Chat, I Think I Found Dean. (This Is A ‘68, But It’s Close Enough!!!)

Being a writer is basically emotionally bonding with fictional people and then ruining their lives for fun.

Jensen Ackles as Soldier Boy THE BOYS (2022) | 3.08 – “The Instant White-Hot Wild”

only Kendrick could get tumblr talking about the super bowl

men that moan while eating pussy go to heaven

"likes mean nothing on tumblr" you're sending me a little heart. that's not nothing it's your heart. look here's one for you <3

𝓴𝓲𝓭𝓼? D.Winchester

you’re nursing a beer, your legs pulled up to sit cross-legged as you lean back on your palms. dean’s beside you, his own bottle dangling loosely in his fingers. his knee rests against yours, this simple, casual point of connection, but it’s enough to ground you. his shoulders are relaxed, his legs stretched out long, but there’s something... off. you can feel it in the way his gaze keeps drifting, how he’s not quite looking at you or anything in particular. he’s lost in his own head, and you’ve been with him long enough to know that’s rarely a good thing.

“you’ve been quiet tonight,” you say, finally breaking the silence. your voice is soft, not accusing, but the words seem to snap him out of whatever spiral he was falling into. he glances at you, his green eyes flickering in the dim light, and he huffs out a little laugh. it’s small, almost self-deprecating, and he looks away again, his jaw tightening.

“just thinkin’, sweetheart,” he murmurs, taking a swig of his beer.

you tilt your head, watching him. “about what?”

he hesitates, running his free hand through his hair, and the gesture makes your stomach tighten. whatever it is, it’s big. he’s not usually this careful about his words—dean winchester isn’t careful about much, period—but right now, he looks like a man standing on the edge of something.

“can i ask you somethin’?” he says, finally, and his voice is quieter now, more raw.

“of course,” you reply immediately, setting your beer aside. you shift closer, your knee pressing more firmly against his, your hand resting on the cool metal of the car between you. “what’s on your mind?”

he exhales slowly, staring down at the bottle in his hands. for a second, you think he’s not going to say anything. then, all at once, the words come out.

“you ever think about havin’ kids?”

the question hits you like a punch to the gut—not because it’s unwelcome, but because it’s so unexpected. you blink at him, your lips parting, and he finally looks at you, his expression guarded. like he’s bracing for you to laugh at him, or worse, to shut him down completely.

“kids?” you repeat, just to make sure you heard him right.

“yeah,” he says, his voice gruff, like the word’s hard for him to get out. “like... not right now, obviously, but... someday. you ever think about it?”

your mouth opens, then closes. you glance at him, searching his face for any clues about where this is coming from. it’s not like dean’s ever been the white-picket-fence type. hell, you’re not even sure if you’re the white-picket-fence type, given the life you lead. but there’s something in his eyes, something vulnerable and almost... hopeful, that makes your chest ache.

“i don’t know,” you say honestly. “i guess i haven’t thought about it much, with everything going on. it’s not exactly easy to picture that kind of future, you know?”

he nods, like he was expecting that answer, but there’s still this shadow of disappointment in his expression. “yeah. yeah, i get that,” he mutters, tipping back his beer for another sip.

you watch him for a moment, your mind racing. he doesn’t bring up stuff like this lightly—hell, he barely even talks about his feelings unless you pry them out of him. but this? this is something he’s been holding onto, turning over in his mind, and now he’s laid it at your feet like some kind of fragile offering.

“why are you asking?” you ask gently, leaning closer. “is this something you’ve been thinking about?”

he lets out a low laugh, but there’s no humor in it. “yeah,” he admits, running a hand down his face. “i don’t know, it’s stupid. just... sometimes i think about what it’d be like. teachin’ a kid how to throw a football. takin’ ‘em for a drive in baby when they’re old enough. tryin’ to be the kind of dad mine never was.”

the confession is raw, almost painful, and you feel it settle heavy in your chest. dean’s voice drops lower, like he’s afraid of saying it out loud. “i mean, i know it’s a pipe dream, with the way we live. but... if it ever happened, you know? with you... i think i’d want that.”

his words hang in the air between you, and your heart stutters. with you. the way he says it, so quiet, so certain, makes something twist inside you. you reach out, your fingers brushing his arm. he looks up at you, his expression cautious, like he’s waiting for you to tell him he’s crazy.

