Summary: You had a fling with Dean fifteen years ago and now he wants back into your life, but like all things, it’s complicated.
Characters: Dean x Reader, Sam (mentioned), OMC Dylan
Word Count: 4756
Warnings: smut, unprotected sex, oral (female receiving), slight angst
A/N: This is a 2-part story the
second installment will go up later this week. Italics are memories you can read part two HERE. This fic wouldn’t have happened without some very important people:
@wheresthekillswitch thank you for being my beta on this. You are brilliant at finding the weak spots and helping me fix them.
@arryn-nyxx thank you for the AMAZING aesthetic you captured the story so perfectly.
@pinknerdpanda thank you for reading it and giving me your expert angst opinions.
If you’d like to be tagged please send me an ask.
It was days like this that were the hardest. The days where your mind decided to replay one of the best weeks of your life.
Fifteen years ago you lived in this small coastal town in southern Maine with your mom. Every summer, for as long as you could remember, you worked in your mom’s bar. The summer of your senior year was no different. It was going to be the last time you worked there before you left for college in the fall. The town was buzzing with tourists and the bar was full but still you noticed him right away. He was tall with a cocky smile and the greenest eyes you had ever seen.
Your breath caught in your throat when he noticed you staring at him. Heat flushed your face as you quickly looked down concentrating on wiping down the bar. The next time you looked up he was gone. You retrieved clean glasses from the kitchen and walking back out you almost squeaked when you saw him sitting at the bar. You stayed behind the bar stacking the clean glasses when he leaned over.
“Hey, sweetheart,” he said smiling at you. “How ‘bout a beer?” he asked.
“How ‘bout some ID?” you asked cocking your eyebrow.
He couldn’t be much older than you and you’d just turned eighteen. He laughed and licked his lips.
“Sure,” he said reaching into his back pocket.
He pulled out his wallet before handing you his ID. You looked at it and looked back up at him.
“So, Freddy, what brings you here from Minnesota? By the way you look great for 48,” you laughed handing his ID back. “Nice try.”
“Shit,” he looked through his wallet again. “Sorry, that was a joke, my brother, he…”
Green eyes handed you another ID. You looked down at it and handed it back to him. Hmm, 23.
“Ok, Dean, what’ll it be?”
He smiled, his cocky grin finding its place on his face once more.
“What’d you recommend, sweetheart.”
“We’ve got a nice blonde on tap,” you suggest.“
Then I’ll take that.”
You poured his beer setting it down in front of him before going back to stacking glasses. Dean stayed at the bar drinking his beer and looking around. As you stacked your last glass he caught your eye.“
So what’s your name, sweetheart?”
“Why do you want to know?”
“I always like to know the names of beautiful women.”
You laughed; he was cheesy, but also kind of adorable.