Tuesday, November 19, 2013

There's still more hiding in that closet.

      Twenty-one years ago, I was scanning the classified ads in the Reader, looking for story ideas, when I noticed an ad for a shop on Elston Avenue that sold women's clothing in large sizes to men. "Hmmm," I thought. "Now THERE'S something you don't see every day." It lead to the only in-depth examination the Sun-Times has ever printed about the Chicago transgender community, and gave me a lot of sympathy for people who feel their true sexual orientation is different than the one they were born with. It's a struggle. 
     An interesting social question now is whether transgender folk will be able to piggyback on the advances made by gays and lesbians. On the surface, they are a harder pill for the straight world to accept, just by appearances, plus their numbers are a fraction of the percentage of homosexuals, which makes them even easier to abuse. And many consider themselves straight, which only adds to the confusion. So far they have made surprising progress—a rising tide floats all boats—though expect a backlash.
     Wednesday, Nov. 20, is Transgender Day of Remembrance, a solemn event designed to honor those murdered for their orientation. Whether or not you feel comfortable around such people, I hope everyone agrees it's not something a person should be killed for.
      So now is a good moment to haul this story out of the vault. You'll notice I never mention the word "transgender" — the term wasn't in vogue then — nor do I use the word "transsexual," because I mistakenly assumed they were a subset of transvestism, and I was trying to make the thing as simple as I could. An error I learned when an angry transsexual whom I had identified as a "transvestite" in a photo--a slur, since she considered transvestites to be amateurs—showed up at the newspaper and demanded a correction, which we ran.


