My first "male fail" happened a few weeks ago.
My spouse and I went to lunch at this tiny Italian place. I was wearing a compression shirt that is beginning to fail at the task assigned to it, a very loose t-shirt, a pair of women's jeans, my favorite feminine black cap, and of course earrings that aren't too loudly female. I've taken to shaving with a new razor lately, a three bladed razor instead of the old dual and it really has been giving me a nice close shave so the beard is less visible plus I think the higher estrogen dosage my endo prescribed last month is having a small effect on the facial hair too. (E3000 appointment in 2 more months!)
Anyway, there we are in the Italian restaurant. I admit it was a wee bit dark and after the waiter takes my spouse's order, I get "And you, ma'am?" I place my order and I've been working on using my voice with male resonance minimized, which raises the pitch a bit, though not sufficiently for my taste, due to that darned paralyzed vocal cord, and he doesn't bat an eye. He walks off and I grin. My spouse looks at me funny, and I say, "I think I just mis-heard the waiter." She says, "No you didn't. He said ma'am when talking to you." He comes back, brings our iced teas, and says, "Your orders will be out shortly, ladies."
Then, less than a week later, we're at another place for lunch (a Chili's), almost the same androgynous clothing, and we get "What can I get for you ladies today?"
Now as I've said before, raising pitch is very difficult for me due to a paralyzed vocal cord, so my focus has been on eliminating male resonance. I've measured pitch and it just doesn't want to go much beyond about 165 Hz right now with that specific implant in the bad cord. But two days ago I answer the phone and someone asks for me by my male name. I say, "What can I do for you?" And I get a "Well, I need to talk to him, ma'am."
And my final story isn't about passing, but about acceptance.
A couple who I know and am dear friends with have a 5 year old son who has witnessed me working my way through this. A few weeks back, his mother mentioned that we were going to all go to dinner together. That produced the following conversation (I'm paraphrasing from memory) with her boy.
Her son: "I remember Liz! Sometimes Liz is <MaleName> and sometimes <MaleName> is Liz!"
My friend: "Does this bother you?"
Her son looks at her totally confused like should it? He then says: "No! Liz is Liz! I like Liz!"
We had a great dinner and the little one enjoyed getting and keeping my attention.