The Voice says I'm Almost out of Minutes

You were theirs. They had decided that long before you realised you had no choice in the matter.

They met you at your worst—bloody, shaking, stupid with adrenaline. Your first real hunt had gone sideways, and whatever experience you thought you had meant nothing when the claws hit skin. You should've died. You were ready to. But Sam was there, and Ruby moved like smoke, and the thing was gone before you even saw it clearly.

"Poor baby," Ruby had murmured, crouching beside you while Sam checked your wounds. "Too pretty to go out like that."

You'd flinched when she touched you, and she smiled like that was her favourite part.

You never asked why they took you with them. Sam had said something about keeping an eye on you, but his mouth twitched like it wasn't the whole truth. Ruby just grinned and said you were better off not knowing. You nodded. You didn't ask again.

At first, they let you come on hunts. Small ones. Salt-and-burns, poltergeists. Sam showed you how to hold a blade properly. Ruby taught you how to lie. You were good at both.

But over time, they started leaving you behind.

"It's too dangerous," Sam said.

"She's not ready," Ruby added, her hand stroking your back through the thin cotton of your shirt.

You didn't argue. You told yourself it was kindness. That they were protecting you. That it wasn't about keeping you soft.

But then came the looks. The touches. The nights where Sam would come back covered in blood, eyes sharp with something feral, and Ruby would kiss his knuckles while you watched from across the room, trying not to shake.

They never made you watch. But they never really let you look away, either.

They talked about him sometimes.

Dean.

You only ever caught the name in whispers. "He wouldn't understand."  or,"Dean would've stopped this." or, "Dean's gone." Always followed by a pause. Always followed by Ruby looking at Sam like she was daring him to fall apart.

You didn't know who he was. You didn't ask.

Every time you got too close to the door, every time you hovered outside just long enough to hear more, one of them would call out like they felt you there.

Sam's soft: "Baby?"

Or Ruby's syrupy: "Sweet thing, come here."

You always obeyed.

Sometimes, when they thought you were asleep, Sam would sit at the edge of your bed and run his hand down your hair. Just once. Just enough to make your breath catch. Sometimes, Ruby would slip under the covers beside you and whisper nonsense until you drifted off—half-lullaby, half-possession.

You weren't sure when it stopped being strange. You only knew that when they were gone too long, your chest felt empty. And when they came back, you'd breathe again. You weren't stupid. You just didn't know how to leave.

The rain started two hours ago.

It tapped against the window in slow, steady beats, like a clock winding down—like something counting out the seconds until they came back. You sat curled on the end of the bed in your pyjamas, legs pulled up, sleeves hanging past your wrists. The television glowed faintly in the dark, but you weren't watching. You hadn't really watched anything in days.

You just waited. You always waited.

The door creaked open a little after midnight.

Sam came in first, wet to the shoulders, eyes shadowed and far away. Blood soaked one sleeve of his shirt. You didn't ask whose. Ruby followed behind him, skin shining with water, hair stuck to her cheeks like tendrils.

She smiled when she saw you. Not kind. Not cruel. Just... like she already knew.

"Still awake, baby?" Her voice was smoke and candy.

You nodded. Sam didn't say anything. He locked the door behind them, set his knife down on the table like he was placing something sacred. You watched his hands—big, veined, careful. Ruby peeled off her jacket and let it drop to the floor.

"Poor thing," she murmured, walking past him. "All alone in the dark. Bet you were scared."

You opened your mouth to protest, but she was already kneeling in front of you, wet fingers brushing your knee where your pyjama shorts had ridden up. Her touch was cold. You shivered.

"Didn't like being away from us, huh?"

Sam sat down in the chair across from the bed, his legs spread wide, elbows on his knees. His eyes never left you.

"She hates it," he said softly. "I think she's scared we won't come back."

You looked down, cheeks burning.

"I'm not—"

"It's okay," Ruby cooed. "You should be scared. There's bad things out there, sweet girl. Things that want to hurt you. But we'd never let that happen." She leaned closer, nose brushing your jaw. "You know that, right?"

You nodded. Her hand slid higher on your thigh.

"You're a good girl."

There had been... moments.

Once, in another town, Ruby had let you sleep against her in the back of the car, and you'd woken to find her fingers in your hair and Sam's eyes on your legs in the rearview.

Once, when you'd had a nightmare, Sam had pulled you into his lap, shirtless and half-asleep, and you'd felt him hard under you. He didn't move. He didn't stop either.

Once, Ruby had kissed your neck while laughing at something Sam said, and you'd gone stiff all over, heart beating like you were running from something. But she only giggled and said, "So easy to fluster. It's adorable."

You weren't sure when your body had stopped listening to you. Or when the idea of leaving had started to sound like dying.

Ruby climbed up behind you on the bed now, curled against your back, legs bracketing yours.

"You've been so patient with us," she whispered against your neck. "Hasn't she, Sam?"

He hummed low in his throat, eyes raking down your frame.

"She's always good," he murmured. "Even when she doesn't understand."

Your breath caught. Ruby kissed just behind your ear.

"Do you want to understand, baby?"

You nodded before you knew what you were agreeing to.

Ruby smiled against your skin. Sam stood slowly, crossing to the bed, and the air changed—thickened. You watched him the whole way, your lips parting when he reached out and brushed a strand of hair from your cheek.

"We'd never lie to you," he said, low and warm. "But there are things you're not ready for. Things that would scare you."

"We keep you soft because we love you," Ruby added, her hand sliding up your arm. "Don't you like being soft for us?"

You swallowed hard. "I... I think so."

Sam's mouth curled at the corner.

"That's our girl."

He leaned down and pressed his lips to your forehead—so tender it made your eyes sting. His hand cupped your jaw, thumb brushing the corner of your mouth.

"You don't have to think so," he whispered. "You just have to be."

They didn't kiss you that night. They didn't touch you like that. But Ruby held you in bed, and Sam sat in the chair until morning, watching. His hands didn't stop shaking. You didn't ask why.

You dreamt of red eyes and whispered names and Sam's voice saying, "She's ours. No one touches her but us."

You woke up aching and didn't know why.

They thought you were asleep. You were supposed to be. The lights were off, your hoodie was still warm from Ruby's perfume, and you'd curled up like always—safe and small beneath too many blankets in too big a bed.

But something about the way they said "we need to talk" had twisted in your chest.

Ruby's hand had been gentle on your back as she whispered to Sam that they'd take the room next door. Just for a bit. Just to "talk business." You'd nodded sleepily, like a good girl. Like someone who didn't immediately sit up the second the door clicked shut.

Now?

Now you were barefoot on the cheap motel carpet, heart fluttering, palm pressed to the adjoining door like it might burn you.

It was cracked open. Just an inch. Just enough.

Their voices leaked through, low and urgent.

"She's not ready," Sam was saying. His voice was strained—tired, fraying at the edges. "She's barely holding on as it is. If we push too hard—"

"She's perfect, Sam." Ruby's voice was velvet and smoke. "She's soft, scared, completely dependent. She'd do anything you asked."

Silence.

Then Ruby again, slower this time. Sharper.

"You think you're protecting her by waiting. But you're just dragging it out. You're making her confused. She doesn't know what you want. And she's starting to wonder."

Something slammed—maybe his hand against the table, maybe his fist against the wall. You pressed your hand tighter to the doorframe, mouth dry.

"She's pure." Sam again. Quieter. Like it hurt to say. "She trusts us. I don't want to ruin that."

"You already have." Ruby's tone turned sweet. "And she loves you for it."

You swallowed hard. And then—just as your breath caught and you started to step back—

"She's here."

Your blood turned to ice.

"She's listening."

Ruby opened the door before you could run.

She stood framed in soft yellow light, one shoulder bare, hair tumbling over her collarbone. Her lips curved when she saw you—like a cat catching something small and trembling.

"Hi, baby."

Your voice caught. "I—I didn't mean to—"

"Of course you didn't," she purred. "Come here."

You hesitated.

Her fingers extended slowly. Her voice softened into something intimate and honey-warm.

"You don't have to listen at the door, sweet thing. If you want to know what we're talking about, you just have to ask."

You stepped forward before you meant to. Her hand curled around yours and tugged you gently into the room.

Sam was standing beside the table, hands braced on the wood like he'd been holding himself up. His eyes met yours—and he looked wrecked. Pupils blown wide. Jaw clenched. Like you'd caught him mid-sin.

"She shouldn't—" he started, but Ruby cut him off.

"She should."

She brought you closer, her body warm behind yours as she pressed you into Sam's line of sight.

"You want to protect her?" She whispered, lips ghosting your ear. "Then stop pretending she doesn't already belong to us."

Sam exhaled hard. His gaze dropped—your bare legs, the hem of your sleep shirt, the way your breathing had turned shallow.

"We're not trying to hurt you," he said hoarsely. "You know that, right?"

You nodded. You meant it. Your voice trembled anyway.

"I trust you."

Ruby made a pleased sound behind you. Her hands skimmed your waist, resting low on your hips.

"Good girl," she murmured.

You felt her smile against your neck.

"That's all we've ever wanted."

They didn't kiss you. Not yet. But Ruby turned you around in her arms, pressed your forehead to hers and said:

"You're already halfway gone, baby. Just let go."

Sam stood frozen, fists clenched at his sides. You didn't see the moment he stepped forward—but you felt it. The heat. The pull. The weight of him.

"We'll take care of you," he whispered. "You don't have to think anymore. You just have to be ours."

You closed your eyes and nodded. You didn't understand what was wrong with Sam—but something was.

His chest was rising too fast. His jaw clenched and unclenched like it was wired too tight, and his eyes... his eyes looked wrong. Black-ringed, glossy, so blown out you could barely see the colour. He looked at you like he was starving.

Like he'd been starving for a while.

Ruby was calm. Radiant. She moved with syrup-slow precision, curling one hand around your wrist and bringing it to her lips as she smiled at Sam.

"She's so good for us," she murmured. Her breath was warm against your skin. "Aren't you, baby?"

You nodded before you even knew what you were agreeing to.

Sam made a strangled sound in the back of his throat. His fists tightened where they hung at his sides.

"Ruby..." he said low, like a warning.

But she just giggled—light, pretty, dangerous.

"She wants this," she said simply. "You think I haven't seen the way she watches you? The way she trembles when you say her name?"

She turned toward you, brushing a finger along your jaw.

"Don't you want to be touched, sweet thing?"

You couldn't speak. You could only nod again, your lips parted, breath shaky. You felt like your whole body was made of heat and nothing.

Ruby kissed you before you could think.

It wasn't soft—not really. It was slow, but insistent, her mouth warm and firm against yours. Her hands gripped your waist like she owned you. Like she had every right. Her tongue slipped past your lips and you gasped into it, your knees going weak, clinging to her shirt like it might save you.

When she pulled back, you were dizzy.

"See?" She said sweetly. "So easy."

She led you backward, fingers laced in yours, and gently sat you down in the worn motel chair by the window. The fabric was cold under your bare thighs.

Sam hadn't moved. He stood like a statue at the foot of the bed, chest heaving, eyes locked on yours like he couldn't look away.

"Sit," Ruby told him, her tone turning just slightly firmer.

And he did.

She guided him down until he sat at the edge of the bed—his legs spread, boots still planted on the carpet. He looked massive, ruined, caught in the middle of something he couldn't name. His hands gripped the edge of the bed like he was afraid to touch anything.

Ruby turned back to you, lips wet, cheeks flushed.

"Watch closely, baby."

She climbed into Sam's lap in one slow, fluid motion, straddling him. His hands hovered at her sides like he was afraid to hold her. But Ruby leaned in, close to his ear, speaking words too soft for you to hear.

Then she turned her head to look at you—smiling. Like this was all a show, and you were the only audience that mattered.

"He's so worked up, poor thing," she purred. "Do you want a turn?"

Your breath caught.

"You wanna be a good girl and help us feel better?"

You nodded, your thighs clenching together on instinct.

Ruby kissed Sam then—messy and deep, her fingers in his hair. He groaned into it, hands finally finding her hips. She rocked against him once and his whole body jerked.

"Fuck," he muttered, voice shredded. "Ruby—"

She pulled back and looked at you again.

"Come here, sweet thing."

You stood on shaky legs.

"Take my place," she whispered, climbing off him slowly, deliberately, dragging her fingers down his chest. "Be good."

You moved without thinking.

Sam's eyes were wild when you stepped between his knees—dark and blown, lips parted. His hands hovered, not quite touching.

Ruby slid behind you, her arms around your waist as she guided you down—down into his lap, your knees bracketing his thighs, your breath coming short and fast.

"That's it," she whispered, lips against your ear. "Feel how hard he is for you? How much he wants you?"

You whimpered, your thighs tightening as she rocked your hips forward once—slow, grinding you down against him.

Sam's head dropped back with a groan.

"Ruby—fuck, she doesn't—"

"She wants to," Ruby said. "Don't you, baby?"

You nodded helplessly.

"Say it," Ruby coaxed. "Tell him you want to make him feel good."

Your voice was barely a breath.

"I want to make you feel good..."

Sam's hands finally touched you. Gripped your hips hard enough to bruise. His voice cracked when he said your name.

Ruby purred.

"Good girl."

You didn't mean to moan—but it slipped out anyway.

Just a soft, broken sound in the back of your throat as Ruby rocked your hips forward again, grinding you down into the thick, aching heat of Sam's cock through his jeans.

His head dropped forward, mouth brushing your collarbone. He made a noise like he was choking on the feel of you.

"Fuck, she's—Ruby, I can't—"

"You can," she whispered, wrapping her arms around you from behind. "You will. Look at her, Sammy. Look how sweet she is. So wet for you already and you haven't even touched her yet."

Your sleep shirt had ridden up to your waist, bunched just under your ribs. Sam's hands were under it now—hot and wide and shaking, gripping your hips like he was holding back an earthquake. You could feel every twitch of him beneath you, trapped behind the denim, burning through it.

You couldn't stop shaking.

"You wanna help him, don't you?" Ruby's voice was syrup in your ear. "He's been so good. He's been waiting for you. Doesn't he deserve to feel good?"

You nodded, eyes fluttering.

"Yes..."

"Say it, baby. Say I want to make Sam feel good."

Your breath hitched.

"I... I want to make Sam feel good."

Sam groaned like it hurt. His head tipped back, eyes fluttering shut, lips parted and flushed.

"Jesus Christ..."

Ruby's hands slid down your belly, fingertips just brushing the waistband of your panties. You gasped.

"That's our good girl," she whispered. "So responsive. So needy. Tell me, baby—have you ever been touched like this before?"

You whimpered. "No..."

"Mm." She kissed just behind your ear. "Even better."

Her fingers slid lower.

Sam's hands were everywhere now—your thighs, your waist, your lower back. His grip was rough, frantic, like he didn't know where to start. Like he wanted all of you at once.

"Ruby, I need—"

"I know," she said sweetly, pulling your panties to the side and slipping two fingers through the soaked heat between your thighs. "Look at her, Sam. She's dripping."

Your whole body jolted. You tried to twist away from the sensation, but Ruby only giggled and held you still.

"Shh, baby. Let us take care of you. You're doing so well."

She pulled her hand away slowly, teasing, and brought her fingers to Sam's mouth.

"Open."

He obeyed without thinking—lips parting as Ruby slid her fingers past them. He moaned low, guttural, eyes dark with something feral as he tasted you for the first time.

You made a wounded little sound, thighs trembling, head falling forward.

"Fuck—" he breathed. "She's... Ruby, she's perfect."

"I told you," she said, brushing your hair back, tucking it behind your ear like you were porcelain. "Didn't I say she'd be perfect?"

Then she leaned in again, voice like sin wrapped in silk.

"You ready for more, sweet thing?"

You couldn't speak. You just nodded. And it seemed that was all the encouragement Sam needed to shift the two of you further back onto the bed, keeping you pressed to him the entire time.

Ruby moved to sit behind you on the bed, one leg tucked under her, the other bracketing your thigh. Her hands slid up your sides, slow and soothing.

"Ride him just like that, baby," she whispered. "You're making him feel so good."

You whimpered, your hands resting on Sam's shoulders, your hips rocking in slow, helpless circles as heat curled tighter in your belly.

"You wanna keep going?" She asked, her voice dipped in honey. "Wanna make him feel even better?"

You nodded, dizzy and breathless.

"Then be a good girl and let me help you."

Her fingers slipped between your thighs again—this time not teasing. She manoeuvred you up off Sam's lap for a second, hooked her thumbs in your panties and dragged them down slowly, peeling them off and dropping them to the floor like they meant nothing.

Sam groaned beneath you, head tipping forward to rest against your chest.

"Jesus fucking Christ..."

Ruby smiled against your shoulder and whispered like a secret:

"Now ride him for real, sweet thing."

You were shaking.

Not from fear. Not exactly. But from something hot and thick curling in your belly, something too big to name. Your panties were gone, discarded on the floor like they'd never mattered. Sam was still hard beneath you, denim rough against your bare heat, and your hips were moving because Ruby told you to.

You were soaked.

You knew it. You felt it. The fabric of his jeans was sticky between your thighs and Sam was groaning, his head bowed low, sweat dampening the ends of his hair as he clutched at your waist like he might lose control.

It was too much.

"I... I don't know what to do," you whispered, voice trembling. "What do I... do?"

Ruby leaned in behind you again, her hands smoothing over your thighs, her lips brushing your ear.

"Aw, baby," she crooned. "You've really never done this before, have you?"

You swallowed hard, heart pounding.

"No..."

"Anything?" She asked softly, deceptively gentle. "Have you ever touched yourself? Let anyone else touch you?"

You flushed so hard your skin burned.

"N-no. I—I mean, not... not really..."

Ruby made a pleased little sound, like you'd just handed her the key to a locked room she'd been dying to enter.

"God, you really are perfect."

Her hands squeezed your thighs gently, her mouth warm at your jaw.

"Do you want to learn, sweet thing? Want to let us show you what feels good?"

You nodded, dazed.

"Say it."

"I... I want you to show me."

"Good girl."

Ruby kissed your shoulder, then gently—almost reverently—lifted you off of Sam's lap. He let out a breathless, broken sound, like even losing your weight made him ache. Ruby turned to him, tone shifting just enough to make it clear who was in charge here.

