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supernotnatural2005 · 2 months ago

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The Arrangement - Part One

Pairing: Dean x Reader

Summary: Dean has a conflicting dream about you, his best friend, that has him questioning feelings he'd never allowed to see the light of day before. However, he might not be the only one…

Word Count: 7.7k

Warnings/Tags: Swearing, feelings, some spicy times, nothing too heavy...

AN: Happy Release day!!🎉 Honestly, i can’t thank you all enough for the excitement around this series since announcing it! I've fell in love writing this story 🥹 and I hope you all enjoy reading it as much as I have writing it ❤️

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Dean smiled lazily as he felt a warm palm slide up his chest, the body behind him pressing closer. Soft lips trailed kisses along his neck and shoulders, sending a shiver down his spine. He hummed in contentment and shifted onto his back, his tired eyes opening to the most beautiful smile he’d ever seen.

Her eyes sparkled with warmth and mischief, her lips curving into a playful smirk before she leaned down, peppering gentle kisses along his jaw. His eyes fluttered shut again as she sucked lightly at his pulse point, his breath coming quicker. A low groan rumbled from his throat as he gripped her waist, pulling her up into a heated kiss.

Her tongue caressed his, her touch sending fire through his veins. Her hand slid down his abdomen, fingertips grazing lower and lower beneath the sheets, his pulse pounding—

"WAKE UP, LOSER!"

Dean's eyes shot open, his body jolting as the blaring shriek of an airhorn filled his room. He yanked the covers tighter around himself, his heart racing from both the rude awakening and the remnants of his dream.

"What the hell, Y/N?" he growled, glaring at the culprit as he covered his ears. You grinned triumphantly and finally put the airhorn to rest.

Dean huffed, flopping back down on the bed and throwing an arm over his face, trying to will away the heat rising to his cheeks.

What the fuck? Was all he could think, his sleep-addled brain scrambling to make sense of why he’d just had a sex dream about you.

You, meanwhile, were way too chipper for his liking.

"C’mon, Dean-o, up and at ’em." You patted his leg, and he flinched like you’d just burned him. You shot him an odd look, but he ignored it, shifting slightly to make sure the blanket hid the… Predicament he was currently dealing with.

"What’s with the drill sergeant wake-up? Can a guy not sleep in on a Saturday?" He grumbled, voice still rough from sleep, and other things.

You pouted. Actually pouted. And Dean had to force himself to look away from your lips—lips that had just been doing unspeakable things to him in his dream.

"You promised you'd go Christmas shopping with me.” You reminded him, completely unfazed by his mood.

Dean frowned. "That doesn’t sound like something I’d promise."

You hit him with your classic 'don’t bullshit me' look. And, yeah, okay, he remembered now. He'd offered last week, wanting to help you survive the chaos of last-minute shoppers—and use the trip to grab gifts for his own family.

"Fine, yeah. Just give me ten minutes to wake up, alright?" He relented, desperate for you to leave so he could deal with his little… Issue.

“Thanks, Buddy." Your voice was smug, like you knew he’d never actually say no to you. Because, let’s be honest, he never did.

Dean sighed as you closed the door behind you. He let his head fall back against the pillow, running a hand down his face.

What the hell?

Why was he dreaming about you like that? You were his best friend. You’d been inseparable since fourth grade. Sure, you were beautiful, but that had never been an issue before.

…Had it?

Dean groaned, pressing the heels of his hands against his eyes. Nope. Too early for a deep dive into that mess. He rationalised it away—one, you were attractive. Two, you were close. And, statistically speaking, didn’t most guy-girl friendships eventually veer into weird territory at some point?

Yeah. Totally normal. No big deal.

Except… Two hours later, standing in the middle of a lingerie store, Dean realised he was totally screwed.

Before that, he’d spent the last two hours hauling around a bunch of your shopping bags like a damn pack mule. Only one of them happened to be his, with his completed gift purchases for everyone he needed to buy for. Though to be fair to you, your arms were just as full. He was bewildered at your ability to buy so much for so little.

Your immediate family only consisted of three people—Bobby, Ellen, and Jo—but you had argued that you had your friends, his family, and him to buy for. The latter of which, he’d told you not to do.

However, it fell on deaf ears as always. Every Christmas and birthday, it was the same. But Dean couldn’t fault you for it—you always got people gifts that were meaningful to them, and you got so much joy from giving that he could never say anything other than thank you.

What he wasn’t thankful for was your complete inability to stay focused. Every shop you entered, you’d get distracted by little knickknacks, convincing yourself someone needed them, rather than the original item you came for. It made the day so much longer, but despite the fatigue in his arms and the chaos of holiday shoppers, he was enjoying himself.

Though, that was a given with you.

You were naturally a people pleaser, but knowing how much Dean hated shopping, you’d made it your mission to keep him entertained. You’d made him laugh—laugh to the point his belly ached and tears were shed. The day had surprisingly become enjoyable. But then you'd dragged him into this store, and his brain short-circuited.

The window displays alone had him spiralling, lace and silk-covered mannequins taunting him with thoughts he really didn’t need to have. About you. And then you, completely oblivious, pulled a matching red lace bra and thong off a rack, holding them up for inspection.

Dean swallowed hard.

He’d done your laundry before. You two split chores in the apartment, and he’d handled your underwear plenty of times; never thinking twice about it. So why the hell was he suddenly imagining you in them now?

Was this really because of the dream? It had to be.

And then, like you hadn’t already sent him into cardiac arrest, you giggled, holding up another pair. "Hey, check this out—crotchless panties."

Dean barely choked back a groan as you stuck your fingers through the open section like it was the funniest thing in the world. His brain, on the other hand, provided a detailed mental slideshow of all the things he could do to you in them.

Jesus Christ.

He needed air.

"I—uh—I gotta step outside. Promised Sammy I’d call about a gift for Mom," he lied, voice tight.

You barely glanced up. "Okay."

Dean bolted like his life depended on it, shoving through the doors and inhaling the crisp winter air. "What the fuck is wrong with you, man?" He muttered under his breath, dragging a hand down his face.

