Supernatural Stories and Imagines

Dean 10/ Not My Hookup

We've made it to 10 imagines for Dean!!

Plot: Telling Dean about a guy you hooked up with, what you don't know is that Dean likes you

Being sober led to intriguing thoughts.

"Dean, you wouldn't believe the night that I had." You laughed, still thinking about it. Nothing about the date was spectacular by any means. It was just reassuring to have someone so eager to be with you since you had been out of the dating game for a while and had not lost any of your moves. You didn't even have a hangover. Since it was the first time that you had sex in a while, it unfortunately mostly reminded you of the life you were living. You decided to focus on very positive aspects rather than the alcohol that drowns out your true emotions about the job and many things associated with it. You constantly doubted yourself, creating a facade that made you much happier on the outside. You knew that occasionally one of the brothers would be willing to share their real feelings and knowing they experienced similar things was reassuring. But to even have so much of a crush on one of the Winchesters should have been laughable to you. You were sure they had to see you like a kick-ass sister. It was a sad reality you drowned out by turning to one of the most intimidating men in the world, though you knew he could be a softie.

Dean frowned up at you, furrowing his eyebrows, as he nursed a coffee with a chocolate donut sitting in front of him. "And I care why?" He made a point to lift the newspaper. You walked over to him, scuffing up his hair that was already combed despite it still being early hours. You could see that his blue robe was barely tied over his loose pajama pants and a white t-shirt. "I have to listen to all your one-night-stands, so you get to listen to mine."

"I'm sure that some random you met at the bar was just fantastic," he retorted. Dean set down the paper and donut, crossing his arms, and looked up at you as he sat at the dining room table. "And don't touch my hair."

You reached over for his donut. Dean moved to swat your hand away, but you beat him to it. You stood behind the chair, resting your elbow lightly on his head. "First of all, Dean-o, we didn't meet at a bar. Second of all, I will do as I please with your hair and your donut."

He tilted his head far enough back to where green eyes gazed up at you, causing your elbow to fall back. You pouted but stepped back. "Fine." You took another bite from the donut before setting it back on the table. Of course, Dean wouldn't have used a plate. "But you're going to get crumbs all over the table."

"Well, maybe I want to." He sassed, snatching back the donut, focusing his stare back to the newspaper. Petty boy. "Oh, and Y/N, I don't give two craps about your sex life."

You rolled your eyes and began to go back toward the kitchen. "Someone sure woke up on the wrong side of the bed," you muttered to yourself. The younger brother appeared at the end of the hallway, slouching against the doorframe. Sam had just woken up as his stubble and messy hair was the first thing you noticed. He looked from you to Dean and back again before seemingly his best bet was to follow you to safety in the kitchen. He yawned, waiting for an answer to an unasked question.

"You want some coffee? I need some," you said. Maybe a light-hearted conversation would go better. Sam tilted his head, his puppy dog look much more intense right after waking up. You heaved a sigh. Sam knew you too well sometimes. "Fine. Short story shorter: I was attempting to tell Dean about some guy from last night and he got all crabby on me."

"Okay, yeah. Gimme as much coffee that's left. Who made this batch?" Sam opened the pantry with the cereal in it, going for raisin bran. You nodded your head towards Dean as you began pouring what was left into your favorite mug. Sam's eyes widened. "Scratch that. I'll just stick with cereal. And hey, I know you two get into your competitions and like to poke fun, but this might be the one thing you could be oversharing on. Before you get started, yes, I'm very aware of his own oversharing. Just go have a real conversation with him, for me?"

Not wanting to decipher all of Sam's many words at once, you nodded and took your coffee back over to Dean. He barely glanced at you as he continued to read the same section of the paper from earlier. His donut was gone and the coffee cup was empty. You sat down in the chair next to him realizing you had a headache. When it had been close to a minute of silence, Dean sat the paper down and took your coffee mug, taking a sip out of it, looking for a reaction out of the corners of his eyes. A small smile found its place on your lips as you watched this, your guard immediately softening by knowing he was not planning on acting butthurt over your prior conversation. Dean continued drinking the coffee longer than necessary.

"Can I have that back?" You finally spoke. Dean took a moment to consider, looking fondly at the coffee before setting it in front of him. "Okay then. Dean, I wanna know something. Why were you getting annoyed when I wanted to share about a night with someone that didn't mean anything?"

You watched as he pondered your question, how his lips puckered when he didn't want to answer, to the aversion of his eyes from yours back to the cup. He let out a puff of air and scratched the back of his head. Dean shifted away slightly and ran his tongue over his teeth. He responded with a question. "If it didn't mean anything then why did you want to share it?"

Your turn to pause and try to form a plausible answer. He surprisingly brought up a good point. You thought it through and gave the best response you could come up with. "I guess I'm not entirely sure. It kind of seemed like the thing to do, given how often you would tell Sam and me about the type of women you've been with."

"Y/N, have you noticed that I haven't done that in a long time? Gone out, brought anyone back, talked about any of that? It hasn't been for nothing." Dean was speaking slower and quieter. His eyes were piercing into yours, searching. For what, you were unsure.

"Dean, I don't understand." You realized that your voice was matching his, but you were very ready to break eye contact and focus on anything except for him. He ran a hand through his hair and his knee started bouncing. He took a couple of short breaths as if he was starting sentences, but not quite able to get them out. In a rush, Dean said, "Look, I haven't been with anyone else in a while because I didn't think it would be right of me because I like you and yeah, I know that doesn't make sense. It's obvious you don't feel the same so it doesn't matter. There you go, that's why I don't want to hear about you with other people."

Dumbstruck was the only word you could use to describe how you felt. Here was your best friend, a man you had fallen for, someone you believed saw you as a sister, sitting here before you, confessing his feelings.

You were at a loss for words. You reached for your coffee, but Dean got to it first, switching the roles from earlier. Could you just say it was too early for this conversation and go to sleep? You knew that this was important and needed to happen, but were taken aback by the shock of the situation. He took a sip of the coffee and you wanted to point out that you hadn't even had the chance to drink any yet.

"This is the part where you say something," he said to the coffee cup.

You exhaled. "You aren't kidding? Like, you haven't talked to Sam about this? Dean, what the heck, dude? Say something next time!" You let out a laugh, relief flooding you. "I do feel the same."