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Okay, so, not that he’ll ever admit it, but Jimmy had absolutely no idea about what he was getting himself into.
None. At all.
Not that he’ll admit that to Amelia or Claire, because he ‘d been so sure when he’d left them.
It’s mostly like sleeping, just a big nothingness. Castiel seems to function better after he’s slept, like even though he didn’t join in he still reaps the effects.
But when he’s awake...
Depending on the situation, it’s like a dream or a nightmare.
Wandering around with the Winchesters, trying to stop the Apocalypse on a day-to-day level?
Dream. Weird dream, but dream.
Getting shot and stabbed, torturing, all that jazz?
Nightmare.
So when Castiel gets pulled back for “re-indoctrination” (whatever the fuck that means), Jimmy takes the opportunity to run like the wind.
And he almost makes it, too.
But then they get Amelia, and Jimmy is starting to realize why those morons didn’t want him to go back, and he screams at Castiel.
It feels good, but not good enough that he forgives himself for letting this happen in the first place.
And then Castiel, that son of a bitch, takes Claire. And Jimmy knows it’s consensual, Castiel’s an angel after all, but there’s something about that that alternately makes him want to cry and go buy a shotgun he can clean menacingly.
So he agrees to be Castiel’s vessel again. And life goes on without his wife and daughter.
~
He tends to sleep more, after that, occasionally waking up when Castiel assures him that there isn’t any violence.
He screams at Castiel when he listens to Zachariah and tries to turn the Winchesters against each other (because they might not be the brightest crayons in the pack, but they grow on you) and breaths when Cas agrees to help. He laughs when Cas gets confused about things that Jimmy takes for granted, more for the looks on the Winchester’s faces when they try to explain.
~
They get killed by Raphael. It’s hell. Well, not, it’s not, but-
You know what he means.
And then they’re brought back, and Jimmy really doesn’t want to do that again. There’d been a sickening moment when he felt like he was about to fall away, and he’d only held on by the skin of his teeth.
There’s the time where Cas finally (finally) eats, and eats, and eats, and eats till Jimmy never wants to eat again.
They save people, and Jimmy watches as it goes past. He recognizes the looks Dean starts giving Cas; they’re the same ones Amelia used to give him. He watches and waits.
~
Cas, Bobby, and Jimmy follow Dean to the graveyard with Sam and Adam and Lucifer and Michael.
And Lucifer kills Jimmy and Cas.
This time, Jimmy lets go.