A passing woman gave him a scandalised look as she walked by with her kid. He shot her an apologetic smile before leaning back against the brick wall, blowing out a heavy breath.

He tried to clear his mind, but every time he pushed the R-rated thoughts away, softer images replaced them. The way you smiled. The way you laughed, head thrown back, eyes crinkling. That stupid fluttery feeling hit his stomach again.

Dean frowned.

Was he sick? Hallucinating?

The worst part? You were always the person he talked to when he was confused about something.

But now you were the one person he couldn’t talk to about this.

Another half hour crawled by before you finally emerged from the store, a small bag swinging from your wrist. Dean’s eyes locked onto it like it held the answers to the universe, his mind immediately spiralling.

What the hell did you buy?

He told himself he didn’t care. He really didn’t. But his brain clearly had other plans because now he was picturing you in every single thing you could’ve possibly picked out.

Lingerie? Pyjama's? Something sheer, lace- nope!

He swallowed hard and forced himself to focus on literally anything else, but it was a lost cause. By the time you both made it back to the apartment, he felt like his brain had been put through a damn blender.

You, however, were completely unbothered, tossing your bags onto the floor with a content sigh before flopping onto the couch. "Pizza should be here soon. You wanna pick the movie?"

Dean blinked, barely processing the words. Right. Normal best friend things. Hanging out. Eating pizza. Watching a movie. That’s what you two did. That’s what you’d always done.

Maybe that’s all today was—a momentary lapse. A weird, fleeting thing brought on by lack of sleep, the stress of shopping, and, most probably, the objectifying dream he’d had of you. It didn’t have to mean anything more than that.

Yeah. He could shake this off. No big deal.

Letting out a slow breath, he dropped onto the couch beside you, snagging the remote. "Fine. But if I pick, you’re not allowed to bitch about it."

You hummed, already scrolling through your phone. "I make no promises."

A small smirk tugged at Dean’s lips. This was normal. Easy. Just like always.

And for the first time since this morning, he let himself believe it.

The following Friday, Dean found himself at the Roadhouse with Benny, Cas, and Gabe. It was the kind of place that felt like a second home.

The Roadhouse wasn’t fancy—hell, half the decor was older than they were—but it had its own charm. The regulars, the outdated rodeo-style décor, the worn wooden bar top that had seen more spilled whiskey and thrown punches than anyone cared to count.

The walls were lined with old beer signs, neon lights buzzing softly under the hum of conversation. The jukebox in the corner cycled through rock classics, always a little too loud, but that was part of the place’s charm.

Dean and the guys had been coming here for years—long before they were even old enough to drink. You had, too. Being Ellen’s stepdaughter meant you practically grew up in this place, and while Ellen had a strict no-bullshit policy, she wasn’t blind to the fact that teenagers would be teenagers.

As long as you and the guys stayed under her watchful eye, she let you each have a beer or two when you were younger, making damn sure no one got carried away. And if anyone so much as thought about sneaking more? Well, Ellen had a way of shutting that down real quick. She was tough, sharp as a whip, and had a stare that could make a grown man fold—but she cared, more than she’d ever admit.

Jo helped out too, working the bar some nights in between her law enforcement studies. She’d been slinging beers and rolling her eyes at the group’s antics since she was old enough to work behind the counter, always quick with a sarcastic remark when any of them got out of line.

You and Dean had spent countless nights here, watching as the Roadhouse shaped who you all became.

Benny leaned against the pool table, lining up his shot with an easy, practiced confidence. Dean had seen him do it a hundred times—his friend had a natural ease about him, a steadiness that made him damn good at their job.

They spent most of their days working maintenance for RHP Properties, fixing busted pipes and dealing with tenants who thought every flickering light meant the world was ending. Benny made the long hours bearable.

Cas sat nearby, nursing a whiskey, his sharp blue eyes scanning the table like he was analysing some historical battle strategy. He always had that serious, thoughtful air about him. It made sense—he was a history teacher, working his way toward becoming a professor. His brain just worked differently.

And then there was Gabriel, though he liked to go by Gabe, Cas’ cousin. Though you’d never guess it just by looking at them.

Where Cas was serious, methodical, and downright broody at times, Gabe was his exact opposite—carefree, unpredictable, and always ready with a joke. The contrast between them was almost comical, like night and day, order and chaos.

Currently half-draped over the bar like he owned the place, Gabe was laughing at something Rachel, the new bartender, had said. She was easy on the eyes—exactly the kind of woman Gabe set his sights on. And judging by the way she giggled and blushed under his usual blend of wit and charm, he’d hit his mark.

Gabe had always been that guy—the one who could talk his way into or out of anything, a natural-born trickster with a grin that could disarm just about anyone. No one was entirely sure what he did for a living, some mix of marketing gigs and side hustles that somehow kept him afloat. According to him, it was all about “the art of persuasion.”

Dean just called it bullshit.

The night had settled into an easy rhythm—drinks flowing, pool games stretching long enough to become more about talking shit than actual competition. Gabe, as always, had the floor, spinning some ridiculous story about a one-night stand gone wrong.

“I’m telling you; she had three snakes. Just slithering around the damn apartment like it was normal,” Gabe insisted, gesturing wildly with his beer. “One of ‘em was watching me, man. I swear it knew.”

Benny chuckled, lining up his next shot. “I think the real question is, why the hell did you stay?”

Gabe shrugged. “What can I say? I have a hard time walking away from an adventure.”

Cas, who had been nursing his whiskey with a bemused expression, finally spoke up. “It’s a wonder you haven’t been killed yet.”

“Give it time,” Benny muttered, sinking his shot.

The conversation shifted, everyone throwing in their own weird hookup stories—bad timing, embarrassing moments, things they wished they could forget. Dean had been mostly listening, chuckling at their dumb-assery, when the thought that had been nagging him for days finally slipped out.

“Is it, uh… normal to have a sex dream about a friend?”

Benny didn’t react at first, too focused on sinking his shot, but Gabe, ever the opportunist, caught onto it immediately. “If it’s about Y/N? Yeah, totally.”

