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#mobster!dean winchester x virgin!reader
holylulusworld · 2 months
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Traders of love (lust) masterlist
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Summary: Our dear readers are in trouble. They sell the only thing they have left. Their body and dignity.
Pairing: Different (multi-fandom) characters x fem!Reader (different reader in every story)
Warnings: angst, kinda prostitution in some chapters, dub-con, extortion, voyeurism, roleplay, smut, virginity kink, pregnancy kink, daddy kink, sir kink, size kink, all the kinks, a/b/o kink, roleplay, loss of virginity, sex for money, blindfolding, a lil bit of feelings, pregnant reader, single mom reader, age gap, DBF trope
A/N: This is not a regularly updated series. It’s a collection of smutty one-shots, with a different character and a different reader in every story.
You can read only single chapters (except for the sequels) they are all connected/in the same universe but can be read as a standalone story. Some (side-)characters will reappear in different chapters.
A/N2: Please head the warnings for all chapters. Some kinks are not for everyone.
A/N3: We will see Lloyd and his reader throughout the whole series. They are the center of the story.
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I’m your daddy now (1) (Lloyd Hansen x Singlemom!Reader)
I’m your daddy now (2) (Lloyd Hansen x Singlemom!Reader)
Swaying (Mobster!Ari Levinson x Dance instructor!Reader)
I’m your daddy now (3) (Lloyd Hansen x Singlemom!Reader)
Like a virgin (DBF!Bucky Barnes x Virgin!Reader)
Chocolate and roses (Mobster!Sam Wilson x Chocolatier!Reader)
Like a virgin (2) (DBF!Bucky Barnes x Virgin!Reader)
Lawbreaker (Lee Bodecker x Sassy!Reader)
French Kiss (CEO!Nick Fowler x Interpreter!Reader)
Best trade ever (Boss!Steve Rogers x Assistant!Reader)
Wallflower (Rich(Mean)!Loki Laufeyson x Florist!Reader)
Lightning and Thunder (Rich!Thor Odinson x Librarian!Reader)
Every move you make (Jake Jensen x WebCamGirl!Reader)
I’m your daddy now (4) (Lloyd Hansen x Singlemom!Reader)
Two for one (August Walker x Pregnant!Reader)
Damage done (Mobster!Dean Winchester x fem!Reader)
Follow the law (Andy Barber x Criminal!Reader)
I’m your daddy now (5) (Lloyd Hansen x Singlemom!Reader)
Under protection (Reacher x Witness!Reader)
Instinct (Walter Marshall x Prostitute!Reader)
Skyscraper (Sam Winchester x fem!Reader)
Make you sweat (Lance Tucker x Gymnast!Reader)
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Undecided addition
Untitled so far (Tony Stark x ???!Reader)
376 notes · View notes
jawritter · 4 years
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When The Lights Go Out Masterlist
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 in a 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
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.
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!!
(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 lose 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 offer sex, Dean is a billionaire businessman 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?)
***BECOME A PATREON***       ***MY MASTERLIST***
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Chapter 1 
Chapter 2
Chapter 3 
Chapter 4 
Chapter 5
Chapter 6
Chapter 7
Chapter 8
Chapter 9
Chapter 10
Chapter 11
Chapter 12
Complete!!
Tags Below the Cut!
Forever Tags: @lyarr24 @amandamdiehl @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​
Series Tag List: 
@royal-sunflower
@roonyxx
@nihilismworld
@prettysourabbie
@rosalynshields
@flamencodiva
@woodworthti666
@stilltoomuchafangirl
@theoneandonlymelol
@deanandnegansbitch
@lunaticgurly
@bxbyizzy
@deangirl93​
@ellewritesfix05​
@moron225​
@kbl1313
@perpetualabsurdity
@someone-you-dontknow
@itmejado
@samsgirl93
@superflurry
@backseat-of-deans-67chevy
@jodibullock1​
@ophelialoveshandsomemen
@kaitlynxo18
@i-have-no-life-charlie
@starchildwild​
@juggysgirlfriend
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maggyme13 · 5 years
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Request List:
Because I happe to get a lot more Requests than usual, I decided to make a Post that contains any outstanding Requests. I will add new ones whenever they are requested. So if I don´t answer to your ask, please take a look at this post :)
The order in which they are listed, is NOT the order I am going to write them in.
I write whenever I feel like writing/ have ideas. So it might take days, weeks or longer before it will be posted!
BE AWARE THAT THEY MIGHT CONTAIN SPOILERS!
The Requests are under the cut:
1.I want to request an angsty one. Where reader is mutant, like she is daughter of Charles and Magneto (genetically) so she can bend metals & read minds. Fury takes her in as she looses her X-Men family. But every one in avengers is not happy about her arrival & are very cold towards her(ik they won't do it but still). She's alienated & is left all alone. End as you like 
2.thor reader Steve smut inspired by Steve lifting hammer? Like reader is mjolnir, like Thor can get his full power only when reader is around cus she is his soulmate. Then Steve reaches his full potential learning it's not Peggy but reader is his soulmate. They have sex rough one maybe?
3.Thor & reader. Where their marriage is arranged & he's not very happy about it, he loathes her basically all angst. Then leaves fir Ragnarok events but when he comes back & sees how she's protecting everyone & fighting for Asgard he falls in love with her apologizes & passionate sex maybe
4.Are you comfortable with dark Clint? Endgame Clint maybe who's very pissed & unlike movie no chance of getting his family back. So takes it out on reader who works for avengers, he thinks she hasn't lost anything & takes all his anger on her. Maybe tries to impregnate her to start a family?
5.dark Thor? Endgame Thor preferably. Where instead of gaurdians, he goes to reader who thinks he's dead and sorta moves on with life so he goes all dark.
6.I wanted to request. In really horny rn so please don't judge 🙈🙈. Can you do a really dark noncon reader, Thor, Steve & Tony. Where maybe they all lost to thanos, and take it out on reader
7.I'm fighting with body imagery issues. keeping this in loop, can you do a Thor reader smut? Angsty fluffyish
8.dark Thor & dark Peter quill. Where maybe when they travel together they find reader(waitress, Idk just a thought) & take her noncon? 
9.reader, Bucky & Steve? Where Bucky is dating Steve and reader as well, reader is oblivious about Steve but Steve knows( loves reader as well) Steve makes move on reader, reader feels guilty & tells Bucky he laughs it off saying he dates her cus he wants Steve to date her too. She gets pissed & stuff. Lil angsty & fluffy smutty maybe
10. noncon? Where reader is stripper & Bucky always visits her place & drools over from afar(reader is oblivious) One day she wears captain America themed lingerie & does her pole dance. Bucky looses his cools & after show goes after her. A rough noncon.
11. Bucky & Steve both sleep with reader(not threesome) when they miss Peggy & Natasha, reader just feels they love her. Once she hears them saying how easy fuck reader is & basically all angst. End is as you like. Make reader happy though
12. Thor, Steve & Bucky with reader. Where reader is basically an intern but they sleep with her (individually) they treat her like an escort. She wants out but they all blackmail her. When they sleep with her they keep degrading her & calling names etc. All angsty. Until one day, when there's a fight,  reader lifts mjolnir. They sorta kneel & respect her?
13. Tony & reader?abo dynamics? If yes, I'd like to request one where reader has crush on Steve & Tony on reader. Once reader goes in heat Tony takes the chance & claims her against her wishes. Maybe she's pregnant later
14. AU where Bucky is famous writer very rich & rude. Reader is simple intern at his office. He fucks her for sake of writing the scene but she falls for him & thinks he loves her. But at opening of his book he brings some girl. This breaks her heart, he also says she's just a good fuck. Angsty. End as you like.        
15. Thor reader & Steve? Where they are in relationship, but it so happens that Steve & thort get competitive as to who fucks reader the best. So to prove the point they have sex with her(individually) give her orgasms, like 3-4 in a row but this exhausts reader. She gets tired, can hardly walk is always covered with hickeys. There comes a point she avoids them & cries to herself. Fluff ensues?
16. request where reader is ex hydra. She's new on team & obviously no one trusts her. They're rude to her, ignore her if she tries to talk, Don't take her suggestions if she makes any. She's left alone until Peter befriends her. He tells the team how nice she is, how helpful she is etc. They feel bad & try to make up but till the time she's transferred somewhere. End as you like
17. scene from killer inside me. It's basically spanking. Can you do a Thor reader based on that? It's on YouTube
18.  request an AU with mobster Tony stark, where he's married to reader who's quite younger than him(I'm 22), but he doesn't see her as wife cus he loves pepper (died or didn't marry due to political reasons) so he only has sex with her takes her raw & rough. Doesn't care if she's hurting, he doesn't talk to her ever. They even have a kid but still he's cold towards her. Then Thor comes, things change then. It's on you what you like, divorce or happily ever after cus Tony gets jealous.        
