Huntercorp Dean not meeting Cas is a crime actually
He has Negative Charm by the way, the oppostie of how Dean is full of it - so his flirting game is abysmal. He's full of cheesy cringey one-liners that literally never work on anyone, but they go so wildly over Cas's head that they get his attention anyway and end up kind of working.
Cas walks in and Huntercorp Dean is like, "HELLO. Who is this???"
Regular Dean is immediately bristling. He recognises that tone and the way he's leaning back in his seat, clearly checking Cas out. "That's Castiel, he's an Angel."
"I'll say. Every time he looks at me I feel like I'm in Heaven."
Cas voice "Actually you can't get to Heaven from here..."
"Well they must be missing an angel cause you're right here."
"Ah. None of the other angels miss me. In fact I think they're quite glad I'm gone."
Huntercorp Dean winks. "Well you can stay here with me then, cause you're definitely answering all of my prayers right now."
"You're praying to me? I can't hear you." Cas goes a little bashful. "And that's nice of you to say, Dean. You know I try to be around as much as I can."
Now full of enthusiasm because his lines are WORKING Huntercorp Dean continues flirting with Cas with 0 awareness of how bad he is at it while Cas continues to be equal parts confused and endeared.
Meanwhile Regular Dean has his head in his hands wishing a portal would open up and take the other Dean away again.
Pairings: Dean Winchester x Reader, Past Sam Winchester x Reader (Brief/Consensual), Sam Winchester (Catalyst)
Summary: Years of unresolved tension between Dean and Reader have reached a boiling point. Sam, fed up with their denial and knowing their brief past history makes Dean extra sensitive, orchestrates a plan. After a hunt and too much whiskey, Sam deliberately amps up the flirting with Reader, pushing Dean's jealousy until he explodes. A staged near-kiss forces Dean to finally admit what he wants: her. Passionate, rough, and possessive sex fueled by years of pent-up desire and jealousy follows.
Warnings: Explicit Sexual Content, Rough Sex, Jealousy, Possessive Behavior, Manipulation (by Sam), Alcohol Consumption, Arguing, Emotional Confession, Past Sexual History (Sam/Reader), Aggressive Kissing, Biting, Marking, Bruising, Dirty Talk, References to Unrequited Feelings, Angst with a Happy(ish) Ending.
Also any mistakes are my own, please do not repost my work anywhere however reblogs are fine and welcome :)
If you love it, please comment and/or reblog. Let me know your thoughts! :)
**IF YOU DON’T LIKE IT DON’T READ IT**
The whiskey burned a familiar path down Dean’s throat, doing nothing to dull the sharp edge of irritation pricking at him. Across the bunker’s library table, Sam leaned closer to you, laughing at something you’d said, his hand resting casually on the back of your chair. Again. It was the third time tonight Sam’s hand had found its way there, or his arm had brushed yours as he reached for the chips, or his laugh had been a little too loud, a little too focused on you.
"Seriously, though," Sam said, his voice warm and slightly slurred from the bourbon, "that move with the ghost cat? Pure genius. Quickest salt-and-burn prep I've ever seen." His fingers tapped lightly against the chair back near your shoulder.
You grinned, leaning back slightly into the touch, oblivious. "Desperate times, Sammy. That thing was about to shred Dean's favorite flannel." You took a swig of your own drink. "Besides, someone had to save his fashion sense."
Dean grunted, swirling the amber liquid in his glass. "My flannel was fine. And genius? More like reckless."
He aimed the comment at you, but his eyes flicked pointedly to Sam’s hand. Sam met his gaze, a flicker of something knowing – and infuriatingly smug – in his eyes before he looked back at you.
"Reckless gets the job done sometimes," Sam countered smoothly, his thumb rubbing a tiny circle on the chair fabric right by your shoulder blade. Dean’s knuckles whitened around his glass. "Unlike some people who overthink everything." He shot Dean a deliberately pointed look.
You chuckled, nudging Sam’s knee under the table with your foot. "Pot, kettle, Sammy. Remember the Djinn archives? Three days of research for a five-minute fight?"
