OFF DUTY
Sam Winchester x Reader x Dean Winchester
Word Count: 2.1K
Content Warning: Lighthearted comedy, platonic shenanigans, mild alcohol use, and playful chaos on the road with the Winchesters. No violence, trauma, or disturbing content. Contains references to pop culture (Buffy The Vampire Slayer, Bert and Ernie) Reader is gender neutral.
© ANNIEWINCHESTERR (2025). please, do not steal, copy or translate my works. thanks for reading!
Nobody warned you about this part of life on the road with the Winchesters. Not the small towns that blur into one another, the endless hours spent driving under the glare of headlights, or the motels that all somehow smell like old carpet and burnt coffee. Not the quiet moments, when the hunt is done and the adrenaline has faded, leaving only the hum of the heater and the distant creak of the walls.
It’s not all salt and silver bullets, not all terror and running through the night with knives in your hands. There are these… pockets of absurdity, little cracks where the world softens and you get to breathe. It’s the moments when Dean’s jokes make you roll your eyes, Sam’s quiet smirk makes you grin, and you realise that life on the road isn’t just about hunting monsters — it’s about surviving together, in every sense of the word.
And that’s when the fun starts.
—
The pub smells like old wood and fryer oil and beer that’s been spilled so many times it’s soaked into the floorboards permanently. The kind of place that runs a quiz night because there’s nothing else competing for attention — two dartboards with missing tips, a chalkboard menu that hasn’t changed in days, and a microphone that squeals every time the host clears his throat.
Dean loves it instantly.
“This place has character,” he says, which is hunter shorthand for they won’t cut me off.
You slide into a scarred table near the back, answer sheets curling at the edges. Sam orders food like he’s been fasting. Dean orders beer like it’s a sacred ritual. You lean over the clipboard when the host asks for a team name.
Before you can speak, Dean writes THE SCOOBIES in thick, unapologetic capital letters.
You stare at it. “We are not calling ourselves that.”
“Yes, we are,” Dean says. “You lost naming privileges forever when you tried to call us ‘quiz on my face.’”
“That was one time.”
“It was one time too many,” Sam says, already betraying you.
You sigh, resigned. “Fine. Scoobies. But if we’re doing this, we’re assigning roles.”
Dean grins. “Obviously.”
Sam doesn’t look up from the menu. “I’m Willow.” That’s unanimous. Settled. Biblical.
Which leaves you and Dean staring at each other across the table.
“No,” you say immediately.
Dean mirrors you. “Absolutely not.”
“You are not making me Xander.”
“You think I wanna be Xander?”
And there it is.The slow, dawning horror that one of you is going to have to accept being the human-shaped liability of the group.
“Xander has no powers,” you say. “He’s just… there.”
“He’s comic relief,” Dean snaps. “And emotionally repressed.”
“Sounds familiar.”
“Buffy carries the team,” Dean shoots back. “That’s me.”
Sam watches this all unfold like a tennis match, calmly sipping his drink.
The quiz starts mid-argument.
You’re still muttering about character arcs when the first round is announced, and that’s when you realise something is wrong.
Sam is answering too fast.
Not cheating-fast. Just… knowing. Ancient history. Literature. Science questions that sound like they were pulled from a doctoral exam. He barely hesitates, pen gliding like this is what he’s been training for his whole life.
Dean stares at him. “Since when are you this good at pub trivia?”
Sam shrugs. “I pay attention.”
By round three, other teams are watching you. By round four, you’re in the lead. Dean starts leaning back in his chair like he’s already won, arm slung over the back of yours, smug as hell.
The Buffy/Xander debate resurfaces every time the host says “Scoobies.”
You dig your heels in. Dean digs his in harder.
Neither of you wants Xander.
Years later — years — you’ll finally cave, and only because Sam, who has remained aggressively neutral this entire time, says quietly, “Dean’s the muscle. You’re the heart.”
Dean pretends not to hear it.
You come second overall. Dean complains like you were robbed. Sam apologises like he personally failed you. You don’t care.
Tomorrow you’ll leave town.
Tonight you’re just three people in a pub, arguing over fictional roles, drinking cheap beer, and pretending the world isn’t waiting for you outside.
