What's crazy, is that Castiel actually asked him permission and what's even crazier is that Jimmy said yes. Fine, there was no sense saying no, after all he was the one giving Castiel his body out of free will of sorts, so it kind of went unsaid that Castiel could do whatever he wanted with it; also, since Castiel was back, Jimmy is there a lot more, like Castiel actually doesn't want him shut out and he feels everything that goes through Castiel's head. If you can call it like that.
So Jimmy knows. Jimmy knows exactly what Castiel feels for Dean, actually he knew before Castiel did because hey, Jimmy is the human one in there and he can recognize emotions, thank you very much. Jimmy had felt Castiel's utter desperation when Dean had said they were done, he had felt the guilt, he had felt his internal conflict, he had felt everything; now they're all on the run, Dean, Sam, Chuck and them, and things are so fragile and the end is so near that when it came up that Dean actually reciprocated Castiel's feelings too... well, saying no when Castiel asked would have been plainly cruel. It's not like Jimmy has much hope of happiness for himself again, but he never was a vindicative man nor what Dean would call a bastard son of a bitch and if he can't have it, he won't deny it to others if it's in his power.
(And that's pretty much the only thing that is in his power, these days.)
And then, then, after the first time, Jimmy realized that he needs it too even if he really isn't a part of the equation. Jimmy is a mean from Castiel to Dean and vice versa, but he doesn't really play any other part. He feels what Castiel feels even if it's not as intense and Christ, he will never get adjusted to be there inside his own body and be able to just watch while someone else controls it in his place.
But it doesn't matter because pitiful as it might sound, Jimmy craves it. He craves that moment every evening when the sun sets for what might be the last time and Dean turns off the light; he craves it both when Dean and Castiel take things slow, touching each other with a reverence on both sides which Jimmy would have imagined in Castiel's case but not in Dean's. He craves it when they kiss without hurry, he craves it when they undress each other and Dean trails kisses all over Castiel's shoulders, he craves it when Castiel is inside Dean and holds Dean's hips like he's made of some precious glass, he craves it when Dean looks up at Castiel (at them) with those eyes that say every word his mouth won't pronounce. This usually happens when it was a decent day.
He craves it when the day, on the contrary, is filled with blood and black smoke and the second they are into whatever room they find the clothes get almost ripped off, there's no time for sweet talk, they kiss so hard that blood is drawn and then Dean fucks Castiel (them) with such an intensity that Jimmy has blacked out more than once.
Jimmy craves it because while with Amelia it always was the first case and never the second, what they have is everything he doesn't and won't probably have anymore, and they have it only because of him; knowing this makes him feel strange, almost dizzy, because while he's technically powerless, he really is not. Even if the world becomes a worse place with every day that passes and they still don't have a plan to stop its ending, when the door closes Dean and Castiel are... happy, or sort of, or as close to happy as one might be in these circumstances, and Jimmy knows how miserable Castiel had been before. More or less since he came back until Dean kissed him for the first time.
They have this and it makes them strong, it gives them what they need, it saves them from a good deal of misery; but Jimmy is the only reason it can happen, and that's why sometimes he allows himself to blank out just a bit and imagine that the hands cradling his face are Amelia's even if they are wider and rougher; some other times, when Castiel's feelings are so overwhelming that he can barely keep them in check, Jimmy is there, goes with it, blanks out and pretends they're his, too; all the times, he's there. After all, it didn't take much to find out how easy it was to pretend that he's an active part in all of this, but he needs those sparse glimpses of happiness for himself too much to care.
End.
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