“dean,” you say softly, “you’d be an incredible dad.”

he snorts, shaking his head, but you tighten your grip on his arm, making him look at you. “i mean it,” you insist. “you’re already so good with sam, and jack... hell, you take care of everyone around you, whether you realize it or not. you’ve got more love in you than you give yourself credit for.”

his jaw clenches, and he looks away, but not before you catch the flicker of emotion in his eyes. “you really think that?” he asks, his voice barely above a whisper.

“i know it,” you say firmly, leaning in closer. “and if that’s something you want... someday... then yeah. i think i’d want that too. with you.”

his head snaps toward you, his eyes wide, and for a second, he just stares at you. then, without warning, he leans in, his hand sliding to the back of your neck as his lips crash against yours.

the kiss is desperate, messy, like he’s been holding himself back for too long and finally let the dam break. his fingers thread through your hair, holding you close as his mouth moves against yours, hot and demanding. you gasp into him, your hands grabbing at his shirt, pulling him closer, needing him like you need air.

his tongue sweeps over your bottom lip, and you open for him, letting him in. he groans into your mouth, the sound vibrating through you, and it’s like a switch flips. suddenly, you’re climbing into his lap, straddling him as his hands grip your hips, pulling you flush against him. the heat of him, the way his stubble scrapes against your skin, the sheer wantpouring off of him—it’s overwhelming in the best way.

he breaks away for a second, his forehead pressing against yours as you both catch your breath. his hands are still on your hips, holding you there like he’s afraid you’ll disappear. “you have no idea how much i love you,” he murmurs, his voice rough and low, sending shivers down your spine.

“i think i have a pretty good idea,” you tease, your lips brushing against his as you speak. he laughs softly, the sound muffled as he kisses you again, slower this time, but just as consuming.

the future might be uncertain, but right now, with dean’s arms wrapped around you, his lips on yours, you think maybe, just maybe, you’ve found something worth holding onto.

"The revolution is about to be televised, you picked the right time but the wrong guy" - Kendrick Lamar, Half-time show 2025

02. takes one to know one

ᯓ★ story index abt, you join your new friend, outlaw!dean, in a little game of cops and robbers. warnings, robbery, guns, suggestive language, sprinkle of angsty hidden feelings, there's only one bed couch (more of that in prt3!!) 2.7k words

The sheriff had a lot more going on than just civil duties, the vast ranch set picturesque before you can attest for that. The house itself is massive, pure white siding glowing in the moonlight. Beyond that, a sleek brown barn cuts into the night sky. From where you and Dean sit, crouched behind one of the dozen jagged shaped trees that line the outskirts of the property, it looks deceptively peaceful. 

But you know better.

This stash of gold Dean assures you is hidden within those walls, isn’t gonna be an easy swipe. Guards patrol the quiet ranch, a few are pacing the front as you watch and search for a blindspot. 

“You sure about doin’ this, darlin’?” Dean drawls in a hushed whisper, his eyes light and playful, almost daring you to say no. 

Your narrow-eyed gaze goes toe-to-toe with his, your lips curling into a smile. “I was born sure, Winchester.” you quip, not missing a beat. 

Dean’s husky voice drops lower, momentarily lacking it’s usual cocky drawl, “you just stick to the plan, alright? You do that for me ‘n we’ll be swimmin’ in gold before sunrise.”

You rolled your eyes but couldn’t ignore the steady thrum of adrenaline in your veins. The plan—Dean’s plan—was simple enough: get past the guards, crack the safe and get the hell out of dodge. Simple, of course, was a relative term when talking about breaking into the home of a man who probably shot first and asked questions—never. 

“Remind me again why I agreed to this?” you tease, tucking your body closer to his. Your chin grazing his leather-clad shoulder as you both keep steady eyes on the ranch. 

Dean gives a quick glance, the moonlight catching in the green of his eyes. That pretty grin of his making a slow return. “Because you couldn’t resist me.”

