Portrait of a Lady

CityPaper.net – by Ashlea Halpern

The strange allure of cross-dressers

My first exposure to cross-dressers was the granny-wigged Robin Williams in Mrs. Doubtfire, followed by Aerosmith’s “Dude Looks Like A Lady.” My inaugural in-person CD encounter was with a wayward high school boyfriend who occasionally wore lipstick and pranced around his parents’ living room in my bra and panties. Sometimes with his buddies, who also wore bras.

Mrs. Doubtfire, of course, wasn’t a cross-dresser ? she was an out-of-work actor posing as a nanny. Steven Tyler’s lady had the body of a Venus, but her story was only skin-deep. And the old boyfriend, well, he had other issues.

So what exactly defines cross-dressing? Is it merely a fetish? And does it have anything to do with sexual preference?

For answers, I turn to 58-year-old Exton-Lionville resident JoAnn Roberts, publisher of LadyLike magazine, author of the multivolume Art & Illusion: A Guide to Crossdressing, co-founder of the Renaissance Transgender Association, and organizer of the Beauty and the Beach cross-dressers’ weekender in Rehoboth, Del. Twice married, with two grown children, the part-time cross-dresser and “recovering Catholic” was around 6 years old when she found one of her mother’s nightgowns in a hamper and slipped it on. “I couldn’t believe how soft it was,” she remembers. “I slept in it all night.”