#dean wincherfanfic

[jawritter]

When The Lights Go Out

Chapter 4

Summary: Life hasn’t been your best friend lately, you lost your job, and are on the verge of losing your apartment. Who knew when you decided to join a Sugar Daddy app that your best friend suggested ina last ditch effort to save your apartment, and not end up on the street, your first and only client would turn your whole world upside down.

Pairing: Mobster!Dean Winchester x Virgin! Reader

Word Count: 2846

Series Warnings: Mob level violence, injured Dean, description of injury, creepy Godfather John Winchester, John is pretty much a double bag, escort services, virgin reader, lose of virginity and all the insecurities and fun stuff that come with it, age gap (23 year old reader; 40 year old Dean), angst, unrequited/requited love?, language, smut, unprotected smut.

Chapter Warnings: Shy!Reader, angst, John is number one douchebag, talk of escort services, language, I think that’s it y’all.

A/N: Beta’d by @deanwanddamons! Thanks so much love!! Please don’t copy my work!! Feedback is golden! Hope you all enjoy this one!! It’s gonna be a little bit of a slow burn y’all, but just hang in there!

(This fic is based on this request: Could you do a Dean x reader where she is 23 and lives alone in her apartment, she gets fired and can loose her house, her friend tells her about a sugar daddy app, she makes a profile and Dean 40, contacts her, she is virgin and don’t offers sex, Dean is billionaire business man and needs a girl for his business parties,the reader is really shy, blushes a lot, they fall in love, he takes her to a trip and makes love to her on a private island, could it be a series?)

Want more? Check out my masterlist!!

***MASTERLIST***

***SERIES MASTERLIST***

“Relax, you're gonna be just fine.” Dean said soothingly as he stood in the doorway of your small apartment bathroom, watching you fuss over your makeup. 

Giving him your best bitch face in the mirror, you check your hair one more time before turning to him, letting your arms fall to your sides in a huff. 

“Well, I guess it’s gonna have to do, because this is as good as it’s gonna get.” you tell him, fighting the urge to throw up, scream, and run away all in one. 

True to his word, Dean had stayed at your place all night, and even though you hated to admit it, you did feel a little more comfortable around him now that the two of you had spent all of last night, and most of the day, together. 

If you were being honest, you weren’t sure what you were feeling as a whole. It did feel nice to cuddle with Dean last night, and it did help you a lot that he now knew you were a virgin, and didn't fire you from this strange job thing you had between you, or laugh in your face, but he was still a Winchester, and you were still in way over your head. 

If you fucked this dinner up today, you were both fucked, and that wasn’t something to take lightly.

Dean crosses the floor in one, maybe two strides, picking you up as if you weighed nothing at all, and sat you on the sink in your bathroom before slipping between your knees, his large hands on your waist in order to keep you from falling off, and your hands making their way around his neck to stay balanced. 

“I want you to do me something,” Dean said, leaning down and catching your lips in his in a swift peck to get your attention. “Stop worrying so fucking much!”

Leaning your head down on his shoulder, you closed your eyes and attempted to take a deep cleansing breath. You knew you were overthinking this.All you had to do is sit there and look pretty, much like at the party Friday night. 

Dean had gone over the “details” of your relationship over breakfast this morning, and now, at least, you had  a story of how you met. 

Dean had said since you were an accountant at JPMorgan, he would tell the family that he’d met you on one of his basic runs to the bank, and gotten your number.You were a few dates in, and had only been dating close to two months, which would explain the fact that you don’t know each other very well, and cover up the fact that you were still a little awkward around each other in some aspects. 

As far as the lack of job now, Dean said that you picked up a job as an editor for a local publishing company, and worked from home so that you could study graphic design on the computer. Something you always wanted to do. 

