#sub dean

He watches you move with a calm confidence and his pussy actually pulses. Every time you walk into a room, the air feels thicker, and he can feel that familiar, humiliating heat pooling between his legs, his pussy getting ridiculously wet from just the sight of you.

During hunts, you offer brief commendations with a hand on his shoulder or a simple good work on that trap that sends jolts of electricity straight down his spine. You drink heavily and smoke long into the night, but unlike John, you carry your strength with a lazy grace that never turns into anger. Seeing you laugh with Bobby makes him crave the heated stability.

Sometimes, Dean finds himself staring, unable to look away from the way your jeans, staring against the heavy, unmistakable bulge of your cock, a silent promise of the size he knows he needs.

The darkness of the room was suffocating, thick with the scent of old wood and Dean’s own frantic arousal. He lay sprawled on the mattress, his body trembling with a need so sharp it felt like a physical wound. His fingers were slick, sliding deep into his needy pussy with a desperate friction, while his other hand slapped hard against his own jaw, trying to sting himself into silence.

“Fuck — please — ” he mewled a tiny sound, before swallowing it back.

Every time a quiet, broken moan escaped his lips, he froze, heart hammering against his ribs — absolutely terrified that Sam or Bobby would hear the sound of him unravelling late at night.

Then, the fantasy took over, pulling him under like a tide. Suddenly, he wasn’t alone. The scent of leather and stale smoke overwhelmed his scenes, while all he felt was the unyielding weight of you crushing him into the cushions. His legs were shoved wide and his back curved as you hovered over him.

“That’s it, Dean,” your voice rumbled in his ear, low and commanding. “Take it all. You’re so fucking greedy for it, aren’t ya?”

Then, the phantom sensation of your cock hit him thick, hot, and unyielding, driving straight into his messy, overstimulated pussy. He let out a choked sob real-time, his hips jerking upwards to meet the imagined thrusts.

“God, you’re so wet f’me,” you murmured, voice a rough vibration against his skin. “Wrap those legs around me, take it all, Dean — show me how much you want it —”

His fantasy seemed to reach its peak in tempo, followed by a white-hot sensation that sent Dean over the edge.

Back straining off the sheets, he buckled hard as he orgasms — a silent, shaking mess in the dark. He buried his face into the pillow to muffle the desperate, broken cries of your name, his heart was a frantic patter against his ribs.

“Fuck — you're —,” he gasped with a trembling whisper as he lay there in the cooling dark, trembling and spent from the illusory feeling of your weight. That soothing voice was still echoing in his mind, leaving him more desperate for the real thing than he’d ever been in his entire life.

Minutes later, Dean stumbled towards the bathroom, his legs feeling like jelly and his skin still flushed from the friction. He cleaned himself up with the cool water doing little to dampen the remaining pleasurable sensation of you. He felt wrecked, a shivering version of himself, desperately trying to pull his composure back together before the sun came up.

Thirsty and feeling the post orgasmic ache in his core, he crept down towards the kitchen, hoping to grab a glass of water without making a sound. But as he rounded the corner, the sight of you stopped him dead in his tracks.

You were sitting on the couch, a half finished whiskey in your hand, a stack of lore books spread out on the coffee table in front of you. The low light of the lamp casting long shadows across your face, making you look even more formidable, even more grounded.

“Can’t sleep?”

The question came in that same coarse rumble that had been haunting his dreams only minutes before. Dean felt his knees actually weaken — a traitorous heat instantly blooming at his clit as if he hadn’t just finished coming to the thought of you. He had to physically grip the doorframe to keep from swaying.

“Nah,” he managed, forcing his voice to stay steady, though it came out a fraction higher than usual. He plastered on his best ‘tough guy’ nonchalance, leaning against the wall with a practise ease that felt entirely fake, “Just… thirsty. Brain won’t shut up, ya know?”

He kept his eyes averted, terrified that if he looked at you too long, he’d lose his fucking mind. But, he could feel the heat of your gaze on him, a heavy masculine weight that made his skin prickle. He focused intensely on a random spot on the floor.

“I hear that,” you replied before taking a slow sip of your drink, the movement effortless. “Sometimes the world’s too loud, even when it’s quiet.”

Dean nodded, a very jerky and unconvincing movement. “Yeah, tell me about it.”

He finally risked a singular glance at you, and his heart nearly stopped. You were looking at him, your expression unreadable, but your eyes sharp. It’s as if you could see right through his ‘tough guy’ facade and straight into the trembling mess.

You set the whiskey down, your gaze softening with a genuine, steady warmth that only makes his heart hammer harder. “What’s going on, Dean?” you ask, voice dropping into a comforting register. “You know you can talk to me about anything, sport. Whatever’s on your mind — I’ll help.”

Sport.

The term of casual, masculine endearment hits him like a physical blow, that makes his pussy throb with a sudden, shameful ache.

How the fuck am I supposed to tell you that?

He wants to scream it. He wants to grab the front of your shirt, pull your frame down until your lips are inches from his and tell you that the only thing keeping him sane is the desperate, pulsing need to feel you inside him. He doesn’t want you to just be a listening ear; he wants you to act on your words firmly too.

Ugh, fuck.

He needs your calloused hands pinning his wrists or your thick fingers stretching him wide till he sobs — or better yet, your heavy cock driving into his weeping pussy till his brain’s fucking empty. The ache is getting unbearable by each grovelling minute. It’s a heavy, wet throb that him want to sink to his knees right there on the kitchen linoleum. He needs the pressure, the weight, the stable masculinity. 

He needs you to stop being his “mentor” and start being the person who ruins him.

“Just… thinking about the case,” Dean lies, the words feeling like ash in his mouth. He forces a lopsided, cocky grin — the kind he’s used a thousand times to hide the fact that he’s falling apart.

Unfortunately his eyes betray him. Pining green lingers a second too long on the way your throat moves when you swallow or the way your large hands were splayed upon the case studies.