Dean nearly choked on his beer. “What? No—it’s not—”

Gabe grinned, tilting his head like he was enjoying watching Dean squirm. “Not what? Not about her? Or not just a dream?”

Dean scowled, scrambling to recover. “Jesus, Gabe, I didn’t say it was about her. It was hypothetical.”

“Uh-huh.” Gabe leaned against the pool table, twirling the chalk in his fingers. “Sure, man. Hypothetical.”

Dean exhaled sharply, trying to shake off the weird, twisting feeling in his gut. “Just saying, dreams don’t mean anything, right? Just… brain static.”

Benny chuckled, finally looking up from the table. “Depends on the dream, brother.”

Dean glanced between them, suddenly feeling like he was the only one missing something. “What’s that supposed to mean?”

Gabe smirked, eyes twinkling with mischief. “It means you’ve been making googly eyes at her since we were, what—fifteen?”

Dean’s stomach dropped. “The hell I have.”

Gabe ignored him, tapping his chin. “Honestly, I’m surprised this hasn’t happened sooner.”

Benny sighed, shaking his head as he sank another shot. “Sorry, brother. Gotta agree with the gremlin on this one.”

Cas, who had been silent up until now, finally spoke, his voice calm and matter of fact. “It’s always been very obvious.”

Dean stared at them, mouth opening and closing. “You guys are insane.”

Gabe shrugged, completely unfazed. “Denial’s a hell of a drug. You’ll catch up eventually.”

Dean gripped his pool cue a little tighter, his next shot suddenly feeling a lot more difficult than it should have.

Benny, ever the voice of reason, leaned on his cue. “Ain’t anything bad, Dean. You two have known each other since you were what? Nine. Been joint at the hip since. You know all her family, she knows yours. Hell, she’s practically—”

“If that were true, something would’ve happened by now,” Dean cut in, shaking his head.

Gabe snorted, swiping Dean’s beer before he could stop him. “Not if you’re in denial, my friend.”

Dean’s jaw clenched, frustration curling in his chest. Their words were ringing too damn true, and it was freaking him out. “You’re all outta your damn minds.”

Gabe just smirked. “Keep telling yourself that, Winchester.”

The conversation haunted him. All the way back to the apartment.

He’d walked the couple of blocks from the bar to your shared place, his friends’ words swirling around his mind, needling into places he didn’t want to acknowledge.

Dean knew he cared about you—he always had. But wasn’t that normal after knowing someone for so long? You were practically family.

His thoughts drifted back to the first time he met you. Fourth grade. The old, rusted swing set at the park near his house.

He’d been shoving loose gravel around with the toe of his sneaker when he heard a loud laugh—sharp and unbothered. Looking up, he saw a girl launch herself off the swing at its peak, landing in a heap on the ground with a thud.

He winced. That had to hurt.

But instead of crying, you rolled onto your back, a grin splitting your dirt-smudged face as you stared up at the sky. "Holy crap, that was awesome."

Dean frowned, more confused than anything. "You just busted your knee."

You sat up, inspecting the scrape with a shrug. "Eh, I’ve had worse."

Then you looked at him—really looked at him—and grinned. "Think you can jump higher?"

Dean, never one to back down from a challenge, snorted. "Duh."

And that was that. A competition was born.

For the next hour, you and Dean had taken turns swinging as high as possible before flinging yourselves off, measuring who could get the most distance. By the time the sun dipped low, both of you were covered in dirt and scrapes, laughing like idiots.

When his mom finally called him home for dinner, he’d hesitated before brushing off his hands and looking at you. "Same time tomorrow?"

You grinned, teeth flashing. "You’re on, Winchester."

And just like that, Dean had found his best friend.

Now, years later, that same friend was tangled up in his head in a way he couldn’t ignore.

And it scared the hell out of him.

“Honey, I’m home!” Dean called out as soon as he stepped into the apartment. The words left him out of habit, that same old teasing lilt in his voice. It was an inside joke that had stuck over time—born the day you’d both moved in together after college, a decision fuelled by practicality more than anything else.

Splitting rent was cheaper, and as best friends, it had made perfect sense. Somehow, though, the whole thing had felt oddly domestic from the start, and Dean had cracked the joke that first night—throwing open the door with a smirk, announcing himself like some sitcom husband. You’d groaned, thrown a pillow at him, and it had just stuck. Something easy, something comfortable.

From somewhere deeper in the apartment, your voice called back, warm and casual. “Hey!” You greeted him as he shrugged off his worn leather jacket and toed off his boots with a sigh, rolling his neck to ease the tension there.

“How were the guys?” You called out again.

"Yeah, they're all good," he answered absentmindedly, trying not to think about that last conversation he’d had with them as he headed straight for the fridge, already contemplating his options.

His hand gripped the cool metal of the handle as he swung it open, his face falling at the sad excuse for groceries staring back at him—half a six-pack, expired milk, some takeout containers he didn’t even remember ordering.

Right. Grocery shopping. Definitely overdue.

"Hey, you feel like ordering in tonight?" He called out over his shoulder. "Pizza? Chinese? Maybe both, live a little?"

But before he could get an answer, movement in the corner of his eye pulled his focus, and his breath caught in his throat.

You stepped out of your room, and just like that, Dean forgot how to breathe.

His hand slipped from the fridge handle as his entire focus tunnelled in on you. You weren’t just dressed up—you were knockout gorgeous.

A sleek, black dress hugged your figure in a way that should’ve been illegal, the fabric clinging in all the right places before tapering off mid-thigh. Your legs—long, smooth, and so much more on display than he was prepared for—were accentuated by the sharp cut of your stilettos, heels so high they had no damn business being on your feet, yet somehow, you walked like you owned the world in them.

Dean swallowed hard.

His gaze flickered to the subtle details—the delicate chain resting just below the hollow of your throat, the way the dim lighting in the apartment caught the shimmer of your earrings, how your makeup was just enough to highlight what was already perfect.

You smelled different too—a new perfume perhaps? Something subtle but undeniably you.

The air in the apartment felt thick, like it was pushing down on his chest.