Sam laughed, a rich, easy sound. "Okay, fair point." He shifted, leaning even closer towards you, ostensibly to grab the whiskey bottle in the center of the table. His shoulder pressed firmly against yours. "But meticulousness has its place. Unlike impulse." Another glance at Dean, loaded with meaning Dean couldn't quite decipher but hated.
The air crackled with tension Dean couldn't name, but it felt like sandpaper on his nerves. This wasn't just Sam being friendly. This felt… targeted. Calculated. And you, blissfully drunk and touch-starved yourself (because Dean was a stubborn, terrified idiot), were just soaking it up. Why wouldn't you? Sam was safe. Sam was your best friend. Unlike Dean, who froze whenever things got too real.
Later, stumbling slightly towards the kitchen for water, you passed Sam leaning against the doorway to his room. He caught your arm gently as you went by.
"Hey," he said softly, his voice low and intimate in the quiet hallway. "You okay? Seemed like Dean was being extra grumpy tonight."
You sighed, leaning against the opposite wall, facing him. The whiskey made the world pleasantly fuzzy at the edges. "Just Dean being Dean. Probably pissed I used the last of the good coffee this morning." You rubbed your temples. "Or maybe he just hates seeing anyone happy."
Sam stepped closer, invading your personal space just enough to make you look up. His expression was soft, concerned. "Maybe he hates seeing you happy with someone else." His hand came up, not touching your face, but hovering near your cheek, his thumb brushing the air near your jawline. His gaze dropped to your lips for a fraction of a second too long.
You blinked, the alcohol slowing your processing. "Someone else? Sam, it's just... you." You offered a tired smile. "And neither of us is getting laid anytime soon, so..."
Sam chuckled, a low rumble. "True enough." He leaned in slightly, his head dipping. His intention wasn't clear – a hug? A kiss on the cheek? But the angle, the closeness, the way his eyes held yours… it looked like he was leaning in for a kiss. And you, drunk and confused by his sudden intensity, didn't pull away immediately.
The heavy library door slammed open.
"WHAT THE FUCK DO YOU THINK YOU'RE DOING?"
Dean’s roar ripped through the quiet hallway. He stood framed in the doorway, face flushed with fury and whiskey, eyes blazing as they locked onto Sam, who was still leaning close to you, his hand near your face. Dean stormed forward, shoving Sam hard in the chest, sending him stumbling back a step.
"Dean!" you gasped, startled and suddenly sobering up fast. "What the hell?"
Sam held his hands up, palms out, but there was no surprise on his face. Only grim satisfaction. "Whoa, Dean! Easy! We were just talking!"
"Talking?" Dean snarled, getting right in Sam's face, ignoring you completely for a terrifying moment. "Looked like a hell of a lot more than talking, Sam! What, you think you can just swoop in whenever? After everything?"
"After what, Dean?" Sam shot back, his voice deliberately calm, stoking the fire. "After you've spent years pretending you don't feel anything? After you let her think she doesn't matter? Yeah, maybe I decided she deserves someone who actually wants her!"
"I DO WANT HER!" The words exploded from Dean, raw and ragged, echoing off the bunker walls. He froze, eyes wide, as if shocked by his own outburst. His chest heaved. He slowly, painfully, turned his head to look at you.
The world stopped. The fury in Dean’s eyes hadn't dimmed, but beneath it, raw and terrifyingly vulnerable, was something else. Something you’d only ever glimpsed in fleeting moments, quickly buried. Possession. Need.
Love.
Sam took a deliberate step back, his work seemingly done. "Took you long enough," he muttered, shaking his head, but there was relief beneath the exasperation. He gave you a small, almost imperceptible nod before turning and walking purposefully towards his room, leaving you alone in the hallway with Dean.
You stared at Dean, your heart hammering against your ribs. "You... you what?" Your voice was barely a whisper.
Dean didn't answer with words. He closed the distance between you in two strides. His hands, rough and shaking, framed your face. His eyes searched yours, the anger warring with a desperate, aching hunger. "You heard me," he growled, his voice thick. "I want you. You should be mine."
