Behind Bars….Again
Series Masterlist
Summary: Ever since Sam went to college, Dean has been having a hard time. Drinking, gambling, driving recklessly, the works. If it weren't for Y/N covering his ass everytime and bailing him out everytime, he would've been tossed in jail by now. Or worse yet, John and F/N would've dealt with it.
Y/N is 19, Dean is 23, Sam is 19 years old but is away at college)
BASED ON:
The Old Testament Series.
Genesis Primis: A Supernatural Rewrite (Dean Winchester x Reader) by @dianawinchester03
(Ps. I imagine Xander as Drew Van Acker. He played Jason DiLaurentis in Pretty Little Liars)
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Lake Preston, South Dakota
•November 2002:
Dean had been arrested and he called the only person he knew he could count on to get him out. After practically demanding his phone call from the officers who were all too familiar with him, he was whispering into the phone pleadingly,
"Y/N, you don't understand, you have to get me out of here!" he whispers into the phone as a police officer looks on suspiciously. Dean just smiles innocently and waits for her answer.
"Fine but you owe me something!" She answers annoyed.
"I swear, I'm gonna kill this asshat one day" Y/N grumbles to herself as she slides on her fuzzy pink bunny slippers and her robe, not bothering to change from her pajamas because right now that was the least of her worries. Sam had run off to college a little over a year ago, meanwhile Dean was taking it especially hard.
She misses her best friend too but Dean has been getting into trouble a lot lately. And it's beginning to worry her.
-
Dean waits patiently in the police station's holding cell, fiddling with a paperclip he somehow managed to find. Every now and then a police officer walks by, eyeing him suspiciously before continuing on their way.
As Dean hears footsteps approaching, he perks up, hoping it's y/n.
-
Y/N creeped down the stairs to see her dad passed out on the couch, half-cradling a bottle of Jack in his lap, the tv still on showing late night informercials.
John went on a hunt alone and F/N stayed back for god knows what reason, she had a feeling it was to keep an eye on her. Which irritated her even more, his breathing down her neck is starting to get to her and she's sick and tired.
You'd think, for someone who was willing to send his 14 year old daughter out on her first hunt with the Winchester boys, he wouldn't be such a pain in the ass. A couple of teenagers taking down a Wendigo on their own? The man is beyond a hypocrite.
Since her dad got plastered the night before, she knew he wouldn't be up until the next evening. So before she left, she made sure to gently take the bottle out of his hands, making sure not to wake him up. Before laying him on his side, she then unfolded the blanket on the single couch and threw it over him.
"Sweet dreams, daddy. Love you" She whispered before laying a gentle kiss on her fathers forehead. He stirred a bit but remained asleep. As much as he fucking annoys her, she loves her old man.
Y/N grabbed her wallet from the kitchen table before lightly creeping out of the kitchen and out the back door. Thankfully, Dean left his Baby at the house before he went out drinking since John gave it to him.
When he went on the hunt, he borrowed her fathers truck. She didn't want to take Quinn in risk of waking f/n up.
-
The Impala drives through town, passing various shops and buildings before coming to a stop in front of the police station. She made sure to pass and pick up a burger, fries and milkshake for Dean, knowing that he was probably starving. The greasy diner food sat in the backseat along with the takeaway-milkshake in the cup holder.
She finally made it to the station, pulling into the lot before putting the car in park.
Y/N pushes open the police station doors and walked inside, her fuzzy bunny slippers making a slight shuffling noise against the linoleum floor. She made her way to the receptionist, flashing her a sweet smile. "Hi, I'm here to bail out a Winchester. Dean Winchester."
The receptionist glances up at her, raising an eyebrow at the fuzzy bunny slippers y/n sported before checking her computer screen. After a moment, she looks back up at her"
"Ah, Mr. Winchester. He's in holding cell three," she says, gesturing towards an aisle of cells behind her. Her eyes landed on Dean who was playing with a paper clip. Deans drunken smile brightened upon seeing her by the receptionist's desk, flashing y/n a cheeky grin and lifts a hand in a wave hello.
"Great, how much for the bail?" She asked, beginning to dig into her purse but her jaw dropped at the response. The receptionist glances at the information on her screen again before replying, "The bail is set at $500." Y/N glares over at Dean before looking back at the receptionist.
She didn't have that kind of cash in her, and she didn't think to take her father's fraud credit card.
Stupid, stupid, stupid.
