#younger Dean

[jayjay-thejet-plane]

GUESS WHAT more tiny dean 4 u <3

(they fell asleep during the movie)

pst hey you! this is a continuation of these sketches: pt.1 pt.2

Close-ups and still shot below

[thebaddestb-tchinthisclub]

Dean woke up feeling so strange. On the last hunt a witch had hexed him. But, he hadn’t died and he didn’t feel any immediate difference when she did. So he thought he was safe to go to bed for the night. He slid out of bed and stood noticing he stood much… shorter. Dean frowned and looked down at himself. His bare legs were so scrawny. “No…” A scratchy voice whined out and Dean slid across the floor to get a look at himself in a mirror. “Oh my fucking god!!!” He shouted and fell backwards onto the floor. “I look like a fucking actor from Degrassi!” Dean shouted now touching himself all over being freaked out by his much younger body. “The fuck happened to me!?” Dean’s scratchy scream addressed the other.

[weaksspot]

long as i am loving you you’ll never be alone long as you keep wanting me around

[acecroft]

Dean Winchester in SUPERNATURAL 7.01

[animasolaoriginal]

I n f a t u a t e d ♦️THREE

CHAPTER ONE◾TWO THREE FOUR◾FIVE SIX◾SEVEN◾EIGHT◾NINE◾️TEN ELEVEN

He finds out the girl he picked up on a whim is the perfect candidate. So innocent, so submissive already, with just the right amount of Daddy issues. But she still has a lot to learn, and he's determined to teach her everything.

ruthless nightclub owner ❌ innocent young woman with a crush

WARNING: NSFW! Explicit sexual content. Age gap. Size difference. Dubcon elements. Dom/sub dynamic. Sex toys. Fingering. Cunnilingus. Orgasm denial. Oral sex/deepthroating. Anal play. Creampies. (For more tags, check it on AO3!) // WORDS: 4.9k

TWO 🟥 THREE 🟥 FOUR

He's surprised how quickly she adjusted to her new surroundings, to the things he's asked of her, forced on her. Maybe she's still feeling the after-effects of the drug he's given her last night, maybe she doesn't understand the situation just yet, maybe she's simply the perfect candidate for this. To stay here, for him. She's barely putting up any fight, only seems embarrassed most of the time, but the way she's sucked him off has shown him how eager she really is.

Even though she still has a long way to go. Too fucking innocent.

She's that little ball of hair and limbs on his lap, curled up, melting into him, small hands that have been around his cock now gripping his shirt. Feet tucked under his thigh, deep little breaths against his chest. It's been only a few hours, and she's already so submissive. He's almost disappointed he didn't get to break her first. But maybe her defiance is yet to come. He's certainly looking forward to it.

His phone chimes on the coffee table, and he throws a quick look at the display. The courier is here. Good. Without a word, he stands, picking her up effortlessly. She hums against him, leans into him as he carries her into the bedroom. When he puts her down on the bed, leaning over her for a moment, he meets her hooded eyes. So pliant, so innocent. He can't help but lean down further to press his lips to hers.

She melts into the mattress as he pushes her deeper, putting his weight on her, elbows on either side of her shoulders as he gives himself a few minutes of a bit more much-needed pleasure before he has to leave her. She's hesitant at first, but as soon as he slips his tongue between her lips, her own jumps into action. A groan escapes him as she kisses him back with more and more confidence. His fingers dig into her hair, their tongues wrestling, his cock stirs back to life against the fabric of his pants.

He leans back abruptly, breathing a little harder, the girl beneath him panting as well, her lips parted and red, glistening. Her eyes on him. “I gotta take care of something,” he tells her quietly. She only blinks. “Be a good girl and wait here for me, okay?” The way her pupils dilate when he calls her that makes his stomach tense up. He's noticed it before, how she reacts to his praise. It's an intoxicating sight.

He crawls off her and stands, looking down at her small frame. White lace was a good choice, accents her innocence perfectly. Those little embroidered flowers barely cover anything, but it's still enough fabric to keep it interesting. She's beautiful, the way she lies in front of him, chest rising and falling, that flutter to her stomach, the little twitch to her thighs as she presses them together and tries to hide her sex. He raises an eyebrow at that.

“While I'm gone,” he says, a smirk growing on his lips, “I have a little task for you.”

He steps towards the nightstand and pulls open the first drawer, randomly picks some of its contents and throws them onto the bed next to her. Her eyes widen when she follows the gesture and stares at the colorful toys. He picks up one of the smaller dildos and braces himself on one arm as he leans over her.

“I want you to be very wet when I come back,” he whispers, gently taking her hand and placing the object onto her small palm. “Understood?”

She still looks at him in shock, and he can already tell she's never used any of the things he's presented her with. Another challenge, another thing he's willing to change. He leans back and looks down at her, head cocked to the side. His eyes narrow slightly when she doesn't reply.

“Understood?” he repeats a little harsher.

A tiny gasp escapes her and she sits up, nodding frantically. “Yes, sir.”

His hand finds her cheek, a gentle caress, thumb running over her bottom lip. He watches her intently. “Good girl.” The shiver that runs through her amuses him immensely. Patting her cheek, he then turns away and leaves her to her own devices.

Returning to his phone, he sends a message to the courier, and minutes later there's a chime on the door. His men are good, and fast, and when he looks through the things in the box that was brought up to his place, he nods in contentment. The things she left in the club, a jacket, a phone, case stuffed with some money, some keys and her ID. He's surprised that she's actually 19, when she looks quite a bit younger. Not that it really matters. His eyes scan her name, memorizing it. Fits her.

There's a folder tucked into the side, all the information they could gather on her, and the more he reads, the wider his smile gets. She is perfect, a random pick, an instinct, and it has still been the best choice. Alone in the big city. He checks her phone, swipes through pictures and messages. There's only one new message, someone congratulating her. Not many social contacts, no Mom or Dad or other relatives. Does explain a few things though. The girl definitely lacked the presence of a proper authority figure in her life, or at least someone who could give her the attention she needs, someone to hug her even, guide her through life, tell her what's right or wrong. No wonder she's so overwhelmed with his advances, yet strangely compliant at the same time.

Daddy issues.

What a perfect little thing that found her way into his clutches. He turns the phone off and puts it back into the box, then locks it securely in the safe in his office, before he focuses on the bag that came with the delivery. Clothes he ordered for her, more underwear mostly, some dresses, shoes. He doesn't plan to take her out much, not yet, so she won't need too many clothes anyway. They're just an illusion of safety for now, something she feels more comfortable in, before he'll take that away as well.

Grabbing the bag, he returns to the bedroom – and freezes. The bed is empty, except for the array of sex toys on the blanket. Untouched, unmoved. And the girl is gone. Something hot rises inside him, his hand tightens around the straps of the bag. He checks the bathroom, also empty. When he opens the door to his walk-in closet, he hears a soft little gasp, before his eyes move down to the far back where she's curled up on her side, wide eyes staring at him from under her lashes.

Like a beaten animal – and he hasn't even done anything to her yet. Not really, anyway.

He puts the bag down on a shelf and approaches her slowly. The dildo he gave her lies in front of her, just as untouched as the rest. She curls up even more, a little ball of hair and limbs, white lace in stark contrast to the dark rug she's lying on. He crouches down, hands resting on his knees as he watches her.

“What are you doing here, baby?” he asks quietly. “Are you hiding from me?”

She sniffles, shakes her head. “No,” she mumbles, wide eyes following his every move. Why is she so skittish all of a sudden? The drugs probably wore off. Poor thing.

He doesn't care. His hand reaches out and grabs her elbow, pulls her closer. A little yelp escapes her. He sits down on the floor and pulls her between his legs, she struggles against him but his fingers close around her arm, squeezing harder than he intended. She winces, a deep shudder rushing through her small body when he drapes her legs over his thigh, making her lean against him. One arm securely around her, holding her with enough authority that she stops squirming, he raises the other hand and grabs her chin, makes her look at him.

“What happened?” he asks, looking at her, scanning her face, fear and shock evident on it.

She averts her eyes, chewing on her lip. He squeezes her chin.

“Look at me.”

She does, with a soft little whine, blinking rapidly, eyes glistening as she meets his gaze. “M'sorry...” she mumbles.

“For what?” His voice is stern, and she frowns at his tone.

“For... for not... doing... what you told me...” she whispers, the first tear falling from her lashes. “I... I couldn't...”

He raises an eyebrow. “Why not?”

Her cheeks are bright red by now, her eyes moving over his face in frantic little flutters. “Felt... wrong...”

He watches her, letting go of her chin to move his hand straight between her legs. She flinches and yelps when his fingertips brush against her panties. The fabric is a little damp, warm against his touch. He doesn't hesitate and slips a finger under the hem, testing the waters. She turns her head away, whining softly as her blush spreads over her shoulders. “Do you need my help?” he whispers.

