I've got one.
My nonna and I were going out to lunch with my boyfriend, who just happens to look very effeminate. It's not his fault, he's just... Pretty.
She didn't know it was him, since it was her first time meeting him, and as soon as he was in hearing distance she looked at me and said, in a heavy Italian accent, "Is that one of those transgenders? She doesn't make a very convincing boy."
He thought it was so funny, he still laughs uncontrollably every time he thinks about it. She still doesn't think he was born male...