Chicago -- It was the skin—smooth and hairless as a newborn’s forearm—that I fastened on when I saw Sara Andrews, the first “transwoman” I had ever met, at the Kit Kat Lounge & Supper Club in Boystown, on Chicago’s North Side. The ambiance at the club was glitter balls, silver-leather banquettes, Busby Berkeley dance loops projected onto the walls, and as entertainers a bevy of dressed-to-the-hilt, lip-synching “divas,” as the Kit Kat calls its drag lineup. The Kit Kat is a tourist destination as well as a locals’ favorite, and it was packed, even on a Thursday night. The crowd had two distinct demographic components: at the tables, mostly heterosexual women on a girls’ night out, including a raucous bachelorette party; at the bar, clumps of equally high-spirited gay men in a social world in which the heterosexual ladies on the periphery didn’t exist.
Sara Andrews, in her mid-30s and wearing stilettos and a lush brunette wig, was quite frankly lovely: tall, elegant, and graceful as she wove among the tables so that audience members could tuck dollar bills into her skimpy cheetah-print bodysuit. My idea of a transgender woman had been Jeffrey Tambor playing the fiftysomething dad who puts on makeup and becomes “Maura” in the Golden Globe-winning Amazon series Transparent (modeled on the 2011 coming-out of Transparent creator Jill Soloway’s own father)—or, possibly, 65-year-old Olympic medalist and Kardashian consort Bruce Jenner, who has had Adam’s apple-reducing surgery and is reportedly undergoing the “transition,” as transgender people call it. Neither the late-middle-aged Tambor (with his string of wives and five children) nor the late-middle-aged Jenner, both with robust physiques and pronounced manjaws, had struck me as especially convincing candidates for femaleness.
Andrews was different. I stared at her mesmerized, looking for signs that she had once been male. Skillfully cosmeticized facial features a shade sharp? Breasts perhaps too widely spaced on what was a very large chest frame? But it was really the skin. Some transgender women don’t go all the way with genital surgery, and some don’t bother with the daily estrogen pills plus injections of other hormones that suppress masculine secondary sex characteristics and encourage the growth of mammary tissue. But nearly all undergo extensive electrolysis or its laser equivalent to remove every last coarse hair not only from the face but from the body. Since even the most fair-complexioned women are coated with delicate down, the almost completely hairless skin of the transwomen I met that night was the tell: ever so faintly unnatural-looking.
My Virgil for this adventure was J. Michael Bailey, 58, a professor of psychology at Northwestern University who may be the most controversial scientist ever to study and write about the male-to-female transition, and certainly the most intensely loathed by transgender activists. His 2003 book The Man Who Would Be Queen: The Science of Gender-Bending and Transsexualism, its cover featuring a photo of a pair of muscular masculine calves terminating in large feet encased in a pair of high-heeled pumps, promoted a thesis that was controversial in 2003 and is even more controversial now, when there is a story about gender transition in the news nearly every day. Bailey, who has devoted his academic career to outré forms of human sexuality, argued that transgenderism (the new, politically correct word for what was called “transsexualism” a decade ago) isn’t a matter of a mismatch between one’s body and one’s innate identity, as transgender activists and their numerous allies have been arguing. Instead, it’s a matter of sexual desire and romantic yearning. “Those who love men become women to attract them,” Bailey wrote. “Those who love women become the women they love.”