"Did he kill someone?! 5 hundred bucks???" She exclaims at the preposterous amount. The receptionist shakes her head, a hint of annoyance in her voice. "No, no. It's a bail for public disturbance. Your friend caused quite the scene. And it's not his first time in here."
Dean just shrugs innocently from his cell, feigning innocence. "Hey, it's not my fault they can't handle a little fun." Y/N's rage filled eyes snap over to him, a firm finger pointed in his direction.
"You shut your mouth, Winchester. I'll deal with you later" She grits her teeth at him. Dean holds up his hands in mock surrender. "Alright, alright. Can't I have a little bit of fun every now and then?" he grins, clearly enjoying riling her up.
The receptionist watches the exchange with some amusement, raising an eyebrow at her interaction with Dean. Y/N flipped him off, mouthing 'You're dead meat' before turning back to the receptionist with a tight smile. "That still doesn't amount over the fact that it's $500." She crossed her arms over tank-top clap chest before politely asking,
"Can I speak to the arresting officer??" The receptionist nodded, "That would be Officer Thompson" She stated before picking up the phone and dials a number, her eyes drifting to Y/N's bunny slippers again. The name rang a bell in her head. After a moment, she speaks into the phone, explaining that she wanted to talk to the officer who arrested Dean.
"Thompson?" Y/N asks, the receptionist nodded in confirmation before she internally groaned, the one Thompson she knew was Alexander Thompson. Her ex boyfriend from high school when they went to Sioux Falls High in the late 90s before Bobby's falling out with their dads.
They dated for no more than 6 months before parting ways. They surprisingly ended on good terms, however. Both deciding that they wouldn't be able to make it work due to y/n lying and telling him she wanted to go to California to study and Xander wanted to stay in Sioux Falls to join the force right out of high-school.
She assumed he transferred to the Preston Lake department, if it were him.
The truth was the nature of the family business, it pained her to leave but she had to tough it out. In her mind, it's her fault for getting attached to someone. Knowing they they weren't gonna stay there for long.
It also got to her because he was the first person she ever felt a connection with, her first real relationship. They lost their virginities to one another, that's connection no one could come between.
To his knowledge, she's probably back 'home' for Christmas break but that's the furtherest thing from the truth.
"You can go see him in the bullpen, desk 19" The receptionist told her, y/n muttered a low "Thanks", before shuffling her bunny coated feet over to the bullpen. There he was, sat filling out paper work.
Officer Thompson looks up from his paperwork and spots Y/N approaching, a surprised expression on his face. "Hey, y/n/n," he says, setting down his pen. "How can I help you? You wanted to speak with me?" he asks, eyeing her curiously.
Dean, watching from his cell, grumbles something under his breath as he sees Thompson.
"Hey, Xander. I don't mean to yell but $500?!"
Alexander Thompson smiled softly, his heart swelling when she called him "Xander," an old nickname she gave him when they were dating. He sighs and runs a hand through his hair.
"Listen, I had to set the bail high. Your friend here was making a scene and causing a disturbance. Got into a bar fight, broke a bottle over a man's head. He's gonna need stitches but he'll live. Plus, he resisted arrest," he explains, gesturing to Dean in the cell behind them near the receptionist desk.
"Come on man, you know how he is. And you know I can't afford $500" Y/N says exasperatedly. Thompson rubs his neck, looking slightly uncomfortable. "I know, I know, but protocol is protocol. And your friend hasn't exactly been cooperative."
He glances over at Dean, who is now whistling and twirling the paperclip he was playing with earlier. Y/N's eyes flickered back over to Dean. She groaned at the man child infront of her. "Please, I've never asked you for anything Xander" She pleaded with him.
Thompson sighs heavily, his resolve weakening at the look on Y/N's face.
"You're right, you know how to get to me," he mutters, shaking his head. "But this is a one time thing, got it? I can't let him off easy next time he gets arrested."
"I'm asking you as a friend, and nothing more." She stated him. Thompson rubs his face, considering y/n's plea. He looks over at Dean, who grins widely at her knowingly.
"Fine," he says finally. "I'll lower the bail to $50. But this is a one time deal, understood? And if he gets arrested again, I won't be so lenient." Thompson agrees, but firmly states as he got up from his chair.
"Thank you!" Y/N exclaimed in relief, thanking him gratefully before giving him a hug. "I promise, he won't" She assures him. Thompson is surprised by the hug, initially stiffening before graciously returning it.
He melted into her touch, "Yeah, yeah," he mutters, a faint blush on his cheeks. "Just make sure he stays out of trouble."
