I seem to be mistaken for a female quite a lot when not intending it. I don't know if it's my face, body shape (natural feminine fat distribution), or mannerisms, but it seems to happen a lot, and not just as a momentary misidentification. It creates a mixture of emotions.
Some examples:
A few months ago, I learned that a group of chess players meet at a nearby coffeeshop every weekend. Although it had been years since I played chess, I went, and asked one of the men there if he wanted to play. We played three or four games, chatting throughout about the local real estate market (he is a realtor) and the goings on in the neighborhood. At the end, he introduced me to several other people there. Although I told him my name was "Jesse", he introduced me as "Jess" to everyone. He said, "she lives here in the neighborhood". A few of the people he introduced me to seemed surprised to see me identified as female (maybe it was my day-old stubble). This guy was probably a bit older than me (I'm 40), so it wasn't senility.
A few years back, I was visiting some family in So Cal. I took a break from the family and went rollerblading on Santa Monica Beach with my shirt off. A young woman rode up to me from behind on her bike, and said, "Miss, this isn't a topless beach! You need to put your top back on!" I have maybe small manboobs, and have little body hair, but am somewhat muscular. So it was mortifying. She was flummoxed when I replied, "Excuse me?" in a baritone. She then proceeded to chat me up a bit riding along side me, but I could tell she was very embarrassed.
A woman was doing lat pulldowns at the gym, and I walked up to the station and did regular pull-ups at the pull-up rig next to her. I pulled 14 or 15... We stopped our set at about the same time, and she (a woman whose appearance many people would characterize as "lesbian-ish") said to me, "you remind me of a girl I went to high school with...she was so competitive." Although I took it as an odd comment, I replied that I wasn't competing with her, I was just getting a workout. We had about a 10-minute conversation about high school, music, and other things. At the end, she asked me if I could give her some tips on doing pullups, since I could do a lot of pull ups for a woman. Here again, I had about a day of stubble on my chin and had been talking in my normal male voice the whole time.
A year or so ago, I met a male friend for some beers at a local pub. There was a group of lesbians at the next table that he knew (he is a doctor and two of them are doctors as well). He introduced me to them, and I chatted with them for a while. He told me the next day that when I went to the bar to buy some drinks, the women asked him, "How do you know her? You know that our type aren't interested in you!!"
I could provide lots of other recent examples of these unplanned identifications of me as female. I've been mistaken for a female many times, even when wearing a suit and tie.
On the one hand, I am thrilled by it. On the other, it makes me terrified. How feminine do I look to others? I like being a man, and want to interact with others as a man when I am in male mode.
A third feeling is one of frustration. There are times when I have attempted to be mistaken for female by making my appearance somewhat more androgynous (closer shaving, clothing that is less stereotypically male, but always get called "sir". I'd love to get mistaken for a female at a store and be able to buy a few clothing items without embarrassment.
Any thoughts about what might prompt people to read me as female when I don't intend it, but male when I do intend a more androgynous appearance?
Cheers...Jess