He had never believed he would live so long, and now he has, he's not sure what to do. He hasn't lived all that long, not really, not by normal standards. Hell, he even knows quite a few hunters who outlived him. … His Dad, Bobby, Samuel before he got possessed and turned them all into Crowley's bitches. But, they died in battle and … he was out of the fight.

He'd expected to go out in a blaze of glory. If he was going to be catastrophically injured, it was going to be epic.
A wendigo would rake him open with his claws, skewered one of his kidneys and leave him in bad shape. He'd take his dialysis machine around with him, sleep in the car grey faced and puffy until Sam came and gave him a transplant and they went on with their lives, one kidney short.
He'd break his back falling down three flights of stairs. It would be hard, but he'd keep hunting because he doesn't know what else to do or be so gorked out of his head that when he retires, he can't do anything but sit and drool.
He would die facing Yellow Eyes, take the demon out whatever the cost.
He would die when the cross roads demon came, and it would end quickly.
He'd die in a fire. Not a routine salt-and-burn, one started by holy oil and designed to keep his angel-possessed ass under control. Or in that epic battle with Sammy-come-Lucifer.
He'll take a bullet for Lisa and Ben.
Hell, he'd even have taken a massive four or five car pile up on the interstate. Something that totaled his baby and left him smashed to a pulp.

A hunter went in a big way. He did not slowly fade away until the salt he regularly handled was saline solution and the only demon he regularly fought was pain. A hunter died on the job. A civilian died at home in bed.

The truth was that he'd been fighting this for so long already.

He vaguely remembers what it was like to be without pain. It happened once or twice when he was a small child. Those days when he could curl up into just the right position on the lumpy, hard, hotel mattress and the pain in his back would go away. The times that his hips didn't feel like they were on fire. And then, there was the time that he came back from Hell and his body was new again. New and Clean and Quiet. He doesn't know if Castiel fixed the damage that was there, or just paused the progression for a while.

The pain came back as they fought the break of the seals, and then fought he apocalypse and searched for Sam's soul. By the time Raphael sucked them into his war in Heaven, Dean's body was back to its old tricks.

Sammy, of course, was oblivious. He had trouble hiding his addiction, but he had trouble seeing his brother's pain. Or, maybe Dean had just lived with pain for so long that Sammy didn't remember anything else. Watching something happen from the time you're six makes it feel normal. Something else would be wrong.
There's a morning where he wakes up cold and naked, slightly hung over and sprawled across the bed. He spends most nights drunk, because when he's drunk his back doesn't ache like someone shoved a piece of rebar in his spine and his hips don't feel like he's breaking cement. Of course, when he's hung over, everything is worse. It's memorable because it's the morning that he stops being able to get out of bed. He cannot bend. He cannot stretch. He is immobile.
Sam drives him to the hospital, Cas hovering and looking guilty.

The diagnosis is swift, and clear cut. He meets almost all the criteria. They wonder why he hasn't heard the words already. It's a wonder that he's still walking at all. It's a wonder he can still run, still fight, still function.

The doctors don't know hunters, though. They function and fight and crawl when they can't run anymore because they're too darn stupid to do anything else.

They tried to hunt, tried to keep going. But, it's hard to hunt when your body won't listen and your hips hurt and all you want to do is sleep.

Fate is a capricious bitch. He won't die; he'll live a long, painful life. He can't hunt anymore. He can't work a physical job. And, there isn't much for a high school drop out whose only talents are cleaning guns, surviving the apocalypse, and hunting ghosts.

He always thought he'd go out in a blaze of glory, and not remain a sputtering candle. Alistair's torture in hell has nothing on this.