Warnings: angst, language, arguments, kinda cheating, smut, protected sex, enemies to lovers, and they were roommates, mentions of cheating/post shitty relationships, implied smut, implied oral sex
Summary: Dean crashes into your life and won’t stop bugging you.
Word Count: 2,2 k
Written/Created for: @spnaubingo
2020 SPN AU BINGO Masterlist
Divider by @firefly-graphics
“Are you fucking serious, psycho?” hands-on your hips you growl at the guy standing in front of your door. “Did you follow me home? I already told you the pie is mine.”
“Wait—what?” the guy cocks his head, looks you up and down before he gets a piece of paper out. “No, no! Not you again. Crazy chick,” he retorts, eyes a little narrowed now. “Did you hurt my girlfriend?”
“Girlfriend? What the fuck are you talking about? I came home,” now you lean in the doorframe, grinning like a winner, “ate a slice of the pie you wanted, and had a shower. I didn’t have the time to kill anyone.”
“This is my girl’s place,” you snatch the piece of paper out of the guy’s hand, frowning when you read your former roommate’s name. “She said I shall pick her up at seven.”
“Dude, that’s my former roommate and she doesn’t live here for like seven or eight weeks. I kicked her bitchy ass out,” handing the guy the piece of paper you snicker. “She liked to do this, ya know. Once in a while a guy came around and left heartbroken. Bitch doesn’t even have the guts to break up with a guy.”
“She wants to break up with me?” the guy sighs now and you pity him for a moment until you remember you hate him. “Fuck, here I am, trying to not be a one and done for once. Great job, Dean.”
“Wait…you are Dean Winchester!” you snicker, eyes roaming his body. “You must be last on her bucket list to fuck!”
“What the fuck!” Dean grunts, stepping closer to look over your shoulder. “Is this a sick game? Do you want to make fun of me, Lisa?”
“Dude, relax,” patting his shoulder you sigh. “Lisa, she had a bucket list of guys she wants to fuck during her time at Stanford. You were the last one,” licking your lips you look Dean all over again. “Don’t know why she broke up with you before you did the nasty.”
“I wanted to wait this time,” Dean hands you a single red rose, shaking his head. “I didn’t even like her that much. It’s just, my brother and his girlfriend called me a heartbreaker, and no one believes I can be faithful.”
“Only as you like to have sex and not commit doesn’t mean you are a bad person!”
“Exactly,” nodding eagerly Dean licks his lips. “I never cheated on a girl. I’m young and want to live my life to the fullest. I do not promise a girl marriage or crap. If you go out with me,” he shamelessly drinks your body in, eyes stopping to your cleavage, “you’ll get dirty soon enough.”
“Ahem,” dipping your head you look past Dean to see your nosy neighbor watch you and the cocky guy. “You better come inside or Mrs. Nosy over there will talk trash about me again.”
“You wanna invite me in, sweetheart,” smirk on his plump lips Dean follows you inside your apartment, eyes immediately drifting toward your ass. “I like the view.”
“Asshole,” you know without looking that Dean was staring at your ass in your sleep shorts. “I wanted to have a nap after studying non-stop. How about coffee?”
“Can I have a slice of the pie too?” he asks, eyes drifting toward your legs when you stop in your tracks to turn around.
“If you answer me one question, you’ll get a slice, Winchester,” he grins, eyes glued to your lips now.
“Shoot me, sweetheart.”
“It’s Y/N and I want to know,” fisting his jacket you look up at Dean, lips pressed into a thin line, “if you fucked my former roommate.”
“Nope,” he purrs, leaning closer to inhale your shampoo. “I told you about my problems.”
“You mean the problems other people have with your lifestyle, Dean,” you pat his cheek before you turn back around to walk toward the kitchen. “I don’t do relationships either.”
“Why? I’m simply curious,” he asks, following you toward the kitchen.
“I like sex, not heartbreak,” you shrug, turning your attention toward the coffee machine. “How do you like it?”
“Rough, wet, a lot of kissing and I love to do it in the kitchen,” you laugh nervously when Dean steps closer to grip your waistline. “Sweetheart, I could show it to you right now.”
