Series Rewrite- Background Stories

Your First Kiss

Author's Note: In this, the reader and Dean are 15 years old.

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There comes a time where a high school crush or your first kiss or high school parties were all anyone could think about. There comes a time where nothing else mattered besides those key points. High school crushes were only a phase that eased your aching heart but back then, you never thought you would like someone else.

Of course, you had a thing for Dean Winchester, you practically grew up with him and his brother, Sam. But you could never tell him how you felt because he was Dean and all the girls went for him in high school. All he ever did was hooking up and keeping his distance. They never knew what went on beyond high school but you did.

Maybe that is why you fell in love with him at such a young age. So, to get over this "crush" you had to push your feelings to someone else, Trevor Leash, Mr. Popular of Sophomore year. You watched him from afar and you liked what you saw. He was no Dean Winchester but he wasn't bad looking either.

He was the type of guy to hang out with Cheerleaders, go to the biggest parties, kiss the pretty girls and you were almost positive that he wasn't a virgin anymore. You thought that if you hooked up with him at least once, your feelings for Dean would go away so you tried talking to him.

You were shy as hell but you weren't going to let him know that. However, with all the girls around him glaring at you, you couldn't help but let your walls crumble a little. You were so hooked on him that you didn't see this ending well.

"Hey, Trevor." You walked up to him with a shy smile.

"Oh look, nerd girl wants his attention." One of the cheerleaders snarled.

"Jen, relax." Trevor winked at her and looked at you. "What's up?"

"Um, well, you're going to the big party this weekend?" You cringed inwardly. Of course, he would be going to the party. The girls snickered at this question and Trevor got up, putting an arm around you, walking you away from his "group".

"Sorry about them, they don't know when to behave."

"It's okay." You blushed at contact with him.

"I am going to this party. Why?" He grinned down at you with pearly whites. Dean's smile was more gorgeous.

"Well I was thinking of going and you were going. I mean, we don't have to go together, but maybe, if we see each other there..." you bit your lip. This was harder than it looks. Being 15 years old really didn't look good on you. Your mother was probably turning in her grave if she saw this.

"Do you want to go out tonight?" Your eyes widened and you looked up at him, your mouth partially opened. Remember how to speak.

"What?" Way to go, Y/N, he thinks you're an idiot.

"I know this great diner that serves the best food. Call it a date?" He grinned.

"Sure." You didn't know what else to say. Your heart was racing and butterflies were erupting in your stomach.

"Great. Why don't you text me your address and I'll pick you up?" Again, all you could do was nod and he winked at you, giving you his number and walked away. Did that just really happen? You broke out in a smile, thinking you were going to have a great time, going to get your first kiss and maybe more from him. You couldn't wait to get over Dean.

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The date comes and Dean refuses to even look at you. It was like he was jealous or something.