Playfully hitting his arm, you shoot back at him, “or maybe I couldn’t resist the payday.” His eyes are back on you, lingering as his lashes slowly lift as he takes in your features at this newfound closeness. He merely offers a quiet hum in response, brushing against you as he shifts to hand you a small set of lockpicks. 

“Figure, with the way you work a cue stick,” he mumbles, voice low and as teasing as his eye contact, “you got this part handled.” He places the small box in your hand, clasping his large hands on either side of yours as he smirks, “And I’ve got a knack for getting into trouble. Perfect match, huh?”

Before you could reply, the sound of boots crunching on gravel causes both your heads to snap towards the ranch. A guard passes by, just a few yards away, his rifle glinting in the moonlight. Dean’s playful demeanor is entirely consumed by a sharp alertness that makes you wonder just how many times he’s been in a situation like this. 

The stillness passes as the guard meanders away, the sound of his boots dying out in the quiet of the desert. Your new partner’s shoulders relax at the false alarm. That lopsided smile playing at his lips again as he tugs you closer, his nose brushing your cheekbone.

“Showtime, baby.” Dean whispers, pulling back with a wink as two fingers reach up to tip his hat. 

The two of you slip through the shadows of the ranch like ghosts. A mere step between your bodies as you stick close to the edges of the house where the moonlight doesn’t touch. Dean leads, moving with surprising stealth for someone so broad. Every now and then, he glanced back at you, giving a little nod of reassurance. His focused eyes softened slightly each time he turned back. 

Moving through the property was easier than you thought, but Dean’s uncanny sense for danger has made it so. He pauses just before a light sweeps over your path, his hand shooting out to pull you into the shadow of a nearby tree when he detects movement before you do. The guards are predictable, too. Their routes timed perfectly to give just enough room to duck behind a stack of barrels or hop over a fence. One guard left his post at the backdoor, leaving an opening to slip into the darkened home. 

You follow Dean’s silent lead of avoiding spots of creaky floorboards as you step inside, pulse thrumming with adrenaline. As you move through the dark, Dean peeks through doors with deliberate slowness. You watch between him and the back door, until he’s motioning you over with the flick of a finger. 

The study was just as grand as you’d imagined—dark wood paneling, glass cases displaying expensive weapons and memorabilia. A massive desk cluttered with papers sits before two large windows. In the center space, a portrait of some grim-faced ancestor takes up most of the wall. 

Dean’s already hovering over it, inspecting the frame. The sharp edges of his side profile illuminated by the moonlight spilling in through the window. His eyes finally catch yours, nodding for you to come over, a sly grin on his lips as he leans down over your shoulder. 

“These rich sons of bitches are always so predictable.” He laughs dryly, “go on ‘n tug on that side of the frame for me, Sweetheart.” 

You don’t waste a second, pulling on the frame until it pops open. Swinging like a hidden door, revealing a built in safe on the adjacent wall. Pulling the small box of tools Dean gave you earlier, you get to work on the silver lock. The tumblers click softly as you go, each sound loud in the otherwise silent room. Dean stood behind you, close enough to hear his steady breathing. Keeping an eye on the door, his hand resting lightly on the gun tucked into his waistband.

“Got it,” you whispered after what felt like an eternity. The safe door swung open, revealing stacks of gold bars that gleamed even in the dim light.

Dean let out a low whistle. “Now that’s a sight.”

You quickly began transferring the bars into the canvas bag Dean had brought, your heart pounding with a mix of excitement and fear. 

This plan of his had gone so smoothly, too damn smooth to be more accurate. 

Just as you finish zipping the bag, heart still hammering in your chest, a muffled voice barks from the hallway, “check the study!”

Dean’s jaw tightened as he reached for the gun tucked in his belt, but the door burst open before he could draw. Two guards stormed in, their guns trained on you both.

“Drop the bag,” one of them ordered, his eyes narrowing.

Your mind raced as Dean slowly raised his hands, palms out in mock surrender. His smirk returned, cool and steady, as if staring down the barrels of two guns was just a typical Thursday night for him.

“Well,” he drawled, his gaze sliding to you. “Guess now’s a good time to make a confession.”

