Dean Winchester complicates things.
Pairing : Sam x Reader (Love interest), Dean x ofc, Dean x Reader. Word count : 4,004 Written for : @spnaubingo Square filled : Bartender!Sam Warnings : Angst, smut, dirty talk.
A/N : This was inspired by @sorenmarie87 when she wrote “You were frustrated beyond belief with this whole situation. You had warned your older sister repeatedly that she needed to be careful when she was out with her latest boytoy. She screamed at you before storming out of the room.”
SPN AU & Trope Bingo Masterlist.
“Hit me.” Sam chuckled and started to pour another shot. “Don’t skimp on me, Samuel.”
“It’s Sam.” He shook his head, grabbing a second shot glass and filling that too.
“Oh, Jesus Christ, how many is that now?” You groaned when you stepped behind the bar to start your shift and you saw him pouring the second shot.
“This one would be number-”
“Three.” She lied.
“Seven.” He corrected, shooting her a look.
“You just lost your tip.” She pointed a wavering finger at him.
“You never leave one.” He teased her and walked down the bar, letting you deal with her.
“Because you always rat me out to my sister!” She called after him, and he laughed as he stopped in front of another customer, throwing the dishcloth over his shoulder and got a drink order.
“Elizabeth-”
“Don’t do that.” She waved a hand at you before picking up a shot and downing it. “You sound like mom.”
“You think I like that I have to basically mother my older sister?” She shot you a look and picked up the second shot and downed it. You shook your head as two fingers pointed to the empty glasses. “No. I’m cutting you off.”
“It’s barely 9pm.”
“Exactly. And I’d like to not have to pick you up off the floor before 10. Go home, Beth.”
“Samuel-”
“No!” You told her, then turned him and pointed angrily at him.
His hands went up. “Sorry Elizabeth, I’m not getting between you two. Not making that mistake again.” He shook his head.
You grabbed the empty glasses and put them in the sink before walking off to serve a table.
Since you went off to serve someone else and Sam was busy with other customers, she got up, reached over the bar and grabbed a glass stacked by the sink and poured herself a beer from the tap. “You’re too good for this place.” She told him.
“Don’t I know it.” He muttered, moving past to grab whiskey off a shelf, not really looking at her.
“You’re not interested in me, are you?” He laughed. “Yeah.. Wish you had a brother.” She muttered, taking a sip.
“Elizabeth!” You yelled at her, slamming a tray of empties down on the counter. “Did you serve her?” You glared at Sam as he moved past.
“Nope. Must have grabbed it herself.” He put the drinks down, and got the money for them before coming back over towards you and your sister. “And I do.”
“You do what?” You looked at him.
“Have a brother.” Her eyes shot up to him.
“No.” You warned both of them.
“Older?” She asked and he nodded. “Interesting.” She licked her lips and smirked. “As good looking as you?”
“Don’t answer that.” You pushed Sam away, and snatched the beer out of her hand. “Go. Home.”
“But Samuel has a brother for me.” she pouted. You pointed towards the door and she sighed. “Why do I come here?” she muttered and wander off towards the pool tables.
“Don’t you dare.” you shot Sam a look.
“Don’t I dare what?”
“Introduce her to your brother.” you sighed. “You know how she is..”
He laughed. “My brother has a reputation of his own. Besides, she’ll meet him sooner or later.” You cocked an eyebrow. “He’s moving to town in a few weeks.”
“Shit.” the last thing you needed was a strain between you and Sam, and you knew that’s what would happen. It’s what always happened.
Dean Winchester’s reputation hit town before he did, and it kind of shocked you. He sounded so vastly different from how you knew Sam was.
And then you met him. He was charming, cocky, and he knew how good looking he was. But he was sweet too. There was no denying they were related, but there was also a vast contrast between them.
Soon after, he met your sister. Bought her a few drinks, and you didn’t see them for the rest of the night.
Around 4am, not long after getting home, there was a knock on your apartment door. “Hey, can I crash here?”
“Yeah, sure.” you opened the door to let Sam in. “What’s wrong with your place?”