You didn’t even notice his staring. Instead, you were focused on the couch, leaning over slightly as you grabbed your purse, your fingers quickly checking through its contents. "I can't," you said lightly, barely looking up. "Got a hot date, remember?"

Dean blinked, your words cutting through his haze like a blade.

“Date?"

His stomach twisted.

You straightened up, finally glancing at him with a smirk. "Yeah, with Gary from marketing?" You prompted, slinging your purse over your shoulder. "He asked me out last week—I told you about it?”

Gary from marketing.

Dean’s brows furrowed as the memory came rushing back—how you’d offhandedly mentioned it while he was distracted with something else, how he’d muttered some half-assed response at the time, maybe even made a joke—

"The guy with the tragic haircut?" he muttered, the words coming out before he could stop them.

You laughed. "That’s the one."

And just like that, it hit him.

He’d been so caught up in his own damn thoughts about you lately—trying to reason with himself, trying to make sense of the way things had shifted between you lately—that he hadn’t even thought the world would still be turning for you.

He’d been sitting in the passenger seat, clueless, while you’d been steering your own damn life without him.

And now?

Now, you were standing there, looking like that, all dressed up for some other guy—some idiot named Gary, who got to pick you up and take you out, who got to be the reason you put on that dress, who got to see that smile meant for him tonight.

Dean’s chest felt tight, a slow, bitter realisation creeping in.

This wasn’t like all the other times.

You’d gone on dates before. He knew that. He’d teased you about them, had even tossed out protective big-brother-ish warnings to guys who had no clue the words felt foreign in his mouth. But he’d never felt anything about it before.

Not like this.

Not like his chest was caving in.

Not like a bitter, ugly heat was curling around his ribs, settling deep into his bones.

Not like he wanted to throw his jacket back on and hunt down ‘Gary from marketing’ and make damn sure he knew he wasn’t good enough for you.

His hands curled into fists at his sides.

"Right." His voice was quieter than he meant it to be, rough around the edges as he forced the word past the lump in his throat.

He watched as you did one last check in the mirror by the door, smoothing your hands down your dress, adjusting your lipstick in a way that made his stomach tighten even more. You looked excited.

Dean clenched his jaw.

And just like that, the jealousy settled deep in his bones, hot and unyielding.

He didn’t want to picture it—you laughing at some stupid joke Gary made over dinner, Gary sliding his hand over yours, maybe leaning in close at the end of the night, lips hovering over yours.

But the thoughts came anyway.

And it wrecked him.

You shot him one last glance, oblivious to the storm raging inside of him. "Don’t wait up, Winchester."

And with that, you were gone.

Dean stood there for a long moment, staring at the closed door.

His chest felt tight. And then the bitter realisation hit him.

His friends had been right.

Dean couldn’t sleep.

For the past two hours, he had been tossing and turning, alternating between staring at the ceiling and squeezing his eyes shut, willing sleep to come. It never did.

How the hell could he sleep when his mind was torturing him with images of you—with Gary?

His stomach churned uncomfortably at the thought of it, bile rising in his throat. His mind painted vivid, unwanted pictures: Gary’s hands on you, his lips on your skin, your soft laughter, the way you might be looking at him right now—the way you should be looking at Dean.

He clenched his jaw, shaking his head as if it would shake the thoughts loose. It didn’t.

With a frustrated exhale, Dean sat up, rubbing a hand down his face. This was pointless.

There was no way in hell he was going to get any rest like this, not with his heart pounding and his mind running laps. He swung his legs over the side of the bed and stood, stretching his sore muscles before making his way into the living room.

His feet carried him straight to the kitchen, to the cabinet under the sink where he kept a bottle of whiskey for special occasions.

This qualified.

He poured himself a shot and downed it in one go, barely wincing at the burn as it slid down his throat. The second one went down just as easily, a bitter warmth settling in his chest, but it didn’t quiet the storm in his head the way he hoped it would.

His eyes flicked toward the clock on the microwave.

1:37 AM.

You were still out.

Another shot. Another slow burn in his chest.

Dean knew he had no right to be this worked up about it. He wasn’t your boyfriend. He wasn’t anything to you except your best friend—your roommate. That was the problem.

He ran a hand through his hair, exhaling hard.

When the hell did everything get so complicated?

It wasn’t just the dream. Sure, it cracked something open in him, but if he was honest with himself, there had always been something simmering underneath. He could see it now—in the way his past relationships never worked out, how no one else ever seemed enough because in the back of his mind, he was always comparing them to you. The way he told you things he didn’t tell anyone, not even his own mother.

Seventeen years.

You had been in his life for seventeen years. That was longer than most marriages.

Damn, he really was an idiot. How could he have been so blind to it, so ignorant to what was staring him right in the face the whole time?

Then, he heard it.

The distinct jingle of keys outside the door, followed by a clumsy, muffled “shit" breaking him out of his reverie.

Dean sighed, setting his glass down before pushing off from the counter. He made his way to the door just as he heard another "fuck", then a quiet thud—like something hitting the floor.

Through the peephole, he spotted you crouched down, fumbling for your keys, struggling to fit them into the lock.

You were clearly drunk.

Dean shook his head with a smirk, unlocking the door from his side just as you managed to steady yourself, one hand braced against the door handle. The moment he pulled it open, you stumbled forward, nearly toppling over—until his arms caught you.

You crashed into his chest with a soft “Hmph.”

Dean's arms instinctively wrapped around you, holding you up as you melted against him, giggling into his shirt. The scent of alcohol clung to you, a mix of whiskey and whatever fruity drink you had been sipping on all night.

“Jesus." You huffed, pushing off him, though you wobbled as you tried to find your footing. Dean kept his hands out, ready to catch you again if needed.

"You good, sweetheart?" He asked, raising a brow as he took in your dazed smile and glassy eyes.

You grinned up at him, your expression pure blissed-out drunkenness. "I'm just perfect, Dean’o."

Dean smirked at the nickname, but before he could say anything, you reached up and grasped his jaw between your thumb and fingers, squishing his cheeks slightly.

“Okay, alright—enough of that.” He groaned, peeling your hand away. You didn’t seem to realise your own strength at the moment, and if you squeezed any harder, you were gonna leave a dent in his damn face.

