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He thinks that Cas knows sometimes. When he says makes a comment about the ways he used to take care of Sammy and Cas freezes, then looks at him like… well Dean doesn’t know what the look is, but it makes him feel bare; barer than he ever did on the nights he used to go out just desperate enough for something, anything to put on the table for Sam.
He’d find it too, learned quick enough where to find the men who would take him home, use him, and then give him a twenty and a pat on the head for his troubles. It made him sick, still makes him sick to even think about and he tries not to. Tries not to think about it but it’s always there in the back of his head, like a recording on loop that he can’t figure out how to turn off. He sees a kid outside a bar or going into a room with a grown man at one of the thousands of nameless motels they’ve stayed at over the years and it makes him feel like he’s stuck there all over again, wanting to run and scream and hit and show those men every way his dad’s ever taught him to kill a monster but he can’t, he couldn’t. He couldn’t cause Sammy was too hungry to sleep, had begged Dean to please, please call Dad and tell him to come back. Please Dean, I'm so hungry.
Dean had known better than to call John, though. You never called John when he was on a hunt, not even in an emergency. That concern had only lasted until Sam had turned eight, when John had decided that they were old enough to deal with any issues that came up themselves. And Dean did. He did exactly what he always did: he kept Sammy safe. Safe from the hunger pains that would make him cry at the thought of food and safe from the ways Dean had learned to keep that food on the table.
He thinks Cas knows all of this. Thinks that he understands what Dean did and why he did it, because Cas once destroyed himself to protect Dean, maybe more than once. Dean thinks he understands what it means to rip apart your own body; not consenting but not actively fighting the invaders that take so much pleasure in your skin.
Dean hasn’t forgotten the way the Leviathans sounded in Cas’s body, how pleased they were with the form. He also hasn’t forgotten the way they pushed him to the floor, so reminiscent of the men who would push him against walls and mattresses, rough and predatory and delighting in his fear. He remembers them telling him too that Cas was fighting them, screaming for them to leave him alone. He thinks Cas must have known what they were going to do to him, the same and so much worse than what had already been done; if only in the way that being stabbed time and time again is both familiar and excruciatingly new with every plunge of the knife.
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Years later and Cas still knows, and better yet he understands. He understands when Dean can’t do anything but cling to him and sob, just so damn grateful that somehow he got his best friend, his angel back. He understands when Dean lays next to him in bed and traces meaningless circles on his skin, both of their ears still ringing with all the things they had both been too scared to say, that they were still scared to say but had to, because it felt like keeping them trapped under their tongue, pressed behind their lips wouldn’t hold for another second. He understands when Dean tells him he loves him, understands how hard it is for Dean to reckon the love he feels for Castiel with the love he’s been told to feel in the past.
Even more, he listens. Listens to Dean when the dam inside him finally breaks and he tells Cas everything that’s been building up inside him, all the pain from all the years. Listens when Dean shares the nightmares that play on an endless loop in that recording in the back of his head. Listens when Dean tells him about the pain that wasn’t caused by monsters or angels or demons or God’s fucked up masterplan, but that was caused by regular old human men. Men who should have known better. He listens to Dean confess every sin he’s ever told himself he’s committed, listens to every horrible thing that was done to him and listens to Dean explaining why he deserved it. Listens to Dean explain that really, Cas, it was my fault. Not like I was defenseless, ya know? .
He listens and comforts and then he reminds Dean of all the reasons it was never his fault. He reminds Dean that his father should never have left them at all, and especially not long enough for them to run out of food or money. He reminds Dean of how much he is loved, every part of him; even the ones he thinks are ugly or wrong or broken. He reminds Dean that no matter what, nothing that happened to him was his fault, that it is never the fault nor the responsibility of the child to do what is right. Reminds him that no good people do the things those men did to anyone else, let alone children. He tells Dean that even if the men were fully human, they were no less monsters than every other evil creature they had ever encountered.
So, yes, Castiel knows. And he listens. And he understands. But above all, he loves Dean. Cas has loved Dean since he saw the brilliant, broken, raw purity of his soul of him calling out in Hell and he has grown to love him even more every day since. And Dean? Dean loves Castiel. He loves every bit of him.