Death wasn't exactly a foreign concept to the Winchesters.
It seemed that there was an unspoken rule in place that, if you were a child of Mary and John Winchester, death would only last so long (and probably happen more often than it should) before some force of nature brought you back to life. It didn't scare them like it might have in the beginning. They didn't welcome it with open arms, but they didn't go out of their way to avoid it, either.
Even after meeting Death, coming face to face with him and sharing a pizza while Chicago sat on the bring of destruction, He didn't feel like an old friend or a force to be reckoned with. It would be a boldfaced lie to say that Dean Winchester hadn't been scared shitless to sit across from Him, half expecting to drop dead at any second. He'd been handed to Death and brought back more times than he could count, and the idea of dying no longer scared him. But the powerhouse that had been sitting across the table at a Chicago pizzeria... There had been something different there. It was intimidation and respect, not fear, that had brought Dean to his figurative knees in front of Death. It was intimidation that had led him to stammer 'yes' instead of his usual 'yeah', and that same level of intimidation and respect that led him to realize how stupid he had been in his attempt to chain death to his command.
The figure of Death frightened and intimidated him, but the common action of dying had become that awkward friend no one invited to parties, but showed up anyways. The Winchester boys weren't fond of it, but it became necessary to cope with its presence.
Perhaps that was why now, after the apocalypse, the Leviathans, Hell, Purgatory, and everything else his life through at him, Dean wasn't afraid or nervous or anxious. He was forty-three years old now, and his raging alcoholism had given him a serious case of liver cancer. As per his usual stubbornness, he had refused to be stuck in a hospital or try to seek more angelic assistance. "At least I didn't let myself be killed by some monster," he found himself saying. "At least I survived the damn apocalypse."
Once he had been diagnosed, Sam Winchester had attempted to seek out a faith healer, or summon another angel down to help. He knew Dean had threatened Castiel not to do anything, so going to him was pointless. His attempts stopped soon after his older brother found out and exploded.
"I'm fine with it, Sam!" he had yelled, "I've lived long enough- I'm tired. Tired of hunting, of waiting for some fairy tale monster to sneak up on me and finish me off, tired of living."
Sam had stopped trying then. Even Castiel, who had more faith in the Winchesters than anyone else, knew that Dean had accepted the new hand that fate had dealt out to him. It was painful for both of them to watch the once once anointed by God drinking himself away, but they'd be damned if they tried to stop him. Sam was less content with it than Cas, who had sworn to make up his previous actions to Dean in whatever way possible. If letting him slip into the hands of death would do it, then so be it.
There weren't many preparations to be made and, in a way, that was a comfort to all of them, especially to Dean. Baby would go to Sam (he even grudgingly mentioned that he would allow him to 'douche her up'... but only a little). And in all honesty, aside from Sam and Cas themselves, Baby was all he ever had. If he'd had to write up a will, or prepare for larger plans, he wasn't entirely sure he could handle it. A hunter's burial was all he wanted. No service, no funeral parlors, nothing. Just a fire and some salt. Anything else would make it too real- even if he knew he wasn't coming back this time. God, he prayed he wouldn't.
Only half a year had passed since the diagnosis when the cancer took a turn for the worst.
Sam called off any gigs they were looking into for two weeks as Dean slid further and deeper into death's open hands. It was hard for him to watch, and the anxiety of losing his brother made him quick to snap. Dean had caught him pouring glass after glass of whiskey one night, as if to drown out his worries and forget his pain.
"Knock it off, Sammy," Dean snapped at him, pulling the bottle away. "I know I'm not one to talk..." A small smile cracked his lips, "But you better not go down my path. I don't want to run into you up there for another ten years at least."
Sam had, although painfully,agreed. He ended up regretting his promise at the end of the two week period. His older brother had grown sunken and sick looking, confined to his bed most of the time. Bruises had begun to spread like wildfire and his skin had adopted a nasty yellow tint around his eyes. "I'll be seeing Tessa soon..." he mumbled now, eyes closed as he remained still. Castiel remained by his side consistently, calm and quiet. Silently, Sam wondered how much he'd see of the angel after Dean crossed to Heaven. As much as they were friends, Cas's 'profound bond' to Dean could easily pull him away from earth entirely.
His brother's worries were of little concern to Dean now. It was hard, and painful, for him to move even a slight inch. Whenever he opened his eyes, Cas and Sam and the room blurred together. Their presence to him had slowly started to fade.