“The case can wait ‘til morning, Dean. You look like you’re wound tighter than a guitar string.” You chuckle while gesturing to the empty spot on the couch beside you, “Sit, drink your water — you’re pacing like a caged animal.”

Dean hesitates, his heart performing a frantic drumroll against his ribs. He should go back to his room, back to the safety of his blankets and his lonely aching silence. 

But the pull of your presence is too fucking strong.

With stiff movements, he moves towards the couch, trying to mask the way his thighs rub together with every step. He sinks into the cushion beside you, careful to leave a respectful distance — though every instinct in his body is screaming at him to close the gap.

“Yeah, well, the Winchester brain never really shuts off right?” he says, as he takes some heavy sips of his water.

As he drinks, he can’t help — he really can’t help — but steal a glance at you.

Composed and steady, you’re leaning back with the lamp light catching the rugged lines of your face. You look so damn comfortable, so entirely in control of yourself, while he feels like he’s one second away from shattering.

The silence between you stretches thick with everything he isn’t saying. He sets the glass down, his knuckles white as he grips the cushion’s edge. He’s trying to play it cool, trying to be the legendary hunter, but the heat radiating from your body is making it impossible to focus on anything but the proximity of your thigh to his.

“You’re a terrible liar, Dean,” you say softly, not even looking up from your book, though the corner of your mouth twitches with a knowing smirk.

He stiffens, a flush creeping up his neck. “Yeah? And since when did you become an expert on me?”

“Since you started looking at me like you’re starving — and I haven’t even fed you yet?”

The sheer audacity of the comment leaves him breathless. Dean opens his mouth to snap back a witty retort, but the words die in his throat. 

You don’t even look up from the page as you reach out, your large hand landing on his thigh. You don’t move it far, but the stable heat was enough to make his breath hitch. His reaction is instinctive. His legs don’t move nor straddle; they widen, his knees falling open in a silent, desperate invitation that he can’t control.

Then, your hand shifts. Your fingers slide downwards, moving with a terrifying, calm precision.

Because he was so frantic to get back to bed, he hadn't even pulled his boxers back up, leaving himself completely exposed to the cool air and your sudden touch.

Your digits find the wet heat of his bare pussy, grazing a stripe of his labia, your blunt fingertips catching on the sensitive flesh. Dean lets out a strangled, high pitched gasp, his entire body jolting as if he’d been struck by lightning. He tries to pull his legs back together — to hide the evidence of his shame — but your hand is a heavy anchor, holding him wide and vulnerable.

You finally shift your gaze from the book, your eyes dark and knowing as they land on his flushed, trembling face. You don't pull your hand away; instead, you press a little deeper, your finger curling slightly into his wetness.

"You're soaking," you murmur, your voice a low, dangerous rumble that vibrates right through him. A smirk tugs at the corner of your mouth. "Naughty boy, been watching some porn late at night?"

"I — it's not — " Dean stammers, his cocky facade completely demolished. He's staring at you, his eyes wide and glazed with terror and lust. He looks like a man caught red-handed, his chest heaving as he tries to find a lie that doesn't sound pathetic.

"It's not — it's not like that," he breathes, though the way his hips instinctively tilt toward your hand tells a completely different story.

You let out a low chuckle, finally closing the book and setting it aside. You increase the pressure, your thumb beginning to grind slow, heavy circles against his clit, catching on the wetness he's been producing all night.

"Then what is it, Dean?" you demand, your voice dropping an octave, becoming that commanding tone that makes his insides melt. "Because you're dripping all over my hand, and you're shaking like you're waiting for me to do something about it?"

Dean can't even find the breath to argue. His head falls back against the couch cushion, his eyes fluttering shut as he lets out a broken, needy whine. The sensation of your thumb grinding against his clit is too much; it’s the exact friction he’d been trying to mimic with his own fingers in the dark, but your hand is larger, heavier, and infinitely more authoritative.

"Please —" he whimpers, the word slipping out before he can censor it. He doesn't even know what he's asking for. More pressure? More fingers, or the real thing he just knows the ache in his pussy is screaming for relief?

You lean in closer, your shadow swallowing him whole. The scent of your skin, mixed with the faint aroma of alcohol and tobacco, wraps around him like a physical weight. 

"Please what, Dean?" you murmur against the shell of his ear, your warm breath hot against his skin. "You want me to stop — or do you want me to show you exactly what you were dreaming about?"

Dean's eyes snap open, glazed and unfocused, as he lets out a shuddering breath. He can't even lie anymore; the truth is written in the way his hips buck weakly against your hand, seeking more of that brutal, grounding pressure.

"Don't stop," he chokes out, his voice a mere thread of sound, stripped of all its usual bravado. "Please —  don't stop."

You grin, a slow, predatory curve of your lips, as you slide a second finger deep into his tight, pulsing heat. The sudden fullness makes him cry out, a sharp, needy sound that echoes in the quiet kitchen, but you don't let him recover. You start to move, your fingers working with a rhythmic pace that drives him straight back toward the breadth of you.

You haul him up effortlessly, dragging his body until he's straddling your massive thigh, his back pressed flush against your chest. Your left hand fists in his hair before sliding down to grip his jaw, tilting his face at a sharp angle. You press your lips to his in a bruising, demanding kiss, then abruptly yank his head to the side, holding him there so he can feel your breath against his ear.

"Look at you," you murmur, your voice a controlled, gravelly purr. "You're fucking soaking, Dean. Every time I move my fingers, you squelch. Tell me truthfully, have you been touching yourself like this all night?”

Dean swallows hard, his throat working against your grip. "No," he gasps out, the lie tasting bitter even as his hips betray him by grinding harder against your palm. "Just, some lousy porn — nothing else."

You don't call him out immediately. Instead, you let the silence stretch, the only sound is the wet slap of your fingers working inside him.