“Dean.” You nodded, remembering Dean was living with him until he got his own place. “And your sister.” Your eyebrows shot up. “In my bed. Can I also use your laptop to find a new mattress so I can burn this one?”
“Yeah.” you winced, shutting the door. “Find me something to burn that mental image out of my brain.”
“Hey, I had to walk in on it.” he grumbled.
“Netflix to distract you so you don’t have nightmares about it?”
“Please.”
Barely half an hour later, Sam looked from the tv in your bedroom, down at you curled up towards him fast asleep. He smiled softly, and reached for the remote. Turning down the volume, he then put it back on the nightstand and got comfortable himself.
It was only a matter of time before the inevitable happened. Only this time, you honestly weren’t sure what that was going to be. She had sworn this time was different. He was different, and she was as well. But you couldn’t help but warn her anyways.
And yet here you were, frustrated beyond belief at the situation. When she had told you what happened, she didn’t even let you open your mouth before she started yelling at you. She was positive you would say ‘I told you so’ and she wasn’t going to give you the chance. So she screamed at you before storming out.
And then you stormed out.
“Where is your brother.” You growled as soon as you were in the bar.
Sam looked up. “I don’t know.. Home, if he’s not with your sister..”
“No, no he’s not with her.” You shook your head. “He was, and then she caught him fucking someone else.” You turned and stormed out.
Sam closed his eyes and sighed. “Come on, Dean…” Sam groaned. This was going to complicate things.
When he heard a pounding on the door, Dean got up. “Hang on, don’t get your panties in a wad.” Opening the door, he cocked an eyebrow. “What can I do for you, Princess.” He smirked.
“What the fuck is wrong with you!” You shoved him, making him stumble back, and you stormed into the apartment.
“Come on in.” He muttered sarcastically, shutting the door. “What’s up your ass? If you’d like it to be me-”
“Why would you do that her?” You turned on him.
“Who?”
“My sister! I get that she isn’t perfect, but fuck, Dean.. she didn’t deserve that.” He rolled his eyes and went for a beer. “Do you even care?” Once he closed the fridge, you pulled the beer out of his hand and slammed it on the counter away from him. “You cheated on her, Dean and you don’t even fucking give a shit how bad you hurt her.”
“I didn’t cheat on her.” He pointed out, looking a little agitated at the accusation.
“No?”
“No.”
“So, you didn’t take my sister out and get caught fucking someone else?”
“No, that did happen..”
“That’s cheating!”
“No.” He shook his head. “Your sister and I were never exclusive. She was never my girlfriend. We didn’t even go on a single date.” He pointed out. “We just drank, and fucked.” He shrugged. “She’s not the kind of girl I date, sweetheart. She’s the kind of girl I call once, maybe twice, if she’s lucky.”
“You’re an asshole.”
“No. Well, maybe.” He shrugged. “But I never told her we were more than we were.” He licked his lips. “It was just sex. Good sex, I’ll give her that. But I hear she’s had almost as much practice as me.” He smirked.
“Ugh.” You got a look of disgust and shoved him away from you. “What do women see in you?”
“Good looks, charming personality.” You scoffed, making him smirk again. “And a dirty filthy mouth that makes promises I can keep.”
You rolled your eyes and turned to walk away. “You’re a piece of shit.”
“The more you talk like that, the harder I get.” He teased coming up behind you. “And dirty talk isn’t all my mouth is good for.” You shivered as his breath fanned out on the back of your neck.
“Fuck you.”
“Anytime, sweetheart. I bet it doesn’t even need to come to that to make you cum.” He chuckled.
“You probably couldn’t even do it then.” You turned your head, defiance burning in your eyes. “You’re obviously overcompensating for something.”
He bit his bottom lip. “I knew I liked you. Let’s make a bet, Hm?” His nose brushed against your neck. “We’re going to go sit down, you and me. My hands are not going to touch you, not unless you asked me to. And I’m going to make you cum.”
“Fat fucking chance.”
“Hey, I had your sister begging in minutes.” He smirked. “If I can make you cum, or make you ask for me to touch you or fuck you, I win. If I get nowhere, you win.”
