Everything Castiel is doing screams rough around the edges, but it's no surprise and Crowley really doesn't mind it at all. Castiel is breaking taboos for the first time and Crowley likes to think that he had more than a little influence in that. He feels pride at the thought and he knows that Castiel can only get better with some help from his friendly neighborhood King of Hell.

His breath hitches when he feels Castiel's teeth sink in and oh, Castiel had read that one right. His cock twitches in Castiel's hand and his mouth falls open. It's not enough with Castiel's slow pace and he slips his hand down to wrap around Castiel's hand on himself, showing him a slightly faster pace. "Like this, darling."

This time he does tug lightly at Castiel's hair and he dips his own head to press their lips together. The kiss is slow and messy, just like Castiel's first attempt at a handjob, but this is by design. Crowley doesn't have many opportunities for these sort of kisses and he has to admit that they're nice in their way.