She only stiffens in his hold as his finger glides along her slit. Warm, wetter than he expected. He doesn't know why she was so stressed about this task or thinking she failed him. She's perfectly responsive. His lips brush against her temple.

“Tell me you need me to help you...” he breathes against her.

Her thighs twitch. “I... I need you to... to help me...” she mumbles out, burying her face in his chest in a little gesture of embarrassment. So fucking cute.

“Good girl,” he hums and kisses her forehead while his finger slips between her folds, gathers her slick and promptly dips into her entrance.

She flinches, but keeps quiet, leaning into him as he nudges her legs apart with his thumb. His finger slips in and out of her, her tight walls gripping him in a way that makes his cock throb. Her wetness gathers around him, quiet squelching sounds filling his ear. She lets out little noises of discomfort, barely-there whines, almost-sobs but in a way that doesn't seem too distressed. She's slowly adjusting, relaxing in his hold, her breaths deeper.

His thumb finds her clit, and when he pushes gently on it, she wails a little louder, her legs trembling, her small hands gripping the front of his shirt as she melts into him more. He keeps drawing tight circles around her nub, his digit pushing deep, in and out, faster, her wetness runs over his hand. The moment she becomes really still, a sharp inhale cutting through the air, he stops, pulls away, and she looks up with her lips parted, almost pouty, eyebrows furrowed, disappointed.

He smirks at her and brings his wet finger to her lips. She doesn't fight it when he slips it into her mouth, rubs it over her tongue and along her gums, pushes deeper. She freezes again, stares at him, but then she closes her lips around his finger and sucks, her tongue flicking around it, licking up her own juices. He pulls it out with a wet pop and leans down, capturing her mouth for a quick, deep kiss, sucking on her tongue, tasting her. She melts into him, clinging to him, but as soon as she starts to relax again, he lets go, leans back, leans around her to grab the dildo still lying behind her on the floor.

“Here,” he says and puts the small pink object into her hand. “If you want to finish it, do it with this.”

She stares at him, eyes wide, fingers curling around the toy, her face flushed. And then she shakes her head, catching him off guard.

“No?” he whispers, raising his eyebrows. “Are you sure?”

Her breaths are loud through her nose as she holds his gaze, not saying anything.

He narrows his eyes. His first instinct is to grab the toy and shove it deep into her tight pussy himself, but he refrains, pushes her off his lap and stands, then grabs her wrist and drags her out of the closet. She stumbles after him and yelps when he throws her onto the bed.

Scrambling to her knees, her lips parted and trembling, she stares at him with her eyes wide in shock. He ignores her for now and walks to the bedside table, rummaging through the drawer until he retrieves a little teardrop shaped object, bright pink as well, smooth silicone with a little antenna.

A high-pitched squeal escapes her as he grabs her and pushes her onto her stomach, one large hand on her lower back, holding her down as she starts to squirm. “Stay still or this'll be more uncomfortable than it should be,” he tells her through gritted teeth. She stiffens, her breaths loud and frantic as she white-knuckles the sheets.

He moves the toy between her ass cheeks, pleased to see the butt plug is still in place. Nudging it slightly, he makes her wince. Pushing her legs apart a bit more with his knee, he slides her underwear aside, grabs her thigh to steady her and lets the small vibrator glide between her slick folds, and it's only a little push of his thumb before it slips into her, swallowed up by the tense muscles of her pussy. She lets out a strained whine. He wipes his palm over her mound gently, then tugs on the fat string until he finds the thicker bit at the end. The button clicks audibly when he presses it, and she gasps when the first vibrations shake her body. It's low, but still definitely overwhelming for her.

He puts her thong back in place and grabs her elbow, dragging her off the bed. Her legs are trembling, the low hum between her twitching thighs barely audible, but he hears it, sees her reaction to it, feels his blood pumping into his cock, the throbbing almost painful, and he wonders why he's taking his time with her. He could have had her last night, this morning, any time he wanted, fucked her hard and mercilessly, any hole he desired, and yet he waits, eases her into it, with a patience (or restraint) that surprises himself.

Sighing loudly, he grabs her hand and leads her out of the bedroom, she follows him on shaking limbs, too stunned to protest now. They reach the open kitchen, and he grabs her waist and sets her on the island, hears the faint clanging noise when the base of her plug hits the marble top. Spreading her legs, he steps between them, braces one arm on either side of her, stares down at her darkly.

Her eyes are wide, glistening, shock and uncertainty on her face, but there's also a deep blush and a tightness to her lips as she fights the sensations pulsing through her small body. Her hands fidget between her legs, a nervous little gesture. He rips them away, tells her to sit on them. She does with a bit of hesitation as she watches him with bated breath. He leans in, lets his breath fan over her cheek, then kisses the corner of her mouth, and there's a jerk in her neck as she turns her head, trying to meet his lips.

He pulls away before that, exhaling through his nose. His hands move over her legs, thumbs brushing along her inner thighs until he pushes them against the damp fabric of her underwear. Her wetness seeps past it already, staining the white satin bit, and he licks his lips at the sight. His restraint is slipping, he can't help it, he can smell her arousal, and it's driving him insane.

In one swift motion he grabs her hip, pulls her to the edge and leans down to press his mouth to her inner thigh, quickly kissing up the soft skin to where the little pink antenna pokes out of her. His free hand tugs at it, then he drags her panties aside and closes his lips around her folds. She yelps softly, body jerking against him. His fingers dig into her flesh, hold her in place as he laps up along her slit, gathers her sweet wetness on his tongue, drinks her up like a man parched.

She whimpers when he sucks on her clit, teeth grazing her soft, sensitive skin while he fumbles with the toy and presses the button a few more times, feeling the vibrations increasing, her hips jerking, thighs pressing against his head. Her noises are getting louder, helpless whines and mewls as she squirms on the counter, hands still squished under her legs while he continues to eat her out with a passion that he hasn't felt in ages.

Holding her with one hand, he tries to counteract her uncontrollable twitches, while his other hand rubs over her thigh before his index finger pokes at her entrance, following the toy inside. It's thrumming hard against her tense muscles, and he pushes it around a little with his finger before he finds the right spot, and that's when she really wails, body spasming against him, the heels of her feet thudding loudly into the cabinet as she tries to ground herself somehow.

He holds the toy pressed to her g-spot, still sucking on her clit, eyes moving up to watch her lose it in front of him. She's arching her back, head tilted upwards, chest pushed out, arms trembling before she can't keep her composure any longer and pulls her hands from under her legs and grabs his hair, two sets of small fingers with an iron grip that surprises him. Either to push him away or hold him right there, he isn't sure. Whatever the case, he lets her, gives her that one moment of control.

Her walls tighten around the toy and his finger, rhythmic clenching, her orgasm is so close, she's right on the edge, and it's that moment that he hooks his finger around the toy and pulls it out, leaning back, slipping from her suddenly limp fingers, and leaves her throbbing and panting, watches her deflate as her orgasm slips away again. A whine escapes her, and she falls backwards onto the counter, body convulsing without release, hiding her flushed face behind her shaking hands.

He straightens himself, licks his lips and then his finger, puts the vibrating toy on the counter before he turns it off. She's sobbing now, overwhelmed and left hanging. Poor thing. But it's not over yet.

Hooking his hands under her arms, he hoists her off the counter and pushes her down on her knees in front of him. She's too surprised to react, slowly lowers her hands and looks up at him, tears streaming down her red cheeks. Without a word or command, he unbuckles his belt and opens his pants, then snaps his fingers at her. Despite her trembling state, she follows the order instantly, automatically, that inborn desire to please stirring within her, when her small hands move up to push his pants and underwear down enough to free his erection.

The initial touch is almost enough to push him to the edge and over, but he braces himself, puts his hands on his hips and watches her as she closes her fingers around his length, slowly stroking up and down like he's shown her. Her eyes stay on him, watching him closely, and he tilts his head, pressing his lips into a thin line, a slight furrow between his eyebrows. He sees her swallowing, and barely a second later, her lips brush against his hot skin, the contact enough to coax a little groan out of him.

He watches her closely as she moves her lips up and down his shaft, tongue licking along his bulging veins, circling his tip, flicking over his slit, before she opens her mouth and takes him deeper. She's a little hesitant, careful, one hand still on his girth, the other braced against his thigh as she slowly bobs her head, lips closed around his tip, cheeks hollowed, the little suction really tempting his self-control. He wants her to find her own pace, get better on her own, learn to pleasure him properly, but he also really wants to fuck her throat and make her choke on his cock. The struggle is real.

