Chapter Text
The loud chatter of patrons and the classic rock blaring from the speakers reached Y/N’s ears, but it didn’t register as she weaved around people, stalking up to the bar as her heels added to the sounds in the room. She let out a frustrated growl, taking off her trench coat and placed it on the hook under the bench, along with her purse. She dropped herself on the bar stool, drumming her fingers on the dark mahogany of the bar as she waited for the bartender to make his way to her.
She was soon met with piercing blue eyes and a soft smile despite the intimidating build. He leaned his hands on the edge of the bar, an eyebrow raised as he waited for her to speak.
“The usual, Benny,” she said, folding her arms on the surface.
“Alright, how was this one?” he asked, as he reached for the bottle of her favorite whiskey and poured a double.
She rolled her eyes as he placed the glass in front of her, picking it up and taking a sip instantly. “Don’t even ask.”
“That bad, huh?” Benny wondered, as he leaned on the bar, his full attention on her now.
“That bad and he knows it,” she groaned, taking another big sip of her drink. “Chewed with his mouth open, talked about the Dodgers the whole time, and he had an unhealthy obsession with his cat.”
Benny snorted but recovered quickly, shaking his head. “Where do you find these guys, Y/N?”
“I don’t,” she scoffed, irritated as she spun the glass around in her hand. “I get set up on these stupid dates by Jo, and honestly I can’t do it anymore.”
“So what now, then?” he asked, glancing behind him as he heard someone enter through the back entrance in the supply room, before turning his attention back to her.
“Now nothing. I’m done with dating,” she replied, firmly.
He frowned, completely confused by her declaration. “Seriously? You’re giving up on dating? You? Miss “always had a date or a boyfriend since high school”?”
She gave him a quick glare before she picked up her drink, taking a sip. “Yes.”
Just as Benny was about to speak, the supply room door opened. Y/N beamed as the man clad in a deep green shirt and dark blue jeans walked the few steps between the room and the bar, opening the small door and stepping in behind it. He picked up a cloth and tossed it over his shoulder, giving Benny a nod as he came over to them.
“What’s going on over here?” he asked, as he smiled over at Y/N. “Hey.”
“Hey,” she smiled, as she sat up a bit straighter, happy to see her best friend. “And you know… just lamenting to my favorite shrink about my love life.”
She turned her head and smiled at Benny, causing him to chuckle to himself. He moved behind Dean as he made his way down the bar, wiping the surface and picking up empty glasses.
“Another C minus?” Dean asked her, smiling knowingly.
“More like F,” she replied, shaking her head as she rolled her eyes. “I mean… All I want is a guy who’s smart, funny, charming, and really good in bed. Why is it so hard to find a guy like that?”
Dean scoffed. “Yeah, we’re a rare breed.”
“So yeah, I’m done with dating,” she continued, not really hearing what Dean had just said. “Now, I’m just going to take a page out of your book and engage in one-night stands. That’s what I need to just… unwind and forget about dating for a while.”
Benny looked at Dean pointedly, gesturing his head towards Y/N as he widened his eyes. Grimacing, Dean shook his head and mouthed “fuck no” before he cleared his throat.
“You better head out, Donna’s probably waiting for you,” Dean said, as he grabbed the glasses from his friend and business partner.
Glancing down at his watch, Benny grimaced. “Ah, damn. You’re right. Alright, I’m going.”
“Tell Donna I said hi,” Y/N called out, leaning her chin in her hand as she rested her elbow against the dark mahogany.
“Will do, cher. You have a good night,” Benny said, as he smiled at her, tapped Dean on the shoulder, and made his way towards the back exit.
“So…” she started as Dean stood in front of her, leaning against the bar in the same way Benny had previously. “Get me good and drunk?”
He chuckled, dropping his head as he shook it. Lifting it up, he looked deep into her eyes. “Absolutely not, sweetheart.”
“Why not?” she asked, frowning.
“Because as your best friend and business owner of this fine establishment, that wouldn’t be right. Especially considering I can guess why you want to,” he replied, turning to face her completely, leaning his folded arms on the bar.
“Really?” She gazed into his green orbs, smiling as she leaned in a little more.
“You just wanna be so buzzed that whoever you hook up with tonight at least feels like a decent lay,” he stated, a knowing smirk on his face.
She rolled her eyes as she leaned back, picking up her drink and throwing it back in one big gulp. “You got me.”