You blinked up at him, wide-eyed, before your attention drifted over his shoulder. Then your expression dropped into something heartbreakingly close to a pout.

“Awww,” you whined. “You’re drinking without me?”

You sounded genuinely upset, your lower lip pushing out in an exaggerated fashion. Before Dean could respond, you made a clumsy grab for the bottle on the counter.

But Dean was quicker.

Before your fingers could wrap around the neck of the whiskey bottle, his hand closed over yours, pulling it away with ease. “Yeah, no. You’ve had enough,” he said firmly, setting the bottle behind him and out of reach.

You frowned up at him, your brows knitting together like a scolded child. “You’re no fun.”

Dean smirked, amused at how downright grumpy you looked, like a kid being denied dessert. He leaned against the counter, arms crossed. “You need some water, sweetheart. Not more booze.”

You huffed dramatically, crossing your arms over your chest. “I don’t want water, I want whiskey.”

“Tough,�� Dean said, already turning to grab a glass from the cabinet. “You’re getting water.”

Your pout deepened as he filled the glass from the tap, sliding it toward you. You eyed it like it personally offended you before reluctantly picking it up and taking a sip—your way of conceding to his demand, albeit with an exaggerated sigh.

Dean chuckled, shaking his head. You were something else.

Once you were distracted with your water, he leaned against the counter again, crossing his arms over his chest. He could still feel the tension coiling in his gut, the jealousy he’d been drowning in all night, and he couldn’t hold it back any longer.

“So,” he started, keeping his tone casual, but his fingers clenched against his biceps. “How was it?”

You blinked up at him, confused. “How was what?”

Dean gave you a look. “Your date.”

At that, you scoffed, setting your glass down with a little more force than necessary. “Oh, that.” You waved a hand dismissively. “It was awful.”

Dean raised an eyebrow, surprised by how quickly you admitted it. He’d expected you to defend the guy, maybe try to convince yourself it had been a good time. But no—just flat-out awful.

“Yeah?” He prompted, keeping his voice even, but he could already feel his chest loosening just a little.

You leaned against the counter, your drunken state making you extra expressive as you talked with your hands. “First of all, the guy is so uptight. Like, I swear, he’s never laughed in his life. I tried joking around, and he just blinked at me like I was speaking another language.”

Dean snorted, already picturing it.

“And then,” you continued, eyes wide with disbelief, “all he did was talk about himself. Nonstop. Like, dude, I asked him one question—one—about his job, and suddenly I was stuck in a TED Talk about marketing strategies. Like I don’t work for the same company.” You threw your arms out in a ‘are you kidding me’ gesture.

Dean chuckled, shaking his head. “Sounds like a real winner.”

“Oh, it gets worse,” you said, holding up a finger. “So, we order food, right? And I get a cheeseburger, because, you know, I wanted a damn cheeseburger.”

Dean nodded approvingly. “Good choice.”

“Right?” You gestured wildly, as if proving your point. “But Gary—freaking Gary—looks at me and goes, ‘Are you sure you wanna eat that? You should really watch your figure.’”

Dean froze. His smirk disappeared.

For a moment, he just stared at you, like he couldn’t believe the words had actually come out of your mouth.

Then his expression darkened, jaw tightening. “Tell me you’re kidding.”

You rolled your eyes. “I wish.”

Dean’s grip on his bicep tightened, his teeth grinding together. That prick. He had known from the start that Gary was a tool, but this? This was another level.

“So,” you continued, a mischievous glint in your eye, “I did what any rational, level-headed woman would do in that situation.”

Dean arched a brow. “And that was?”

You grinned, leaning in like you were about to tell him a secret. “I threw my drink in his face and left.”

Dean stared at you for a beat, then—He laughed.

A deep, genuine laugh that rumbled in his chest as pride swelled in him. “No shit?”

“No shit.” You grinned, clearly pleased with yourself. “Right in his smug, stupid, judgy face.”

Dean shook his head, chuckling. That’s my girl, he thought, though he would never say it out loud.

“But instead of coming straight home,” you continued, twirling your glass of water between your fingers, “I didn’t wanna deal with your I told you so—”

Dean smirked. “I would’ve said it.”

You shot him a look. “—so, I went to the Roadhouse instead. Had a few drinks, bitched about my failed date to Jo and Ellen. Ellen cut me off and called me a cab.” Dean huffed. That sounded about right.

For a moment, he just watched you, taking in the way you had perked up again, the lingering frustration in your eyes slowly melting into something softer.

You were here.

Not out with Gary. Not waking up next to some guy who didn’t deserve you. Not letting some self-important idiot tell you who you should be.

You were home. With him.

And as much as he wanted to tell you that he had been losing his damn mind all night, picturing you with someone else—he didn’t.

Instead, he leaned against the counter, arms still crossed, and smirked.

"Well," Dean said, tilting his head with a smirk. "At least you got a good story out of it."

"Yeah, I guess." You hummed, swirling the water in your glass. The initial amusement faded as your shoulders dropped slightly. Dean caught the shift immediately, his brows pulling together.

"C’mon, you can’t really be cut up about a guy with an Edward Scissor-hands haircut and zero game." He teased, hoping to pull you out of whatever downward spiral you were heading into.

It worked—your laughter bubbled out, a full, belly-deep laugh that made the tension in his chest ease. But then you sighed, the sound quieter this time, more pensive. "It’s not him I’m cut up about."

Dean watched you carefully as you traced the rim of your glass with your finger. "I just feel like I can never meet a good guy."

Something inside him twisted.

What about me?

The thought came unbidden, sharp and intrusive, and he shoved it down before it could take root. Instead, he nudged you with his elbow.

"That’s not true." His voice was lighter now, teasing again. "What about Mikey? The guy with the lisp?"

His grin widened as he mimicked a lisp, knowing damn well you’d dated the guy for barely two months in your sophomore year before his clinginess drove you up the wall. The look of horror that crossed your face had him biting back a laugh.

"Oh my God, Dean!" You gawked at him before landing a solid punch to his arm. "That is so mean!"