His hands move to her head, a gentle little caress, fingers sliding through her hair, slowly nudging her closer, she shifts on her knees, the hand on his thigh pulling her into him. Her eyes are closed now, and he can see tears forming under her lashes as she keeps moving her head back and forth, the hand that's tight around his girth keeping her from taking him deeper. He feels her warm mouth, that little tongue flicking around his tip, hot and wet, sucking softly, almost meditatively, and he can't help it, he bucks his hips slightly against her, his cockhead poking into her cheek when she turns her head with a little muffled whine.

One of his hands moves down to grab her chin, holding her in place, head slightly tilted, as he repeats the same motion, pushing into her mouth, watching her cheek bulge. He hasn't noticed it before, but she's a natural at keeping her teeth out of the way, her jaw opened wide enough to allow him to slip in and out fairly easily. Her eyelids flutter open, and she meets his gaze, her eyes glistening, pupils dilated more than he has expected. She's enjoying this, huh?

He smirks at her, moves her head a little and tilts her chin up before he pumps his hips a little harder against her, more of his cock slipping into her small mouth. She stiffens, both hands now gripping the fabric of his pants, bracing, a sliver of panic in her eyes. He watches her closely, the grip on her chin hard as he concentrates, holds back, fights the urge to just fuck her cute little face. His breaths are quick and loud through his nose.

She holds still, doesn't fight it, and he uses that submission to move faster and eventually slips deeper, feeling his tip prodding the back of her throat. She gags almost immediately, a sudden reflex, her body convulsing against him, fingers digging into his legs, and he lets her pull back with a deep cough, saliva dripping from her lips. But he only lets her relax for so long, before he pushes his cock back into her mouth, deeper, to that spot once more, and she gags again, spit filling her mouth, coating his tip, yet this time he holds her head in place, and she lets out a pained little howl, muffled but clearly distressed.

Sighing, he grips her hair and pulls her back again, lets her catch her breath, swallow the excess spit. Tears stream down her face, her eyes are red, eyebrows furrowed, a helpless expression mixed with something like indignation looking up at him. A low laugh escapes him, and he grips her chin and pulls her back, cock slipping into her mouth, her tongue scraping along the underside, frantic little breaths through her nose, warm on his skin.

“Relax,” he tells her, and strangely enough it's that command that lets him slip deeper, past her gag reflex, further into her tight throat. It's only a few seconds though before she gags yet again, fingernails sinking into his legs, that little uncontrollable twitch as her body fights the new sensation of having her throat stuffed. She gurgles, desperate to breathe, too panicked to relax anymore. He pushes her away, and she splutters, spit and precum flying from her trembling lips, her shoulders shaking.

It takes all of him to loosen his grip on her, but when he lets go of her chin and her hair, inhaling deeply, she looks up almost surprised. Bracing his arms on the counter behind her, he closes his eyes, fighting the urge to make her choke again. That feeling when her throat tenses around his tip, squeezes him, it's something he enjoys a little too much, almost as much as watching her suffer through it, with her tears streaming down her face and her hands digging into his legs, that desperate struggle for control.

He'll force that urge right out of her, soon. Another time.

“Suck,” he grunts instead, standing still as he leans over her.

She resumes her ministrations, one hand around his girth, pumping and stroking, while she closes her lips around his tip again, sucking and licking it, keeping it far away from the back of her throat. She's shaky and sloppy, her wet slurping noises echoing through the room, her body still trembling, but she somehow manages to bring him right to the edge after all. He feels his balls tightening, his stomach tensing up, his cock throbbing in her hold. His hands itch, clenched into fists on the counter, his body shivering. So close. So fucking close...

A deep groan escapes his throat, and he leans back abruptly, grips her hair and pulls her off him, a sharp inhale coming from the girl beneath him. Her eyes are wide as she looks up at him, and he just ignores her, hooks his hands around her elbows and pulls her to her feet. She's that tiny body he can manhandle however he wants, and she ends up on her stomach on the counter, short legs dangling off the edge, feet kicking before he cages her in, one hand on her lower back, the other moving straight to the little shiny knob sitting between her plump ass cheeks.

Before she can comprehend what's happening or try to fight him, he drags her panties aside and pulls the plug out with a plop, puts it on the counter with a clang, before he grips his throbbing cock and pushes the tip against her sphincter. She lets out a surprised wail, her hands reaching back to swat him away, but he only grabs them and bends her arms behind her back, held by one large hand. She still struggles as he pushes further, forcing his tip deeper. He doesn't have time to prepare her properly, he's close to exploding.

She whines, writhing on the counter despite his unrelenting hold, and he watches her tight muscles give way to him, the grip almost as good as her tensing throat. His crown slips in, and he stops, letting it rest there as he strokes his shaft hard and fast, until he feels that tension finally dissolve. He comes with a deep grunt, arching his head back, feeling his cock throb and twitch in his hand and in her ass.

Spurt after spurt shoots into her tightness, filling her up until the first drops seep past the tight ring of muscles that clench around him involuntarily as she squirms helplessly, sobbing softly. When he relaxes against her, shoulders sagging, the grip on her arms loosening, he wishes he'd prepared her better, made her more pliant, open her up properly to take more of him. But this'll do for now. Once the twitching subsides, he gently pulls his cock out, watching her ass gape for a moment, his thick seed slipping out almost immediately.

He pushes it back in, feeling her tense muscles close around his finger. Then he grabs the plug and brings it back into position, holding her down again as she starts squirming more, the cold metal slipping into place, plugging up his warm cum. He exhales deeply once he is done, and when he lets go of her and steps back, he can't help but slap her plump cheek once for good measure.

She sobs louder, but remains lying on her stomach, legs dangling off the edge, immobile, all the fight gone from her body. He watches her as he puts his spent dick back into his pants. “What a good girl you are,” he whispers, noticing a wave of goosebumps rippling over her skin. His hands are on her round rear, gently sliding up and down, thumbs teasing between the cheeks. He fixes her thong, nudges the plug, smirks when she flinches at the motion.

Then he grabs her waist and pulls her off the counter, turning her so he can scoop her up into his arms. Despite her reluctance and the fact that she's still crying softly, she leans against him, needy little fingers digging into the collar of his shirt. No matter how hard she fights him, fights the sensations and experiences he gives her, she is clearly craving this, his attention, the care he gives her afterwards, the gentle moments after however rough he treats her.

It's a good dynamic. It'll work, he's sure. She will be absolutely perfect.

He carries her into the bedroom, carefully putting her down on the bed. She immediately rolls onto her side, knees pulled up to her chest, wiping at her wet face, avoiding his gaze as he watches her closely. When he leans down, she flinches, but he only grabs the edge of the blanket and drapes it over her small body.

“Rest now,” he tells her, straightening back up. “I'll order us some food.”

TWO 🟥 THREE 🟥 FOUR

End notes: Just a little side note on where this story is set: it could be literally anywhere (where there are skycrapers or a downtown area with taller buildings). I did not have a specific place in mind, could be any major American city, could be a bigger European city, anywhere you like to think of. It doesn't really matter anyway. (And if it is set in America, just imagine his club to be one of those more lax ones where the drinking age isn't 21 or at least nobody cares about it.)

Also, you may have guessed it, but our male protagonist is a little bit more than just a nightclub owner. I won't go into too many details, just know he's influencial, if you'd like to call it that. And definitely intimidating enough for anyone to bow before him, not just our poor girl who might just be a little in over her head at this point.

Thank you for reading! Next chapter on Monday!

TAG LIST: @qmsvpx @cyan1decandy @bimbos-are-angels

AO3 / / / MASTERLIST

CHAPTER / / / ONE◾TWO◾THREE◾FOUR◾FIVE◾

SIX◾SEVEN◾EIGHT◾NINE◾️TEN◾ELEVEN

[flowersintheimpala69]

Thinking abt s1 Dean taking care of older Sam.. because he might technically be younger but he’s always be the big brother.. and Sam may be older and grizzled and larger but when Dean touches him and pushes his hair out of his face and pets him and tells him it’s gonna be okay he crumples in on himself and he’s deans baby brother

[crocodilenjoyer]

he's our little brother. take care of him.

anne carson - antigone / alec benjamin - if we have each other / dan pearce - single dad laughing: the best of year one / kodaline - brother

[sunbleachedf4wn]

thinking again about endverse wincest.

[brotherscain]

endverse dean would be so skeptical of stanford sam at first, but once he comes around to it, he’s a man obsessed!! he’ll stare and never let sam from his side and call him sammy in a tone so soft and endearing. sam touches him back with a hesitance dean lost years ago and dean could be rough but he likes how the gentleness surprises sam. likes that he’s not asking the hard questions yet, like where his sam went. sammy hasn’t been touched by dean in two years at this point, he’s dying for it. dean’s worse off, splaying sam out underneath him and teasing out all the weak spots he’d forever memorized. he should feel guilty. the best thing to happen to him just miraculously came back and he’s defiling it. but it’s the apocalypse, the sam he spent his whole life with is dead inside the devil somewhere and the world’s going to end. maybe it was a sign. one last gift from an absent god. dean keeps going back to 22 years old, wondering how he ever got himself to stay away from this for so long.

