Supernatural Imagines

Best Friend's Brother (Dean x Reader)

Warning- Some sad mentions, smut
Summary: I just watched Kissing Booth, so it inspired me to write this one. Y/N falls in love with Dean despite being Sam's best friend.

Sam and Y/N have been best friends since forever. John and Y/N's dad used to hunt and so they met up quite often for a chat, leaving the kids be. Y/N was always around the Winchesters. Dean mainly watched her and Sam. There would be those interesting nights when they did Truth or Dare or talked deeply about life.

Eventually as they all grew older, the more the trio separated and went their own paths. Except for the fact that Sam and Y/N would call and email one another when they had the time to catch up.

Y/N and her dad had to take a break from hunting when he got really sick. Turned out to be cancer and it never went away. The treatment was not the best and her father was losing more energy every day. That was until he was put in hospice.

Y/N hated hospitals after that. She immediately called up the boys and explained what happened. She did not want to be alone right now. She couldn't be. She felt lost without her dad.

Sam and Dean shortly came to pick Y/N up and they had been on the road ever since.

-a few years later-

John was barely taking the kids out of school to leave another town. Again. Y/N didn't know how much more she could handle of this going back and forth. Sam seemed annoyed by it too. Dean, not so much. He kinda just goes with the flow. He always adjusts to a new place fast and finds a girl to latch his lips onto.

Y/N and Sam were at lunch making silly faces with oranges in their mouths when Dean came to pick them up. He got a few whistles from some students in their grade. Y/N shot them a glare and took the orange slice out of her mouth. "Cmon, guys. Don't make this any harder than it has to be." He told them both. Y/N and Sam gathered their stuff and they huddled into the Impala.

Sam and Y/N started to play iSpy in the car and Dean jumped into the fun. John focused on the road. At one point, he turned up the radio to drown out their voices. Dean tried to turn it down but got his hand slapped. "Driver picks the music, shotgun shuts his cake hole." He told him stern. Dean frowned and looked back out the window.

Y/N noticed and shared a look with Sam. Sam shrugged.

—————

John dropped them off at yet another hotel with another fake credit card. Dean got them the room easily and checked in. Y/N and Sam got adjusted to the room with their belongings. Y/N ran to a bed and claimed it as hers. "Hey, no fair! We sleep together!" Sam snapped.

"Guys," Dean raised his voice at the two. They both looked over. "I'm in charge and there's two beds. Each of us has to share. Pick a bed and let's go." He told them. Y/N nodded.

Y/N saw Dean's eyes linger on her for a bit longer. He smiled and set his things down. Y/N watched Dean do so and saw how his muscles flexed underneath his shirt. She felt blush rise to her cheeks as she thought about him. Woah, he's Sam's brother, I can't be liking him like that... he's all gross and old, Y/N thought. She pushed those thoughts down when she saw herself. He couldn't possibly like me, She thought.

—two years later—

This year had been crazy. Sam and John got into this crazy fight about hunting and living a normal life. John told Sam to leave if that's what he wanted. Sam had looked at Y/N for reassurance and asked her to come with him. Y/N agreed only because she wanted a restart too. They barely had any friends and it got quite lonely being on the job. John wasn't a good team player and bossed everyone around.