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artyandink · 6 months ago

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𝙾𝙻𝙳 𝙵𝙰𝚂𝙷𝙸𝙾𝙽𝙴𝙳 | bartender!dean winchester

Summary: Dean Winchester needs a job after his little brother left for Stanford, and he’s good at mixing drinks. You happen to work at Harvelle’s Roadhouse, which is the place he chose to work at. He finds a family. He finds a new life. But he also finds you. But you have problems of your own.

A/N - My first reader series, do make sure to comment and/or reblog feedback. Set with S1/2 Dean cause I love our baby boy 😁 and pretend group chats exist on old phones lol

SERIES MASTERLIST

one - gin and tonic

Harvelle’s Roadhouse.

It was rather a homely place, with the constant chatter of the different people that stop by for a quick drink, the tunes playing from the jukebox, followed by the clatter of pool cues that ended with the clinking and tappings of glass on glass and glass on table. The place was lit with warm light, bulbs hanging from the ceiling and the distinct musk of whiskey, vodka and tequila that burned people’s throats without the liquid even going down them. It was chaotic.

It was home.

You shared a look with Jo, who was busy serving a passer-by with a cheery smile on her face while Ellen was walking a first-time drinker through the right options, rather than ordering fifty at once and getting so hammered that you three would have to drag them off the floor of the bar and mop up their sick. You sneakily poured a shot for yourself, downing it before anyone but Jo had a chance to see what you were doing and washing out the shot glass. You were a bartendress, you could hold your liquor without a problem.

“Hey.” Jo nudged you after serving a whiskey and nodded to the opposite corner, where a clearly wasted man was trying to grope a poor girl passing by, grabbing her wrist and trying to tug her back with slurred words and bedroom eyes. The sight made your blood boil and your hand itch to reach for the baseball bat that laid behind the counter. “Reckon we should 86 ‘em?”

“I don’t think there should be reckon anything.” You frowned, pursing your lips. “Dude needs to go.” You kept your eyes on the guy, while your co-worker and good friend Benny approached you two with narrowed blue eyes and cap pulled low over his brow.

“Everythin’ alright here, darlings?” He drawled, and his eyes follow the trajectory of yours and Jo’s until he finds the drunk man across the room, a small hum of acknowledgment leaving his mouth. “Y’all can relax. I’ll handle this-”

“Hey, pal?” A hand with a silver ring on it gripped the shoulder of you guys’ target, the voice sounding a bit stern. The hand was connected to a leather jacket-clad arm, which was worn by a man who was about 6’ 1” in height, and rather devastatingly handsome. He had sandy blonde hair and startling green eyes, with pouty pink lips and rather a defined jaw. He was built well, and clearly benched or at least worked out. You found yourself staring at his easy smile that masked some well-controlled anger towards the guy. “The lady doesn’t want you touching her. I’d hate for that handsome face of yours to be ruined.” The sarcasm in the comment got you grinning, and also got Benny over to the scene to roughly take the drunk dude’s hand off the girl, pulling him up and throwing him out while Jo ducked out from the counter to take care of the poor thing and get her a drink.

You found the stranger who helped Benny out at the counter, eyes twinkling as he looked into yours with a grin that twinkled in the light of the flickering bulb above your heads that you quickly twisted and got properly working again. “Harvelle’s Roadhouse, what can I get you today?” You greeted automatically, giving the man a smile that held a hint of gratitude. Gratitude, yes, but your eyes betrayed knowing. You could see the lost look in his eyes, almost searching for a place, and your heart went out to him. You knew all too well how that felt. All too well.

“A job, hopefully.” He answered with a nervous chuckle, looking down and then up at you with his eyes scanning you almost imperceptibly. “Saw the hiring sign outside, thought I might try my hand here.”

“Well, your hand got lucky.” You grinned, tapping the counter twice to get Ellen’s attention while she was serving another customer. “Can I get a name?”

“That’d be helpful.” He smirked, then put out his hand for you to shake. “Dean Winchester.” You shook his hand while giving him your name in return, Ellen stepping to stand beside you.

