Dean Winchester Imagines

You aren't the only one who went to hell

You had been in Purgatory ever since you, Cas and Dean stood too close to Dick Roman when he exploded. That was two years ago. Word had spread little over a year ago that Dean Winchester and Castiel had escaped Purgatory with a vampire called Benny. 'Great' you thought, at least two of you got out. You had wondered if they remembered that you were still in Purgatory. Unlikely.

You were always on the move with it being purgatory and you knew most of it inside out. The only thing you didn't know? Where the human escape hatch was. You wanted nothing more than to go back to earth. You didn't belong here and that made you a hotspot for the monsters.

At first, you were afraid, but time passed and you grew a pair and realised that you should've been alone all along. You had grown to be fully alert 24/7 and you were always on the move, in attempts to find that portal home. Yet, even after two years, you had no luck. You convinced yourself that you were destined to be here forever.

Your journey in Purgatory even lead you to the discovery of the back door to hell. Accidental, obviously but you realised that it was hell the second you stepped into the place. People crying and screaming, it felt awful and everything had bad written all over it. You left there as soon as physically possible.

One day, long and painful like the rest, you noticed something in the distance. It was blue and looked like a rip in the fabric of space and time, naturally you thought it was the portal and raced to it, killing anyone and anything that had gotten in your way. You entered the portal and you came out in the woods. You weren't sure if you had escaped after all. Luckily you had your phone on you, somehow it still worked. You dialled Dean's number and brought the phone to your ear. It rung 5 times before someone picked up.

"Hello?" Dean said and you smiled. It was so good to hear his voice.

"Dean! Oh my god it's so good to hear from you, it's Y/n" You said, for once in two years, several things were going your way.

"I highly doubt that, Y/n's dead. She died two years ago. So whoever the hell this is, I suggest you don't call this number again or I will track you down and kill you myself" You should've seen that coming.

"How about this..." You started. "You track my phone and meet me at the nearest motel to my location. I prove who I am and we all spill our experiences of Purgatory. Got it Winchester?" the anger spilled out of your voice.

"Whatever you say, how does noon tomorrow sound?" he answered.

"Fantastic" You growled and hung up the phone. You then made your way to the motel, which took you the entire night but you finally made it to the motel.

~~~

The following day, around noon, you heard the infamous sound of the impala pull up and you arose from your place. You approached the passengers side as you saw Sam and Dean exit the car. They both saw you and stared at you with wide eyes.

"Y/n?" Dean said as the brothers approached you and Sam performed the safety precautions, making sure it was you and really you.

"It's me, do you believe me now?" You called, the anger hinted in your voice.

"Yeah, I believe you. How did you-?" You cut Dean off.

"You didn't think I'd survive Purgatory did you?" Dean nodded. You were annoyed to say the least.

"You've changed a lot since we last spoke" Sam and Dean sain in unison, you just rolled your eyes.

"Yeah well Purgatory changes you. Before a scared little bitch. Now? I don't even recognise myself" You said honestly because that's how you felt. Heck, you didn't even feel human.

"Let's go inside and talk" Dean proposed the idea and you agreed to it. Once you entered the motel room, you sat down on the bed and sighed contemptly.

"So Purgatory..." Sam began.

"Where do I begin? You don't eat, you don't sleep, you don't shower and become more aware of everything. Even though it's a horrible place, I made a pretty interesting discovery while down there" You looked between the two boys before Dean asked you what it was.

"I discovered a back door to hell" You watched as the boys eyes widened.

"Did you go in?" Sam asked and you nodded.

"Look, I'll only say that I saw the souls of people, it wasn't pleasant and I got out of there as soon as I could. End of story" You weren't telling them the full story but they didn't know that, and you didn't want to tell them. "Do you guys have any money so I could get my own room? I like you guys and I get along with you but I'm not comfortable with sharing a room. They obliged and you were in the room next to them. The first thing you did was take a well needed shower before grabbing a bite to eat and going to sleep.

~~~

The next couple of days were like reliving hell, literally. You were constantly having nightmares about what Hell was like for you. You didn't tell the boys but you had gotten stuck in hell for a couple of months and were tortured. You had managed to recover and your scars were still there but unnoticeable under your clothing.

You couldn't quite remember how you had gotten out but your dreams made that clear. A demon saved you. You didn't know how or why they did so but they saved you and lead you to the exit, knowing which way you came in. You couldn't thank them enough but they simply shook it off as one good deed for the Winchesters, that they will later owe them for. You found that quite amusing.

Sleeping was definitely something you didn't get a lot of. The boys just assumed it was because you were in Purgatory and you never really slept. To be perfectly honest you were tired...of everything. Pretending that everything was alright, lying to the Winchesters, not sleeping, feeling like shit and lots more.

Then, one morning, you decided to come clean and tell at least one of them.

"Dean?" You approached the older Winchester and sat in front of him.

"Yeah?" He looked at you and knew that you wanted to talk about something.

"I...need to come clean about something" You whispered, looking down at your hands.

"Okay? Shoot" He gave you a concerned look.

"When I found the back door to hell...I didn't just find it" You paused to look at Dean who was looking quite confused. "I was captured and tortured for about two months" Deans eyes widened as you questioned "I haven't been sleeping recently as my dreams are full of nightmares of hell"

"H...How did you get out?" Dean asked, cautiously.

"A demon helped me out, they said that it was a good deed that you boys would need to repay someday, who knows when." Dean raised an eyebrow.

"Did this demon give you a name?" He asked, but you shook your head.

"Nope, I would've gotten a name but we were running out of time and I had to leave as soon as possible" you shrugged and Dean pulled you into a bone shattering hug.

"I'm here if you wanna talk about it" Dean said and you smiled, nodding in agreement. Maybe telling him wasn't too bad after all