I was wondering what has been the most embarrassing question asked of you by a family member. The reason why I'm asking is because I have just had an unforgettable experience with my grandmother. My sister, grandmother and I were sitting at the kitchen table at my mom's birthday party. She started asking us if we had regular periods because she has menstrual problems when she was young. This was invasive enough, but then my sister looked at me and said "Watch out! You're gonna have kids!". This prompted me to say "No way! I'm not having any!". My grandmother looked at us and then asked, "You girls aren't sexually active are you?". Keep in mind my sister is 28 and I'm 24, what does she think?! So turning my head away I mumble, "No, I don't have a boyfriend right now, so no." Then she asks, "Are you girls still virgins?" I looked at my sister and looked around for someone to save me. No such luck. My sister wasn't gonna talk so I said, "Yes grandma I am." Then she replies, "Good, because that's a special gift you share with your husband." AHHH! What the hell is wrong with her? In telling my mom this story (this is her mother), she recounted a story in which her grandmother asked her if she had ever had an orgasm. Unfortunately, my mom was dumb enough to answer her question.
Does anyone have any good stories like this?