I am myself a crossdresser, lucky to have an encouraging girlfriend, but I’m still on the closet. My outings are as a male wearing girls clothes, jeans or blouses. I have to say here that I don’t live in such a forward-thinking society, thus, the fear of rejection is greater in comparison to probably where you live.
To the point: when I decide to dress-up I always think of the people I’ll meet – my coworkers, or more terribly, family. I think of everyone but myself. If I think I won’t be seeing them that particular day, I go for it, wishing of course to actually dress up more. Should I always think of people to make my decision? Should I tell them first or rely only on my appearance? I fear that my strategy will isolate me, and curiously it shows a fear towards the people I know rather than to strangers.
It’s difficult. When I was first dealing with things, only a very small number of people knew. Like you, I was definitely very concerned about what other people think – I still am, but to a lesser extent. It’s probably the hardest thing to deal with. So much of our time is spent obsessing over what friends/family/coworkers will do or say, how they’ll react, or what they’ll think about it. I’m definitely *very* lucky to live where I do and know the people I do.
I think your strategy is fine. I’ve been out dressed up before, saw someone I knew, and crossed the street so that they wouldn’t see me. It was scary back then. I don’t think it will necessarily isolate you – maybe you just need do it enough that you get more comfortable.
At the same time, you have to find your own comfort-level. Some people are happy keeping it in the closet, or sharing only with a few people, or being completely open about it. I’m open about it, but I still worry what people will think. I had to work up to it, and it took a long time.
It’s totally ok to go at your own pace and see how you feel. Should you think about other people? Yes. It’s hard for some people to accept, and I’m glad you have an encouraging girlfriend! That will definitely make things easier :) Should you tell people first or just show them? That’s hard to decide. I showed people in bits and pieces over a period of time, to the point where when I did come out about it, it wasn’t a surprise anymore. That might not work for everyone, however. It can definitely depend on where you live/work.
Be patient. Be brave. Take it slowly :)
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