Then his mouth crashed down onto yours.
It wasn't gentle. It was claiming. Possessive. A desperate, furious sealing of the confession ripped from his soul. His lips were hard, demanding, his tongue plunging into your mouth with a hunger that stole your breath. You gasped against him, your hands flying up to grip his shoulders, not to push away, but to hold on as the world tilted violently. Years of pent-up longing, frustration, and jealousy ignited like gasoline.
He broke the kiss just as abruptly as he started it, breathing raggedly against your lips, his forehead pressed to yours. "Tell me to stop, I’ll stop," he rasped, his voice wrecked. "Tell me no. Tell me you don’t want me. That I’m wrong."
You looked up into his stormy eyes, seeing the fear beneath the fire, the vulnerability beneath the possessiveness. The years of stolen glances, hidden smiles, and aching silence flashed before you. "You're not wrong," you breathed, your own voice trembling. "I want you. I’m yours, Dean. Always have been."
A low groan tore from his chest. He didn't hesitate. He scooped you up, your legs instinctively wrapping around his waist, and carried you down the hall towards his room. He kicked the door shut behind them with a force that rattled the frame.
He didn't make it to the bed. He pinned you against the cool metal door, his mouth reclaiming yours in another searing kiss. His hands were everywhere – tearing at your shirt, shoving your jeans down your hips. His own clothes followed in a frantic tangle of fabric and belts.
"Shoulda done this years ago," he growled against your neck, biting down sharply on the tender skin where it met your shoulder. The sharp sting sent a jolt of pure electricity straight to your core. "Shoulda claimed you the second I saw you." His hand slid between your legs, finding you already slick and ready. "Fuck, you're soaked. For me?"
"Yes!" you gasped, arching into his touch as his fingers plunged deep, curling ruthlessly. "Always for you, Dean!"
"Good," he snarled. He withdrew his fingers, gripped your hips hard enough to bruise, and lifted you slightly. With one powerful thrust, he buried himself inside you to the hilt.
You cried out at the sudden, delicious stretch, the fullness, the sheer rightness of it. He didn't pause. He set a punishing pace immediately, driving into you with deep, hard strokes that rocked you against the door. The friction was intense, amplified by the raw emotion pouring off him.
"Tell me," he demanded, his breath hot and ragged against your ear. His thrusts were relentless, each one pushing a gasp or moan from your lips. "Tell me you're mine."
"I'm yours!" you cried, clawing at his back, meeting his thrusts with equal ferocity. "Dean, I'm yours!"
"Damn right," he growled, shifting his angle slightly, hitting that spot that made stars explode behind your eyelids. "And you liked it, didn't you?"
His hand slid down, fingers finding your clit, rubbing harsh circles. "Liked seeing me lose my shit? Seeing me finally break?"
"Yes!" The admission was ripped from you, half-shame, half-triumph, as pleasure coiled tighter and tighter.
"God, Dean, yes!"
"Knew it," he muttered darkly, slamming into that perfect spot again and again, his fingers relentless on your clit. "Knew you wanted me to snap. Wanted me to finally take what's mine." He kissed you again, savage and possessive. "Show me. Come for me. Scream my name so Sammy hears exactly who you belong to."
His words, filthy and perfect, combined with the brutal rhythm of his hips and the skilled torture of his fingers, pushed you over the edge. Your orgasm detonated violently, shattering your vision into white light as you screamed his name, your inner muscles clamping down hard around him in pulsing waves.
The feel of you milking him triggered his own climax. He buried himself impossibly deep with a final, guttural groan that vibrated through your entire body. "Mine!" he gasped against your neck as he emptied himself inside you, his body shuddering violently against yours.
For long moments, the only sounds were their ragged breathing and the frantic drumming of their hearts pressed together. Dean stayed buried within you, slumped against you, his forehead resting on the door beside your head. His weight pinned you, but it felt like an anchor, not a burden.
Slowly, he pulled out, lowering you gently until your feet touched the floor. Your legs trembled, barely holding you up. He leaned back against the door, chest heaving, watching you with eyes that were still dark with passion, but now also filled with a dazed wonder and a hint of lingering possessiveness.
