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Wednesday, October 1, 2014 |  Madison, WI: 49.0° F  Overcast
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Tell All: No cross-dressing allowed
My girlfriend discovered my secret

Dear Tell All: Recently my girlfriend came home to find me dressed in her clothes. My attraction to cross-dressing was something I had not shared with her. Needless to say, she freaked! I tried to explain that it was only a fetish, that I did it for enjoyment only, and that I'd appreciate it if she would participate with me.

She could not/would not understand. Got tossed out on my rear.

What I need to know: Are there women out there who will accept this behavior and embrace the needs of boys who want to be girls? If so, how and where can you find them?

Since I've been found out, I would really like to find a woman to help me get in touch with my femme self.

All Dressed Up and No Place to Go

Dear Dressed Up: I feel bad that your girlfriend didn't understand, and that you got tossed out. Then again, you didn't help matters by concealing your cross-dressing fetish from her. She might have wondered: What else is he hiding?

In 2013 -- and especially in Madison -- there's no reason to keep quiet about such things. We've come a long way since the 1950s, when cross-dressing was taboo and the movie Glen or Glenda? exploited it to sensationalistic effect. Nowadays, you can attend regular drag shows at Plan B or Five Nightclub. You can find cross-dressing hookups on online dating sites, probably within seconds. Go to the Isthmus Personals page online, for example, and click Man Seeking a Woman for Cross Dressing. Yep, it's a standard category, right there on the drop-down menu.

And, who knows, maybe your original girlfriend will even come around after the shock wears off. Why not invite her to Plan B in a month or two, for drinks and a drag show? Even if you don't get back together, you can show her that her freaked-out response to your cross-dressing was unwarranted.

Do you have a question about life or love in Madison? Write Tell All, 101 King St., Madison, WI 53703. Or email

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