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We've been through this recently. The kids had seen me dressed a few times for Halloween and other costume events. They didn't know that it was something I did otherwise. A few months back, though, I decided to go ahead and have the talk with my daughter (14 yrs old). She seemed to take it very well. She asked a few questions, I answered them, and then the subject was dropped and didn't come back up.
My son (9 yrs old) had made some negative comments about me dressing for Halloween, so I was reluctant to talk to him about it yet. That became a barrier to me being able to go out to events dressed up. If he wasn't supposed to know, then I could hardly walk out the door past him wearing a dress. That became too constricting. Last week, I decided he was going to have to get used to seeing me dressed up. I still haven't really talked to him about it. I just said that I was going out and would be dressing up as a woman. It didn't seem to bother him. I couldn't give him goodnight kisses with my makeup on, but we blew each other kisses and he was fine with it. I went out Monday and Tuesday, and haven't gotten any negative feedback from him yet.
On Tuesday, though, my daughter, who I had thought was so cool about it, giggled her head off, didn't want to look at me, and told me she wished I wouldn't do that in front of them. Knowing her as I do, I didn't take what she said too seriously. I just reminded her of Thumper's Rule. On Monday, as I was getting ready to head out to the club, she had told me that she couldn't wait until she was old enough to go to places like that. I interpret the two opposite reactions as evidence that she is mostly a prude but aspires to be a little wild now and then. In other words, she's her father's daughter. :)
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Both my daughters are adults now but when they were in high school they both knew I dressed for an event at work. They helped me to pick out my outfit. Now in coversation they both agree that crossdressers can be hetero and both have said it was the person's choice. They don't say that they know I dress but they have seen some of my clothes. Billie Jean