A/N: Hey guys so the time is finally here to unveil my newest and favorite fic I’ve ever written!!! This fic is my baby and I’ve been working on it and on off for the past 6 months and last month I finally found a good, comfortable pace and rhythm that helps to make this fic be so unique and stand out compared to others. Obviously I’ve written smutty and emotional fics before but this 1 really takes the cake for me. It’s way more descriptive than past writing and I know I’ve poured a lot myself and my own personal experiences into this and feel like it really helps shape the story and these characters. I was also torn about splitting it up into 2 parts but I don’t leaving myself or others hanging and knew that if I did that, it never would’ve been completed so forewarning now it’s pretty long (oh darn woah is you having more material to read); in fact, it’s the longest fic I’ve written so I’d hope it turn out well. Anywho enough rambling for me, I’m so excited to share this with you guys and hope you enjoy it!!! Also please feel free to give me feedback and send me requests and prompts!!! Love you all and get ready for this!!! :D
Here’s the prompt:
Sam convinces all of you to go out drinking despite always butting heads with Dean and the next morning you wake up in his bed, much to the dismay of both of you…
You slammed the car door shut as you begrudgingly grabbed your duffel bag from the backseat after finishing up a hunt in Boise. What was supposed to be a simple salt and burn turned into a giant brawl between you and the eldest Winchester, Dean. You both have been known to butt heads constantly so hunting together was always lively to say the least, according to Sam and Cas anyway. These past 3 years with the Winchesters have been some of the best and worst of your life. While working a case in your hometown, you had discovered they were also trying to work the same exact case. Despite your many attempts at telling them to back the hell off as this was your town and your turf and that you preferred working alone, their stubbornness knew no bounds and you decided instead of banishing them, you could put their assistance to good use, having no choice but to let them tag along. They had found you grieving on top of your dead husband’s vessel in a pool of his blood after discovering he was possessed by a demon for some time and during the exorcism, he forced your husband to kill himself before escaping his vessel and at that point you knew that it was too late and he was a lost cause. The loss was too much to bear and while Dean was skeptical of the idea of adding another member to Team Free Will, he couldn’t help but empathize with your situation and was tired of Sam gripping at him about it so they offered you a spot on their hunting team and a room in the Bunker which was a pretty sweet gig, for the most part. Ever since that day, you vowed to extract your revenge on anything that went bump in the night so no 1 else would suffer like you have and you made a promise to yourself that you would never fall in love again, which lead you here.
“Could you be anymore bitchy,” Dean strongly emphasized as he sighed in annoyance. You blantly stared at him. If that’s how he wanted to play today, 2 can play it that game.
You forced a fake smile on your face as you waltzed over to him, “Oh I’m sorry, I didn’t realize I had to take your feelings into account,” you stressed, “And could you be anymore of a douche,” you poked his chest roughly with your finger.
He grabbed you by your wrist, “Y/N I’m not in the fucking mood for this shit right now,” he sighed as he retrieved his bag from the trunk flinging it over his shoulder lazily while Sam was retrieving his stuff from the front seat, already preparing to tune you both out as he could see where this was going.
“Yea well you think I was in the god damn mood while we were taking out that ghost,” you spat back at him.
“Hey now! If I hadn’t gotten there and pushed you aside when I did you would’ve been good as dead,” he countered back.
“I was doing just fine until you fucking showed up and started this god damn shit show,” you rebuttled snarkly as you grabbed your jacket sitting in the back seat.
“Well excuse me for trying to do my god damn job right,” he growled back at her as he slammed the trunk shut.
“Your job,” you enunciated harshly while walking towards the bunker, “Was supposed to be helping Sam take care of those bones but somebody was pissed they didn’t get to be a part of the action so instead they decided to break the fucking rules and jeopardize this case!”
“Jeopardize this case,” Dean laughed mockingly while following after you, “Oh sweetheart if you consider me saving your life jeopardizing a case then you clearly have another thing coming and Sam and I warned you about needing back up from the get go but you wanted to charge in alone all blades and glory.”
“Sounds like someone else I know,” you glared back at him as you stood outside the front door knowing that this argument had taken off. You never meant to put yourself in the middle of these situations but god Dean just needs a good punch in the face, especially for shit like this, “Look Dean I had it under control!”
“Letting a ghost almost possess and kill you is what you call under control,” Dean barked in disbelief, “If you really had it under control you would’ve seen the damn thing creeping up a mile away!”
You exhaled angrily as you turned back to face him with your hands on your hips, “Listen here Winchester I was born and raised into this profession just like you and have all the training and experience in the world to back me up so dealing with a salt and burn is a fucking cake walk for me.”
“If it was such a cake walk then how did you make such a rookie mistake,” Dean hollered at you honestly not believing how ridiculous you sounded but you shrugged it off because you felt the same about him right now.
“Okay Dean; please, enlighten me on what my so called mistake was this time,” you growled at him having just about enough as you pointed at Sam, “Sam trusts my judgement and hasn’t said a damn thing about this or any hunting matter so go on tell me what this and all these other so called past mistakes are that are affecting me hunting with you!”