In the corner of the room, Dean's eyes catch your reflection in the dusty mirror. The sight of himself completely exposed, helpless, and being handled like a toy sends a fresh wave of shame and arousal crashing through him. He knows he's lying; he knows you can see every tremor in his body. But he can't stop looking.

His gaze drops down the mirror's reflection, trailing past your broad shoulder to where your hand is buried between his thighs. He watches as your fingers disappear into his slick folds, working with a ruthless efficiency that makes his vision blur.

In the mirror, he sees your thumb hook under the sensitive edge of his flesh, pulling his labia wide to expose the raw, swollen pink of his entrance.

"Look at that," you murmur against his ear, your breath hot enough to scald. "Look how fucking open you are for me. Look at how you're begging for it."

Dean's breath hitches as he stares at the reflection. Seeing it from the outside — seeing how your thick fingers stretch him apart — how his own pussy glistens and pulses around your knuckles makes the reality of his degradation hit him like a freight train.

"Fuck," he chokes out, his forehead dropping against your shoulder as his hips buck involuntarily. "Fuck, please — please!"

"Shhh, easy now, Dean," you coo, your voice dripping with that infuriatingly calm, patronising affection. You sound less like a lover and more like someone soothing a needy puppy — which only makes his blood boil and his pussy clench tighter. "There we go. Just let it happen, don't fight it."

You pick up the pace, your fingers working with a cruel, precise rhythm that targets every nerve ending he has. Dean's hips buck violently against your thigh, his back arching until his spine cracks audibly.

A wrecked, high pitched keen tears from his throat as his orgasm hits sudden and overwhelming. His body shudders uncontrollably as he spills over your fingers, his vision swimming behind closed eyelids.

But you don't slow down. You don't let him collapse into the afterglow. The moment his tremors begin to subside, you immediately resume the punishing stroke.

Dean gasps, his eyes snapping open in genuine shock.

"Wait fuck no, I can't — " His voice breaks as he glances back at you over his shoulder, his expression one of pure bewilderment.

His brain is short circuiting; he knows he's already come multiple times tonight, alone in his bed, exhausted and desperate. His body should be spent, his nerves fried, but the way you're touching him the overwhelming authority of your hand is forcing new waves of arousal through him that shouldn't exist.

"What's wrong, champ?" you murmur, your thumb finding that sensitive spot again with unerring accuracy. You tighten your grip on his jaw, forcing him to meet your amused gaze. "Already spent? After all that lying?"

"I'm — I'm already —" he stammers, his hips jerking involuntarily as your thumb finds that perfect, swollen nerve again. "I can't — I'm already fucking empty, I swear to God — "

"Empty?" you interrupt, your chuckle dangerously as you lean closer, your lips brushing against his ear. "You don't know shit about being empty, Dean. You're just sensitive. Your body is still screaming for more."

You increase the pressure, your fingers sliding deeper, stretching him wider with each thrust. You're working him open, your blunt fingertips slick with his arousal as you relentlessly massage the walls of his pussy.

"If you want the real thing tonight, you need to be ready for it," you murmur, your voice dropping into something darker, more utilitarian. "You need to be loose — you need to be fucking dripping so I can slide right in without tearing you apart. Consider this an investment."

Dean's head lolls back against your shoulder, his breathing coming in shallow, confused pants. "An investment? What the fuck are you — "

His words die in his throat when he shifts slightly, his ass grinding against your thigh.

In that movement, he feels it: the unmistakable, rock hard ridge of your cock pressing through the denim of your jeans, poking insistently against the sensitive cleft of his ass. The heat of it radiates through his clothes, a promise of something far more devastating than your fingers.

The realisation hits him like a physical blow. You weren't just tormenting him for sport, nor were you being cruel. You were prepping him. Every punishing stroke, every forced climax, every stretch of his labia had been calculated to make his body surrender completely to what was coming next.

"Oh," he breathes, the syllable more of a whimper than a confession. His clit throbs painfully, slick with the evidence of his own undoing, while the hard bulge behind him promises a different kind of fullness entirely.

"Oh," he repeats, his eyes blown wide as they fix on your reflection in the mirror, seeing the way your erection strains against your jeans right where his ass meets your thigh. "Oh god," he chokes out, his hips stuttering in a helpless attempt to both escape and press closer.

"I'll pull one or two more orgasms out of you, Dean," you state plainly, your tone as matter of fact as if you were discussing the weather. "Maybe three, if you're as good as I think you are."

"No — fuck you, I can't — " Dean protests, his voice cracking as he tries to twist away from your relentless fingers. But there's nowhere to go.

Your body is a wall behind him, and your hand on his jaw is an iron vise that keeps him exactly where you want him. He can only squirm, his hips bucking uselessly against your thigh in a desperate, futile attempt to regain some semblance of control.

Smack!

The sound of your palm connecting with his jaw is sharp and startling in the quiet room. It isn't enough to hurt him, but it's firm enough to shock the protest right out of his lungs.

You hold his face steady, forcing him to meet your gaze. "Listen to me, Dean. What you see in those stupid fucking porn videos — that's all bullshit. Real sex requires preparation — and I'm the one teaching you how to actually handle it. You need to learn how to take this."

You lean in closer, your lips grazing his earlobe while your fingers work deeper, stretching his slick walls with increasing urgency. "Now, you're going to be a good boy and accept this. Say it, say you'll take whatever I give you."

"I — I won't —" Dean starts to protest, but you tighten your grip on his jaw, applying just enough pressure to remind him who holds the power here.

"Wrong answer," you command, your voice dropping to that stern register that leaves no room for argument. "I want to hear you say it properly, through every one of those pathetic little gasps."

Dean's body betrays him completely. His hips roll forward in a desperate, involuntary search for friction as your fingers stretch him to his limit. A broken, strangled noise escapes his throat as he finally surrenders to the authority in your voice.

"I'll — fuck — I'll take it," he manages to choke out, his words punctuated by sharp, hitched gasps that leave him panting. "I'll take — whatever you give me."