"Ow," he complained through his laughter, rubbing the spot you hit. "I’m serious, though! He was a real sweetheart.” He exaggerated the lisp again, barely dodging your next swing.

"I swear to God—" You huffed, turning to stomp off, but before you could escape, he caught your arm gently.

"Okay, okay, I’m done. Scouts honour." He held up three fingers in a mock solemn gesture.

You gave him a look—like you absolutely did not believe him—but still, with a huff, you reclaimed your spot opposite him and took another sip of water.

Then, almost absentmindedly, you sighed. "I mean, it has been a long time."

Dean’s brow furrowed. "A long time since what?"

You hesitated for a brief second before shrugging your shoulders, brushing it off like it wasn’t a big deal. "Since I’ve had sex."

Dean choked on his own damn saliva.

You frowned in concern, but he quickly waved you off, reaching for his whiskey to cover up the way his throat had suddenly gone dry.

You leaned back against the counter, lost in thought, completely oblivious to the war you’d just started in his head.

"I just—I don’t even need romance, you know?" You shrugged. "At this point, I’d settle for a little fun. I even bought new lingerie for tonight, just in case, and now"— you gestured vaguely to yourself, "totally wasted."

Dean swallowed—hard.

His mind was already in dangerous territory, but now it plummeted straight into the gutter.

You’d bought lingerie? For tonight?

His gaze instinctively flicked down for half a second before he caught himself, before he could let himself really think about what you were implying. Because if you had planned for tonight—if you were wearing it right now—

God help him.

The image hit him like a freight train. You, laid out in something lacey and delicate, something sheer enough to tease but not reveal, maybe even those crotchless panties you’d pointed out the other day in that damn store—his stomach twisted, his fingers curling around his glass with a little too much force.

And the worst part? Some other guy was supposed to see you like that tonight.

That thought sent something hot and possessive burning through his veins.

Dean exhaled sharply, gripping the back of his neck as he forced his gaze anywhere but at you.

"Gary didn’t deserve to see you like that." The words left his mouth before he could stop them, his voice lower than before.

You scoffed. "Yeah, well, no one else is seeing it either, so it really doesn’t matter."

It matters to me.

Dean forced himself to take another sip of whiskey, as if that would drown out the thoughts swimming in his head.

With a stretch and a yawn, you set your empty glass down and pushed off the counter. "Alright, I’m gonna head to bed. Thanks for making me drink water, Mom." You teased, because Dean was always more like a mother hen than a strict father.

Dean smirked, watching as you stepped closer. He expected you to give him a casual pat on the arm or maybe ruffle his hair like you sometimes did when you were feeling particularly annoying.

Instead, you leaned up on your toes and pressed a kiss to his cheek.

Or, at least, that’s where it was meant to land.

At the last second, whether it was the whiskey in your system or just bad aim, your lips caught the corner of his mouth.

You gasped softly, your breath fanning over his lips, and then you giggled. "Shit—sorry."

Dean didn’t move. Couldn’t.

Because you were still right there, inches away, your body just barely brushing his, your eyes flicking down to his lips.

Something in the air shifted.

The easy playfulness between you dissolved into something else—something warm and electric, something that made the hairs on the back of his neck stand up.

Your smile faded, lips parting slightly as you lingered, hesitating just a second longer than necessary.

Then, before he could say a damn thing, before he could even think—

You leaned in again.

And this time, you kissed him.

It was soft at first, hesitant, your lips pressing against his in a way that felt like a question. Like you were giving him the chance to pull away, to stop this before it could turn into something neither of you could take back.

Dean’s entire body locked up. His mind screamed at him to push you away, to remind you that you’d been drinking, that this was just a moment of drunken impulse, that tomorrow you might regret this.

But then you pressed in closer, deepening the kiss, your fingers skimming up his arm, and his resolve shattered.

A low, quiet sound rumbled in his throat as he gave in. Completely.

His hands found your waist, gripping tight, pulling you against him as he kissed you back. And not just kissed you—devoured you. All the tension from the past few days, all the frustration, the longing, the confusion—it poured out of him like a damn breaking.

Your lips were warm, soft, intoxicating in a way no drink could ever compare to. He let himself get lost in it, let himself feel it—how perfect you felt against him, how natural this was, like it had been inevitable all along.

You sighed against his mouth, your fingers sliding up into his hair, and Dean groaned, tilting his head to deepen the kiss even further.

He didn’t know when his hands had moved, but now one was tangled in your hair, the other splayed against the small of your back, pressing you flush against him. And fuck, you felt good. Too good.

This was dangerous.

And when you finally pulled away, lips kiss-swollen and breaths unsteady, Dean couldn’t move. Couldn’t think. His heart pounded like a war drum; each beat a sharp, insistent reminder of the storm raging inside him.

He should say something. Do something. But every word he might’ve spoken tangled in his throat, choked by the weight of what had just happened.

“Woah,” you whispered, your voice barely more than breath. Your eyes flickered between his and his mouth, never quite settling, like you were just as caught in the moment as he was. Your cheeks were flushed, heat radiating from your skin, and the ghost of your breath still lingered against his lips, dizzying and sweet.

Dean didn’t move. Didn’t dare move. The air between you crackled, fragile and electric, holding him captive in a moment he wasn’t ready to break.

He was waiting for you. Like always.

Your breath ghosted against his lips, and that was all it took.

You kissed him again, this time with more heat, more purpose, fingers tangling into the front of his shirt as you pulled him in. Dean let out a rough sound—somewhere between a groan and a sigh—before his hands found your waist, gripping tight as he backed you up against the counter. The edge dug into your lower back, but you barely noticed, too caught up in the way he was pressing into you, solid and warm and overwhelming in the best way.

His hands slid down, grasping the backs of your thighs, and before you could fully process it, he lifted you effortlessly onto the countertop.

A surprised gasp left your lips, but Dean was already there, swallowing the sound as he kissed you again, deeper, slower, his fingers digging into your hips. You pulled him in, locking your legs around his waist, desperate to feel more of him, and his hands wandered—exploring the soft, bare skin of your thighs, gliding higher, pushing the hem of your dress up as he went.