Dean watches the scene from his cell, rolling his eyes.
"I'll see you around" She said sweetly before walking over to the receptionist and handing her the money.
Thompson watches Y/N walked away, a mix of disappointment and lingering affections on his face.
The receptionist takes the money and starts processing the paperwork to release Dean. After a few minutes, she calls out, "You can release Mr. Winchester now."
A police officer unlocks the cell and Dean steps out, a smug grin on his face. "Thanks for bailing me out, princess," he teases.
She narrows her eyes at him before snatching him by his ear and dragging him out of the station. Dean protests loudly as she dragged him by the ear out of the police station, a few officers watching the scene with amused grins.
"Ow, ow, ow, ow, ow!" he hisses, trying to pry her hand off his ear. "Dammit, ease up on the grip!" She pinched harder before letting go. "You dumbass!" She exclaimed in frustration before smacking his chest.
Dean winces as she pinched his ear even harder before finally letting go. He rubs his chest where y/n slapped him, a pout on his face.
"Alright, alright, I get it! I messed up, alright?" He glances at her fuzzy bunny slippers and grins. "And what's with the slippers? Couldn't leave fuzzy at home" He snorts. "1. Leave fuzzy out of this" She stated firmly, pointing a finger at him while he had a cheeky grin plastered across his face.
"2. Why slap to his chest did slap you slap have slap to slap go slap and slap get slap arrested! slap slap slap" She smacked him with each syllable, he didn't dare protest before he knew this time, he was wrong.
"What the hell is the matter with you, charming?! This is the 4th time! If John and dad knew, they'd have our fucking heads!" Y/N exclaims lowly with a warning tone.
Dean winces with each slap, trying to shield himself with his arms.
"Hey, hey, hey! Stop slapping me!" he protested, trying to keep a straight face. "I didn't mean to get arrested, okay? It just sort of happened..."
He glances at y/n again, taking in her grumpy expression and the fuzzy slippers. "And seriously, the slippers? Don't you have some real shoes?" He raised an eyebrow.
"Dean!"
Dean holds up his hands in surrender, trying to avoid another slap.
"Okay, okay! I'm sorry, I shouldn't have gotten arrested. But seriously, the slippers? They make you look like a bunny."
This earn him another smack but this time across the head.
Dean winces again, rubbing his head where she slapped him. "Ow! Hey, quit hitting me, princess!" he protested, a hint of amusement in his eyes.
He glanced at the fuzzy slippers again, a smirk spreading across his face. "But seriously, those things are ridiculous. You look like a character from a children's cartoon."
"Jesus..." Y/N huffed, rubbing her temples. "Just get in the car" She grumbled. "Fine, fine" he says, a hint of resignation in his tone. "But can you seriously stop hitting me now?"
"Shut up before I hit you again" She quipped up before jumping into the drivers seat of the Impala and starting the ignition. Dean still stood where he was. An amused grin on his face, his hands buried in his pockets.
She was worried about him, she cared deeply. So deeply that she tucked her tail between her legs and pleaded with her ex boyfriend to lower to bail so he didn't have to spend the night in jail and have their dads find out. He appreciated it. He admittingly felt a little jealous when she hugged Xander but he shoved it to the back of his mind.
The honk of the Impala's horn snapped Dean out of his daydream, "GET IN BEFORE I RUN YOUR ASS OVER!" Y/N yelled through the drivers side window.
Dean jumps at the sudden shouting, quickly climbing into the passenger seat of the Impala and buckling his seatbelt. "Alright, alright! I'm in! Damn sweetheart, you don't have to threaten me with violence."
"Oh, just like you did that guy in the bar?" She retorted, referring to his reason for getting hauled in cuffs as she put Baby in reverse. Dean rolls his eyes. "That guy had it coming. He was being an ass," he retorts, wincing as he realizes he's about to get reprimanded.
"And I already said I was sorry about getting arrested. Thank you for bailing me out, princess but I didn't mean to cause such a scene." Dean shrugged, thanking her for her kindness. He knew she'd come get it, also expecting to get reprimanded.
"Yeah well you did. I just had a very awkward conversation with my ex, thanks to you." She grumbled, pulling onto the road. Dean raises an eyebrow at her mention of her ex. "Oh, the cop from before? That Thompson guy, right? I remember you guys dated for a while last year." Dean rolled his eyes, a burning feeling appearing in his chest at the thought of Y/N and Alexander.