“I’m pretty sure either way you’re a winner, so why would I agree to this?”
“If you win, I’ll apologize to your sister. I’ll admit I was wrong, I will take her out somewhere nice, and I will treat her like a fucking queen, if she’ll let me.”
“And if you win?”
“You go on a date with me.” He grinned. You shook your head. “Come on, Princess. There’s a fire in you that I want to see more of.” his mouth moved over your neck, making you moan softly. “Good girl.” he took your hand and started leading you towards the couch.
He sat down, and watched you as you stood there awkwardly for a moment.
“Sit.” You went to sit next to him but he stopped you. “Oh no. You’re not sitting there.” He pulled you forward so you were straddling his lap. “Right here.”
“Dean-”
“Ah.” He put a finger to your lips to shush you. “No talking. Only I talk.” He smiled, and his arms stretched over the back of the couch. “Unless you’re going to give in already. I’d be very disappointed if you did.”
“No. I just-”
“Ah.” he shook his head. “Now, let’s see.. What are you into..” He eyed you a bit, eyes lingering on your breasts, and then again between your thighs.
“Worst foreplay ever.” You mumbled, sitting back more on his thighs.
Dean laughed. “You don’t know how bad I want to kiss you right now.” He smiled at you. His eyes shining playfully.
“Mhmm.” You hummed, looking around Sam’s living room as if he couldn’t be any less interesting and chewed on your bottom lip.
“I wanna bite that bottom lip.” Your eyes shifted back to him as let your bottom lip fall from between your teeth. “I wanna feel your tongue against mine. So soft and wet. I bet you wanna feel mine too, don’t you sweetheart? But elsewhere.”
The left corner of his mouth curved up slightly and he watched your throat as you swallowed. You did your best to ignore him, eyes fluttering away again.
“I’d love to taste you.” He shifted slightly, an inch or so lower on the couch, getting comfortable. “Lick up the side of your neck to your ear.” He smirked when your brow twitched. “You’d thought I’d say something else, huh.” He chuckled. “Don’t worry sweetheart, I’ll get there eventually.” You shot him a glare and he grinned. “I want to taste every inch of you.”
“This is getting ridiculous.” You started to get up.
“If you get off my lap I win.”
“That wasn’t-”
“Winner by default because you forfeit.”
“You’re so full of yourself.” You scoffed. “Do you actually think you-”
“I do.” He nodded. “I can practically smell it.”
“You’re a dick.”
“I have one. And I’m damn good with it. Is that what you want to talk about? About how good my hard cock will feel deep inside you? Hm?” He cocked an eyebrow. “Or, and this could be a fun time too.. How about I just rub my cock between those lips, letting your clit feel every fucking vein. How does that sound, princess?” You bit your bottom lip again. “If you want, I’ll cum on your clit, it’ll feel so warm and good. And I’ll rub it in. With my cock or with my fingers, the choice is yours.”
You shifted your hips a bit, and you cursed yourself and him, because you couldn’t even try to hide it. You couldn’t close your legs, you couldn’t just get up and leave. Well, you could, but your pride wasn’t letting you. And yet, your pride was losing here too.
“Come a little closer, baby.” he shifted his hips again. “You can get that little bit of friction you need, and I won’t even count it.” You gave him a suspicious look. “Rules were that I wouldn’t touch you. I never said you couldn’t touch me.”
Your eyes moved down his chest and settled on the bulge in his jeans. You watched as it twitched under the denim, and your eyes went back to meet his. He had been watching you the whole time.
“You’re getting more curious.” He smiled. “Curious what all the fuss is about. I can tell you, if you come a bit closer.”
You couldn’t help yourself, it was almost like autopilot, you shifted just enough to barely feel his bulge against you. You didn’t want to give him the full satisfaction, so you were able to hold back at least that much. But you had a feeling this small victory wouldn’t last. You wanted him to keep talking.