19. Sam & reader? Where Bucky & reader are in relationship but reader is like a rebound & backup if he doesn't get nat again. He ends up having sex with some random chick, reader sees it. He also mentions her how he had to get himself off with reader like she's not enough. So reader gets all sad develops body imagery issues. Sam had crush on reader anyway so they end up together. Make Bucky regret little  
20. Reader, Steve & Bucky, where reader is Brock rumlow's gf. She doesn't know anything what he does. She thinks he's nice. As to take revenge Steve & Bucky kidnap her rape her & torture her. End as you like    
21. A Viking Steve? Where he invades reader's land, takes her as slave & fucks her raw & rough(noncon) _ shares her with Bucky & Thor maybe?    
22. One where reader is sex slave & Tony buys her for the team(Thor, Clint, Steve). So basically the things they do to her dark, rough & noncon. Maybe later on they get in polygamous relationship?
23.Dr. Strange & Reader? Where reader is his wife & before the accident he never respected her, even though she's a Dr like him, he belittles her, doesn't talk to her, feels ashamed. Later becoming the master, he sees her through portal that how dedicated she is & how dearly she loves him. All fluffy & maybe a passionate love making?           
24. Thor & reader, where reader & Loki are engaged but Thor rapes reader cus he wants her, but feels guilty & goes away. Meanwhile Loki leaves reader saying she's impure. Valkyrie takes reader under her wing & helps her heal. Maybe she ends up pregnant? Happy ending please .           
25. One where Bucky is married to reader but is insecure. Reader is planning to tell him about her pregnancy & plans a surprise. Bucky thinks she's cheating on him & kid isn't his. So he leaves her. Steve helps her through out, Bucky thinks they're together. All angst but fluffy ending.     
26. dark avengers, where they experiment on people to make them strong. They kidnap reader & do brutal experiments on her, to make her strong they physically, mentally & sexually harm her. Idk how to end it. It's on you?  
27.Endgame Thor & reader noncon  
28. noncon reader & Thor, where he wants to breed her. He keeps saying gimme baby over & over. He continues to do so until she's pregnant.
29. Au, where hydra & avengers are kingdom. Reader is married off to Steve. He's not very keen about it. Reader is Brock's adoptive sister, he raised her only so to get in avengers secrets. Reader is oblivious to all this, she's just innocent girl. When avengers find this out they begin to torture her. Amongst this torture she looses her baby. Brock seeing all this surrenders. Readers fate in your  
30. One where Dean Winchester forces reader to give him blow job. Facial humiliation to be precise.    
31. SOA au, abo dynamics where Jax claims reader against her wishes & takes her virginity?      
32. request where Tony dates reader they have sex & he tapes it. His main intention is to bring reader for Steve & Bucky to enjoy? Tony blackmails reader saying if she doesn't comply he'll upload that tape for everyone to see. Bucky & Steve take her rough & new noncon.
33. Could you do a lactation kink of Steve? Reader is pregnant with Bucky's child, Steve can't control how soft & big her boobs get. One day he looses his control & tears her shirt & sucks on her boobs. Reader feels humiliated & tells Bucky. Bucky supports Steve & shares her with him even though reader doesn't want it.
34. One where Peter & reader are siblings, children of Tony stark. Reader is elder one & never been treated right by avengers. Peter is always favoured, pampered etc. Reader is left alone even though she's smart. Reader is married off to Brock rumlow, but he's abusive (physical &sexual). Avengers don't know, once Peter gives her surprise visit& sees her bruises & brings her home. Fluffy ending? Sorry if it's confusing. 
35. How bout sex slave reader, who's new in business & is really young gets bought by Tony for Steve? She develops feelings for the man, but he doesn't. Can you make a holy trinity, smut, angst & fluffy ending. Thank you 💛                      
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jawritter · 4 years
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When The Lights Go Out
Part 1
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: 2358
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: None really, language, escort serives, angst? I think that’s it for this chapter!
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***
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Adjusting your too short skirt, you look across the crowded street from your hiding place among the crowd of people standing on the side of the road waiting for their cab, or Uber to pick them up from whatever they had just left, or take them to wherever they intend to go. 
Heavy thunder rolled over head, and you looked up at the ominous black rolling clouds that from your street view made the skyscrapers look shorter than they really were.
Your heart was pounding so loud in your ears that it drowned out all the sounds of the hustle and bustle that was New York City on an average Friday night. Even though, in reality no one noticed you, you looked no different than about six other girls standing within a four foot proximity of you, you felt like every eye was on you. Like they were judging you, and knew just what you were doing, and just who you were waiting for.
Even though you weren’t meeting this man for sex, you felt like you were no better than the whores that line the streets of Brooklyn late at night, like cattle lined up for a sale barn to go to the highest bidder. 
Claire had suggested that you join the Sugar Daddy App in order to make a few extra bucks after losing your job as a junior accountant at JP Morgan. You hadn’t been there all that long, and when they changed management, your new female boss seemed threatened by all the females in the office, especially those like yourself, those that were young, those that had potential; so therefore you got the first axe. 
You didn’t really like the idea, but you were really left with no choice. Even though New York was a big city, it didn’t make jobs exactly easy to come by, and you need money before next Friday, or you would be living under one of the many bridges. 
It hadn’t taken long for Dean to respond to your add on the app as a paid escort, and the fact that you weren’t offering sex didn’t seem to bother him when he’d direct messaged you. He said he just needed you to attend a business party with him, a promotion for his brother, and if you did well, he might hire you permanently. 
Claire seemed to think that you had hit the jackpot, and told you to jump on the opportunity, but the amount of lucid information that he’d given you as far as what to wear, and that you were to just be on his arm to “look pretty”, you couldn’t help but feel you were dealing with the mob. 
You knew that was a silly notion.There was only one mob left in New York that had enough power behind them to even be threatening. Everyone else was nothing but grunts under them, and there was no way in Hell a Winchester would be using a Sugar Daddy App in order to find someone to take to a business party with him. 
Claire said not to worry about it, and that you were looking into things to much, that you had watched to many Scarface movies, and this was probably just a businessman who was in his forties, overweight, and lived in one of those box cublicial apartments on Manhattan with too much money, and not enough social life to bring someone to the event. 
You had your doubts.
The way he worded things, so secretive, so proper, it had you scratching your head from the moment you agreed to this job as to whether or not this was a good idea, or if you were going to be the next featured picture on the back of a milk carton as New York’s latest missing person. 
Just as you were about to say fuck it, and turn around and head back to your apartment, a sleek, black SUV pulled up to the curb and stopped. Looking around you notice that everyone that was standing next to you just a few moments ago had all but vanished, either getting into their own means of transportation, or giving up all together and deciding to hoof it. 
The window directly in front of you rolled down just enough for the baritone voice to filter out of the dark interior of the car. 
“Y/N?” he asked, and you stepped forward cautiously. If you weren’t regretting this before, you were now. 
“Yes?” you said, stopping just short of the curb. 
The driver’s side door opened, and the short driver made his way out of the car, and around the back passenger door that was facing the road. He opened  it for you to climb in as another round of thunder rolled, and thick raindrops started to pelt down all around you.
This was it, there was no going back now. 
Swallowing the little voice that was screaming how bad of an idea this was, you climb into the back of the car and the driver shuts your door before making his way around to regain his seat at the helm of the car. 
“Well, I must say you are attractive enough, but you look terrified sweetheart.” the same deep baritone voice said across the dark back seat next to you as the diver pulled out onto the street. 
Straightening up in your seat, you adjust yourself and try to look less like a scared child, and more like the paid escort you were for the night.
“Well, I’m sorry Dean, but as I told you earlier, the fact that you were so secretive concerning the details of our evening made me a little uneasy. Most clients tell you where they’re going to take you, and what you are going to be doing for the evening.”
Dean chuckled next to you, and adjusted his tie.Even though it was dark in the car, the street lights let you make out his strong jawline, and handsome profile enough to know this was not some overweight businessman. He was much more than that. 
