For brevity:
Nephew: "I feel bad for your parents" - OK.
My parents: "I feel bad for you, pathetic" - I feel bad for you missing out on a great and kind child.
My dad: "Hey, it's okay if you want to be gay... but this trans-thing? I don't know."
Doctor: "So you want to be a male?" - Not likely.
Some woman: "When do you get the two surgeries? (thinking I was FTM)" - I opted for one, thank you very much.
Waitress: "Whispering to another waitress: that's a ->-bleeped-<-!" - on the 5th day I came out, so very fragile.
A guy I dated who knew my condition and SRS: "Can you get pregnant?" - Me, no.
A lesbian friend: "You want to be a ->-bleeped-<- then?" - nevermind.
A female friend: "Who wants to become a woman?" - uhhh me?
A guy friend: "Respect for losing all your male privileges" - ... which are?
Random woman: "Are you the one that does the face paint this afternoon with the kids?" - no I wear this daily.
Random bloke: "I want to make a compliment... for your courage, you are transgender, right?" hmm okay.

Edit: removed a couple non essential, added a few more I just remembered.