Summary: You are in trouble and need fast cash. For the longest time you tried to be a good girl, now you need to break the rules all over again.
Pairing: Mobster!Dean Winchester x Thief!Reader
Warnings: angst, language, breaking and entering, criminal reader, mafia au, implied sexual harassment (not Dean), threats, scared reader, kind of hostage situation, Dean is not a soft mobster here
“You can do this,” you whisper to yourself. “You’ll go inside, get all their shiny things and money, and get out again.” Your fingers are trembling when you try to get the lockpick out of your pocket. “Shit, it’s been too long since I broke into a house.”
Your landlord’s words still echo in your mind. He will kick you out if you don’t get him the money you owe him or give him something sweeter. You shudder at the image, not wanting to end up on your knees in front of your bastard of a landlord.
Summary: You are in trouble and need fast cash. For the longest time you tried to be a good girl, now you need to break the rules all over again.
Pairing: Mobster!Dean Winchester x Thief!Reader
Warnings: angst, language, breaking and entering, criminal reader, mafia au, implied sexual harassment (not Dean), threats, scared reader, kind of hostage situation, Dean is not a soft mobster here
“You can do this,” you whisper to yourself. “You’ll go inside, get all their shiny things and money, and get out again.” Your fingers are trembling when you try to get the lockpick out of your pocket. “Shit, it’s been too long since I broke into a house.”
Your landlord’s words still echo in your mind. He will kick you out if you don’t get him the money you owe him or give him something sweeter. You shudder at the image, not wanting to end up on your knees in front of your bastard of a landlord.
If only you didn’t lose your job and got into that accident costing you your car.
“Fucking great. Back to square one, I guess,” you take a glance over your shoulder to make sure no one is watching you.
One of your former partners told you about an easy target. He only wants forty percent, that greedy bastard.
“Just have a little faith in yourself,” you whisper to yourself, to tame your racing heart. “For fuck’s sake. You once were one of the best cat burglars, Y/N. Get a hold of yourself and do this. I don’t want to suck that asshole’s dick.”
You take a deep breath and close your eyes for a moment to remember the smart and talented thief you once were.
Before you gave up life as a criminal and tried to become one of these normal people working from nine to five. “I can do this…”
Your fingers work on their own. It’s like your body remembers every movement and every trick to unlock the door in the back of the large mansion. You unlock it within a few seconds and slip through the small gap you create as you shove the door open. “Not that bad,” you silently close the door and take another deep gulp of air.
Silence welcomes you to someone else’s home. You feel guilty for breaking into their house. It’s been years since you did something like that, and it feels wrong for the first time in your life.
Years ago, you didn’t give a shit about other people. Your father was a hardass gangster, killing people without batting an eyelash. Your brother, well he was one of the best burglars you ever heard about.
None of them is still alive. Life in your line of business is dangerous and deadly. There is no honor amount gangsters or thieves anymore.
Now you’ve got no other choice than to fall back into old patterns and steal to survive. You are on your own since you turned eighteen and no one is there to catch your fall.
It’s not the time to overthink things. You do this now, or you’ll end up on the street, nothing more than the clothes you are wearing in your possession.
For a moment you stand in the hallway of the stranger’s home and drink the atmosphere in.
A cold shiver runs down your spine as you tiptoe toward the first door. You put your trembling hand onto the door handle and take a deep breath. “This is not your first rodeo, girl. Just get it over with.”
You open the door, hoping to find money, jewelry, or anything worth the fear holding you in a tight grip. The small flashlight in your hands doesn’t help you at all when your eyes land on a gun aimed at your head.
“Hello, there,” a deep voice purrs in your ear and the next thing you feel is a gun pressed to your temple and a strong arm wrapped around your waistline. “I couldn’t believe it when he told me someone is stupid enough to try to break into my house.”
“I—” fuck, you are trembling in fear. Your knees buckle and you don’t know if you are still breathing as the man holding you in a tight grip unlocks his gun. “I-I didn’t want to…please.”
“Sammy, leave us alone,” the man pressing his gun to your head orders. “Give our little rat what he deserves. He got me a nice little rat myself. Hmm…” he runs the gun down your face, pressing it to your cheek. “What do you say, sweetheart. Will you be a good girl and sit over there on the armchair without making a fuss?”
“Y-es,” you can barely choke the word out before you find yourself pushed toward the armchair. You catch your fall, grunting as the man slaps the back of your head. “Ouch.”
“Sit, or I swear I will hurt you so much more,” you sit on the armchair, hugging your legs as you look at the man aiming the gun at you again. “What do you want here? What were you looking for?”