“Well, I’m not about to let that happen, because you deserve better than that, Y/N,” he said, turning his head and nodding at a patron who waved him over. “I’ll be back.”
Her thoughts wondered as he left to help the customer out, staring into the empty glass in her hand. God knew she was trying to find the right guy for herself so that she didn’t go through this cycle anymore, but she was beginning to think it would never happen.
“Hey, Y/N! I didn’t see you come in! How are you?” she heard a female voice ask, and turned to see Pamela move behind her, smiling.
“I’m good, Pamela, and it’s fine. You guys are swamped tonight,” she replied, her eyes following the dark-haired woman as she moved behind the bar with trays in her hands.
“I mean, not unusual for a Friday night but this is a little ridiculous,” Pamela stated, as she looked around at the crowded bar. “But hey, I’m not complainin’. More tips in my hand.”
Y/N smiled at her as she retreated to serving customers, just as Dean returned with a few more glasses and set them aside for the dishwasher.
“Can I at least get another if you won’t let me get drunk?” she asked, holding the glass out to him.
Dean smirked, picking up the bottle of her favorite whiskey and pouring her another double. Placing the bottle down, he watched her as she sipped it, humming to herself. Maybe it was wrong of him to keep her from hooking up if she wanted to, but he was just trying to save himself from any more heartache than he already had over the last 13 years. Time and time again, he found himself trying to tell her how he felt, how crazy about her he was, but every time he got the courage some other guy would come along and sweep Y/N off her feet. He had been there for her when those same guys broke her heart, and maybe he should’ve said something then, but the risk involved in breaking their friendship was too great.
The night wore on, eventually coming to end as Dean sent the last of the bar flies’ home in cabs, and Pamela wished him a good weekend before leaving. Y/N was still there, wanting to leave when he did so that they could at least spend some time together. She helped him unpack the clean glasses from the washer, and set them again, ready for the next night.
“You know…” she trailed off, as she stuck her tongue out while she tried to get the glasses into a perfect line. “Totally sober and very horny aren’t a great combination.”
He nearly choked at her remark, covering it up with a chuckle. “Hey, I just tried to keep you from regretting it in the morning.”
“Which is totally hypocritical, by the way. You’re always hooking up with women,” she stated, glaring at him.
“Yeah, but I’m never that drunk or regretting it in the morning,” he countered, lifting an eyebrow as he glanced at her. “And neither are they.”
She turned to face him as he continued to clear up, shaking her head at him as she saw him smirking. “Yeah, well… I think you need to make it up to me, somehow.”
“Just say the word and I can make it up to you all you want, sweetheart,” he remarked, grinning.
They had always been flirty with each other, and it had always been more genuine from Dean’s side than hers. Y/N blinked a few times, thinking about what he just said. A wicked smile grew on her face as she walked over to him, leaning against the bar, and looking up at him.
“If I’m right about what I think you meant, then it’s not such a bad idea,” she said, biting her lip.
His eyes widened, shocked at what she was implying. That escalated real quick . “Y/N, I was just messin’ around, like we do sometimes.”
She hummed, nodding. “I’m sure but… I think it’s a good idea.”
He shook his head to clear the thoughts that were suddenly flooding it. “No, it’s really not.”
“Oh, come on, what’s the big deal? I’ve heard the stories,” she said, smirking as her gaze wandered down the length of his body. “The great Dean Winchester who can make panties drop with just a smirk and make them scream all night.”
He scoffed, sighing as he placed the glass in his hand down on the bar, turning to her. “So… what? It’s just once and then you’re good?”
He really didn’t want to get himself into something with her, afraid that would only complicate his feelings for her. However, at the same time, he knew if both of them were willing then he wouldn’t be able to resist.
“Yeah,” she shrugged, but squinted as her mind continued to throw out possibilities. “Once… twice… or maybe we make it a regular thing.”
“You mean a ‘friends with benefits’ thing?” he asked, lifting an eyebrow as he looked at her knowingly.
She smiled, sheepishly. “Maybe.”
“Y/N…” he trailed off, sighing heavily as he closed his eyes. “No, it’s not a good idea.”
“Why not?” she asked, scoffing. “We’re both adults here, we can handle this properly.”
“It could get messy, and I’ve already had my fair share of that,” he threw back, shaking his head.