"Back," she said. "Now."

Sam didn't argue.

He moved further onto the bed in a slow, stiff blur, eyes glued to you like he couldn't believe this was real. His chest was rising fast, pupils blown to hell, lips parted like he might start begging. He looked like he was in pain.

You stood there, half-naked and trembling, your oversized sleep shirt hitched up high, bare legs shaking.

"Lie down, baby," Ruby said, turning her attention back to you. Her hands cupped your cheeks, her eyes glowing with soft, wicked promise. "Let us take care of you."

You obeyed.

She helped you down onto the bed, gently easing you onto your back, kissing your cheek, your jaw, your lips. You clung to her without meaning to, your fingers curling in her shirt, your legs twitching nervously.

"You're doing so good," she whispered. "You're being so brave. You'll love it, I promise. It's gonna feel so good..."

Her lips trailed lower—down your throat, between your collarbones, soft and slow. Her hands pushed your shirt up higher and higher, until your stomach was bare, your chest rising and falling like you'd run a mile.

She kissed every inch of exposed skin.

"Such soft skin... so untouched..."

Her hands slid down your thighs again—comforting, coaxing. Sam let out another choked sound, and when you looked over at him, his eyes were fixed between your legs, his hand gripping the bed like he might break it.

Ruby kissed the inside of your knee. Then your thigh. Then lower.

"Let me show you what it's supposed to feel like, sweet thing," she murmured, her breath ghosting over your heat. "You'll never want anything else after this."

You gasped when her mouth finally touched you—slow, teasing, masterful. You jolted, your hips bucking up in shock, but her hands held you down, firm but still gentle, like she'd done this before. Like she knew exactly how to unravel a girl like you.

You reached for something—anything—and Sam was there in an instant.

He crawled up beside you, his hand finding yours, his thumb brushing over your knuckles as you moaned helplessly beneath Ruby's mouth.

"You're okay," he whispered. "You're doing so good. God, you are so good..."

You turned your face into his neck, panting, whining, your thighs trembling as Ruby sucked softly on your clit, her tongue drawing slow, filthy circles that made your whole body clench.

"Let go, baby," she whispered between licks. "Be our good girl and come for us."

Your first orgasm broke over you like something sacred.

One second you were gasping into Sam's neck, Ruby's mouth still moving between your thighs, and the next—your back arched, a sob tore from your throat, and your whole body shuddered like you'd been struck by lightning.

It wasn't sharp—it was overwhelming. Full-body. Wringing you out like wet cloth. Sam held your hand tighter, whispering praise that barely landed, and Ruby moaned against your cunt like she felt it, like your release was something for her.

"God, baby," she breathed, and then—she slipped a finger inside you, slow and deliberate.

You jolted, a strangled cry slipping out as aftershocks tore through you. Sam's grip on your hand went white-knuckled.

Ruby moaned.

"She's so warm, Sam," she said, voice thick, dreamy. "So wet. You have no idea."

You whined, writhing, but Ruby only kissed your thigh like a reward and pulled her finger out—slick, shining.

"You're such a good girl for us," she whispered. "That was so beautiful."

She crawled back up your body, her skin hot against yours, and kissed your lips again. Deep, slow, tasting like you.

"Sam," she purred between kisses, her voice dipped in smoke. "You have to try this."

Sam didn't speak.

He just grabbed her—hard. One hand in her hair, the other on her hip, yanking her off you with a roughness that made your breath catch. He crushed his mouth to hers in a brutal kiss—desperate, consuming—and then shoved her aside like she was nothing more than a gatekeeper to his altar.

His altar being you.

He dropped between your legs without a word, spreading you open with shaking hands, and dove in like a man starved.

You screamed.

It was too much. Still trembling from your first orgasm, your body overloaded, you cried out as his tongue dragged through your folds, moaning against you like he was fucking possessed. And maybe he was. His grip on your thighs was bruising, his mouth unrelenting.

"Oh my god—S-Sam—!"

You tried to close your legs on instinct, but he just growled—growled—and shoved them wider, burying his face deeper.

"That's it," Ruby whispered, curling up beside you again. Her fingers found your hair, stroking it gently, brushing it behind your ears with all the tenderness of a mother tucking in her child. "Let him ruin you, baby. You're being so perfect."

You whimpered, face twisting into something close to pain.

"It's too much..."

"Shhh." Her hand cupped your cheek. "That's what makes it good."

Sam groaned between your thighs, low and wrecked. His tongue moved faster, deeper, insistent, like he couldn't get enough. Like he wanted to crawl inside you and stay.

"You feel that, sweet thing?" Ruby murmured, her mouth close to yours. "That's what happens when you give yourself over."

She kissed you again—languid, possessive, one hand still petting you like you were something to soothe and subdue.

"Open your mouth for me," she whispered. "You're drooling. It's cute."

You blinked, dazed, lips parting as her thumb pressed to your jaw.

"Let me feel it."

You obeyed.

She kissed you again, deeper this time, tongue slick against yours, swallowing your moans and the helpless sounds you made as Sam devoured you like he'd die if he stopped.

"That's it," she said softly. "Drool in my mouth, baby. You're doing so good."

She turned her head slightly, speaking to Sam like you weren't even there.

"She's so sensitive. Barely came once and look at her—already shaking for you."

Sam just groaned in response, too lost to speak. His hands gripped your thighs tighter, his tongue relentless, and you broke again with a sharp cry into Ruby's mouth.

You couldn't stop crying. Your legs wouldn't stop trembling, your voice had gone hoarse from moaning, and Sam was still between your thighs, tongue moving like he didn't hear you—like he didn't care.

"S-Sam—p-please—" Your fingers twisted in the sheets, your hips jerking, but his arms locked you down. "I—I c-can't—!"

Ruby was still beside you, still stroking your hair like nothing was wrong.

"Sam," she said softly. "Baby, she's crying."

He didn't stop.

He growled against you—low and guttural—and sucked harder, dragging his tongue with filthy, practiced strokes that had your spine arching, tears streaking your cheeks.

"Do you need him to stop, sweet thing?" Ruby whispered, brushing her thumb over your wet lashes.

You sobbed. Nodded.

"Y-yes—please—I c-can't take anymore—"

"Aww," she cooed, her voice like poisoned honey. "My poor baby. You're so sensitive. So perfect for him."

You gasped when Sam gripped your thighs tighter—his fingertips digging in, holding you wide open as his mouth moved faster, chasing another orgasm like he was possessed.

Ruby leaned in closer, her voice dipped in false sympathy.

"If he stops now..." she said sweetly, "...he's going to be so unsatisfied. That wouldn't be fair to him, would it?"

You blinked, dazed and wrecked, chest heaving.

"W-what...?"

"He's been waiting for you for so long, baby," she continued, stroking your cheek. "He's so hard it hurts. If you really want him to stop, you're gonna have to give him something."

You whimpered, nodding blindly.

"Anything, please—j-just make him stop—"

Ruby smiled like the devil in silk.

"Then you'll let him fuck you, sweet thing?" She kissed your temple. "You'll let him put his cock in that sweet little pussy and use you the way he needs to?"

Your lips trembled. You were crying so hard now it didn't feel real. But you nodded again. You couldn't think past the overstimulation—just needed him out from between your legs, needed something to change.

"Yes—yes, please—please—just make him stop—"

Ruby sat up, her voice turning firm.

"Sam. Stop."

He didn't move.

"Sam."

He growled—growled, full-bodied, vibrating the bed. His eyes were black, mouth wet, breath ragged.

"Don't—don't fucking tell me to stop—"

Ruby laughed.

"You'll thank me in thirty seconds, big boy."

She shoved him back by the shoulder, and this time—barely—he let her. He knelt between your legs, panting, pupils swallowing the green of his eyes.

Ruby leaned over you again, her hands spreading your legs wider.

"You're gonna take him now," she whispered. "You're gonna let him fuck you like he's been dreaming about for weeks. And you're gonna thank him for it."

You sobbed. Nodded.

Sam's hands fumbled with his jeans, dragging them down far enough to free his cock—thick, flushed, angry red with need. He didn't say a word. He just looked at you, hair in his face, jaw clenched, chest heaving.

"She said yes, Sammy," Ruby whispered. "She wants it. She wants you."

Sam moved fast.

He grabbed your hips, yanked you down the bed, and pressed the blunt head of his cock to your slick entrance. You gasped, eyes wide, every nerve ending screaming.

"You ready, sweet thing?" Ruby murmured, mouth at your ear. "You ready to be his?"

You whispered it, broken.

"Yes..."

Then Sam sank into you in one brutal thrust, and the sound you made wasn't human.

Your back arched, your breath vanished, and your body clenched around him like it didn't know how to take it. He was thick, hot, impossibly deep—and still moving, dragging out slowly, then slamming back in so hard the headboard rattled against the wall.

"Fuck—fuck— you feel unreal," he groaned, eyes squeezed shut, his voice wrecked. "So fucking tight—shit, baby, you were made for me—"

You cried out, hands grasping at the sheets, your body already fried and raw from overstimulation. Every thrust felt like lightning—too much, too deep, too good.

"You okay, baby?" Ruby murmured beside you, her voice sweet and syrupy. "You still with us?"

You nodded through the sob that escaped you, and she smiled like you'd just done something precious.

"That's my girl."

Sam fucked into you harder—hard enough to make the bed creak, his grip bruising on your hips. He looked elated, lost in it, mouth open as he moaned through gritted teeth.

"So fucking pretty when you cry," he panted. "Look at you—look what you're giving me—fuck—"

Ruby slid closer, still fully clothed, lips ghosting your temple.

"She's drooling again," she said with a laugh, her tone sing-song and amused. "You love this too much, sweet thing. Can't even keep your mouth closed."

You whimpered, your thighs shaking, and she kissed your cheek sweetly.

"That's okay," she whispered. "We love how messy you are."

Her hand slipped beneath her waistband, fingers curling—and then she took your trembling wrist and guided it down with her.

"Here," she murmured. "You wanna be good for me? Touch me."

Your fingers slipped beneath the lace, and you gasped when you felt how wet she was—soaked, hot, throbbing against your hand. She moaned low in your ear.

"That's it," she breathed. "Let me show you..."

Her hand wrapped around yours, using you, grinding down onto your fingers as Sam fucked you open in deep, brutal strokes that made your stomach tighten and your vision blur.

"Move in little circles," Ruby whispered, guiding your fingers. "Mmm—just like that, baby. You're such a fast learner."

Sam was losing it.

"She's touching you?" He groaned, looking down at you both, sweat dripping from his hairline. "Fuck, Ruby, fuck— she's so perfect—"

"She's everything," Ruby said with a soft moan, pressing your fingers harder. "She's ours now. Look at her. Look at what she's letting us do."

You choked on a sob, your hand trapped between Ruby's thighs, your body jerking with every thrust of Sam's cock. He was panting now, animalistic, his hands sliding up under your shirt to grope at your breasts, dragging his thumbs over your nipples.

"You hear that, baby?" Ruby crooned. "Hear how wet you are? How wet I am? It's all for you."

"You feel so good—so fucking good—" Sam growled, his thrusts speeding up, sloppy and deep. "I'm never gonna stop—never—never letting you go—"

Ruby grabbed your jaw, turned your face toward her, and kissed you like she owned you—tongue pushing into your mouth, swallowing your sobs and your moans, your drool and desperation.

"Open for me, sweet thing," she whispered against your lips. "Let me taste how wrecked you are."

You obeyed. You always obeyed. And as she kissed you, she didn't hold back, drool leaking into your mouth, sliding down your throat like a living thing. Warm. Sweet.

And Sam? Sam was losing it.

Sweat dripped from his chest, his arms were trembling from how hard he held himself above you, and his thrusts—fuck—they were frantic now, so deep and fast it felt like your body couldn't keep up. You couldn't breathe. Couldn't think. He was babbling between moans, his voice cracked open, wrecked.

"Can't believe this is real—fuck, you feel like heaven—so tight, so fucking warm—squeezing me, baby, you're fucking—you were made for this—"

Your legs were jelly around his hips. Your voice was gone, reduced to broken gasps and whines as his cock hit that deep spot again and again, the bed groaning under every thrust. Your hand was still between Ruby's thighs, her slick soaking your fingers, and she was rolling her hips against them slowly, deliberately.

"That's it, sweet thing," Ruby purred, her voice so gentle it made your eyes sting. "Let me use that precious little hand. You're such a good girl for us, letting us fuck you just right."

She leaned over you again, brushing your sweaty hair behind your ears, thumbing your jaw open.

"You want something in that mouth, baby?" She whispered sweetly. "You want me to spit in it again?"

You nodded—desperate, dazed, ruined.

She smiled.

"Open up."

She let it hang between her lips for just a second before letting it fall—hot, thick, landing on your tongue like sin. You moaned, tongue twitching, and she cooed.

"Swallow it like a good girl."

You did.

Sam groaned like he might fucking die.

"She's letting you spit in her mouth?" He gasped. "Jesus— fuck, I'm not gonna last—she's so—"

"She wants it, baby," Ruby crooned. "Don't you, sweet thing? You love how good you make him feel?"

You nodded, sobbing.

"Mhmm—yes—yes please—feels so good—!"

Ruby's hand slid between your legs again—while Sam was still fucking you—and her thumb found your clit with perfect, devastating pressure. You screamed, body jerking violently as she circled it with soft, expert cruelty.

"That's it," she whispered. "Let me help you break."

Sam was gone. Gone.

"Gonna fill you up, baby," he grunted, thrusts getting rougher, more erratic. "You're gonna take it, right? Let me come inside that pretty little cunt?"

"She wants it," Ruby said, matter-of-fact. "She's mine now. She'll take anything I give her. Won't you, baby?"

You cried out, stars bursting behind your eyes, your fingers slipping deeper into Ruby as her hand guided you.

"Fuck me with them," she murmured, voice like velvet-dipped knives. "Make me come while Sammy fucks you full."

You whimpered, your fingers pumping helplessly into her dripping heat as her thumb rubbed cruel circles into your clit, Sam's cock still slamming deep inside, faster, harder—

"You're mine—ours—fuck, I'm gonna—baby—take it—"

You shattered.

Your body convulsed, the scream caught in your throat, legs kicking uselessly as the orgasm ripped through you like nothing had ever existed before it. Sam groaned so loud it echoed off the walls—and then spilled inside you, hips jerking, cock twitching as he filled you up, panting, gasping, babbling your name and Ruby's in a filthy prayer.

Ruby came on your fingers a moment later, moaning low, hand never stopping on your clit as you sobbed through the comedown—wrecked, full, ruined.

"There you go," she whispered. "That's it, baby. That's my perfect little thing."

She kissed you once, slow and sweet.

"You're never leaving this bed again."

You didn't remember when you stopped crying. Somewhere between Sam's moans and Ruby's mouth, your tears had dried—leaving only heat, and ache, and the tremble in your thighs as you lay between them.

You were sore. Sticky. Wrecked in a way that felt permanent.

But you didn't want to move.

You could still feel Sam's spend leaking out of you, warm and slow. Ruby's breath was soft against your cheek, her fingers still tangled with yours like they had every right to be. Sam's hand rested over your belly—heavy, protective, possessive.

You felt claimed. Worshipped. Ruined.

You stared up at the ceiling, breath ragged, thoughts flickering like static, and it settled in your chest like truth:

You weren't yours anymore.

You didn't know when it had happened—when your body stopped being yours, when your heart shifted, when your innocence dissolved between their hands.

You just knew that it had.

And maybe that should have scared you. Maybe, once, it would have.

But lying there, between them—used, owned, kept—all you felt was peace. Because here, in this bed, you belonged to them. And you weren't sure you ever wanted to leave.

“You know you could’ve just asked if you wanted to borrow my clothes, sweetheart,” he teased, which earned him a playful smack on the chest.

“You weren’t complaining earlier,” you puffed. “And while we’re on the topic: You could’ve just asked if you wanted to try the pumpkin spice latte.”

Neon paints your body in hues of red and blue as you cross the dance floor. The dive bar has little by way of illumination beyond the signs on the wall depicting beer and food, half-naked cowgirls, and the name of the joint. A few yellowed lights hang from the ceiling, joining the bright colors to shine down on the crowd below.

You wind your way through the throng of sweaty bodies, their boisterous conversations meld with the thrum of music soaking into the atmosphere. Cold glass bites into your palm as you carry your fresh beer back to the edge of the dance floor. 

It’s standing room only— a regular occurrence on Thursday nights where ladies drink free— and since your friends have long since returned home, you don’t see the point in trying to snag a high-top for yourself. 

No, half drunk on the music and the cheap beer, you don’t want to sit–you want to dance.

Between line dances, you down long-necks and tall glasses of water alike, feeling like you’re sweating it out faster than you can consume; the last thing you want is to wake up in the morning with a splitting headache, even if your freelance job awarded you a day off. 

After being contained to your apartment by the threat of being ripped to shreds at the razor-sharp claws of a pack of supernatural beasts, you want to spend your new lease on life as you pleased, and right now, you are doing just that. 

You’ve lost count of how many dances you’ve finished by the time your bladder begs you to vacate the floor and empty it. Reluctantly, you shuffle off the dance floor, having to only wait behind three other girls before you snag an open stall. 

The bathroom itself leaves something to be desired. Dingy tile line the floors; you aren’t sure if the patterns were actually design choices or were poorly cleaned stains. Raunchy love notes cozy up to random phone numbers with instructions to ‘call for a good time’ with crude pictures of dicks on the cheap stall walls and door. 

Noting the bathroom was empty, you finish up and wash your hands, smiling at the additional graffiti etched into the edges of the dirty mirrors. Most of it is hazy anyway, the blanket of alcohol warming you at the edges. You pull your tube of lipstick from the pocket of your miniskirt, the denim barely covering you enough to avoid a public indecency charge.

You don’t think much of it when the music grows louder, too busy shoving the lipstick back into your pocket. The door to the bathroom creaks open before it shuts hard with a thud, muting the sounds once more.

