== Dean meets one of his most challenging hunts yet.
++Dean x Reader
**Request! I hope this is what you had in mind, I had fun writing it :)**
It’s a little different since I kind of focused it from Dean’s point of view.
“Dean? You’ve been holding that beer bottle for five minutes. Did you even hear anything I just said?” Sam’s voice broke through Dean’s trance. Dean started, shaking himself a bit as he looked at his hand.
“Oh,” Dean chuckled, taking a swig of his beer. The bottle was close to empty, and the liquid was room temperature. He grimaced as he set the bottle down. “Gonna have to get another one…” Dean went back to staring over Sam’s shoulder.
Sam squinted his eyes as he studied his brother for a moment. he finished off his own beer and decided to get another round. When he came back, Dean was in the same position as he left him. Sam followed Dean’s gaze and was awestruck. There was a gorgeous woman at the pool table, playing a round with a few men.
“Rack ‘em up, boys!” She hollered, chalking up the end of her pool stick. “Get ready to pay for losing another game!” She smiled.
“Hm….” Dean hummed like a love struck schoolboy. He rested his chin in his hand.
Sam stared at his brother quizzically. “Uh, Dean? You’re not acting like yourself.” Dean hummed again in response, and Sam shook his head. “This is insane,” he mumbled.
“I think I feel like some pool, Sammy,” Dean spoke a few awkward minutes later and stood up, adjusting his jacket and taking a gulp of his beer. He set it back down and walked toward the pool table.
“Yeah, good luck with that one,” Sam said sarcastically as he glanced at the woman again.
“Got room for one more?” Dean spoke directly to the woman as he gathered the pool balls.
She leaned on her pool stick, a devilish grin forming on her lips. “Well, sure, how much are you willing to pay?”
“Well, a girl as pretty as you? I’d pay you without even playing the game.” Shit. Idiot!
The woman scoffed, “I ain’t in that kind of business.” She leaned over the table to take her turn. “If that was an attempt at a pick-up line, I imagine it’ll be entertaining to watch you lose this round.” She looked up at Dean through her eyelashes, trailing her hand up the shaft of the pool stick, then striking the ball to break. Balls went everywhere, and three stripes made it in the pockets. The other men groaned, knowing they would lose again and most of them forfeited.
“I’m- I’m sorry, I didn’t mean for it to come out so creepy,” Dean could feel his ears turn red and he rubbed the back of his neck awkwardly.
“Don’t worry about it Winchester, I heard you were the flirtatious one of the two…” The woman smiled, sticking her hand out to shake Dean’s “The name’s (Y/n).”
Dean shook (Y/n)’s hand, looking confused. “You know who I am?”
She looked at the other guys before leaning in toward Dean, whispering in his ear, “The business you’re in? I’ve heard a thing or two.”
“So… are you-?”
“Sure am, one of the best. Besides you, of course.” She winked. “Although I haven’t experienced you… first-hand. Your turn, Deanie-boy.”
Dean’s jeans started to feel a little snug. Ugh. Damn it. He shifted and cleared his throat. He took his turn, failing miserably, and (Y/n) laughed. “Did you even try, Dean? Hope you got a couple twenties to throw away.”
A couple beers and games later, Dean’s wallet was empty. “I’m gonna have to pass…” Dean mumbled, putting his wallet away.
(Y/n) folded up the stack of bills and put them in her pocket. “That’s okay, this place is gonna close soon, anyway.”
“Well, I’d offer to buy you a final drink, (Y/n), but you took all of my money.” Dean laughed. “I have beer at the motel though, if you wanna go there for a while?“
(Y/n) walked over to Dean, placing a hand on his chest. Fuck. Keep yourself together, man.
"I would,” (Y/n)’s breath softly his Dean’s skin, “But drinking in motel rooms with fuckable men usually gets me in trouble.” She slid her hand down his jacket and slipped a finger in his belt loop, smiling sweetly.
A soft moan slipped out of Dean’s throat. Dammit, I’ve gotta have her. I thought I knew what torture was, but this… “Who said I was trouble?” he choked out a laugh.
(Y/n) leaned closer, her lips close to brushing his, “I’m not worried about you being trouble.” She tugged his belt loop and let go, turning toward the front door. “Nice to meet you, Dean. It was a pleasure winning your money.” She looked back at him, smiling mischievously as she patted her back pocket.
Dean’s eyes watched her ass as she walked out. He stood there for a few moments, trying to process what just happened.
“I see you didn’t get lucky this time,” Sam laughed when he saw his brother walk through the motel door. Sam had gone back to the motel about an hour after he realized Dean was going to be a while.
Dean avoided eye contact as he shrugged out of his jacket. “She won every round,” he mumbled, “Took all my money, and couldn’t even stop by for a beer.” Dean plopped on his bed, putting an arm over his eyes.
Sam laughed, “She sounds like a shot of whisky with a side of Tabasco.”
“You have no idea….” Dean sighed. “She’s a hunter too. She knew who we were.”
“Really? Huh. What was her name?”