"Before you start to mock me, no we're not getting back together" Y/N chimed, knowing how Dean was around her boyfriends. He'd either mock and tease her about them or blatantly dislike them. In this case, it was both when it came to Xander.
Dean smirks at her statement. "Oh really? Then why was he giving you that sad, lovesick puppy look when I walked out? Seemed like there was still something there." He teased, masking the burning feeling with a smirk.
"Shut up" Y/N rolled her eyes, pulling into the freeway, just a couple miles from the house. Dean chuckles, enjoying teasing her. "Oh, come on. You can't fool me. I know a lovesick loser when I see one. And that Thompson guy fit the bill perfectly."
"Speaking from experience?" She retorted back with a smirk. Dean's smirk faltered slightly at her remark. "Hey, hey, hey. That's not fair," he protested, a hint of defensiveness in his tone. "I'm not lovesick. I just enjoy the ladies, that's all. No strings attached." Dean defended with a shrug.
"Mhhhmmm" Y/N rolled her eyes, keeping it trained on the road as they drove back to the house. Dean leaned back in the passenger seat, his arms crossed over his chest.
"What's that supposed to mean?" he asked sarcastically, noticing the doubt in her expression. But it was anything but doubt, "You don't believe me?"
"No, I do" She stated before grimacing in disgust, "I just don't wanna imagine it" Y/N gagged, shaking her head. A similar burning feeling appearing in her chest at the thought of Dean with someone else.
"What? Don't wanna hear about my conquests with many ladies?" Dean teased, a wicked smirk painted in his lips at Y/N's clearly disgusted face.
"I will crash this car. Do not test me." She puts her finger up warningly. Dean holds his hands up in surrender, a chuckling. "Alright, alright. Don't bring Baby into this. I'll lay off. No more talk about my conquests. Sorry for ruffling your feathers."
"Good" She huffed, both hands on the wheel as swerved into the left lane, before bending the corner to the dirt road the house was two miles in.
She then remember the food she had for him, "Oh, here I almost forgot" She reached to the backseat, picking up the brown bag with food with her left hand. She handed it to him and when Deans eyes landed on the greased bag, his heart softened. "You- you got me food?"A smile tugged at his lips, "Yeah, I thought you'd be hungry" She shrugged before pointing a finger at him.
"That doesn't mean your off the hook. Now eat. There's a milkshake there for you" She pointed to the cup holder, occupied with her milkshake and his.
Lord, thank you. Dean thinks to himself.
His heart swelled in his chest as he dug into the bag, taking out the burger and unwrapping it. He instantly dove it, but not before offering y/n a bite, which she declined since she had eaten before bed. "You want some fries then?" He asked her with a mouthful of food, "Yeah, sure" She nodded, he then took out one of the fries from the bag and put it out to feed her.
She snorted at the gesture but accepted it graciously with her mouth, she chewed on the salty chip contently as Dean dove back into his burger.
Dean grins drunkenly at this, happy she didn't just snatch it out of his hand and fed herself finding her grumpy demeanor from earlier amusing. "You know, you're cute when you're mad" he teases, reaching over to poke Y/N's cheek lightly.
"Yeah, and you're an idiot when you're drunk, charming" She snorted, gently smacking away his finger that was pressed into her cheek.
Dean feigns hurt, holding his hand to his chest dramatically as he let out an exaggerated gasp.
Y/N rolled her eyes at this, trying to bite back her smile.
"Hey, now you're just insulting me," he protests with a mouthful of food, unable to keep the grin off his face. "I'm not always an idiot when drunk. Just most of the time."
He gives Y/N a cheeky smile before glancing out the window at the passing scenery.
She couldn't help but chuckle at this, "That you are, charming. That you are" She laughed as she pulled up in-front of the house. Putting the car in park, Dean had finally finished his burger and milkshake, tossing the discarded contents in the paper bag.
"Before we go in, I need to talk to you" She stated seriously, turning to him in the drivers seat.
Dean frowns slightly, sensing the seriousness in her tone. "Okay. What's up?" he asks, turning to face Y/N in the passenger seat.
She took a deep breath before beginning. "I know since Sam left for college it's been bugging you. And I get it, I do. I miss him like crazy, but you're getting yourself into trouble. You need to be careful because if our dads find out, we could get in a lot of trouble and that's worse than having the police in our ass" She lectures.
Understanding how much it bothered Dean now that Sam was away at college but also in a warning way that it would not end nicely if John and F/N found out.