“Yea Sammy hasn’t said anything because he knows I’m god damn right! Not everything is about you Y/N,” Dean roared back at her, “And as much as we fight we should be working as a god damn team so whenever I come in and fucking help save your sorry ass a fucking thank you would be nice!”
“Oh I’ll give you a fucking thanks,” you hissed as you grabbed Dean by his shirt collar getting ready to strike.
“Enough!” You and Dean both look over to see an absolutely infuriated Sam, which was a very rare occurrence, as he stomped over towards the both of you, “I’m so sick and tired of you guys fighting; I mean seriously, can we go 1 hunt without this?! Just 1 is all I’m asking! You guys have been arguing over literally nothing for 3 years straight! 3 of the longest years of my life and that says a lot because I’ve been trapped in the cage with Lucifer and Michael and lost my soul,” you let go of Dean quickly as you both instantly felt the guilt creep in.
“Sam,” you sighed feeling extremely horrible for putting him through this time and time again. Him and Dean, even though you didn’t want to admit it, have done more for you these past few years then anyone ever has in your entire life and had it not been for both of them you wouldn’t even be here. Dean didn’t look any better. He always hated seeing his little brother upset, especially if he was the cause. His whole life he’s looked out for and protected Sam and still does so to this day which is something you kind of admire about him. Despite your problems with each other, you never meant to take your aggressions out on Sam, at any point.
“I love you both so damn much but I’m not going to choose between you and am done being in the middle of whatever this is,” Sam confessed as he unlocked the door to the bunker stomping inside.
You and Dean sluggishly trailed behind him watching him storm down the hall, “I’m going to be in my room unpacking and binge watching the rest of Stranger Things. If you need me for anything besides being a mediator let me know,” he walked into his room slamming the door shut slightly. You and Dean had stood in the hallway awkwardly for a few minutes still reveling in how pissed off Sam is at you guys. You both decided that it was best to go to your own quarters for a bit for some much needed destress and relaxation time hoping it would break some of the tension.
Hours have passed and you had managed to unpack your stuff, shower, and now were catching up on your reading until your stomach spoke for you. You realized you hadn’t eaten much today and decided to get a quick snack as you walked out of your room and into the kitchen with your book in hand, only to discover Sam on his laptop.
He looked up to see you and smiled, “Hey.” “Hey,” you greeted awkwardly as you rubbed the back of your neck nervously awaiting what was to come. “Look I’m really sorry about snapping on you and Dean earlier,” he apologized, “I lost my cool and made the situation way worse than it should’ve been.”
“What the hell are you talking about,” you asked in him complete and utter disbelief, “We’re the ones who should be apologizing to you.”
“Y/N,” he started before you sat down next to him at the table making sure your page was marked as you quickly closed your book.
“Don’t Y/N me right now, you’re right,” you confessed whole heartedly, “We’ve put you in the middle of every disagreement we’ve ever had and it’s not fair to anyone, especially you. You’re Dean’s not so little brother and my best friend and making you feel like you have to choose between us is totally selfish, inconsiderate, and unrealistic. I don’t know why Dean and I fight as much as we do; I mean, they’re all are so petty, immature, and moronic,” you commented as Sam chuckled lightly, “But I promise we won’t do it anymore, at least around you anyway. Do you forgive me Bullwinkle,” you smiled calling him his nickname. When you had 1st heard Crowley call them Moose and Squirrel, you howled in laughter because it was so befitting and decided after that to give them your own original nicknames along those lines, hence Sam was Bullwinkle and Dean was Rocky.
Sam sighed over dramatically as he pulled you in for a hug, “I guess. Even though you tie me up far too much to my liking Natasha.”
“Yea those poor train tracks,” you giggled against him swatting lightly at him as Dean walked into the kitchen sluggishly letting out a big yawn. You both looked at him, “Good evening Sleeping Beauty,” Sam joked as you chuckled lightly.
“Yea yea,” Dean sighed as he immediately went to the fridge grabbing himself a beer and joined them at the table, “Look Sammy I…about earlier…” “No worries man,” Sam accepted already knowing what his brother was going to say as you leaned back in your chair letting them have their moment before Sam cleared his throat, “So I don’t know about you guys but that last hunt really took a hit on me and I know we’ve been gone all week but I was thinking…”
“You thinking? What else is new,” you replied sarcastically as Dean chuckled softly.
Sam shot her a quick look before continuing, “I was thinking that it’s been awhile since all 3 of us have hung out together, outside of hunts, and thought bar hopping would be a nice change of scenery.”
Dean raised his eyebrows at him, “Woah, woah, woah are you actually implying that we go out for a night of drinking?”
Sam sighed as he ran his hands through his hair, “Look if you guys don’t wanna go we don’t have to,” he closed his laptop shut abruptly, “Forget I said anything.”
“Are you kidding,” you asked honestly kind of surprised that Sam is the one suggesting this kind of thing. Normally Dean is the one who organizes events like this but with how rough everything has been lately from dealing with Lucifer’s return and hunting down his nephilim offspring to searching for Cas, a break from it all definitely sounds nice, at least for tonight anyway, “I’m living for this! Sam Winchester organizing a bar outing and not a research session?”
