Everlasting Affinity

Chapter One: Highway to Hell

Dean knew there was nothing he could possibly do to get out of his demonic contract he had made exactly one year ago today. He had already come to terms with the outcome of the deal not long after he made it, since his Sammy would still be alive, even if Dean wasn't around to see it anymore. His soul was a small price to pay for the last person Dean ever truly loved to live on. He only went along with finding a way out of the deal to please Sam, and bring him closure on the matter. Dean was going to die. Hell was knocking on his doorstep, not bothering to be asked for an invite inside. Dean wasn't afraid though. No hunter ever had a happily ever after. But it gave Dean peace knowing his brother had a chance to be happy again. To resume life without his older brother, who had dragged him down once he stepped back into Sam's life that night that Dean snuck into Sam's apartment. An eternity in hell was what Dean deserved for tearing Sam away from his normal, happy life.

When Sam had died, Dean felt that he had too. Sam was the reason he breathed, the reason he kept fighting on. With both of his parents dead, and no wife or children, Dean couldn't think of any other reason to really be alive. Sam was his world from the moment he was born. He always looked up to Sam. Figuratively and now, literally. His little brother has grown up so much, so very fast. Part of Dean missed his sweet innocent brother before he had found Dad's journal when he left it once before he went on a "job", leaving Dean to explain that the monster under the bed was usually so much worse than a bedtime story. Dean hated the fact that Sammy had to grow up just like Dean had. It was no life for a child. In fact, there was no time to be a child. Once you knew what was really in the dark, you never got to turn away from it. All Dean has ever wanted for Sam was for him to be happy.

Dean prayed that Sammy let him go once he got dragged down under. He hoped he would find peace and go find a girl and fall in love. He wanted Sam to go get married and have a bunch of rugrats with a mop of brown hair on their heads, just like their father. The thought of Sam living the apple pie life, the one that Dean used to make fun of Sam for wanting, is where his happy place resided.

Truth be told, Dean was tired of this life. Saving people, hunting things. The family business. Dean always lived by this, but lately he could see how much bullshit it really was. Sure, they saved a few people, but everywhere they went they also left behind so much pain and lose that Dean questioned if it was even worth it at times. The people that the brother's couldn't save, the ones who right under their noses, just barely out of reach, are what haunted Dean at night. It weighed him down like an anchor tied to his ankle that was sucking him down into an endless abyss of pain and sorrow. Deeper and deeper, it took him – case after case – and as the bottom of the trench neared, Dean knew he was ready for it to let it swallow him. He would be able to let go of it all. The guilt of making Sam miserable with him in the life of a hunter, all the families that visiting him in his nightmares that he had failed, the gripping pain of knowing he would never see his mother again and say that he loved her one last time.. All this would be gone once Dean was. Bobby would be able to take it easy for a bit, without the Winchesters constantly asking for favors. Dean welcomed hell when he thought about all this being lifted from his shoulders.

Bobby and Sam were all Dean had anymore, and Dean was emotionally so sick and tired of pulling them down and letting them down. They both had gotten very little sleep as they neared the date of Dean's deliverance to hell. They were on to something, they thought, that would get Dean out of his contract. If it didn't work and this would finally come to end, they would be able to rest. Dean almost smiled at the thought of it. The two people he loved more than anyone, Bobby being more of a father than he had ever actually had, would be so much better off without the presence of the older Winchester boy. It was like a knife in his chest realizing this. Dean ruined everything he touched but he would no longer have to worry about that after tonight.

Dean had told them over and over again to stop looking for a way out, because there simply wasn't one. Maybe Dean just didn't want to be saved.. If Dean did survive the night, he wasn't sure he could live with himself with all the thoughts that have been buzzing around in his head since he made the deal. Guilt tore him from the inside and it threatened to finish him off before the hellhounds would have a chance to.. But he had to try and go along with Sam and Bobby's plan because if the tables were turned, Dean wouldn't rest until he found a way to save Sam or Bobby from the fiery pit. Even though, Dean just wanted to lie down and take what he had coming for him, he pretended to believe that they could have him soul tonight. For their sake, it was the least Dean could do for them.

Dean always pictured himself going down guns blazing. He wanted his die doing the thing he was best at. Hunting. He was okay with the fact that he might never return from a job, or an exorcism. That was his life. He was supposed to die fighting, hopefully taking whatever killed him with it. This was never how Dean pictured the end, but then again, life was never going the way he planned for it to go. It surprised him just how willing he was to let his body get ripped into without so much as a shot fired. But Dean was ready to do just that if Sam would allow him to. That wasn't happening though.

Dean had wanted to spend his last couple of weeks with a bottle of whiskey in hand and buried in women until the darkness took him. He wanted to enjoy the last few weeks to the best of his ability in a drunken and lustful stupor before he became a play toy for the ugly bastards downstairs. Booze and women were easy for Dean. The haziness the alcohol gave him and the pure human instinct to find what pleasure he could in a woman's body was simple and Dean understood it perfectly. It would allow the time to flow easily and allow him to bury his emotions until he bowed out for good. What Dean didn't get was how to deal with the guilt that ate at him when it came to the situation at hand. So he wanted to forget about it until time ran out.