"Good boy," you murmur, the praise dripping with that same patronising satisfaction. You give his jaw one last firm squeeze before releasing him, though you don't pull away.

Instead, you let your hand slide down from his face to rest heavily on his chest, feeling the frantic, rabbit quick hammering of his heart beneath his ribs.

"See?" you whisper, your breath hot against his neck. "That wasn't so hard, was it? Now we know you're listening."

The room falls into a heavy, charged silence, broken only by the ragged sound of Dean's breathing. His body has finally gone boneless against you, his muscles twitching with the aftershocks of the orgasm you forced out of him. He drips freely, sending warm rivulets of cum down your thigh.

You withdraw your fingers slowly, the wet sound of your exit making him whimper. Without hesitation, you take those slick, swollen fingers and press them against his mouth. 

He doesn't resist, leaning into the touch, his eyes rolling back as he begins to suckle on your fingers — tasting the salty, unmistakable evidence of himself. He heaves against your chest, his mouth working around your knuckles with a desperate, unconscious hunger, seeking comfort in the very thing that just broke him.

While he is momentarily occupied, lost in that haze of shame and sensory overload, you give him a moment to catch his breath against your shoulder. Your fingers slip free from his mouth, leaving him panting and dazed, but you don't release your hold on his waist. You keep him pinned against you, anchoring him while you shift to the next phase of your plan.

With one hand still possessively wrapped around his middle, you reach down with the other. Your movements are efficient, practiced, and utterly calm as you unbuckle your belt with a metallic click that sounds deafening in the quiet room.

You work the zipper down, and then, with a gradual motion, you free your aching cock from your jeans.

Dean's breath hitches audibly as he feels the sudden change in temperature and weight beneath him. He shifts his hips slightly, and his eyes go wide as he sees the thick size of you lying just beneath his thighs.

The heat coming off your cock is staggering, a physical force that makes his entire lower body tremble. His gaze drops to where your cock presses against his swollen pussy, already wet with the mess of his own orgasms.

"Oh god —" he murmurs, his voice barely a thread of sound, thick with awe and terror. "It's so —  it's so big —"

He can feel the sheer girth of you spreading his folds apart even before you make contact. He's terrified of how much he wants it, terrified of how perfectly his body seems to be reaching for you despite the exhaustion still clinging to his limbs.

As you prepare to make your move, your hand dips into your pocket. The crinkle of plastic fills the space between you as you tear open a sachet.

Dean catches the sound, his eyes darting to the packet in your hand. A weak, self deprecating laugh escapes his lips — a pathetic attempt to reclaim some dignity through humor.

"You — you always carry lube around with you?" he manages to wheeze out, trying to sound teasing when his voice is clearly trembling.

"I was going to go out to the bar tonight," you reply, your tone casual, and utterly unbothered by his attempt at levity. "But then I heard your pretty little whines coming down the hallway." You let out a dark chuckle at the way his face instantly floods with a deep, mortified crimson. "Figured I'd come see what all the noise was about instead."

The implication hangs heavy in the air between you.

You begin to lather the sweet scented slick over your cock, the clear gel catching the dim light as you coat yourself from base to tip. Then, with deliberate slowness, you smear the rest over his dripping labia, ensuring every inch of his entrance is glistening and ready.

Even after the work you've put in, you can feel the resistance beneath your touch; despite the lube and his arousal, his body is still coiled tight.

"Your walls are quite thin, Dean," you murmur, watching how his pupils dilate at the implication.

His heart hammers against your chest. The realisation that you've been listening to him every desperate moan, every wet slap of his own hand against his thighs every single night since you arrived here threatens to overwhelm him. But there is no room for shame now.

His entire universe has shrunk down to the point of contact between his pussy and the massive heat between your cock and his pussy. He's too far gone, too consumed by the physical presence of you to even process the humiliation of being caught.

So, he gives a tentative, desperate grind, his hips rolling against your cock in a silent plea for friction.

You glance down at the sight of him in your lap, watching how his hips stutter against you. His desperate self is thinking exactly the right way. You can see it in the way he arches, seeking that contact, begging for the fullness he knows is coming. Good. You'll let him have this — you'll let him work for it, getting a job out of him first, letting him ride that slick heat until he's begging for mercy.

But you aren't planning on being gentle when you finally decide to fuck him mean. You've spent the last hour preparing him, stretching him, and breaking his resistance, all so you can fuck him without hesitation.

"Slow down, Dean. I told you we're still prepping."

You grip his hips with bruising force, your fingers digging into the soft flesh above his pelvic bones to anchor him. However, you don't let him sink down. You simply hold him just at the threshold, forcing him to hover there, suspended between desperate need and the agonising promise of fullness.

"But please — " Dean gasps, his voice breaking as he tries to push downward, his hips stuttering in an involuntary attempt to impale himself on your cock. "I need — I need you inside — fuck, please."

"I said slow," you growl, your voice dropping into that stern tone that brooks no argument. "You're still too tight. If I push you now, you'll tear, and I'm not interested in hearing you scream from pain instead of pleasure."

It's a lie, and his younger, desperate mind knows exactly what you're doing, but he's too far gone to care about the deception. He can feel the truth in the way your cock pulses against his pussy, teasing the very edge of his folds without giving him the release he's starving for.

"I'm not fucking you yet," you murmur, your breath hot against the nape of his neck as you begin to move him. "We're going to work this friction until you're completely slick, until you're begging me to ruin you."

Instead of pushing inside, you begin to guide his hips in a slow, punishing grind. You force him to slide his pussy along the entire length of your cock, but only on the outside.

You make sure his clit catches repeatedly against the sensitive ridge of you, the friction sending sparks of electricity straight to his brain. The wet, squelching sound of your cock sliding between his labia fills the room as fills the space between your bodies.