He trailed kisses down your jaw, moving to your neck, and when his lips found that one spot—the spot—you let out a soft moan, your head tipping back instinctively.

Only to smack it straight into the cabinet behind you.

The entire moment shattered.

You winced, immediately bringing a hand to the back of your head. Dean jerked back, eyes wide with concern.

“Shit—are you okay?” He cupped your jaw, scanning your face for any sign of real pain.

For a second, you just blinked at him—then, out of nowhere, you started giggling.

Dean frowned, still searching your eyes, but when you kept laughing, it broke him. He snorted, shaking his head, then let out a deep, full-bodied chuckle, forehead dropping against your shoulder.

“Jesus, sweetheart.” He pulled back, still grinning, rubbing a hand down his face. “That’s gotta be a sign, right?”

You sighed dramatically. “That the universe hates me?”

Dean smirked, his hands settling on your hips. “That you’re not sober enough for this.” His answer was loaded, a heavy realisation for himself that you were in no state of mind to be making any rational decisions right now, and that he should've known better than to take advantage of that.

You pouted slightly, but you both knew he was right. Still, there was something soft in his expression as he helped you down, steadying you with warm hands on your waist. The moment your feet hit the ground, you swayed a little, still a bit disoriented.

Dean caught you instantly. “Okay, yeah. You need to lie down, sweetheart.”

You groaned but didn’t fight him as he led you to your room, making sure you didn’t trip over your own feet. Once you were settled, he disappeared briefly before returning with a glass of water and a bottle of Tylenol, setting them on your nightstand.

“You’re a saint,” you mumbled, already sinking into the mattress.

Dean huffed a laugh. “Not quite. Just don’t want you becoming a pain in my ass in the morning when your head’s pounding.” He said as he helped pull off your shoes and settled you under the covers.

You cracked one eye open, looking at him with something unreadable, something soft. “Could never hate you, Dean.” You mumbled half asleep.

He looked at you, lingering for a second too long. Then stood, with a small exhale.

“Call me if you need anything.” He told you as he walked to the door. You hummed your acknowledgment, and with that, he left, shutting the door quietly behind him.

Dean barely made it to his own room before he collapsed onto the bed, dragging both hands down his face.

What the fuck just happened?

The feel of you, the taste of your lips—it was burned into him now, like some kind of cruel brand.

It was just a kiss. Just a few incredible, amazing kisses. But now he knew for sure, no one would ever compare now.

And that thought terrified him.

Because tomorrow, you might not even remember. And if you did, would you be embarrassed? Regret it? Or worse, hate him?

Dean stared up at the ceiling, jaw tight, mind racing.

Yeah. He was so fucked.

AN: There we have it folks, the first chapter! It was a long one 😅 I know, but I'd love to hear your thoughts/feedback etc ❤️

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Next Time...

Your breath hitched, but you forced yourself to stay still. No sudden movements, no giving anything away. But then your gaze betrayed you—just for a second, barely a flicker—dipping down to his mouth. Shit. Because now you could feel it again. The way he kissed you, rough but deliberate, like he had wanted it. The taste of whiskey, the heat of his hands, the way his fingers had curled into your hips like he was holding on for dear life. Dean cleared his throat. Stepped back. "I’m gonna head to the store," he said, too casual. It took a second for the words to register. "Oh. Yeah, okay." He hesitated—like he might ask you to come with him—but then he smirked instead, lips twitching. "Would’ve invited you, but, uh… You kinda look like the walking dead. Don’t want you cramping my style.” Your head shot up, glare locked and loaded. "Ass." Dean just grinned. "Try not to die while I’m gone." Then he was gone, the door clicking shut behind him. The silence that followed was deafening. Your fingers tightened around the coffee mug as you exhaled, long and slow, staring at the door like it might offer some kind of answer. Yeah. You were so screwed.

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s0urw00lf · 27 days ago

Text

One of those days

Pairing: Sam Winchester x reader, Jo harvelle x Dean Winchester

Warnings: mentions of unavailable parents

AN: I'm so happy with this! I love the idea of teenage Sam x reader and teenage dean x Jo doing normal teenage stuff. I just wanna write a whole bunch of these so if you have any requests please send them. Also I’m trying out new writing formats to see what I’m gonna be permanently going so that’s going well. (im writing this after i finished the fic that’s why it doesn’t match the title)

It wasn’t often that all four of you were at Bobby’s all at the same time, but when it did happen you made the best of it.

Bobby had told you and Jo about a time he took Sam and dean fishing and how dean annoyed and pestered Sam the entire time. Much to your surprise, the two of you never knew that Bobby had a huge pond on his property and when you asked why you never heard about it Bobby replied “cuz I wasn’t putn’ up with your complaints about the bugs”, making Sam and dean snort and you and Jo send them glares.

“We should go” Jo says from deans side once Bobby headed to bed. You raise your brows in confusion running your hands through Sam’s shaggy hair “go where?” You ask. Jo sits up a little causing deans arm to fall from around her shoulder “Bobby’s pond. I mean we all can drive and it would give us something to do and give Bobby a break” the four of you looked among each other before dean spoke “not a bad idea”

You look at Sam who’s head was in you lap, he gave you a shrug in response “sounds like a plan, but i don’t have a swimsuit” you say. Jo sighs “just wear shorts and a bra”

Your cheeks redden in embarrassment, dean smirked seeing the perfect opportunity to tease you “oh come on don’t tell me you’re all shy about wearin’ a bra. We’re all adults, plus its nothing Sammy hasn’t seen before if that’s what you’re worried about”

“Dean!” Sam says before throwing a pillow at his brother. Before looking up to you with a smirk of his own “hes not wrong though” he teases raising his eyebrows. You throw you head back feeling heat seep over your body “kill me now” you groan, before looking back at them “fine but don’t be surprised when my abs look better than you guys’” you say jokingly. Sam and dean both scoff “ill give you one hundred bucks if you show up with abs”

You let out a loud laugh “ill take you up on that action”

Not long after that conversation you all retire to bed, you and Jo sharing a room and Sam and dean sharing the other. Much to your dismay but Bobby insisted that there will be no opposing gender room sharing and you all knew better than to argue with Bobby.

