Story Title: Prison Ties

Rating: M

Disclaimer: I don't own any of these shows or characters. I'd appreciate not being sued. Thanks.

Pairings: Dean Winchester/Nate Archibald, Mason Lockwood/Damon Salvatore (with occasional Dean/Mason & Nate/Damon as well)

Summary: Without their usual friend posses backing them up, Dean, Damon, and Nate's crazy antics finally land them in the slammer. How will they adjust to life in the Big House?

A/N: Okay so in case the pairings part didn't tip you off, this is not just a Supernatural/Vampire Diaries crossover. There's also Gossip Girl mixed up in there. Why? Because I think its a great idea. For Supernatural this is set towards the end of 'Swan's Song'. For Vampire Diaries it takes place after "The Return" Mason never comes to Mystic Falls though. For Gossip Girl this is set half way through 'Last Tango, Then Paris' before Chuck leaves. After that everything's pretty much AU. I think that's right. Let me know if there are any huge inconsistencies. This is my first crossover fic, and its the first fic I've ever published. I hope someone enjoys it besides me. Sorry if the first chapter is kinda slow. I'm afraid it doesn't really heat up until all the characters actually get to prison.

Chapter One

How Dean Met Mason

Dean was parked on a smooth suburban street in Indiana, brow furrowed, lips pursed, glazed over eyes fixed on the little blue house with white shutters. He had pictured himself walking up the front porch and knocking on the door a hundred times over in his head. Lisa would open it holding Ben in her arms. It would be perfect. Well as perfect as life could get given his past… But dean couldn't think about the past right now. Or ever. If he did he would completely fall apart.

He had to do this. He wanted to do this.. Dean had promised Sam that he would lead a happy life. He tried to think positive. He was gunna be a family man now. No more hunting, no more drinking, no more guns. He was gunna walk through that door to that woman and that little boy and never look back. Yep, it would be all backyard BBQS and little league baseball games from now on. He would be happy here. Safe, normal. The life he'd always wanted. He had been sitting there for almost an hour now, and his hands were still gripped tightly to steering wheel. He loosened his grip. Damn it! What the fuck was wrong with him? He let out a long breath he hadn't realized he'd been holding.

He wasn't ready.

Oh, Dean would keep his promise to Sammy if it killed him. But it wasn't right for him to go in there with all this emotional baggage. He sighed. Dean hated dealing with emotions. But he needed to come to terms with the past before he could move on. He needed to fall the fuck apart. He'd be back in a day or two perfectly ready to accept his new life.

He turned on the engine and just started driving. Within minutes he was thundering down the highway. He didn't know which highway and he didn't care. He pulled off once for some gas and some alcohol, then continued on his way. He didn't want to know where he was going.

Sometime in the middle of the night dean pulled into a driveway in the middle of nowhere leading up to an old abandoned shack. Dean parked his car and rested his head against the dashboard, one hand covering his eyes. He felt shudders start to take over his body. "Sammy…" he croaked out. He pushed the shudders back down, sat up and sniffed. He looked at his car stereo, it was blurry through his tear coated eyelashes. He turned it on and cranked it up as loud as it would go. The sound of his own voice made him sick. He got out of the car, opened the trunk and pulled one of the fifths of alcohol he'd bought. He started chugging until he thought he would vomit. He looked down at the trunk of his car. It was still filled with all his hunting gear, like nothing had changed. He poured a copious amount of alcohol into the trunk and pulled out his lighter. But he just couldn't bring himself to torch his baby.

"Fuuuuuckk!" Dean hurled the bottle at the old shack and it exploded on the door. He looked at the still lit lighter in his hand and threw it at the liquor soaked door, which immediately caught fire. He grabbed another bottle out of his trunk and started drinking again staring for god knows how long at the rapidly growing fire in the shack in silence. Then suddenly he was yelling.

"You took everything I ever loved from me, damn it! Everything! Why? Why'd it have to be our family? Why'd it have to be us. Why are we the ones who have to give up everything?" The yells were coming in between sobs now. Dean didn't know who he was yelling at. Fate? The devil? God? But it was the shack he was directing his voice at, as if it had some how wronged him. He slid down the front of the car and let his sobbing consume him. It was okay, he couldn't hear himself over the music.

Dean saw something move out of the corner of his eye. He jumped turning to see what it was. His unfocused gaze was met by a police officer pointing a gun at him. His car radio clicked off suddenly. Dean turned to look at his car bewildered. There were four squad cars parked behind his Chevy Impala and 6 other officers standing in the driveway examining the contents of his trunk. Apparently his sobbing wasn't the only sound being drowned out by his radio. He could now hear what sounded like a fire siren in the distance.