“Dean, listen to me,” she started, placing her hands on his shoulders as their eyes locked on each other. “You’re my best friend, and this would just be you helping me out, that’s all. I haven’t had decent sex in six months, and I know you haven’t been with anyone in a few weeks, so whatever you need from me too, you can ask for it. We keep the rules simple, and nothing gets complicated. We both get to have great sex and still enjoy our friendship.”
Dean huffed as he thought it over, looking away from her so he didn’t get distracted by her beautiful features. He had dreamt of being with this woman since he met her, the first day of a new school year where he was a senior and she was a sophomore. Now an opportunity was staring him in the face to be with her in some capacity, and he was too scared to take it. If he didn’t, then nothing much would change, but if he did… then everything could. He could lose her forever if things got complicated. Or he might get everything he’s ever wanted since he was 17.
Maybe this is what could give him the courage to speak up and finally tell her how much he loved her and always had. Maybe he gave this thing a shot for a couple of weeks, get a chance to see how Y/N felt about him and whether there could be more from her side too, and then everything would work out.
“Alright,” he said, looking back at her with a grin. “You got yourself a deal, sweetheart.”
She beamed, leaning up and kissing his cheek. “Thank you.”
“Hey, don’t thank me yet. That’s for after I make you scream,” he stated, winking at her.
She felt a shiver run down her spine, something that had happened all too often at Dean’s flirtations, considering most of the time they just joked around.
“Okay, let me finish up here, then we can head over to mine.” He placed the glasses in line before taking the crate into the back room.
Once she was out of sight, Dean leaned back against the wall, bumping the crown of his head against it, groaning as he closed his eyes. He couldn’t believe he just agreed to that, but he was hoping that it all worked out in his favor.
He wouldn’t know unless he took a chance.
Dean opened the door to his apartment, letting Y/N in as he took the key out of the lock and closed the door. He took off his jacket and draped it over the chair at the round table in his small kitchen area. Y/N took off her trench coat and dropped it on the couch, turning to him.
“Can I get you anything? Water? Something to eat?” he asked, brushing his palms together, nervously.
“No,” she replied, smiling softly.
He walked over to her, slowly, his mind on overdrive as he thought about what was going to happen soon. “So… we just-”
She moved in closer, pushing herself up on the toes of her heels, pressing her lips to his. Placing her hands on his shoulders, she pressed herself against him as his arms came around her waist. He pulled her close, the kiss deepening as her arms wrapped around his neck. He couldn’t believe he was kissing Y/N, something he didn’t think would ever happen.
“Bedroom,” she whispered against his lips, breathing heavily before kissing him again.
“Wait, um-“ he stopped her, looking her in the eyes. “Shouldn’t we-”
Sensing what he was going to say, she cut him off with a rough kiss. “Can we talk it through after?”
“Uh… okay,” he said, before he quickly pulled her closer, kissing her passionately.
They stumbled through the living area as Dean led them backwards towards his bedroom. Lifting her up slightly, her feet dangled above the floor as he carried her over to the bed. He gently laid her down, standing up to take her and this moment in properly. He couldn’t believe he was really doing this. Shifting on the bed, she got up on her knees and pulled him closer, kissing him sensually as she combed her fingers through his short hair.
“I can’t believe I’m kissing you,” she gasped into kisses, giggling slightly.
It was so strange to her to be doing this, and with her best friend no less, but damn it he was a brilliant kisser. She was glad to know the stories she had overheard from women were true in that regard, and she was certain they would be true about more than kissing.
“Me neither,” he muttered, leaning his forehead against hers as he breathed heavily after the passionate exchange. This was happening, it was really happening, and he could feel his heart beating wildly against his ribcage in anticipation.
“And um, I’m on the pill, so don’t worry,” Y/N added quickly, before her lips pressed against his again.
Y/N’s hands drifted and started tugging at his clothes, her movements frenzied as she pulled off his button up shirt and grasped the black t-shirt under it. He lifted his arms up, allowing her to pull it up and throw it on the floor, her hands roaming his chest as she bit her lip. She had seen him shirtless several times, but this was the first time she felt she was allowed to appreciate it. His hands reached for the zipper on the back of her dress, pulling it down slowly, gulping as his throat suddenly went dry. Inch by inch, her soft skin was revealed to him, her light pink lace bra and panties as he pushed the dress down to her knees. She moved back on the bed, lying flat as he continued to tug the dress down the length of her smooth legs, dropping it on the floor. He took a moment to admire her beauty, his heart soaring at the fact that he was going to be with her in this way, even if it was breaking that it might not be more than that. At least for now.
