I think that the hardest part for the guy is going to be afterward. I mean, it sounds like they both haven't had any yet so where's the basis of comparison (besides perhaps a sexual appliance of some sort

) As long as he makes things sufficiently romantic, pulls out his best bag of tricks and rev's her up as much as possible, the "actuality" is academic. The mood afterward ... talking ... holding ... calling the next day ... ect, is the important part. You know her girlfriends are going to be asking about it .. well that and his penis size. Moral of The Story: Don't Be A Dick After You Dip Your Wick.