Dean also told you that he could help get you on at the publishing company to work from home reviewing different transcripts next week, so that everything would be legit. He also promised to pick up the slack in whatever money you needed, so that you would want for nothing, seeing as he was technically still your client, even though this had taken a turn far surpassing escort services, and client, clientele relationships. That ship sailed the moment that you had to be introduced to John fucking Winchester. 

“I just don’t want to fuck this up.” you tell him, searching his mossy green eyes as he searched yours. 

“Pretty girl, you’re not gonna fuck this up. Everything is gonna be just fine, just follow my lead, nothing bad will happen, and I have already told you, I will pay you very well, you know that. “

Nodding your head, you let Dean give you another peck on the lips before helping you down off of the sink, and lacing his fingers in your own, leading you towards your apartment door, and down to his car that was parked on the street. 

When you came to a stop you couldn’t help but drool over the sleek black ‘67 Impala that was waiting for you both there. Dean gave you a smirk as he opened the door, his features shifting to an almost playful, boyish smirk that seemed to wash away some of the years that he held so close to the surface, yet so out of reach. 

“You like?” he asked, wiggling his eyebrows at you playfully. 

“Dude, she’s beautiful!”

“She’s my Baby,” he said, helping you off the curb and into the car, shutting the door, before jogging around to the  driver’s side. 

Baby purred to life, as Dean turned the key in the ignition, and pulled onto the busy New York street. Reaching over he grabbed your hand in his, giving it a reassuring squeeze. 

‘You can do this Y/N,’ you thought to yourself, ‘just act natural.’

God, you hoped you weren’t lying to yourself, because if you fucked this up, there was no word in any language that would describe just how fucked you were.

-------------------------------

A short drive later, and Dean was turning onto an expansive estate in Upstate New York. Rolling hills with green grass, a long paved driveway, and a large house that looked more like a castle sitting on top of a hill greeted you as Dean pulled up in front of the house, and put Baby in park.

“Okay sweetheart, you ready?” Dean asked, giving you a reassuring smile as he put his hand on the door, ready to open it.  

“As I’ll ever be,” you tell him in what you hoped was a confident tone. Dean smiled at you, giving you a peck on the cheek and whispering in your ear.

“It’s already show time Y/N. People are watching and there are cameras everywhere, but it’s okay, I’ve got you, and I’m not going to let anything happen to you remember that.“

Nodding your head, you lean over and boldly give him a peck on the lips, which caused a grin to spread across his face. His eyes sparkled as he kicked the door open, and made his way around the car to open your door. 

You weren’t even out of the car all the way when Sam came to a stop in front of the two of you with Jessica in tow. 

“Dean, Y/N, It’s good to see you again.” Sam said, greeting you warmingly and Jessica smiled at the two of you. You managed to give Sam a tight, nervous smile as Dean pulled you closer to him. 

“Where is everyone Sammy?” Dean asks, turning Sam’s attention away from you, and to his older brother. 

“Out back in the garden. Dad said he wants to have dinner out there. He’s been in a mood all day, you know how he gets. He’s not happy about that deal that didn’t go over so well this week with you, so get ready for that.” Sam warned, and Dean let out a heavy breath. 

“Yeah, I figured as much.” Dean said, as he and Sammy started making their way towards the garden in the back part of the estate with you and Jessica in tow. Jessica gave you an encouraging smile as you both rounded the corner, and you wondered just how nervous you looked to her. 

You didn’t really have time to  speak to her before the booming voice of John Winchester crossed the lawns, as John, Rufus, and another man in a ball cap came into view. Rufus excused himself, heading towards the other side of the house, as the four of you approached the long table that was already set with plates, beers, and wine. 

“Dean, I was wondering where the hell you got off to when you got home from that job I sent you on, I should have known this pretty little thing would have had something to do with your disappearance.”

You blushed deeply as you hid slightly behind Dean, wishing John would find another target, and just leave you alone.

“Easy old man, you're gonna scare her off, and then I’ll be down to the only girl amongst all you boys.” Jessica chided, as she flopped down at a chair at the table. 