Dean couldn’t help but agree with you and laughed whole heartedly, “Yea who are you and what have you done with my nerdy, little brother?”
“Just a guy wanting a night out for a change. Like the good old days before heaven and hell,” Sam sassed back at them as you and Dean looked at him suspiciously.
“Sure it’s not because someone hasn’t gotten a good lay in awhile,” Dean teased patting the back of his shoulder lightly as you busted up laughing while Sam flipped him off.
“Well regardless of whatever the reason is,” you interrupted them between giggles, “You know I’m always down to drink so count me in,” Sam grinned as you both eyed Dean awaiting his answer.
“Alright you got me,” Dean caved, “Since we’re heading out I might as well finish this off,” he smirked as he nursed the rest of his beer.
“Yea just let me get a quick shower in and then I’ll be ready to go,” Sam stated as he made his way to his bathroom.
“I think I’ll freshen up a bit too before we leave,” you smiled getting excited at the fact that you guys were actually going out and doing something other than ganking monsters and demons for a change.
“Huh that’s new,” Dean muttered quietly thinking you didn’t hear him. Seriously? After everything that’s happened today, he’s wanting to set you off? Again?
“What’s that supposed to mean,” your voice hinted with annoyance as you eyed him suspiciously.
“You never freshen up to go the bar,” Dean stated very matter of factly, “You’ve never exactly been one in touch with your feminine side Y/N…” You stared at him completely appalled. Oh it’s fucking on. It’s one thing to insult your hunting skills but now your physical appearance? Normally you wouldn’t let something so ridiculous like this bother you but you wanted to give Dean a taste of his own medicine and since you’re having a night out on the town with them it’s the perfect excuse; plus, let’s face it, it’s been far too long since you’ve gotten a good lay yourself.
“Oh I’ll show you feminine,” you angrily marched back into your room grabbing all the supplies you needed. You knew you didn’t have a lot of time to spare so you decided to curl your hair and for your makeup since you knew your skin was always so clear you opted out of foundation and powder and decided to highlight your eyes by doing a quick smokey eye look and put on a little lipstick and gloss on your lips. You walked over to your closet and spotted your little black dress. It’s been years since you’ve worn it; in fact, the last guy who saw you in it was… well, besides the point. If you weren’t running short on time you would’ve hesitated more but you knew Sam and Dean were waiting on you. You quickly put it on and a pair of black pump heels which you knew would cause issues later on but fuck it you’re doing anyway to prove a point to Dean. You grabbed your leather jacket and eyed yourself in the mirror. You looked hot as hell. You smirked as you heard Dean call out your name telling you to hurry up so they could leave already.
“Coming,” you yelled back as you left your room. You made it to the kitchen and as Sam and Dean saw you their jaws dropped. They’d never really seen you dressed up before up until now. Even on cases where you were supposed to, you always avoided it all at costs.
“Damn Y/N,” Sam smiled, “You look amazing.” Oh Sam, always the sweet one.
“Thanks,” you giggled as you did a little spun, “I decided to dress up a bit. Kind of hoping to get a good lay myself.” You looked over at Dean and he honestly looked like he could barely keep it together. His hands fisted at his sides, his eyes were all over you roaming up and down your physique and if he hadn’t made the circumstances so insulting beforehand maybe you’d be flattered but you had to prove your point.
“Well let’s go while the night is still young,” Sam declared as Dean hesitated grabbing his keys out of his pocket.
You smirked strutting over to him and whispered in his ear quiet enough so Sam couldn’t hear, “How’s this for feminine?” You heard him groan quietly as you giggled getting into the impala and heading off for a night of crazy shenanigans.
You arrived at the bar, Sam and Dean immediately finding a booth and settling in it while you grabbed drinks for everyone. You rushed back over with beers in tow with a big grin on your face as you sat down with them. You raised your bottle up in the air, “To saving people and hunting things!” The boys grinned as they raised their bottles up to yours, “To saving people and hunting things,” they repeated after you as you all toasted clinking beer bottles…
You heard a ringing noise echo the room as you groaned softly. What the fuck was that god damn noise destroying your ear drums? You sighed in relief as it stopped and you buried your face into the soft, fluffy like cloud that you were resting your head on. Everything was dark and you wanted it to stay that way. Then that damn noise was back and you moved your arm around blindly and recklessly trying to stop whatever was making that god awful noise. You heard something fall and decided to let the light in. You opened your eyes slowly but surely and groaned at the brightness and the fact that everything was spinning. You covered your eyes with your hand, only for a second, before removing it later and blinking a few times before sitting yourself up against the headboard coming to your surroundings. You were in a room, that much you could gather; shockingly enough, but it definitely wasn’t yours. You looked around: vinyl album covers and different weapons decorated the dark walls, a bookshelf with a few books and pictures, and whatever bed you were laying on right now felt like a dream and you didn’t want to get up. You saw your discarded phone on the ground, not broken; thank god, as well as what looked like yours and someone else’s clothes scattered on a rug. You looked on the nightstand next to you and picked up the picture sitting on top of it. A woman and a little boy. Both looked so happy and carefree you couldn’t help but smile before staring at it more closely. Why did they look so familiar to you? You heard something rustling behind you as you looked down and almost screamed at the sight before you. A guy but not just any guy. It was the guy. The last guy that you would ever expect to wake up to like this; yet alone, want to want to wake up to like this.
