There's a difference between what emotions are, and feeling them for yourself. Humans, of course, don't know the difference. They are blessed with all of them.
Angels on the other hand... well, they feel things like loyalty and love for their father. Or maybe the occasional human- or in Castiel's case anyway.
~oOo~
It was a simple mission. Save the Righteous Man from perdition, save one of the main pawns for the game to save the world. But, obviously, a job that big is never simple.
It took hard work first of all, and dedication. You can't just pop into hell and grab. The Righteous Man like you're going out for coffee and pop out.
So Castiel's story- where we're starting anyway- starts here.
~oOo~
It took forty years. Forty years of fighting off demons and trudging through utter unholiness. The mission alone nearly destroyed Castiel. And his wings. By the time he found the Righteous Man, his wings were blackened, dry, and burning. Castiel's wings' once magnificent, were now just charred feather and patches of dead skin. And not to mention the scars. Scars from where the strongest demons in hell mauled Castiel. This obviously made it harder to try and drag the Righteous Man out of hell. But now that he found the shredded remains of his soul, he could navigate back out at least.
So he flew out. It wasn't easy or painless, but he did it. He also pieced together the Righteous Man's soul and put it back where it belonged- per his orders.
And then he went back to heaven to heal. Even angels don't jump out of hell fully in tact.
He healed quicker than he could've hoped for, but there were still scars. His wings were permanently blackened and damaged, but no longer painless. Castiel was as healed as he was ever going to be.
~oOo~
But that's when everything happened. Everything involving the Righteous Man- or Dean Winchester, as he was known as on Earth. Years of confusion, apprehension, trust, betrayal, and a journey in learning freedom, with Dean's help.
And then, when Castiel though it couldn't get any worse, it did.
The Scribe of God took control of heaven and cast the angels out. Stole Castiel's grace and forced him to watch his brothers and sisters fall.
The only thing he had left was the knowledge of all the pain and suffering he caused and had no way to fix.
