The Boyfriend Trap (HS AU)

Making Plans

Requested on instagram by: @fandom._.city

Prompt:Destiel with punk!Cas and jock!Dean! Or a fanfic where Sam tries to set up Dean and Cas so he asks Gabriel for help and together they don't only end up getting Cas and Dean together, but also fall in love themselves!

Sam sat quietly in the library, his nose buried in a book about law. This was usually how the young sophomore boy spent his lunch hours at school. He was a nerd and he knew it, but that way okay. As long as he had a book in his hand, everything was right with the world.

Well... almost everything.

Sam looked up and out of the library window, towards the cafeteria next door. 

From where he was sitting Sam could see the back of his older brother Dean's varsity football jacket. The red and white jacket was practically unmissable if you walked past him in the halls. On the back written in all bold white letters was their last name, Winchester.

Dean was sitting at the table with the other senior boys on the varsity team, along with all the hottest cheerleaders in the school. Sam didn't even want to know how many of those girls his brother had banged over the years. None of them lasted for more than a week but they still kept coming back to him for some reason. Low self-esteem maybe? Or maybe Dean was just really nice to them when he was with him. With Dean there was just no telling. His only seemed like a douche on the outside, when actually he was really caring and considerate once you got to know him well enough.

Sam figured that it was being a jock that had forced Dean into this hard, fake shell that he always wore. His brother had always been on some sort of football team at any given time in his life. If it was football season he spent nearly all his time out on the field, if it was off season the Dean would be in the gym training and out on the field practicing and trying to stay in shape. It was the sport their father had forced Dean to play ever since he was little. It wasn't like Dean wasn't good at the sport; he was the first string Quarterback for fucks sake, but Dean was also extremely smart too.

However, his grades didn't reflect that at all. Since football was taking up so much of his brother's time, he barely had any time for school work. Dean only made sure that his grades stayed high enough to keep him from getting kicked off the team. Not to mention all the pressure of not being a nerd and fitting in with the other jocks made being smart difficult for Dean. So he ended up hiding it from everyone most of the time.

Dean's mask was always up unless he was around his closest friends. However, recently Sam had been noticing that Dean's mask was staying up longer and longer the more time he spent on the field. Dean hadn't really hung out with not a part of the team in a while.

Sam knew the only reason that he wasn't expected to play football alongside his brother was because he had severe asthma. John, their father, would probably have still have insisted that Sam play on the team if it wasn't for Dean. Dean had insisted that Sam was simply unable to play sports and that he should focus more on his studies to become a lawyer instead.

Somehow, Dean had managed to convince John that this was for the best. Sam never quite knew how Dean had done it because their father was a very difficult man to sway, especially when he came home drunk. (Which is how he was more often than not.)

Sam felt sick to his stomach as he watched one on the cheerleader's, Anna he thought, snake her tiny hand down Dean's back and grip his ass lightly. Sam rolled his eye as he watched Dean turn to her and wink lightly. She must be his brother's new hook up for the night.

"He seems to be enjoying himself." Said an all too familiar voice behind him.

Sam tore his attention away from his brother and turned to see his best friend Gabriel pulling out a chair beside him.