More often than not, I have told about my dressing.
One time when I was getting ready to go out, my daughter walked into my room for something (I had already moved into a separate bedroom) and she asked me about the smell of nail polish. I made up an excuse about using clear nail polish for something or other (I can’t remember what).
A few years later, after the time my spouse and I had already decided that we would eventually get a divorce, the same daughter found some of my clothes. When I decided to get divorced, I decided I would eventually tell my kids, since I didn’t want them to find my stuff after I die and then wonder about me. I waned them to be able to ask questions. On this day, I was going out at the time (not dressed), but did talk with her about an hour later. It was probably a little sooner than I planned to talk with her, but there was no real excuse except the truth. I think my coming out to her made her feel more comfortable for her some time later to talk to me about her sexual preferences, feeling I’d be understanding.
When my waxer asked me about why I get my legs waxed, I hesitated, but did tell her about my crossdressing. As she moved on, I told the next two women who do my waxing as well. I have even shown pictures of me dressed.
One time I bought some platform high heels in black and in silver. A few days later I decided I wanted it in red too, but most stores in the chain seemed to be out of it. But there was one place near where I worked that had it in stock. So I went out at lunch hour, went in, picked it up and returned to the counter. After the woman ahead of me paid, the cashier asked me “Did I know what to get, or was I told what to get?” I told her I knew what to get, and added (perhaps a bit sheepishly) that they were for me. We did have a conversation about the shoes before I left.
There was a women’s clothing store about 1/4 mile from my home. I would often browse there, sometimes prompted by something I saw in an email from them. On a few occasions, I would order things online and have them shipped to the store. It was close enough to home that it wasn’t really out of my way, and shipping to the store was free. When the store announced their closing of their brick and mortar stores, I did go in dressed a couple of times. One of the clerks passed by me and must have recognized me, saying “Oh. Hi!” before continuing on what I was doing.
One time I had a dental appointment on Halloween. On that day I had painted my nails candy corn. All the hygienists came in to have a look at my nails. When the dentist came in, he proceeded to tell me about the time he wore a skirt on Halloween. He started with a rhetorical “I don’t know if you’ve ever worn a skirt before ….” I didn’t say anything (well he didn’t really ask a question) despite thinking to myself “Yeah, all the time!” He proceeded to tell me about how his legs were cold and how airy it was and how he asked his wife why women wear such things. It was very funny the way he was describing it.
Since the question was “Did I ever hide it,” the answer would be yes. But most of the time, I would have to say no.
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