[jayjay-thejet-plane]

UM HI GUYS im still thinking about de-aged dean… and while the drawings were merely platonic/weirdcest and innocent in nature, the brain worms have wormed their way into a different *ahem* part of my brain👍

I was making notes on my phone for drawing ideas but it got out of hand and idk how much of it will get drawn (if any welp)😗

‼️WARNING‼️ READ AT YOUR OWN RISK

Contains: pseudo-underage (deans body is de-aged but his brain is still old) and dub-con (dean manipulates/pushes sam into doing stuff) would be rated E on ao3🫡

note: it is implied at they are already in an established relationship with each other before this

(this is riffing off the idea of sam just carrying dean around the bunker all day when dean is deaged in “about a boy” after sam picks dean up to hug him after seeing dean drowning in his old hoodie (as in my previous sketches)

De-aged Dean getting a boner while Sam is carrying him [sams sits down at some point in this]

“that a gun in you pocket or are you just happy to see me haha” sam teasing

Dean turns beet red

“I CANT CONTROL IT OK puberty sucked the first time around”

Sam looking kinda shocked; Dean trying to wiggle away/get down from Sam’s arms, Sam locks his arms around him to keep him there

“Wait! Dean its okay, [i didnt mean to make fun of you] [you can stay i dont care] [you dont have to leave] [you can just rub up against me if you want]”

Sam also blushing now, looking sheepish (he feels guilty about being attracted to de-aged dean and doesnt want to take advantage of him)

Dean biting his lip looking up at sam through his lashes “…are you sure? I can just go and-“ (dean thinks sam isnt attracted to this body and feels insecure about it)

“NO! I mean, yeah it doesnt bother me, its nothing compared to what we’ve done with older you😅(its fine its not like im fucking you like this or anything)”

Dean under his breath “…i wish you would just fuck me”

Sam looking hopeful and horrified at the same time “What?” (punched out breath)

“nothing” (sounding resigned) dean tucks his head under sams chin or into his neck as his hips rut begin to rut against sams stomach

Sam eyes screwed shut obviously trying to control himself as dean continues to wiggle his hips around rubbing on Sam’s abdomen and making little breathy moans and whimpers (mouth open panting/kinda drooling)

[dean pushing his face against sams begging him to kiss him “please sam- ah, just once please i need you” “dean i cant- if i start i dont think i’ll be able to stop” “you dont have to stop- please sam”]

Sam offers him a tissue either right before dean cums or after, dean pulls open his pants/pushes down his shorts

[and sam sees his little nearly hairless cock straining/hard and flushed red/bright pink, its shiny and leaking and it makes sams already chubbing up dick twitch in his pants against deans ass, which makes dean gasp, grind back against it and keen “sam… help me please, i know you want to, cmon” (dean feels more confident now that he knows sam is affected by him even in this body)] OR [sam helping dean up on his knees (dean is shaky + weak limbed) to help pull his shorts down to clean the cum up some, sam sees his little cock covered in cum all pink and hairless “oh god-“ “you can touch it if you want sammy, i want you to touch it” (dean biting his lips, holding onto sams shoulders to support himself)]

Sam lifts dean up and pulls his legs over his shoulders to suck deans little prick into his mouth to [clean him off] [suck him off] (it easily fits in his mouth) dean curls up over sams head and ruts into his mouth “oh FUCK sam please please please i need-“

Sam pulling off deans prick to kiss his soft stomach eyes closed looking blissed out voice breathy “what do you need baby?” [sam loves how this young dean tastes and smells]

Dean keens and bites his lip “mmph” “inside- i need you inside me, please [sammy im so empty]” (dean almost crying and using one hand to push the hand sam had near his ass to hold him up closer to his hole or to hold a cheek to the side)

Sam open his eyes and looks up at dean with disbelief(?) picks dean up (which makes dean cry out and cling more to him) and carries him to their bed and lays dean down and removes his shorts before hovering over him and grabbing lube from the bedside table OR making dean suck on his fingers to slick them up

Sam starts rubbing his hole with a lubed up thumb while massaging deans cock in his mouth OR rims dean and THEN pushes a thumb into him (other hand resting on deans cock, the whole thing is covered by his big hand and dean wiggles his hips around to rub against it)

after a bit “please sam i need more, i can handle it, please” between moans/whimpers

Sam looking determined(?) takes his thumb out and pushes two lubed up [or spit slicked] fingers in and continues fucking into deans ass with them, dean arches his back and cries out, shoving himself farther onto sams fingers, (hes full on crying now? certainly has tears on his face) and cums hard all over his stomach

Sam is tenting his jeans hardcore (lol) and dean is limp and fucked out, sam panting hard leaning back on his knees away from dean, hand pushed against his crotch trying to control himself and relieve some of the pressure [cock straining painfully against his zipper] dean whimpers at the loss “sammy no- come back, i need you to hold me, need to kiss you please sam” (getting panicked)

“Shhhh its okay baby, ive got you” sam leans down and pulls dean up back onto his lap and holds him close, kisses his forehead/cheek, dean turns/tilts his head to kiss sams lips with an open mouth, sam resists for a second and then lets out a strained moan and gets a hand into deans hair to move his head however he wants and shoves his tongue into deans mouth to plunder it (wet and messy), sams other hand pulls at deans waist (dean is naked or in just a shirt/sweater at this point) and shoves his own crotch into deans naked one, a high pitched moan punches out of dean [rough denim over sams large hard on against deans soft skinned crotch and limp little prick is a LOT (but dean loves it)] and he shoves himself even closer to sam/arches his back, theyre rutting against eachother (dean is getting hard again and his cum from earlier is making quite the mess and wet spot on sams jeans). Dean reaches a hand down to touch sams covered dick

He gasps “its so big” [hes used to how it feels in his adult hands], sam snaps out of it at that and pushes dean back to hold him an arms length away, chest heaving

“What am i- dean i cant- [youre just a kid]”

“[Im not actually a kid and you know it] Just let me help you sam please, you dont have to put it in me, just let me use my hands, please” dean looks desperate, puppy dog eyes at 100%, straining against sams hold

Sam looks conflicted but he’s so hard it hurts and dean begs so prettily “…okay, you can- just your hands dean”

Deans right back on sam, kissing him and helping sam open up his pants and rubbing his little hands over sams cock straining in his underwear, dean leaning back to look down at it in awe (the size difference is getting to him), he pulls sams cock out [sam hisses at the feeling of deans soft bare hands against the sensitive skin] and pushes his own prick against it, both of them staring down at sams cock dwarfing deans, making it look even smaller, dean ruts his dick against sams [close up of its little head pushing againt sams cock] sam is biting his lip trying to stay still, full body tensed

“i want- please let me put my mouth on it i want to taste it so bad please sam”

“Dean- “

“I wont push myself i promise… i trust you not to hurt me” (dean trusting him is what cracks the sliver of self control sam has left at this point )

Sam swallows hard and nods, lets go of dean so he can duck his head down to sams crotch. Dean looks a bit nervous as he stares at it, he open his mouth to kitten lick at the flushed head and groans at the taste of sams precum before wrapping both hands around it and going to town mouthing at the head. He pulls back to beg “can you- i want your fingers in me again sam please”

Sam lets out a breath and gulps “yeah, okay, um” he turns dean around and lays down so dean has his face in sams crotch and sam has a nice view of his ass, sam gently pushes two fingers into deans sloppy hole and massages them right up against his prostate

“Ah- yes dont stop sam dont stop” dean goes back to holding and licking at sams cock, hes rocking back onto sams fingers and his prick bounces as he moves, leaking precum all over the place, adding to the mess from his earlier orgasms. Dean is trying his best to put sams cock in his small mouth but he can barely get his lips around the head. Sam pushes a third finger into dean and it surprises dean who comes again and gets sams cock farther into his mouth than he had before as he groans, the vibrations paired with seeing dean come untouched, feeling his ass clench down and flutter around his fingers and dean choking a bit on his cock (throat spasming) make sam lose control for a second and he thrusts up into deans mouth, dean gags and sam quickly pulls him off of his dick “oh fuck, dean im so sorry baby are you okay??” [he feels incredibly guilty especially since dean trusted him not to hurt him] Dean is whining and pulling against sams hold trying to get back to his dick.

