and then he crawls back up. Lets Jack pry his mouth wide with his fingers to coax Dean's come out and onto his waiting tongue.
He swallows every drop, then smiles, gummy and wide. Shockingly innocent.
"Can we do that again?" he asks, and Dean flops to the bed beside him, spreading his arm wide when Jack moves to snuggle against him. "If we keep it a secret?"
We shouldn't, is what Dean should say.
He doesn't.
"Yeah," he says, and shivers when Jack reaches down to cup a hand around his spent cock, holding it gently like it's just a part of hugging. Like he doesn't know any better. "If we keep it a secret."
Merry Christmas! Turns out I did a fic about it! Which was a surprise to even myself given that I hate Christmas, but there was a @dadfuckerfest prompt that fit an idea that's been in the back of my head for months, and when I sat down to write it, I had the thought "what if there was snow?" The rest just happened.
An Archive of Our Own, a project of the
Organization for Transformative Works
1.2k, one-sided Dean/John, pining Dean Winchester
Prompt: "Dean pining for his dad, maybe fantasizing about the things he can’t have?"
A very merry Christmas, sang John Lennon, and a happy New Year. Let's hope it's a good one without any fear. All Dean could do these days was hope. From Virginia to Missouri, from Missouri to Minnesota, and now from Minnesota all the way to Colorado, he kept going by imagining what would happen when they arrived at the motel.
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.
✓ Live Streaming✓ Interactive Chat✓ Private Shows✓ HD Quality✓ Free Actions
Free to watch • No registration required • HD streaming
An Archive of Our Own, a project of the
Organization for Transformative Works
hi hi my second fill for @dadfuckerfest this time is samjack/winkline!!! please go check out the other fills and prompts, and leave some more prompts if you want to!!!
John wipes the sweat off his forehead as he watches Dean float in the pond with his eyes closed and his head tipped back a little, his throat long and exposed and oh-so-vulnerable. In any other situation, John probably would have barked at him for being so reckless, so careless with his own safety. But it’s only the two of them out here, trying to escape the relentless summer heat in the pond hidden behind a copse of trees in the backyard of the dilapidated farmhouse that is their home for the week.
Taking a sip of his lukewarm Miller Light, John reclines, shielding his eyes against the sun rays filtering through the canopy of leaves above. They had been brought to this little nowhere town for a possible rugaru, but in the last two days, the trail had run cold. Still, John had decided to stick around a couple more days just in case it reared its ugly head again, rather than leaving too early and having to come back again.
And even if he’d never admit it, it’s nice to take a little break, to let his aching body rest. His back pops as he stretches, and he groans softly. Case in point.
The water sloshes as Dean moves, and John can just imagine the ripple of the surface against Dean’s body, lapping at the cotton boxers clinging to him like a second skin, leaving little to the imagination.
“You should come in. It’s nice.” Dean’s voice carries in the silence around them, deeper than it used to be. His boy is all grown up now, a man. John dreads the moment Dean will figure out he doesn’t need his father anymore. “C’mon, dad, please.” For now, that moment hasn’t come.
