"Dean. Two thousand years of experience. Trust me, I know what I'm doing and how to avoid hurting the people I sleep with." There's a brief pause before a mischievous "Unless they're into that."

A quick snap of his fingers later to get them covered in lube, he's slowly pressing them in Dean before twisting his wrist and expertly seeking out Dean's prostate to give it a firm rub to illustrate a major benefit and motivation to be on the receiving end.

"Feels good, doesn't it?" he murmurs, knowing damn well that the answer is 'yes' even though it's probably weird for Dean.