Dean Winchester Imagines

Time's running out

You had just sold your soul. For what price? Your brother's life. He was the only family you had left ad you couldn't lose him, not like the rest of your family. Most of them wanted a proper hunter's funeral and although it pained you, you let them have it, even though you wanted them back. You granted them their final wish.

One time you had an appearance from your sister, she was dead but she was back and as a ghost. You didn't want to finish her off but that was the only option you had. It pained you even more to see her face filled with hatred towards you, you knew it wasn't your fault but you couldn't help but blame yourself. When your brother, your last living family member, was killed right in front of you, you immediately knew you had to save him. And selling your soul was the only way to do it.

You'd gotten the correct things needed to summon the crossroads demon, you made the deal and sealed it, no going back. You then went back to your brother who had no recall of where he was. You had lied to him and explained that he got knocked out on a hunt. He nodded and believed you.

5 months after the deal was made, you told your brother what really happened. Of course he was really angry at you but he could also understand why you did it, you didn't want to be alone. Over time you both knew what would happen to you by the end of the 10 years and you were planning for it in advance. Little did you expect what would happen.

1 year after you had made your deal, your brother had gotten severely injured on a hunt. You were scared beyond belief. Getting him to the hospital was a challenge. When you had managed he was barely here at all. The morning after you had taken him in the doctor came to you and told you that he had passed away in his sleep. To this you cried, for ages. You couldn't let him go.

~~~

Now, 8 years later, you were hunting with the Winchesters and have been for the past year. You were on a hunt when you first met them you were working the same case of course. Several young children had gone missing and the only lead was sulphur at every scene. You had agreed to work with them and eventually you stayed with them. You hadn't told them that you had sold your soul, for some reason you couldn't bring yourself to do it.

Currently you and the Winchesters were hunting 6 demons that were getting people to sell their souls and were cheating them by making them have 'accidental' deaths. You didn't know whether anything would be mentioned about you going to hell but you prayed that it wouldn't, you couldn't have the boys find out.

Dean and Sam went around the back and you confronted them first. The lead demon smirked.

"Well well well... I wasn't expecting to see you for another year Y/n, this is a surprise!" he praised.

"I'm not one to have expectations for, even you should know that" you noticed the boys enter the room but you kept eye contact with the demon.

"You're little deal to save your brother was really cute, it's a shame you couldn't bring him back a second time" the demon smirked, knowing how to push your buttons.

"Don't you dare bring up my brother." You snarled.

"Or what? You gonna cry on mummy's shoulder-? oh wait, she's dead too isn't she? Your whole family is dead and soon you'll be joining them" Then he was stabbed in the back and he began to glow.

"Not today you son of a bitch" Dean hissed as he retracted the blade from the demon, making it fall to the floor. "Y/n? You okay?" Dean asked as he approached you.

"Yeah, why?" You weren't sure why he asked.

"Because you're crying" You raised your hand and wiped away the tear subconsciously. Then you realised why you were crying.

"I-it's not nothing" Dean said "Tell us what's wrong" Dean sat you down. You nodded, time to get it off of your chest.

"Most of my family passed away years ago leaving it with me and my brother left. He got injured on a hunt and I managed to help him, however he passed away a year later." You repsonded, trying to avoid telling them that you sold your soul.

"Y/n, what did he mean when he said that he wasn't expecting to see you for another year?" Sam asked. You knew that there was no escape now, you were going to have to tell them. You looked down.

"When my brother got injured, he wasn't just injured...he got killed. H-he was the only family I had left and I didn't want to lose him so I..." You couldn't finish, you just couldn't.

"No...You sold your soul?" Dean asked, looking shocked. You nodded.

"Then when he died a year later, I was devastated. Even though I tried to save him, he still died in the end." You couldn't look at them.

"And how long ago was it when you sold your soul?" Sam asked.

"9 years today actually" you said, sadly smiling a little.

"Oh god" Dean mumbled "We have to do something Sammy"

"Dean it's no use, I'm done for. I'm so thankful that you both took me under your wings but I can't stay with you two. I can't let you go through with losing me in a years time, It's not right. I appreaciate everything you both have done for me but I can't continue with you" You stood up.

"No, you're not leaving us. After being with us for this long, we aren't letting you leave now. We'll stay with you 'til we either find a solution to this problem, or we...we watch you go" Dean stood in front of you, blocking your path.

"I don't want you to do that-" Dean cut you off.

"No, we want to do this" Sam smiled slightly at yo and you knew that if you were to go, they would give you the best funeral a hunter could get.