Your stomach dropped. “Dean—”

“I mean, might as well, right?” he continued, cutting you off. His smirk softened into something maddeningly sincere, his eyes holding yours even as the guards barked for him to shut up. “You’re the prettiest little thing I’ve ever seen. And if I were a better man, I’d have asked you on a proper date. Y’know, steak dinner and all that crap.”

You blinked, completely thrown, but before you could respond, Dean’s hand shot out, grabbing the desk lamp and hurling it at one of the guards. The heavy base struck him square in the face, and chaos erupted.

Dean didn’t hesitate. He ducked under the second guard’s arm, grabbing the man’s wrist and twisting it until the gun clattered to the floor. “Move!” he shouted at you, his voice sharp.

You didn’t need to be told twice. Snatching the bag, you bolted for the window, Dean hot on your heels. He shoved you ahead of him, glass shattering as you both tumbled through the opening and into the cool night air.

The shouts behind you were nearly drowned out by the pounding of your heart. Bullets whirl through the air, but Dean grabbed your hand, dragging you across the open yard and toward the safety of the rugged desert terrain ahead.

You didn’t stop running until the ranch was a distant glow behind you, your legs screaming in protest as you collapsed against a tree.

Dean slid down next to you, his chest heaving as he tried to catch his breath. A laugh escaped him, soft and incredulous. “Hell of a night,” he muttered.

A wicked laughing fit hurls out of you through panting breaths, reeling from the cooling adrenaline icing your veins. “You really had me for a second, y’know,” you manage through heavy breathes, “d’you mean any of that? Or was it all just part of your plan?” 

Dean smirked, taking off his stetson to run a hand through his messy hair. “Which part?”

“Oh, I don’t know,” you teased, biting your lip in mock-deep thought. “The part about me being the prettiest thing you’ve ever seen? Or the bit about steak dinners?”

Dean chuckled, leaning his head back against the tree trunk, lazily tilting to peek down at you through his lashes, “I told you I wouldn’t lie to you, didn’t I?” He’s doing it again—that smug little smirk—a sweet boyish charm that tempts your nerves in the most unfamiliar way. 

You turn away from his gaze, settling your eyes on the bag in your lap and letting your hair fall around your face to cover the blush that’s creeping in. “Mhm,” you hum into the quiet between, “careful now, cowboy. I might just hold you to your word.”

He doesn’t answer, and you pretend there isn’t a slight twist straining your heart for half a beat. Quietly, he places his hat back on. Pressing into the ground, he rises to his feet with a huff. Dean extends a hand, his eyes scanning the distance as you take his offer. 

Boots kick up dirt as you walk side by side down the dusty terrain. And for a moment—in the quiet of the desert, with the bag of stolen gold between you, the danger of the heist morphed with the dawn settling in the horizon. A warm toned thing, burning at the edges of your cold exterior, new nerve endings bleeding light between your thoughts of Dean and the feelings he keeps insighting. 

Trudging on, the sheriff’s ranch is out of sight. The weight of the gold was growing heavier, hanging from your shoulder. But you’d be damned if you let him carry it, not when it felt like grasping some essence of control. 

“So,” you drawl, kicking at a red rock, “you looked like a real professional back there. How long’ve you been sniffing out trouble like this?”

Dean shrugs, burying his hands in his pockets as he considers his words. “Sorta spent my whole life in some type of trouble.” he states plainly, voice quieter as he continues, “Been on my own a couple of years, give or take. Found the type of trouble I like best in all that time.”

You glance up at him, his skin soaking up the orange light peeking over morning clouds. The warmth of the hue makes his eyes impossibly green. Like the cactuses zig zagging your path, sharp and rich in color. “You like it? Being on the road?”

“Yeah,” he sounds unsure, pausing with his lips parted, “Most of the time, I do. It’s… simple.” His hands return, moving with each word, “No strings, no one to answer to.” 

You hum back, nodding in agreement. It’s a sentiment you can agree with, the same idea you've convinced yourself of for much longer than just a couple years. 

“But,” he sighs, eyes flicking across the landscape, “I miss my brother, Sam.” The name makes a smile creep onto his lips as he mutters, mostly to himself, “m’little Sammy.” 