“Well good morning to you too sweetheart…”
No. God no. Hell no. Fuck no. This had to be a dream. A really awful dream. You needed to wake up. You pinched yourself and winced only to discover that this, is in fact, real. You and Dean fucking Winchester both naked as jaybirds waking up in the same god damn bed after a night at a bar drinking. How you never noticed him nestled up against you so intimately until now was beyond you. It isn’t hard to put two and two together as you covered your face in your hands seriously not believing your luck. Out of all the guys in the world, it just had to be him. It’s like karma bitch slapped you across the face and the universe was laughing at you. You were dreading this so much already and knew that it was only a matter of time before you had to face reality so that’s exactly what you did. “Dean,” you slowly let his name roll off your tongue as you turned to face him.
You suddenly recognized now that this was his room which meant you were at home in the Bunker, thank god, because you could’ve ended up in worse places with even worse people. He honestly looked pretty rough for wear just as you were sure you did as well and while you were noticing all the bad ways, you couldn’t help but notice the pleasantly good ways as well. Even though you’ve seen him shirtless on countless occasion’s, whether it be patching him up or bumping into him after he gets out of the shower, this was an entirely different circumstance. You noticed his chest was pressed against your back and how it was chiseled enough so he looked built but also had some flab that showed he wasn’t a perfect, greek Adonis either. His arms were burly and strong and you couldn’t help but notice how ripped they looked when wrapped around your waist. Those hazel green eyes always so bright and inviting, anyone could get lost in them and his gaze, especially now. His light brown hair was slightly disheveled from bed head or maybe sex hair you were kind of dying to know or at least run your fingers through it to see how soft it is. Those scars. You could see countless permanently residing on his body. Just one of the many prices you and others in your field of work have to pay and while others would be appalled by them, you knew that each of them told a story. Stories you wanted to hear, know, and learn more about. Your eyes trailed down further seeing his happy trail leading to whatever was underneath those thin, grey sheets leaving little to the imagination as you felt something long and hard poking against your upper thigh. You couldn’t stop these thoughts that were entering your head. Why him? Why like this? Why now? Of all the times…
“Dean what the hell,” you hissed trying everything in your power to ignore his ‘not so little’ problem even though it was prodding near your most sensitive area while Dean moved away from you slightly giving you some space.
“It’s morning,” his voice replied still thick with sleep as you groaned rubbing your thighs together to try and stop whatever witchcraft he’s putting on you.
Dean noticed you struggling to keep your eyes on anything that wasn’t him, “You like what you see,” he smirked back at her waggling his eyebrows. And there’s that damn smirk again. Always so condescendingly arrogant and smug. Whenever he did it to you before, it made you just to punch him in the fucking face but seeing it at this given time was different because now all you wanted to do was fucking punch him in his beautiful face. Lets be serious, there’s a lot things you want to do to that beautiful face and there’s a lot things you want that beautiful face to do to you. Everything about him at this very moment was infuriating and honestly you found it kind of hot. A guy like him? You would fuck him into-god what was wrong with you?! All these thoughts and feelings suddenly surfacing in your mind? You’ve got to snap out of it!
“What happened last night,” you asked quickly trying to change the subject which was proving to be very difficult since said subject and you are sharing the same bed, “All I remember was toasting at the bar and then bam I’m here.”
Dean sighed flipping over so he was laying on his back while running a hand through his messy hair, “Your guess is honestly as good as mine.”
You watched his chest rise and fall in synchronized time and exhaled expecting as much, “Great,” you gathered the bed sheets holding them up around your slightly bare chest, “Like this could get any worse.”
“Hey Dean have you seen Y/N anywhere? She said she made it home last night with some guy who looked extremely dilfy but she wasn’t in her room when I…”
You stand corrected. It just got fucking worse.
Sam walked in his big bro’s room without a care in the god damn world until discovering the both of you, in bed, unclothed, together. His jaw hit the floor before he quickly composed himself and busted up laughing hysterically on sight, “Oh my Chuck!”
You couldn’t help the blush that raised to your cheeks as Dean seemed to be sporting the same look while Sam couldn’t stop his giggle fit, “You and you,” he pointed to you and his brother over dramatically.
“Yea yea Sammy laugh it up,” Dean sighed annoyingly at him while he continued cackling at the both of you. You crossed your arms over your slightly exposed chest. This was it. This topped up to the most utterly humiliating moment of your entire life and all you could do was sit there and take it while the youngest Winchester soaked up this glorious opportunity.