“We got a new hire, huh?” She chuckled, shaking Dean’s hand. “Hi, I’m Ellen. I run the place.”

“Dean. Winchester.” The name made Ellen’s eyebrows raise in surprise, and yours did too in curiosity. She seemed to know Dean, and that intrigued you.

“You’re one of John Winchester’s boys.” Ellen noted, which made Dean look between you and Ellen, his eyes lingering on you for a moment longer.

“You know my old man?” He asked curiously, his emerald eyes almost giving a puppy-dog look as he addressed Ellen, his hands clasped on the counter in front of him.

“John stopped by often, was like family once.” She nodded with a soft smile. “Also knew you through Bobby, also a regular. Said you were a good kid. Well, I guess you’ve met our golden girl.” Ellen gestured to you with a tender hand, patting your shoulder. “She makes the meanest Cosmo around. She’ll show you ‘round, get you acquainted with the rules and regulations and also introduce you to the others working this shift. Take him through it, sweetie.” Ellen moved away to serve more customers, while you lifted up the gate to the counter to allow him inside. Dean stepped in, already looking mesmerised by the atmosphere and simultaneously the large selection of hard liquor to get through. Jo and Benny left their posts, strolling over to join you two.

“A new hire.” Benny held his hand out for Dean to shake. “Benjamin Lafitte, brother, but call me Benny.” Benny took one look at shared a look with you; he saw it too. The need of a metaphorical map in this stranger’s minuscule mannerisms. He was in need of support, and even though you two didn’t know what for, you were happy to give it.

“Benny, got it.” Dean shook Benny’s hand with an easy grin. “Dean Winchester, but call me Dean.” He turned to Jo, his eyes flicking up and down her as he’d done with you, and you noted that it might be a natural thing for him. Checking out pretty ladies. “And who might you be?”

“Jo.” She shook his hand, flicking her blonde hair out of her face.

“Don’t be shy, Joanna Beth.” Benny teased, piquing Dean’s interest.

“Joanna Beth?” He repeated with raised eyebrows and a small smirk.

“It’s just… Jo.” Jo chuckled, swatting Benny’s shoulder. “Ignore him.”

“Duly noted.” Dean nodded, then Benny took his shoulder. Their eyes met, and Benny’s lips twisted into a smirk.

“One question for you, brother.” Benny drawled in his slow accent, his eyebrow raising under the cap. “Can you handle your liquor?”

“I can mix ‘em and drink ‘em, if that’s what you’re getting at.” Dean answered confidently, that devilish grin still on his face.

“Then you’ll fit right in.” You clapped his shoulder- his surprisingly muscular shoulder - and brought him over to show him the ropes. “Initiation’s gonna be fun.”

Later on, when the Roadhouse closed up and all the patrons were out, we gathered around the bar. You introduced Dean to your resident party animal, Ash, who was busy being a genius in his room out back. You all were relaxing with glasses of whiskey, making sure to make Dean feel at home. He fit in well, and had instantly become a popular with the ladies and Benny’s new partner in crime. Jo pulled out ten shot glasses, which made everyone but Dean whoop and clap their hands.

“Time for initiation, young man.” Ellen cackled, taking out a bottle of bourbon, scotch, hard whiskey, vodka and tequila. Dean stared at the five bottles in confusion as they filled up the shot glasses, two shots per bottle in the order described.

“Complete this test and you’re officially one of us.” Jo smiled, pushing all of them forward in a neat line while you prepared a stopwatch. Dean registered all of the five drinks lined up with a small smirk, and then glanced around at the others in the room.

Had everyone done this before?

The prospect was thrilling. Getting to be part of a surrogate family that seemed to be so… happy. Especially since Sammy had left for Stanford and his old man wasn’t the keenest where he was concerned, being a part of this was all he wanted.

“All you have to do is down all ten of these shots within forty five seconds.” You grinned, holding up the stopwatch. “Level one is bourbon. Then scotch. Then you have hard whiskey, but not too strong. After that’s some tangy vodka, and you have the final level. Our strongest tequila.”