It isn’t until you hear the snick of the lock sliding into place that you look up to see a figure standing behind you in the reflection of the mirror. Your heart drops to your stomach in the same second your pussy throbs violently when you whirl around to familiar green eyes that blink black before returning to their alluring jade. 

“Hiya, Sweetheart,” Dean purrs, stepping closer so that there’s less than a foot of space between your bodies. “Forget what day it is?”

Your boots have a bit of a heel, so there’s less of a height difference than the first time he visited you. Usually, you’re at home. Most of the time you’re already in bed when he arrives, sometimes in the shower, sometimes making food.

“No. Just lost track of time.” Somewhere between the dancing and the drinks and your phone being tucked away in the purse you’d brought, the time had slipped away.

His head cocks to the side, the move more animalistic than human. “That so?”

“I wanted a night out with my friends. Sue me.”

His eyebrows raise but he says nothing. 

Not right away at least. 

Instead his attention drifts from your face, slipping down your body. 

You can see his eyes catch on your strappy tank top where the halter neckline plunges to near obscene levels, showing off the scalloped lace of your bra. The green in his gaze goes dark in a different way than you are used to the further down it travels, down all the way to the bare expanse of your legs and where your boots sit upon your feet.

“Must’a had every guy in here tonight drooling over you,” Dean says appreciatively, eyes flicking back up to yours. 

You brace your hands on the sink behind you and lean back with a shrug, trying to act casual and not like your pussy isn’t growing wetter by the second. The heat that rises to your cheeks is in humiliation. He hasn’t even touched you yet and here you are like a bitch in heat.

You’d noticed the heated stares, the way some of the men in the bar’s eyes would pop out of their skull like some cartoon, and you’d be lying to him and to yourself if you said you didn’t revel in it. 

He leans in, and you’re not sure when he got this close to you but you’re assaulted with the intoxicating smell of him. Something masculine and dark that makes you want to bury your face in the crook of his neck. 

You jump a little when the warmth of his palm spreads along the inside of your thigh, too entranced by his gaze, heavy and focused, to notice his arm slipping between your bodies until it’s there. His fingers tease along the soft skin, the tips just inches from the throbbing need between your thighs. 

“Too bad your pussy’s already got someone takin’ care a’her, right?” He croons, slipping his hand up. 

Words escape you as he slides your panties to the side, not that the lacy scrap of fabric was covering much to begin with. 

Your mouth gapes open at the first teasing touch, the calloused tips of his fingers sliding through your slick, bumping against your clit. Hands gripping the edge of the sink so hard you’re sure the porcelain will crack any second, your hips buck up against his hand, seeking the stimulation.

The sense of euphoria is short lived when his other hand shoots out, wrapping around your neck. A gasp gets stuck in your throat and your eyes flare wide. His fingerprints dent your skin.

“Right?” He asks again with a darker edge this time. 

The bathroom around you narrows to the tightness of his grip on your neck and the pleasure derived from his fingers still working over your soaking core. Every inch of your body erupts in tingles, and you would have nodded if his hold allowed it. 

“Yes,” is all you manage to choke out. 

It is a funny feeling. Dean quite literally has your life in his hand. By all accounts you should be pissing-yourself-terrified. But you’re not. Instead, all you can focus on is the dark whorls of lust eddying in the depths of his eyes, the green heightened with his enjoyment, and how his middle finger is circling your clit with precision. 

That was, until it retreats and you nearly whine at the loss of contact. 

You sense where his hand is going milliseconds before his open palm makes contact with the side of your face. It’s not hard enough to do any damage beyond a buzzing beneath your skin that will last probably as long as this encounter, but it’s hard enough for tears to sting at your eyes. 

“Yes,” you wheeze, his grip on your throat just loose enough for the words to squeeze out. “My pussy’s yours.”

Another slap, this one no less gentle than the first. “Say it again.”

Your hand slips up, wrapping around his wrist. “My pussy’s yours.”

His pulse is even under your frantic grip. If it weren’t for the desire written in his gaze and the sizable bulge straining against the front of his jeans, you wouldn’t have guessed he was enjoying this. You’re painfully aware of arousal dripping down your inner thigh, your core clenching around nothing.

Dean’s hand connects with the side of your face one last time then returns between your thighs. The edges of your vision start to go fuzzy, and the moan he pulls from your lips when his fingers press harshly against your clit comes out more like a high pitched keen.

He leans in, keeping steady pressure on your neck. “You’re gonna cum for me before I let you go. Can you do that for me, whore? Not like you need to breathe, anyway.”

“Yes,” you choke out, voice a little louder than a whisper.

“Yes what?” Dean asks teasingly, his fingers moving across your core in a way that makes it really hard to formulate words. 

“Yes, sir.” Your words are slurred, but they seem to suffice anyway as his hand picks up the pace. 

Your hips grind against his palm, matching the rhythm he’d created. You feel dazed when his hand slips lower, two fingers shoving inside you while the heel of his palm acts as the perfect surface to grind your clit on. 

He doesn’t seem to notice or care when your nails dig into the inside of his wrist, your other clawing at his shoulder to brace yourself against the rapidly growing wave of pleasure stemming from between your thighs. 

His muscles shift under your grip as he angles his arm better so he can send his middle and ring finger even deeper into you, curling them up towards your belly. Your hips grind down against his hand, the rough surface providing the most divine friction against your needy clit.

An amused chuckle from Dean vibrates through your body. “I can feel your pussy clenching around my fingers. Fuck, I can’t wait to feel ‘er around my cock.”

A strangled whine is all you can muster as he curls his fingers inside you, stroking that soft spot within you that darkens your vision even further. Arching your back, you press your chest into Dean’s, his preternatural warmth soaking into you. 

You’re sure he can feel the way your nipples are hardened, even through both your shirts. The bralette underneath is little more than decorative lace with a paper thin backing there to not irritate your skin. 

His blood-red button down is immaculate, tucked into a pair of dark wash jeans; it’s similar to the outfit he wore the first time you met him.

Well, he’s nothing if not consistent, you think before stars burst behind your eyes, which you squeeze shut as the tightness in your belly gives way. 

You cum harder than the first time he fucked you. Harder than you ever have in your life. 

Your body goes rigid, trembling from head to toe as electric shocks spark through you all down your spine. The ache of pleasure pulses through your body as he works you through the throes of your climax. 

Head lolling to the side as Dean’s grip on your neck lessens, you gasp in air. The room around you spins as you gulp down oxygen the best you can through your unabashed moans.

Dean’s lips slot over yours, drowning out your sounds of ecstasy and you can taste the whiskey on his tongue when it sweeps into your mouth. Your hand slides up his shoulder to the back of his neck, fingers tangling in the shaggy ends as you kiss him back with matching intensity. A low rumble of satisfaction emanates from his chest.

As you slowly come back into your body, Dean’s hand slows, his fingers leisurely dragging out of you and stroking your oversensitive clit on their way out from between your trembling legs. He grips your chin none too gently, breaking the kiss. 

There isn’t enough time for you to miss the feeling of his lips on yours, to savor the tingling he left behind, before his fingers are in your mouth. 

The calloused tips press down your tongue and instinctively you wrap your lips around the second knuckle. You can taste yourself as you work them over with your tongue, your whimper turning into a gag when Dean shoves his fingers deeper into your mouth.

“That’s right,” Dean all but purrs, looking on with a lust-drunk expression. “How are you gonna take my cock if you can’t take two little fingers?”

He’s right, you think, but I wouldn’t call his fingers small, either.

His grip on your chin relaxes just enough for you to work your jaw open more. Viscous saliva floods your mouth as Dean moves his fingers in and out of your mouth. Every time he bottoms them out, you cough and gag as the tips wiggle against the back of your throat. 

Tears sting your eyes, spilling down your cheeks in fat droplets when you blink up at him. There’s a hungry edge to the way he gazes down at you, obsession bleeding in as he fixates on how your spit collects on his knuckles and rolls down his hand. 

Another rush of want crashes over you at the way he’s looking at you and in response, your thighs clench together unconsciously. The miniscule movement isn’t missed by Dean, not that you were really trying to hide your insatiable need anyway. 

“God, you’re such a greedy slut,” he groans. “I just got you off and you’re already wanting more, aren’t ‘cha, Sweetheart?”

With his fingers shoved into your mouth, all you can do is hum in agreement. 

Dean hums his approval, and with the slightest nod his fingers slip from your mouth, the hand on your jaw following suit. You suck air in greedily, the strings of drool starting to cool on your chin. 

With eyes half-lidded out of pure lust, you watch him raise the hand pulled from your mouth up to his own. A particularly strong pulse of arousal nearly sends you to the floor as his tongue darts out from between his lips. The sounds that come from him slurping your spit from his hand are purely pornographic, all while he keeps his eyes locked on yours.

“Knees. Now,” he commands, wiping the mix of your spit on his jeans.

With how shaky your knees have become in the aftermath of his display— as well as the leg-shaking orgasm he gave you— you’re tempted to comply. A glance down to the bulge in his pants is enough for saliva to pool under your tongue, but the alcohol in your system has made you bold. 

“And if I don’t want to?”

His head cocks to the side, eyebrows quirked up. “No?”

A shake of your head as you look up at him through your lashes. “No.”

“You don’t want me?” He asks, his hand curling around your wrist, bringing your palm to rest on the evidence of his arousal. “You don’t want my cock?”

His grip disappears, but you press the heel of your palm against him, dragging your hand along the length of him. “No, I don’t.”

Dean gives you a knowing smirk, and the moment stretches wide between you before he finally speaks. 

“Liar.”

His hand moves too fast for you to react, fingers tangling painfully in your hair as he grabs a fistful. 

You cry out softly, half from the pain and half out of shock. He leans forward and the sound dies out into a quiet gasp. Your eyes dart from the depths of his gaze to his lips, which are still tugged upwards in a satisfied grin, and back again. 

“You want me. I’ve been inside you. Tasted you.” His thumb traces the plush of your bottom lip, smearing your lipstick even further. “I know just how desperate you are for my cock, whore. You can’t ever pretend otherwise.”

Your knees make contact with the grimy bathroom floor and you can feel yourself tremble with anticipation as Dean angles your head to look up at him. 

“Keep your eyes on me,” he says, undoing his belt with his free hand.

“And if I don’t?” You ask before you can think better of it. 

Dean doesn’t even bother to shove his jeans and boxers down his muscular thighs. They barely make it down past his balls before he’s languidly stroking himself, the tip red and already leaking. 

Your throat bobs and you barely flinch when he grips himself at the base and slaps his heavy cock against your cheek. 

“Oh, Sweetheart. Don’t make me ask twice,” he says.

Heart beating a million miles a minute, you barely feel the small sting of contact nor the dull ache of the tight grip he has on your hair. Your world is narrowed to the throbbing need in your pussy and Dean’s hard cock bobbing in front of you. 

“Now don’t be difficult and open your fucking mouth,” he growls, shoving his cock towards your mouth. 

You have the good sense this time to obey, your lips parting without hesitation. Tongue lolling out, you barely have enough time to situate yourself before his cock is halfway down your throat. 

Instantly, your throat is on fire and you gag at the sudden intrusion. Hands flying up to brace against his denim clad thighs, you brace yourself as Dean holds your head in place.

“Fuuuck,” he rasps, dragging his hips back and briefly allowing you to breathe. “I missed this. Had a lotta girls, but none of their mouths feel half as good as yours does.”

It takes a second for you to adjust to how he’s stuffed into your mouth. Drool has already started to leak out of the sides of your mouth with every thrust of his hips. The stretch of your lips, the taste of him is just right. He smells warm, like sweat and skin and some clean, masculine soap.

And it’s pathetic the way you silently enjoy him pressing your face further onto his cock until your nose is buried in the thick, curly hair at his pubic bone. Your throat spasms as he holds you there, unable to breathe and frozen with sensory overload. 

Hot tears crawl down your cheeks, blending with your drool on your chin. Just when the edges of your vision start to blur, Dean yanks you off his cock by your hair. You cough and sputter, replenishing the void of oxygen in your lungs. 

Thick strings of drool stick to your chin and neck, and you just know your mascara is running down your cheeks, half-dried to your skin with your tears.

“Such a messy girl,” he coos, honey-laced words dripping with condescension. “See, all you needed was a good dick in that brat mouth.”

You welcome the sting as his hand leaves another hot print on your cheek and you have to resist from leaning into his palm when it caresses the hurt. It slips away just as quickly, and in turn you wrap a hand around the spick-slick shaft of him. 

“Gonna keep fucking my face, or do you want me to make it actually feel good?” You ask, locked on his eyes as your mouth closes around the head of him. 

The groan Dean utters when your cheeks cave around him, when your tongue slides along the sensitive underside of his cock, is all the answer you really need. 

You’d learned early enough on that you really had to squeeze your hand around his cock when stroking him. “Harder, bitch,” he’d growled. “Don’t be fucking scared. You’re not gonna break it.” 

His fingers still threaded themselves in your hair, the tips gliding across your scalp as you descended back down upon him. His head falls back, and the red ambient lighting in the bathroom gleams along the column of his throat, skin dewy with sweat.

You’d like nothing more than to stand and lick the salt from his skin. 

Tongue pressed to the underside and cheeks hollowed, you slide his cock all the way to the back of your throat. Your gag reflex balks, but you ignore it, pulling back barely half way before bobbing your head back down. The small whimpers and moans that you make no attempt to stifle travel along his cock. 

Dean’s hand curls further into your hair, leaving your head littered with sharp pinpricks. All it does is add to the slickness between your thighs. Thighs that you press together seeking any kind of friction; you can feel your arousal roll down the insides. Your skirt is still hiked up around your hips, leaving your dripping pussy exposed to the cool air. 

A dull ache makes itself known in your knees, the bathroom tile extremely unforgiving on the joints. You do your best to ignore it, hand sticky with spit abandoning his shaft in favor of cupping his balls. 

Dean’s hips buck into your mouth at the additional touch, seeking the wet heat. 

“Oh fuck,” he grunts. “Keep doing that.”

So you do, fondling him there while maintaining your rhythm; push your head down on him until you can feel him in your throat— until you gag harshly— then pull back enough to breathe through the spasm. Rinse and repeat all the while your free hand inches closer to your throbbing pussy. The wet, sloppy sounds from your mouth meld with his decadent grunts and groans, filling the bathroom. 

The system works, up until the point it doesn’t.

You come up for air only for Dean’s hand to press against the back of your head, pushing you back down onto his cock. Your eyes screw shut as your nose is mashed into the mess of curls at his pubic bone. 

A sound of displeasure vibrates from your lips up the length of him, and after a second you try and pull your head back. It ends fruitlessly, though, as Dean only presses harder. 

“Shut up. Just a little longer,” he growls. “Fucking take this cock. Fucking choke on it like the whore you are.”

Your tear-filled eyes screw shut as your throat spasms hard. Bracing a hand on his muscular thigh, your fingernails dig into the denim. Dean’s cock moves, barely pulling out an inch before it’s back, harshly slamming into your throat. A soreness grows in your jaw for how long you’ve kept it open.

“Fuck, that’s it,” he moans, his chest heaving. “Gonna fucking cum, baby.”

That fuzzy, floaty feeling returns as you struggle against the need to breathe, against the intrusion of cock in your throat. He starts to twitch against your tongue, and the pistoning of his hips grows sloppy and uneven. Pushing through the haze, you swallow around him, earning yourself a string of curses from above you. 

The crass words are cut off by a garbled moan. You hear your name somewhere in there, but you’re too busy swallowing down Dean’s cum to pay much attention to what he’s saying. He holds you there, cock pumping his seed down your throat until he stops twitching and his length softens a bit. 

Lines of spit connect your lips to his cock once he finally wrenches himself from your mouth, and they snap back against your chin when he takes a step back. Your body is wracked with wet coughs as you gasp for air. Heart beating what seems like a million beats a second, you lean back on your heels and wipe the spit from your face.

Out of the corner of your eye you see Dean tuck his half-flaccid cock back into his boxers, leaving the jeans unbuttoned. 

“Up,” he rasps, still breathing hard from his climax. 

On shaky legs, you rise up, wincing at the stiffness in your knees. You brace a hand on the sink behind you as the feeling returns to your lower extremities. 

Dean’s hand slips around to the nape of your neck, drawing you in. His lips capture yours before your brain can catch up. He licks into your mouth and you whimper when his leg slots between yours. The top of his thigh bumps against your neglected core and you nearly cry at the sensation. 

“I can fucking feel you soaking through my jeans, baby,” he says, sliding both hands to your hips. “Soaked just from sucking cock, just like a proper whore.”

Your brain buffers, overloaded with the repeated deprivation of oxygen and the way the roughness of denim feels against your needy clit, your panties still pulled to the side. All that leaks out of you is a pathetic whimper that’s mostly intelligible.

Dean laughs cruelly, kissing a line of fire down your jawline. “So dumb, baby, and you haven’t even had my cock yet.”

He bounces his thigh against you and you cry out, hands scrambling to find purchase on his broad shoulders. 

“Please,” you manage to whine. 

“Please what?” His teeth graze the line where your jaw meets your neck. 

“Need’a cum. Please.”

“You think you deserve it?”

“Mhmm,” you nod vigorously. “Please, Dean.”

You can feel the wet spot your soaked pussy has made, now. The dampness of the fabric allows you to slide easier along the rigidness, your movements barely a fraction of what you need. 

“You think you can make yourself cum on just my thigh?” He pulls back from your neck, an amused tilt to his lips. “Gonna hump my leg like the dog you are?”

“Please,” you say barely above a whisper, legs trembling again.

“I’m not gonna help you. Gonna have to be a big girl and do it all yourself.”

“That’s okay, it’s okay. I can do it. Please, please,” you babble nonsensically now, much to his sadistic satisfaction.

“Better get on with it then,” he says. 

No sooner are the words spoken into existence are your hips grinding down against his thigh. You feel him flex his quad beneath you, creating a ridge that feels mind-numbingly good against your clit. 

You cling to his shoulders for stability, wanton moans spilling from your lips unimpeded. It takes less than a minute for a tightness to grow low in your belly. The heat from his body, the smell of him, it all wraps around you and soaks into your veins like an aphrodisiac. 