“I think we got off on the wrong foot. My name is Dean Winchester, and I’m hiring you to escort me to my brother’s dinner party in celebration of his promotion in my father’s company.Judging by your slack jaw, you’ve heard my last name before, and you see why it wasn’t exactly a great idea for me to put my last name, nore the details of our arrangement in a direct message on some crude app.”
You set there in total dumb founded shock. 
Of all the people you thought were going to be picking you up tonight, Dean Winchester was not one of them. You had feared that this was a mafia pick up, but this was much worse. 
Dean wasn’t only Mafia,  he was son of the oldest, most lucrative gang in New York City’s history, his father, John, made Al Capone look like a little boy dressed in a suit. His family were ruthless, and virtually untouchable, protected by money, and  God only knows what else you couldn’t even begin to imagine. They didn’t hide what they were because they didn’t have to, and you were  more fucked than you thought you’d ever be. 
“My brother Sammy’s promotion details are not important. The only thing you need to know is that for the evening you are my girl, and you will do as I say. Talk as little as possible, and like I said, just look pretty. That won't be that hard for you. Stick close to me, but I promise you, this is continental ground, and no one can harm you in any way. So just relax and enjoy the party.”
Dean was completely unfazed by the fact that you still seemed to be in complete shock, like this was the reaction he was expecting from you. He knew that this was your first job? Why the hell did he hire you for something this big? If you weren’t already having a panic attack, you were pretty sure you were going to by the time you got to where you were going. 
“Dean, I...Look I don’t...I don’t know if this is such a good idea.What if they don’t buy that I’m your girlfriend, and furthermore why do YOU, of all people, need help getting a girlfriend?” you asked. Dean threw his head back against the seat of the car, his deep booming laugh echoing through the entire car. 
“Sweetheart, relax.You're perfect. I didn’t want someone with experience. Escorts in my line of work are, well, a commonly used expense, and I didn’t want someone that is recognizable to anyone that is going to be at this party tonight. I wanted this to be believable. As far as why I need you? Well that’s easy. I’m 40 years old, and unmarried, but I’m also my father’s successor to the company.The only problem is, the high table seems to think that I should have a wife by now, and I don’t, so you are here to keep my father and my elders off my back.” Dean said shortly as the car came to a stop in front of The Roosevelt Hotel.
Dean reached into a folder that was sitting on the seats between  you, pulling out a stack of papers that were stapled together, and handing them to you. You took them with what you knew had to be the most bewildered look on your face that anyone had ever had, but Dean seemed to be unfazed as the dome lights were switched on inside the car, and Dean handed you a pen. 
His large, freckle dusted hands, made everything they touched seem so small, and you wondered how many people those hands had killed before you buried it deep down inside of you, not letting the thought manifest. 
This man was dangerous, but you needed the money.
“This is a NDA.It says that you can not disclose your employment with me, nor anything else you will witness here tonight as long as you live. It’s virtually a gag order. It’s for your protection, not mine.” 
You nodded your head and swallowed hard, not daring to ask what the hell would happen to you if you broke said agreement, and signed the papers, knowing you had no choice. 
Looking up at the astonishing greens eyes staring back at you, you fought against the deep blush that pooled through your cheeks. Dean was handsome, and there was no denying that. 
“Okay, so, I know you said no sex, which quite honestly is a shame,” he said, looking you over in the small space, his perfect white teething pulling at his lower lip, making you blush even deeper than you already where, “but in order to make this convincing, there’s going to have to look like there is some degree of intamicy between us. In other words, I will hold your hand, touch you, tastefully of course, we're not animals, and I may even kiss you if need be, is that okay?” 
The thought of those pink, plump lips on yours made a shiver go all the way down your spine, and you had to look down for a moment to compose yourself. 
“Yes sir, that’s fine.” 
Dean chuckled as he opened his car door, getting out to open yours, his large, warm hand going to your lower back as he pulled you in close to him once you stepped out of the car. 
“Call me Dean, Baby Girl,” leaning down so that only you could hear him, his warm breath fanned over the skin of your neck, and goose bumps raised all over your skin, “or you can call me Daddy, I’m okay with that too.” 
You blushed furiously and covered your face with your hand, a deep embarrassment at the way your body seemed to be responding to this man standing next to you on the curb of the crowded street.  Another booming laugh escaped Dean as he pulled you into a hug. People were apparently watching that you were unaware of , because the act seemed to have already started. 
“I’m only teasing you sweetheart.I love to see you blush.Remember, impress me tonight, and this job is yours permanently, and I promise you, I will pay you so well, that you will never want for anything ever again.”
That was a promise you could get behind, so you straightened your skirt and took him in for the first time in the light of the foyer as you  walked together, your arm over his own in a formal manner suitable to the occasion. 
You hadn’t really looked at him until now, and man, he was a sight. 
Danger reeled off of him.From the ridiculous expensive, black, custom fitted Brioni suit, and crisp white Ralph Lauren shirt, to his only God knows how expensive black shoes. 
He was lethal, and he had no problem not hiding it. 
His piercing green eyes held an air of mischief that excited you in a way you’d never experienced before. Not a hair out of place, except for the almost auburn stubble that matched his perfectly placed hair sprinkled across his chiseled jaw, and a smirk that could melt the panties off of every woman in the room. 
He carried a presence about him that commanded attention, and you could tell by the faces of the people that were watching the two of you as you both checked in to the black tie event the hotel was hosting for the Winchester family, that he was the man that everyone loved to hate. 
This was the craziest thing you had ever done in your life, and it would probably one way or another end badly, you knew that, but his was the most alive you had felt in your life, and you were determined you were going to enjoy the moment on Dean’s arm, and worry about the rest later. 
Besides, what was life without a little adventure, and it was high time you had yours.
----------------------------------------------------------------------------------------------
Tag List: @lyarr24​ @amandamdiehl​ @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​
Series Tag List: 
@royal-sunflower​
@roonyxx​
@nihilismworld​
@prettysourabbie​
@rosalynshields​
@flamencodiva​
@woodworthti666​
@stilltoomuchafangirl​
@theoneandonlymelol​
@deanandnegansbitch
@lunaticgurly​
@bxbyizzy
@deangirl93​
@ellewritesfix05​
@moron225​
454 notes · View notes
jawritter · 4 years
Text
When The Lights Go Out
Part 2
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: 2796
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: John is a creepy asshole, nervous reader, dangerous mob situation, language, escort services, I think that’s it.
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!!
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***SERIES MASTERLIST***
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You had lived in New York since you were about five years old, and you had never been inside of The Roosevelt Hotel until now. It far surpassed what you expected it to be, and to be honest it was a lot too rich for your blood. 
Looking around at the room filled with small tables and extravagant decorations, candles, and waiters, you felt like you had stepped onto the set of a movie, rather than a party. Everything was so beautiful, so elegant. People of all nationalities in black tie suits, and formal cocktail dresses fluttered around the room, either sitting at the tables, or gathering in small groups with glasses of expensive champagne or scotch in hand. The light buzz of conversation filled the room as the live band played on a stage in the corner. 
You barely had time to take it all in, when an older man wearing an earpiece stepped up to Dean as the two of you made your way towards the table at the top of the room. 
“Dean.Your dad wants to see you. He’s waiting in room 122.” the older man said. He looked very uncomfortable in his suit, pulling at the tie around his neck subconsciously. 
“Rufus”, Dean said, nodding at him as he eyed the man with a smirk on his face, clearly amused by the man’s appearance in front of him, “what exactly did my father have to do in order to convince you to put on a suit?” 
Rufus did not look amused at all, giving Dean a look that said if they weren’t standing in the middle of this crowded room, he would have made him regret that smirk plastered all over his beautiful face. Dean, on the other hand, seemed thoroughly unfazed. 
“Boy don’t test me. Now your dad said to move your ass upstairs with your date, or for me to move it for you.Your choice.”
Dean’s features hardened, and he leaned over and whispered something in Rufus's ear that had him raising his eyebrows, before quickly looking down at the ground.  
Adjusting his suit coat, Dean leads you towards the elevators at the opposite end of the room. His face is still hard, and his shoulders stiffer than they were a moment ago.
Once you were both safely inside the elevator, Dean turned to you, looking at you almost like he was sorry for what was about to happen. That made you even more nervous than you already were.  
"Y/N, I want you to follow my lead no matter what," he said softly, grabbing your shaking hands in his. "Don't worry, my Dad looks scary, but he would never do anything to harm you. He probably just wants my signature on some paperwork from earlier today." 
