‘There’s no downside’

     “Sometimes I look up and wonder, ‘What the hell happened?’” says John, sliding into a booth at Dapper’s East, a classic family-style restaurant on West Addison.
     We order coffee, no food. John doesn’t want lunch, which strikes me as unusual.
     “Do you not eat, as a practice?” I venture.
     No, by necessity. Stomach cancer. Fifteen years ago.
     “They took the whole thing out,” says John, who doesn’t want his last name used. “I beat the odds, but lost my appetite at some point.”
     We last saw each other in 1992. I had been browsing the classifieds in the Reader, looking for story ideas, and noticed an ad for the store he owned on Elston Avenue, selling women’s clothing in large sizes to men.
     “Now there’s a business you just don’t see in the paper much,” I thought, and headed over and met John, when he dressed as a man, and Karen, when she dressed as a woman.
    Focusing just on the One to One Boutique seemed to miss the larger story. So I broadened my scope, attending a dance held by the Chicago Gender Society, also visiting a safe house — an empty apartment used to stash clothing and wigs and makeup away from prying eyes.
     The store is long gone. When did that happen?
     “The Yankees were just winning their first series in a long time” — says John, a baseball fan. “So it must have been ’96.”
     The resultant story was written without any snickering or judgment: just a group of ordinary people who are unusual in a certain way, trying to comprehend what motivates them. It’s an approach I wish more Americans would embrace: to at least entertain the possibility that people different from themselves can be understood instead of simply condemned.
     Cut to last fall, and a letter from a reader about the possibility of Texas secession. At the end, he mentions, “We met about 30 years ago. I’m the person on Elston ...”
     This seemed an opportunity to better understand the connection, if any, between men who dress as women — called “transvestites” 30 years ago — and another, possibly related, group much in the news lately: trans men and women.
     Even then, there were two distinct categories: transvestites, who were straight men, for the most part, dressing as women, and transsexuals, men who defined themselves as women, or women who defined themselves as men, and sometimes transitioned through hormones and surgery.
     We begin at the beginning.
     “My dirty dark secret is, I’m from Mount Greenwood,” says John. “I did not fit in well there.”

     I'll bet....

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