There’s no sane part of you left to care how humiliating this is, how desperate you are to dry hump his thigh just from having a dick down your throat. Everything in you is narrowed down to how good dragging your pussy along his thigh feels. How with every shift of your hips, sparks of pleasure threaten to set you alight. 

“Such a dirty girl,” Dean croons in your ear as you puff out breathy moans. “So goddamn pathetic it’s almost sad.”

Your pussy clenches on nothing at the words, at the names he’s calling you. You bury your face in the crook of his neck, hiding the way your cheeks warm. The scent of him is stronger here, and you inhale deeply. 

Dean’s hands have moved to the sink directly behind you, his body effectively caging you between the solidness of his torso and the cool porcelain. It’s that fact alone that keeps you mostly upright, your legs shaking. It grows worse with each drag of your pussy along his thigh, pressure building between your legs. 

“I can feel you shaking, you close?” Dean’s words rumble through you. 

You nod against his neck, moaning into his skin like you can imbue your need to cum into his system. You squirm and hump against him, mouth falling open as you rapidly approach the edge of your orgasm. It’s so close, the final build up making your movements erratic as you push yourself just that little bit further. 

But just as you are about to tip over the edge, Dean pulls his thigh from between your legs and steps back enough you have to reach behind you to keep yourself from collapsing to the ground. 

“No!” You cry out, very nearly at the verge of tears. “Wha—what the fuck?!”

Dean chuckles darkly, meeting your frustrated gaze. “Did you really think it was going to be that easy? God, you’re dumb.”

“Fuck you,” you spit at him. 

“All in good time, baby. Now turn around, put your hands on the sink.”

You scowl and instead you reach down, tugging your skirt back over what little it covers before crossing your arms over your chest. “No.”

Dean’s head tilts and he pouts his lip mockingly. “No? Gonna throw a little tantrum now?”

“Fuck. You.” You say again. 

“You’re really gonna try this with me?”

He’s stepped closer again, so if you really did want to go anywhere, you’d have to push past him. 

But you don’t, and he knows it. 

It’s all part of the game. You play it up, act like you don’t want him, just so that he’ll snap and manhandle you into whatever way he wants you. The best part about it is, he wants to fuck you just as much, so no matter how much you brat, how much you pretend, you’ll end up with his cock shoved into you anyway. 

It’s a welcome change to all the hook-ups you’d had before. Men— boys, really— who would give up at the slightest bit of pushback, who’d pussy out at the level of roughness you so desperately craved. 

And that’s why, even though Dean popped up once a month to rock your world and leave you sated, you never felt the need to indulge the men like the ones who’d been at the bar tonight. They could never satisfy you in the same way. 

“Turn around, and put your hands on the sink,” he instructs again, both of you knowing you won’t before the words even leave his mouth. 

You stand taller, looking him straight on. “Make me.”

You can see the instant his resolve snaps. Something in his face twitches and his expression darks the millisecond before his hands grasp onto your hips roughly. A gasp makes its way out of you when you’re spun around and shoved roughly into the sink. 

The edge digs into your stomach, but that’s the last thing you’re paying attention to when Dean kicks your legs apart with his boot. His hand presses into the middle of your spine, pressing your upper half forward so you are half laying across the sink. 

Looking up, you are met with your reflection for the first time since Dean walked into the bathroom. 

You were right to assume you looked absolutely wrecked. Mascara is streaked down your face, your red lipstick smeared across your kiss-swollen lips. Then your eyes cant up and you catch Dean staring, but not at your face. His eyes, pupils blown so wide you can barely see his green irises, are trained lower. 

Bent over like this, your skirt rides up an obscene amount, baring your panty-clad pussy to him. His lower lip is caught in between his teeth, and he almost looks contemplative in his admiration. 

“Gonna keep staring or are you gonna do something?” You snark, watching his eyes snap up to yours in the mirror. 

“And what are you gonna do if I don’t?” He asks in turn. “What if I just make you stand like this and let all those guys out there who were eye-fucking you come in here and take their turn?”

Your pussy clenches at the thought, and even though Dean no doubt caught the motion, he makes no comment. 

“You wouldn’t. You’re too fucking possessive,” you respond, calling his bluff with not a bit of confidence in your statement. 

Dean smiles, and it’s not a kind expression.

Warm skin against the backs of your thighs makes you flinch a bit, even though you can see him take a step forward. His hands slide your skirt back over the swell of your ass, bunching the fabric around your waist. 

“Maybe, maybe not,” he muses, slipping his fingers beneath the waistband of your panties. “Maybe when I’m all done with you here they can fuck you while my cum’s still leaking out of you.”

Cool air meets your soaked core as Dean drags your panties down your thighs, down your legs. His fingertips skate your skin as he lifts your feet, removing the scrap of fabric completely. Your mouth twists in a fleeting moment of disappointment when he shoves them into his back pocket. 

Those were my favorite pair. 

“Either way, I still get to cum,” you finally say. 

You yelp as his hand comes down hard on your ass. Once, twice, three times in rapid succession. It stings, leaving your skin tingling. The sensation shoots right between your thighs, reinvigorating the swelling need inside you. 

“You really wanna cum that bad you’d let strangers fuck you?” He says with a condescending incredulousness. “God, you’re more pathetic than I thought.”

Another slap, this time to your other asscheek. Your fingers grip the edge of the sink as you resist the urge to rock back towards him. Your cheeks burn from the sting of his words, but he’s not finished. 

“Do you think of me when you fuck yourself?”

You didn’t think your cheeks could grow any hotter in embarrassment, but he never fails to surprise you. 

“What the fuck kind of question is that?” You squeak.

“The kind I expect answered,” he says with another slap to your ass. 

His hand smooths over the warm skin and you nearly moan when it slides inward, his thumb ghosting across your pussy. 

“Why does it matter?”

“Because I wanna know if I make you scream my name even when I’m not here to fuck you senseless.”

Your mouth opens and closes as you try to formulate a sentence, but it’s hard to focus with his thumb stroking the slickness of your core. It’s teasing, not enough for the sensations to build, just enough to keep you on edge. 

You cry out, flinching forward only to be stopped by the sink, when Dean’s hand makes contact with your exposed pussy this time. It hurts more than your ass, but the pleasure that it turns into isn’t diminished. 

“Answer me, slut.”

His hand comes down on your core again and you can’t contain the moan that comes with it. 

“Yes, I think of you,” you relent, gripping tighter to the sink. 

His thumb presses against your clit and your breath catches in your lungs. The pad rubs circles around the nub and you could cry from the direct stimulation. 

“Good.” Is all he says before you lose sight of him in the mirror when he sinks to his knees behind you. 

Your head drops forward at the first puff of his hot breath against your core. His tongue follows, licking a hot stripe up your pussy. A soft moan leaves your lips as he does it again, the tip of his tongue swirling around your clit as he uses both hands to grope your asscheeks. 

His stubble scrapes against your inner thighs, the combination of sensations making your head spin. You rock back against his face, and surprisingly he lets you. His tongue and lips lick and suck at your core, and nothing about the way he’s eating you out is quiet.

Your hips buck when his teeth close around your clit, not ready for the sudden second of pain. His tongue is right there following, licking away the immediate hurt. His thumb takes over, his tongue dipping inside you. 

“Don’t stop, please,” you moan, grinding back on his face. 

“Wasn’t planning on it,” he says, pulling away from your pussy just long enough to say as such before going right back. 

The pressure of your climax rushes up and you barely have enough strength in your legs to keep yourself upright. The orgasm roars through you in one giant wave. Your mouth falls open as his mouth works you over through it. 

In the mirror, you see him stand, and then you’re being flipped around so that you're leaning back against the sink again. 

His lips connect with yours and you can taste yourself on his mouth as he kisses you. It’s not gentle, his teeth clash with yours, your tongues dancing and somewhere in the way he licks into your mouth you feel his hand slide between your bodies to your pussy. 

You’ve barely recovered from the orgasm he just brought you to, and now his middle and ring finger are slipping inside you. 

Carding your fingers through his hair, you kiss Dean hard, letting his mouth swallow your desperate moans. Stars spark behind your eyes as he curls his fingers up towards your belly. Quickly, he finds that soft spot that makes your legs feel like jelly, threatening to send you to the floor. 

“De-Dean! Oh fuck,” you cry out. 

His mouth has migrated to your neck, sucking hard on your pulse point. You clench hard around his fingers, a different kind of pressure building low in your belly. Another orgasm builds slowly, especially as the heel of his palm presses against your clit. 

“That's right, bitch. Scream my name. Scream it loud so everybody out there knows who you belong to.” 

He shoves his fingers further into your sloppy pussy, wet and obscene sounds reaching your ears. Your head lolls to the side, allowing him better access to kiss and nibble on your neck. You’ll have to wear make up to cover up the hickies that he’s undoubtedly placing along your skin like a sign to say you’re his. He punches his digits in and out of you, petting that fucking spot. 

Your thighs are trembling so hard now— so is the entirety of your body. The pressure just keeps building and building. He’s everywhere, between your legs, other hand groping your body, his mouth on your neck. Nowhere is left unattended and it is so much.

“Feel you clenching so fucking tight on my fingers, baby. Gonna cum again for me?” Dean says against your neck, leaning up to nip at your ear. 

All you can do is nod. Words don’t feel real to you right now and no amount of anything could change that. 

Your nonverbal confirmation seems to satisfy him well enough. Then, he does something, something so good and he keeps doing it. Everything around you fades to just his ministrations and the feel of his body caging yours, and you feel the pressure snap. 

Everything goes white and your body seizes up with the intensity of which your orgasm slams into you. But Dean’s fingers don’t stop. They continue to pump into you, curling into you. You don’t even feel in control of your body as you feel yourself gush all over his hand. 

Dean curses under his breath and you just barely acknowledge it as you gasp for air, clinging to his shoulders with all your might. 

Dean draws his fingers from you and a perverted sense of deja vu hits you as he licks you from his fingers. He keeps you upright with his other arm snaked around your waist, and for that you are grateful. 

“Did— did I just…?” You pant, slowly realizing what’d happened. 

“You just squirted all over my fucking hand,” Dean affirms, wiping his hand on his jeans. “Wish I would’a just stayed down there. Drank it right from the source.”

You groan at his obscene words, unable to stand the way his verbal filth immediately makes your overstimulated body respond in kind. 

He taps your cheek none too gently. “Don’t go tapping out on me now. We’re not done yet.”

You’re putty in his hands as he spins you around, bracing your hands on the edge of the sink. He let’s go, and on shaky legs you stand there watching him shove his jeans and boxers back down his thighs. 

“You’re so wet, not gonna have any issue getting in,” Dean mutters quietly. 

You moan softly at the drag of his cock through your arousal. The spongy head of him bumps against your clit and you whimper, the overstimulation becoming borderline painful. 

“What’s a’matter?” Dean asks. “Too much?”

“Uh huh,” you nod. 

“Too fucking bad.”

You moan weakly as Dean presses forward, shoving the blunt tip of his cock inside you. Involuntarily, your hips sway forward, away from the stretch. With how wet you are, there’s not much pain, but his fingers can only prepare you for the girth of his cock so far. 

Dean’s hands grab fast to your hips, pulling you back to him, the motion sinking you down onto him almost to the hilt. You gasp a moan, feeling unbelievably full to the point it knocks the air from your lungs. 

“Where you goin’?” he grunts, working his hips forward and back. “I know you’re not running from my cock after crying for it.”

“So big,” you gasp, inner walls clenching around him as you try to adjust to the sudden stretch. 

Dean leans forward, rutting his cock into you. “Stop your fucking whining and take it, pathetic slut. I can feel you dripping down my balls.”

Tears prick at the corners of your eyes as his words hit their mark. It’s all so much; you can practically feel every vein and contour of him inside you. As he drags himself out, the bulge of his head catches on that sensitive spot, immediately making your legs shake. 

“Oh, baby, cry all you fucking want,” Dean lays a sloppy kiss to your bare shoulder. “All it’s gonna do is make me harder.”

As if in emphasis, he snaps his hips into yours. You are thrust forward, the unforgiving edge of the sink digging into your lower stomach. Blinking, the tears leak down your cheeks, rewetting the paths from the ones that had fallen earlier. 

His arm snakes around to your front, pulling you back against his chest. A big hand pulls your shirt and bra to the side, enveloping a breast. He rolls the hardened nipple between his fingers, every movement made with expert precision. 

You swear you can feel his cock in your stomach with every grinding thrust into you. His hips barely break contact with your ass like he can’t be bothered to pull out for even a second. The outcome is his cock stimulating that sensitive spot; the pressure is helped by the way the sink edge ensures he slides along it with each and every movement. 

“So fucking tight, baby,” Dean moans in your ear, still fondling your breast. “Always a perfect fuckin’ cumslut for me.”

Your hand reaches behind you both, sinking your fingers into the hair at the nape of his neck. His balls slap against your skin as his thrusts grow longer, his hand sliding up from your tit to your neck. He doesn’t squeeze this time, but just the feel of his calloused palm and fingers circling your throat makes you clench around his cock. 

“Fucking me…so good,” you moan out, holding a hand to his wrist. 

“Say my name, bitch. Who’s fucking you so good?” He growls, nipping at your shoulder. 

“You are, Dean,” you babble. 

The hand not on your throat dips between your legs, finding your thoroughly abused clit. A whine crawls its way up your throat and you feel his hand tighten almost imperceptibly around your neck.

“Shut up. I don’t wanna hear it,” he snaps. “Just take it. Fucking take it.”

“But—”

“I don’t care. Not my fucking problem.”

And he doesn’t, his fingers speeding up their motions on your clit. Sharp pangs stab at you with each brush of his callouses over your swollen nub. It all melts into pleasure and all you can do is push your ass back against him, meeting his thrusts. 

Dean moans his approval. “See, that’s a good whore. Feels fucking good, don’t it.”

“Yes,” you keen, slamming yourself back on his cock.

His thrusts don’t let up. Instead, they become more forceful, sending you into the sink hard enough you’re sure you are gonna have bruises on your hips tomorrow morning. His cock throbbing against your inner walls, and his panting moans in your ear have become ragged. His fingers on your clit are unrelenting, pushing you towards the brink of yet another orgasm. 

He’s all but draped over your back at this point, snapping his hips into yours erratically. Just when you think you can’t take any more, Dean groans into your ear. 

“Gonna fucking paint this pussy white, and you’re gonna take it all. Y’hear me?”

Your pussy pulses in response. “Yes, please cum in me.”

Dean moans and it’s one of the sexiest things you’ve ever heard. “That’s fucking right. Beg for my cum, bitch.”

His hand slides from your neck to your shoulder, bracing you and himself as he thrusts harder, balls slapping harshly against you. The grip is bruising, but you’re too far gone to care. 

“Please, cum in me, Dean. Need’a feel you fill me,” you whimper.

“Oh fuck, baby.”

You feel hips stutter then, his cock throbs as his orgasm hits him. He’s not quiet, moaning your name loudly.  

You can feel his cum filling you, thick ropes spurting into your pussy, and that alone sends you over the edge, yet another orgasm crashing into you. This time, your violently shaking legs give out. 

Instantly, Dean's arm wraps around your waist, holding you there as he gives a few more rutting thrusts into your pussy, milking his cock. You both stay there for a second, heavy breathing filling the room as you gasp for air. 

He breaks the silence first. “Can you stand?”

You take a second, assessing your still trembling body. Finally, you nod. 

Taking you at your word, Dean relinquishes his hold on you, leaving you to brace yourself on the sink as he walks over to the paper towel dispenser. He snags a few, using them to clean his cock off before tucking himself away. 

He doesn’t offer you any, instead he turns and unlocks the door. 

Sparing a glance over his shoulder, he gives you that sharp grin. “So, same time next month?”

You tug your clothes back into place. “Fuck you.”

“Darlin’, you just did,” is all he says before he disappears out the door. 

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

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Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

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@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

Dean glances down at each packet. He snorts and tosses the first one into the metal garbage bin beside his desk. Sam frowns.

“What was wrong with that one?”

“He’s a dude. Don’t you think we’ve got enough of a sausage fest going on around here?” Dean says, gesturing wide at the multi-floor building that makes up HunterCorp. His father’s enterprise, distilled down to two sons who, on their best day, have very different opinions on what makes for a good executive assistant.

Sam utters a longsuffering sigh.

“Man or woman, you need a real assistant, Dean. Someone competent enough to deal with your demanding schedule and…personality.”

“What’s wrong with my personality?”

“And I need you to have an assistant so I can focus on my real job. You know, running the entire Legal department.”

Dean rolls his eyes. “I know how to do my job, okay? I think I’ve picked up the slack pretty damn well since Dad died.”

Sam pauses, acknowledging that with a nod, and a heavier note.

“Yeah. You have.”

“So while I’m throwing money away hiring for a wholly unnecessary assistant, who I’m gonna have to tolerate looking at every day, I might as well be looking at somebody hot,” Dean says.

Another exhale leaves Sam’s body, along with the brief buoyant feeling of admiration for his brother.

And now we’re back where the neanderthals live. 

Sam gets a text from Reception that has his pocket buzzing. After he checks the message, he nods to himself. Here we go.

“All right. The first one is on her way up now, so do me a favor and get yourself together,” he says. “For example, it’s a little early for the booze, don’t you think? It’s 10:00 a.m.”

Dean pauses. The crystal decanter in his hand is halfway to pouring his first fifth of whiskey.

Second breakfast, if you will.

He gives his brother a flat look, one that’s accusing him of being an eternal wet blanket. But he begrudgingly concedes the point and puts both the decanter and the tumbler in a cabinet under his desk.

Classy. Sam rolls his eyes.

A knock at the door stops him from commenting out loud.

Clearing his throat, he walks over to let you in.

“Hi, Sam…and Mr. Winchester,” you say, shaking hands with the slightly taller brother. Then you turn to Dean Winchester, CEO of HunterCorp. He stands and leaves his desk to greet you.

In the time it takes him to cross the room, he takes you in within the breadth of a few seconds. More than the professional pantsuit and your pretty face, he notices your bright smile, the slight bout of nerves in the way you shake his hand. He finds himself smiling back.