—
It starts, as always, because you get bored.
Your motel room is doing that thing where it hums and flickers and refuses to let you forget you’re awake. The air smells faintly of bleach and burnt coffee. You try to lie still. You fail. Spectacularly.
So you grab your keys.
Sam opens the door in socks, hair damp, blinking like he’s still buffering. “It’s—”
“Late,” you say, breezing past him. “I know. I’m suffering. You’re complicit.”
Dean’s already on his bed, boots off but jeans still on, channel-surfing like his life depends on it. He looks up and immediately grins.
“Oh good,” he says. “Backup.”
You peer at the TV. “What is this?”
“Some movie no one’s heard of,” Dean replies proudly. “Which means it’s either terrible or a masterpiece.”
Terrible is an understatement. It is borderline sacrilegious.
The acting sounds dubbed even though it’s definitely in English. The lighting suggests someone lost a lamp halfway through filming. Ten minutes in, you’re already heckling.
“Oh my God,” you say. “Why is she whispering like that?”
Dean sits up. “WHY is he running toward the noise?”
Sam, arms crossed, squints at the screen. “That’s not how anatomy works.”
“You don’t know that,” Dean says. “Maybe lizard people have different bones.”
Around the twenty-minute mark, the tension hits a little snag. You nudge Dean, telling him to scoot over because you don’t have enough room, and suddenly it’s a full-on debate. Two small double beds, three people, and Dean throwing a fit because it’s his bed and, technically, he didn’t pay to share it. The next five minutes are spent bickering, him grumbling about space while you insist on survival-level elbow room.
“Nope,” Dean says immediately. “Not happening. I’m six-one, I need leg room.”
“I’m taller than you,” Sam adds. “And I’m not curling into a question mark.” You look between them. Then you smile.
“Oh,” you say, climbing up onto the couch like you’re about to conduct a symphony. “I have a solution.”
They both groan.
“No,” Dean says. “Whatever your idea is — no.”
“You push the beds together,” you announce. “I sleep in the middle.”
Sam blinks. “That’s… actually not the worst idea.”
Dean glares at him. “Et tu, Brute?” You really shouldn’t have taught him that — now there’s no stopping him from dropping it at every possible dramatic moment.
You clasp your hands. “I’ll provide emotional support.”
“You’re not helping at all,” Dean says.
“I am supervising.”
They drag. They shove. The beds scrape against the floor in a noise that absolutely violates motel policy. Dean grunts like he’s lifting a car. Sam tries to line them up precisely, muttering about symmetry.
You conduct the whole thing from the couch.
“Little to the left.”
“No, your other left.”
“Wow, teamwork. Growth.”
Finally, the beds meet. A lumpy, precarious truce. Dean flops down first.
You wedge yourself between them, blankets shared between all three of you like a peace treaty no one remembers signing. Sam adjusts the pillows with surgical care. Dean steals the remote.
“If I fall through the middle and die, I’m haunting both of you.”
The movie keeps playing.
The commentary softens as the hour stretches on. Your laughter fades into quiet snorts. Dean’s insults get lazier. Sam stops correcting the continuity.
At some point, Dean’s shoulder presses warm and solid against yours. Sam’s arm drapes loosely behind your head, not touching, just there.
You don’t move.
The TV flickers, but no one’s watching anymore.
Sleep sneaks up on you like it always does — slow, inevitable, unannounced.
You wake up twisted comfortably between them, beds still holding. Your face is buried in Dean’s chest — because apparently the perfectly good pillow on the bed wasn’t an option — and one leg is hooked over Sam’s like you’ve claimed him as part of the morning territory. Dean groans like the world personally betrayed him. Sam blinks awake and immediately apologises for stealing too much blanket, even though you’re clearly occupying half of his side anyway.
No one mentions the engineering feat.
No one asks why you didn’t go back to your room.
This is just how nights end sometimes.
—
Grocery shopping with the Winchesters only happens when one of you snaps.
Usually it’s Sam, staring down a week of diner menus and grease-soaked regret. Sometimes it’s you, craving fruit like it’s a moral emergency. Dean pretends he doesn’t care right up until someone suggests vegetables and then suddenly he demands input.