“Let me- saaaam im fine it felt so good please give it to me i want more”

“Dean youre going to hurt yourself” sam is straining to not give in

“Fuck my mouth or fuck my ass just get it in me i need it in me please sam please” Dean begging

Sam snaps and flips them over to hover over dean and nudge the head of his cock against deans loose wet hole [still twitching from his orgasm]

“Yes yes yes sam please fuck me please”

“Fine. You asked for it, but you tell me if you need stop, promise me you’ll tell me if you need to stop”

“I promise i promise just put it in me already please i need it”

Then sam thrusts hard into deans shaking body and fucks dean stupid, making him come AGAIN before sam himself cums inside while fucking into deans overstimulated twitching body, dean is SOBBING

After: dean shaking and crying, arms wrapped around sams neck head tucked into his shoulder, sam has one hand wrapped around deans body to hold him up and close and one hand supporting them on the bed, he is still inside dean (dean cried out and begged him to stay there when he went to pull out) “shhhhh baby youre okay, you did so good, you were so good”

[i love you baby]

“Im hic- im okay- i just need a- a moment”

“i know dee i know, just let it out, take your time, that was a lot. Can i carry you to the bath now or do you want to stay here a bit longer”

“We can hic- go to the bath but can you stay inside me please?”

“sure dean, just hold onto me and i’ll stand up”

In the bath: Dean eventually gets off of sams cock and he sits in front of sam in the tub, lets sam clean his body gently and clean the cum and lube out from his ass carefully as dean whimpers, sam is praising him and soothing him throughout

Dean leaning back against sams chest, relaxed and nearly asleep “we should yawn- do that again once my ass recovers, was hot as fuck” then closes his eyes [asleep?]

Sam is red and has a hand over his eyes but he doesnt deny it

————————-

ANYWAYS yeah feel free to add to this or write it or draw it or anything bye🫡

[thesmuttyduchess]

[salembehindbars]

When I say I like older men and dilfs, I mean, I am only into older men who aren’t into younger girls. I need an older man who doesn’t want me because the second he does, it will disgust me that he is an older man who is into younger women

(I dont know if that makes sense but that is how I feel)

[lilacpaperbird]

in my mind, girl!dean is not a feminine tortured coquette that sleeps with older men because she has daddy issues, yk. in my mind, girl!dean is... just like dean. she wears that fucking leather jacket everywhere. he keeps her hair short because it's practical. she has a drinking problem and she eats like shit. she showers with a 3-in-1 shampoo and the cleanest thing on her is always her gun. she has a stash of sleazy porn mags and she likes to go after boys younger than her

[animasolaoriginal]

I n f a t u a t e d ♦️TWO

CHAPTER ONE TWO THREE◾️FOUR◾️FIVE SIX◾️SEVEN◾️EIGHT◾️NINE TEN◾ELEVEN

She wakes up in his bed without any recollection of how she got there and what happened. But does it matter? She'd be stupid to deny a hot, rich guy like him, wouldn't she? No matter what he demands of her...

ruthless nightclub owner ❌ innocent young woman with a crush

WARNING: NSFW! Explicit sexual content. Age gap. Size difference. Dom/sub dynamic. Praise kink. Dubcon elements. Fingering. Butt plug. Hand job/blow job. (For more tags, check it on AO3!) // WORDS: 5.8k

ONE 🟥 TWO 🟥 THREE

She wakes to a low thumping inside her head and a strange taste on her tongue. It's a known hurt, usually brings up memories of parties, too much to drink, dancing till her feet give up. But she can't remember anything. And it's painful to even try to remember. It gets worse when she opens her eyes and finds herself in an unknown room.

On a bed. A stranger's bed.

Her first instinct is a little flutter of her heart, panic, unease, frantically looking around while she sits up slowly and bunches the covers around her shivering body. A quick feel beneath them gives her a short-lived peace of mind. She's not naked, but some of her clothes are missing. She swallows thickly, clears her throat, tests her voice.

Only to suddenly meet the stare of a man sitting opposite the bed, on a couch between two large floor-to-ceiling windows showing a familiar cityscape. She freezes when he looks at her with dark eyes, a little glint in them, a smirk on his lips as he watches her. She wraps the blanket tighter around herself.

“Good morning,” he says, voice deep, a low thrum in the air.

“Hi,” she replies hoarsely, her rapid heartbeat echoing inside her hurting skull.

“How do you feel?”

“Head hurts,” she mumbles, not even wondering why he would ask that. Not wondering anything at that point, really.

“There are some painkillers on the nightstand, and water,” he replies with a nod to her left.

She follows the hint and sees a large glass of water and two small pills next to it. And her skirt, neatly folded on the edge of the table. Leaning over to grab the things she needs to hopefully feel better, she keeps her eyes on him, cautious, hesitant. Once the pills are down and the glass empty, she inhales deeply, that awful taste gone from her mouth. One less thing to worry about. Though it gives her the chance to feel other things.

Like the stickiness between her thighs.

Shifting on the bed, she looks around, dares to break eye contact, gets a lay of the land, or at least the room. Huge. Minimalist. Just the bed, two bedside tables with a tiny lamp each, no clutter, a large couch on the opposite wall with a pompous rug in front of it, two doors to her right, one on the left. A single large plant in one corner. Fancy wooden floorboards, white walls adorned with exquisite trim. A luxurious light fixture built for a museum above her.

She looks back at him, her mind racing. “Do you remember me?” he asks when she meets his gaze. She nods. Of course she does. She's been coming to his club for weeks, and he finally noticed her. She has no idea how she ended up in his bedroom though.

He stands up, a tall frame clad in a fancy black suit with a white shirt, handsome and intimidating. Somehow even wealthier than she expected. His steps are confident as he approaches the bed, his eyes never leaving hers. “Did we –” she starts quietly, scooting back a little as he sits down on the edge, facing her.

“Did we what?” he replies, his lips curling up slightly. “Use your words, darling.”

She shivers, a strange feeling coursing through her as his words sink in. “Did we have sex?” she then manages to say, feeling her cheeks warming up.

“No,” he says, braced on one arm as he watches her closely. “Do you want us to?”

Now her head is burning, and she looks away with a sharp inhale. His laugh is low and rough. She breathes loudly through her nose.

“Is that not why you came to me?”

Their eyes meet again, she bites the inside of her cheek. Has it been that obvious? It's been a stunt, a challenge from her friends, a silly little dream. She's had no idea it would actually work. Whatever it was that made it work. There hasn't been much planning, to be honest, with how drunk she's been, high on adrenaline and endorphins, too happy to care about possible consequences.

She flinches when he extends a hand and brushes his fingers against her side, curls them into the blanket. Her heart is racing as he slowly pulls it away, exposing her. She doesn't fight it, just freezes, hugs her knees to her chest, crosses her feet, when the covers fall away. Why doesn't she fight it? Why should she? He's hot, rich, gives her the attention she's been craving her whole life. She'd be stupid to push a man like that away.

But he doesn't touch her, just looks at her, eyes wandering over her body, while she sits on the bed, shivering, waiting, her mind spinning.

“Why are you here?” he asks, and she frowns at the question.

“Why did you bring me here?”

His eyes meet hers, his gaze intense, dark, somewhat hungry. There's a playful twitch to his lips, and he leans back, licking them. “Probably the same reason why you approached me,” he replies quietly, his voice low with an almost dangerous edge to it. “To fuck you absolutely senseless.”

His words make her gasp, eyes widening at the bluntness. Still she feels that throb between her legs, the warmth seeping into her panties. She shouldn't be this excited, and she forces herself to not make it too obvious.

Grinding her jaw, she looks away, towards the large windows. She has no idea what time of day it is, the sky is gray and the buildings she can see are only various shapes in a different shade of gray. She must be downtown, it's too high up to recognize anything. She's never been in any of the taller buildings of the city before.

His hand is on her foot, long fingers curling around it, and she whips her head back to him, inhaling sharply. “Is that not what you want?” he whispers, his thumb drawing circles on her ankle.

She breathes faster, no longer as sure as she's been last night. It's not helping that she cannot remember anything other than approaching him at the bar. There's the faint image of being pinned to a wall, making out in the darkness. But nothing more. She swallows, staring down at his hand.

“I... I don't know...” she mumbles. His thumb stops moving, he tilts his head at her.

“Are you a virgin, sweetheart?” he asks bluntly.

She clears her throat, ears burning under her hair. “Uh, yeah,” she admits, shifting uncomfortably on the bed. His touch feels too warm, too invasive all of a sudden.

“Do you want to leave here a virgin?”

She doesn't like the way he says that, it makes goosebumps ripple over her skin. He takes his hand away, and she looks at him. She's expected him to grin at her, look suggestive, leering and creepy, somehow, but his expression is full of genuine worry, lines on his forehead, a furrow between his brows. Dark eyes as intense as ever, but warmer. And so freaking handsome it's really distracting.

