Castiel pulls back just enough to slide a spit slick finger inside of Dean, crooking at he searches for that spot that Dean so unerringly always finds in him.

"I have seen you take beatings in here that most men could not stand," he murmurs, tongue darting out to stab in alongside his finger. "You can take this. You are going to take this from me. You have my permission to come whenever you want and then it will be my turn."

With that, he dives back in, free hand moving around Dean's hip to wrap around his hard cock, jacking him as he continues to press inside.