The next morning was a blur, you woke up excited and followed Jo down for breakfast, Sam and dean showed up a minute or two after the two of you, saying their good mornings. Sam pressed a kiss to your forehead before sitting down next to you, dean did the same but kissed Jo on the lips. They were more bold with their PDA than you and Sam but you didn’t mind.

When Bobby sat down placing the last of the breakfast he made on the table, conversation flowed easily as everyone filled their plates with food. “What’re you four gettin’ into today, i got a few jobs to help with” Bobby asked biting into bacon. Your eyebrows raised in surprise “your goin on a hunt?” You asked cutting Into the pancake on your plate. Bobby shook his head “no just some research and calls to make.” You nodded in understanding taking a sip of your orange juice. “We’re going to that pond you mentioned last night” Jo answered his question.

Now it was Bobby’s turn to raise his eyebrows “the pond? Ain’t nobody wanted to go there in years” he said. Dean swallows a bite of his pancake before speaking “so it’s out of commission?”

Bobby snorts “no, i take care of my property, just surprised you’d wanna go” he said. Sam finally spoke from beside you “sounded like something fun to do instead of sitting around all day again”

Bobby nodded in understanding, before turning his attention to his food, and the four of you did the same.

The pond was a lot more well kept than you imagined, it was about a 10 minute walk from Bobby’s even though your and jo were sure you could’ve made it faster if you trusted your instincts and not the two bickering brothers.

You and Jo carried the towels and blankets and Sam and dean carried the chairs and cooler filled with drinks and snacks. The four of you worked to set up your sitting area, before removing the extra clothing articles.

You turned to Jo who handed you a water before glancing at your stomach “looks like dean owes you” she says loud enough to catch deans attention, he then looked at your stomach and groaned, you smirked “scarf to over Winchester” you say holding your hand out.

Dean reaches into his pocket and pulls out the one hundred dollar bill and slaps it into your hand before glaring at a cheezing Sam “you couldn’t have warned me?” He asked. Sam shrugs “one day you’ll learn not to make stupid bets. Even jo has abs, why wouldn’t she?” He asked guesturing to your smirking face. Dean looks between you and Sam. “My own blood is against me, what has the world come to” he muttered shrugging off his shirt.

Sam and dean of course were the first ones in the water, while you and Jo sat on the towels painting your nails. Jo had shown up with a case full of nail polish and promised to paint your nails eventually. The boys splashed around in the water laughing and shouting.

You felt so content in this moment, wearing a small smile as you watched them, careful not to move too much to avoid a scolding from Jo. “This is so… normal. It feels illegal” you say almost to yourself.

Jo turns her attention to you briefly and then to the brother in the water “it is, you’d never guess we’ve ever held a gun before” she joked. You laughed, as she finished up your hand, a large shadow covered the both of you, and drips of water pelted against your skin, “Sam, move your getting me wet.” You say trying and failing to push him out of the way “nope. We came here to swim. So we’re swimming.”

You looked up to Sam’s smirking face, you quickly stood up despite Jo’s protests to let your nails dry. You took a few steps back, ready to bolt as you pleaded for Sam to let you be. From behind Sam you see dean pick Jo up causing her to scream and throw her into the pond, letting out a victory laugh.

The adrenaline in your veins made you take off in a sprint in the other direction. “Run y/n!” You hear Jo shout from the water. “Get er Sammy, put those long legs to use” dean shouts clapping his hands.

Realistically you knew Sam could catch you with ease. But that’s what made it so fun was the unexpectansy of when he’d stop going easy on you.

Somehow you managed to stay out of his grasp long enough to reach where dean was standing right on the bank of the lake.

You ran behind him putting him between you and Sam, you watch him from over deans shoulder, his eyes were on dean, having a silent conversation before he looked at you “bad move baby” he said.

And before you could take of running again dean moves out of the way and Sam quickly grabs you and throws you.

You scream before hitting the water, you swam back to the surface with ease.

Making eye contact with the smirking brothers, when an idea popped into your head.

You hissed “Sam i think i hurt my foot” you say, Jo immediately catches onto your act ‘worriedly’ swimming over to you “what are you okay?” She asks urgently.

You shake your head “no it really hurts” you say forcing tears into your eyes.

Sam and deans eyes widen, scared that you’d actually been hurt. “Jo help her over here” Sam says, holding out his hand. Jo nods “helping” you swim to the boys.

“Dean give him a hand would ya?” Jo says feigning worry. You reach for both of their hands and quickly your expression shifts “gotcha” you say pulling them into the water with he help of Jo. The two of you laugh in success giving each other high fives.

The rest of the day was spent like that. Jumping in and out of the water, eating and drinking all of the snacks until the four of you finally decided to go home.

When you got back Bobby wasn’t home, you’d found a note saying that he’d be out until later that night. The four of you took showers and got changed before meeting up in the living room to watch a movie that nobody stayed awake for.

You were the last to fall asleep, against Sam’s chest. You took a peek at dean and Jo who were sprawled out over the smaller couch, breathing in sync.

Then you looked to Sam’s sleeping face. There wasn’t an ounce of worry in his features, he just looked completely at peace. You wished life could always be like this.

In the only house you’d ever grown to know as home, the boy you loved and the friends you’d grown up with all exhausted from a day of being actual teenagers and not because of a dangerous hunt. But it wouldn’t. And somehow you weren’t mad because that’s what made these moments all the more special.

SPECIAL ADDITION

When Bobby got home it was abnormally quiet, there was no way the four teenagers were still at the pond. But the lack of noise began to convince him otherwise. That was until he heard the tv from the living room. He followed the sound, only to see the four sleeping teenagers taking up the entire space of both couches only leaving one chair open. A rare gentle smile crossed Bobby’s face. They aren’t his kids, he knows that but every time he got to see them he felt like in a different world they might have gotten to be.

Seeing them like this reminded him of when they were kids, all tired out from running around outside all day and curled up into one bed. He was glad he could provide some sort of normality for the young teens who’d seen entirely too much horror for their own good.

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