From my mother: "so... Whose pecker are you getting?" She meant it honestly and that made it so ridiculous I just laughed myself sick.
From my grandmother: "Wait, does this mean that you like women?"
From my brothers as a unit through the elected awkward question congressman: "Are you a boy or a girl??" (I'm the oldest by a large margin)
From strangers I've been asked how I masturbate (Perfectly fine, thanks), how's my sex life (very active and better than theirs), if I have "both sets" now, (wouldn't you like to know?) and my all time favorite, so your husband is a "->-bleeped-<-"? (I hate that word).
If I think of any more I'll let you know. Edit to add, I just remembered another one. "So, do you know Laverne Cox?" Because apparently we all know each other.