Dean Winchester One Shots

Piggy Back Ride

It was a customary occurrence for Dean and his girlfriend to go for drinks after a hunt. Most often Sam would join just as he did this evening though he had occasionally opted to go back to the motel and rest up afterward. Tonight was a night for celebration. Y/N had joined the Winchesters shortly after her parents passing, in the pursuit of revenge. Y/N had lost her two favourite people one fateful morning, finding then delicately planted in her garden, limbs and flowers alike stood tall in the dirt. She had just turned 20 and had come home from college to celebrate her birthday with her parents when she found them. She spent the better part of a year harassing the local police for information on the killer, in hopes of finding justice. After the second year with no leads, the kills happened again, only this time a set of men claiming to be the FBI had shown up at her doorstep asking questions. The Winchesters had taken her under their wing explain all they could to her about what their life consisted of. It didn't take long for the boys to take pity on her given their similar situation. Losing their parents was something the boys had had to endure as well. They proceeded to explain the situation she found herself in. Turns out demons are real, as are most otherworldly things.

It didn't take long for Y/N to learn the ropes and for them all to agree that she could stick with them. She learned more and more with every case she tagged along on, growing closer to both brothers though on different levels. The brothers had agreed that she was a perfect fit, getting along with both of them so easily without an effort. Sam, the younger of the two, was easy to befriend, a partner in trivia and fun facts while both enjoyed teasing the eldest who was all work and no play. It took Y/N more effort to earn the eldest's trust, loosening Dean up over time with drinking games and billiards. He came to love the way she wouldn't put up with his crap and would instantly put him in his place. He came to love the way she would protect his brother as though he were her own. He came to love the way she would challenge his classic rock knowledge often surprising him with her fountain of information. It didn't take long for his brother to tease him about having feelings for her though Dean was in denial. He promised himself not to make a move until his wiser younger brother had said 4 words to him, not intending to jerk the though in Dean. He was simply saying Dean was gonna lose the race the three or rather two of them had decided to have. Y/N in a separate car while the brothers charged down the street in Baby.

"You're gonna lose her!" Was all he said and though Sam had spoken the words with a chuckle as Y/N raced past them to the finish line, Deans heart began to race faster than his competitor. Dean refused to waste any more time denying feelings after that, instead asking her out after losing the race. She had promptly agreed and thank god she had.

Now, as previously mentioned, tonight's drinks had been earned. They had finally caught and punished the demon that had killed Y/Ns parents. After years of searching, she could finally put them to rest. Y/N hadn't foolishly expected that sense of relief most people do when acting out of revenge. Rather, she simply wanted for that demon to no longer have the ability to do to other families what she had done to her own.

The three of them sat down at a secluded booth and order a round of the bars top-shelf whisky as means of celebration. After that, they each picked what they wanted to drink individually, enjoying each other's company. Y/N and Dean sat next to each other across for the lanky younger brother, all smiling and drinking before Y/N spoke, slurring only a tad.

"Guys, I just wanna say thank you. For taking me under your wing showing me the ropes, giving me the opportunity to stop that son of a bitch. It means the world to me. I mean really you could have just left me there without any explanation whatsoever. So, thanks you for everything."

"'Thanks you?' How much did you drink!?" They asked in unison laughing at her words.

"No more than you guys." She paused to count "Okay so like maybe only three more than you guys."