Supernatural Imagines 2

{56} Dean Winchester

Requested By: yami1269

Imagine: You and Dean spent a lot of time before the two of you fell in love. one day you make a deal with Crowley and don't tell Dean until it's too late.

Seventeen years. That's how long you had known the Winchesters. You were going to a small high school in Nebraska when they joined the school. There was something different about them, but you didn't know what it was. One thing was for sure, the Winchesters had you hooked from the moment they came into your life.

Dean made multiple attempts to flirt with you in school, but you shut him down every time, which both annoyed and intrigued him. One day, you caught Sam studying in the library and decided to approach him. When you did, Sam immediately tried to hide his book but you were able to clearly identify the title of it.

"You're reading lore," you stated and Sam shrugged his shoulders. "It's for a class," Sam lied. You smirked as everything began to make sense. They were hunters, just like you. "Oh, really? I thought maybe you were trying to gather some information on how to kill the werewolf in this town," you replied, nonchalantly sitting down in the chair next to Sam.

Sam swallowed thickly, his eyes never looking away from you. "What?" he asked. "You know, the five different murders, all with their hearts ripped out. The logical guess is there is a werewolf in this town," you stated.

"You're a hunter?" Sam questioned. "So are you, and I'm guessing Dean," you responded, making Sam smile. "We should tell Dean," Sam suggested and a slight blush dusted your cheeks at the mention of his name. Sam smiled as he pressed, "He likes you, you know?" You let out a laugh before saying, "Yeah, me and about half the other girls in the school."

Sam laughed at that and let it go, promising to keep your secret of being a hunter from Dean until you were ready. But that secret wasn't kept for long. You were hanging out with Sam and Dean in their motel room when the werewolf decided to target the three of you.

Dean insisted that you stayed in the bedroom because you didn't know what was out there. However, when the werewolf moved to attack Dean, you quickly shot and killed it. When Sam wasn't shocked about how you killed the werewolf, Dean demanded an explanation. An hour conversation later, you and the Winchesters were making promises to text each other if any of you needed help.

John came home later that night and you explained what happened. He was distant and didn't say anything to you and the next morning the Winchesters were gone. But, Sam and Dean both texted on a regular basis and when John went missing, they immediately came to you.

You spent the next year with the Winchesters, and it was like nothing had changed. You were best friends with the Winchesters. But, after John died, you and Dean grew closer. You did everything you could to make him feel better. Despite your inner protests, you fell in love with the elder Winchester. The two of you spent every waking moment together and after a drunken night together, Dean admitted that he was in love with you too.

The two of you were together in a completely loving and committed relationship and everything was really great. That was until things started coming up with Sam and Azazel. It was a whirlwind of emotions that all climaxed when Sam was taken by the yellow-eyed demon which led to his death.

When Sam died and Dean sold his soul you were heartbroken, completely shattered. You were confused and afraid to lose either of them. But there was one thing you were sure of, and it was that you couldn't let either of them die.

So, you summoned every crossroad demon you could until finally one of them told you who the big boss of the crossroads was. Someone by the name of Crowley. You hunted down Crowley and when you finally met with him, you were the definition of a mess. "Y/N, it's so good to finally meet you," Crowley told you.