“Strong as hell. Beauty’s got a kick.” Benny whistled, then nudged you. “Remember when Bela thought she could handle more of that stuff and was passed out on the pool table five minutes later?”

“Like it was yesterday.” You laughed, then gestured to Dean. “Take your mark, soldier.” Dean stepped up to the counter, assessing the situation with careful, determined green eyes. They always seemed to captivate you. That and his winning smile. He’d taken off his leather jacket, which was over a blue flannel and grey undershirt. He had a boyish charm to him that you couldn’t help but warm up to as well. “Ready?”

“Born ready.” He nodded, mentally preparing himself as he took a deep breath, waiting for his cue. Then when there was the loud shout of ‘go’, he started slamming back the shots, the liquid burning his throat as we went. The bourbon and scotch were easy, the whiskey went down quicker than expected, but he faltered slightly on the vodka, the tang making one of his eyes close instinctively.

It felt like a goddamn barrage of sour candies at once.

However, Dean braved it and threw back the other, picking up the tequila and downing the first one. The burn made him cough and shake his head as the room went off kilter for a moment, but he grabbed the other and took it down in half a second before slamming the glass down on the table. You stopped the timer, and Dean straightened up as he got what felt like a million claps on the back. He met your eyes with a wide grin that matched yours, gratefully downing the glass of water that Ellen gave him before letting out a whoosh of breath.

“You’re one of us, brother.” Benny chuckled deep, gripping his shoulder. Dean couldn’t help but think about how mismatched this little gang was. There was mama bear Ellen, who doted on everyone as well as being a badass in her own right, mother of the sweetly fierce Jo, or Joanna Beth, who could flash a sweet smile at one point but stare daggers the next that can chill bones. Benny, with his distinct cap and fashion sense, paired with the slow drawl of an accent and rough-around-the-edges demeanour.

And then there was you. By what he knew of you, you were a firecracker. Cheeky smiles and a confident way of moving about pairing beautifully with your suave way of handling and mixing drinks. Paired amazingly, like a gin and tonic, or vodka and soda. Beginner’s drinks, but a classic and something he’d walk back to every time. Or maybe you were like whiskey on the tongue. You had an almost irresistible burn to you. Maybe a bourbon, with the hint of sweetness to your demeanour.

Ah, he’d find out someday.

You woke up the next morning, in the bed that was in your room at the Roadhouse to a texts from the group chat you all had, which didn’t include Ellen otherwise she’d chastise you all for the messages you left on there sometimes. You knew that today would be rather an eventful day, since Bela, Meg and Ruby were coming to work on your shift. The trio were alike in every sense of the word, but there was a respective increase in the level of savagery. Bela was smoothly rude, in either a way you couldn’t fault her for or one that you just couldn’t argue back to. Meg could roast you without a second thought but she made it sound like charisma, which it was, rather than outright hatred. If she wanted to, however, she could let you know she hated you. Ruby was just downright honest. Brutally honest in every way possible, but she couldn’t help but be one of your best friends. For all her sharp insults and snarky comments, she just had a wow factor you couldn’t ignore.

Since Dean was in need of a place to stay, Benny graciously offered to let the newcomer stay over. You and Benny had found the Roadhouse together, and you knew a lost soul when you saw one. A kindred spirit. You’d lived at the Roadhouse, courtesy of Ellen and Jo, and even when it wasn’t your shift, you always managed to make it there for a good day of relaxing, laughing and playing pool and maybe poker. Today, since it was a Sunday, the Roadhouse closed early, which meant you all could play random games and jam to karaoke and old songs on the jukebox.

You checked the messages on your phone, snickering at how many there were. But what caught you off guard was the latest one.

Queen B: Alright, what’s the deal with the new guy? Is he hot?

You: Bela, chill. Don’t go hitting on Dean already.

Megolodon: Dean? Even his name sounds sexy as hell

Ruby-gina George: Y’all are desperate

You: Right? Jesus, you haven’t even met the guy yet

Queen B: I call dibs on him 😉 Megolodon: I hope he has a brother, if you know what I mean 😏 older or younger I don’t mind at all, but I prefer younger

Ruby-Gina George: We haven’t even seen him yet

You: Stop thirsting over a guy you haven’t met

Queen B: You’ve seen him- is he hot?