Every time he grinds down, you make sure he feels the full, unforgiving texture of your cock sliding between, never letting him slip past the entrance

You keep him exactly where you want him: hovering on the precipice of ecstasy, his pussy’s stretched taut and glistening with lube as it rubs relentlessly against you.

"Please, please, please —" Dean whines, his head tossing back against your shoulder as his hips stutter in a desperate rhythm. "It's — it's too much, I can't — "

"You can, and you will," you cut him off, your grip tightening on his hips to control the pace. "Feel that? That's what happens when you don't know how to prepare yourself properly."

You deliberately angle your cock so that each downward roll of his hips forces his clit to scrape directly against the edge beneath your cock's head. 

"Please — fuck, please just fuck me already," Dean sobs, his voice breaking into something raw and pathetic. His hips are working in frantic, uncoordinated jerks, trying to force his way down, but your hands are like iron shackles around his pelvic bones.

You move him with effortless, terrifying strength, sliding his pussy up and down your cock as if he weighs nothing at all, controlling every millimetre of friction.

"Shhh, easy, sport. Don't get ahead of yourself," you coo, pressing tender kisses to his sweat slicked temples.

You sound like a guardian angel soothing a frightened soul, but internally, you're scoffing at how goddamn easy this is. His body is responding to every single movement with desperate, unguarded need; his pussy is practically begging for the invasion, slick and pliant under your expert torment.

"I can't — I'm gonna — " he gasps, his entire body trembling as he teeters on the razor's edge of another orgasm, his breath coming in short, broken whimpers. His hips stutter helplessly against you, his pussy already raw from the relentless grinding — each movement sending fresh waves of overstimulation through his already fried nerves.

"I'm gonna fuck, I'm gonna cum —"

"Not yet," you murmur against his ear, your voice dripping with mock concern. You maintain that torturous rhythm for three more agonising seconds, pushing him to the absolute brink where his vision blurs and his muscles lock up, before suddenly stopping.

You pull back just enough to feel the cool air hit his slick skin, then you give his ass a cheerful, affectionate pat. "Okay, now you're ready."

Before he can even process the sudden absence of friction, you manhandle him. With practiced ease, you flip him over on the couch, pressing his chest down into the cushions while forcing his hips high into the air. You plant yourself behind him, your knees bracketing his thighs as you spread his ass wide with both hands.

The sight is perfect — his pussy all flushed a deep shade, glistening with lube and his own releases, stretched open and waiting.

"There we go," you murmur, the tenderness gone from your voice, replaced by something hungry and predatory. "Now we can actually begin."

You don't pound into him straight away. You don't give him the violent release he's begging for. Instead, you press the broad, blunt head of your cock against his entrance and begin to push, inch by agonising inch.

Dean's entire body jerks as he feels the intrusion. "Ah fuck! Oh god, it's — it's too — " His voice cracks as he realises you aren't rushing. You're taking your time, forcing his tight walls to accommodate your girth one excruciating inch at a time.

You reach forward, threading your fingers through his hair and yanking his head back just enough so you can watch his face. His eyes are blown wide, pupils swallowed by irises as they fix on yours, glassy with tears and overwhelmed by the sensation of being split open.

"Look at me, Dean," you command, your voice a low, dangerous purr. "See how well you take it?"

You push again, a slow, inexorable advance that forces his pussy to stretch to its absolute limit. The wet, sucking sound of your cock sliding past his tight entrance echoes in the quiet room.

Each inch feels like an eternity, each millimetre a new lesson in surrender. His walls flutter around you, clenching desperately as they try to accommodate the invading girth, but you don't give an inch of slack.

"Fuck — it's so big — you're stretching me so much " Dean whines, his fingers clawing into the couch cushions.

His breath comes in ragged, terrified gasps as you continue your methodical assault. The resistance is delicious the way his muscles spasm and fight against the intrusion before finally yielding to the overwhelming pressure.

"That's it, Dean. Take it all," you whisper, your voice devoid of any real sympathy as you drive deeper. "Every single inch."

You watch with clinical fascination as his body reacts to the fullness. The sensation of his tight pussy gripping you is intoxicating — a warm vice that threatens to undo even your own composure.

"I'm — I'm full, oh god — you're so deep — " he chokes out, his back arching involuntarily as you finally bottom out against his cervix.

The teasing is over. The performance of the gentle mentor has been discarded like yesterday's trash, replaced by something far more primal.

You shift your weight, planting your knees wider to brace yourself as you settle into a brutal, relentless position. One hand remains buried in his hair — not to soothe him this time — but to hold his head exactly where you want it tilted back. Just enough so you can watch every expression of his degradation.

"That's enough playing around, sport," you growl, your voice dropping the pretense of sweetness. It's cold now, hard as flint, the voice of someone who has stopped asking permission and started taking what belongs to them. "Time to actually fuck you properly."

Without warning, you drive forward. You don't ease in anymore; you thrust into him with powerful, piston-like paces that send his entire body bunching forwards against the couch cushions.

Each thrust is deep and utterly relentless, forcing the air from his lungs in ragged, broken cries. You're not interested in his comfort anymore; you're only interested in his capacity to endure you.

"Look at this pussy," you sneer, your free hand coming down to slap against his thigh as you drive home again. "So fucking messy. So fucking desperate." You lean down, your mouth close to his ear as you continue the brutal rhythm. "Bobby talks about you like you're some kind of legend, Dean. A grand hunter — the best there is. But right now? All I see is a needy little boy who can't even handle being filled up."

Dean can't even form coherent sentences. He just nods dumbly against the cushion, his brain short circuiting from the intensity of the penetration.

He's lost in the sensation of you stretching him apart, shattering under the onslaught. He can only manage weak, incoherent sounds that dissolve into wet whimpers every time you bottom out against him.

"Listen to those moans, Dean," you chuckle darkly, the sound vibrating against his spine as you pick up the pace, your thrusts becoming faster, more punishing. "Goddamn, they're fucking pornographic. If Sam or Bobby heard you right now, they wouldn't be able to tell the difference between you and some R-rated video — you sound exactly like what you are: a fucktoy."