Dean’s piercing green eyes searched yours, almost as if to see if you bought the lie that he just tried to dish out in order to calm your obvious fear at meeting his father.
"Dean... I don’t know how I feel about this. This is more than a simple escort service.” 
"Just, don't ask questions okay. Let me do the talking. I promise you, the less you know the better, so please don’t ask me any questions. I know I took a risk asking you to come tonight, but I promise you Y/N, nothing is going to happen to you, and the less you know about my business the better okay? Trust me, I’m not going to let anything happen to you tonight.Remember our agreement?Just stand there and look pretty and you will be just fine." 
In a bold move, Dean placed his hand on the side of your face in an almost comforting way, and you couldn't help but lean into the warmth of his hand. It was almost like the man had a spell on you, and the longer you were around him, the more you were drawn to him. You couldn't help but wonder if everyone felt that way around him.
When the doors opened, Dean linked his fingers with yours, and led the way to the room where you were both instructed to meet Dean's father . A body guard in a nice suit opened the door for the two of you and let you in before Dean could even say anything, closing the door behind you both quickly. 
The room was darker than the hall, and it took a minute for your eyes to adjust, before you saw the man standing in the window looking out over the city. His broad shoulders and strong back held  the same air of confidence you saw in Dean. 
"You wanted to see us?" Dean said, and the man turned around slowly. His black beard and hair were the first thing you noticed, his eyes made to look dark by the light of the room. He didn’t move any closer to the two of you, but he did seem to scan you from head to toe, and you shifted a little closer to Dean. 
"Yes, I wanted to see the lady friend that you brought here tonight. I was unaware that you were seeing anyone Dean." he said, turning his head to the side a little, the same amused smirk you had seen on Dean earlier this afternoon playing on his lips. 
You kept your mouth shut, just as Dean instructed. Honestly, you were a little afraid of this man, and you were too scared to say much of anything at the moment, because you knew you were in over your head.
Way over.
Dean blinked at his father, an annoyed look on his face. 
"Dad this is Y/N, my girlfriend," Dean lied smoothly, "Y/N this is my father, John Winchester." 
John said nothing, just looked you over again, and took a deep sip of the amber liquor in his glass.
"You look young. How old are you Y/N?" he asked, and you felt Dean stiffen a little next to you.
"I'm 23 sir." you state, attempting to sound confident. John just smirked, before turning his attention back to his son.
"At least she seems to know her place. Tell me Dean," John moved a little closer to the two of you, but still kept his distance. "does your girlfriend know anything about our company?"
Your heart leap in your throat, and for a moment you wondered if he was going to kill you both, because you were becoming more and more convinced by the second that this man was the living equivalent of the Godfather.
"No sir, our relationship is.... new." Dean said, choosing his words wisely. 
"Prove your together." John stated bluntly, and your eyes almost bulged out of your eye sockets. 
"I'm sorry, what?" Dean said, blinking at his father, seemingly as shocked at his declaration as you were.  
You hoped that John couldn't see you trembling where you stood. White hot fear gripped your gut, and you wanted to run away, but you had a feeling you wouldn't get very far.
"Prove it." he stated calmly, taking another swig of his glass. "I see she's clinging to you, but that could be out of fear, or what you've paid her to do. So prove it." 
John had a full on smirk on his face now, and you couldn't help the sickening feeling that flooded your stomach at his gaze.
Without hesitation, Dean spun you in his hold, your chest meeting his. Before you could even react, he had leaned down, and captured your lips in his, kissing you deeply, his tongue slipping between your lips with ease, and his hand sliding down grabbing your ass, pulling you tight against this body as he kissed you drunk. 
You couldn't stop the blush on your face if your life depended on it as he pulled away from you, and you quickly looked down at the floor.
John chuckled across the room, and clapped his hands as if he were watching a play.
"Good, very good, for a moment I thought you had hired an escort Dean, but I see she's a little too shy to actually be a working girl." 
Your blush deepened, and you hid a little closer to Dean's chest.
"If you done harassing my girl, I think we're both due downstairs." Dean said coldly. 
"You’re right.You two go and enjoy the party, I'll be down shortly. I like this one Dean, and you are going to need a wife soon if you're going to take over our... company.I hope this one sticks." he said, his voice dripping with venom as Dean turned and led you both quickly out of the room. 
You didn't take a breath until you were both in the elevator. You were visibly shaking when Dean pulled you in this hold, his strong arms wrapping around you, and his cologne invading your scene. 
You knew that could have gone much worse, but you were still very shaken up by what John had asked Dean to do in there, and his threat of ,‘I hope this one sticks,’ didn’t go unnoticed by you or Dean.
"Fuck sweetheart, I'm sorry." Dean said, lightly placing his lips to the top of your head, and wrapping his arms tightly around you, pulling you deeper into him as the elevator descended lower.
Dean sounded just as relieved as you were to be away from his father, and you did all you could to try and keep yourself from passing out from the impending anxiety attack that threatened to take over in the dark corner of your consciousness.
These men were lethal, dangerous, and probably murderers or worse, and they have seen your face. 
You were fucked. 
It felt like the universe had decided to get you back for every stupid thing you ever did. All in one night. 
Great.
Dean released you from his hold, and placed his hand on the side of your face softly, making you look up into his deep mossy green eyes, searching yours for any sign that you might freak out on him, or crack.
"I need to know if you're okay, because when those doors open it's going to be all eyes on us." Dean said seriously, but at the same time you could hear the concern in his voice. Now whether that concern was for you, or for his own well being you couldn't tell.
"I'm okay, I swear, Just.... Don't kill me..." you babbled stupidly, a single tear sipping down your cheek that Dean quickly caught with his thumb. 
"I'm not going to kill you, no one is going to hurt you, you're safe with me okay? Now calm down. Let's go get some drinks, and let me show you a good time tonight. There's no reason why we can't enjoy the rest of the evening together." Dean said, his voice calm and soothing.
The elevator doors opened and you took a deep breath before taking his arm once again, letting him lead you to a well dressed table in the ballroom where a waiter brought drinks for the two of you. Dean's arm wrapped around your shoulders protectively, and you instinctively leaned into his hold. 
You know that you should be terrified of him, but there was something about him that was calming to you, like he could keep you safe when nothing else could. 
You didn't miss the smirk on his face when he felt you move closer to him, and he made sure to keep the small talk light, asking you things about where you grew up, your favorite things, and before long he had you laughing at some of his childhood stories. 
Yes, you grew up worlds apart, yes he was seventeen years older than you, and yes this was a paid date that he was probably trying to do his best to look real between the two of you.You had a feeling if his father found out that you were just a hired date, you’d both be fucked six ways from Sunday, but you couldn’t help but get lost in his laugh, the way his eyes seemed to dance with mischief as he looked at you, the way his hand felt heavy and warm against your shoulder, or the way his very presence seemed to command the attention of everyone that came within five feet of him.
He was everything a girl wanted, and something you didn’t even know still existed . Too bad he wasn’t really yours. If you were lucky enough to live through this ‘date’ you’d probably never see this man again. You were sure after that little display in the elevator where you begged him not to kill you, he’d never hire you again.
The evening drew on. A speech was made by John, then Sam. Nothing incriminating, or anything, just a lot of thank you messages, and other formalities. As dinner was served, Sam joined you with his fiance Jessica. John stayed busy at an even bigger table.  
You liked Sam and Jessica.They seemed a lot more down to earth and a lot less lethal than everyone else in this room, though you weren’t fooled in the slightest. They were just as dangerous as Dean and his father.
Dean led the conversation, and you did what he asked, just sitting there looking pretty, and leaning into him at the appropriate times, mainly when you saw John’s eyes filter to the two of you.
When the evening was finally done, and Dean had said his goodbye to his brother, he grabbed you around the waist, and whisked you towards the exit.You were grateful this was over, and you were more than ready to get back to your little apartment, and back to reality. 
Dean had almost had you to the car when a voice boomed from behind the two of you, stopping you in your tracks.
"Dean! Hang on a second!' 
Dean took a deep breath, giving you an apologetic look, before turning you both around to face John who was standing very close to you.
"Yes, sir." Dean said, holding himself up a little straighter.
"I didn't get to say goodbye to your lovely girlfriend!" he said, grabbing your free hand and kissing the back of it, his dark eyes meeting yours, a smirk on his face.  
"do svidaniya krasivaya devushka." he said before dropping your hand, and you leaned closer into Dean's hold.