“I meant your coffee, Winchester but,” your hands are in his hair seconds later, “give me some sugar first.” He kisses you greedily, forces his tongue into your mouth, making you moan.
“I’m on it,” he picks you up to hold you against the wall, hastily tugging at your top while you try to shove his jacket down his shoulders. “Okay, let me get you out of the top and I’ll show you the goods.”
“Deal.”
Your top and his jacket end up splattered on the floor. You are impatient, just like Dean when you grasp for each other.
“Fuck, Y/N,” he whines when you take the lead, hand down his pants to get his dick out. “I need a condom.”
“The cookie jar with the naughty girl on it,” you grin when Dean looks at the jar with a naked guy. “Yeah, that one is the naughty cookie jar.”
“That’s a guy but fuck it—” while you stand on wobbling legs, Dean fetches a condom to roll it over his length, his pants still on. “You’ve got some naughty stuff in your kitchen, sweetheart.”
Dean grins when he ushers back toward you. His member stands tall and proud, reminds you of your favorite toy. But Dean’s cock looks much better than any toy you ever saw.
“Come here, lover boy-“ you crook your finger to lure Dean in. “Give it to me good.”
“That is the worst quote you could bring up,” either way, Dean grips you roughly, slams your back against the wall, smirking when you wrap your legs around his waist.
“You love it, asshole. Now, how do you like it?” wrapping your arms around his shoulders you smirk. “Come on, fuck me, Dean!”
“I’m on it,” Dean groans against you, fighting to shove your sleep shorts aside. “Fucking with clothes on is difficult.”
“Don’t act all coy now,” you dig your fingertips into his shoulders when he finally slips inside, thrusting forward to fill you in on go. “That’s much better.”
“Yeah?” he laughs against you, ignores you fought over apple pie this morning. “Worth a slice of apple pie?”
“Fuck me and we can talk about your pie,” how he manages to hold you against the wall and move at the pace he sets is a mystery to you. Dean groans with every thrust, loves the slick sound of your coupling fills the kitchen. “Fuck, that’s good.”
“Better than fighting?” he grips your ass, squeezes your flesh roughly while you try to hold tight onto his shoulders. “Damn me, I should’ve taken you right there, in the parking lot of the fucking store.”
“Hmmm…” you dip your head, try anything to capture his plump lips. “You promised a lot of kissing.” panting you try to focus on the man move inside of you, not your ringing phone. “Fuck, call me later.”
“Shit—fuck—sweetheart I need you to cum for me,” if you ever heard a man make an erotic noise it's right at the moment when Dean moans against your lips. “Y/N—”
“D-Dean,” a choked-out moan leaves your lips as your body trembles violently. “I love fucking in clothes.”
“I knew you are a dirty little slut the moment you stole my pie,” Dean speeds up, chases his release while you tug at his hair, and crash your lips onto his mouth to swallow his deep groans. Seconds later Dean comes with a loud grunt, and a violent jerk of his hips.
“That wasn’t bad, Winchester—”
“It was a B, Y/N,” he sighs against you, tongue licking into your mouth. “Sorry, I was on the edge for months. I tried to be a good boy and not fuck on the first date.”
“Well, congrats and thank you for the orgasm,” you tug harder at his hair, grinning when he growls low in his throat. “If you want some pie, I want round two in my bedroom.”
“Already addicted?”
“Maybe…”
“There is nothing better than postcoital pie,” you laugh at Dean’s words, even pat his chest. It’s been a long time since you felt comfortable around a guy. “So, will you tell me why you don’t do relationships?”
“I thought you were about to leave,” you roll to your side, eyes closing for a moment to not watch Dean go.
“I could stay a little longer,” Dean offers. “I like your bed, it’s comfortable and I’m a little tired after round three. Hell, my jaw still hurts.”
“I had two serious relationships,” oddly Dean spoons you to bury his face in your neck. “My first boyfriend and the dude popping my cherry dropped me shortly after we arrived at Stanford. He wanted parties, random girls and I, well I believed in monogamy.”
