Loser | Dean Winchester x Reader High School AU

King of the Hill | Chpt 1 | Prologue

Welcome.

This will be replacing Painted Smile on Thursdays!

I've decided I'm going thru with this certain Dean x Reader, Bc my idea can't really be summed up in a oneshot.

So here we go.

Dean's POV

"Dude! I haven't seen you like all summer!" Azazel clapped me along the broad muscles of my back beneath my thick leather jacket and I grinned. It was slightly too warm in the school, enough to make you sweat, as the school hadn't turned on the air conditioner's all summer. Sucks to be the poor saps who had to go to summer school.

"Been working on my dad's car and traveled on the road with him," I said, my chest swelling with pride. It was my car for the year, my dad always out on business meetings. He used a rental car most of the time.

"I heard you broke up with Lisa too!" Ruby said with a smirk. I nodded. My friends were far from fond of how long I dated Lisa.

"She already had the name picked out for our kid, Ben or something, and I was not about to let that one slide," I said and I watch Azazel shudder. Lisa was hot, and a super nice girl, but she was far too serious about relationships than I was.

"So? Starting the year off strong and single, who's the new target?"

"Hmm, I was thinking more of a challenge this year," I said, flashy a toothy grin. Azazel and I often played this game. The more girls we slept with and dated would push us up on the scale, to become 'king of the hill', though we weren't really competitive about it.

"What about that Jo chick?" Ruby asked and Azazel shook his head.

"No, they love Dean over at that diner, way too easy," Azazel said.

"Charlie?"

"Hear she's gay," Azazel said, flashing me a look. She was always the odd one. I glanced over to see that Charlie had come bounding down the hall, towards her locker. Perhaps that's why she popped into mind.

"Come on guys, I'm feeling pretty good," I said, leaning up against a locker.

"I got it." Azazel whispered his answer to Ruby who smirked wildly.

"Who?" I watched Azazel nod over to the locker Charlie was standing adjacent to, gesturing as she spoke to her best friend (y/n).

"Oh hell no."

"Dude, you said you wanted a challenge. (Y/n) is a nerd and hates your guts. It's going to be impossible."

"Exactly why I can't do it."

"You said you wanted a challenge!" I sighed, glancing back over. "Besides, you don't actually have to sleep with her. We won't make you do that, that's just cruel. We just need enough to make everyone think she slept with you."

I glanced back over at Azazel. I could see new plans for Senior year was exciting him, especially news of embarrassing others. Plus he knew how much (y/n) and I despised each other, and this served as a way of revenge. I was always up for a challenge, and as much as I didn't want to spend time with (y/n), she seemed like the best option.

She for one, has hated me ever since elementary school, and for another was a tad too smart for me. I may get good grades, but she was top of class smart, and I couldn't compare. She definitely wasn't stupid. But then again, the hate is mutual, and the prospect of embarrassing her seemed to have several benefits. To get with her and break her was an accomplishment.

"I accept."

"You do?"

"Totally. I don't have to actually sleep with her, and I get to ruin her life a little. It's a win win situation," I laughed, pushing down that nervous feeling in my stomach. Normally I wouldn't be so quick to agree to one of Azazel's schemes, but (y/n) and I have been at odds for so long it was hard not to.

"Good, I'll give you all the time you need, because honestly I want to see this one play out," he laughed, glancing over at the two with a haughty look. Charlie gestured something and ran after Jo, who was turning a corner.

(Y/n) was now wide open and free to make the first move on, but I was already having trouble deciding what my first move was. I thought for a moment before considering my options.

"Well? Go on. Get that loser," Ruby sneered and I grinned, striding over to her locker.

Short but kind of a prologue thingy.

~Calymari