As their presence slowly disappeared, another one formed. It was his reaper, he knew that, and he relaxed in preparation for the loss of his physical form. The soft shaking that could have been his brother's attempts to stifle his sobs as he coped with his brother's death was barely noticeable. Dean waited to dissolve into nothingness to reappear in his Heaven, a place he had visited numerous times before, even if he only had memory of one trip.
"You are a dramatic one, aren't you."
A familiar, vaguely accented voice jerked Dean's eyes open and his consciousness awake and his body to sit upright. At first, all he saw was black nothingness, but slowly a pale figure began to materialize in front of him.
"Death? Wha- where's Tessa?"
"I gave her the day off," the thin figure replied, dry sarcasm dripping thickly from every word. His long fingers were wrapped loosely around the head of His cane, His head cocked to the side just enough to make Dean feel like he was before the judge, jury, and executioner all at once.
"I thought Tessa was my reaper."
"Yes, you made that perfectly clear." Death shook His head slightly before stepping closer to where Dean was now standing (he didn't remember standing- this was much too surreal). Once He was standing only a few feet in front of the Winchester, Death spoke again. "You're quite the troublesome one for Tessa, Dean, as I'm sure you know. You die more than anyone else my reapers have dealt with. Most only have to escort a soul once."
Dean forced himself to swallow. He'd been assured by Castiel several times that there was a place reserved in Heaven for him, thanks to his stopping the apocalypse, but what if Death had other plans for him while he was in this 'limbo' stage? Some kinda punishment for not staying dead in the past? "So I'm such a pain in the ass that Death Himself had to reap me? Don't I feel all warm and fuzzy inside," he commented with the little quirk of a smile. "So what're you waiting for? Poof me to Heaven or something."
Without so much as cracking a smile, Death inclined His head slightly and fixed Dean with a sharp look, warning him not to be a smartass again. Wisely, Dean shut up.
"It never fails to astound me how brave you are in my presence. I could strike you back into your body and let you suffer until I am ready to reap you," Death replied curtly. "However, that is not my plan. I run a very tight ship, and if I have to return again to reap you, I will not be pleased."
"You still haven't told me why you're here and not doom-and-gloom," Dean commented, still slightly wary.
"I have come," Death began sharply, "Because you are a special case, Dean Winchester. You have surpassed the expectations of God, angels, even many of my own. The apocalypse you initiated, you ended by sheer stupidity and effort. You've locked the Devil back in his cage, destroyed the indestructible Leviathans, fought your way out of Purgatory, and continued to survive for ten years only to finally die of something as trivial as liver cancer. You willingly accepted death after thirteen years of hunting those that go bump in the night. Dean Winchester, to many, you would be considered a freak of nature in your inability to stay dead."
A frown tugged at Dean's lips at the subtle insult, but he wasn't allowed to speak before the thin, intimidating figure continued.
"You have disarmed three of the four horsemen of the apocalypse and still have the nerve to sass Death." For a few moments,there was complete silence between them. Green eyes were locked with all-seeing dark ones. The silence was only broken when Death spoke again, nodding slightly to punctuate His words. "That, Dean, is why I am here in Tessa's place. Someone with a soul like yours, even for an insignificant human, deserves a proper escort to your place in the after life."
The oldest Winchester nearly gaped at what he'd heard. It sounded almost as if Death was complimenting him, albeit in a weird, roundabout kind of way. He'd never thought of reapers as 'escorting' souls before, but when he thought about it, it made more sense than them just plucking up souls and doing nothing with them after. Even in his time acting as a reaper, he hadn't thought about it quite in that way. "Oh," he replied, when he managed to gather his wits about him. "Then, uh..."
"Are you ready to move on? You accepted dying well enough, but are you ready to accept your place in Heaven?"
Dean thought about that for a second- he recalled what he remembered of Heaven, of what it consisted of... but he also remembered Ash, and Pamela, and now Ellen and Jo and Bobby and those who were also already up there, enjoying all the after life had to offer. "Before I say yes, I was uh, wondering about..."
"I know of what you are contemplating. Heaven may not be my domain, but I am capable of certain things. You will have to trust me, Dean. Trust in Death."
Slowly, He extended one thin, boney hand towards Dean. The Winchester swallowed the growing lump in his throat, caused by his nerves and slight apprehension, and extended a hand of his own. As soon as skin touched cold skin, there was a flash of surprisingly warm light that immersed them both and robbed Dean of his sight. The first thing Dean experienced as he crossed into Heaven and the light began to fade was a familiar, warm voice and the sweet smell of a freshly baked apple pie.
"Welcome home, Dean. Your father and I were wondering when you would get here."