He reached out, his calloused thumb brushing gently over the bite mark he'd left on your shoulder. "Sorry," he murmured, though he didn't sound particularly sorry.
You touched the mark, then reached up to trace the line of his jaw. "Don't be." You leaned forward, resting your forehead against his chest. "Sam planned that, you know. The hallway."
Dean stiffened, then let out a harsh, disbelieving laugh. "That little son of a bitch." He wrapped his arms around you, pulling you tight against him. "Gonna kill him tomorrow."
You smiled against his skin, the warmth of him, the solid reality of him holding you, finally chasing away the last ghosts of doubt. "Maybe thank him first?"
Dean grunted, nuzzling into your hair. "Maybe." He was quiet for a moment, his hand stroking slow circles on your bare back. "...Meant it, you know. What I said. You're mine."
You tilted your head up to look at him. "And you're mine."
A slow, genuine smile, rare and breathtaking, spread across Dean Winchester's face. "Yeah," he breathed, leaning down to capture your lips in a kiss that was infinitely softer, sweeter, but no less possessive than the first. "Yeah, I am."
Outside Dean’s door, leaning against the wall just out of sight, Sam Winchester smirked into his glass of water. Mission accomplished. He took a quiet sip and padded back towards his own room. Tomorrow was gonna be fun.
Summary: A night at a local dive was supposed to be a way to relax after a hunt. But when a charming stranger starts paying you the attention Dean hasn’t quite figured out how to give, the tension that’s been building for months finally boils over. There in a crowded bar in the middle of nowhere, Dean Winchester finally stops running from the truth—and he isn't letting anyone else stand in his way.
Rating: 18+
Word Count: 2355
Warnings: Smut, Possessiveness, Jealousy, Marking, Mild Angst, Language
Part 1
Dean kicked the motel door shut behind you, but not before he shrugged off his flannel and hooked it over the outside handle—a silent, practiced warning for Sam to stay away. As soon as the motel door slammed closed Dean had you pinned up against it. His hands were everywhere. His mouth crashed down on yours, his tongue seeking yours as he pressed the full weight of his body against you. Your hand slid up to grasp his hair at the nape of his neck while your other hand snaked around him, trying to pull him closer, if that was even possible.
Dean growled into your mouth. His hand slid down to hike your thigh up against him as he pulled back, breathless. His mouth worked its way down kissing along your jaw and down to your neck. He was sucking marks on your neck and down near your collarbone that would be obvious but you didn’t care. All you could feel was heat and a desire so strong it was threatening to make your legs give out.
Without warning Dean slid his hands under your thighs near your ass and hauled you up his body like you were weightless. Your legs wrapped around him instinctively. He was still kissing along your neck when he carried you over to the bed, kicking off his boots as he went. He laid you down on your back, climbing over you in one smooth motion.
“Off, Dean,” you said, tugging at his shirt. “Need this off.” He obliged, leaning back just long enough to quickly tug his black t-shirt over his head and toss it behind him. That gave you half a moment to tug your own shirt off along with your bra.
His gaze fell over your perky breasts and his breath caught, audibly, eyes widening. “You’re so perfect,” he whispered, as much to himself as to you.
He lowered back down, kissing over your collarbone again and then slowly running his tongue down your chest until he was flicking it gently over your hardened nipple. You gasped softly at the sensation. Dean took your nipple into his mouth sucking gently before pulling back and nipping at it, causing you to arch into him. “That’s right, baby. You like that?” he crooned. You nodded feverishly. His large, calloused hands ran over your sides, brushing against your ribs, causing you to shiver under his feather-light touch.
Positioned between your legs, Dean started kissing along your neck again. Your hands were running over his broad, muscular shoulder blades when he ground his core down into you, causing you to arch up into him with a soft moan. You could feel his large dick straining against his jeans. “God, I’ve wanted you for so long. Wanted this,” Dean groaned. “Been losing my fuckin’ mind for months. Knowing you’re right down the hall every night,” he growled. “And when we hunt… the nights in motels, just a few feet away- Shit..”