Chewing on her bottom lip, she can only shake her head. His face relaxes, the hint of a smile grazing his lips. “Good,” he says and stands up. She flinches at the sudden movement. “Go take a shower,” he then orders, pointing to one of the doors to her right. “There's some stuff you can use in there. Wait here when you're done.”

His tone is authoritative, not leaving any room for complaints or hesitation. “Yes, sir,” slips out of her almost automatically, and he smiles wider.

“Good girl,” he says, winking at her as he walks around the bed towards the door leading out of the room.

He leaves her sitting on the bed, shivering, a strange tension in her stomach. She doesn't even try to comprehend why his last two words to her felt like something she's never experienced before, like a warm shiver running down her spine, a caress deep within her. An itch she never knew she needed to scratch.

The bathroom is almost as huge as the bedroom, black and white tiles, warm wooden tones in the vanity and cabinets lining one wall to accent the lack of colors. There's a big bathtub in front of a large window, the lower half of it covered by expensive looking blinds, showing only the gray sky beyond. The shower is enormous, could easily fit five people. But she's alone in it, standing under the spray, still pondering what is happening. What she's agreed to.

Has she agreed to anything though? Well, denying to want to leave or to remain a virgin couldn't be more straight-forward.

What's gotten into her?

Sure, he's handsome, wealthy, owns a night club, lives in an apartment overlooking the city, quite a catch, but he is still a stranger. Just a man she's grown a little infatuated with over the last visits to his club. She's always seen him lounging at the bar, looking over the dance floor, dark eyes scanning the crowd. She's seen him hooking up with random girls, leading them into the back.

And she wanted to be one of them.

A silly wish, and now she stands naked in his shower. It's almost too good to be true. No, it's foolish, dangerous even. She doesn't know him. Did she really agree to be taken back to his place? She can't remember. Why can't she remember? The painkillers work, but the low thumping is still there, muffled and no longer as agonizing, but still there, in the back of her mind, like a mass of unanswered questions burning through her nerves.

Inhaling deeply, surrounded by the steam of the shower and the faint scent of him that clings to the room, she tilts her chin up and lets the water run down her head, over her warm face, through her hair down her back, little rivulets following the curves of her body. Gosh! She's never felt this nervous before.

But in the end it's just sex, isn't it? Better to lose her virginity to a rich guy in his fancy place than to a drunk guy in a dirty alleyway. It can't be that bad, right?

When she steps out of the shower and grabs a towel, her gaze falls onto the little pile on the vanity. Rubbing her hair, she inspects it – and freezes. It's underwear, white lace with the hint of shimmery satin, intricate, barely able to cover anything, bra and panties, but that's not what makes her insides churn. It's the little metal thing lying on top, the teardrop shape with a small handle like a knob, adorned with a big sparkling jewel. She may be inexperienced, but she knows exactly what it is. He left her a freaking butt plug.

Shivering at the thought of putting anything up her ass, she ignores it and focuses on the packaged toothbrush he's given her. Putting all her energy into brushing her teeth, drying her body, blowing hot air through her messy hair, she quickly forgets about the implication that special gift holds. When she puts on the white underwear, she leans towards the mirror and wipes at the steamed-up surface to look at herself. A gasp escapes her.

Not only does she look so different in the lace set (the white little embroidered flowers barely covering her nipples or her sex, the thong sitting deep between her butt cheeks, leaving nothing to the imagination), but she also notices the large bruise on the side of her neck.

Her finger traces the deep purple mark, and she shivers. The memory is faint, but she can feel it as she remembers last night (or what remains of it), how he's sucked on her skin, his warm mouth, even warmer tongue, licking over his work. She swallows thickly. The throbbing is back, low inside her, her stomach tense. It's either fear or anticipation, she can't be sure just yet.

When she exits the bathroom with her hair cascading down her shoulders, trying to cover more of her chest, she lets out a little yelp when she sees him sitting on the couch again, one leg over the other, lowering his phone when he notices her. His eyes are on her immediately, and she tries to cover herself with her hands as she walks backwards to the nightstand, trying to grab her skirt.

“No need,” he says, his voice firm, and she freezes, hand extended, fingers brushing over the fabric. She frowns at him, and he shakes his head. “You'll only wear what I tell you,” he adds, and the harsh tone lets her exposed skin pebble, his words barely registering inside her suddenly empty mind.

She inhales sharply, holding her breath. She's never felt this exposed and vulnerable, embarrassed that he can see her like this. Even though he'll probably see a lot more of her very soon. The thought scares her as much as it excites her. To say she's conflicted is an understatement.

When he stands up abruptly, she flinches, and even more so when he is with her in a few quick strides of his long legs. His hand closes around her wrist, pulling her towards him. She has to look up at him now, her chest rising and falling faster, heart thundering loudly, something hot gathering deep in her belly. He watches her closely, a stern look in his eyes, as his other hand slides down her side, over skin and lace, curves around her rear, and she shrieks when she feels his fingers dipping into the cleft between her ass cheeks.

He lets go of her, his eyebrows furrowed. She bites her lip as he scrutinizes her darkly, before he turns around and enters the bathroom. He comes back with the little metal thing between his fingers, and she feels her stomach tensing up even more.

“You didn't like my little gift, huh?” he says quietly, almost menacingly.

“I... I did–didn't know how to... use that...” she admits in a breathy whisper.

“Hmm,” he hums and steps closer to her, one hand cupping her face as he leans towards her, the other holding up the plug, dangerously close to her lips. She stares at him, stiffening, eyebrows knitted in confusion. “Open your mouth,” he tells her.

She hesitates, and he pushes his thumb and forefinger into her cheeks, forcing her jaw apart. A muffled whimper escapes her, and she grabs at his wrist instinctively. His gaze darkens.

“Tongue out,” he whispers, his voice that low thrum in the air, stern and strict, and she knows she shouldn't hesitate anymore. Slowly she extends her tongue, flat, mouth open, her eyes wide as she watches him when he lowers the metal object onto it. “Come on, lick it or it goes in dry.”

A cold shiver crashes through her, every muscle clenching in anticipation. Struggling to swallow hard (which isn't easy with her mouth open), she flicks her tongue around the cold object, holding his gaze. He pushes the plug deeper between her lips and forces her to close her mouth around it. She feels her eyes watering as he pushes it in and out, coating it in her saliva, warming it up. It's humiliating, to say the least. But she's afraid it's only the beginning...

He plops the plug back out of her mouth, then quickly pulls her against him as he sits down on the edge of the bed. She can barely react as he manhandles her onto his lap, draped over it, ass raised, stomach pressing into his hard thigh, hair falling over her head. She claws at the fabric of his pants, squirming on his lap, her head spinning as she tries to understand what's happening. “Hold still,” he tells her, but it's almost an instinct to writhe more, fight against what he has planned.

The sudden slap of his hand against her ass cheek is loud in her ears, and it takes a moment before the pain attacks her senses. A pathetic little cry escapes her, and she kicks her feet. Another slap to the other cheek makes her yelp again, the sting to her soft skin like nothing she's ever felt before.

“Hold still!” he repeats, and she whimpers, buries her head in his leg, and forces herself not to squirm, despite the throbbing pain. She feels tears in her eyes, her mind blank with shock. Her breaths are frantic, little wheezes of panic. “Shh,” he makes, his hand gently caressing the irritated skin now. She relaxes a bit, but only until he pulls her thong to the side and she feels something cold pressing against her sphincter.

“No!” she whines out, unable not to squirm, and he sighs deeply. Instead of spanking her again, he brushes his finger along her cleft, warm, a teasing tingle, a little rough, but better than that hard plug. Until she hears and feels him spitting on her, something warm and wet gathering on her skin, his finger spreading it around slowly, and then he dips his fingertip into her tight hole.

She gasps and tenses up immediately, only making it worse. He doesn't care, slowly works his finger deeper, wriggling it slightly, easing the tight muscles. She bites her lip hard enough to draw blood, quietly whimpering, frozen in place. Surrendering to the fate she seemingly called upon herself. By the time he forces the plug into her ass, she's sobbing, unsure how to feel about the object poking out of her – and what that says about his other plans for her.

He helps her stand then, big hands on her upper arms, looks down at her as she looks up at him through her tears. Sighing deeply, he wipes at her wet face, smoothing her hair, shaking his head. “You'll learn to love it,” he whispers before he leans in and presses his lips to hers for a soft kiss, a gesture she hasn't expected after whatever just happened. His words barely register, the underlying threat (or promise?) for more overpowered by her own shame and confusion.

Leaning back, one hand on her face, thumb on her bottom lip, he watches her, something dark glinting in his eyes. His other hand moves along the curve of her spine before he gives her another slap to her tense ass cheek. She cries out, flinching away, feeling her muscles clenching around the metal thing inside her. He only laughs and grabs her hand, pulling her after him.