“Guess I have to take back what I said about you being the mature one,” you pouted at him while Sam snickered, “I’m sorry; really, but when you both told me you were bringing someone home last night, the last thing I expected was!”
“We know,” you and Dean cut him off abruptly at the same time sounding unamused.
You both looked back at each other before feeling your face heat up more and quickly turned away from each other while Sam was grinning ear to ear as he started to leave the room, “Well I guess I’ll leave you two lovebirds alone to your lovemaking, I’ve had my fill!”
“Seriously,” Dean called out to him exasperatingly before Sam quickly turned back around grabbing his phone and snapping a quick picture of the two of you.
“Oh my god get out,” you yelled out in frustration as you grabbed one of Dean’s pillows and chucked it at him hard hearing a soft “fuck” from him as he slammed the bedroom door shut knowing you’ve won the battle…for now.
Once you both knew he was gone for good you groaned hiding your face in Dean’s pillow, “Chuck this is so fucking embarrassing,” you muffled out.
“Yea don’t remind me,” Dean sighed as he grabbed some tylenol and his water bottle from his nightstand. He tapped your bare shoulder with his finger, offering you some first. This was new. You sat up and quickly took the medicine from him, putting them in your mouth, and took a swig of water to wash them down while muttering a quiet thank you as Dean nodded doing the same for himself. You couldn’t stop yourself from watching him chug the water seeing his adam’s apple move in his throat. His lips enclosed around the mouth of the water bottle wishing those lips were somewhere else right now. You immediately felt a familiar warmth in your core and you bit your bottom lip trying to hold back the moan in the back of your throat.
Dean wasn’t fairing any better himself. He’s had far too many naked women in his bed over the years but you’re on an entirely different rating scale. Everything about you screamed sexy: from your tousled hair he wanted to run his fingers through and tug extra hard, to your plump, supple lips that were begging to be kissed with each sound that escaped your mouth, your eyes that always seemed to spark passion to his eternal flame every time he gazed into them, your soft, enlarged breasts that he wanted to kneed and squeeze in his large hands, your hips that never seem to lie every time they swayed back and forth and thunder thighs he wanted to tease mercilessly, that ass that was just begging to be smacked every time it jiggled and those legs that seemed miles long, especially in that dress last night.
God that dress, where could he begin? Ever since seeing you in it, he couldn’t shake the images inside his head or stop his mind from wandering. He honestly never expected you to go through with it but he also knew you were never one to turn down a challenge. He’s fully aware that you find dressing up in such a fashion to not only be highly impractical but also uncomfortable as you preferred sporting comfy, casual clothing which he didn’t mind either; in fact, that’s when he found you the most attractive, beautiful even. While yes you constantly fight and belittle each other, Dean realized that through it all there’s no one else he’d rather end up like this with or just end up with period than you.
He noticed you biting your bottom lip and he couldn’t stop himself from scooting closer towards you, “Y/N…” The way he was slowly gravitating himself towards you and how his eyes remained locked with yours. You honestly couldn’t help but follow his lead as you scooted closer to him until you both were laying next to each other in the middle of his bed. You could practically feel the sexual tension in the air and it was only a matter of time before one of you broke it. You couldn’t advert your eyes from trailing down to seeing him gently nibbling on his bottom lip.
“Fuck it,” you muttered under your breath as your lips hungrily attacked his. Dean groaned against your lips as he kissed you back with as much desperation and fever. Before you knew it, all the long, forgotten memories from last night flooded your mind: plenty of shared beers, tequila shots (surprise surprise), you and Dean out on the dance floor bumping and grinding against each other, making out in the bar’s unisex bathroom, Dean suggesting to get out of here, leaving the bar with Sam rideless, Dean pressing you up against Baby and making out again in the abandoned bar parking lot, what felt like the longest drive back home as you teased him relentlessly to the point where his knuckles were turning white from gripping the steering wheel so hard in hopes of controlling himself till you were back at the bunker, and Dean parking Baby into the garage and immediately taking you right there on the spot. In and outside of Baby, on the kitchen counter, in the interrogation room, the library, you lost track of how many times this man fucked you and from what you can remember he was damn good at it too; yet, here you both are, ready to go at it again like a bunch of horny teenagers who can’t keep their hands off each other.
Dean nibbled on your bottom lip and as you moaned softly opening your mouth slightly which he took advantage of as he slide his tongue inside your mouth. Your tongues battling for dominance as he moved himself on top of you so he was hovering over you and you could feel his very obvious erection pressed up against your stomach. You moaned while tugging at his hair and he growled rather loudly immediately digging his nails into your shoulders.
“Oh my god,” you broke your kiss looking at him mischievously as you tested your theory tugging at his locks again, “Do you have a kink,” you couldn’t stop the shit eater’s grin that spread across your face as Dean’s cheeks flushed a light shade of pink.
“Shut up,” Dean muttered awkwardly while you smiled gently running your fingers through his tresses as he relaxed into your touch.
“Wow who would’ve guessed the almighty man whore Dean Winchester has a hair pulling kink,” you giggled as he sighed nervously running his hand through his hair, “Don’t worry I don’t kiss and tell.”