Megolodon: C’mon, spill

Queen B: IS. HE. HOT

You: You two need to STOP

Ruby-Gina George: Touch freakin’ grass

Ben Dover: Leave the poor girl alone, Bela, she needs a breather

You: FINE. He’s attractive, alright

Queen B: HE’S MINE

Megolodon: Dibs on his brother

ScarJo: My god, stop blowing up my phone or mom will see these messages and fire us all

Queen B: Worth it

Megolodon: Yeah, I’m cool with that, just give me the hot bartender’s brother, please and thank you

Casanova: Who are we talking about? I’m confused.

Ben Dover: New hire

Casanova: Ah.

You shook your head, shoving your phone in your pocket as you stood up, heading over to the cupboard. You pulled out a red plaid shirt, taking off your tank and pulling the chosen clothing item on, doing up the buttons before heading to your mirror and trying to tame your hair for the first time in ages. Eventually, you settled on a simple rope braid that still had a few strands coming out of it, taking off your sweatpants and replacing them for jeans. Rolling up your sleeves to your elbows as you went, you zoned out while staring at the silver band on your finger with a snake engraving.

The delicate welts in the ring.

You weren’t married, no, but it was a part of where you came from. You weren’t proud of your history. The one part of it that came out good was your siblingship with Benny.

You met the sunshine streaming through the window, along with the sight of Dean already working at the bar. His flannel’s sleeves were rolled up to his elbows, his hair was short and spiky and he wore a soft smile on his face that suited him. However, his eyes flickered to a girl at the bar you knew all too well. What with her penchant for the finer things in life, hence the perfectly styled brown hair and clever green eyes, complete with a British accent.

Bela Talbot.

She was giving Dean what looked like bedroom eyes until his eyes flickered over to you, his face lighting up instantly with a chuckle at whatever she was saying. You seemed to pick up your sleepy mood as well, returning the grin. Bela smirked slightly, pumping her eyebrows twice as she took a sip of her wine. Wine in the morning. It made you grin at your friend.

How very Bela.

“Mornin’, sweetheart.” Dean rumbled, his morning voice sounding deep and rich. “Sleep well?”

“Slept great, thanks.” You replied softly, pouring yourself a glass of water and sipping it. “You settle in ok? At Benny’s?”

He nodded. “Oh, yeah.” He chuckled a bit, looking down with a bashful smile and a bite of his lip. “He’s great. And it’s great at his place.”

“Had I come earlier, I would offer you a bed at my place.” Bela smirked, then winked playfully rather than flirtatiously. “There’s only one, but I wouldn’t mind sharing.” The comment got a laugh out of both Dean and you, knowing it was all in good fun.

“An offer that I probably wouldn’t refuse.” Dean replied with a suave tone that had Bela grinning at you, nudging you before pointing at Dean with a manicured finger.

“I like him. He’s funny.”

“Good to know.”

“Well, you’re quite a handsome one.” Meg swayed up to the counter, dark brown hair swaying as her equally as dark eyes scanned Dean. She delicately put out her hand for him to shake. “Hi. Meg Masters, darling.”

“Dean Winchester.” Dean shook her hand with a sideways look, seeming rather flattered by the attention of so many women. “And thank you.”

“Just for research purposes-”

“Meg, don’t say it.” You whispered, but she waved you off with a sultry chuckle, her eyes focusing on Dean as she stole a bottle of vodka from behind the bar, pouring a shot which she threw back expertly.

“Do you have a brother? Out of curiosity.” She asked blatantly, smiling innocently at Dean, but you knew the smile wasn’t so incredibly innocent. Meg was like a demon; she corrupts easily. But she was a loveable little devil.

“Oh, shut up, we don’t have to be so touchy feely and up close.” Ruby groaned as she walked in, blonde hair swinging. “And get me a shot of tequila, it was a long and insufferable car ride.”

“You must be Ruby.” Dean noted, pointing at Ruby and smirking slightly. “Bela’s given me the rundown on who’s who. And yeah, I do have a younger brother. Sammy. He’s a dork.”

