(I had wrapped a bottle of wine to give to my grandfather as a Christmas Present) Me: Merry Christmas, Grandad! Grandad: (without opening it) Oh, lovely! A jumbo size pack of condoms! Just what I needed! Grandmother: That's an oddly shaped box of condoms... Grandad: (pointing to his crotch) Hey, they haven't seen the shape of this yet!
(My grandma thought it was totally appropriate to tell me about her first time with my now deceased grandpa.) Grandma: I looked at that thing and I said "That'll NEVER fit!" Me: *Awkward laugh* Oh hehe, that's pretty crazy! Grandma: Say, why don't you ever bring your boyfriend over here to visit? (maybe it's cause you tell gross sex stories.)