“Good,” he nodded as he let his eyes wander down to your exposed chest and experimentally squeezed one of your breasts. Before you could let out another moan, his mouth was already tugging at your nipple as he squeezed your other breast roughly in his hand. You groaned as he continued his ministrations rotating between the pair: nipping, sucking, and squeezing your breasts making you writhe and squirm underneath his touch. He released your nipple with a pop as you pressed soft kisses along his pulse point and gently nipped at his collarbone. He released a sigh resting his hands on your hips as you let your hands slide up and down his chest and you gazed up at him, his eyes hooded with lust just like yours.
“Are we really doing this,” you asked curiously as your hands snaked around his neck.
“Only if you want to,” he looked to her for confirmation and you couldn’t help but nod dumbly at him as he grinned, “Then get ready because we’re about to get down and dirty.”
You snort laughed at his lame attempt at a pick up line, “Oh you know I’m always down and dirty,” you smirked as you rolled your hips against his and he groaned, “Especially for you Deano.” He pulled you in for another lip lock as you melted into the kiss. There were many things that you were learning about Dean during this little hook up. The man was way too good with his lips and hands. Every kiss and touch worshipped your body and left you begging for more. The way his lips molded perfectly against yours. He tasted like whiskey with a hint of tobacco which you never pegged him for smoking but it honestly didn’t shock you. His hands felt so rough against your skin and were slightly cold sending shivers up your spine every time he placed them on you. He was releasing this inner desire in you that you never even knew you had or could ever feel again but it was Dean. He’s always had this kind of effect on women but here he was with you instead of some of other hussy making you feel kind of special. Despite how much you guys fought, you knew deep down that it was to alleviate the brewing sexual tension and possible feelings you harbored for one another. His hands snaked down your waist until he reached your heated core. You shuddered as his fingers barely grazed you.
“God damn Y/N you’re soaking wet,” his voice was hush as his fingers were coated in your juices and you chewed on your bottom lip watching him in complete and utter fascination awaiting what he would do next, “If I knew that you were this wet for me I would’ve done something way sooner. Like this,” he smirked as he brought his fingers up to his lips as he licked his fingers clean and all you could do was gawk. This was down right the most erotic thing you’ve ever witnessed in your entire life. You didn’t even have any time to react as he snuck underneath the covers grabbing a hold of your upper thighs pulling you closer towards his face. You gasped as you felt his tongue trace along your inner folds. He pulled the sheet up so you could see his face and gazed up you.
“Don’t forget to tell and show me what you like darlin.” There he was sporting that damn grin again and god if there’s anything you could appreciate about Dean at this moment, was that he always wanted to make every experience the best possible. He striked you as the kind of guy that got off at others satisfaction and needed constant reassurance and praise and fuck were you not going to be the one to give it to him, especially based off his handiwork so far. He pulled the covers back over him continued teasing you with his mouth and fingers as your moans began echoing the room getting louder and higher pitched with each movement. He shoved his tongue deeper inside eating you out while his thumb gently rubbed your clit and you instantly began seeing stars. You arched your back and shoved your hips closer against his face while roughly tugging at his hair urging him to keep going and he did such that. You were panting heavily while fisting the bed sheets tightly. You pouted as you felt him pulling away before he inserted his fingers deep inside you. You mewled at him as your hands gripped onto his shoulders as he slide his fingers and out of you at a relatively quick pace and then he found your g spot and fuck you lost it. You were so fucking close and you could feel it boiling deep inside you.
“Y/N,” Dean murmured against you huskily as you quickly aimed your gaze down towards him. Seeing his face against your heat so intimately was turning you on so god damn much. Your cheeks were flushed bright red and were breathing erratically awaiting your orgasm and he could tell just how close you really were and it gave him immediate satisfaction, “Let go darlin. For me,” he pleaded and that was all it fucking took as you cried out to him to a final time as you rode through your release while Dean made sure to get every last drop.
He grinned pulling the covers up again as he slid back up towards you, “Are you an angel because I must have taken your breath away,” he chuckled while you exhaled, “No but Cas is,” you smirked as he frowned instantly and you couldn’t stop the light laughter that escaped your throat. Dean smiled at you as you were trying to catch your breath before bringing him in for another heated kiss. Tasting yourself against his lips was definitely weird to say the least but also surprisingly arousing. He grinned against your lips while pulling the both of you up so he was sitting on the edge of his bed and you were straddled in his lap. You rolled your hips against him yet again reveling in the feeling of his hard erection rubbing against your clit and you both let a low moan. You grinned kissing and nipping all the way down his body sinking lower and lower until you were planted on the floor down on your knees looking like a woman praying at church.
“Well isn’t this a pretty picture,” Dean smirked down at you as you scoffed softly before taking hold of his member in your hand and experimentally stroked it. Dean groaned loudly throwing his head back slightly as you purred at his delicious reaction to your touch.