He leaned forward a bit, so his voice was low and right by your ear. “It’s the drag, sweetheart. When I bury my cock as deep as I can and I slowly pull it out, the drag is what pulls you under.” You bit your bottom lip again and closed your eyes. “I can go back in just as slow if you want. Take my time with you, torture you an inch at a time.” You shifted again, thighs opening wider, not realizing you were starting to grind against him. “You like that? You want me to take my time with you? Worship you as if you were the most precious thing on this earth? I’d gladly do that for you, baby. Again and again.”
You let out a shaky breath, pressing a bit harder on him.
“Or, I can fuck you.” He went back against the couch again, eyes locked with yours. “Your feet over my shoulders so I can fuck you deep. I’ll watch those tits bounce with every thrust I give you. Or maybe I’ll have you on your knees, face in the mattress to keep you quiet while I fuck you with everything I’ve got.”
You groaned, and let your forehead rest on his shoulder. You could feel how wet you were getting. Between the promises he made, and you knew damn well they were promises of what was to come if you gave in, and the feel of him hard underneath you, you were barely fighting it.
“Do you want me to cum inside you? Filling you up again and again? Letting you feel how I swell with cum right before I shoot it deep in your cunt? Or do you want me to mark you as mine with it? I’ll cum anywhere you want baby.”
“Dean..” you moaned softly.
“Maybe I will mark you as mine. With my cum, with my fingers and with my teeth.” he gave your earlobe a soft bite.
“Please..” You whimpered.
“Yeah, I think that’s what I’ll do. I’ll fuck you from behind, let my cock hit you deep and hard, make you scream my name, and right before I fill that soaked pussy of yours, I’ll bite you like a fucking animal.”
“Dean, please.” you whined.
“How wet are you right now, baby? You soaking through your panties just thinking about it?” You nodded. “What do you want?”
“Please, stop.” You begged, but you’re heart wasn’t in it.
“Not gonna happen, sweetheart. Not until you either give in, or soak through your jeans and mine. I wanna feel just how fucking wet you are.”
“Shit..” You breath hitched.
“Such a good girl.” He smirked. “You’ve already out last your sister.”
“Don’t.” You warned him and he chuckled.
“Answer me this, and I’ll never mention it again.”
“What?”
“How bad do you want my cock right now?” You groaned, and he chuckled again. “Just say the word and it’s yours.” You shook your head. “So stubborn.” He smiled. “I guess I’ll just keep imagining it, and telling you. Know what I’m thinking right now?” You shook your head again. “I’m thinking about ripping both our clothes off, and you grinding that wet pussy of yours onto my cock right here, like this.” He bit his bottom lip. “And maybe, just maybe, once it’s coated in you, it’ll slide right into your cunt. Mm.” He moaned, his head going back. “I bet you look so fucking good when you ride a cock.”
“Fuck.” You cursed, trying to get more friction.
“I want to bounce you on my cock so fucking bad right now.”
“Dean…”
“I’ll rub your clit while you do it.”
“Dean..” You breathed impatiently.
“Rub your warm wetness into your clit until you cum screaming around my cock.”
“Jesus, Dean just shut the fuck up and fuck me!”
He grinned. “You got it.” He lips pressed to yours hard, his arms wrapping around you, pulling you tighter against him. Your mouth opened to him almost immediately, you were hungry for him. His tongue swept in over yours, his hands moving to rid you of your shirt.
Your lips parted just long enough for him to toss it aside, and in that moment, you saw the calmness in his eyes was long gone. All that was left was hunger. Dean wanted you bad.
You lips met his again, teeth scraping against his lips, and he groaned as he stood, lifting you with him as he started for the bedroom. He kicked the door shut behind him before laying you on the bed. “How do you want it, Princess?”
“I don’t fucking care. Just make me cum.”
“Just remember, you owe me a date after this.” He grinned.
Sam walked in, tossing his keys down. He was so exhausted he left work a few hours early. His night had been spent trying to figure out what the hell he was suppose to do now. This had been why he had moved away from his brother years ago. Dean complicated things. And now he was complicating things here. He realized he’d have to have a talk with Dean about it. Either get his shit together or get lost.
Sam grabbed a beer from the fridge and walked towards the living room. Dean wasn’t there, so he figured his brother had gone out after being yelled at by you. He dropped onto the couch and took a swig.
