The first time I went out dressed female was a huge thing just in itself. It was a test for me to see if I had the courage to do it. It was also a completely new experience and I didn’t know how people would react or how I would feel about that.
Having done just being visible, I realised that I could cope with it which was good, but it then didn’t achieve anything, so I needed to interact with some people to see how they responded to me as a non-passing person with a voice that confirmed my sex even if my face hadn’t already given me away. I found that I could pass this test too. Even if it was obvious that the people I spoke to (shops and coffee shop staff) saw me as a man or cross dresser or whatever, I was okay. But then I felt that these interactions didn’t count because they were strangers so why would I care what they thought anyway. That’s why I next needed to try being Nicola with a friend, to see whether I could handle it with someone I knew and whose opinion of me matters.
Going to the queer bar the first time was sort of just being visible, but in a different context, and didn’t quite achieve anything because I didn’t talk to anyone. Going for dinner and then hotel breakfast were a bit different because it was being visible in normal life and seeing how I felt with people’s reactions where I was visible for longer (when shopping, anyone who clocks me as I pass is gone in seconds. Sitting at a table in a restaurant, someone can stare and comment for a long time). It was more of a “real life experience” test, although again too short and not enough interaction to be real.
Hence just putting on a skirt and going to a couple of shops doesn’t make any new progress.
Progress would be having a conversation being openly a non-passing pre-transition trans woman; or spending a day as Nicola somewhere.
I have this silly idea (which my wife would never agree to) of going for a week’s holiday by myself, maybe a cruise (not my thing, but contained environment and forced visibility) and taking only female clothing so I live a whole week as a woman. That would be a real test. But I don’t think that is possible.
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