“You’re not the only one who’s good at going down on someone ya know,” you purred as you pumped his dick a few times before taking him in your mouth and Dean nearly lost it then and there. He growled deeply while harshly tugging at your hair and you bite back a gasp. Your head bobbed up and down while sliding his girth in and out of your mouth. Dean could only marvel at you as your lips wrapped around the head of his dick. He threw his head back and let out the most erotic sigh you’ve ever heard in your entire life and you could already feel the heat pool between your legs again. You continued your ministrations as he let out low groans grasping the bed sheets. His breathing became ragid and you smiled knowing he was close and as much as you wanted to show off your deep throating talents that was just going to have to wait because you wanted the main show to start already. You released his dick with a pop and you heard his annoyed exasperation.
You stood up with a smirk on your face, “Don’t think we’re done yet Winchester,” you purred as you pushed him on the bed to where he was laying down and you crawled on top of him. All he could do was gawk and marvel and stare up at you. Dean figured you would always be a pretty good lay and he can’t say he hasn’t thought about it before but so far it’s exceeded his expectations and he hasn’t gotten to the best part yet. He’s slept with countless woman over the course of his life and while he knew some where equally, if not better skilled than you, there was something he was feeling with you that he hasn’t really felt for any other woman he’s conquered: love. Only one other woman earned that spot before you but he had to experience it and her in order to truly experience you which he definitely planned on doing after this was all through but until then…
“Dean,” your sultry voice as well as you slowly rubbing the tip of his cock around your already wet entrance awoke him from his day dreaming. He choked back a moan as he gazed up at you. You were biting your lower lip and your eyes were practically screaming seduction as he let his hands rest on your hips.
“I want you to fuck me,” your normally soft spoken voice was now laced with desire and full of demand, “Fuck me Dean Winchester. Fuck me into the mattress. Fuck me until I can’t walk or talk straight. Fuck me,” you tried finishing your train of thought before Dean had decided he had enough and flipped you over on your back roughly as he decided to give you what you wanted by thrusting his dick inside you. You nearly lost it right there on the spot as he quickly grabbed your legs placing them over his shoulders.
“Oh I’ll fuck you alright. I’ll fuck you until we can’t hunt anymore,” he whispered huskily into your ear before he slammed his cock deeper inside you. You moaned louder while gripping the headboard for support as he continued to fuck you hard and fast. With each thrust your moans got louder and higher pitched until Dean had you screaming.
“Oh Dean,” you cried out to him and there was his smug little smirk repaying a visit onto his face. He continued his movements while he grunted out to you,
“That’s right Y/N. Scream my name baby, for all of heaven and hell to hear.” Something inside you snapped as you flipped him over so he was on his back this time.
“Now it’s my turn,” you lowered yourself back onto him and he groaned at the contact while watching you ride him. He made a quick grab for your tits groping them in his hands. “Fuck,” you hissed while continuing your pace and soon enough you were back to the state you were in a few seconds ago. Dean smirked up at you as he rubbed your clit with his thumb and you mewled lightly clawing at his chest. He growled almost anomalistically as he flipped you onto your back again. You weren’t finding this to your liking however and decided to flip him back over. Dean obviously not a fan of this either fought back and soon it became a battle of dominance. Who would reign victorious for control?
“Y/N I swear to chuck,” he barked at her before pinning her down by securing her wrists above her head and trapping her by grounding his hips against her own, “Do you want to come or not?”
“Maybe,” you teased and he let out a low, almost primal growl which made you freeze in place. If there was anything sexy about Dean you had to say it was when he lost his temper. He always so domineering and rough but not in an abusive or aggressive way. It was in a way that you knew he wouldn’t take shit from anyone and that he meant business.
“Get on all fours. Now,” he ordered as you quickly obeyed his command positioning yourself on all fours so you were facing the headboard. He got behind you instantly, “Dean what are you going to,” you stopped mid sentence feeling his hand slap hard against your ass cheek. You couldn’t stop the deep groan that escaped your throat. Before you could even prepare yourself, he spanked you again and again until you couldn’t take it anymore.
“Daddy,” you let the word slip off your tongue. Dean stopped mid spank as his eyes widened in shock. He honestly never pegged you to be into the kink but seeing you bent over for him on his bed and his hand print etched on your ass cheek it definitely did something to him.
“Say it again,” his eyes twinkled as he flipped you onto your back roughly and you squeaked in surprise.
“Dean,” you breathed his name while your face flushed slightly at his reaction to discovering your secret kink. “That’s not it,” he smirked as he hovered you.
“Daddy,” you whispered as he growled and slid his cock deep inside you and you choked back a loud moan. You were both back where you started as he slammed in and out of you at a rough and vigorous pace. You were clawing at his back with each thrust while he was leaving love marks all over you. Soon you felt yourself slipping and Dean wasn’t fairing any better himself. Your bodies were flush pressed against each other and the air around you was primal with need.
“Who’s your daddy Y/N,” Dean grunted at you as his cock was hitting your g spot over and over and at that moment all your self control was lost.
“Oh chuck you, you are,” you moaned loudly as you aggressively tugged at his hair and he groaned before gripping your forearms tightly and continued his ministrations. You could feel yourself on the edge as you began chanting his name like it was a fucking prayer.