The store is fluorescent and mildly haunted in the way all grocery stores are after 9 p.m. The automatic doors whoosh open like they’re judging you. Sam grabs a trolley immediately, already in Logistics Mode. Dean wanders off within seconds, drawn to the snack aisle like a moth to a lamp.
You’re the one who picks up the bananas.
You don’t even hesitate.
You stick one in your ear and pivot slowly toward Dean, deadpan as hell.
“Hey,” you say. “Dean?”
He looks up from a wall of cereal boxes. Squints. Grins instantly.
“Oh no,” Sam mutters, clocking the situation too late.
Dean straightens, fully committing.
“Uh, hey, Ern?” he says loudly. “Hey, uh — Ern?”
You cup the banana dramatically. “What was that, Bert?”
Sam pinches the bridge of his nose.
Dean steps closer, lowering his voice like he’s trying to be reasonable. “You know you’ve got a banana in your ear, right? Bananas are food. You eat them. Not—” he gestures vaguely, “—that.”
You beam. “WHAT’DYA SAY, BERT?”
A woman in the produce section freezes mid-avocado.
Dean sighs deeply, then shouts. “WILL YOU JUST TAKE THAT BANANA OUTTA YOUR EAR.”
You match his volume perfectly. “I’M SORRY — YOU’LL HAVE TO SPEAK UP — I CAN’T HEAR YOU — I HAVE A BANANA IN MY EAR.”
The silence afterward is biblical.
Sam is already halfway down the aisle, pretending with his entire soul that he doesn’t know either of you. “I’m not with them,” he says to no one in particular. “I just — shop here.”
Dean is laughing too hard to stand straight. He wipes at his eyes. “Oh my God. Worth it.”
You finally remove the banana and drop it into the trolley like nothing happened.
Ten seconds later, Man! I Feel Like a Woman! comes on over the speakers.
Dean’s head snaps up.
“No,” Sam says immediately.
Too late.
Dean drops the cereal box, steps into the aisle, and starts moving. Hips. Shoulders. Full commitment. He spins the trolley like it’s a dance partner, strutting down the linoleum like he’s headlining a Shania Twain tour.
You clap. Obviously.
“WORK IT,” you shout.
Dean points at you like you’re his biggest fan. “Let’s go, girls!”
Sam stands there, holding a bag of spinach, looking like the most exhausted babysitter alive. “We talked about this,” he says flatly. “We talked about public spaces.”
Dean does a dramatic hair flip. He does not have long hair. It doesn’t matter.
Someone’s grandma cheers.
You’re crying laughing by the time Sam physically grabs the trolley and steers it away from the spectacle. Dean bows as if to an audience. The song fades out. The world keeps turning.
Later, you actually check out. There are vegetables. Fruit. Real food. Dean sneaks candy bars onto the conveyor belt when Sam isn’t looking. You let him.
—
At the end of the day, when the motel lights flicker off and the hum of the Impala drifts through the parking lot, it hits you — this is what family feels like. Not the neat, picture-perfect kind that gets written about in greeting cards, but the messy, loud, unpredictable kind that shows up in the middle of the night with extra blankets, pizza, or a badly timed joke just to make you laugh.
The road isn’t easy, and the hunts are never simple, but these are the people who have your back when the world is trying to eat you alive. Who let you be yourself without judgment. Who argue over trivia team names and grocery aisles and improvised drama like it actually matters, because it does, in its own small, ridiculous way.
Monsters will come and go. Salt will burn. Nights will be long. But here, in these strange, fleeting moments between hunts, you’re home. Not because of the walls, or the motel beds, or even the Impala, but because of them. Because this — this madness, this laughter, this ridiculous, beautiful chaos — is family. And somehow, that makes all the rest worth it.
Tags: @fratbrochrisgf @biancalinkas @littlebitb @madslxz @witch-of-letters @ohtobeahobbitgal @thewinchesterwench
If you’d like to join my taglist for future fics, feel free to send me an ask or leave a comment on my taglist post. I’d love to keep you updated!
A/N: Y’all deserve some comedy for the angst I’ve been serving relentlessly. I actually loved every second of writing this so I hope y’all like it!