     Jenny has sparkling blue eyes, a small, upturned nose and a
cascade of curly blond hair tumbling over her right shoulder.
     With a rhinestone nail charm centered on each red fingernail, a
dab of blush at her decolletage, and deftly applied make-up, it's
easy to believe her when she says she spent three hours getting ready
to go out.
     The shimmery blue and silver dress is custom-made, she says, and
it's easy to believe that, too, since with the spike heels, Jenny
tops out at perhaps 6-foot-7.
     "I'm a bigger girl, I know," she says, smiling radiantly. "I
can't go out to a mall — hey, I've got a football player's
     So instead, Jenny has come here, to a banquet hall on the
Northwest Side of Chicago, where the city's tiny, secretive
transvestite community is having one of its many regular social
functions — this one a dinner and gala pageant to select "Miss
Chicago Gender Society 1992."
     About 110 people — mostly men dressed as women, with a
smattering of wives and girlfriends and boyfriends and even
somebody's mother — mingle and chat, complimenting each others'
dresses, primping at their wigs, sipping drinks.
     Less than 15 years ago, it was against the law in Chicago for
people to wear clothing of the opposite sex. The ordinance was in
place until 1978, when the Illinois Supreme Court overturned the
conviction of two men arrested in 1974 for wearing dresses.
     Today, several hundred people belong to Chicago's two
transvestite groups — the Chicago Gender Society, which admits any
cross-dresser of any sexual orientation, and the Society of Second
Self, or Tri-S, which limits its members to heterosexual
transvestites and is more family-oriented.
     Still, transvestism is one of society's deepest taboos. While
homosexuals have made progress in becoming better understood and, in
places, accepted by society as a whole, transvestites struggle
against a stigma so strong that few feel they can risk even revealing
their real names.
     The president of Tri-S refused to have his picture taken, even
dressed as Naomi, for fear fellow lawyers at his Loop law firm would
recognize him. The president of the Gender Society, posing for a
newspaper picture, quips, "My life is over."
     "I personally don't care (if people know I'm a transvestite),"
says Leslie, a six-footer in a white mini-skirt and hoop earings who
works as a contractor in the suburbs. "But I have to protect the rest
of those people: my 7-year-old son, my wife, my other family
     Most transvestites describe themselves as heterosexual, though
the term sometimes gets stretched a bit. One transvestite at the gala
says he is heterosexual, but adds that he lives as a woman and dates
     Still, many transvestites have wives, families, and are not
effeminate when dressed as men, many say.
     "I'm straight, married, I have a 9-to-5 job, a sales job," says
Jenny. "I battle over turf with the rest of the sales people. I play
    Indeed, one academic explanation of transvestism is that
 it is the ironic result of a sort of super-masculinity.
     "One of the ways we understand transvestism is an attempt to
integrate what are otherwise carefully separate parts of one's self,"
says Dr. Richard Carroll, director of the Sex and Marital Therapy
program at the University of Chicago. "Some men, in most of their
lives, are aggressive and hypermasculine, and it's as if some men
have split off the feminine aspects of themselves so completely they
have to cross dress and play a role to get in touch with the more
feminine part of themselves."
     What is a mystery, however, is whether the strong masculinity is
a cause of, or a reaction to, transvestism.
     "A lot of transvestites will overcompensate in male life," says
Anjelica, who worked for years as a mailman "partly because of the
     Transvestites themselves, who generally say they began dressing
in female clothing at a very young age, describe cross-dressing as a
     "I just have to do it; it's like this urge," says Leslie.
     While transvestites are initially drawn to women's clothing as
an erotic experience, the appeal often changes into a general state
of well-being.
     "The sexual element becomes less important and dressing and
passing as female more important. Just the experience of being
 cross-dressed is associated with a sense of calm, peace, and freedom
from stress," says Carroll. "For many transvestites, the sexual aspect 
becomes less important as they grow older. It just feels peaceful to 
them. Some men describe it like finally being at home."
     Despite the calm transvestites find in cross-dressing, they can
face a variety of severe emotional problems, the result of conflict
between their inner impulses and the outer dictates of society.
Transvestites are thought to commit suicide more frequently.
     Pervasive public ridicule, which can result in physical attack,
also is a problem.
     Then there is the issue of dealing with their families. Some
wives divorce their husbands after learning that they are
transvestites. Others grow to accept it.
     Nicole, attending the Gender Society gala with her husband,
Gloria, was married for four years before she discovered women's
clothing in the trunk of their car.
     "I was devastated — I thought he had a girlfriend," she says,
holding back tears. Learning that it was her husband's clothing came
as a relief. "I thought, `Oh, is that all? We don't have to get a
     Asked if she liked the fact that her husband is a transvestite,
Nicole says: "I understand she has her needs." But some wives
actually feel closer to their husbands when they are in their female
     "In some ways, the partner preferred him when he was
cross-dressed," says Carroll, referring to a high-level business
executive and his wife. "He was calmer, open, more relaxed and more
      And not all transvestites tell their wives. Michele, attending
the gala while his wife of 22 years was out of town, says the wife
has no idea of his transvestism and he isn't going to tell her. "Why
create a problem?" he says.
     Marriage can actually facilitate the development of a man's
transvestism, since it takes him out of the posturing of the dating
world and, not incidentally, provides ready access to women's
     "In the dating scene, you have to be one of the macho guys, a
male male," says one cross-dresser. "When I got married, I didn't
have to go through that ritual, all that pressure trying to find a
    Several businesses in Chicago cater to transvestites. In addition
to a photography studio, a beauty salon and a meeting service, there
is at least one boutique, a nondescript storefront on Elston Avenue.
     Inside the boutique are racks of Cover Girl cosmetics, costume
jewelry, jumbo-size Frederick's of Hollywood-type undergarments and
clothes, mostly culled from secondhand shops.
     "We try to keep a low profile," says the owner, who goes by the
name Karen when dressed as a woman. "They come here because we are
discreet, quiet and no one bothers them."
     While he talks, four men, one at a time, slip into the store and
head to the back.
     In the back of the store are a variety of transvestite
publications on dressing, makeup and feminine deportment, as well as
racks of paperback novels with titles such as "Trio in Skirts," "Girl
for a Week," and "Men in Skirts." Karen describes them as "basically
good, wholesome fantasies," though it is safe to say not everyone
would agree.
     A common refrain heard again and again from cross-dressers is
they are not trying to hurt anybody, just be themselves, living life
the best they can.
     "Once you get over the question of men dressing as women, there
is really very little unusual about it," says Karen, and, indeed,
perhaps what is most unexpected about transvestites is how ordinary
their lives can be, outside of their cross-dressing.
     Karen has a photo album of himself, in women's clothes, posing
inside suburban interiors, mugging with friends at parties, dressed
as a cheerleader, as Little Bo Peep, in an evening gown.
     But in the back of the album are a different set of photos —
Ebbetts Field memorabilia, Stan Musial's locker, a bat once swung by
Babe Ruth — taken during a cherished visit to the Baseball Hall of
Fame in Cooperstown, N.Y.
     "That's my primary interest," Karen says.
                   Originally published in the Chicago Sun-Times, May 24, 1992


  1. The logistics and nomenclature of this community has always confused me. Does anyone know of a good, current website regarding this?

  2. I was going to send this to FaceBook with a snarky remark directed at those who love to ridicule anyone or any group different from themselves, but decided not to, out of pure cowardice.



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