“A cheater?”
“Nah, he broke up with me before he fucked the first chick. At least he had better manners than my second boyfriend,” you turn around to face Dean. It’s an odd feeling to have him so close.
“I only had one real relationship. Her name was Cassie and she kinda was the one breaking my heart back then. She wasn’t my first girl, but the first I fell in love with.”
“Anyways,” concentrating on the freckles on Dean’s face you try to swallow the lump in your throat, “my second boyfriend, I caught him in the act, on our bed. After that, I decided to never let anyone in again.”
“Sorry,” mumbling the word Dean slides his hand over your hair. “I’m the last guy telling you they were douches. I’m no better.”
“Did you ever cheat?”
“Nope.”
“In that case, you are a better man, Dean,” somehow Dean feels his chest swell at your words. No one ever cared about his side of the story. Everyone believes he’s a heartbreaker, a cheater even.
“WHAT THE FUCK DEAN!” Lisa drops her keys, furiously waving her hands while you whip your head toward her, grinning like the devil.
“Ah, hey, Lis’,” you give her a wink. “As you decided to steal my favorite dress when I asked you to move out and told everyone I kicked you out, I just snatched your boyfriend out of your hands.”
“WAIT—WHAT?” Dean gapes at Lisa, huffing when she throws insults at him. “Uh-you said she wanted to break up with me.”
“Lisa only sent her lovers to my apartment when she wanted to break up with them. She wasn’t here to meet up with you hours ago,” you shrug.
“I gave him the wrong address,” while you move your hand toward Dean’s thigh to grip it tightly Lisa throws a tantrum. “I called!”
“Ah, yeah,” laughing you look at your phone on the ground. “We were kinda busy fucking. Sorry, Lisa. The joke is on you this time.”
“Good thing I wanted to fuck him once and dump him too,” storming out of your bedroom Lisa kicks things out of her way, even smashes a lamp against the wall. “I bet he’s a loser and can’t get it up. I tried to get in his pants for weeks.”
“Yeah about that, he’s a bomb, Lis’!”
“Did you know she didn’t want to dump me?” brows furrowed Dean looks at you.
“No,” covering your eyes with one arm you sigh. “I told you she likes to do this. Anytime she wanted to dump a guy she left the apartment and only came back after I called her. I honestly believed it’s the same with you.”
“She wanted to dump me either way,” rolling onto his back Dean looks at the ceiling. “Guess I am luckless when it comes to relationships and crap.”
“Same, dude—”
“Why are you here again?” looking at the pie in Dean’s hands you eye the gift warily. “Dean, what do you want?”
“You see—” placing the pie onto the kitchen counter Dean sighs deeply. “I know you don’t do relationships, but I think we clicked. I know you must’ve felt it too.”
“I felt orgasms,” you like to play it cool, and not give away you thought about Dean the whole weekend. “Dean, this won’t work out.”
“How can you be sure if you don’t even want to try? I’m not perfect, but I promise to be honest and never cheat on you, Y/N,” shuffling on his feet Dean looks at you. “We could go for a date. If you don’t like me, we can stay friends.”
“Friends with benefits?” sliding your hand over Dean’s chest you look up at him.
“Deal…”
“Okay, the benefits ain’t that bad, Winchester,” this time you barely made it out of your apartment before he had you in the backseat of his car and later at the room he shares with his classmate.
“I heard you are looking for a roommate,” Dean smirks when you look up at him. “Well, we can’t always fuck at my room. The sock over the doorknob doesn’t always work out.”
“You want to move in with me?”
“Yeah, uh—erm,” stammering Dean tries to convince you to let him move in with you. “I mean, we could have sex anytime. I’m a great roommate. My burgers are the best and we can study together.”
“You will pay half of the rent and help me clean too. Only as I let you see me naked doesn’t mean I will treat you differently.”
“Deal, sweetheart…”
“Deal, Mr. Winchester.”
And then, they were roommates…and lovers…and best friends…and much later…they grew old and grey together…
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