“I.. I didn’t know. I thought you just saw me as a friend, a hunting partner,” you confessed. “Why didn’t you say something?”
He had worked his way down with his mouth. In between light kisses along your navel he shrugged and said, “Dunno. Didn’t think you’d be interested in me.”
Your mind was reeling. It couldn’t comprehend not being interested in Dean. “What?”
He pulled back and looked up into your eyes, his darkened green eyes softening for just a moment. “Yeah. Didn’t think you’d want a guy like me. I don’t have much to offer and well you know how the life goes..” he trailed off, kissing the curve of your hip.
“Dean, I’ve wanted you since the moment we met. I love you, you idiot,” you blurted out before you could overthink it.
His head snapped up. “You- you what?” Dean’s hopeful green eyes locked onto yours but before you could answer he surged up, lips pressing to yours roughly. He ground down into you again as he took your breath away with the most passionate kiss you’d ever experienced. All tongue, teeth and a small growl flowing into your mouth.
Reaching down between your bodies you grasped at his buckle. Yanking his belt open with a soft clink. He pulled back, his chest heaving. You let out a breathless sound that made his cock twitch. He leaned back on the bed, deftly undoing your jeans and pulling them down along with your panties, while you lifted your hips to help, before he yanked his own jeans off and tossed them aside.
Leaning back down, Dean looked up at you from between your thighs. He hooked your legs over his shoulders and pulled you closer to him with a grin and a raised eyebrow, staring up at you, his hot breath ghosting over your sensitive, wet curves. You smiled down at him, eyes blown wide with desire. He didn’t hesitate. He didn’t tease. Dean dove right in.
"Deeeaaan," you moaned loudly as he sucked on your clit. He hummed in response, the vibrations causing your hips to buck up into him. He slid a strong arm over your stomach, pinning your hips to the mattress to keep you still.
Placing open mouthed kisses down your pussy he worked his way to your entrance. “You’re soaked,” he murmured, your thighs muffling his words. “This all for me?” he asked in awe as he slid his tongue into your warm entrance.
You didn’t answer. You couldn’t. So instead you let out another soft moan. After working you open with his tongue for a bit he moved back up to your clit, dragging a long slow strip up your pussy with his tongue. Once he was attached to your clit again, he alternated between soft and ferocious movements causing you to try to arch and buck again, without doing much good as he still had you firmly held in place.
Your legs began to shake and a feral moan flew out of your mouth. Dean stuck two fingers inside you and increased the pressure on your clit with his tongue if that was even possible. The combination and his expert skills sent you flying over the edge. You clenched tightly around his pumping fingers and a blinding white light overtook your vision. Dean didn’t let up and worked you through the intense orgasm. You didn’t recall screaming but as you came back down your throat was a little raw.
Raising up and wiping his glistening chin and stubble, Dean had a crooked, smug smirk displayed proudly across his face. “Wow, baby, that was something. You’re so wet I thought I might drown,” he teased.
Your face would have flushed at his words if it wasn’t already heated and pink from the best orgasm you’ve ever had. The orgasm that Dean just gave you. You still can’t believe this is really happening. You keep expecting to wake up from a dream, laying in your bed in the bunker, aching for him.
You murmured something incoherent in response and he chuckled. He lowered his body over yours and began to kiss you softly. You could taste yourself on his lips, on his tongue. Reaching up to thread your fingers into his hair you pulled him closer.
Dean finally breaks the kiss and you whine, literally whine, “Please. Dean, please.”
“Words,” he half laughs. “Please what?” he asked. Those big green eyes locked on yours and a small smirk on his face again, he said, “Tell me what you want.”
Giving a frustrated sigh, you wiggle underneath him, causing his hard cock pressed against your thighs to twitch. “You, Dean. Need you. Need you inside of me. Now, please,” you beg.
He slowly brushes a strand of hair out of your face while staring down at you as if you’re the best thing he’s ever seen, the answer to all his prayers. “I got you.”