The words hit him harder than the physical impact, but he has no defense.

His body betrays him with every word, his pussy clenching around your cock in desperate, involuntary spasms that only make you want to fuck him harder. You reach around, your palm connecting with the meat of his ass in a sharp, stinging spank that makes him cry out.

"Such a pretty ass, too," you drawl, your voice dripping with cruel amusement as you deliver another smack that leaves a blooming red handprint across his pale skin. "All flushed and shaking for me."

You watch with predatory satisfaction as his body arches involuntarily, his hips stuttering against your cock in a futile attempt to find some kind of rhythm amidst the chaos you're creating.

His tears have begun to spill freely now, dampening the couch cushions as he sobs through each deepening thrust, but you don't stop. If anything, the sight of his breakdown only fuels your hunger.

"God, you're gorgeous when you're breaking like this," you murmur, your grip tightening on his hair to yank his head back further, forcing him to meet your cold, hungry gaze. "So helpless — so fucking perfect."

As you drive yourself into him again, your cock sliding through the slick, messy heat of him, your free hand slides down, fingers tracing the sensitive edge where his pussy meets his ass.

You pause there for a heartbeat, the tip of your cock grinding against his inner walls while your touch lingers dangerously close to his tight, puckered hole.

"You know what I'm thinking about, Dean?" you chuckle darkly, your breath hot against his ear as you watch his hips quiver in terror. "All this mess, all this wetness — it's a shame it's only coming from one hole."

You deliver one last, devastating thrust that makes him cry out in a high, broken note, before leaning down to whisper the promise that makes his entire body freeze.

"Next time, I'm not stopping at your pussy — I'm going to open you up right here, too. I'm going to stretch that pretty little asshole until you can't even remember how to walk straight."

You watch as the threat sinks in, his entire body going rigid beneath you, every muscle locking up in terror at the prospect of what's to come. The way his breath hitches, the way his pussy clenches around you in a desperate, instinctive attempt to protect itself — it's intoxicating.

"That's it, freeze for me," you growl, feeling the delicious tightness of his internal muscles as they spasm around your cock. "Let that fear sink in. Let it make you even wetter."

You don't give him a moment to recover. You resume the mean rhythm, each thrust more punishing than the last, driving him further into the cushions.

You want him to remember this feeling — the feeling of being completely owned, completely exposed — and utterly powerless against the promise of what you'll do to him next.

The final thrusts come with an unrelenting force that leaves Dean completely undone.

His body has reached its absolute limit; his muscles have gone beyond exhaustion into a state of pure, boneless surrender. As you feel your own orgasm building your balls heavy and aching with the need to release you lean down, your voice rough and demanding.

"Should I cum inside you, Dean? Should I fill you up with everything I've got?"

He doesn't even hesitate. His mind is too fried, his body too overwhelmed to consider the consequences. He simply nods dumbly against the cushion — a pathetic, desperate movement that says he doesn't care if he gets pregnant, doesn't care about Bobby, doesn't care about anything except the relief of your cum flooding his abused insides.

"Attaboy," you growl.

With one last, bone-deep lunge, you bottom out against him, cumming in hot, thick pulses that fill him to the brim.

Dean's body convulses beneath you, a final, weak tremor running through his spine as the overwhelming sensation of being filled sends him spiraling past the point of conscious thought. His breathing becomes shallow, erratic gasps before smoothing out into the heavy, unconscious rhythm of someone who has simply given up.

"Fuck, sport," you grumble, a snarky, almost disappointed sound escaping your throat as you feel his strength drain away entirely. He's teetering on the edge of passing out, his limbs going limp as his brain shuts down to escape the sensory overload. "Look at you. Can't even stay awake for the best part."

You feel him slipping away, his forehead pressing limply against the couch cushions. You lean down, your voice dropping into that dark, possessive comfort that promises no escape. "Don't worry, you'll stay right here — I'll continue fucking my fill. After all, this is exactly what you've been craving all these weeks, isn't it?"

You watch with cruel satisfaction as his consciousness finally fractures.

Dean's body goes completely boneless, his face pressed limply into the fabric of the couch, tears still wet on his cheeks. He has passed out, his mind unable to process any more of the exquisite torment you've inflicted.

He lies there in a state of beautiful, broken surrender: face down, ass up, completely exposed to your whims.

Even as he sleeps, you aren't finished.

The rhythmic slap of flesh against flesh fills the room as you continue to claim him, your thrusts methodical and unhurried now that he can no longer fight back or beg for mercy. Poor boy. 

Maybe he should’ve thought twice before desperately chasing after the heat of someone double his age, double his intelligence, and double his lust.

Watching his tired form twitch under your touch brings a surge of dark triumph that no supernatural battle could ever match.

You think to yourself how fortunate you were that you agreed to take on Bobby's request for this particular case; it had promised danger, but it delivered something far more intoxicating. The raw power of breaking a legend, the feel of his flooded pussy clenching around you even in his stupor is undoubtedly the most exhilarating sensation you have ever experienced.

It surpasses every hunt, every demon slain, and every supernatural victory you've ever claimed. As you drive yourself home one last time, you realise that this conquest is the only reward that truly matters.

$ tag @twentytomidnight @i-gotta-go-so-much-bigger @hisokamywaifu

$ join taglist

and i totally agree with him letting a few… well, let’s just say some high noises out when he’s close. and if you asked him about it like it was regular conversation, he’d probably close up and hide in his shell immediately. he’s ashamed of it, ashamed of how he acts when he’s in bed. it’s not manly. it’s not hot. at least, dean doesn’t think it is.

you, on the other hand?

you like it.

it’s one of the hottest things he does, and that’s saying something when it comes to dean: because everything he does seems to be hot. but by far, it’s the way he sounds when he’s in bed with you. the way he lets go, the way he feels comfortable enough to truly be himself around you—it makes you feel out of this world.

it’s around the third time you guys have sex that you bring it up. you’re still navigating each other, whatever this relationship will be, but one thing remains certain: you can’t get enough of one another. you’re in bed when you build up the courage, dean still laying on top of you, basking in the aftershocks.

he was by far the loudest this night, since he didn’t have to worry about nosy neighbors or sharing the room with sam. you can tell he’s embarrassed about it. uncomfortable with the fact that you had to hear him like that. with the fact that he let his guard down, showed his true colors.

you’re the first to break the silence.