“Uh, hi,” he says eloquently. “Call me Dean. Can we get ya some water, coffee, iced tea…”

He doesn’t even think they have iced tea, but he’s willing to make Sam go and find some.

“No, thank you. I’m fine,” you reply.

“Okay, then. Just, uh, take a seat.” He gestures to the open seat in front of his desk before he returns to his own plush leather chair. It squeaks as he swivels back in place. He shares a nod with Sam, who heads out of the office. The door closes behind him.

Dean glances down at the list of questions Sam prepared for him to ask each candidate, a sheet of paper that lies over your resume. He brushes the questions aside and focuses on the information printed under your name.

His brows raise in interest. “You graduated from Stanford University like my brainiac brother?”

The sound of your light laugh draws his gaze from the page, up to your face.

“Yeah, we were actually friends. It’s just been…a while,” you say, clearing your throat a little.

Dean inclines his head. His understanding grows along with his suspicion as he reads.

“Look at that, a Marketing major. Looks like you had a couple of promising internships too.”

“In college, yes.”

“And you were a Communications Specialist at Ashland for…eight months in 2021?”

“Yes, that’s right.” Again, you nod, smoothing a non-existent wrinkle in your pants. Your gaze falls away from his.

This time, Dean thinks you know full well what he’s getting at when he sets down your resume.

“That was five years ago,” he says. “You haven’t worked in five years since getting out of college?”

“It’s a bit complicated,” you admit, though you sit a little straighter. “I gave birth to my daughter, Emma, in November of 2021. My ex…was not supportive. My mother was also having some heath issues, so I moved back home to help my father take care of her. They took care of me too.”

Your fingers flex and interlace together in your lap. Dean notices the subtle fidget, but otherwise you’re calm and professional as you admit to something so personal. He can respect that you didn’t try to bullshit him.

“Hmm. Complicated,” he nods, then hesitates. “How’s your mom doing now?”

Your lips tug, but not at a smile. “She passed away a few weeks ago.”

Dean dims further as he inhales deeply. “I’m sorry.”

You give a tight nod, your throat swallowing.

“Look, since you’ve been honest with me, I’m gonna be real with you,” he says. “I run a company of 300 employees, 20 departments, 10 floors. I work 60-hour weeks minimum. I meet with department heads, shareholders, business partners and prospective clients on the daily—the kind of schedule that would make your head spin. I know you’ve done what you had to do, but I’m not sure you’re ready for a job like this. And that’s besides the fact that I’m not convinced I even need an assistant who’s probably just going to slow me down by sticking her nose into my process and asking questions I don’t have the damn time to answer.”

You tighten up at that, understandably taken aback. Your lips purse, but instead of tossing him a fuck you then and walking out, like he half expects, you sit with his words. You think it through, and you give him exactly what he doesn’t expect. 

“I may not have been clocking into an office for the past few years, but I haven’t been a stranger to hard work, Mr. Winchester. I’ve done nothing but fulfill the role of an assistant,” you say, and your gaze never leaves his when you say it. “Appointments, calls, messages, emails, paperwork, finances, data reports, coffee, power lunches, drycleaning—whatever you need, however quickly you need it, I can get it and I can make it happen. If there’s someone you can rely on, it’s a single mother who knows how to get shit done.”

Dean understands now. He understands the pain hidden in your eyes, and the too-tight set of your shoulders that hold the weight of responsibility. Urgency. A hint of desperation.

You need this job, maybe a little too much.

He should let you down gently. You’re not the kind of girl he’s looking for.

But whenever his mind and his gut are in conflict, he usually heeds his gut. That’s worked out well for him so far.

So he shrugs, and he stands up, holding out his hand to you across the desk.

“Like I said, call me Dean.”

Two Weeks

He groans into the ceramic mug at the first sip. Jesus Christ, you make a good fucking cup of coffee. That’s not even in the top five of the talents you possess, as it pertains to his business and your ability to learn quickly, talk minimally, and begin to anticipate his needs.

You dress nice, you’re always on time, and hell, you smell good too. Like body lotion and just the right amount of perfume. Obviously he can’t comment on any of these things, unless he wants a visit from Meg in HR. But it doesn’t stop him from noticing you, his heart thumping whenever you come in close to show him a document or ask him a question about a report.

Instead of rolling his eyes or snapping that you should have someone who’s not running this entire company explain it to you—like he did the last assistant who didn’t even survive three days—Dean finds an ounce of patience to spare for you.

He sits there and explains the difference between an M1911 handgun and a shotgun, and why the background checks take two months for one model and a few weeks for the other one is just a difference of state law, not HunterCorp’s manufacturing techniques.

Sam is rather fucking gloaty about it too—mainly at the fact that his top candidate made it through Dean’s initial hiring plans.

“Admit it, she’s good,” Sam says later in the day, while the two of them eat lunch together in his office. You just had it delivered ten minutes ago, still piping hot.

“She’s all right, for being your little college friend.” Dean slurps his lo mien and casts his brother some side-eye. “Is that all she was, or did you two occasionally sneak off for a little rec room break on the side?”

Sam gives him a flat look. “No, I was with Jess by then.”

“Just asking.” Dean shrugs. Secretly, he’s pleased. “You know anything about the ex-boyfriend, Father of the Year?”

Sam snorts in derision. “Some asshole in Sales while she was at Ashland. From what I heard, they were dating for six months or so, and she got pregnant. He, uh, tried to get her to end it.”

Dean frowns, and actually pauses eating to raise his head.

“She told you that?” he asks.

Sam holds back on answering for a suspicious moment, his eyes shifting down at his food.

“Made a couple calls to some contacts I have over there,” he says.

Spies, in other words. Dean nods in understanding. His brother’s always been the smart one. That’s what everyone used to say, including their father.

Two Months

You’re not sure if you should do it.

You have a sensitive report in your hand, fresh off the printer. You really think Dean should see it before he gets any deeper into his negotiations with Roman Enterprises, but he’s meeting with them right now in the big conference room, with Dick Roman himself, as well as the rest of his sales and legal representatives.

This isn’t the first meeting Sam and Dean have undergone with the company; Roman Enterprises been courting HunterCorp into a partnership on a new product, but this could be the day that makes the big swinging dicks in the room shake hands (even if that little visual almost makes you snort).

Dean’s never expressly warned you about entering a meeting uninvited, but it’s still nerve wracking as you stand outside the door. You can hear familiar voices, including the nasally tone of Alastair, the one who gives you the creeps whenever he slithers through the office and gives you a “charming” once-over.

But you also hear Dean. His voice is deep and smooth and confident. It gives you the little confidence boost you need to twist the knob and push the door open.

Just as you predicted, with a sinking feeling, all eyes turn to you when you enter the conference room. Sam and Dean and their lead sales manager, Cas, look over at you in varying degrees of surprise (Cas with disapproval). Dick Roman remains impassive, if slightly amused when you squeak out an, “I’m sorry.”

It’s Alastair’s gaze you feel on your profile when you quickly make your way around the large conference room table and over to Dean. You lean over to hand him the paperwork.

His lips purse when he notices the line of Alistair’s gaze—on your ass.

Dean then frowns at you, and your express delivery.

“What’s this? You think it could’ve waited?” he asks in a low whisper.

“Look,” you whisper back, pointing to the section you starred. It’s a report that Roman Enterprises failed to disclose about their product, a double-chambered gun that can store silver rounds and witch-killing bullets as well as salt rounds: the perfect gun for a hunter.

The problem is the safety and performance report. The one Dean has up on his laptop doesn’t match the one now physically in his hands—the one that says two out of three units of this gun fail to chamber correctly on reloading, resulting in a backfire on the user.

Dean’s brows furrow. “Where did you get this?”

“Is something wrong?” Dick asks. He straightens in his seat, his demeanor a fraction sharper.

Dean glances up at him, then at Sam and Cas, who wear similar looks of confusion. Sam raises his brows expectantly.

“Sorry, one moment,” Dean says to the room, before redirecting his attention to you.

You’re all too aware of being the rabbit caught in the proverbial trap in this room of nearly all men, but you rest a hand on the table and lean in near his ear.

“Their weapons analyst sent this to me,” you explain. “He almost got his hand blown off. Said they didn’t want to go back to the drawing board and waste time when they had us as a prospective distributor.”

Dean blinks in surprise. A fucking whistleblower just outed his own company, but he supposes he can’t blame the guy. If he had half a hand, he’d sue everybody.

“Okay, thank you,” Dean tells you.

It sounds like a dismissal, and truth be told, you’re ready to get the hell of this room. You make a quick escape and shut the door carefully behind you.

Dean watches you leave, but then he collects the report you gave him and passes it along to Sam, with a pointed look that says read it now. Sam doesn’t need the prompting. He shares it with Cas, and they both eventually come to the same frowning conclusions as Dean.

“You gonna fill us in on what that little skirt just gave you that has all of you so fucking sour?” Alastair remarks.

It makes Dean bristle. “That’s my assistant. Have some fucking respect.”

Dick shoots his associate a warning look, as well as a placating hand before he folds both of his on the table.

“Apologies. I’d like to move forward here. How about we discuss oversees shipping—”

“No, I don’t think that’s necessary,” Dean says. He shares a look with Sam. He’s disappointed, but he nods in agreement all the same.

Dick’s head tilts. His fake-ass smile twitches at the corners. “Excuse me?” 

Dean closes his laptop and slides your report across the table.

“We deal with all kinds, but there’s nothing I hate more than a liar,” he says. “Cas will see you guys out to your line of Teslas out front.”

You’re sitting at your desk, stress-eating with a snack bag of popcorn while you answer emails, even though your mind is racing as you imagine what might be going on in that conference room.

You perk up in your seat when the door swings open, and the entire team of Roman Enterprises files out with steam practically coming out of Dick’s ears. You’re more than happy to see the back of Alastair. Cas follows them closely, while Sam and Dean are the last ones lingering outside the door.

They speak for a moment there in the hall, though you’re too far to hear what they’re saying. Dean eventually rubs a hand over his stubble-covered cheeks and jawline as he heads toward his office, and toward you. He gives you a wry look when he steps through the glass doors of the reception area, squeezing your shoulder as he passes by.

“Good job, sweetheart.”

That’s all he says as he disappears back into his office. You can’t help the warm blush blooming across your cheeks, but you do get up to follow him.

“Um, Dean…”

He turns to you as the door of his office closes behind you. You fold your hands in front of you, an almost contrite expression across your face.

“I’m sorry. That just cost you a lot of money, didn’t it?” you ask.

Dean shakes his head. “Don’t be sorry. What you saved me is one bitch of a headache, and probably millions in legal fees. So thank you.”

You smile, making him smile in return.

“Okay, um, would you mind if I leave just a few minutes early today?” you ask. “My father usually picks up my daughter after school, but he has a doctor’s appointment. I can come back after she’s settled.”

Dean frowns. “What time does she usually get out of school?”

“Three. She’s in kindergarten.”

He considers it for a moment. “You know, we have a daycare. Cas brings his kids here too.”

You do know that, all too well. Cas is married to Meg in HR, and they have two, very odd twin daughters. You think they’re stealing ink from the printer and using it for “ink blot tests.” You didn’t know that eight-year-olds knew what those were.

“We do. But I, uh…I can’t afford it,” you admit, with some embarrassment. You’re still helping your dad pay off your mom’s medical bills, and even her funeral. It’s not easy to afford to live and provide for a child, but it seems like it’s almost as expensive to die.

Dean taps his fingers on his desk. He shrugs and rounds his desk to sit down in his comfortable chair.

“How much does it cost?” he asks.

“$500 a month. I’m already trying to get her into a private school…”

Dean does the math in his head, easy. Then he sends a quick text to Meg in HR.

“Well, now you can afford it. I’m gonna raise your annual salary by $10K,” he says. “That should cover the tax deductions and extra gas mileage.”

Your mouth falls open in shock. It closes, then opens again before you’re able to make words pass through them.

“Um, w…what?” you ask.

Dean leans back in his chair and smiles. It isn’t often he gets you flustered.

“Consider it an early Christmas bonus,” he says.

You laugh, slightly breathless still in wonder. “It’s the middle of July.”

Again, Dean shrugs. “Just say thank you.”

You bite your lip in amusement, but you nod. Your gaze on him is sincere, and a little shiny with emotion. Your daughter’s definitely getting into private school now.

“Thank you,” you say.

Dean watches you walk out of his office, along with that brief look over your shoulder before you close the door. His smile fades.

“Fuck,” he mutters.

He sits up in his chair and goes for that stash of whiskey under his desk. If he wasn’t already an alcoholic, you sure were on your way to making him one.

Three Months

Dean blows out a sigh, then rubs his eyes at the strain of just how long he’s stared at a screen and tried to make these goddamn numbers work.

The building is probably empty by now. Even his brother left two hours ago to go home and have dinner with Jess. Dean’s reluctant to go home to his empty apartment. So here he sits, the workaholic that he is, as the sun fades behind other buildings and casts his apartment into darker shades. He switches on the desk lamp.

A knock on the door kicks his thoughts out of alignment, like an old engine sparking out, into crispy defeat.

“Yeah,” he calls out without looking up. He does though, when you come into view.

“Hey, I’m heading out,” you say.

He can see you’re ready to go, packed up and on your way downstairs to pick Emma up from daycare. He still hasn’t met the kid. He’s surprised himself with the idea that he wants to, though he’s never asked. Never wanted to intrude on your life outside of work. Never wanted to get too close to it.

You’re a single mother living with your father, and that’s complicated enough. You don’t need a man like Dean upsetting the delicate balance. And he doesn’t think he can give a woman like you what you need…besides the fact that you’re his employee.

“All right. Make sure Benny keeps an eye on you heading to your car. It’s getting late,” he says.

“Not that late,” you say with a smile. Though you’re a bit concerned when you step further into his office. “When do you typically head home?”

“Uh, around eight or nine, usually.”

“That’s pretty late. You don’t have anyone waiting on you?”

“Not unless you count the beers in the fridge,” he remarks, sending off another email to a sales rep to get his ass in gear if they’re going to make quota for Quarter 3.

By the time Dean looks up, he sees your small frown. Concern.

It rubs him the wrong way (or maybe the right one), so he clears his throat and waves you over to his computer, opening up a tab he was looking at earlier.

“Hey, do me a favor. Tell me what you think of these. I have to go to some tech expo this weekend with Sam,” he says.

You look over his shoulder at the rows of ties on the screen.

“Well, first of all, don’t get them off Amazon. Go to a men’s store,” you say with a short laugh. “Second, what color is the suit?”

“Uh, just black,” he says in amusement.

You hum in contemplation. The man does look good in his usual slacks and nice buttoned-down shirts, but picturing him in a full suit and tie is an enticing image.

“This burgundy one looks nice. Or the blue one with the pattern,” you suggest.

“You don’t think it’s too loud?”

“No, I think it would look nice with a black dress shirt. Or hey, a black vest with a white dress shirt underneath.” 

“A vest?” Dean intones.

“Yeah, with your shoulders, you’ll look really sharp when you pair it with the suit jacket,” you say.

“My shoulders, huh? What about ‘em?” he asks in amusement, verging on the edge of flirtatious, before he realizes what he’s doing.

You both pause then.

You eventually find something approaching a respectable response, if not really a professional one.

“Just…you have a strong frame for a suit. I’m sure whatever you pick will look good,” you say. Though you turn away to grab your purse from where you left it leaning against his desk on the floor. Your face is blushing hot all the while. “Um, have a good night. I’ll see you tomorrow.”

“Yeah, you too,” he nods, clearing his throat. He tries not to watch you leave, but he can’t help himself. The natural sway of your hips is too hard to ignore, as is the way you walk away from him on those heels.

Once the door is firmly shut, he tips his head back against his chair and groans. He hates himself for hoping, even fantasizing, that one day you’ll come back and straddle him on this goddamn chair and fuck him with those heels still on.

He bangs the back of his head repeatedly against the chair, as if that could rid him of his pig-like thoughts.

Fuck. Me.

Four Months

Dean steps into his office after four hours of solid back-to-back meetings. If he had to sit through even five more minutes of Crowley’s condescending ass explain 15 subsections of a contract, as if Dean didn’t know how to fucking read, then he was going to throw his laptop into the nearest window.

He expects to find the quiet refuge of his office, and very quickly his stash of Angel’s Envy. What he gets is a kid sitting in his chair, eating his Doritos. She doesn’t look older than five or six, swinging her little legs as she swivels in his nice leather chair.

The sight is so dumbfounding that Dean stops not two steps through the doorway, his hand still lingering on the doorknob. He frowns.

“Hey,” he says. Not in a nice way. In a who the hell are you way.

“Hi!” The kid smiles and waves at him with fingers coated in Cool Ranch Dorito dust.

Dean’s head tilts. “Uh, hi.”

“You said that,” she says.

His lips twitch upward. He points at her, and the chair she’s sitting in.

“That’s my seat,” he says, with some censure in his voice. “You wanna get down?”

She blinks and pauses, realizing she might be in trouble.

“Sorry.” She slides down carefully without letting go of her snack. She wears a private school uniform: a plaid skirt, navy polo, and a matching headband. Her pink Peppa Pig sneakers give away her personality though. It matches her backpack, which boasts a Minnie Mouse keychain and a princess sticker of Belle in her yellow ballgown.

“What’s your name?” he asks.

“Emma,” she replies.

Dean’s brows raise high in recognition, then they furrow.

“Interesting. Where’s your mom?”

“She had to talk to Miss Nancy, so she told me to stay here.”

Miss Nancy. Gotta be the daycare lady, Dean thinks.

“Here? As in, my office?” he asks in suspicion. “Or did your mom tell you to hang out at her desk?”

Emma guiltily glances down at her feet instead of at him, like Sammy did when he was four, and didn’t want to admit he broke their dad’s watch.

Here, it looks like Emma got bored and wanted to go into the big mysterious room. She continues eating her Doritos.

Dean can’t help but smile. “Did you find those in my desk drawer?”

She blinks up at him with the face. Like when Sam got caught looking through their dad’s old collection of baseball cards with peanut butter and jelly stains on his hands. That puppy dog look had Dean taking the fall—and the week-long grounding.

Emma tentatively offers him her snack. “Want one?”