There’s a softness on the name that makes your chest ache, “Why don’t you go see him, then?”

Dean hesitates, jaw tightening, “not that simple.” He let out a low breath, running a hand over his chin. “I don’t even know where I’d start. And if I ever tried to show my face to my old man…” His voice trails off, the words tangling in a wide-eyed huff that says it all in one motion. 

You part your lips to reassure him, daring to give the advice of it’s-never-too-late to a soul you know won’t take it. But, before you could he hummed a low, dismissive note. 

“Anyways,” he quips, a lazy grin returning to his face, “look at me, turning into a regular chatterbox. This your doin’, pretty girl?” His eyes find yours, but the usual playfulness isn’t as prevalent as it has been all night. In its place is something dark, trying desperately to work its way out. 

A look you know better than to pry at. 

Leaning over to nudge his shoulder, you offer a small smile. “Maybe I’m just easy to talk to.”

Dean’s grin shifts into something softer, but he doesn't answer. With a deep inhale his chin is up in the air again, eyes looking at anything but you.

 A splotch of brown you both assumed to be more rugged desert hills comes into focus—a vacant ranch tucked between scattered fields of jagged trees and cacti. The barn had collapsed, its frame a shadow of what it once was, but the house stood stubbornly, its roof intact and its windows dark against the rising sun. 

Dean raised his brows, eyes glancing over, “looks cosy.”

You scoff, giving him a worried look, “if your idea of cozy is ‘haunted ranch on the hill’, sure it is.”

“Better than sleepin’ out in the dirt,” he shoots back, already heading for the porch. He spins on the heel of his boots as he walks backwards, “‘sides, darlin’, if there’s a ghost around I’ll keep you safe.” 

With a wink that works a giggle out of you, Dean jogs up the creaky steps and disappears into the run-down house. 

 The inside is covered in a layer of dust and dirt, but there’s furniture scattered around—a worn couch covered by a sheet sits in an otherwise empty space. A creaky dining table in the kitchen, where you plop the heavy bag of gold, a cloud of grey puffing around it. 

“Not too shabby,” Dean coos, coming down a set of weathered stairs. “Just an old mattress on the floor with, uh, minimal stains and a whole lotta dust. Looks like we’ve got options.” He crosses the creaky floor until his boots are inches from yours. A smirk shining down at you, as his voice finds that teasing tone again, “Unless, of course, you’re afraid of ghosts.” 

Your eyes roll at his taunts as you cross your arms. “Please. I’m not afraid of anything.”

“Uh, huh,” his brows furrow, lips twisting with contemplation as his eyes dance across the curves of your face.

“Yes, huh. Cross my heart.” You swear with a reassuring nod. 

His eyes fall to the couch, and then back to the stairs before they settle back to you. His thoughts written in the smirk on his lips. “Mattress is kinda gross, actually. Couch could fit two—”

You cut him off, throwing your palm up with a humph. “Look, Cowboy, I may look the type but it takes a whole lot more than a game of pool and stealing gold to get me all cozied up on a dusty ‘ol couch in the middle of the desert.”

Dean barks out a laugh, holding his hands up in mock surrender. “Hey, hey—’m not suggesting a thing, little miss.”

You arch your bows with a “mhm,” the faintest hint of a smile tugging at your lips. Dean follows as you walk into the living room, discarding the sheet and plopping onto the cushion with a sigh. The couch dips under Dean’s weight on the opposite end. A quiet set in for a moment, comfortable and as warm as the growing heat of the sunrise. 

“Will say, though,” Dean sighs, his thighs sprawling over the soft surface as he relaxes into the creaky furniture, “I’d be a gentleman—”

“Shut up.” you shoot back, unable to hide the laugh that slips between the words.

hmmmmm should they boink in the next part???? hmm hm hmm

tags <3 @the-fandoms-onceler @a1ecmcdowell @titsout4jackles

dean should have ended up with cassie

she made him look 10x hotter

i said what i said

Not me absolutely fucking up my sleep schedule the last couple weeks cuz I’ve been trying to think of ways to make my little fics work