"English please Father. She doesn't speak Russian." Dean said, a little colder than what you expected him to address his father.
"My apologies dear, I simply said goodbye beautiful girl." John said, smiling sinisterly at you before turning his attention back to his son, not giving you time to respond.
"I trust that this lovely young lady will accompany you to our family dinner this Sunday? It will be nice to see the normally empty seat at the table filled for once.”
Dean never relaxed his stiff posture next to you, pulling you so close to him that you had to put your arm around his back in order for it not to look awkward. 
“Well I hadn’t asked her yet, but if she’s not already got plans, I’m sure she will attend.” Dean said stiffly. 
"Of course. Good night dear, I hope you had a lovely time. Now Dean, go break that girl in, she seems barely driven. No woman of my sons will allow him to go to bed unsatisfied I trust." he said, turning on the spot and leaving Dean to hurry you into the warmth of the car that had driven you up here.
Dean huffed in aggravation, turning sharply and opening the door to the car, before helping you inside it’s warmth.
You took a deep breath as soon as the door was shut, and Dean's hand landing on the back of yours made you nearly jump out of your skin. He smiled softly at you.
“I really am sorry about my father’s behavior. I promise that was directed at me, not you. He was doing that because he knew it would get under my skin.” 
Pulling an envelope out from under his seat, Dean passed it to you.You could feel that it was quite full. 
“This should be sufficient for tonight. We will discuss Sunday a little closer to time.”
You nodded slowly, almost afraid to open the money and see how much was there.
“So...That means..I have the job?” you asked, your voice small as the car pulled up to the curb of your apartment building. Dean smiled at you softly, bringing his full lips to the back of your hand, before your door was opened by the driver. 
“Oh sweetheart.You had me at hello.”
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jawritter · 4 years
Text
When The Lights Go Out
Part 3
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: 2063
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: embarrassed reader, hint of insecurities, brief description of injury, language I’m sure, because it’s me people. Some angst, I think that’s it, this chapter is actually pretty mild. 
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***
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To say that Dean had paid you very well for your date together last Friday night was an understatement. In fact, he’d paid you so well, that you were able to  get caught up on all other bills that were due, and still have plenty of money left over. 
It wasn’t about the money for you though, not really. It was about the fact that you had spent every moment, waking and sleeping, completely, and utterly infatuated with the green eye man that had hired you as his permanent escort. 
I mean how could you not? He was literally the most attractive man you had ever laid eyes on, and even though this should have been strictly business, you were already developing quite the crush on the man. 
Sure, working for this guy could literally get you killed, and you weren’t sure that John wouldn’t do it his damn self if he caught the two of you, and learned that you weren’t really Dean’s girlfriend, but you still couldn’t stop yourself from checking your DM’s, and hoping your phone would ring with that baritone voice on the other end that seemed to make you melt without even trying.
It was just getting dark. The sun was setting just behind the skyscrapers that made up the New York skyline, casting beautiful shades of pink, and gold over them, the light of autumn hanging in the air as the season ready themselves to change. It was your favorite time of day, so you found yourself sitting in your chair next to the window with a cup of hot coffee in your hand, and a throw blanket over your lap, just taking it all in.
Your mind drifted from Dean, to your future, to the upcoming event on Sunday that he’d yet to contact you about. That event you tried to not think about, just thinking about it made your anxiety spike to an all time high. 
The last time you were in the same room with John Winchester, he’d ask you to prove your relationship with Dean. When you left the party, he’d made that crude comment about you making sure his son went to bed well satisfied. Only God knows what he might ask you to ‘prove’ in front of him concerning Dean, and that made your chest tighten uncomfortably.
Not that you didn’t want to have sex with Dean, I mean my God most women with a pulse, and some men, would give their left arm to have that opportunity. The problem with you resided with the fact that you had never had sex with anyone before.
Dean didn’t know that little fact about you, and you were terrified of what would happen when he found out. 
You hoped your inexperience wouldn’t blow your cover, and you knew you had to tell Dean eventually, even though your contract with him stated that having sex with him wasn’t something you offered as part of the job.You knew that if you continued to play the part of ‘girlfriend’ to him, it was going to come up.
A loud knock on your door nearly made you jump out of your chair, and you made your way slowly to the door of your apartment. 
Your only friend was away on business, and you didn’t know who else would possibly come calling. Your little ‘date’ with Dean had made you paranoid as to what might come after you, and you looked through the peephole in the door trembling as if a monster was going to be on the other side of it. 
When you saw Dean, your heart leapt in your chest, and you ripped the door to your apartment open like a teenage girl, greeting her crush. 
“Hi!” you said breathlessly, opening the door wider and allowing Dean to come in. His tall silhouette slipped  past you, and into the apartment on bowed legs that made you weak in the knees. 
“Hi, I hope I’m not intruding on your evening, coming over unannounced.” 
Dean looked around your apartment as you closed and locked the door behind you, turning to face you as you crossed the floor to him.
“No, not at all, I was beginning to wonder if you had found someone else to escort you Sunday.” you said, looking down and playing with the hem of your sweater nervously. 
“Not at all, I was busy with a job, and I’ve only just now got back to New York, or else I would have come to see you sooner.”
Motioning to the small couch in the center of the room, you both sat down, Dean, situating himself very close to you on the couch, closer than you expected. 
“I know this might seem forward, and I know that I’ve asked more of you than a normal escort service would have ever offered, and by making you exclusive to me only I’ve kinda brought this to a whole new level that I’m sure you were not anticipating, but in order for Sunday to go off without a hitch, the two of us are going to have to look like an actual couple.” 
Fear settled deep in your stomach, as his hand reached for yours. 
“You’re trembling sweetheart. Are you afraid of me?” he asked, his thumb rubbing little circles on the back of your hand in an attempt to be calming. 
“A..a little bit..” you admitted sheepishly, avoiding his gaze.
Sliding over closer to you, and throwing his arm around your shoulders, he settled the two of you in his hold. The smell of his cologne seemed to pull you in, and cloud your judgment, calming you instantly. 
“You have absolutely nothing to be afraid of. I’m not gonna hurt you, and I’m not going to let anyone hurt you. I’m a gentleman, pretty girl, and I’m not going to make you do anything you're not comfortable with if that’s what you're worried about.”
Taking a deep breath to steady your nerves, you look up to meet those green eyes that had been haunting you since the moment you met him. They were softer than you expected, and something radiating through them just said that he was telling you the truth, and it was okay to trust him. 
“There’s something you need to know Dean.” you say, shame of your confession making you blush before you could even get it out, his fingers brush your hair off of your shoulder, playing with the loose strands at the base of your neck, bringing goosebumps to the surface of your skin.
“That you’re a virgin.”  Dean said, stopping you in your tracks.Your eyes were as big as dinner plates as you try to hide the deepest blush you had ever experienced in your life. You covered your face with your hands. 
“It’s nothing to be ashamed of sweetheart. I figured as much the moment I kissed you in my dad’s hotel room, then there was also the no sex policy on your offer. Which I don’t have a problem with in the least, don’t get me wrong, but virgin or not makes no difference to me, or our arrangement. What I do need for you to do is to get comfortable with me touching you, because we need to look more natural Sunday than we did Friday night.”
You looked up to meet his gaze as his fingers lightly brushed the skin of your neck, pulling you closer to him. His warm body pressed against yours. 
“Is that why you're here?” you asked him, and Dean nodded his head, his eyes searching yours for any sign of hesitation.
“The more time we casually spend together, the easier it will be for you to be around me, having me touch you, kiss you if need be, and it be believable.”
Relaxing a little into his hold, Dean brought his hand up to the side of your face, brushing his thumb over your cheek before lowering his lips to yours, brushing his lips over yours in a chaste kiss. 
Even though it was brief, it still had shivers shooting down your spine. 
Dean smiled cockly at your reaction, his fingers dancing little trails down your arm, and back up again.  
“So you show up just to makeout with me? That’s not very professional is it Dean?” 
Dean threw his head back in a whole body laugh that made you blush yet again, his lips coming back down on yours in a little deeper kiss, before breaking it suddenly. 
“You could say that,” he said, still chuckling to himself, “what can I say, I’m a method actor.” 
It was said as a joke, but for some reason it stung. Like the only reason he was here was to prepare you to give  a worthy performance in front of his family. 
Sitting up and away from him in order to clear your head, you grab your remote, and turn on your TV in effort to ignore him. Dean seemed unfazed. 
