I was with some friends who don't know I'm trans yet (so obviously in boy mode). We were at a restaurant.
Waitress had been "maaming" me the entire time. She comes up to us with our tickets
Friend: "Me and her are together, and these 2 gentlemen are separate"
Waitress: "Wait... haha... that's funny. Why did you call her a gentleman?"
Friend looks at me with the strangest look in his face and laughs.
Friend: "Huh??"
Waitress: "That's a girl... why would you call her a guy?"
Friend is slightly confused... I'm just looking at the waitress with a smile
Friend: "That's a guy... his name is ..."
Waitress: *She looks at me really closely* "Oh my God... I'm sooo confused.."
Friend: "What do you mean, you can't see he's a guy?"
Waitress: "Uhh..." She looks at me "Say something!!"
I say something in a rather female tone
Waitress: *Pauses with an even more confused look on her face* "Wait... Ok I'm still confused... so you used to be a girl and now your a guy? Oh god I'm so embarrassed!!"
I'm just looking at her with a smile, enjoying every minute of her embarrassment and confusion.
Friend: "No... he's always been a guy..."
Waitress: "But I... I don't get it, you look like a girl!! I mean how did you?" as she is moving her hands around her face, indicating that my face looks feminine
Friend: "He has really pretty hair! You're looking at his hair! He's a cosmetologist, I mean you wouldn't eat from a skinny cook would you? It's his advertisement!"
Waitress: "Ummm... I am sooo embarrassed. I'm SO sorry!!"
Me: "That's okay! You can make it up to me by coming by my school and getting your hair done! I go to school at ..."
Waitress: "Oh God... I DEFINITELY will! I promise *my real name*! I'm so sorry!!"
It really made my day, lol!