Wearing Women's Clothes

Dear Brian,
You know I am 40 years old and I love wearing women's clothes and since I was small (8-10 years old), for some reason I fell in love with shiny, supportive pantyhose. I have just recently started getting all kinds of clothes and I like to wear them. If I could learn makeup, I might even try that. But get this straight...I will not go outside the house. Now I am not gay at all, I am really wanting to get into a relationship with a woman, but how do you advertise, such as on Date.com, that you enjoy this and would also like to have the lady accept it and even get into it?
- Crossdresser

Dear Crossdresser,
Your interest in crossdressing is not unusual. Most men who crossdress are heterosexual. Believe it or not, straight men who crossdress face less hostility for their interest in this fetish than homosexual drag queens who are often unjustly criticized for reinforcing the stereotype that gay men are effeminate and want to be girls. Many women have little trouble accepting transvestism, as long as their boyfriends aren't raiding their closets and stretching their pantyhose and sweaters out of shape. But the average woman might still experience an initial shock upon coming home to discover her boyfriend in a skirt and high-heels, especially if he is attractive enough as a woman to make her wonder if he even needs her. As for meeting women who may prefer a crossdressing man, that's more of a challenge. You can add crossdressing to your profile at Date.com and see what happens, but though there are women who don't "mind" a crossdressing honey, most women with a decided preference for such a man are likely to have an interest in S/M (sadism/masochism) with the woman as the S (sadist) and the man as the M (masochist, often desiring humiliation, including emasculation, at the hands of a dominant female). Such women have so many men groveling at their feet that they are in business, often commanding as much as $200 an hour for a S/M session, and it is the rare dominatrix who will perform sexually with a patron. If such an alternative lifestyle is appealing to you, you can easily find ads for dominatrixes in the classified section of almost any alternative newspaper. There's also Alt.com, a site catering to those with kinky sexual interests.

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