“The dinner is tomorrow, I figured we could both get ready here at your apartment and leave together.” Dean said, kicking his feet up on your coffee table, grimacing as he did so, making your eyes travel him as if you could see whatever it was he was trying to hide.
“So, you're staying here all night?” you asked him. His face hardened a little before he switched off your TV, and looked at you more seriously than before. All joking and flirting disappearing from his features. 
“I’m going to level with you, but I don’t want to scare you, so do you trust me?”
Nodding your head against your better judgement, you folded your legs under you, and turned to face him. Your heart pounded in your ears so loud you were sure he could hear it..
“I think my father has some of his goons following us. He doesn’t trust me, and in order to make this look real, I need to spend time with you like I would my actual girlfriend.”
Your eyes bulged almost out of their sockets, and Dean leaned forward with some effort, grabbing your hand in his before he continued to speak. 
“I’m sorry, I feel terrible for ever getting you into this with me. I didn’t expect for them to actually like you, or for me to actually like you for that matter, but that’s a conversation for a later date. There are a lot of things you don’t understand, and I know that you don’t trust me, and you have every right to hate my guts, but I swore I’d protect you, and that’s what I intend to do. You didn’t ask for this, I pulled you into it.” 
Dean took a deep breath, and his free hand traveled to his side, before he could stop himself. Your eyes drifted to there, and before you could stop yourself, you lifted his shirt looking at a deep purple bruise right over his ribs. The color drained from your face. You were in way over your head. Not only were you bound to the Son of the Godfather of the fucking Russian Mafia in New York City, but he was apparently injured, and sitting here on your couch.
“Dean? Did your dad do this to you because of me?” you ask him, fear evident in your voice.
Shaking his head Dean pulled you closer to him, wrapped his arms around you, and turned back on the TV, signalling this conversation was effectively over. 
“No, that was a business deal where someone thought they could get over one me. That had nothing to do with us, or my father, just part of the job.” he said, giving you a peck on your lips before settling both of you into the couch. 
You lay there quietly letting him trail his fingers over your arm and back, before long his breath became deep, and even. Looking up his features soften in sleep, and a light snore feel from his perfect lips. 
You foolishly wondered if he was here because of your arrangement, or he just didn’t want to be alone. One thing for sure, this just kept getting deeper and deeper, and you wondered just how deep this rabbit hole was really gonna go before the walls started closing in.
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333 notes · View notes
jawritter · 4 years
Text
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***
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“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.”
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jawritter · 4 years
Text
When The Lights Go Out
Chapter 5
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: 2369
Series Warnings: Mob level violence, injured Dean, description of injury, creepy Godfather John Winchester, John is pretty much a douche 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: Angst, Fighting, Angry Dean (yes that’s a warning), John being the douchebag he is, language, I think that’s everything. 
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***
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Two weeks.
That’s how long you’d been in the prison that was the sprawling Winchester Estate. 
Well to you it was a prison anyway, to anyone else standing from an outsider's perspective, you hit the jackpot.
You, on the other hand, didn't feel so lucky.
You felt trapped, and alone. No matter what Dean did to try and make it better, no matter how close you and Jess had become over the last few weeks, it wasn’t home, and that’s the whole reason you joined that whole Sugar Daddy app to begin with. Now you didn’t even have that.
You knew that you had gotten in way too deep when you first met Dean Winchester, but damn if you didn’t know that you had gotten in that damn deep. 
Now, you had lost your only home you’d ever really had, along with what felt like your freedom to live and move like a normal human being. 
Dean had tried. He really had. He felt horrible about what John was making you do, and he and Jess helped you pack up everything in your apartment the day after John’s declaration. That was probably the hardest thing you had ever done. Keep up the happy couple act for Jess, while silently you felt like you were dying, or wishing that you would. 
That’s when you really started to resent Dean Winchester. 
If he would have just left you alone, if he  had never contacted you, if you had never got into his SUV that Friday night, you wouldn’t be in this mess, and better yet, if he would have been man enough to tell you the fucking truth about who the fuck he was, you wouldn’t be in this mess. You would have never agreed to go on that God forsaken “date” with him in the first place. No matter how much money you needed, or how fucking attractive he was. 
The first week that you were here, Dean really tried to spend as much time with you as his “work” would allow. Taking you out to get ice cream, down to the peer to watch the boats, anything and everything he could think of. 
You couldn’t tell if he was just trying to keep up the happy couple act for his family, or if he just felt guilty, and was trying to make it up to you.
That just drove your resentment deeper. 
You were forced to share a bed with him, but mercifully it was large enough that you could throw a pillow between the two of you to use as a wall, keeping him at bay, at least mentally anyway, and still have enough room to sleep comfortably. 
The first night you did that, you could have sworn the most hurt look you had ever seen on a person crossed his face, but he hid it quickly, and now when he got into bed, whenever that was he just turned his back on you, and fell asleep, or passed out, because Dean had taken to drinking a lot. 
Week two started, and you barely spoke to each other inside your shared room. Only on the outside of the room did you even attempt to act like a couple with him, and that’s because you didn’t want to die. 
When the second week started, John had started taking Dean on a lot more “jobs” with him, and usually they were gone late into the night. When Dean finally did stumble back in the door, he recked of whiskey, and stumbled to the bed without so much as a good night, or fuck you, just like you were another piece of expensive furniture that filled the room. 
You didn’t ask Dean about his work.You didn’t ask Dean about much of anything.You found it easier just to ignore each other. 
Tonight was no different. You had spent all day working on the transcript that your new job Dean had got you, just like he promised, had sent you. 
You were thankful for the job. It was a nice distraction from the reality you now found yourself in, even if you knew Dean probably only got it for you to cover his ass. 
Dean had been gone all day with John, which freed you up to move around the house without risk of being caught by John, who you tried to avoid with everything in you.  Something about the man just made your skin crawl. Still today you had work to do, and that’s what you did, from the moment you woke up to the empty bed, Dean on another “job”, to the point where a knock on our door disturbed you from your distraction. 
“Hey woman! You’ve been hauled up in here all damn day! Care if I join you?” Jess asks, coming in without invitation and flopping down at the foot of your bed. 
“Be my guest. Nothing really all that exciting here today though,” you tell her, typing away on the computer in front of you.
“You're still working? You do realize it’s almost seven in the evening right?” she asked, shock clearly evident in her voice. 
Looking up at the clock on the wall, you look back down at your computer with wide, burning eyes. You hadn’t realized that it was that late.You had successfully wasted the whole day staring at this computer. 
“No, I hadn’t realized it was that late.” you mumble, shutting your computer, and shoving it away from you like it might come to life and attack you, earning a smile from Jess.
“Well come on.The men are home, and it’s time for dinner. I haven’t even seen you leave this room today, so I know you probably haven’t eaten. Dean won’t be happy if you get too skinny now will he?” she said with a wink.You forced a chuckle in response, but said nothing in fear that you would blow your cover, and Deans. 
Truth be told, you weren’t sure Dean would even notice you died, much less lost weight. 
Getting up from your perch on the bed, you stretch and follow Jess to the dining room where you could hear the men’s voices filtering in from the hall. Bracing yourself for another acting session, you take a deep breath, and step down into the room.Thankfully, they were all so immersed in conversation that they didn't even see you two walk in. 
Jess took her seat next to Sam, and you next to Dean as the maid came into the room  with the butler that you didn’t even know the name of, and started to plate everyone’s food. That was one thing that you just couldn’t get used to. People waiting on you hand and foot that way.
“Well I’m telling you Sammy, another person in the car is nothing but another liability, and Dad and I can move in and out easier with just the two of us,” Dean said, not even acknowledging you sitting next to him. 
“I agree with Dean. Sam, stay here and watch over the ladies. Dean and I will be in and out quicker if it’s just the two of us.”
Sam throws down his silverware, and Jess leans over to quiet him down before he can make too big of a scene.
“When are the two of you gonna stop treating me like a child? I can handle this job, just me and Dean!”
“Well Sammy, maybe if you weren’t walking around acting like a little bitch every fucking job you were sent on, then Dad would trust you with this.” Dean said, shoving food into his mouth, not bothering to make eye contact with his little brother. 
“Fuck you Dean.You think that since you’ve got a woman now, and the high table is back to kissing your pretty little ass, that you can say and do whatever the fuck..”
“ENOUGH!” John’s voice boomed, and everyone at the table froze. “Sam, you're not going on this job, and that’s final. It’s dangerous, you’re not experienced enough, that’s it, that’s my call, and that’s final.” 