The look on her face tells him that she’d rather not share, but it’s a clever little manipulation with those big doe eyes. Girls learn quick, don’t they?

Dean shakes his head and pulls out a nearby guest chair after setting down his laptop on the desk.

“It’s okay. You can sit here if you want,” he says.

The chair is a little high, so she reaches for the edge of his desk to help her. Dean offers her his hand instead. She’s happy to settle her little Dorito grime-covered hand in his and have him help her into the chair.

“Thank you,” she says, with that cute little voice. He almost laughs.

“You’re welcome,” he says. You’re definitely going to owe him for this one.

Dean sits at his desk and contemplates just what the hell he’s going to do with this kid for the next few minutes. At least, he hopes it’s just a few minutes. Does he need reinforcements? Should he call Sam up here? Cas?

“Are you and Mommy friends?” Emma asks.

Dean considers her question with a quirk of his head.

“Yeah, I guess you could say that. I work with your mom.”

“She said you’re her boss.”

“You know who I am?”

“Yeah. Your face is on her phone when you call,” Emma says. When she finishes the chips, he can tell she’s looking for a garbage can. He takes the empty bag from her and tosses it in the small bin under his desk. He wishes he could pour himself a much needed adult drink, but he thinks you’d have something to say about that later.

He settles on the bottles of water you keep putting in his other drawer. He grabs one for the kid, and even opens the cap for her, like he used to do for Sam when they were little.

“Uh, how was school?” Dean asks. Because what else do you ask a kindergartner?

She shrugs. “Okay.”

Fair enough, he thinks. He never liked school much, but he has to keep this conversation going somehow.

“Just okay?” he asks.

“Yeah. I don’t like math, but Music was fun. We’re learning how to play the recorder. Oh! And I drew Peppa after school. Wanna see?” she says, pointing at her backpack.

Dean raises a brow, but he grabs her backpack off the floor and hands it to her. She unzips it and rifles through her notebooks and her modest collection of crayons. She then pulls out her prized drawing to show him. It looks more like a ball of pink squiggles to him. But he looks harder, and he can see the eyes and the mouth and the nose are close enough to the character on her sneakers.

“Hey, that’s pretty good,” he indulges her, earning her shy smile.

“Thank you,” she says. But her face soon falls. “I wanted to draw her yellow crown, but a boy took my crayon and broke it.”

“Aw, that sucks,” Dean says. Though a smile threatens his lips at the little angry pout on her face. “What did you do when he wouldn’t give it back?”

“I just pushed his arm and he fell and cried,” she says.

Dean blinks in surprise. “Oh.”

Yikes. No wonder you had to go back and talk to Miss Nancy.

“But I didn’t mean to! He was mean to me first,” Emma argues.

Dean shakes his head in amusement, once again tempted to laugh.

“Well, you know, you should never put your hands on somebody. You wouldn’t want him to hit you, right?” he reasons.

The girl considers it, still with that little pout, but she nods begrudgingly.

“See? But if that kid messes with you again, you come tell me, okay? I’ll set him straight, man to man,” Dean says.

She starts to smile again. “Promise?”

“I promise. Let’s shake on it,” he says, giving her his hand. She puts her much smaller one in his, and they shake on it like adults.

“Emma?” your voice calls from outside the office in worry. The door is still open, so you catch sight of your daughter just as Dean tells you to come over. Your eyes grow wide with embarrassment as you realize where Emma ended up. You hasten inside his office.

“What are you doing in here?” you ask her sternly, taking her hand and leading her off the chair. “You were supposed to be doing your homework at my desk. Dean, I’m so sorry. I didn’t think it would take so long.”

“It’s all right,” he says.

You still look a bit mortified and apologetic.

“Seriously, it’s okay. She’s a good kid,” Dean says. You smile, if a bit wryly as you caress her head.

“Well, she wasn’t on her best behavior today, so we’re going to sort that out tonight. But thank you for watching her.”

Dean sends you off with a raised hand, though it turns into a small wave when Emma looks back at him with a sneaking smile.

He chuckles and shakes his head. Kids. Jesus.

She looks just like you.

Five Months

The insistent ring and vibration of your cell phone disturbs your deeply rooted slumber. You slap at the device charging on your nightstand and nearly yank out the cord in attempt to bring the screen to your eyeballs.

Once your bleary vision adjusts to the brightness, you growl in annoyance.

Still, you answer the call.

“Dean. Jesus Christ, it’s three in the morning.”

“I just need your opinion on the new crossbow flame throwers.”

Your sigh can probably be heard across the Atlantic Ocean.

“It’s fine, but it would make more sense on a gun, right? Half gun, half flame thrower.”

“That’s what I said! But Cas says we need to diversify—”

“Dean. Three. In the morning. Go to sleep and let me get back to dreaming about Pedro Pascal as a gladiator, feeding me grapes as his queen.”

“…You like Latin guys, huh?”

You groan and turn your face fully into your pillow.

“Sleeping now. I’ll see you in five hours.”

Six Months

“Look! Emma got first place in the Spelling Bee.”

You pass Dean your phone while he scrapes the pickled onions off his burger and onto your plate. In turn, you give him the pickle wedge off your plate. By now you know that he’s a veritable bottomless pit when it comes to food in general, except for the fact that he doesn’t like pickled onions, and doesn’t trust sushi.

He smiles as he scrolls through the pictures of your daughter’s kindergarten class.

“Clearly taking after her mom in the smarts department. Though you didn’t have to do her like that with those Pippi Longstocking braids,” he remarks.

You scoff in amusement. “Oh, come on, they’re not that bad. It’s not like she’s got a wire hanger in there. She’s just going through a frizzy phase. No matter what products I use, I can’t seem to tame that hair.”

Dean chomps his burger. You’ve reminded him at least 30 times, but he still talks with his mouth full.

“Looks like she’s trying to land a plane,” he says.

You snort, shaking your head. You shove his arm lightly and go back to eating, while Dean takes another look at the pictures.

He sees a lot of you in that little girl. She’s got your eyes, your smile, but she probably has her dad’s hair, his chin. Dean hopes that’s all the girl’s going to get from that fucking deadbeat, biologically speaking. From what you’ve told Dean, all that guy is good for is sending monthly wire payments. After you got your raise, he even tried taking you to court to get his child support reduced.

“Did you want kids—you know, before? Was that even on your radar?” Dean asks.

He doesn’t know what possesses him, but he asks.

You hum in contemplation. “Honestly, it wasn’t. I was focused on my career.”

You wipe your mouth as the thought settles in.

“I thought I’d do it right, you know? Work hard, achieve my goals, find a husband who wanted the same things I did, then build a life, and a family. I always thought I was smarter than a broken condom in the back of his goddamn Lexus,” you say, your tone bordering on disgust at the end. You shake your head and sip your iced tea.

Dean quirks his head. “Well, we’ve all been thrown a few curveballs in life. What matters is how you take it. And I’d say you’ve got the better end of the deal. You get Emma, a good job, the best boss in the world…”

You shoot him a knowing smile.

Dean smirks, but he’s still serious.

“And that guy, all he gets is a life without his kid, and without the woman who could’ve given him a family,” he says. “Sounds like a fucking chump to me.”

He continues eating, but you’re not sure if he realizes how that just tilted your entire axis. It makes you look at him differently, the warmth of admiration in your chest, and something deeper coiling in your belly, stirring up something unexpected.

You stare at him long enough that his brows furrow.

“What? Got something in my teeth?” he asks. 

Your face relaxes, your lips tugging at a smile.

“Yeah, ground beef. Can you please swallow before you talk?”

“This is how I am, sweetheart. Don’t try to change me,” Dean says, taking another massive bite. Oily ketchup dangles from the bun and threatens to stain one of his nicer buttoned-down shirts.

You roll your eyes. “Wouldn’t dream of it.”

You stick a napkin in his collar, just in time for the ketchup drip.

Seven Months

You and Sam have lunch together every Wednesday. It started out as a way to reconnect with your old friend, but it’s often devolved into an hourly venting session about his brother’s many idiosyncrasies, how he’s driving you both fucking crazy, and how to best manage the man’s schedule, as well as steer him away from any half-cocked decisions that could cause a PR disaster.

Like the time he accidentally asked a reporter at a charity benefit why albacore tuna was becoming an endangered species.

“I mean, come on. They’ve literally got fish on the menu tonight. Maybe if you people stopped eating so much damn sushi with your avocado toast, we wouldn’t need this bougie dinner party. $5,000 a plate? Give me a fucking break.”

The fact that he slept with her that night still didn’t save him from the article she published later that week, complete with direct quotes. She had a good goddamn memory.

Today though, your weekly lunch with Sam is less about quasi-therapy, and more about celebrating the fact that Jess is pregnant. You’re even helping her and her sister plan the baby shower.

“Any advice? Just, you know, about parenting in general,” Sam asks. For once, he seems less his normal confident self, and a little more sheepish. It’s sweet, even endearing.

You smile. “God, I don’t know. I’ve been winging it from the beginning. Just…be present, as much as you can. Jess is going to need you to show the hell up, without being asked, without being nagged. You’re the rock she’ll need to lean on, even when she thinks she can do it all while you’re here trying to show up for the job. Especially when the baby’s born. If you’re not covered in three layers of bodily fluids, then you’re not doing it right.”

He laughs a little. “Noted.”

Your mind veers into other directions as you finish up your sandwich and crumple up the foil wrapper. Most predictably, along the road that leads back to Dean.

“Dean doesn’t seem to be the family man type,” you remark. “More married to his work, but…he’s been really good with Emma every time I’ve brought her up to visit the office.”

“Doesn’t surprise me. He basically half raised me after Mom died. More than half, actually. Dad was always working,” Sam says.

“What about relationships?” you ask.

It earns you a certain look from Sam. You’ve come to learn that both Winchester brothers are incredibly sharp, just in different ways. Dean knows how to read people. He’s a good judge of character, and it makes him a shark in the board room, the kind of man that can take in the information his department heads serve him and make swift decisions that often pan out well for HunterCorp.

Sam is perceptive in an almost clinical way, analytical and methodical. He’s the one who can read the data and find the one thing that’s missing. He can anticipate problems before they start, and when it comes to people, Sam often catches the little things, tells and underlying motivations. It gives you away before you’ve even realized it.

“Well, Dean’s been pretty predictable when it comes to women, even before Dad passed,” Sam says.

And it’s true. Dean’s never seen the same woman more than a week at a time. You know this, because you’ve seen the “consolation gifts” he sends them. A Tiffany bracelet. An Apple Watch. Gucci sunglasses. The perfect gift that tells a girl she won’t need to stick around for breakfast.

“But to his credit, he’s up front with them,” Sam says, drawing your gaze. “They know what not to expect.”

Your lips quirk. “Sounds so transactional…and lonely.”

“Yeah,” Sam nods, “but I get it. He took a lot onto his shoulders when Dad died. Right now, Dean’s more focused on making sure we survive than on what he might want. To be honest, I doubt he’s even thought about what that is.”

For some reason, that hits you behind the ribs in a quiet, sharp strike. In your mind, you can’t help but see the familiar tense set of Dean’s shoulders hunched at his desk, eyes glued to his computer while an evening sun sets behind his head.

Even in that big office overlooking the entire city scape, he never has time to admire the view.

Eight Months

It’s your mistake.

Your fingers brush Dean’s for half a second too long when you give him a stack of purchase orders to sign. His eyes meet yours. You point out the new way you’ve color-coded the departments for each PO.

Your heel wobbles on your pivot, an uneven floorboard. Suddenly it’s his hand closing around your wrist and the other wrapping around your waist, giving you stability. Your eyes meet his, heated breaths in between.

A thank you falls from your lips, drawing Dean’s attention there.

But he lets you go.

You walk away, pretending you don’t know his eyes are following you.

You bite your lip against a smile.

One Year

“Seriously, which one?”

“Jesus, Dean. Green! I already told you.”

“No need to get snippy. I just want your opinion.”

“You always want my opinion. That’s why I already laid out the green one for you.”

“But I like the black one.”

“You always wear the black one. The black one says politician. The green one says you’re the boss, but you’re approachable.”

“I don’t want to be approachable. That’s how I get stuck in a 45-minute fucking conversation in the break room with Garth about his side hustle YouTube sock puppet show. That shit was deeply uncomfortable. I just wanted my damn coffee.”

“You know, you could also cut back on the caffeine and the booze while we’re on the subject.”

“Oh, what are you, my mother?”

“You tell me. I’m the one dressing you right now.”

You work the collar dark green suit jacket over his shoulder and smooth down the wrinkles. You firmly ignore how his gaze roams your face, and lower still. You want to pretend you haven’t noticed these signs, all while you try to stop yourself from giving any yourself.

“There, looks good,” you say. Though you make the mistake of meeting his eyes.

He grins. One of those grins that makes you want to grab his face, either mushing it into his seventeen mugs of coffee, or kissing him fucking stupid. You’ve been restraining the latter urge by a tenuous thread for several months now, mostly because you sicken yourself.

He’s your fucking boss. It’s unprofessional. You’ve already been down this road once in your life, and—

“You okay?” he asks.

Suddenly you realize how close he is. You can feel the warmth of his body, you can smell his cologne, and he sounds so sincere in his concern, briefly touching your arm.

You nod, knowing you should create some distance between you and him. Somehow you can’t force yourself to take that one small step back.

Instead, you reach for his tie. “Remember, you’re meeting Frank Devereau and his wife tonight, and Charlie Bradbury. She’s the brains behind the project, so you’ll want to talk to her about the details, how the program works, and how we can incorporate it into our existing tech.”

Dean hums in agreement, but in truth, his attention is on your nimble hands as you work on his tie. You slide the knot up to settle snugly, but not too tight against his throat. You allow your hands to slide down his chest while you admire your handiwork with satisfaction, but your small smile fades. Your mouth goes dry as your gaze travels back up to his, lingering on his parted mouth.

His hands slowly come to hold you by your arms, making your heart tap a syncopated beat.

“Does that look mean you want me to kiss you, or am I just seeing things?” he says at last.

Your eyes widen. You bite the inside of your lip, nervous energy fluttering through you, even as everything within you would like to scream a resounding yes.

“We can’t…shouldn’t,” you say, in a quieter voice. His office door is closed, but it’s not locked. There are far better reasons than that though, and you struggle to remind yourself of each and every one of them.

Dean steals your focus, however. His eyes seem greener than usual, probably because of the jacket. You picked it with that in mind.

“In this case, shouldn’t isn’t a moral argument,” he says. “It’s society’s rules. I don’t know about you, sweetheart, but I’ve never much cared about what people who don’t matter think about me.”

Your brows begin to knit together. “Who matters to you? Because my daughter and my father. They matter to me.”

“Being with me doesn’t hurt them,” he argues, a little peeved at the implication that it would; that he would hurt them, or you.

“Being with you?” you ask in shock.

Dean’s mouth opens, but he hesitates, like what he just said surprises even himself. His lips quirk at a smile.

“I know you, uh, probably think I’m not capable of something like that,” he asks.

“I mean, it is surprising,” you admit airily. Your cheeks warm in a blush. “You could have anyone, Dean…and you have.”

He chuckles dryly. “All right, fair enough. But other than Sam, who gets me better than you? Who else is gonna handle this, the pressure of my life and everything that goes with it…better than you?”

Your eyes widen. A softer smile threatens your lips, because you realize then that he’s actually serious.

About you?

Of course, that’s when your very real, rational doubt creeps in.

“People are going to talk,” you point out. “That’s why shouldn’t always matters. And you and me? Jesus, Dean, this is the oldest cliché in the fucking book.”

His hands move down to your waist, squeezing gently. Enticingly.

“Then we’ll be discreet,” he says, with one of his crooked grins. You shake your head, but you start to smile too. You allow him to pull you back in, figuratively and literally as he bows his head closer to yours.

“You really think you can pull that off?” you ask.

“Sweetheart, with the right motivation, we can pull off anything,” he says, half whispering them on your lips as he captures them with his own.

It’s slow and laced with a curling heat that licks tingles down your spine, just like his hand moving to the small of your back, pressing you into him. Your body betrays you then, with a moan in your throat and your own hands traveling up his arms, over his shoulders, cupping the back of his neck.

The graze of your nails at his nape makes him shiver and groan as he licks into your mouth, holds you tighter. You feel the press of his growing arousal against your belly.

Your good sense knocks at the door of lust and yearning, reminding you that you’re making all the same mistakes again. This isn’t a man you can trust—not with this. But Dean’s lips are hard to ignore, covered in the remnants of your lipstick as he kisses his way along your jaw and down your neck, where he sucks and nips just hard enough to make you gasp his name and writhe against him. He squeezes your ass and smiles against your skin.

“So fucking beautiful, you know that? Even the little sounds you make when I touch you. I wanna find out what that pretty voice sounds like when you come,” he says, in a voice dripped in whiskey and wicked promises.

Jesus. Your heart flutters. You haven’t been touched like this in so very long. You haven’t felt desired like this in…

“How long have you been thinking about that?” you ask, a little breathlessly. He continues his exploration, his lips blazing a sensuous trail down the column of your throat, along the line of your collar bone, and between the rise and fall your breasts. He slides open the buttons of your blouse with a practiced hand, his eyes drinking in the sight of your lace bra.

“Since the day you started wearing these sexy fucking heels,” he says, dragging his hand up your thigh, over your skirt, in a way that raises goosebumps on your arms. But he hesitates. His eyes ask a question as they meet yours.

“You need to tell me what you want though,” Dean says, more seriously than you expected. “You want me to touch you?”

Your heart feels like it’s beating in your throat, but you nod, biting your lip.

“Kiss me, touch me, make me fucking come,” you say. “But first, you need to lock that door.”

A crooked grin spreads across Dean’s face. He steals another kiss before he does exactly that—he crosses the room and locks that fucking door. You lean against his desk for a breather, but you realize that half this shit needs to go. You move stacks of files to the side, the coasters you put for his mugs of coffee along with the empty cups themselves. You push his double-screen monitors forward, giving Dean just the angle he needs to hold you from behind and start laying more tantalizing kisses along your neck.