Dean grits his teeth, clearly not thrilled about being lectured.
"I can handle myself, princess," he retorts, his defensiveness kicking in. "I don't need you to tell me how to deal with my feelings. I'm a grown ass man, not a child."
He crosses his arms over his chest, looking out the window broodingly.
"Charming..." She sighs exasperated. "I'm not trying to tell you how to deal with your feelings. I'm your friend and I'm gonna be honest, you're saying you're a grown ass man. That you are but you're crossing your arms at me and acting like a child" She points out with brutal honesty.
Dean scowls at her comment but deep down, he knows Y/N's right. He was clearly annoyed at being called out on his behavior. He was acting childish, but he wasn't going to admit that.
"I'm not acting like a child," he protests, even though his body language says otherwise. "I'm just... frustrated, okay? I miss Sam too, and it sucks that he's off at college having a blast while we're stuck here with our dads always on our asses." He grumbles in frustration, shaking his head.
"I get it, sweetie. I do" She says gently, using her pointer finger and thumb to turn his face by his chin to her. "But I'm always here if you wanna talk. It's better to do that then get arrested and in trouble"
Dean huffs, grudgingly meeting her gaze deep down, her words hit a nerve. He knows shes right, but he can't bring himself to admit it. He's too damn stubborn.
"I don't need to talk," he mutters gruffly. "I can handle my own problems. I don't need your help."
Her face hardened, he was being stubborn as always. She didn't want to just give up because he never gave up on her, he always had her back and she always had his along with Sam's. But the man was arrogant, he needed some tough love. And that's what he's gonna get.
"Alright, then how bout. Next time you call me in jail, I'll leave you to rot for the night and let John pick you up.....That is, if he does" She spat angrily, leaving the keys in the ignition before jumping out of the car. Feet padding heavily towards the porch.
She tightened her grip on her robe from the chilly air.
Dean's eyes widened at her words, a mix of anger, disappointment, and disbelief flashing across his face. He was not expecting that reaction. He was used to her usually coddling him and being understanding. But this time it was different.
"Wait, wait, wait!" He called out, scrambling out of the car to follow her. "Hey, come on, princess. You don't mean that!"
She turned to him, arms crossed over her chest. "No, I do. Because that's what you wanted right? Me to leave you alone, here you go!" She grumbled back lowly, fishing her house keys out of her pocket.
Dean's heart sank a bit at her response, realizing he had gone too far this time. He hated it when she was mad at him, especially when he was the one who caused it.
"No, that's not what I meant," he protested, running a hand through his hair in frustration. "I just... I just don't want to be lectured at, okay? I can handle myself. I'm not some kid you need to look out for."
"I'm your friend, Dean. I'm care about you. We've always had each others backs, what's the issue now?" She says exasperated, a bit hurt but she swallowed it down.
Dean hesitates for a moment, swallowing the lump in his throat. He didn't want to admit it, but she was right. They had always had each others' backs, no matter what.
"I... I don't know," he mutters, looking down at his shoes. "I guess I just feel lost without Sam here. I miss him, and I've been taking it out on you. I'm sorry, princess." He finally admitted, her heart softened.
"I'll try and do better, I promise" He sighed, his head dropping with shame. "That's all I wanted to hear, charming." She smiled softly, glad her tough love got the truth out of him.
Reaching over to hug him, Dean lets out a small sigh of relief, a smile tugging at the corners of his mouth. As he returned the hug, "Thanks" he says softly, squeezing her tightly whilst caressing her hair. "Sorry for being such a dick tonight. I didn't mean to take out my frustrations on you." He apologized.
"We're family. It ain't supposed to be perfect" She chuckled, her arms around his midsection. Dean chuckles, his arms wrapping around her shoulders as he pulled her closer. He agrees, resting his chin on top of her head as a fond smile crept onto his face. "Yeah, yeah," he muttered, pulling away from the hug to look at her. "Family."
"Come on, let's go. It's cold out. Dads passed out on the couch plastered. I'll make you a cup of hot cocoa" She whispered as she opened the door, checking to make sure her father was still passed out.
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Authors Note: This one has been sitting in drafts for the longest time. So why the hell not post it, huh? I've mentioned before but the book isn't really gonna be in order much it's gonna have a few time skips Eg, it'll go from them being kids, to adults, to teens, back to kids etc. But I'll fix it up when it's completed and put it in order you will understand.
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Lol, hope everyone liked!🫶
Xoxo
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