A defining silence fell over the room. Sam sat there brooding at his plate of food, pushing food around with his fork. Jess dared not say anything, but instead busied herself pouring another glass of wine. Dean continued to give you the cold shoulder, and busied himself with his own food. 
John, on the other hand, was watching Dean and yourself with a sickening smirk on his face. 
“So Y/N. My son and I will be leaving early tomorrow to go on a rather dangerous job.This one is one of the biggest deals that we’ve done in a long time, and if it goes south, it might be awhile before you see Dean again, I assume you plan to send him off properly tonight.”
You turned white as the table cloth sitting on the table in front of you, and Dean paused from eating only a moment, before returning to his meal, a little smoother at hiding his shock than you at his father’s boldness. That or he was just used to it. 
You, on the other hand, had to force down the wave of bile that was working its way up your throat at John’s lewdness. 
“I...I...Don’t see how that’s any of your business.” you stutter, still shocked he boldly asked such a question, much less at the dinner table. 
“Oh, it’s plenty my business princess. See what we have to do tomorrow requires a lot of concentration, and I need my boy’s head in the game, and not on what he did not get last night. See sweetheart, it’s your job to take care of my son, and he’s one of my best, so I expect you to never let him leave this house with his balls….” 
“STOP!” Dean yelled, shocking everyone at the table. Throwing his napkin down he shoves his chair back with force, and goes to walk out of the room, stopping only to look over his shoulder and to call you to him, the first time he’d spoken to you directly in three days.
“Y/N, come, now.” 
Whatever raft Dean had planned when you got back up to your room was better than this conversation, so you quickly got up from the table and followed him there without a word, grateful for an excuse to get away from that room, and away from John.
As soon as you got to your room, you quickly thought maybe you were better off downstairs, because as soon as Dean shut the door and locked it behind you, he rounded on you with more fury than you had ever seen in the green eyes that still haunted your every dream.
“What the fuck was that down there? Do you realize you almost got us both fucked down there?!?! HAVE YOU LOST YOUR FUCKING MIND?! You have the audacity to disrespect my father, at his table, and think he’s not going to make me pay for it?”
Dean backed you to the wall before letting his fist land very close to the side of your face, literally letting you feel the breeze of the blow as he hit the wall with force, pinning you against the wall.
“Dean, how can you say that? You heard what he asked you down there?”
Dean snarled at you, and you cowered back into the wall further.
“He suspects what’s going on between us, or else he wouldn’t ask.You could have played along, but no you had to show your ass. Don’t you get it? He’s dangerous Y/N! One word and he could have you killed, and no one would ever come looking, nothing I could do would stop it!!”
Shoving off the wall and away from you, Dean poured a glass of whiskey in the expensive crystal tumbler that sat on the little table by the door. He took a deep breath to calm himself, before taking it down in one pull. 
When he turned back to you, his eyes were colder than you had ever seen them, and it made your stomach curl sickeningly. 
“How often do I have to apologize to you for this? I know it was my fault. I know I fucked up and pulled you into this mess. I’ve tried to tell you I’m sorry. I’ve tried to show you I’m sorry, everything I’ve done, every job since you got here was to ensure you have a future, to make sure YOU want for nothing!! Night after night, day in and day out, you walk around here mopping, ignoring me, hurting my feelings, disrespect me! This job I’m doing tomorrow is to present you to the high table, to make sure that we can live whatever life there is for us now comfortably, and no one calls a hit out on you!! Do you give a shit? Fuck no!” 
Anger boiled under the surface of your skin like water in a pot, and you had to swallow hard to make your voice work as tears streamed freely down your face. How dare he try and make this all your fault. Like you had disrespected him, when he’d taken everything away from you. 
“I hope your ‘high table’ kills you tomorrow, then maybe I’ll be free of you and your lies.” you spat at him, and he flinches before collecting himself, careful not to let too much show. 
“Oh no baby girl. Because if they kill me, you belong to John Winchester, so you better fucking pray I come back alive.” Dean turns to go into the bathroom connected to your room, undoing his tie with force and throws it across the room.
Turning to face you, his face showed more hurt than he’d let you see before.
“You know, I thought maybe, just maybe I could convince you to feel for me what I’ve felt for you from the moment I saw you. Guess I was wrong.” 
Slamming the door to the bathroom before you could say anything, you stood there with your thoughts reeling. Was he playing with you, or was he telling the truth?
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296 notes · View notes
jawritter · 4 years
Text
When The Lights Go Out
Chapter 6
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: 2203
Series Warnings: Mob level violence, injured Dean, description of injury, creepy Godfather John Winchester, John is pretty much a douche 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: Angst, Fighting, Hurt!Dean, description of injury, blood, swearing, John is a dick, regret. I think that’s it. 
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***
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Sitting in the chair that was facing the window that looked out on the dark lawn below from Dean’s room, you shove the peppermint tea that Jess had brought up to you a little further away. She was just trying to make you better, and you knew that, but you didn’t think there was anything anyone could do to make you feel better. Especially when none of them knew what was really wrong with you. They all thought that you were just nervous about Dean’s job today, but that was so far from the truth.
Dean’s little revelation before he disappeared in the bathroom was the last thing he’d  said to you last night, and when you finally cried yourself to sleep, you were pretty sure he’d just chosen to sleep in the bathroom and not come out to talk to you. 
He was so angry that you were scared to go and try to talk to him, and when you woke up this morning, Dean and John were already long gone. 
A knock on the door and Jess’ entry pulled you from your thoughts as she made her way to sit down on the chair next to you. 
“Hey you. How are you holding up?”
You shook your head and tried to stop the stinging tears that threatened to spill over the surface from falling.
“I’m okay, just stressed.” you lied, pulling your blanket up to your neck like it could hide your shame. If something happened to Dean today, you’d never forgive yourself. He’d done and given so much to keep you safe, and you pretty much told him last night that you hoped he died. God how you wanted to take it all back, do it all different. 
“John and Dean will be just fine. High table meetings are always stressful and dangerous, because the Campbells will be there, and they like to cause problems with John.They still blame him for Dean and Sam’s mom’s death in that house fire, but this isn’t like it’s something they haven’t dealt with before, and by tonight he will be here, safe and sound.”
Swallowing the lump in your throat you nod your head. You hoped with everything in you that she was right, and that they would make it home. You didn't understand all of this stuff, but you knew that if you became John’s you were probably fucked in ever since of the word, if you even lived through the guilt of never giving Dean the chance he deserved. 
You made a promise to yourself, that if he lived through this, and everything worked out okay, you’d give him that chance. Let yourself fall for him like you were doing before you were forced to move in here. Maybe even get to be happy with him.
Jess put a comforting hand on our shoulder and stood from her seat. 
“Sam and I are about to have a Friends marathon in the living area. Want to join us?” she asked, and you forced a smile in return.
“Maybe in a little bit. I think I’m gonna try and take a shower, see if I can scald away some of this stress.” you tell her, and she gives you a warm smile before leaving you to your thoughts. 
Unwrapping yourself from your cocoon of blankets, you wander your way to the bathroom. You didn’t even have time to start the shower, when you heard a blood curdling  scream from the down stairs part of the house. 
Your heart stopped in your chest, and you ran towards the staircase, coming to the landing just in time to see John and Sam hauling a very bloody Dean through the front door, and towards what they called the medical area of the house. 
For just a moment you were rooted in your spot, unable to make your feet move, as absolute horror gripped you.
You don’t even know really what made feet move, but you numbly made your way towards the yelling, not even really paying attention to what they were saying or the man in a suit that ran past you toward him, though you did note that they were calling him Nick.
When you entered the room the horror that greeted you made the bile rise in your throat. 
They had Dean stretched out on a table, his shirt ripped open, blood pouring from his stomach in a way that you couldn’t really even see the injury, but you knew it was bad. Nick circled the table, yelling commands at Sam that you didn’t even hear over the ringing in your ears.
Nick's British accent was cut off by John’s deep voice, bringing you back to your senses.
“Y/N! GET YOUR ASS OVER HERE, AND COMFORT MY SON! KEEP HIM CALM!”
Your attention snapped from the long, deep gash in Dean’s stomach, to the green eyes that were boring into yours. 
Violence isn't something you were accustomed to. You had never seen anyone hurt that bad in real life, but aside from the blood, and the gore of the cut, it was the hurt in his eyes that made your heart shatter. 