But instead, Dean was with Bobby, Sam, and his little brother's demon whore, Ruby, trying one last time to save Dean's soul from everlasting torture. They were plotting to kill the powerful demon that held Dean's contract named Lilith. She was rumored to be the very first demon and whenever she was spoken about, it was with fear and respect. Dean only had maybe an hour left, maybe less, before the hounds came after him and the hallucinations had already begun. Dean knew they had no hope of killing the contract holder. He only wished that Sam and Bobby remained unharmed in this fight and Dean could leave this world without having to worry about if they were safe or not. '

Sam and Dean stood in the house of the family that Lilith had been tormenting for months. The beautiful home was now littered with debris and smelled so much of sulfur that Dean almost gagged. A large godfather clock began to pound at their eardrums, like a death sentence being repeated over and over again. Dean had no time left. It was midnight and he was going to die. He glanced over at Sam with a look of reassurance and tried his best to shoot Sam a calming smile. I'm ready for this, Sammy. I have been for a while. A single tear fell from Dean's cheek. Sam stared back as he nearly choked back a sob and he mouthed back no. Sam's expression ripped Dean's heart out at that second and he just wanted to reach out and comfort his younger brother one last time. Even if he didn't need it anymore.

The moment was ruined by Ruby ripping open the barricaded door with a smug look on her face and Dean knew instantly it wasn't Ruby in that meatsuit anymore. Her eyes glowed white and she walked with a cockiness Dean instantly despised. Of course the bitch would possess the old vessel of a demon he already hated. She gazed at him triumphantly. "Hello, Dean."

She had a predatory look in her stark white eyes as she sized up the older Winchester. The barking laugh made Dean cringe. "Dean Winchester. Just moments from his deathbed and not even fearful. What an honor to witness. Yet how typical. You Winchesters never did value your pathetic little lives. Always throwing them away for the lesser good." Her smirk then turned to Sam, who was frozen beside Dean.

Sam's eyes were focused on the blonde demon ahead of him, and Dean could see how tightly his jaw was clenched. Like a cat swatting at a ball of yarn, Lilith cast Sam aside and he slammed into a large bookcase that threatened to fall on top of him. Dean snarled for her to leave Sam out of this. This wasn't his fight. Her glare was like daggers as she slammed Dean into the small table in the room and pinned him there without lifting a finger. Ruby's knife slipped from Dean's grasp and fell uselessly to the floor. Dean didn't want Lilith to be the last image in his head when he died, so he focused on Sam at the same moment she turned her attention to him as well. She let out a snarling laugh and seemed to pet the air beside her.

"Sick him boys." Her voice rang out and then all Dean could hear was the howls and sounds of his clothes and flesh being torn apart. He screams where inhuman and something he didn't recognize, but he refused to tear his gaze away from his baby brother, even as he could feel claws digging deep inside his chest and consciousness threatened to take him. Even the deep gashes that streaked red across his flesh couldn't compare the pain in his gut from the look on Sam's face. He looked lost and hopeless. He was powerless to help the man who gave him everything.

Even now, with Lilith looking at Sam like he was something to eat and Dean was being gutted, Dean wanted to protect Sam. Dean lived his whole life making sure Sam was safe, and he would never be able to do that again. The fact that Sam had to watch his older brother - who was always so strong and did so much for them - die like this shattered Dean into a million pieces. He didn't want Sam to see him like this. He didn't want this to be what Sam remembered last about him. Meeting Sam's bloodshot eyes, Dean could see the pain in them as he watched helplessly.

Lilith took pride in her work and the pain radiating from both of the boys brought her so much joy, she almost smiled. She was tearing them both apart, and one of them, she didn't even have to touch. "Your turn, kiddo." She attempted to use her demon powers on Sam, to kill him instantly, but Sam was so full of anger and grief that it had no effect on him. Sam realized this and through his tears, he glowered at the demon.

"You can't hurt me, you bitch." Sam was reaching for the demon blade and in an instant; Lilith came gushing out of Ruby's old vessel in a thick black smoke. Dean closed his eyes at that moment. Sam would be okay. He was more than capable now to protect himself. His screams died down as he let the hounds take him and he vaguely heard Sam shout his name over and over again. One last smile rested on his lips, just for Sam, and the dark closed around Dean for good.

His family would be safe. Bobby and Sam would move on.

Safe.

From Lilith. From Ruby. From Dean.

******* Author's Notes *******

This chapter isn't my favorite but I PROMISE the next is so much better, if you could get through this chapter, I encourage you to continue on. The story line will drastically change once Dean meets Castiel in the next couple of chapters. Longer chapters are to come also! This was kind of a prologue! Please review and let me know what you think. Thank you for reading!