I can sort of understand your concern there, but in small doses, I think it would be more entertaining to play that out. You only really need to do it once with any given character, and once Dean's figured out where they slot into his life, I imagine he'd be more relaxed about approaching them for further encounters. Given that Dean's shown to be able to follow orders with people he trusts, he doesn't always have to be the one who wins those encounters either. He can legitimately decide someone could outdo him in certain ways and still want to have sex with them. I just imagine he'd be a little more tense about it.

But thank you for taking the crit so well. Not everyone does, as I'm sure you know.