Slowly, carefully, he pushed into you inch by inch. You gasped as he entered you. Dean was not small, he was huge and your body struggled to take him at first. He continued to glide through your moist softness slowly, giving you time to adjust. Once he was buried to the hilt he stayed there, not moving, and leaned in to give you another soft kiss, running his tongue over your bottom lip as he pulled back just enough for his words to ghost over your mouth. “You okay?”
Taking a deep breath you nodded. “Yeah, I’m good.”
Dean gave a short nod and began to move. The slight pain of his size quickly gave way to pleasure as he pulled almost all the way out before sinking back in, letting out a low guttural groan. “Fuck, baby,” he hissed. “You’re so tight. Taking me so well,” he muttered into your neck. You let out a soft, breathy sound at his praise.
Before long, he picked up the pace and began to thrust into you. You wrapped your legs around his back, heels digging into his ass to drive him deeper. Dean let out another deep groan and closed his eyes, leaning his head back. “Shit,” he breathed.
You released your legs from his back and you raised one up over his shoulder. He raised an eyebrow as he continued to move with purpose. The smirk fell back into place and he didn’t say anything but began to thrust harder, deeper. Dean’s lips found yours again but this time it wasn’t soft. It was all heat and hunger.
Pulling back breathless, you tossed him a smirk of your own as you clenched around him.
“Fuck,” he hissed. “You keep that up and I’m not gonna last, baby.”
You did it again, harder and holding it slightly longer. “Shit,” he practically gasped. “You’re trying to kill me.”
You chuckled and said, “Maybe.” In response, he pounded into you harder, stealing the breath from your lungs. “Dean!” you moaned loudly. “I..I’m-”
“I know,” he cut in. “Cum with me, sweetheart,” he rasped.
Just like that, you let go, cumming again, the world spinning a bit as loud moans escaped your lips. His name, over and over again. He followed almost immediately, spilling into you, hot and powerfully.
Dean rolled you both over so that you were laying on top of him but still connected. You could feel the mixture of you and him sliding down onto his thighs but he didn’t seem to notice or maybe just didn’t care. As you both tried to catch your breath he pulled your hair back out of your face and you laid your head on his heaving chest. You ran your hand lightly over his muscular shoulder and bicep, sighing softly, satiated.
After a few moments of silence other than yours and his breathing, he reached down and tilted your chin up to look at him. Dean’s bright green eyes locked on to yours with an intensity you weren’t expecting in that moment. “I love you too,” he whispered. “More than you can ever imagine,” he said, his arms squeezing you just a little tighter.
Your breath hitched and you felt a flutter in your chest at his words. You closed the fraction of the space to press your lips to his, slipping your tongue into his mouth for a slow, meaningful kiss. As you pulled back, your words were hot against his mouth, “I could get used to this.”
“I think I already have,” he replied. Dean’s smile was easy now, no smirk or smugness, just a genuine, content smile played on his lips.
~~~~~~~~~
The sunlight streamed through the gap in the heavy motel curtains, landing right across your eyes. You groaned, shifting deeper into the warmth beside you. Before your sleepy mind could register where you were, you expected to be alone in bed.
Then you felt the heavy, solid weight of Dean’s arm draped over your waist and his rhythmic breathing against the back of your neck. It wasn't a dream.
Dean stirred, his grip tightening instinctively as he pulled you closer, burying his face into your hair. "Go back to sleep," he grumbled, his voice gravelly and thick with sleep.
"Dean," you whispered, a smile tugging at your lips. "We have to-"
Three sharp, rhythmic knocks against the door interrupted your next words.
"Dean? You in there? It’s checkout time and the diner down the street has actual coffee."
Sam.
Dean froze. You could feel his heart speed up against your back. He let out a long, frustrated breath into your shoulder before slowly propping himself up on one elbow. He looked down at you, his bright green eyes soft and hair a mess, before glancing at the door with a look of pure annoyance.
"Go away, Sammy!" Dean shouted back, though there was no real heat in it.
"Dean, I can hear two people talking in there," Sam called out, his voice tinged with a mix of realization. "And your flannel is hanging off the doorknob on the outside. You’re not exactly being subtle."