He climbed onto the bed, hovering over as he leaned in, kissing her softly. His hands moved down to his jeans, making quick work of ridding him of them as she pushed them down and he kicked them off to the ground. She wrapped her legs around him, her covered mound slowly shifting against his crotch, the thin layer of his boxers and her panties the only barrier between them. He groaned as he felt her grind against him, his cock twitching as he felt himself getting harder.
“Holy shit, Dean,” she gasped, as she moved against him.
He ground his hips down against her, causing her to moan loudly. He smirked as his hand moved between their bodies, his fingers running along the lace of her panties, feeling her wetness through the fabric.
“Fuck,” he whispered, hooking his finger into the edge and pulling it to the side, his eyes glancing down at her. “So fucking perfect.”
She hummed as she looked up at him, trying to remain calm as he rubbed his fingers along her folds.
“This okay?” he asked, his voice slightly shaky with nerves.
“Yeah,” she replied, nodding as she smiled.
He slowly pushed his fingers into her heat, his breath hitching as her walls immediately clenched around him. He started to thrust them in and out, looking at her as her eyes closed, a moan escaping her.
“Look at me,” he whispered against her lips.
Her eyes snapped open, her mouth agape as she felt him move his fingers within her, never having felt so much from so little. He relished in the feel of her, unable to really understand how this was happening, his eyes gazing into hers, neither of them looking away.
“So fucking wet, Y/N,” he groaned, leaning in and kissing her, passionately.
Her hands glided down his smooth back, her lip tucking between her teeth as she felt the muscles contract under her touch. Her hand moved under the waistband of his boxers, a soft groan leaving her as she squeezed the flesh of his perky ass.
“God, I need you to fuck me, right now,” she groaned, impatiently.
“Patience, Y/N,” he chuckled, kissing her cheek.
He thrusted his fingers a little faster, causing her to grab onto his back tightly, biting her lip as she moaned.
“Oh, fuck you, Winchester,” she groaned, as she playfully glared at him.
He chuckled, leaning in and kissing her neck, moving down her collarbone to her breasts. His other hand moved down and hooked his thumb into the waistband of his boxers, slowly bringing them down. He pulled his fingers out of her, placing them on her lips. Her gaze never left his as her tongue licked them softly, causing him to groan.
Dean quickly sat up on his knees, kicking his boxers off to the floor as he moved over Y/N. She glanced down, feeling her mouth practically salivate at the sight of his hard cock. She had found herself wondering several times what he was working with below the belt, and it was incredible. She shifted around on the mattress as she tugged her panties down, kicking them off her foot. Dean swallowed nervously as he looked her up and down, wondering once again if this was a good idea. Things were about to change. He just hoped it was for the better. She wrapped her legs around his waist again, holding onto his shoulders as he lined himself to her entrance.
“Dean, please,” she begged, squirming under him.
Looking into her eyes, he slowly entered her, his shaft sheathed by her walls. He took a moment to bask in the feel of her around him, realizing how long he had imagined this happening between them, and it was finally coming true. It doesn’t mean anything to her , but he chose to push that thought out of his head.
“Oh god, wow,” she gasped, feeling him buried completely within her. He was bigger than she thought, and she was glad he gave her a moment to adjust.
He pulled back slightly before he moved in, his hips thrusting into hers as he set a moderate pace. He leaned down, kissing her roughly, groaning as he slid deeper into her.
He pulled away from the kiss, pressing his forehead to hers. “Oh fuck, sweetheart, you feel so damn good.”
“So do you,” she moaned, combing her fingers through his hair. “Oh, fuck, Dean… fuck me faster, please.”
He picked up speed, holding himself up on his hands as he pounded into her. She cried out as his cock moved within her, hitting her g-spot perfectly with each thrust. She threw her head back against the mattress, a string of moans and curses leaving her as she pulled closer, her heels pressing into his ass.
“Oh, fuck, yes!” she yelled, gripping his hair tight. “God, Dean… you feel so fucking good inside me.”
His head drifted lower, pulling the cup of her bra down with his teeth, lightly nipping at the flesh. His tongue circled the hardened bud, driving her wild with lust.
“Shit, so good,” she moaned, wantonly, holding his head to make sure he didn’t move.