“Money, or jewelry,” whispering the words you dare not to look at the man for much longer. You drop your gaze, praying he will not kill you. “I’m sorry.”
“Money?” the man laughs now, somewhat relieved. “You came here to steal my wallet and shit, sweetheart?” He steps closer to lift your chin with his gun. “You’ll answer my questions and look at me.”
“I needed money and my old partner told me about an easy job. He said no one will be here and that you have enough money to make sure I don’t have to give my landlord a blow job,” you wince as the man secures his gun.
“You’re not lying,” he frowns deeply as tears run down your face. You are shaking in fear now, afraid the man you wanted to steal from will end your life tonight. “Who told you that no one will be here tonight?”
“I-he,” you bite your tongue. If you die tonight, you won’t die as a traitor. “I can’t tell you. You’ll hurt him too.”
“I didn’t hurt you yet,” you shudder as the man roughly grips your chin to look you all over. “None of my men hurt you. Now, tell me everything about this man sending you here.”
“I worked with him once or twice a few years ago. I was out of this life for almost five years. He was the only one offering his help,” he places his gun on the coffee table next to him. “He’s a good man.”
“I hate to break it for you, sweetheart,” you hate that your life is in the stranger’s hands now, “but your old partner ratted you out. I got a call before you even arrived at my house. I think that guy wanted to get rid of you.”
“He would never—” staring at the gun on the table you swallow thickly. Maybe the stranger is right. You haven’t heard of Cole in years. He was the only one answering your call, though. “Why would Cole do such a thing? What does he get out of this?”
“Cole Trenton always tried to get a foot in the door. He wants to become one of my men,” your eyes glued to the gun on the table you simply nod. “I guess he thought you are a nice pawn. I must say, you are cuter than the last guy trying to steal from me.”
“What happened to the last guy?” fuck, you don’t recognize your voice. You sound small and weak, like a scared little mouse.
“Do you really want to know?” you shake your head; afraid you will end just like the other guy. “What’s your name?”
“Do you always want to know the name of your victims?” he chuckles when you finally lift your head to meet his piercing green eyes. “Y/N.”
“Nice name for a greedy little girl like you,” you make a face as it seems that he tries to make fun of you. “How about this. You tell me everything about that guy wanting you to blow him off and we will see if you survive this night…”
“A sandwich,” you wonder aloud as the man steps back inside the room he brought you to. He handcuffed your left wrist to a chair to make sure you don’t try to run. “What is going on?”
“I want you to eat and just listen,” he places the plate in front of you, giving you a stern look. “No talking, just listening.”
“Okay,” taking the offered sandwich you try not to wolf it down. Even though you are scared to hell and back, your stomach screams for food.
“Benny made sure to check on your apartment,” he opens the handcuffs around your wrist, smirking when you pull away. “Your landlord was a hard piece of work. That son of a bitch didn’t want to hand out your belongings.”
“I—you stole my stuff?” he smirks now, as you struggle to not choke on your food. “Why?”
“While you preferred to pass out on me, I made a few calls and got to know you were a talented thief. I’m always looking for new talents. My name is Dean Winchester by the way,” your heart drops as you recognize the name. Dean Winchester is one of the most dangerous mafia bosses in the whole US. “I asked my men to get your belongings.”
“What do you want from me?” Dean cups the back of your neck to easily dominate you. He stares down at you, still that dark smirk on his face.
“You will work for me from now on. If I need a thief, or someone picking a lock for me, you’ll come with me. For now, you will stay in this room and be a good girl. If not,” he squeezes your neck, making you wince, “you don’t want to know what happens then…”
“Dean, why didn’t you kill the girl?” Sam groans as his brother’s thumbs through your file, the one he got from Jody Mills. One of many cops working for Dean. “Dean!?”
“She’s a talent, Sammy,” Dean looks up from the file to face his brother. “I don’t like it when you doubt my decisions. She will pay for breaking into my house. Period.”
“Your job starts on Monday,” Dean points at the box on the bed. “You will only talk to me. You will not leave my house. You will not have your own life until you paid for putting your hands onto what belongs to me.”
“I didn’t touch anything,” you cry. Your lips tremble and you feel hot tears run down your cheeks again. “Please.”
“Oh, sweetheart,” he coos softly as he leans closer to lick the tears off of your cheek, “you are pretty when you cry. Be a good girl, do as you’re told, and you will not be on the receiving end of my wrath…unlike Cole Trenton…”
Signed. Sealed. Delivered. Your life belongs to Dean Winchester now. You don’t know if what’s worse. Death or being Dean Winchester’s chewing toy…