“(Y/n).” Dean sighed again. “She was damn near perfect, Sam.”
“Who knows, maybe we’ll bump into her again soon.” Sam got into his bed and flicked off the light.
“I’m counting on it,” Dean rolled onto his side. Because I want her so fucking bad.
Stanford is different than Sam thought, but much better at the same time. Being away from his father finally gives him the chance to be himself, without getting talked down for it. He made some really cool friends, studies hard and is one of the best students in his courses. He’s what he always wanted to be: free. He doesn’t miss the stinky motels, the hours on the road, the hunts.
But at the end of the day, when he lies in his bed, an arm behind his head and looking at the ceiling there is the feeling that something is missing. Someone, to be exact. He doesn’t miss his dad, not even a little. But he misses his brother. Oh god, he misses Dean so damn much. Every day he wishes he would have asked him to come with him, to run away with him. But he didn’t. And now he can’t even call him because the number he knows is always turned off.
Yeah. He misses Dean. But Dean is in the past, doesn’t help anymore now.
It’s another day like the rest, the exam in front of him almost completed. He’ll finish it, then grab something for lunch because he skipped breakfast again. Sam really should eat more, but his appetite is barely existing at the moment. He’s getting skinny slowly and hates it. He’s just marking the last answers when someone knocks on the door. Carefully he looks up, seeing one of his teacher’s peeking in before walking over to the current one, talking with her. When they look at him Sam frowns.
“Mr. Winchester, are you done with your exam?” The teacher asks and Sam nods confused. “You may leave then. Mr. Miller will tell you why.”
That doesn’t sound good, not at all. Sam’s chest tightens when he packs his stuff together. It’s only two minutes until he hands the exam in, not even caring anymore what grade he’ll get, and follows his other teacher outside.
“What happened?” Sam asks the moment they are outside.
“Apparently a family emergency. Your brother waits in my office, he just told me to get you as soon as I can.”
Sam stops, staring at the man thunderstruck. If Dean is here –
“Dad!” He lets his bag drop and runs to the office two floors below him, almost tearing the door apart when he rips it open and sees his brother, sitting in a chair. “Dean! Dad – is he… is he hurt?” He’s panicking so much now that he can’t even be happy to see Dean, can’t even remember that he ran away. Because his dad is still his dad, no matter what.
Dean jumps up, shaking his head. “Hey, it’s good, Sammy, really. I’ll explain, okay? Just calm down.”
The teacher comes in and has a quick talk with Dean, but Sam doesn’t even listen. If his dad is fine… then what the hell happened? When Dean puts a hand on his shoulder and guides him out; he doesn’t even protest. It’s only when they slowly walk down the hallway, away from the classrooms, that Sam frowns.
“Dean, what –“
He can’t continue. Dean pushes him against the wall, his lips crashing against Sam’s in an almost desperate act, hands roaming his sides. Sam groans into the sudden kiss, his confusion and panic melting away at the strong and still tender hands of his brother. Dean bites Sam’s lip, demanding entrance and Sam is so willing to obey that he’s questioning his own sanity. But god, Dean always had this effect on him, always managed to make his brother melt into his touches and their kisses.
Dean breaks the kiss only to sink his teeth into Sam’s neck, causing him to tense up and ache against him. His hands claw into Dean’s shoulders, so hard that he can feel his nerves screaming.
“De, stop that!” Sam groans, but the older one just grins against his skin.
“Come on, Sammy, you love it when I’m like this, don’t you?”
“Fuck – yes. But not here, dammit!” It’s just a matter of minutes until someone will come this way and see him. And Sam doesn’t really plan to be the boy who fucks his brother, thank you very much. “What are you even doing here?”
Dean huffs, a hot blow against Sam’s skin, and steps back.
“Not happy to see me?” Sam wants to punch his brother for this innocent look in his eyes and the pout, implying that he didn’t just hump him against the corridor wall; but damn, this is his weak spot and Dean fucking knows it.
“No, Dean! Fuck, can’t you just call or something? I almost had a heart attack, I thought dad died!”
“Um… about that…” Dean smirks and scratches his head with a sheepish look on his face. “Sorry?”
Sam rolls his eyes and pushes Dean back; storming off to get his backpack he dropped earlier, Dean on his toes. He doesn’t even turn around, apparently he’s done with school for today so he might as well just leave. Great, another class wasted that he’ll have to take another day…
“Hey, c’mon! Don’t be like this now!” Dean grabs Sam’s shirt before he can leave the building, turning him back around. “I just missed my little brother, okay?”
Sam sighs, shaking his head. “Next time: do me the favor of calling, will you?”
“Promised.” Dean grins and leans in for another kiss, this one just as hot and demanding as the last; and Sam just can’t resist. He lets his backpack drop once again, only to grab Dean’s neck and wrap his other arm around his waist, pulling him closer. He hums silently when Dean pulls back, eyes looking into those emerald ones with a gleam of need in them.
“I missed you too, big brother.” He whispers, almost a purr against Dean’s soft lips.
He doesn’t even care that he misses a class anymore.