Confessions of a Cross-dresser

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Maybe it's because Christian Siriano is shouting "hot tranny mess" from every rooftop in New York, or perhaps we've been looking at more cross-dressers than usual with Heatherette's new M.A.C line and all, but this whole men-as-women thing seems a hot topic as of late. How else to explain the London Times essay by a straight cross-dresser who's struggling with how to reveal his affinity for ladieswear to his girlfriend of two years? They're about to move into an apartment they've bought together, and he's afraid she'll discover his habit, which began when he started sneaking into his sister's room at 15 to try on her clothes:

I'd put on her high heels and totter around the bedroom, catching glimpses of myself in the mirror. I particularly enjoyed the miniskirts. This gave me quite a sexual thrill … Then I graduated to her underwear. I loved squeezing into her knickers, especially the thongs. Also I would put on her bras; black was best. Sometimes I'd strut around the bedroom in bra, thong and high heels. I was always terrified that she would come in, but this added to the excitement.


Now 23, he's acquired his own stash of women's "gear," which will be difficult to hide in his new living situation. He's straight as an arrow and would like to come clean to his girlfriend but worries, naturally, she won't be so cool with it. He adds:

I don't want to change because I get so much pleasure out of cross-dressing. It complements the sex I have with Samantha, which I don't want to give up either. But nor do I want to keep a secret from the person I love. I'd hate to think that she had secrets from me.


…I'm also now feeling the urge to “dress up” away from home. I'd love to go out in women's clothes and I'm frightened that one day I'll give in to this desire.

Even in these open-minded times, a man in a woman's clothes brings out the judgment monster in a lot of people, especially in a girl who's unknowingly dating one. This will not go well.

Family secrets: I want to wear my girlfriend's clothes [Times UK]