As for the MC, why would anyone expect him to be super confident or good with women? He spent his entire adolescence locked up with zero contact with them. He has some boyish charm, a good physique and a big D, but he has zero idea what he's doing. He's just winging it and getting lucky.
Personally, I like him. He is inexperienced, but not an idiot. And (depending on the player's choices) his heart seems to be in the right place. Him not being overly cocky and pathetically "alpha" like some guys around here is actually a big plus in my eyes.
Dev did good in my book.