“y’know, some people might think i’m hurting you when we’re together,” you try and ease his overthinking, your hands still tracing over his bare back.

dean huffs a snort into the skin of your sternum, but it’s halfhearted. “yeah, uh. sorry ‘bout that. didn’t mean to uh. turn you off or anythin’ like that.”

oh, dean. always putting himself down. “you didn’t,” you shake your head on the pillow. if you leaned your head a little more down, your face would be in dean’s hair. “i like the noises you make.”

dean blinks. your confession makes him look up at you from where he’d been laying on your chest. “y’do?” he sounds shocked. appalled. like no one would ever like the noises he makes.

“i mean… yeah,” you sheepishly reply, looking away briefly. “well, i, y’know, wasn’t expecting that from you, but… it’s hot.”

huh. well, if you think it’s hot, maybe it’s not so bad that he does it then, dean thinks. maybe it’s not as unmanly as he thought. he absorbs your words for a moment, eyes searching your face. you’re telling the truth.

“oh,” is all dean has to say at first. “well. then, uh. guess i’ll, uh. keep doin’ that, then.” you smile at the way he’s all flustered, and not from post-sex. your hand goes to his face, cupping it—and dean pushes his head into your palm immediately.

“you shouldn’t be ashamed of that, you know,” you murmur quietly.

“yeah, well, shouldn’t and actually doin’ it are two different stories,” dean mutters back, looking down again, too. “i jus’… i can’t control it. not with you.”

“and i’m not asking you to,” you retort. “like i said. i think it’s hot.”

dean nods, his face melting at your words and your hands still tracing his face. maybe you’re right. now, this shame won’t go away entirely, but he can feel the walls starting to crack. he sighs, but not because he’s upset with you. quite the contrary.

it’s because he’s safe.

in case you missed any of my sub ! dean work, here’s literally everything i’ve ever written about him:

sub ! dean headcanons

sub ! dean cries during sex

sub ! dean somno

sub ! dean sex in the back of the impala

sub ! dean sleepy sex

sub ! dean dry humping

sub ! dean jerking off to you and you catch him

sub ! dean is into soft sex

sub ! dean (ish) with male reader

brat ! dean headcanons

the bunker was dead quiet after the hunt — except for dean winchester’s voice. he strolled in like he owned the place, green eyes glittering with mischief, boots heavy on the concrete.

“well,” he said, peeling his jacket off and tossing it aside. “somebody owes me a beer for carrying their ass today.” you didn’t look up. you were cleaning a blade.

dean leaned on the table, grin widening. “what’s the matter? can’t even thank me? pretty sure if i hadn’t been there you’d be demon chow right now.” you calmly set the blade down and looked up. “and by the way,” he went on, “maybe next time, instead of staring at my ass all hunt long, you focus on the actual monster. just a thought.”

that earned him a slow blink.

dean smirked. “what? can’t help yourself? i get it. it’s a damn good ass.”

“dean,” you said, voice low.

“yes, sir?” he shot back immediately, mocking, his grin turning downright wicked.

that was all it took.

you surged towards him, grabbed him by the his shoulders, turned him around, and slammed him forward over the table. papers and books crashed to the floor.

“jesus christ,” dean barked out, half-laughing. “you’ve lost your damn mind—”

“you just don’t shut up, do you? quit it.”

he twisted his head enough to look at you, still grinning, eyes bright with challenge. “make me.” your hand was already tearing at his belt. dean laughed. “whoa, whoa— slow down there, tiger—”

you yanked his jeans and boxers down in one rough motion.

“not even gonna buy me dinner first, sir?”

your hand cracked down on his bare ass. hard. dean hissed. “shit!”

“you really want to play with me tonight?” you growled. “i dunno,” dean said breathlessly, the smirk still clinging to his face. “you always talk a big game, but i’m still standing, aren’t i?”

you leaned in close, lips brushing his ear. “not for long.” you spat into your palm, stroked yourself once, and lined up behind him. dean craned his neck back, eyebrow raised. “you’re not even— oh, shit!” you buried yourself to the hilt with one savage thrust. dean groaned loudly — raw, loud, back arching violently as his hands clawed at the table. “fuck!—”

“still want to run that mouth?” you asked, grinding in slow, deep. dean laughed yet again, panting. “gonna… gonna take a hell of a lot more than that to shut me up, sir—”

another brutal thrust cut him off.

you started to move, hips pounding into him, raw and relentless, the slap of skin echoing in the empty war room.

dean’s arms shook as he tried to hold himself up. “you—you call this rough? that all you got?”

“you want rough?” you fisted a handful of his hair, yanked his head back. “fine.”

you slammed him forward so hard the table creaked, and began fucking him like a man possessed. each thrust was brutal. deliberate. you stayed deep, dragging it out.

dean’s bravado wavered. “fuck— okay— okay, that’s— that’s— shit!”

“that tight little hole of yours thinks it can wear me down?” you snarled. dean coughed out a chuckle, voice wrecked. “maybe i— hah!— can—”

“you think so?” you said, grinding in deep enough to make him yelp. “i could fuck you like this all night, dean. all fucking night.”

“you— haah— you won’t last,” he gasped, still trying to grin. “i will,” you growled in his ear. “you don’t get it. i’m not gonna cum until i decide you’ve learned your fucking place.” dean’s smirk faltered, just for a second.

“sir,” he said mockingly again, though weaker this time. “you can’t—”

your palm cracked across his ass again.

