Summary: Five times Dean Winchester ran into Damon Salvatore. Monsters and monsters don't mix, except when they do. Dean's about to go to hell, but Damon Salvatore is gonna make it one hell of a ride.

Notes: I started this story for a dark fest years ago, to the prompts
Any fandom, any pairing, Tonight, I don't feel sorry.
Any Fandom, Any pairing, "I could touch you and you wouldn't even feel me. You don't even know the danger you're facing. If I'm quiet, I'll slide up behind you and if you hear me I'll enjoy trying to find you.", any kink
I got stuck midway through and went with a different story for dark fest, then abandoned it altogether when I remained stuck. Now, years later, I've decided to dig it out and finally finish it. Hopefully it's been worth the wait!

Playing loose with timelines here, let's all pretend Supernatural season 3 and TVD season 1 take place in the same year.

The Fifth Time

Prologue: The Fifth Time

"Yes."

Damon started almost imperceptibly and swivelled his head fully around to meet Dean's eyes, mouth opening for what was undoubtedly some infuriating smartass quip.

Dean didn't give him the chance to voice it. "Yes," he repeated firmly. Again, Damon opened his mouth and again, he cut him short. "The answer to the question you've been dying to ask since day one." He smacked his glass onto the table, mindless of the whiskey sloshing over the rim, and stood up. "It's yes."

Damon remained glued to his seat, still frozen in the same lazy, cocky body language he had had before Dean caught him off guard. He gave a snort of laughter, emptied his glass of bourbon in one swig and pointed an accusing finger at Dean. "You are drunk!"

Dean snorted. If Damon wanted to play hard-to-get, he could find himself another playmate. He threw a bill onto the table and walked towards the door without so much as another glance at Damon.

The door banged shut behind Dean as he stepped onto the parking lot. His eyelids fluttered shut as he inhaled deeply. The night air was pleasantly cool and fresh after the smoky air in the bar, just cold enough to clear his not quite drunk, just a bit fuzzy head.

There was the faintest disruption of air to Dean's left.

Dean's eyes opened to calmly meet Damon's pale blue gaze. He smiled his best butter-wouldn't-melt-on-his-tongue smile. "Hello Damon. Fancy meeting you here."

Damon snarled and in the very same moment already, Dean found himself grabbed with supernatural speed and thrown against the brick wall of the bar. Before he could so much as find his footing, Damon was already upon him, hands pinning his upper arms to the stone, lean body pressing into his so firmly he could feel the contour of every brick, Damon's belt buckle pressing into his stomach, his hard cock nudging against Dean's groin.

"Why?"

Dad had once told him, when you're meeting a predator's eyes, don't look away unless it's part of your plan. Whoever looks away first submits.

Dean didn't look away. Not even when Damon's eyes turned ugly, dark veins surrounding them like spider webs. At any other time, he would have recoiled in disgust when Damon showed himself as the monster he was. Not tonight. He ignored the revolted churning of his stomach, took the whispers of 'what would Dad think of you?' and 'what would Sammy say?' and crammed them into the same nasty back corner of his mind he had filled with so many what ifs ever since he made the deal.

"Because I've got two weeks left to live and you're on my to-do list."