She puts her bare feet into the ground, and he looks back at her, eyebrows raised. “C-can I... get something m-more to wear?” she asks quietly, voice hoarse from crying.

He tilts his head, chuckling. “No need,” he says again. “It's just us, baby, don't worry.” She doesn't know how to feel about that.

“Please?” she tries again. “I'm... cold...”

“Are you now?” he whispers, his hand moving up to her chest, his thumb pressing against her nipple through the thin fabric of her bra. “Doesn't look like it.”

She lowers her head, inhaling sharply, blinking away new tears.

“Little advice, darling,” he says, putting his finger under her chin and making her look at him. “Never lie to me.” His words are cold, his eyes dark as he stares at her. “Understood?”

She swallows, nods slowly. He grabs her chin, narrowing his eyes. “Y-yes,” she says, quickly adding: “Sir.”

He lets go of her and gives her a smile, his hand on her head, patting it softly. “Good girl,” he whispers. Her insides tense up, something cold trickles down her spine while something warm throbs inside her core.

He takes her through his vast apartment, but she's too focused on walking behind him to really look around, his hand big and tight around hers, her bare feet tapping over the wooden floor, and she feels practically naked in that sorry excuse for underwear he's forced her to wear.

Force, there's no way around it now. He's forcing her to do this, no matter what she might have agreed to. That plug in her ass that twitches with every step she takes? She didn't want that and yet it's there now, tightly gripped by her confused muscles, the shiny knob brushing against her thong, giving her shiver after shiver. But she's too stunned and overwhelmed by it all to even think about finding a way out of this.

Is this still what she wants? Has she ever truly wanted this, whatever this is? She has no idea, she just knows, somehow, that whatever he tells her to do, she'll do it if he keeps calling her good girl. It's a strange realization, two simple words, but they make her feel special, like she's never felt before. Just thinking about it makes her core ache, her muscles clench, her nipples perk up.

She's caught in her own mind when he stops in front of a set of couches, a u-shape in a large room, a plush rug beneath her feet, more of those big floor-to-ceiling windows, the gray city beyond the glass, so far away it seems. He watches her, she realizes when she looks up at him with a slight frown, amusement glinting in his dark eyes. Letting go of her hand, he sits down, leans deep into the cushions, both arms resting on the back of the couch.

“Straddle me,” he says quietly as she shifts nervously on her feet in front of him. Swallowing, she moves her gaze from his eyes to his crotch, to his wide spread legs. A confident sitting position, exuding dominance. And she knows she shouldn't hesitate, but it still takes her a moment to follow the order.

Slowly she moves closer, one leg on either side of his, cautiously pushing them together a bit to allow her to kneel on the couch and sit down on his strong thighs. Her hands find his shoulders for support, and she watches him as closely as he watches her. Her heart is racing when she settles on his lap, trying not to focus on the fact that her legs are spread wide enough to give him a good look at the scandalously thin fabric of her thong, barely hiding anything.

He tilts his head as she retrieves her hands and folds them in front of her sex, head lowered, shoulders stiff, still unsure what she is even doing here. Suddenly he grabs her waist, large hands splayed around her body, making her look back at him with a little gasp.

“Tell me you want this,” he whispers hoarsely, his eyes boring into hers. It's not a question of consent, it's another command, and she can't help but agree yet again.

“I... I want this,” she says under her breath.

“Yeah?” he asks, raising an eyebrow. “You sure?”

She inhales deeply. “Yes.”

“Say it,” he urges, fingers digging into her soft flesh. “Tell me what you want.”

“I... I want...” she starts, chewing on her lip, her eyes wandering away from him, her cheeks burning up in embarrassment. “I...” Her mouth feels dry. “I want you to... to...” She swallows thickly. “...to sleep with me...”

His laugh sounds almost mocking. She looks up with her eyebrows furrowed, her lips pursed, discomfort written all over her face. “So fucking innocent,” he mutters, shaking his head, amusement or malice making his lips twitch. “Say you want me to fuck you. Come on, use big girl words, baby.”

She presses her lips together, shifting on his lap. “I... I want you to... f-fuck me...” she repeats quietly, clenching her jaw, trying to hide the shaking of her voice, embarrassment burning deep inside her belly.

His hands move up her sides until he grabs her face, pulling her closer towards him until his nose brushes against hers. “You want me to take your virginity?” he whispers darkly, his breath fanning over her face.

“Y-yes,” she whispers back, her heart beating harder.

“You want my cock in your cunt?”

She flinches at his words, but nods into his hands.

“Say it...”

She swallows, breathing loudly through her nose. “I... I want your... your cock... in my... my c-cunt,” she stammers, feeling the blush spreading all over her body, her eyes watering under the intensity of his gaze, his closeness, his grip on her face, the dominance in his voice.

He smiles, quickly pressing his lips to hers. “Good girl.”

She closes her eyes, a deep shudder rushing through her body like a wave of relief. He pulls her against him, wrapping both arms around her, just holding her while she rests her cheek on his shoulder, savoring his warmth, the unexpected intimacy of a simple hug. But simple doesn't seem to be something he likes, because his hands wander lower, cupping her rear, fingers kneading her soft flesh, teasing between her cheeks, rubbing along the thin strip of fabric, pressing against the base of the plug.

Forcing herself not to flinch, she just leans against him and lets him touch her, her hands squished between their bodies, dangerously close to the warm hardness between his legs. With how he handles her butt, she's forced closer against him, her fingers brushing along the bulge, and when he suddenly pulls on the plug, she jerks away and into him, pelvis slamming into his lower stomach, and she can feel him through the thin fabric of her thong. Hard and hot.

His hands move back to her hips, pulling her away again. He looks at her, curiously with a dark glint in his eyes. “Have you ever touched a cock, darling?” he asks quietly.

She licks her lips, shakes her head.

“Seen one?”

Another shake of her head. His amusement turns into surprise, while the shame of her confession makes her blush even more. He gives her a strangely sweet smile, one hand on her warm cheek, thumb tracing the outline of her lips.

“Do you want to?”

“Yes,” she replies, her heart racing. His eyebrows rise up, and she quickly adds: “Sir?” He just looks at her, pointedly, demanding. “I... I want to touch it...” she then whispers, biting her lip. “Your... your cock...”

He caresses her cheek, smiling. “Such a quick learner,” he praises. “Well, go on then, make your wish come true,” he continues, leaning into the cushions, pushing her backwards a little, his arms resting on the back of the couch as he watches her intently.

She stares at him for a moment before she understands the command. Shifting on his lap, her fingers move towards his belt, shaking uncontrollably, her mind reeling, heart beating out of her chest. Somehow she manages to unbuckle his belt and open the button and zipper of his pants. Without too much thought, her hand curls into the opening, fingertips brushing against warm skin.

Looking up for confirmation, she sees him nodding, and when she frees his hard erection (the sight more intimidating than she expected) by pulling the fabric down, his lips curl up into a smirk. “Don't be shy, just grab it.”

She does, two small hands around his girthy length, his flesh hot and hard, veins bulging against her palms. A little throbbing motion from deep within. Unsure what to do, she just squeezes her hands around him a little, until he puts his big hand on hers and starts moving it, showing her how he wants her to touch him. He's surprisingly patient with his teachings, guides one of her hands up and down his shaft while he places her other to cup around his testicles.

Her breaths are frantic little puffs of air, her cheeks are burning in embarrassment, but when she looks at his face instead of his angrily throbbing cock, she sees him smiling at her, a soft expression she hasn't expected, almost proud, and she inhales deeply and focuses on the task at hand – literally.

Eventually he takes his hands away and lets her do her thing, and she follows the movements he's shown her, moving her hand up and down, shifting the soft skin over his hardened core, closing her fist around his tip, smearing the precum leaking from it around his length, while the fingers of her other hand knead the soft flesh of his balls. It's almost relaxing, meditative.

He's breathing deeper, louder, and she can see his face tensing up, as if he's holding himself back. She continues stroking him, pumping him with all she has, until he grabs her wrist and stops her, his eyes almost black from how dilated his pupils are. She's too stunned to fight him when he suddenly manhandles her onto the couch next to him, on her knees, facing him, and he forces her head down with an iron grip to her hair. She yelps in surprise.

“Open your mouth,” he rasps, voice deep and rough. She swallows hard, stares down at his cock twitching inches away from her face. But she follows the order, her lips trembling as she parts them, tongue out flat, and before she can prepare herself, he's forced her head down on him. His tip slips into her mouth, warm and wet, a slightly bitter taste on her tongue. “Close your lips around it and suck,” he orders, his grip unrelenting.