“Even better.” Meg winked as she poured Ruby a shot of tequila and passing it to her. “Where’s Benny at? I need my daily dose of that accent otherwise I might go insane.”

“You’ve already got the image of the newbie’s little brother so far up your ass, I’m surprised you remembered Benny.” Ruby snorted, taking her shot. “He’s out bein’ errand boy with Ellen and Jo. Texted him when I got here.”

“Earning some brownie points, are we?” Bela giggled. “How very like our suave gentleman.”

“Wine before breakfast.” You quipped, sipping your water. “How very like our expensive Brit, hm?” A round of laughter came from everyone around you, including Bela.

“You got me there.” She sighed playfully, sipping her wine. “Damn you.”

“Damn me.” You winked back, and then a nervous chuckle came from Dean.

“Don’t mean to be a downer on the party, ladies, but I’m feelin’ kind of out of place here.” He gave you all a nervous smile, and the lost puppy look was starting to come out again. You laid a comforting hand on his forearm, tilting your head.

“Don’t worry about it.” You smiled softly, letting out a breath through your nose. “We all love you already. Even if these three are too much.”

“Too much looks good on me, biatches.” Ruby added with a drawl, which got a grin out of Dean and you.

“We get it, Ruby.” You giggled, then glanced back at up Dean and his gorgeous green eyes. “You’re doing great, Dean. Don’t sweat it too much.” The comment got a suggestive ‘ooh’ out of the other three girls in the room, which had you and Dean looking to the counter and the floor respectively with dumb grins on your faces.

“BREAKFAST!” Startled all of you when Ellen walked in with Benny and Jo, the women holding two grocery bags while Benny carried four, most likely out of pure gentlemanliness.

You shared a soft look with Dean, followed by a reassuring pat on his forearm before you stood up and moved to help Benny with the bags. He glanced down at his forearm with a slight smile, fighting off a blush as his tongue darted out to lick his lips. His hand rubbed over the spot before he got to unpacking the grocery bags, feeling assured. Feeling safe.

Feeling like he was part of a family.

bDe: so this is the group chat, huh

You: Hey, Dean 👋

bDe: hey, sweetheart ;)

Ruby-gina George: Where did SWEETHEART come from

Queen B: You wish you were someone’s sweetheart, Rubes

Ruby-gina George: In your dreams, Bell-bottoms

Queen B: But you hate bell bottoms

Ruby-gina George: Exactly 😊

bDe: are they always like this

Ben Dover: You get used to it, brother

You: It’s all uphill from here

Casanova: Can someone please tell me the name of the new hire? I need to add him to my contacts.

bDe: dean winchester

Casanova: Thank you. I am Castiel Novak.

ScarJo: Cas, the perfect spelling, punctuation and grammar is NOT necessary

You: Yeah, how can you type that without getting bored

Casanova: How do you type without perfect spelling, punctuation and grammar?

Megolodon: We just type, Cassie baby, it’s not that hard

Queen B: Even I don’t type that fancy, and I’m British

Ruby-gina George: Part fancy Brit, part asshole

Queen B: I hate you

Ruby-gina George: You’re such a flirt

You: Like I said, Dean, uphill from here

ScarJo: Yeah, doesn’t get much worse than this

bDe: nah this right here is gold

Ben Dover: *eats popcorn*

bDe: can I have some

Ben Dover: sure, brother

You: All of you are unhinged- @Casanova are you gonna be there on your shift tomorrow

Casanova: Yes, I am.

Queen B: Our dear Cas, bland texter by day, expert mojito mixer at night

ScarJo: Sounds accurate to me

Casanova: I hate you all.

You : You love us ☺️

Casanova: I suppose that’s true.

After closing, everyone had gone to their respective houses, or so you thought. You were about to change and get into bed after a long day of supervising the bar in case Dean needed help or the girls were being far too flirty for their own good, but then you heard clinking glass from downstairs that piqued your interest. You prepared to grab the baseball bat from the cupboard on the landing as you crept out, but only heard the humming of a low voice you recognised as Dean. You walked into the main bar to find him cleaning the glasses, the clink coming from when he set them down with the others. But he heard you enter, and he looked up with the washcloth still held in his large hand. “Hey, sweetheart.”