“say it like that one more time,” you said. “see what happens.”

dean opened his mouth — then gasped as you shifted your angle, ramming into his prostate. his whole body jerked, a choked moan tearing out of him.

“oh, fuck—”

“you feel that?” you murmured. “every single inch of me, and i’m not even close to cumming. gonna keep you full ‘til you can’t stand tomorrow.”

dean shuddered, his cock leaking against the table. you bent over him, lips at his ear. “no condom. you’re gonna be dripping with me. everyone will know exactly who you belong to.” dean moaned, helpless despite himself. you tightened your grip on his hair and forced him upright, his back against your chest, while your other hand wrapped around his throat.

dean’s legs trembled as you started a brutal rhythm, unrelenting.

“still wanna mock me?” you panted.

“y-yeah,” dean gasped, a lopsided grin on his face. “that… that all you—” you cut him off with another punishing thrust.

minutes dragged on. you fucked him mercilessly, sweat dripping down your back, never once letting yourself slip over the edge.

dean came once, then again, the table smeared with his release. his voice was wrecked, his knees buckling, his body shaking — but you still didn’t stop.

his head lolled back against your shoulder. “jesus— fuck, how are you— still— still going?”

“because,” you hissed, “i’m not done with you.” dean whimpered — a sound you never thought you’d hear from him. “gonna breed you,” you said low. “gonna pump you so full you won’t be able to walk, let alone smart off.”

“f-fuck you,” dean croaked, though there was no heat left in it. you sped up, finally, slamming into him so hard the table scraped against the floor.

“beg,” you said.

dean shook his head.

“beg for it,” you growled, tightening your grip on his throat.

his resolve cracked. “please— fuck, please, just—”

you groaned against his ear, shoving deep one last time and finally letting go, spilling into him. you held him there, pressed tight against you, until the aftershocks faded. dean sagged forward, a sweaty, trembling mess, come dripping from him onto the floor. you stayed inside him as you whispered, “got anything smart to say now?”

dean managed a breathless laugh. “…t’was so worth it.”

“mhm? was it?” you murmured with a breath, slowly dragging your cock out of him and then pushing in again.

oh.

dean let out a small breathless gasp, bracing his forearms against the table as your hands slid down to his hips.

“jus’ for good measure.” you said simply and started thrusting again, your pace turning harsh and deep quickly.

dean’s hands were clenched into weak fists, his forehead hitting the wood with a dull thud. “ah— fuck!” he mewled, pushing his hips back to meet yours in a stuttery, shaky motion. “i’m going to fuck you into the damn table,” you said in a whisper, thumbs pressing to the small of his back.

you slowed suddenly, keeping yourself buried deep. dean writhed under you, hating the sudden loss of friction.

“no, no, no, don’t you dare stop—” he babbled out, voice whiny.

“you don’t get to tell me what to do,” you say as you move a hand to the nape of his neck, pressing him into the table. the angle shifts, and you’re abusing his prostate once more.

“mmmhh— mh- ah, fuck.. fuck— fuckin’ hell.. shit!” he moaned loudly as his hand scrabbled backward, fingertips brushing at your hip. he couldn’t even decide what he wanted — push you away or claw you closer — so he just clutched at you helplessly, nails digging into your skin.

“you like that?” you whispered against the back of his neck, pulling almost all the way out, slow and deliberate, until only the tip of you was left inside him. “say it. say you like it.” dean shook his head wildly, even as he arched back for more. “i— nngh— hate it,” he lied, teeth gritted. “fucking hate it.”

“liar,” you said, and slammed back in so deep his breath left him in a rush.

his whole body jerked, a strangled sob escaping his throat. “fuck— fuck— goddammit, sir—” the last word came out unbidden, almost a curse, half-mocking and half-broken.

that got a low laugh out of you, mean and pleased. “there it is,” you purred, pace picking up. “go on. keep calling me that. let’s see how long you last.”

“sir,” he gasped again, this time spitting it like venom— trying to mock you, to get a rise out of you.

you bent low over him, your chest pressing to his back, your hand still keeping him pinned. “you really want to play that game right now?”

“yes,” he panted, though it sounded more like a sob.

so you gave him what he asked for. your thrusts came faster, deeper, the wet slap of skin on skin echoing around the room. he was already a wreck and you weren’t even close to done.

dean’s arms gave out, folding under him so he was lying flat on the table, hips up, taking everything you gave him with no leverage to fight it.

“too much?” you asked, voice soft, teasing, just to watch him shake his head violently.

“not— not enough,” he forced out. “come on, that all you- got?”

you smirked, biting down on his shoulder hard enough to make him flinch. “careful. i can keep going long after you’re wrung dry.”

“you won’t,” dean panted, ever the brat. “you’re all ba-bark.”

you stopped moving again, just stayed buried inside him.

the sound he made was pure agony.

“no, no, no— fuck, please don’t—don’t stop,” he tried to wiggle back against you, desperate, but your grip was iron.

“you sure?” you murmured. “you sure that’s what you want?”

“yes! please, please,” he babbled.

“beg properly.”

there was a long pause, broken only by dean’s shuddering breaths. then, hoarse and reluctant: “please, sir.”

that was all you needed. you pulled out and slammed back in so hard his body jolted forward on the table.

he screamed.

you set a brutal rhythm, fucking him through his own moans, through the wet squelch of sweat-slick skin, through the way he kept trying to hide his face in his arm. every thrust wrung another sound out of him, every hit to his prostate making him see white.

and you still weren’t close to finishing.

“cum for me,” you growled into his ear.

“i—i can’t—i just—” his words dissolved into a wail as his cock jerked untouched, another orgasm ripped out of him with nowhere to go but the ruined papers below.

he collapsed entirely this time, boneless, but you didn’t let up. you just kept moving, riding out his release and pushing him straight into overstimulation.

“can’t— can’t—” he gasped, his voice breaking.