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Ever since he could remember, Dean had always been taught to not solicit with demons. His only interaction with them should be when he sent them straight back to where they came from. His dad had drilled that into him, so much so, just waiting here on a crossroads made Dean feel uneasy.
But he waited nonetheless.
He waited on Crowley, the demon King of Hell. Dean would have waited forever if he could, but he didn't have the time, (Y/N) didn't have the time. She had been cursed, some witch, or something else Dean didn't even want to begin to imagine, had cursed her. Her organs were slowly shutting down, soon she wouldn't be able to breathe and then her heart would stop beating.
Human medications didn't work. There was no spell or antidote that either of the Winchester boys could think of either. Castiel had exhausted his Grace trying to heal her, but it was for naught. Nothing they tried seemed to take at all.
So Dean waited at the crossroads, with only his soul to sell. He knew it wouldn't take long for Crowley to show, and he was right. With his flair for dramatics, he appeared on the other side of the road at exactly three a.m.
"Dean Winchester, what a surprise." Crowley, dressed in a characteristically dark suit, stalked across the road until he was face to face with Dean. "To what do I owe the pleasure?"
"You know why I'm here." Dean spat out.
"I do... I just want to hear you say it."
Dean took a breath to steady himself. There was still a small part of him screaming to run away, to not bargain away what little he had left. But it was (Y/N) and he wouldn't let anything happen to her. "I need you to save her, (Y/N). She's going to die and you need to stop it. I'll take my ten years and then you can play house with my soul for all eternity."
Crowley hummed in thought, moving forward so that he was in Dean's personal space. He waited a moment before responding. "No deal."
"What!? Why not?"
"Ten years is a long time, I just can't wait that long before I get my hands on the elusive Dean Winchester's mortal soul."
"Five years." He offered, desperate for anything at this point.
Crowley pretended to consider his offer, but shook his head after a moment. "One."
One year.
Dean would only have one year left to live. There would only be one more birthday, Christmas, Thanksgiving. Just one more. But it would mean that (Y/N) would get the birthdays, Christmases, Thanksgivings that she deserved. She would get to live.
"Deal."