6 Months Later…
Sam had him, he had finally caught Dean. After months of research and tracking he finally had a way to fix his brother.
But he hadn't had any luck finding you.
Sam had discovered that there was a Men of Letters experiment were they tried to cure a demon, now he had no idea if this worked, they had tried once before. But that didn't end to well for anyone. He walked into the dungeon where they had Dean secured to a chair, in the middle of a devil's trap, with cuffs engraved with special symbols that hinder his powers.
"Morning Sammy," Dean says as Sam walks in the room. He doesn't say a word, he just goes right over to the table with the syringe and collects Dean's dose of purified blood for the morning.
"Sammy, how do you know this isn't just killing your brother in here," He asks
"I don't know," Sam starts. He wanders over to Dean and plunges the syringe into his brother's arm.
"But we need to try," Sam says as Dean lets out a blood-curdling scream.
"Fucking Bitch," He grunts. Sam removes the syringe and walks back to the table to sterilize it.
"You find her yet, my bitch of a girlfriend," Dean asks in a sarcastic tone.
Sam huffs in discouragement. He's gripping the edges of the table trying to calm his anger. He wasn't angry with you, he was angry with himself for leaving you alone, so you could run away and go off the grid. In a fit of frustration, Sam shoves the table away from him and storms out of the room, slamming the dungeon door behind him, while Dean chuckles to himself.
Little did he know, you've had the worst past six months of your life…
Right after Sam had dropped you off at that motel six months ago you had been studying demons, and possession day in and day out. Until you knew almost everything. That was your plan, find one of Dean's demon buddies and make him an offer he couldn't refuse.
5 months ago….
You were waiting at the meetup spot, in the back alley of one of the bars Dean frequented. You had been waiting for half an hour and were about to bail when he appeared from around the corner.
"Y/n? Y/n Y/l/n," he questioned. "Never thought I would hear from the one and only Dean Winchesters side piece," You try to hold back your anger at the nickname.
"What do you want?" he asks.
"I wanna make a deal," you state.
"Really? What kinda deal," he inquires.
"I want you to help Sam get Dean to come home," you say "help him by dropping hints of his location over angel radio, so Cas and Sam can find him,"
"I might be able to do that… What would you give me in return?" he says with a smirk
"I'll do anything you want, just please help me," the longer this conversation goes on the harder you find it to hold back your emotions.
"Here's my proposal," he says. "When Sam gets Dean home, I'll come back and ask you for a favor, if you deny I will get Dean to kill Sam in front of you, how's that sound?" He asks.
"Okay," you blurt out before you have a chance to think it over.
"Great, let's seal that with a…" he says smirking in your direction because he knows you know what he means. You lean in and press a kiss to his slimy lips, he holds your head there for a minute, as if he's savoring the moment.
When he releases you he vanishes, and you are left alone in the dark alley to think about the decision you just made.
Present-day
You were sitting in your motel room, knowing that your inevitable fate was on its way. You can feel an immense weight on your shoulders, walking over to the mirror you looked at your disheveled appearance, you hadn't brushed your hair and generally didn't care about yourself, and then he appears, laying in your bed.
"Hey Sweetheart, you look… great," he says sarcastically.
"Is he home? is my Dean home?" you ask, still looking at your reflection in the mirror.
"Yes, now it's time to settle your end of the bill,"
"What do you want," you say coldly.
"I just wanna… borrow that beautiful body of yours to do my bidding," he says with a seductive growl which makes you want to throw up.
"How long?" you mumble. "What darling?" he starts. "Say that again,"
"How long do you want me for?" you spoke up.
He took a moment to think, staring at you through the mirror. His hand settled under his chin in thought.
"Well, I've done five months of work for you… and in demon years one is actually ten years, so I say in demon years five…" you had lost track of his words when he started getting into years. It would be years before you ever saw Dean again, that is... if he even wanted to see you. Sam had no idea what you had done while off the grid, and what was he supposed to tell dean when he cured him. This might be your life now.
"Five years oughta do the trick, what do you say?" his voice brings you back to reality.
"Fine," you say and you rush over pressing a quick kiss to his vessels lips to seal the deal as quickly as possible.
"So eager are we, but there's one problem," he says pointing at your chest. You pull the neck of your shirt down to reveal the anti-possession tattoo Dean made you get for protection.
"We need to do something about that mark, you gotta knife?" he asks.
You rush over to your duffle bag and pull out a switchblade. You had it to him and he wastes no time in cutting a slit through the symbol. One tear slips your eye and he gingerly raises his thumb to your cheek yo wipe it away.
"Now this might hurt," he says before you see the black cloud of smoke exit the old vessel and enter you, and your world goes black.
"It's warm in here," you can hear the demon clear as day. Like the talking through speakers in your brain.
"I'm going to have so much fun with you," he growls.
That's when your nightmares begin.
3 years later…
Sam and Dean had been looking for you for years before they were given a tip from a hunter that they saw you in a diner north of Colorado. The minute they heard this they jumped in the impala and raced to get you. You were taken completely off guard and fought your hardest to get out of the cuffs but it was no use. They finally had you. You could see everything that was happening from inside the cage he trapped you in, knowing you couldn't get out until your contract was up.