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*aycee
writes: I'm 29 and ever since I was 12 or so I've been secretly wearing women's clothing. Sometimes just undies/tights etc and sometimes dressing up completely as a woman. At different times I have stopped and sometimes even got rid of all my feminine clothing but sooner or later I start again. I'm not gay though I do enjoy chatting online with other crossdressers. All this would be OK (well, sort of) except that I am totally in love with a great girl and I think we have a future. I hate keeping this secret from her but I don't think she could take it if I told her... What should I do!? :( Reply to this Question
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male
reader, anonymous, writes (23 December 2007):
Try and find a way to broach the subject with her, at least then you'll have a better idea of her thoughts on the topic.
If dressing up is something you really enjoy doing, you are going to find it difficult to give up, sounds as though you've already been through one purging process that did not work.
The sooner you can share this with her the better, hopefully she'll fully accept it, e.g. Grayson Perry "Turner Prize Winner" with his wife and daughter. Maybe she'll say "okay, so long as I don't have to see it" after all she fell for you as a man. Try to imagine her with socks stuffed down the front of her trousers, her boobs taped down and stumble stuck on her face, you get the idea.
Good luck, you may end up as a pair of happy lipstick lesbians.
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male
reader, anonymous, writes (28 November 2005): Im 16 an ive done this a few times too.Im not gay iether an hav had girlfriends. I totaly disagree with the last two women but agree with the guy, make it playful.
I stupidly told 1 girl an she totaly lost intrest(no suprise) but kept it silent since were v.close friends.
Its made me much more comfortable to hear from someone else like me.thanks :)
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male
reader, PsychicHigh +, writes (17 November 2005):
Easy to remember that secrets hurt when it turns into gossip and you have to hear from a 3rd party, but both keep secrets about everything.
Best bet would be not to just jump out and say how you like to crossdress, but do it in a way that's playful. If you know for sure that her cloths will fit you without stretching them, or she has an old skirt that she wont wear but fits you. One day when getting into the mood kinda toss it on and try something like "oh, do I look sexy or what."
Being a guy myself that does crossdress I don't feel ashamed about it either. Just for sometimes it's more comfortable to wear their clothes instead of your own.
Just have to keep in mind that many girls throughout their lives will wear mens clothing at one time or another, so it's not fair that their clothing is theirs only. If everyone wants equality remember equality isn't all mine and nothing is yours.
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reader, anonymous, writes (17 November 2005): Doesn't she have a right to know what's happening in her own relationship? Relationships with secrets in them are uncomfortable all round, though, and are likely to run into problems in the future. She will find out someday and the consequences could be painful for you and her. In all fairness to her, sit her down and tell her, now. Then she can decide whether this relationship is right for her. I wish you a happy relationship, but whether that'll be with her or not, only you and she can decide. Good luck.
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female
reader, wishes +, writes (17 November 2005):
 You need to tell her. Stop living a lie. If she doesnt accept you for who you are then its not worth it. She should love you for being yourself and if that comes with you cross dressing then she will get used to it. Allow her space and patience until she does understand- it may take a while for her to get used to the idea. Best wishes x
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