Cheers and beers supernatural Fanfiction (Dean x Reader)

Chapter 4:

I sat in the backseat, adjusting a little, pulling on my skirt as we drove toward the police station. I groaned in annoyance, I never liked wearing skirts. "Would you chill? It's only for a few hours..." Sam said from the front seat. "Easy to say when you're not the one in the mini skirt!" I exclaimed, pulling on it again. Sam sighed, rubbing a hand over his face.

"Hey... we're almost there, don't worry sweetheart." Dean reassured, smiling back at me. He quickly looked back at the road, pulling into the station parking area. As soon as Dean parked, I hopped out of the car. "Wait, I didn't even turn off the car yet!" Dean exclaimed, watching me as I dusted off my skirt, smoothing it out. "Geeze..." Dean turned off the engine, climbing out.

Sam started walking toward the entrance, but Dean walked over to where I was. "Look... I get you don't have the best past with skirts...but c'mon. Please do this." Dean said, looking into my eyes. "Fine..." I glanced around him, seeing Sam giving us a 'what are you doing?' look. I sighed, following Dean as we walked up to the entrance.

[FLASHBACK:]

I smiled, getting out of the impala. It was prom. Dean drove me and his date, she was super nice. Sam was gonna go, but he didn't have anyone to go with. So, I dragged him out here anyway. "C'mon Sam! Look, there's punch!" I squealed, grabbing his hand, and pulling him toward the punch line. "There will be some on your face if you don't stop dragging me places." Sam groaned. "Oh, shut up grumpy." I said, not letting him ruin my mood. "Why do I have to be here, no one asked me to prom...this just makes it more depressing. I'm here with a friend." He sighed.

I filled a cup up with punch, pointing in his face after taking a big gulp. "Actually, I'm practically your sister." I said, grabbing a cookie from a plate next to the punch. "Whatever, same difference." He rolled his eyes. Sam groaned annoyedly, sitting on a bench. "Cheer up Sammy!" I grabbed his hand, pulling him up. "Let's go dance!" I exclaimed, pulling him onto the dance floor. I did a twirl, spinning a few times. He just stood there, "why are you so sad?" I asked, stopping my spontaneous twirls.

"I asked a girl, but she didn't wanna come." He sighed, looking down. "Why not?" I asked, tilting my head. "She wasn't interested, dummy." He looked up, at someone behind me. "Who?" I asked, angry someone would upset him like this. "What?" he questioned. "Who?" I repeated, louder. He mumbled a name I couldn't hear. "LOUDER PLEASE!!!" I yelled, over exaggerating. "Geeze... calm down. It was Alice Campbell." He said, moving his hands, showing me to quiet down. "Alice. Campbell." I repeated, looking around. I spotted her...she was wearing a shiny pink sequin dress.

It made it so much easier to get angry at her while she was wearing my least favorite color. "Hey! You!" I practically screamed as I charged toward her. "Wait, (Y/N)..." Sam tried stopping me but I waved him off. "What do you want?" she asked in the snottiest voice I'd ever heard. "You really think you can just reject my best friend, Sam Winchester, and not hear a word from me!?" I yelled. "Yeah? Whatever... he's not my type. Little too nerdy, and way weird." She rolled her eyes. My mouth went agape, "What did you just say..." I growled. "He's ugly, and weird. His hair's way too long." She pressed her lips into a firm line.

"You bitch." I lunged at her, punching her in the face. She stumbled back, "Uh- who the hell do you think you are?" She said, reaching for me. I stumbled back, "Woah..." I exclaimed, falling. She tore my dress...and everyone saw my underwear. The top was barley there and everyone busted out laughing. "Shut up!" I screamed, wiping the tears in my eyes. "Woah...Woah...(Y/N). What happened?"

I heard Dean's voice asked as he helped me up. "I- I don't know..." I said, frantically looking around. Dean pulled off his Jacket, wrapping it around me, helping me cover up. "Thanks..." I sniffled. "No problem, sweetheart, let's get outta here... c'mon Sammy." I looked back where Sam was standing speechless but looked angry. At me.

[END OF FLASHBACK:]

I frolicked into the motel room, happy to take off my skirt and get into a hot shower and then normal Pjs. I jumped over to my bag, pulling out a pair of sweatpants and a black t- shirt.

[SAM'S POV:]

I remembered the night of the dance vividly... maybe a little too vividly? I never understood why she helped me at all. But I guess after that we did leave the school on another case... so it didn't matter anymore. You'd think? But no. Both me and Dean remembered...and Dean actually admired the way she stood up for me. You couldn't wipe off the grin on his face for weeks. It was hilarious how much Dean loved this girl.

She would fall and instead of laughing anymore, he was the first person to help her up. I, however, laughed. Which makes me seem like a douche' now... but I can't help it. But I have noticed, how dean is totally head over heels for this girl. He literally shared his pie with her. I looked over from my spot on the bed, to see Dean carefully folding (Y/N)'s clothes and putting them neatly in her bag. Where did Dean go...who is this?

"Dude, what the hell are you doing?"

I asked, watching him look so focused on the evenness of the shirts that were lined up. "Helping her pack... what's wrong with being neat?" He looked at me and I scoffed. "Wanna know what I think? You're crazy. You must really love her, man." I closed the computer on my lap, setting it aside. I crossed my arms over my chest, sitting up. Dean glanced over at the bathroom cautiously shushing me. "Sam! Careful... she could be listening." He whisper yelled.

"Man...I think you need to tell her." I stood up, walking toward him. "I can't just 'tell her' Sammy!" He exclaimed, throwing his hands up. "And why not?" I asked, giving him a knowing look. "We've known each other for so long...we're like siblings almost. It'd be weird." He sighed. That's when I completely remembered what we were talking about before... about how he has had dreams about- a nicer way of putting it- doing (Y/N). And it's kind of annoying when he goes into detail...but she's like my sister. Which makes me disappointed in Dean since he thinks of her in that way. That's really weird. Then again, it is Dean we're talking about. So, what the hell. I guess I kind of always thought they had some kind of weird chemistry. "Dean... just, tell her. What's the worst that could happen?" I asked, sitting down across from him on the opposite bed, resting my forearms on my knees.

"Everything! She could think I'm an idiot, or- or not have feelings back... or she could even hate me." Dean ranted, burying his head in his hands. He'd never cared this much about what a girl thought... it made me smile.

"Dean... she won't. Just, c'mon. Please tell her. I'm tired of this stress on you, about a girl, Dean." Dean continued staring at me with a blank look. "Dean! Tell her. Um, okay, think about it this way..." I thought for a second, trying to think of some wise brotherly thing to say. I had nothing. "I'll buy you pie if you tell her." I sighed, giving him a pleading look. His eyes widened, but immediately he went pale. Boom. A weakness. He kept opening his mouth, about to say something.

But no words came out. Finally, he pointed a finger in my face, "You're lucky I love pie..." Dean scowled. "Fine." He grumbled, standing up. "Okay. When she gets out of the shower, tell her." I stood up too, patting his shoulder. "Yep." He mumbled, running a hand through his hair.