Dean looked at the door, then back at you, a sheepish grin spreading across his face. He leaned down, giving you a quick, firm kiss.
"I'll be out in like ten minutes, Sam! Get a table." Dean yelled, finally sitting up and reaching for his discarded jeans.
He turned back to you, watching as you sat up, the sheet falling away. The smugness from the night before was gone. It was replaced by a new, genuine warmth you’d seen right before you fell asleep.
"So," Dean said, hooking a finger under your chin. "I guess the secret's out."
"Was it ever really a secret?" you teased back. "I think Sam’s been waiting for you to grow a pair for six months."
Dean let out a genuine bark of a laugh. "Yeah, yeah. Maybe. But now that I’ve got you, I'm not letting this go. I'm not letting you go."
He pressed one last, lingering kiss to your forehead before finally reaching for his shirt, a small smile still playing on his lips as the chaos of your lives waited just outside the door.
a/n: Hey. It’s been a minute, huh? Almost four years, lol. Well, I thought I’d write something small again, and what better way to get back into it than with a little piece about Dean fucking Winchester? The Winchester brothers are my current drug, so you can expect more of that to come. Enjoy!
summary: Pressing his ear against the wall, Dean’s mind swirled with a whirlwind of emotions he never expected to feel. His brother Sam, the one person he’s always protected, was now with someone Dean couldn’t stop thinking about. The sounds from the next room making his chest tighten with a mix of jealousy and something far more dangerous.
warnings: Jealousy, Inappropriate thoughts about a sibling’s partner, Sexual content, Mature themes, Explicit language, Emotional conflict, Tension and discomfort
Dean Winchester had never been jealous of Sam’s love life. Why would he? There had never been a reason for it. Dean had always done his own thing, taken his life as a hunter for what it was—restless, dangerous, with no room for commitments. Relationships in this job were nothing but a ticking time bomb, so he never even considered them. One-night stands were easier. No strings, no complications. No drama, no risk, no heartbreak.
And then you came along.
The brothers had met you on a hunt. At first, you were just some stranger, a witness with too many questions. Then you became an ally. And before Dean even realized it, you were just… there. Always. What had initially seemed like an unnecessary burden—one more person to protect, one more soul to lose to this life—turned out to be a damn blessing. You weren’t helpless. Quite the opposite. You were sharp, capable, unafraid to challenge Dean. At some point, it became natural to have you sitting in the backseat.
But then something changed.
Dean knew his brother better than he knew himself. He noticed the shift in Sam’s gaze the moment it happened—how his eyes softened when they landed on you. And worse, he saw the same change in yours.
He told himself he didn’t care. That it didn’t matter. Maybe it just bugged him that you two had kept it a secret for so long. Yeah, that had to be it—the secrecy. The feeling of being left out. But then it wasn’t a secret anymore. And Dean realized that the deception hadn’t been the thing tying his stomach in knots. It was the way Sam held you. The way you leaned into him, like he was your damn home.
Dean was happy for his brother. Really. After everything they’d been through, Sam deserved happiness. But fuck if it didn’t eat him alive every time he saw Sam’s hand wrapped around yours. Every time he had to watch you kiss him like he was the best thing that had ever happened to you. It burned, but Dean said nothing. He wasn’t the kind of guy to let anyone see when something cut too deep. So he shoved the feeling down, just like he did with everything else that had the power to hurt him. He laughed louder, teased Sam harder, played the cool big brother while feeling like a goddamn idiot inside.
Because for the first time in his life, Dean Winchester wanted something he couldn’t have. Not that he’d ever admit it. Dean Winchester wasn’t jealous of his little brother. Not once. So why the hell did it feel like his stomach twisted into knots every time he caught you looking at Sam? Laughing at his jokes, even the bad ones. Reaching for his hand without even thinking. Giving him those looks—those damn looks Dean had never gotten, not from someone like you. Of course, it ended up like this. Sam was the one with the college brain, the stupidly perfect smile, the goddamn puppy eyes. Sam had always been the guy women actually wanted. Not like Dean, who was good for a night but never for more.