Dean was mesmerized, seeing you like this all because of him and he could feel himself push past the breaking point, “Scream for me Y/N. Scream for so Sam, Cas, hell even Crowley to hear,” he muttered huskily in your ear as he lifted your leg up propping it on his shoulder as he thrusted harder, “Let them all hear that you’re mine.” The sounds of his gravely voice commanding you, skin slapping together, and the bed rocking back and forth was all out took as you cried out his name one final time before feeling your release and seeing stars. Dean grunted as he did a few more lazy thrusts and dug his nails into your hips before releasing his seed deep inside you.
Both of you panting heavily riding out your highs as your bodies were glistening in a thin layer of sweat. Dean sighed deeply as he removed your leg from resting on his shoulder and quickly pulled out while collapsing next to you.
“Holy shit,” Dean exhaled breathily as you giggled lightly snuggling into his chest. Dean gasped at your nice gesture before wrapping his arm around your waist pulling your closer to his chest. You smiled relaxing into his embrace. You could definitely get used to this.
You both sat in an awkward silence for a few minutes before Dean decided to speak up, “Y/N…”
“Yea,” you looked up at him before he sighed slowly running his hand through his hair, “What’s up,” you asked curiously as he eyed you anxiously. You’ve never seen him look so nervous like this and it was making you feel weary too.
“I want to give this a shot,” he spoke hesitantly while you eyed him in confusion.
“Give what a shot,” you asked while Dean sighed turning towards you. “Us.” You stared at him skeptically, “What about us?”
“Y/N,” he started, “You can’t seriously deny this unspoken thing between us.” You looked at him questioningly, “Unspoken thing?”
“Yea,” he interrupted quickly, “I’ve felt it since we first met. Seeing you mourn over your husband after the exorcism, You were so vulnerable and defeated. I’ve never felt more compelled to someone in my entire life and wanted nothing more than to be there and help you through it because losing loved one’s in our line of business never gets easier.”
All you could do was listen. You felt obliged to hear him and the rest of his crazy but relatable theory out, “Dean…”
“Ya know I actually felt like we got along in the beginning. I don’t know what happened along the way but we just started arguing which was all fine and dandy, until it became more frequent and self destructive. It kind of hurt, not knowing why this was happening so suddenly but despite it all, I still wanted you here and to be around you, which was and still is confusing to me,” he knew he was starting to ramble but he had to get this out. He had to tell you.
You gulped nervously, already seeing the direction this conversation’s has taken as Dean continued, “Maybe it’s just me; I don’t know, but I think we act like we hate each other and fight so much because deep down we know we have feelings for one another…I know I do.”
You were definitely shocked to say the least and honestly couldn’t believe what you just heard yet alone witnessed. While it was very a subtle attempt at a love confession, it was still a love confession nonetheless that was very much Dean: honest, meaningful, and real. It’s the most open you’ve ever seen him. Like he said about you previously, he looked so vulnerable and you could practically see his heart on his sleeve because he had feelings for you and you alone. He knew the risks and complications with romance in the hunting profession yet here he was putting himself on the line all for you. It made you feel very special in a way that no other man has made you feel before, including your deceased husband. Despite all the conflict and turmoil that crossed your path, everything always felt easier with Dean, better even. You had honestly never thought about this before, yet alone the idea of you and Dean up until this point but now that’s out and in the open…
“I mean I feel like we have something great here and there’s nothing I want more than to go through life with you,” he blatantly confessed his eyes glistened slightly.
“Dean I,” you started as you felt tears welling up. No man has ever gone this above and beyond for you and made you feel the way Dean’s made you feel. He was right, you fell for him. You fell for him and wanted to grow with him and love him with every fiber of your being.
“Y/N it’s okay,” he quickly cut you off looking completely and utterly defeated while his gaze shifted downwards away from you, “Don’t worry I’m used to this. If you want we can just act like this never happened and go back to hating each other agai-,” you stopped his train of thought by pressing your lips against his in a short but sweet lip lock.
Dean’s eyes widened as you pulled away slowly, “You’re right,” you hesitated softly, “About the unspoken thing and as for us, I’d like to give us a shot too, If you still want me,” you professed tears falling down your face as Dean pulled you to him and kissed you passionately. You smiled into the kiss as he pulled away wiping away the tears that stained your face.
“I’m sorry for making you cry,” he apologized as you scoffed in disbelief. Only Dean would apologize for something so mediocre. “It’s okay,” you giggled as you leaned into his touch, “They’re happy tears and I’ve needed a good cry like this for years now so thank you. Also I wasn’t expecting you to be such a diehard romantic.”
“You caught me,” he chuckled sticking his tongue out at you while wrapping his arms around your waist, “Let anyone in on my Humphrey Boggart, casanova exterior and you’re dead to me.” You laughed whole heartedly while snuggling into his embrace,
“Don’t worry you secret life and our chick flick moment is safe with me.” You both remained in bed making up for what felt like lost time and for the first time in your life, you truly felt…