“Dean, what are you…” You quickly moved to his side, ducking under the counter and taking the cloth. “Why are you here so late?”

“Thought I should clear up. It makes a good first impression.” He shrugged, and you got the whiff of ‘I’m lost and just want to fit in’ again. Dean mentioned a brother yesterday, so it had you wondering why he found the Roadhouse in the first place. Everyone was a lost soul who came here to work. Castiel divorced his wife and left his daughter, and needed a job after he was fired. Ruby left her abusive family, and Meg was in a toxic relationship. Bela had been on the run from her family and had become a pocket thief in the process until Ellen gave her a place at the Roadhouse. As for you and Benny, well, that was a topic neither of you were fans of touching that topic.

“You don’t have to work for that, Dean.” You reassured, squeezing his shoulder. “You’re already fitting in. Just don’t change yourself for insecurity’s sake. It’s gonna bite you in the ass later.”

“Good to know.” Dean chuckled, fiddling with the ring on his finger. “And I prefer my ass to be unbitten.”

“Don’t we all.” You joked, then gave him a smile. “C’mon, if you really wanna make a good impression, then get some rest.”

“You sure?” He frowned a little, his hand twitching to take the cloth from your hands, but you moved it further away. “I could help out, y’know.”

“Not that we don’t want you here, it’s just that we value physical well-being. And mental.”

“Gotcha.” He laughed, nodding as he picked his jacket off the coat hook. “Are you absolutely sure?” Dean wore a concerned look on his face, not wanting to leave you alone to do work. “I could save you some time.”

“I’m gonna drag Bela, Meg and Ruby’s asses to do this.” You chuckled, setting the cloth down on the counter. Dean felt comfortable as hell around you. Maybe it was because you were the first one he knew at the Roadhouse. “Go on, get.”

“Alright, alright, Jesus.” He took out his keys, winking smoothly. “Have a nice night, darlin’.”

“You too, Dean.” You waved as he left, a minute later the loud purr of a car, crunching gravel and screeching tyres gracing your ears.

3:00AM

Queen B: Anyone awake, I’m boredddddd

Megolodon: Same girlie

Ruby-gina George: Some people value their sanity you know

Ben Dover: Why are you up at 3am

bDe: so much for being told to get some sleep

You: You two are insufferable

Casanova: We have work tomorrow.

Queen B: Ohh god, I’m so drunnnnkkkkk

ScarJo: How much hard liquor have you had?

Queen B: Mmmmmmmaybe three

Queen B: b9ttles of tequ8la You: Three WHAT

Ruby-gina George: She’s so slammed she’s typing numbers

Megolodon: Awesome

Ben Dover: Bela, darling, where are you

Queen B: in your lap

bDe: damn

NEXT UP:

“So, darlin’, what do you do in your free time?” Dean asked you, cleaning out a glass with a rag and shooting a wink to a couple of giggling girls nearby. You poured a whiskey for a patron, sliding it across the table.

“Well, I’m a big fan of joyrides.” You answered with a goofy grin. “My Mustang’s always fun to take a spin in.” The mention of your Mustang got Dean’s eyebrows up to his hairline as he pointed out of the window.

“That beaut’s yours?” He exclaimed in disbelief, laughing. “Damn. That’s a serious muscle car.”

“Yeah, my Valkyrie. Val’s my sweetheart, always will be.” You looked up wistfully at the mention of your beloved car. “And your Chevy Impala, she’s absolutely gorgeous. I could listen to her purr all day.”

“That’s my Baby.” He bore the same wistful look you did, then nudged you. “We should take ‘em out for spins. Y’know, joyrides.”

“You sure?” You chuckled, looking up at him. “I don’t drive easy.”

“Even better.” He gave you a little wink paired with a click of his tongue. He flipped a bottle in his hand, pouring a whiskey shot expertly and handing it to you. “Ma’am.”

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