She feels her eyes watering, her chest heaving in panic, her hands bracing around his thigh. He holds her in place, waits for her to do so, and when she hollows her cheeks, he inhales sharply. She breathes loudly through her nose, feeling his cock hard and heavy against her tongue, poking into her gums. It's just the tip, but it fills out her mouth to the point she's afraid to choke on it.

“Keep... pumping,” he breathes, hoarsely, on the verge of losing it. Her hand finds the rest of his dick, and she starts moving it up and down his length, still so much ground to cover, so big she's somehow glad he doesn't force it deeper, or even down her throat.

His body is shivering beneath her, the hand in her hair tightening its grip until it hurts. Muffled whimpers escape her, but she keeps sucking on his tip, precum and saliva filling her mouth, dripping past her lips and down her chin. She moves her tongue as best as she can, flicking it around his spongy crown, while stroking up and down his throbbing girth quick and hard.

A grunt escapes him, and she feels him twitching inside her mouth and against her palm. He grabs her head with both hands and holds it down, it's a sharp pain that makes tears roll over her cheeks, but it's nothing compared to the sudden jerk against the back of her throat that makes her flinch in panic.

She tastes it, hot and salty and thick, as he comes inside her mouth, spurt after spurt, filling her cheeks until she can't hold it anymore and has to swallow. It hurts to do so, and she opens her jaw a little wider, letting most of it drip down her chin as she gulps for air.

He relaxes beneath her, his grip easing on her head, releasing her. His hand pries her tight fingers off his cock and holds it himself while he pulls her back a little. She looks up at him from under her clumped lashes, vision blurry, mouth and chin covered in a thick layer of spit and cum. She feels too lightheaded to be embarrassed about how she may look, and when he gives her a weak smile, she cares even less.

His finger traces along her chin, gathers his cum and slowly pushes between her trembling lips. It's almost an instinct to lick around his fingertip, and his eyes darken at the sight in front of him. He keeps cleaning her and she keeps licking up his essence, the taste growing on her despite the initial bitterness. He wipes his palm over her mouth, smearing the last remnants over her lips, before he holds out his hand to her, soiled palm up, watching her closely.

She shifts on her knees, her body shivering, overwhelmed by all these new experiences, but she manages to cradle his big hand with her smaller ones and leans down to trace her tongue over his lifelines, lapping up the rest until his hand is clean. He nods approvingly and grabs her chin to guide her back to his crotch. “Clean,” he says quietly, and she only nods and bends down to bring her tongue to his cock once more.

His fingers dig into her hair, gentle caresses this time, light scalp massages, while she licks around his tip, sucks up the last drops of cum from his slit, moves up and down his shaft with her lips sucking lightly, while her lungs burn and her head throbs. It's as if it's the only thing that exists anymore, his cock, his pleasure, his contentment. Only to get the soft touches and gentle words, those two words he has yet to say to her for her service, her obedience.

He pulls her back once she's done, quickly putting himself away again while she leans on her knees, head bowed, licking her lips, swaying slightly as if drunk. It's a strange kind of serenity. Calm, head empty, his taste lingering on her tongue. Nothing more to worry about.

Shifting beside her, he pulls her onto his lap, strong arms caging her in, her head resting on his shoulder as he holds her, one hand rubbing up and down her back. “You did good,” he whispers, and she shivers, soaking up the praise like a sponge, saving it for later.

“Thank you,” she breathes against him, and the hand on her back pauses.

“What are you thanking me for?” he asks.

She swallows, inhaling deeply. “For... for saying that I did good, for... teaching me, for...” She feels her cheeks burning up, head clearing enough to feel embarrassed again. “For... letting me touch and... and taste you...” she adds in a low mumble, burying her face in his collarbone. For not forcing me to do more, she thinks.

He laughs softly, resuming the rubbing of her back. “It's nice to start the day like this, huh?”

She only hums in response, melting into his body as he holds her. They sit like this for a long moment, it feels strangely natural, intimate and warm. Something she could get used to. Something that scratches the itch deep within.

ONE 🟥 TWO 🟥 THREE

End notes: It's only going downhill from here...

By the way, you may or may not have noticed that these characters don't have names: and that's on purpose. I want to keep this as vague as possible, focusing solely on their connection. If you need to address them, I guess Sir and Darling would work? But really, it's just He and She now.

(And if you wanted to, you can imagine them being your favorite fictional characters also. I didn't describe their appearance either, despite it being an older, taller man and younger, shorter woman. Anything goes.)

And yes, our female character is very naive, very submissive, very innocent indeed. I hope it's not too much. She has a crush, okay? And we all know (hopefully) how that can turn brains into mush.

Thank you for reading! Next chapter on Monday!

AO3 / / / MASTERLIST

CHAPTER / / / ONE◾️TWO◾️THREE◾️FOUR◾️FIVE SIX◾️SEVEN◾️EIGHT◾️NINE◾️TEN◾ELEVEN

[babyboywinchester]

Pls pls pls share more of your thoughts on younger Sam with Endverse!Dean

He would fuck him so nasty on the daily. He would worship the ground Sam walked on because he knows what it’s like to live in a world without his brother… so he’d keep Sam locked up, but treat him like a princess, no one else would be allowed to even speak to Sam without a bullet going through their brain… so everyone in camp knows about Sam, but no one, unless they’ve made the mistake and ended up dead, have actually seen him. That’s just how much Dean keeps him under lock and key.

It becomes sort of a myth or legend… like does Sam actually exist in there? Or has Dean gone fucking nuts? So the few who have made the unfortunate mistake of peeking through windows and catching a glimpse usually end up with the barrel of a gun pressed against the back of their dome and their brains get splattered out the other side before they can even shit themselves.

[smaeemo]

It’s crazy to see how people interpret dean and sam’s brother dynamic as “wincest”

Some people have clearly never had a parentified older sibling. Then you take into account the degree of trauma that they have been through and continue to go through. Their codependency stems from their childhood and current traumas, their mental states due to that, the way they grew up with their father obsessing over the importance of “family is everything,” and the deep parentification of Dean, AKA Dean having to be a CHILD while raising his little brother, and taking care of his insane father. It’s not “wincest”/incestuous in anyway, it’s called trauma, parentification and general unstable family dynamics.

I think that a lot of “wincest” shippers don’t actually see what trauma can do to a person and their dynamics, specifically the people that endured that trauma with you. Dean, who was the older one that had to in HIS WORDS “be the mother, father, and brother” of his younger brother since the age of !4! is obviously going to be extremely protective/codependant of/with Sam, both because of the parentification and the words of his father carved into his very being. As for Sam, having Dean be all those things for him, means that more than anything, Dean is it for him because Dean RAISED HIM. Which is why, for so many reasons, what John said to Dean (killing Sam), was one of the most cruel things he could have done. John if not straight out, on some level knows that Dean and Sam will forever have a different dynamic because Dean raised Sam, ergo, Dean being more of a Parent to Sam than he ever was.

That’s not to say I think Dean was a “perfect parent” to Sam when he was raising him. No one can be “perfect” especially not a teenager raising his baby brother. What it means is that Dean had to sacrifice his childhood and grow up quickly for Sam to be not only Alive, but also so that Sam could -have- a childhood. All of this while Dean was still actively growing up, enduring his father, hunting, and having to come to terms with monsters. But he couldn’t allow himself to mess up, and going back to the idea of “perfect parenting” we see that no, he in fact was never “perfect” specifically when he leaves so that he can play games, and he sees that Sam’s safety is (extremely unfairly) placed on his shoulders. All of this, yet again along side with never having a stable home, having an unreliable source of income, and having to basically learn how to be an adult at 7, was the start of their dynamic.

As for Sam, we see that he got to play on soccer teams, go to school, and exist (while still having to endure all of the nightmares that is his homelife) outside of the hunting. Whereas Dean was the one who gave him this chance. This is not to say that Sam should ever feel guilt over this, or that Dean needed to do this. This is to show just how different their sibling relationship is, due to the trauma.

Dean treats Sam like a brother many times, but underneath it (or on top) you will always see that he is a parent to him more than anything.

“Wincest” is talking about their “strange/codependant relationship” in a romantic or purely sexual manner. This in itself just shows how many people don’t understand what it means to either have a kid or be a parentified older sibling. (I personally am not a parentified older sibling, but my sister who practically raised me is) and because of MY family dynamic I can speak from experience (definitely not to Dean and Sam’s extent) of having a parentified older sibling, and how that differs from regular sibling relationships.

Ok, this was a ramble, but as a whole “wincest” is extremely disturbing to me as a whole. And I don’t know what the rules are on this specific topic, so Idk how much I should say. But I definitely don’t condone inc*st to any degree, but to each their own ig.

Alright, I have SO much more to say on this topic. But I will hold back for now, just because I am sleepy.

XOXO