He continued to move within her, the head of his cock hitting that sweet spot inside so well, plus several others she never knew she had. Her walls clenched around him, a groan leaving him as he felt his cock throb. This was a moment he always dreamt of, and no matter what the circumstances were, he was going to revel in it.
“Can feel how close you are, Y/N,” he growled, lifting his head and looking deep into her eyes. “You gonna cum for me, sweetheart?”
Somehow his voice got deeper during sex, and she found that ridiculously hot. She whimpered, nodding frantically, gripping his hair tighter. He groaned at the pull, but enjoyed the sting of it.
“Yeah, gonna cum,” she cried.
His hand moved down between their bodies, his fingers running over her clit in tight circles. She held onto him, leaning up and kissing him, roughly. It was heated and passionate, and everything he ever wanted with her.
“Oh god, I’m close,” she moaned, biting into her lip. “Dean… make me cum, please, please.”
He groaned as he felt himself getting closer, his hips stuttering as his pace faltered. She could feel the coil within her ready to snap, her walls clenching tighter around his cock.
“Cum with me, Y/N,” he grunted, his neck straining as he held on.
“Oh, fuck,” she gasped. Her hands slapped against his back, nails digging into his skin as she gripped him tight. “Oh fuck, Dean! Fuck, fuck, fuck!”
“Fuck, Y/N,” he groaned, jaw clenching.
The coil in her belly snapped, her walls contracting around his shaft as her slick covered him. He pounded into her a few more times before he threw his head back, the muscles in his neck tight as he groaned, spilling his seed inside her.
Dean pulled out of her, rolling off onto his bed, staring up at the ceiling. He breathed heavily, hearing Y/N breathing at the same harsh pace. He wiped his brow, feeling the sweat wet his fingers as his eyes didn’t leave the small crack in the plaster. He just had sex with Y/N. Amazing, mind blowing sex. He wanted nothing more than to roll over to her, kiss her senseless and ask her to be with him forever, but he knew that would never happen.
“Fuck, that was really good,” she breathed, giggling softly.
“Yeah,” he agreed, turning his head to look at her. “You okay?”
“I’m great,” she replied, beaming at him. “Thank you, I really needed that.”
He nodded, trying to play it as cool as he could manage in that moment. “No need to thank, sweetheart. Always happy to help out a friend.”
“Well, I’m very glad you did,” she stated, tapping his shoulder before she sat up.
Dean pushed himself up on his elbows, watching as she adjusted her bra back into place and slipped her panties back on. She got dressed, zipping up the dress halfway, not bothering with the rest as she would put her trench coat on.
“You sure you can’t stay? We can hang out, watch a movie,” he suggested, hoping desperately that she would take the offer.
“It’s past 2am, Dean, I gotta get home. Charlie’s probably wondering where I am,” she said, putting her heels on.
“Okay,” he mumbled, nodding.
“Don’t walk me out, I’ll pull the door shut,” she informed, coming over to him and kissing his cheek, softly. “Let’s find some time to talk about this, okay?”
“Yeah, sure thing,” he muttered, only managing a half smirk.
“You okay?” she asked, frowning as she cupped his face in her hand.
She could always sense when something was wrong with him, and she wondered why he looked so lost in that moment. He wished he could tell her what was wrong, but right now wasn’t the time for that. He needed to wait a little longer.
“I’m fine, Y/N,” he finally said, smirking at her. “Now, get yourself home safe, okay?”
She smiled, lightly brushing her thumb against his cheek. “I’ll text you when I do.”
“Goodnight, sweetheart,” he whispered, looking up at her.
“Goodnight,” she whispered back, kissing his cheek again.
He watched her walk out of his bedroom, her heels clicking against the floorboards as she made her way to the front door. He heard it open and close, a frustrated groan leaving him as he threw himself back on the bed. That had been the most incredible thing to ever happen to him, and he couldn’t even do more about it. He couldn’t tell her how he felt, in fear that he may ruin everything and scare her away. Maybe it was a stupid decision to get involved in something like this. He had one night stands and flings before, even a few relationships that lasted a little longer than that, but never a friends with benefits situation. He certainly didn’t think it would be his best friend since high school that he would have it with.
As he stared up at the ceiling, he thought about how it had only been one night and he could still put a stop to it, if he wanted to. However, the realization sunk in that now that he had felt Y/N like this, he couldn’t let her go. She meant so much to him, and he couldn’t turn back now. He had to stick it out.
And maybe, along the way… Y/N would realize he meant more to her too.