And maybe that was the real reason it gnawed at him. Because you weren’t just anyone. Because if things had been different—if life had played out another way—maybe, just maybe, you could’ve been his.
Dean didn’t dwell on what-ifs. That was a surefire way to lose your mind in this life. But damn if they didn’t creep in anyway. Late at night, when the motel room was too quiet, when the whiskey wasn’t enough to drown out the thoughts he didn’t want to have.
Maybe, if he wasn’t so damn good at pushing people away, he would’ve done something about the way you made his chest tighten. Maybe, if he had just fucking tried—
But it didn’t matter.
You weren’t his.
You were Sam’s.
And Dean Winchester never stole from family.
So he swallowed it down, let the bitterness settle deep in his bones, and kept moving forward like he always did. Because that’s what he was good at—taking the hits, standing back up, pretending it didn’t hurt.
But some nights, when sleep wouldn’t come, he let himself wonder.
If things had been different… would you have ever looked at him the way you looked at Sam?
And if you had—would he have let himself have you?
He couldn’t help but sink even deeper into those thoughts. If you had been his—how would your skin have felt beneath his fingertips? What soft, sweet sounds would you have made if he had touched you just right? Dean felt no shame as his hand wrapped itself around his dick. Ever since you and Sam had gotten together, you always took your own motel room. So there was no reason not to let himself indulge. A quiet groan escaped him at the thought that it was your soft hand touching him—not his own.
He imagined your lips parting ever so slightly, just enough to let soft, breathy moans slip past them. His strokes grew quicker and he was panting hard. If he closed his eyes and focused hard enough, he could almost see your big, innocent eyes locked on him. He could almost hear the soft sounds slipping from your lips—until it hit him that he wasn’t imagining them at all. They were real and they were coming from the room next to his.
Had you and Sam been together like that? It never crossed his mind before—probably because thinking about his brother being intimate just wasn’t something he ever did. And rightfully so.
What Dean did next, was something he’d take to his grave.
He pushed the thought of his brother aside and pressed his ear to the wall. Now he could hear you, clear and unmistakable.
“Fuck, Sammy…”, you moaned. “Always making me feel so good…”
Dean visibly winced at those words, but the next thing you said made him shut his eyes.
“Please, please, please… Ruin me, Winchester.”
There he was, standing in his motel room, his ear pressed against the wall that connected to yours, stroking himself to the sounds of you being pleasured. Dean imagined himself between your legs. He’d eat your pussy like a starved man, worship your body in every way imaginable. He’d take his time, tracing every curve of your body, his hands exploring with a slow, deliberate touch, seeking out the places that would make you gasp, make you shiver. Each soft caress would be a silent question, testing, learning, until he found the exact spot that would have you melting under his touch. He was drawn to the idea of hearing you lose yourself in the pleasure, curious to see how far he could push you, wanting to hear the highest, most breathless note you could reach.
He’d savor the moments, the way your breath hitched with every shift of his fingers, how your body would arch toward him, craving more. It was like an unspoken dance, each movement a step closer to the edge, both of you lost in the rhythm of it all.
The sounds from the other side of the wall were enough to drive him mad. Every moan, every breathy exhale of yours was a trigger, setting off a chain reaction in him he couldn’t control. And it wasn’t just the physical sound—it was the feeling behind it, the way it seemed to echo in his mind, a constant reminder of what he couldn’t have.
He came hard, coating the wall. Fuck. He wasn’t supposed to be doing this, wasn’t supposed to want this. It didn’t matter how badly his body reacted to the sound of you. Dean pulled his ear away from the wall, the heat still simmering inside him, but the reality of it crashing down like cold water. This wasn’t right. He’d gone too far—had let his mind wander where it shouldn’t have. His brother was happy, and that should’ve been enough for him. But why the hell did it feel like a betrayal of something deeper than he was willing to admit? He turned away, stumbling back toward the bed, his mind racing. This feeling—this burn—wasn’t something he could ignore forever. But for now, he’d have to. For now, he’d bury it. Just like everything else.