When he looked down at the bottle in his hand, he noticed a shirt on the floor. His brow furrowed as he nudged it with his foot. He recognized that shirt. Picking up, he took a better look. It had been his, once. Until he gave it to..
Sam looked to his bedroom door. Dread filled him as he got up and slowly moved towards it. Silently opening the door, he felt his stomach drop when he saw you and his brother sleeping naked in his bed. He gently closed the door, and left his apartment.
You had been glad to wake up before Sam got home or Dean woke up, and snuck out of the apartment. You hid away all day, but now it was time to work. With a sigh, you pushed open the bar door and headed into start your shift. “Hey Sam.” You gave him a smile.
Sam didn’t even look up from the drink he was pouring for your sister. Didn’t even acknowledge your presence. But the look on his face told you all you need to know. He knew.
Your mood dropped, drastically. “I’m a fucking idiot.” You mumbled to yourself as you started for the back, barely hearing the door opening behind you.
“Hey princess.” Dean’s arm went around your shoulder. “How we doing today?”
“Peachy.” You muttered, pulling away from him and heading to the back.
Dean furrowed his brow at that, and went for the bar. “What was that about?” He asked as Sam came over. Sam slammed a beer on the bar, and Dean quickly plugged up the neck with his finger when it started to foam over. “What the hell, Sammy?”
“I can’t fucking believe you, Dean.”
“What’d I do?”
“You fucked her.” Sam growled it out. “And you don’t even give a shit about how it might make everyone else feel.” Dean looked down the bar at Elizabeth, and then back at Sammy. “I liked her, Dean. I really fucking liked her.”
“Sammy, I-”
“Yeah, you didn’t know. Just like last time, right?” He shook his head and walked away.
Dean felt like shit. He pulled his finger from the bottle and sat there staring at it. “Fuck.” He got up.
By the time you came out, Dean was gone. There was a full beer and some money on the bar, but he was no where to be seen. “Where’d Dean go?”
“Don’t know, don’t fucking care.” Sam grabbed the money and the beer and moved away.
“Sam-”
“I don’t want to hear it. But maybe your sister might like to hear the apology.”
Your eyes moved to your sister and you saw how hurt she was. “I’m sorry, Beth.” She shook her head and turned away.
Sam didn’t talk to you unless he needed to, at least not until the next night. “Dean staying with you?”
You furrowed your brows. “No, I haven’t heard from him since he left the bar yesterday.. Why?”
“Doesn’t matter.” Sam shook his head and walked away to put chairs up as you two closed up the bar. Despite his words, he told you anyways. “Hasn’t been back to my place, hasn’t answered my calls… Probably just fucked off somewhere else.”
You glanced to Sam’s phone, that he had left on the bar. Taking it in your hand, you unlocked it and searched through his contacts until you found Dean’s. Then you pulled out your phone and dialed, only for his voicemail to pick up after a few rings.
“Hey, you’ve reached Dean-”
“Jerk!” Sam’s voice cut through the message.
“You’re a bitch, Sammy.” And the tone sounded with a beep.
“Hey, Dean.” Sam turned and looked at you. “It’s Y/N. I just..” You sighed. “Come home, Dean. Sam’s worried. And I’m still waiting for that date you promised me.” You smiled softly to yourself, not noticing how Sam watched you. “It’s rude to stand a girl up like this. You’ve got my number now, so call me, okay? I’ll be waiting.” You looked down at your phone as you hung up.
“A date?” You nodded. “He hasn’t taken a girl on a date since Lisa broke his heart.” Sam muttered mostly to himself.
“And it looks like he still isn’t going to.” You put Sam’s phone down and tucked yours back in your pocket.
“Shit.” He muttered, heading for his phone.
“What?” You looked at him confused as he grabbed it and dialed.
“Hey, Dean.. Sammy.” Sam sighed. “Call me back, okay. I guess the three of us need to talk since it looks like I’m not the only Winchester who fell for her.” Your eyes went wide. “You’re still an ass, but you should have just told me.. Come on home. Jerk.”
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