You sigh and help him with the zipper of your skirt while he works on the bra clasp. The straps loosen down your arms, and he flings the bra away so he can get a handful each of your breasts. You moan and rest your head against his as he begins to squeeze and tease, gently twisting your nipples between his fingers. He leaves open-mouthed kisses against your jaw, sucking at your pulse point.

When his hand moves further down and slips behind the waistband of your skirt and panties, he feels your pulse flutter and trip along with your gasp. His fingers dip between your folds and find the slick mess of your arousal.

“Goddamn, baby. Soaked for me already,” he teases.

You don’t need to see his face to know that smug smirk is plastered across it. You reach back and tug sharply on his hair.

“You can gloat, or you can fuck me,” you retort.

He chuckles and kisses your temple. “Don’t you worry. You’re gonna have to bite down on my belt to keep from screaming in a minute.”

His hand that never left your breast begins to strum the hardened, sensitive nub, at the same time his other hand finds your clit. You shudder against him at that first touch, that perfect moment when you realize he knows exactly what he’s doing as he learns your body. He circles your clit slowly, but with a delicious pressure until it swells under his fingertips.

Then his long fingers dip down into your needy channel, making you whimper as you hold onto him and the desk for stability. His fingers pump smooth strokes inside you, almost as deep as he plans to fuck you with his cock.

He knows he has you when his fingers curl and brush deliberately against that perfect spot inside your inner walls. Your thighs begin to shake, your breaths labored, your hips bucking against his hand in a quiet plea.

Your orgasm rolls swift and steady against his fingers. Your pussy flutters around his hand, and he groans along with you.

“Good girl. Can’t wait to feel that squeeze around my cock,” he says, a filthy whisper in your ear.

You laugh a little, nodding in agreement. You turn around to help him with his belt.

“Yeah, right now. Want you inside me before we run out of time. You have to meet Sam downstairs soon.”

It’s another work event Dean can’t get himself out of, even if the networking opportunities are good for the company.

“You should come with me,” he says, grinning at the way you slide his jacket off his shoulders, but you toss it as carefully as you can across the nearest chair. You just had it drycleaned this morning.

“What?” you laugh. “Dean, you don’t need me there. I’m just an assistant—”

“No,” Dean says, stilling your movements when his hand cups your cheek. Your lashes raise as you look up at him, finding him serious again. His gaze roams your face, his thumb brushing your lower lip. “If it ain’t fucking obvious, you’re more.”

Your mouth falls open, but you’re not sure what’s going to spill out. Dean doesn’t give you time to figure it out, or even let himself settle into his own admission.

He just kisses you, hard and thorough, knocking any more doubts out of your mind, and any deeper thoughts out of his.

He grabs you up by your hips and seats you on his desk, rattling the surface. Your arms wrap around his shoulders on reflex. You feel the muscles flexing under his dress shirt—a crisp black. You help him yank up your skirt and kick off your panties, though they get tangled around your ankle. His slacks and boxer briefs end up coiled around his knees, just far enough to give him room and leverage to slide into your heat.

You both moan at the feeling of him settling snug inside, bottoming out, his almost bruising grip on your ass. Your thighs are wrapped almost as tightly around his waist as he lays you out more fully on the desk. It’s probably harder to do it this way, instead of him just bending you over the hard mahogany. But you’re glad you get to see his face, get to run your fingers through his hair and share his breaths while he fucks you in a slow-rolling rhythm.

It’s more intimate. It feels like it means something, especially when he once again cradles your cheek and brushes wild strands of hair away from your face. Especially when he kisses you deep enough to taste the Almond Joy you snacked on earlier.

You kiss him back just as fervently, as if this will be the first and the last time. You have no idea what happens after today, and you know that probably makes you a fucking idiot. It could lead to the end of your second chance at a career, but you want to trust this. You want to trust the steadiness in Dean’s hands and the look in his eyes.

So you give into what you want, sitting up to lay nipping kissing along his prickly cheek and neck, sucking your own marks against his skin. The way he groans and shudders and fucks you harder—it makes you feel powerful.

“Lean back, sweetheart,” he grits out. “Touch yourself for me.”

You manage to follow his lead, shakily laying back down and letting your hand drift back down your body, finding your clit. Dean watches you play with yourself, his fingers flexing against your hip. You feel him so deep, so good, that the coil of pleasure in your lower belly begins to tighten in earnest.

He’s only satisfied when you have to smother your own mouth against a cry, your hips snapping up to meet his as your release finally hits. Another few ragged strokes, and he spills into you as well.

“Fuck,” he groans into your neck, catching his breath. That was awesome.

But then, his eyes widen. “Christ, forgot a condom.”

“I’m on birth control.” You breathe out a laugh as you soothe him, caressing his shoulders.

He blinks, then he relaxes, chuckling faintly.

“Guess you just make me lose my head,” he says.

“It’s okay. I’ve gotten used to doing the thinking for you,” you tease, biting your lip.

Dean stares down at you, brows raised, yet amused at your cheek.

“Hmm, I’m gonna remember that one. Might have to punish you tomorrow,” he remarks.

You smirk, though a blush burns down your neck at the idea, and the depths of his voice.

He withdraws from you with a quiet moan, then helps you up with a steading grip on your arms when he feels that you’re still a bit shaky. After pulling up his pants, he finds the paper towels you keep handy in one of his desk drawers for the cleanup.

“Seriously, come with me tonight. I’m sure you’ve got a nice dress. If not, I’ll buy you one on the way,” he says, as you two start to pull your clothes back on. And in your case, find your bra.

“Dean, I need to take Emma home,” you say.

You pause with your fingers poised on his dark green jacket, ready to smooth down any wrinkles. The color matches his slacks perfectly. His hair is a bit messy, but overall, he looks edible and professional at the same time. He’s ready to shmooze with the heads of conglomerates and Silicon Valley tycoons and the politicians they own.

But you know you’re not a part of that world.

“Maybe next time,” you say, though you don’t really mean it. Your hand falls.

Dean nods, but he catches your hand before you walk away from him. He slowly winds you back in and kisses you thoroughly enough to make your knees buckle, just a little.

You’re still not sure if he meant what he said about wanting to be with you, or if this is just something he’ll change his mind about in the morning after a few glasses of whiskey.

You definitely think about more than just the road ahead while on your way home, Emma’s chatter filling the car. For once, you can’t say you’re fully paying attention.

Your fingers keep touching the memory lingering on your lips.

AN: 😘❤️‍🔥 How'd you like the slow build? lol Did Dean's earnest appeal surprise you there at the end? He's been a pretty successful play boy up until now, but he's really going to prove himself in Part 3 of our adventure, set shortly after Pratt Fall.

Next Time in Nothing by Halves:

Dean finds a guest spot in front of the school. The old Impala rumbles to a stop there, and he climbs out, grabbing the bouquet resting in his passenger seat.

His keys jangle in his other hand as he makes his way to the front office to check in, just like you told him to in your texted instructions. The nice ladies there give him a guest badge that he slaps on his chest, over his dress shirt, and they tell him how to get to the theater. He feels awkward and out of place walking down the halls of this school alone, but you had to take Emma over there early before the show. 

The hell am I doing here?

He has to fucking wonder.

But he promised you. He promised the kid. So he’s here.

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He has the notecards Sam gave him in one hand, a glass tumbler with a generous pour of whiskey in the other. He’s meant to address the entire company in twenty minutes, and he still hasn’t put on his suit jacket or picked out his tie. You laid two options over the arm of his desk chair: black and white pinstripe or burgundy with a tiny triangle pattern.

“Cohesion. Harmony. Camaraderie. All the things you want to inspire in your employees after another million-dollar deal that’s going to make their workloads triple over the next six months,” you say, heaving the binder onto Dean’s large desk. The rest, you mutter under your breath. “And something severely lacking between you and I.”

Dean looks up from the small print on the index card, aiming his furrowed brows your way.

“What’re you talking about?” he asks, drawing closer. He sets his glass with a heavy clink down on polished wood. He glances down at his still unbuttoned collar and starts closing buttons. “You and I are one of the most well-oiled machines in this place. By the way, which—”

You hold up the burgundy tie for his inspection. Dean’s lips twitch at a grin. It’s like you’re in his goddamn head.

“See? You already know what I want before I gotta ask,” he says. A small sigh escapes you, but you still start sliding the tie up around his neck and under his collar.

“That’s because I’ve apparently made a career out of babysitting a grown man. Move your hand,” you say, batting his digits away from doing the tie himself. You know how he likes it, done in a Pratt knot rather than an old-school Windsor.

He snorts. “I’ll tell you what, it’s your fault, okay? Before you waltzed your way in here—”

“Before you hired me?” you interject.

He smirks. “Fine, before I hired you, with barely a scrap of professional experience besides a little college internship and an eight-month stint in an office—at one of our competitors, I might add—”

He grunts when your hand “slips,” making the knot tight enough to choke him. Amused, but still giving you a censuring look, he slips a finger between the fabric and his neck, loosening it a little as he clears his throat.

“I was entirely capable of running my life without you. I made make-or-break decisions for this company every damn day,” he says. But slowly, his smile slips. The way the green of his eyes roam over your face, your familiar hands, your softly parted lips while you pretend to be concentrated on what you’re doing.

“Now, I don’t know,” Dean says. He swallows, his throat sticking. “I’m in a meeting, and I can’t get comfortable until I know you’re sitting right there to my left. You don’t even need to be taking notes or anything. All you need to do is sit there, and I’m good.”

You pause, finally meeting his eyes.

“I close on a deal, and I’m not satisfied,” he says. “Not ‘til I tell you about it. Because I know you’ve been busting your ass just as much to help make it happen in the first place.”

Your hands begin to release his tie, but he gently grips your arms, keeping you in place.

“Dean…”

“I would say it’s a crying shame that bastard knocked you up before you really got your shot over there at Ashland, but that would mean I wouldn’t have the benefits of your many talents,” he says.

You try to ignore the thing that’s creeping into his tone. The thing that makes your cheeks prickle, and warmth bloom between your legs. You sigh and smile up at him, half exasperated.

“That might just make you the most selfish man in the world,” you say.

He smirks, his thumbs beginning to brush back and forth against your arms. Even in this little number you got on, a plain white blouse tucked neatly in a long pencil skirt, he can’t help his imagination. He’s fantasized about helping you for a change, with that pointless collection of fabric and buttons on this very floor, and his mouth anywhere you want him.

Anywhere you let him taste you.

“Yeah, I wonder if Emma thinks so, seeing as I’m the one who got her mom a raise so she could go to that fancy private school,” he says, with an arch of his brow. “Looking forward to that little play they’re putting on. What was it again?”

“Matilda,” you supply.

Dean frowns. “What? Isn’t that the one where the asshole principal locks little kids in a closet and stuffs ‘em full of cake like she’s making pâté? Little heavy for Kindergarteners, huh?”

You laugh, showing off that smile he gets out of you more often than not.

“She’s kind of nervous about that, actually. But she did ask if you were coming,” you say. Your eyes lower, just like your hands smoothing down his collar, then lying flat against his chest. “God knows if her father’s going to show up.”

Dean releases his hold on you, just so he can take your chin between his fingers and raise your eyes to meet his.

“I’ll be there,” he says. Finality and promise—something a man’s never given you.

Dean knows enough to know what he’s doing, what he’s saying. His free hand molds to the curve of your waist, tightening with the edge of possessiveness.

“Dean,” you breathe a warning in his name. His lips hover near yours, one decision shy of getting his way. “We…we can’t do this again.”

“See, I get that, but I’ve been having a hard time remembering why,” he says. All the while, his fingers are toying with the zipper on the side of your skirt. He guides it down, and down, and his practiced hand slips behind the waistband, behind white lace underneath, skimming bare flesh and heat against the palm of his hand, until his fingers find the wet slit of your pussy. A shaky breath falls from your lips.

“You damn well know why.”

And yet, your hand slips across his cheek, caressing there briefly as your eyes lock with his. Then your fingers sink into his hair, and you’re pulling him into you, tangling your lips and tongue with his in a way that makes you both moan.

The hand that’s not buried between your legs has a stronghold on your hip. He guides you back against his desk, but you’re the one lowering your skirt further so he has more room to torture your clit. Rough finger pads strum you mercilessly, drawing slick arousal from your entrance.

“Oh, fuck. Dean,” you gasp against his mouth. Your fingers curl tighter in his hair. Your hips buck to the rhythm of his hand, begging for more. His lips claim wherever they burn their path, from your jawline to sucking hard against your neck. You’re not even quite on the edge of his desk, half leaning, half clinging to him for survival as his fingers plunder you deeper.

Until he withdraws his hand entirely. You’re heaving for breath, uncomprehending, but you don’t even really have time to ask him just what the hell he’s doing by stopping. Because he’s already sinking to his knees.

He grabs your thighs and pulls you in, burying his face right between your glistening folds. A gasp and a whimper choke out of you at the pleasurable invasion of his tongue. Your hand flies to his hair as you try to steady yourself on the desk.

“Dean! Jesus,” you whisper-shout. Suddenly you remember, worried, that you two haven’t bothered to lock the door this time. He’s supposed to address the entire staff body in exactly ten minutes, and he’s not even fully dressed yet. Now, neither are you.

The man doesn’t seem to give a fuck about anything sensible like that, other than devouring your pussy. Your panties are a torn scrap of fabric around your ankles, along with your skirt that you spent thirty minutes ironing this morning. But you can’t bring yourself to give much of a fuck either, not when his tongue licks up to your clit, and his lips suck around the swollen bud like it’s butterscotch candy.

His fingers join in, slipping into your hot, throbbing core. By then, it doesn’t take more than a few strokes against your sensitive walls to have you coming hard around his fingers. Black and white brittle stars burst behind your eyelids, your mouth falling open in a harsh cry.

You can’t even breathe, because he’s still fucking you with his long, talented fingers. It’s too much. It’s like pushing you off the edge of the volcano while you’re still falling, still erupting. Still want his cock too.

Your fingers tighten in his hair to stop him.

“Dean, Dean, Dean, please…”

Mercifully, he stops. His fingers slip out of you, though his tongue laps at you one more time, just to feel you squirm and shudder against him. But as he pants for breath, he presses a kiss against the inside of your thigh, reverent, an unspoken declaration.

You soften as you look down on him. Your eyes show your conflict and your fondness as you cup his face with both hands, caressing his wet, stubbly cheeks with your thumbs.

“God, baby, you’re a mess,” you laugh, grabbing a tissue off his desk to wipe at his glistening mouth, nose, and chin. He smirks in satisfaction beneath your hand.

“There you go, still takin’ care of me,” he teases, rubbing your thighs.

This is a far cry from the cocky asshole you met a year ago.

Dean Winchester, CEO of HunterCorp, who hadn’t thought he needed an assistant when you came in for your interview. He hadn’t even looked at your resume beforehand and didn’t think he was going to remember your name by the end.

Now, that man is on his knees, willingly covered in your arousal. It’s obscene, but it’s also pulling at your heartstrings. 

You guide him back up to your lips, where you can stake your claim on him. You don’t know yet if it’s going to stick, but he’s finally worn you down.

You’re willing to try.

AN: Some of my Patreon members suggested I write a Part 2 to this. What did you think of “part 1”?

And are you thirsty for more CEO!Dean? 😉

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@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

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@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

Family Doesn’t End in Blood

Dean’s head shoots up at the sound of the screen door slamming shut violently. Sam’s at the library working on some history project for school, and Bobby is down in the garage tinkering with his latest project, which only leaves one person who’d come into the house guns blazing like that. 

Peering around the corner of the kitchen, he just catches a flash of your jacket before you’re gone again, feet stomping up the stairs. He can’t help but wince as your door slams just as hard as the screen door, and all he can think is that you’re lucky that Bobby’s not around. 

He can’t remember how many times the old man has raised his voice at the three of you for slamming doors, both in the house and the car. 

“Pretty soon I’mma start taking doors off’a hinges,” Bobby had threatened maybe a few months ago, after Sam shut the door to their shared room a little too hard when Dad dropped them off for what seemed like the 10th time in the last 6 months. 

Sammy still didn’t understand why Dad would leave them behind, going radio silent for weeks and then showing up to rip them away from school and the friends he’d made. 

Dean learned quickly to not get attached to the schools, the other kids. The sting and awkwardness of being the new kid had worn off a long time ago, and now that he was almost finished with high school, his peers were less interested in who was new and more interested in what colleges they were going to. 

Sam still tried, as green a freshman as they came, but as smart as a whip. Where he got that, Dean didn’t know. 

Nor did he know where the persistence for friendship came from. Dean resigned to the fact that friends didn’t exist outside the kids of other hunters– which is where you had come into their lives. 

Your dad was friends with Bobby, from what he understood, and your old man would leave you for months at a time to the point Dean had thought you were Bobby’s daughter at first.

He knew the old man and Mrs. Singer never had kids, but at the time he thought maybe it was just another lie Dad had told him for the sake of his age. 

“You’re too young for some things, Dean,” Dad would say to questions that he didn’t want to answer. Dean knew it was bullshit, but he knew better than to say anything in opposition. 

You were always there when Dad would drop him and Sam off. At first you were shy, but the more time they spent with you, Dean learned just how much of a spitfire you were, and slowly he’d let himself get used to the idea of you being a constant in his life whenever they were shacked up at Bobby’s.

Just a year younger than him, you never acted like it, and he could count on one hand how many times he’d seen you cry. Even when you’d wiped out on the bike you found lying around the junkyard when you were nine, and you knocked out your front tooth. Not a tear was shed, just the goofy, crooked smile he’d come to associate with you. 

You weren’t smiling now, though, if the heaviness of your footfalls and the force with which you closed yourself off from the rest of the house— from the rest of the world. 

You sling your backpack off your shoulder, the bag hitting the corner of your room with a loud thud. Not a thought is spared to if Bobby was home and if he’d be up here after you with the way you shut his doors.

You couldn’t be bothered to care, not as you claw at your jean jacket, chucking it in the same direction as your bag. 

The tightness that has been growing in your chest ever since you fled the meeting with your Dad is growing unbearable. There’s barely enough room for you to breathe, let alone think straight beyond the aching in your fists to put them through a wall. 