He was staring at you, his eyes almost as red as his stomach, the piercing green duller than normal, eyes wet as if he wanted to cry, but wouldn’t allow himself to. 
You staggered a step towards him, and Dean lifted his hand shakily in our direction. That just made it all hurt worse. 
Grabbing his hand in yours, you card your fingers through his hair, keep your eyes locked on his, as Nick and Sam move around behind you, keeping your back to the wound on Dean’s stomach, and focusing on his face, John standing over your shoulder, watching everything closely. 
“Dean, oh my God, I’m so, sorry.” you said in almost a whisper, shock evident in your voice. 
Dean didn’t answer, just gritted his teeth, and closed his eyes against the pain radiating through his body.
“Gonna have to stitch him up here John. He’s not going to make it to a hospital, but it doesn’t look like anything internal was damaged.” Nick said, and John just nodded above you. 
“You...You’re not going to put him to sleep?” you ask as Nick and Sam prepared needles full of brown liquid.
“Can’t do that. He’s lost too much blood, but don’t worry sweetheart, we’re gonna numb him up real good.” Nick said, Jess made her way to the other side of Dean’s head across the table. 
“Nick’s the family doctor of shorts. Everything’s gonna be fine.” she tries to assure you. 
You try and keep the horror and trembling under control. Focusing on Dean’s eyes, you see one large tear roll down his face as Nick and Sam move closer to his wound. His grip tightens on your hand, but he didn’t scream at what surely was the unbearable pain of the needles entering his wound before the numbing medicine could spread. Sam worked at putting an IV in his free arm next to Jess. 
Once the shots were done it seemed like it took them forever to stitch up him, and Dean’s eyes were getting heavy.  Nick assured you it was just the morphine, and not the blood loss. 
“What went wrong out there?” Sam asked, helping Nick wrap his brother’s wound once the stitching was done with thick antibiotic ointments, and gauze 
“Believe it or not, that didn’t happen at the meeting. We stopped to get gas at a station just outside of town, and some of Sammual’s boys jumped him. They weren't all that happy about the high tables approval of Y/N here, and they thought they’d take it out on Dean.”
Sam gritted his teeth and nodded his head. 
“Don’t worry son this isn’t over, they will pay for this.” John assured him, and Jess put her hand on his shoulder to calm him. 
“You on the other hand,” John said, leering at you as Nick finished up Dean’s wound, “clean up my son! Make sure he’s taken care of! He is your responsibility. If something happens to him, I swear to God your next.” 
John left the room his heavy footsteps echoing as Nick and Sam lifted Dean carefully in front of the table they’d been working on him on. Making their way up the stairs, and into your shared room they laid him down carefully on the bed, before Nick hooked up the bags of fluid and a bag of antibiotics to his IV.
Dean barely moved, or acknowledged what they were doing to him, which scared you, but no one else seemed concerned. 
“I’ll be back in four hours to give him another round of Morphine. I’ll go grab some Ambian to help him stay asleep. He needs the rest. Don’t worry sweetheart, he’s going to be just fine.” Nick said, giving you a pat on the back before disappearing to go and get the sleeping aid he’d referred to, returning only long enough to give it to him, and leave. 
Crawling carefully in the bed next to you, you carded your fingers through Dean’s tousled hair, his green eyes fluttering open to look at you. 
“I’m sorry Dean, this is all my fault, and I’ve treated you horribly. I wish I could take it all back.” you tell him, tears falling freely down your face as his hand reaches for you like a scared child that has been hurt, looking for comfort. 
“S’Okay, I shouldn’t have snapped at you last night. This hasn’t been easy for you, I know that. I’m just glad I didn’t die before I got to see you again.” he mumbled, his eyes heavy as he fought against the medication.
Carefully as possible, you slip your arm around his head, pulling him close to you as he loses the battle against consciousness. 
You had a second chance with Dean, and you were determined not to fuck it up this time, this time you would be everything he deserved. 
The sound of your bedroom door opening caught your attention as light flooded the dark room where Dean and yourself were laying. Sam’s overly tall figure slipped inside, and shut the door behind him before making his way to the bed with the small desk chair in tow, sitting it next to his brother's side of the bed, before flopping down in it. 
Dean was not a small man by any means, but next to his “little” brother, he looked so small, especially laying on the bed with his stomach sewn shut, and an IV leading from his arm. 
“Did you finish getting him undressed?” Sam asked, and you suddenly felt stupid. You didn't even think about his slacks and shoes that were still on his feet. 
“Oh God, I didn’t think about that.” You said, ripping the cover off of him as gently as you could, and working to take his shoes off as Sam stood and help you undo his slacks, slipping them down his long bowed legs, leaving him just in his tight, black boxers before the two of you covered him back up, and you settle back down next to him.
“You know, John catches you in here, it's my ass. You heard what he said.” you tell Sam in a hushed whisper, and Sam chuckled darkly. 
“Don’t worry about John. He better not tell me shit about coming to check on my brother.” Sam said darkly, and that for some reason was laced with a promise more lethal than anything John had said downstairs. 
“Why did they do this Sam, why do they hate him so much.” you ask, watching as Dean shifted closer to you in his sleep, unconsciously  seeking comfort from you, even through all the drugs they had him on. 
“Because Samual Cambell is a narcissistic dick who can’t let the past go.” Sam said darkly.
“He still blames your dad for your mom’s death?” you ask, settling Dean’s head back on your shoulder. 
“Yep, that’s some of it. Some of it is  he’s just a heartless dick, who wants to have all the power. He hated my dad even when my mom was alive from what I’m told. I don’t really remember as she died when I was just a baby. I can tell you this, no man in his right mind would put a death order on his own fucking grandson, much less the son of John Winchester. He will pay for this Y/N, I promise you. Just worry about getting Dean better. We will take care of the rest.” Sam said, standing up from his chair, and making his way towards the door, stopping just short of opening it.
“You know, Dean really does love you, I’ve never seen him like this before. I just feel like you needed to hear that.” Sam said, before disappearing into the hallway. 
God, you hoped he was telling the truth, because right now, you were pretty sure you had fallen from him the moment you climbed out of his SUV, and you were too big of a coward to admit it to yourself, until you almost lost him.
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jawritter · 4 years
Text
COMING SOON!!!
When The Lights Go Out
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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
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.
A/N: I have no idea how far this series will go, and I will try and post once a week once I start it. I'm advertising it in advance to give people a chance to get on the tag list. If you want to be added to the tag list let me know!!
(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?)
Beta'd by the amazing @deanwanddamons
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Forever Tags: @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
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jawritter · 4 years
Text
Coming this Sunday!
When The Lights Go Out 
Part 1
Coming at 9 am (Central Standard Time)
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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
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.
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?
A/N: This series is beta’d by @deanwanddamons who honestly I don’t know what I’d do without! Thanks so much hun!!
Tags Below The Cut!!
Forever Tags: @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 @lyarr24 @amandamdiehl 
Series Tags: 
@royal-sunflower​
@roonyxx​
@nihilismworld​
@prettysourabbie​
@rosalynshields​
@flamencodiva​
@woodworthti666​
@stilltoomuchafangirl​
@theoneandonlymelol​
@deanandnegansbitch
@lunaticgurly​
@bxbyizzy
@deangirl93
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holylulusworld · 5 years
Text
How to kill your wife Masterlist
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Summary: When his father makes a deal with his business partner Dean has to agree to an arranged marriage. Hating the thought with every fiber of his body he plans to get rid of you.
Pairing: MobsterDean x Reader
Warnings: angst, mentions of kidnapping/torture/sexual assault (nothing graphic), language, arranged marriage, criminal activities, virgin reader, blood, violence, characters death, comforting, fluff, nightmares, scared reader, tears, possible smut in future chapters, slow burn, plot twist
Part 1 - The contract
Part 2 - The wedding
Part 3 - An empty bed
Part 4 - Playing along
Part 5 - How to kill your wife
Part 6 - The past can still hurt
Part 7 - Confessions
Part 8 - Good Intensions
Part 9 - Loosing it all
Part 10 - Getting your life back
Part 11 - My wife *
Part 12 - How to love your wife
Part 13 - This is our life **
Part 14 - Crime and Punishment
Part 15 - Family Bonds
Part 16 - End of family business
Part 17 - Retirement
Part 18 - Changes **
Part 19 - The family business
Part 20 - An eye for an eye
Part 21 - Our kind of family (Epilogue)
* light smut
** smut
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