“Jessica, so nice of you to join us this evening.” John said, giving her the side eye before turning his attention back towards Dean, who was helping you sit down in a chair before taking a seat next to you, Sam sitting down next to Jessica.

“So boy. What the hell happened?” John asked, jumping right to business as waiters appeared out of nowhere and started plating food for everyone at the table. 

“He didn’t like your terms, so I executed the order you gave me before I left.”

“You could have at least tried to change his mind.” John said, taking a bite of his food, eyeing Dean like a wolf that was eyeing his pry. You hated the way he looked at Dean. Sure you didn’t know much about their business, but you certainly didn’t feel Dean deserved the way John treated him.

“That’s not really a conversation for dinner Dad,” Sam said, stepping in for his brother, “Dean’s the best we got. If he said the deal didn’t fly, it didn’t fly, it’s that simple.”

John gave Sam an irritated look, but didn’t press the issue.

“Oh, Y/N, where are our manners, so wrapped up with business and all that I almost forgot to introduce you to our guest! This is my friend Bobby. He’s going to be opening up a garage in the area, so he’s here scouting property, and Bobby, this is Y/N, Dean’s new girlfriend."

Bobby gave you a smile and a nod, but said nothing, letting the conversation fall away a little as everyone tucked into their food. What conversation did flow was a lot lighter. Sport, cars, family members that John hadn’t seen in a while.If you didn’t know better, they almost felt like a normal family. Almost. 

One thing you had to say for sure was that you did very much like Jessica.She bit no bones with the large, dangerous men at the table around her, and had no problem putting each and every one of them in their place if they needed it. Especially John. She was like Sam’s personal pitbull, and you made a mental note to make sure that you stayed on her good side. 

Soon enough the dinner was over, and Bobby had excused himself, saying he needed to get back to work, leaving only you and Jessica with the Winchesters. John wiped his face, and threw his napkin down on his empty plate in front of him, his eyes dancing across the table at Dean and you, a smirk that would make the devil blush on his face, as his dark gaze stuck on Dean. 

“Sammy, why don’t you take Jessica in the house and do something to entertain yourselves, I want to have a word with your brother and Y/N in private.” John said, and you saw Dean and Sam exchange a confused look as Sam and Jessica got up from the table, making their way towards the house. Dean shifted closer to you, lacing his fingers through yours to stop your hands from shaking. 

Whatever John had in mind to discuss with the two of you, you had a feeling that this was going to be uncomfortable at best, and humiliating at worst. 

When Sam and Jessica were no longer outside, John turned his full attention to the two of you. 

“So, Y/N. How long have you been seeing my son?”

Swallowing hard, you try to speak past the lump in your throat, your voice coming out a lot smaller than you would have liked it to.

“About two months.”

John nodded, biting his lip and running his hand over his beard. 

“Two months, hmm. So I assume you know by now the line of work our family does.” 

Dean made to say something, but the distinct sound of a gun cocking behind you made you both stop dead in your tracks. Your shaking became visible, but Dean stayed calm, giving you a reassuring squeeze. 

“She knows in theory, but she doesn’t know any details.” Dean said, completely unbothered by the gun that was pointing at his back.

“Let the girl speak for herself Dean.” John said, leering at his son from across the table.

“I don’t know a lot sir, nor do I want to.” 

John nodded his head, chuckling to himself before reaching in his pocket and pulling out his phone, throwing it down on the table in front of you. The picture of Your Sugar Daddy app on full display. Your eyes went wide, and your mouth went dry. Even Dean sat up a little straighter next to you.

“You two want to cut the bullshit and explain this, because you know I don’t like to be lied to Dean.” He said, his voice dripping with venom. “Did you bring a fucking whore into my house Dean? To my dinner table?”

“No.” Dean said, eyes locked on his father.

“Then what the fuck is she doing on the site son?”

“It’s not like that.” Dean said, shifting in his chair.

“Really, because there are DM’s on this account asking her to escort you to your brother’s party last Friday night. Did you think I wouldn’t do a background check boy?”

Suddenly your brain that had turned to a mush of fear started working, an idea hitting you like a lightning bolt. 

“Roll play,” you blurted out, and both men looked at you with shocked expressions, before Dean’s became slightly amused. 

“That’s right father, it’s just, roll play, nothing more.” Dean said, licking his lips sensually, throwing his arm around you, and running his teeth over your ear, sending a visible shiver down your spine that landed somewhere deep in your belly.

The shock faded from John’s face, and pure amusement took its place as he clapped his hands together, throwing his head back in a laugh as the man with a gun behind Dean disappeared. 

“I’m sorry you two. For a moment I thought you were actually an escort.” John said, still chuckling to himself.

Dean gave a tight laugh, and you blushed deeper than you ever have in your life.

“Well father, my sex life isn’t something I like to brag about, I like to keep what happens in the bedroom between the two of us.”

John nodded, still looking very amused, but you thank any God that was listening that he bought it. 

“Speaking of your bedroom, that’s something else I want to talk to you about.” John said, and Dean sat back seriously in his chair.

“In order to keep your girlfriend safe, and keep the high table off of your ass, I want your girlfriend to move onto the estate with you.”

Your eyes bugged out of your skull, and Dean stiffened next to you.

“Dad, this is, sudden, I’m not sure that’s necessary. We’ve only been together two months.”

John raised his hand, stopping Dean mid sentence.

“It wasn’t a request. I expect you to have her completely moved in by tomorrow morning. I know you said she doesn't know a lot, but a little is too much these days.” 

You didn’t know whether you were going to cry or pass out, but John seemed to have sensed your upset state. Placing a hand on your shoulder as he came around the table that made your skin crawl, you leaned in closer to Dean.

“It’s for your protection Y/N. Trust me. Also it won't be so bad here! Most women would give up everything to find themselves in your shoes! Now Dean, take her and get her settled in, you can go and help her collect her things tomorrow.”

With that John left the two of you both sitting alone as the dark sky spread over the expansive lawn.

For just a moment you thought you were going to succumb to tears, but Dean’s hand around yours, lifting you from the table, and leading you through the house that would now be your home kept you grounded and in character.

Dean said nothing, just led you through the overly done halls, and rooms filled with expensive furniture. 

 You got to his bedroom. It was a large room with a fireplace of its own, the same expensive furniture that lined the whole house, and a huge king sized bed. With the door safely closed, you fell into his arms,letting the tears wash over you, and he let you cry it out, picking you up, and laying you down on the satin sheets that covered the bed. Shushing you, and kissing the top of your forehead. 

“I’m sorry sweetheart, I’m so sorry.”

-----------------------------------------------------------------------------------------------

Forever Tag List: @lyarr24 @amandamdiehl @love-jackles-37-blog​ @miraclesoflove​ @waywardsistershy​ @deanwanddamons​ @imabitch4jensen​ @rvgrsbrns​ @bi-danvers0​ @onethirstyunicorn​ @i-love-superhero​ @akshi8278​ @lyss-dw79​ @magssteenkamp​ @lemondropirwin​ @squirrelnotsam​ @hobby27​ @spnbaby-67​ @mrsjenniferwinchester​ @defenderrosetyler​ @screechingartisancashbailiff​ @thecreatiivecorner​  @aflamboyanceofgays @vicmc624​ @busy-bee-angel-misska​ @justanotherwinchester​ @brilovesdeanwinchester​ @idksupernatural​

#jensen ackles #dean winchester #dean winchester fanfiction #dean wincherfanfic #dean winchester x reader #dean winchester x you #dean winchester fanfic #dean x reader #dean x you #mobster!dean winchester x virgin!reader #mobster!dean #spn fanfiction #spn fanfic #x reader inserts #when the lights go out