Instead, your fisted hands rub at your eyes as that dreadful pain in your throat made itself known. The sting of tears are soon to follow, you know, and the flames of rage inside of you are stoked by that thought. 

There was absolutely no reason to cry. The asshole had never been a father to you. 

He made an appearance a few times a year, just enough to ruffle your hair and pretend that he cared before he was gone again. Hunting was his life and it would always come before you. He’d made that clear for as long as you could remember. 

Your mom had been a one night stand he’d picked up in some roadhouse, and she’d only cared enough to get a bead on your Dad and drop you off with a box of diapers and a ‘good riddance’ to the both of you. 

Or so you’d been told. You didn’t really care, too old by the time he gave you most of the truth to fall for the allure of a mystery woman out there who might want you back.

There should be no tears shed for either of them, but especially not the man you had the shit luck of sharing DNA with, but they came anyway. 

Hot and tinged with ire, you wipe them away angrily. 

The ache for arms around you creeps up slowly, but when it finally hits, it comes with enough force to kick your knees out from beneath you. You sink onto the bed, burying your face in your palms while trying to breathe through the tension holding your body hostage. 

Your dad may not have been there for you, but the man who was no doubt down in the shop,  covered in grease and cursing over some hopeless engine, had never let you down. Neither had either of the boys who called this place a temporary home just as you did. 

The boy’s door was open when you came blazing past, and you hadn’t seen Sam in there. Vaguely, you remembered him blabbing on about some kind of boring project his World History teacher had assigned earlier that week—one that would require looking at some historic documents on display in the library archives. 

Dean though, you’d seen sitting at the kitchen table, spoon laden with his typical afternoon meal of cereal halfway to his mouth when you’d stormed in. 

Being only a year his junior, you’d clicked easier with the older Winchester boy. You shared a few classes, but you really didn’t rub elbows in public. Sam tried to assimilate, but Dean didn’t care to, much to the dismay of the girls you’d overhear in the bathroom.

You’d created a life, or what good of one you’d curated for yourself. There were a handful of girls you’d sit with at lunch or laugh with in the halls during passing periods on the way from one class to the next. 

As soon as classes were finished for the day, though, Dean would be at your locker and Sam not far behind. You’d walk to the parking lot, the three of you with your elbows linked. When you’d get to the car, Sam would always call shotgun, but that was a contest he never won. 

But even with your “normie” friends, as Dean called them, you felt alien.

You knew the things in the movies they’d jokingly screech at and jump into their boyfriends arms at were real, and even though your dad kept you at a mile-long arms length from the life, you were too entrenched of it to unpeek behind the curtain. 

Not to mention, you were at the mercy of the pit in your stomach that the moment you got too comfortable here, your dad would whisk you away and send the life you’d built out of blood, sweat, and tears crumbling into the Earth in a cloud of dust. 

Well, guess I don’t have to worry about that anymore, you think to yourself bitterly as another wave of angry tears crashes over you. 

“Fuck,” you whisper under your breath, suddenly too aware of the copious amount of self pity you’re wallowing in. 

There’s other stuff too. Stuff Sam, having the most emotional intelligence out of the three of you combined, would probably know the names of. 

Disappointment is there, sure, and unhoned anger. It’s the kind that is so big, so strong, that it doesn’t care who its target is: yourself or your dad. 

You hear the door quietly creak open. The hinges are never oiled, and you never cared to fix it. The knife under your pillow, Bobby down the hall, and nearly 17 years of hunting conditioning let you sleep soundly. 

The only creature that dared enter your room uninvited is Dean. 

“Go away,” you say, hating the way your words lack the conviction with which you want to say them. 

He doesn’t, of course. 

“Bobby would’a beat your ass if he saw the way you came in,” he says with the slightest hint of amusement. 

Your hands drop from your face and your head shoots up to give him an incredulous look. “If you came in here just to lecture me, you can go. I don’t need it right now, De.”

Dean raises his hands in a placating gesture from where he’s standing across from you. “Just saying.”

“Yeah, well you can just fuck off. Can’t a girl get some fucking peace around here?”

You groan, flopping onto your back on the bed. Surprisingly, it wears the edge to your massive block of emotions down just the tiniest bit. 

The yellow-orange glow of the setting sun fills your room, illuminating the sloppily painted stars and constellations smattered across your ceiling.

Bobby had helped you paint them probably around the same time he realized you were on a fast track to becoming a permanent fixture in his household—a fact you had realized while laying in bed unable to sleep one night a few years ago. A set of sheets and duvet in your favorite color with a matching throw blanket had followed, replacing the threadbare grey ones that had been on there previously. 

You’d been too proud to say it then, but it was the first time you felt as though you had a real home. Every time you’d tried to voice it since then had ended with you choking on your words and quickly changing the subject when the old man tried to call you out on your shifty or quiet behavior. 

A small scream exits you when you are nearly bounced a foot off the bed as Dean flops down beside you. The fact the mattress is a Queen size is the only thing that keeps you from tumbling off the side. 

“God, you are so annoying!” You reach over and backhand his chest, which only dissolves him into a fit of laughter. 

It’s a sound that has become as familiar to you as your own voice, and it’s contagious in its own right. You try but fail to keep a straight face, and end up breaking into a reluctant grin.

“Yeah, but you love me anyway,” Dean says once his laughter dies down. 

“Whatever helps you sleep at night, De,”

He hums a noncommittal sound that you know means he doesn’t believe you. 

Those three words haunt you in ways you’re not sure you’ll ever be able to fully process. Said in jest? Sure, many times. But they clog up your vocal cords, clinging to them and refusing to budge when the sense of fondness stifles your chest, needing to be heard. 

You see it in the way Bobby and Sam and Dean look at you, that they know you love them. None of them are particularly good at it either, but it makes you angry you can’t say it back.

A stretch of silence follows, you’re not sure how long, but the pair of you lay there staring up at the ceiling. Your eyes trace the constellations, all of them copied out of an astronomy book that is no doubt lost in the mess of the house by now. 

But, if someone asked you to pick them out in an actual night sky, the only thing you’d be able to pick out is Polaris, the North Star. 

That’s the only one that truly matters to me, anyway, you think. 

“Wanna talk about it?” Dean asks, breaking the comfortable silence. 

The tightness that had eased through easy laughter coiled back around your ribcage. Your fingers curled into the mess of your sheets, gripping them tightly. 

“I met my dad for coffee,” you started, keeping your eyes fixated on the ceiling. “And he asks me all the usual bullshit. You know how it is. ‘Bobby doing good? How’s school? Getting good grades?’ The small talk that makes him feel like he’s not a total piece of shit.”

You can feel Dean nod beside your head and you are half tempted to leave your story there. 

Dean knows the meetings with your dad never go well. More than once he’s come to pick you up when the bastard bailed on you completely or skipped out on lunch or snacks leaving you to cover the bill including the excessive amount of alcohol he likes to order no matter the time of day. 

Dean might press a bit, given your outburst, but he wouldn’t question it hard. You loved and hated that about him; most of the time it worked in your favor, but sometimes you wished he would ask deeper questions or push the issue when you knew he could tell there was more. 

Shame burns hot, and your voice shakes when you continue. “Then he asks ‘Any boyfriends yet?’”

It’s like trying to swallow concrete when you pause, and there’s nothing you can do to stop a singular tear slipping out of the corner of your eye. It slides down the side of your face to soak into the bed. 

You flinch when you feel Dean’s hand brush against yours. Wordlessly, you release your grip on the blanket and let him thread his fingers in between yours. The callouses on his palms scrape the matching ones on your own. He gives it a gentle squeeze as if saying: go on, I’m listening.

Scoffing and full of terror, you finish. “And I’m dumb enough to say ‘No, dad. I don’t like boys.’ ‘Cause he’s my dad. He shouldn’t care, right?”

The words bleed out now, and you’re horrified as you can’t stop them. 

“And right there, in the middle of the cafe, he stands and slaps me across the face. Saying that if that’s true, then I’m no daughter of his and to lose his number. And then he was gone.”

There’s a wobble to your voice as you finish, and all you can do is lay there, petrified and waiting for Dean to do or say something—anything. 

The few times John Winchester showed his face when you happened to be around was enough for you to form a solid opinion on the man and you’d be polite by saying it wasn’t a good one. 

Within that verdict, you don’t think his reaction would have been much different than your dads. You know Dean well enough to know that while he all but idolizes the man most of the time, he is his own person. 

You just don’t know how removed he was from his father on this matter, and the longer silence stretched between you, taut like a string threatening to snap under the smallest shift, you feel yourself start to shake.

Another tear slips out, then another as the stomach-dropping fear that you’d just lost another part of the family you’d made for yourself becomes more and more real. 

“Well,” Dean says finally, squeezing your hand again. “Chicks are pretty cool.”

The sense of relief that floods you is like nothing you’ve ever experienced, and considering the circumstances, you hope to never feel it again. 

You can’t help the half-sniffle laugh that comes from you. “You’re so fucking annoying.”

“You love me,” Dean replies, and you don’t need to look at him to know he’s smiling at you. You’re too fixated on the North star painted above you, knowing his smile is just as bright. 

“I do,” you say softly, and slowly your smile fades “Do you think Bobby will care?”

Finally turning your head to look at him, you find Dean already looking at you. The unconditional love you see staring back at you is enough for more tears to well at your eyes. 

“No, Sweetheart. He’s not gonna care,” he says softly. “You’re our family. Nothin’s ever gonna change that. Definitely not you liking chicks instead of dudes.”

“You think?”

“I know.”

It takes less than a second for him to pull his hand from yours, wrapping his arm around your shoulders and tugs you closer to him. You shudder a sigh, wrapping your arms around him in kind. 

“Thanks, De.” 

“Yeah, ‘course,” he says, rubbing his hand up and down your upper arm.

The familiar warmth glows in your chest, and for the first time, your brain doesn’t stop the words from coming out this time. 

“I love you, Dean.”

His hand falters for a split second, the only sign of surprise he makes before resuming. 

“I love you too, Sweetheart.”

The makers of Kinktober 2025 are back again with a brand new list! The graphics are once again created by latte-cucumber. Check out our AO3 collection, or keep reading for more information.

More information

Kinktober is a kinky October prompt challenge that’s been running in one form or another since 2016. There are three prompts for each day in October, and the challenge is to use one (or more!) of the prompts to create something for that day. If you don’t want to use any of the three daily prompts, you can swap them out for the bonus prompts at the bottom of the prompt list.

If you have any questions, check our FAQs. Unfortunately, due to personal commitments, we won't be opening our askbox for questions this year. We've made it as rules-light as possible, though, so if your question is "Can I do this?", the answer is almost certainly yes!

Prompts

Condoms – Bratting – Watersports

Orgy – Embarrassment – Bestiality

Hate Sex – Suspension Bondage – Mind Control

Body Writing – Subspace – Master/Slave

Glory Hole – Cloning/Selfcest – Body Modification

Held Down – Riding Crops – Feeding/Stuffing

Dirty Talk – Cockwarming – Aphrodisiacs

Face Sitting – Switching – Scat

Orgasm Delay/Denial – Discipline – Whips

Gentle Sex – Chains – Noncon

Age Gap – Breathplay – Religion Kink

Phone Sex – Findom – Edgeplay

Frottage – Temperature Play – Emetophilia

Strength Kink – Roleplay – Vore

Corsets – Power Imbalance – Human Furniture

Nipple Play – Conditioning – Predator/Prey

Rough Sex – Begging – Furry

Deepthroating – Rope Bondage – Transformation

Public Sex – Daddy/Mommy Kink – Cigars/Cigarettes

One Night Stand – Pain Play – Snuff

Coregasm – Overstimulation – Predicament Bondage

Sharing – Boot Worship – Lactation

Vibrators – Caught In The Act – ABDL

Leather/Lace/Latex – Spreader Bar – Drugging

First Time – Non-Sexual BDSM – Knifeplay

Swallowing – Collars – Fuck Or Die

Spanking – Feminization/Masculinization – Inflation

Strap-On – Safewords – Torture

Quickie – Pet Play – Wet And Messy

Licking – Clamps – Oviposition

Fingering – Micro/Macro – Writer’s Choice

Bonus prompts:

Kink Discovery

Stripping

Coming In Pants

Omegaverse (Non-Traditional Dynamics)

Pornography

Sub/Dom Drop

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

He climbed into the dingy motel bed, slow and groaning. You could see the exhaustion in the darkness under his eyes, and in the dull green of his irises. You saw the evidence of his lack of sleep pulling at his limbs, because he hadn’t truly rested since he got “topside.”

Since he showed up at your apartment with Bobby in tow, scaring the shit out of you with his half-cocked smile before he proved he wasn’t a shapeshifter or a demon.

The way Dean held you then had been so strong and fragile at the same time; you felt the shake in his arms, the tension embedded in his frame, even while he was burying his face in your hair. You’d blinked hot tears that clung to your lashes, cupped his face between your hands and kissed him just as hard and desperate.

He was alive, so you were alive. That was what that day felt like for you: coming back to life.

But this was a different kind of living.

When you slid into bed beside him, he didn’t reach for you. He didn’t welcome you against his side or wrap his arm around you. He didn’t even pretend to meet your eyes, let alone kiss you goodnight. He just mumbled the empty word, like he already knew it wouldn’t be one.

Sam was still out by himself. He was doing that more often lately, ducking out and taking the car or walking into town by himself. His excuses were always valid on the surface, like getting breakfast at the diner early, or doing some research at a café, or getting an early morning run in before you or Dean rolled out of bed. Still, you had half a mind to call bullshit.

Dean had stopped trying, even though he’d noticed too, sometimes with lips pursing, jaw clenching.

Tonight, he didn’t seem to care about his brother’s nighttime habits or your soft frown as he turned onto his side, away from you.

“You okay?” you asked, despite knowing what it would get you.

“‘M fine,” he said. “Just tired.”

You nodded, even though he couldn’t see it. You wished he wouldn’t bury it all so deep. You wished he would let you help him. But Dean had always carried layers behind that stupid devil-may-care attitude, behind that cocky grin on just the right side of charming, and the old leather that draped his shoulders like a second skin of bravado.

You’d noticed that his father’s jacket was still folded up somewhere in the trunk of the Impala. Dean hadn’t been wearing it since he got back.

You couldn’t help but think that mattered, even as you laid a hand on his shoulder and pressed a soft kiss near his neck.

“’Kay, goodnight,” you said.

You felt slightly raised flesh under the thin fabric of his shirt, and you realized then that you were accidentally touching the handprint burned into his skin—the mark of Castiel, the angel who rescued him.

You quickly let your hand slip away, feeling the tension in Dean’s body.

Your heart clenched, and you had to blink the sting out of your eyes when you turned onto your side and tried to get comfortable.

The first jolt stirred the mattress, then tugged at your subconscious.

The second one, and his painful groan, made your lashes flutter. Your eyes slid open as you fought through the dregs of sleep, but his fingers clawing against your arm finally yanked you out of it. 

You sucked in a confused, pained hiss, looking over at Dean. You realized that he hadn’t meant to hurt you. He had a desperate grip twisting in the sheets, his brows tightly knitted, jaw clenching so hard you could almost hear his teeth grinding. But the sounds that were escaping his barely parted lips were too heartbreaking, like a wounded animal unwilling to let their whimpers escape, afraid for something worse to follow.

“Dean,” you rasped, reaching for his shoulder cautiously. You were wary of him trying to knock your hand away, or worse, but he just flinched harder.

It did manage to wake him up though.

His eyes flew open with a sharp intake of breath, following by more labored ones as he struggled to take you in, to realize where he was.

He rolled onto his back and stared up at the ceiling. He dragged a hand over his face, rubbing his eyes.

“Dean?” you prompted gently. You were slow in the way you slid closer, smoothing a comforting hand up his arm.

He looked over at you, tired of lying, but still unwilling to answer you.

But in that moment, you knew the truth. You knew what he was hiding, deep and dark behind his eyes when they met yours.

He couldn’t hold it for long though. His own self-loathing won out. Even just having you beside him with love and concern in your eyes was too much for him to handle.

He sat up in bed and swung his legs over the edge, but that was where he hesitated. He either lacked the strength to get up and leave you, or he was just that shaken. His eyes closed and an uneasy sigh fell from his lips, making his shoulders sag.

You crawled over to his side of the bed and bent a knee underneath you as you sat just behind him, just barely keeping yourself from touching him. You didn’t want to smother him, but you wouldn’t leave him alone either.

“You do remember everything, don’t you,” you said. The heartbreak was in your throat, but you thought it might help him to say it out loud.

Dean shook his head slowly, but this time, it wasn’t a denial. His tongue was heavy in his mouth, but he still forced himself to speak, his voice thick and rasping.

“Not just…what happened to me,” he said, his voice coarse with fatigue and pain. “What I did.”

Your brows furrowed in confusion. You didn’t understand, but he couldn’t bring himself to explain it to you—why he hadn’t been able to let you in. Why he couldn’t allow himself to touch you with his hands. Every time he looked at them, they were drenched in blood.

And when he tried to look at you, the words died in his throat. It felt selfish to try.

His lips trembled. His shoulders heaved. He covered his face as his eyes burned, and the first sob shuddered through him.

You didn’t understand, but it didn’t matter. Not tonight. Once the first tear drew down your cheek, you couldn’t let yourself do anything else but hold him from behind. Your lips pressed to his shoulder, and you held onto him as tightly as you dared.

He held you back, his hand clasping over your arm to keep you there. It gave you the encouragement you needed to slide closer, your hand cupping his cheek and stroking your thumb across his chin. His glassy eyes met yours.

“I love you,” you reminded him. “That doesn’t change.”

Again, Dean shook his head. “You don’t know. You don’t know what I…”

“Right now, I don’t need to know,” you said.

Just then, he was desperate to believe you.

He bowed into your kiss, desperate for your warmth too.

One touch couldn’t make him forget. It wouldn’t heal him either.

All you could do was stay.

AN: My heart gets ripped out every time I watch that ep where he tells Sam about his experience in Hell. 🥲💔 But let me know what you thought of this hurt/comfort snack!

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Dean Winchester One-Shots 

Dean Winchester Masterlist 

Main Masterlist

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan