Meeting Them - Teen!Dean x Teen!Reader

First Night

"This isn't horrible. I've seen way worse than this At least there's two beds. Who's sleeping with who?" said Sam who flipped open the phone book and began leafing through it. Dean twirled you around so that you were pushed up against his firm chest. "I could sleep with you, sweetheart. It'll be exciting," he said with a smirk. You wriggled away and noped right out of that awkward situation. "Haven't decided. Oh, check this out, I could go for some pizza right now. Maybe the spinach. That's goodie," you said, pointing to a local delivery joint. Dean flopped on the bed and you remembered. "Nope, you boys at the table and I have something for you," you said, pulling the papers out of your bag and placing them in front of the boys. "The hell is this?" they said in unison. "Watch your mouth, Sam," you chided. "They're something to get you both into the advanced classes and maybe get Sam bumped up a few grades. I know your both smart: John wouldn't have it other way," you explained with a grin. Dean crumpled his up while Sam searched for a pencil. You put your arms on the back of his chair and lowered your lips to his ear. "Because I might change my mind about who I'm sleeping with if you actually try your best." He groaned and stood up. "The things I do for hot girls these days," he mumbled as he went to your bag to grab a pencil.

They did as you asked. You ordered two pizzas and laid down on the bed until they were done. "There's a folder in my bag, just stick it in there. Make sure to put your name on it," you told Sam once he was done. He did as you told and flopped down beside you. His baby cheeks were slightly sunburned and you grinned at the young boy. "You're not a freak, you know. You shouldn't hate yourself. You've saved people, your brother, too. Even if I hate your dad, you're an amazing boy, Samster. I hope you know that," you said, giving him a hug. "I like this squish. He is my squish and I will love him and pet him and stroke him and love him and call him Sam," you said, slap-petting Sam's head. He laughed and then you noticed Dean was staring at you both with a soft smile. You don't know why, but you blushed. He started to get up, but someone knocked at the door and you ran to get it.

You gave the boy the cash and a little extra as a tip, a wink, and you were throwing Dean one box and sat on the bed with the other. Taking a bite, you moaned a little and mumbled. The TV had some infomercials that you all laughed at and made snarky comments towards. It was, all in all, an interesting night. Sam finished what little homework he'd been assigned, flopped on bed, and promptly fell asleep. You and Dean worked together on yours for a while. It was almost midnight when you finally finished. "We could stay up a little while longer and watch some TV if you wanted," Dean suggested. "No, I'm tired. You don't have to, but I'm going to bed, too," you said with a yawn. The corners of his lips tugged upwards, but he kept a straight face. "Okay, sissy, go to bed if you're so tired," he said with a smirk. You stuck your tongue out and leapt cross the small room to the equally as small bed. Your curled up into a ball to try to keep warm and closed your eyes. Humming a soft lullaby, you gently drifted into a light sleep.

Not much later, you felt a dip in the bed that you knew was Dean. Pushing yourself into consciousness, you kept your eyes shut. You felt something warm drape over your shoulders. Another few movements, and then everything was still a click, then darkness. You opened one eyes to see a sliver of moonlight falling on Dean's resting face. "I get why you reject me, y'know. God, you're so far out of my league. Beautiful, brilliant, talented, caring, everything. I want you, and not your body. Like, you. I want you to be mine, God knows you're one of my only chances in this line of work. But I'd quit for you. I've only known you one day, but I feel like I've known you my whole life. I wish I could hold you right now," he murmured, eyes searching your face. "Then do it, idiot," you mumbled back. He was obviously shocked at your sudden speech. He didn't move for a long while. But then when he did, he pulled you close to you and buried his face under the jacket he'd given you.

"Good night, Dean."