"I said get down on the ground, boy!" the officer holding the gun yelled from behind him. One of the officers in the driveway was looking through his box full of fake Ids. Dean knew there were fake FBI badges in there as well. "oh god…' moaned dean.

"now!" yelled the officer. Dean couldn't see a way out of this. He turned over on to his stomach and put his hands behind his head. Shit!

Three days later and Dean was being led down a prison corridor by two guards towards the cell that would be his home for the next year and a half. So much for being back with Lisa in a day or two. He could have drawn the process out. He could have asked for a lawyer, fought in court for a lesser sentence. But Dean knew he was guilty, and the last thing he needed was people looking into his past. If that happened he'd be in here for life. He felt he got off really easy all things considered. And if he stayed out of trouble maybe he could get out sooner.

"We got a nice roomy cell for you." said the guard to his left. "Only one cell mate, heh!"

"Oh, lucky me!" dean chimed sarcastically. The other guard elbowed him in the side.

"So you think you're tough, huh?" the guard chided. "Well lets see what you make of your new roomy, you little shit." they had arrived at one of the cells at the end of the hall. He stood facing a blue solid iron door with one tiny bullet proof glass window in it. Well, Dean thought, at least while he was in this iron prison he wouldn't have to worry about the things that went bump in the night. One of the guards unlocked the door by punching a code into a panel next to the door. The door slid open with a clank. There were two concrete beds stacked on top of each other like bunk beds on either side of the cell. On the top right bunk Dean could see a mass under a crappy prison blanket.

"Hey beast, wake up!" one of the guards barked.

Dean rolled his eyes and smirked. Beast? Please! What was this Xmen? The thing under the blanket let out a deep, rumbling dismissive growl. Dean tried to jump back. "You gotta be fucking kidding me!" he said under his breath. That had not been a human sound…

"We got a nice new playmate for you big buddy!" Dean found himself being unceremoniously thrust into the cell. The door slid closed behind him. And he could hear the guards laughing their way back down the hallway. "Dicks!" Dean yelled after them. The thing under the blanket stirred, and Dean backed up against the opposite pair of bunks. The blanket flew back and Dean got his first view of his new cellmate. He relaxed a little. The shirtless man sat up, rustling his cropped black curls with one hand. He was definitely big, and clearly enjoyed working out, but he was just a man. He was staring at Dean with fierce squinty hazel eyes that were almost yellow. There was no humor on his face. He looked sleepy, but like he was still clearly sizing Dean up. It looked like he couldn't decide if he was going to ignore him and go back to sleep or lunge at him in a violent fury for invading his territory. There was definitely something beast like about the guy. He looked a bit like a large jungle cat or something. Dean found out just how large when the man jumped down from his bunk in one swift movement, landing barefoot in front of Dean with a resounding heavy thud.

"Jesus!" Dean exclaimed pulling a face. He really didn't fancy the thought of having to fight this guy. But he reminded himself that he'd fought tougher. The man stared down at him with a stony calculating glare for a few silent seconds, before his face burst into a gap toothed smile. This wasn't a friendly smile. Dean knew this smile. He'd made it countless times at the many woman he'd come across in his life. It was the smile of a predator closing in. 'Oh dear God no!' Dean thought. He just couldn't catch a break! Of course his new cellmate had to be a Butt Pirate!

"Damn, its my lucky day! You're a cute little fucker!" the man chuckled. Dean's eyes were like saucers. He felt his ass involuntarily clench up. Why was this happening to him?

"Look, dude. Its nothing personal. Its just the way things work in here. So don't look so pouty. You'll get use to it." the man was mocking him. "And if your nice I'll go easy on you. We could get along real good you and me." he reached out to touch Dean's face. Dean slapped his hand away and punched him in the jaw. Enough was enough. Dean had faced Lucifer himself not so long ago. He hadn't been to Hell and back again just to end up this faggot's boy toy! He jabbed the man in the chest with one finger, his other hand was covering his ass protectively.

"Look here, Beast or whatever your name is." he started.

"The name's Mason." the man cut him off. He was leaning up against his bunk with his arms crossed looking disinterested.

"Well, Mason. Lets get one thing straight. I don't know or care how things work in here. I'm here to serve my time and get the fuck out. And if you think I'm gunna be your little Butt Monkey while I'm here, you've got another thing coming!"

Mason chuckled. Dean barely had time to register the pain of Mason's massive fist hitting the side of his face or his head hitting the hard concrete floor before he was out cold.

I'm afraid that's it for the first chapter. I promise the next one is coming soon and will be longer and more exciting! Please R&R!