A Cross-Dresser’s Journey

The politics of clothing: Sylvia Stewart (r) poses with a “La Cagelle” at [email protected] after a performance of La Cage aux Folles.

From closet to ‘La Cage’
by Sylvia Stewart  •  Photo by Dalton DeHart

My name is Sylvia Stewart, and I am a cross-dresser. This is unique for several reasons: even though I chose my femme name decades ago, for most of my adult life I was closeted and burdened with feelings of guilt, shame, and confusion. It is very liberating to tell others who I am because I have come to terms with what I am.

It is widely believed that most cross-dressers are heterosexual, although statistics are admittedly hard to come by. Cross-dressers are part of the “transgender” group, the last category of “LGBT.” But within that “T” category, we come after transsexuals, transgenderists, and drag queens.

Because we are seen as notoriously secretive and reclusive, it could be said that we are “the Rodney (or Rhonda?) Dangerfields of the LGBT movement.” The Human Rights Campaign (HRC) and the 2007 version of the Employment Non-Discrimination Act (ENDA) both advocate making sexual orientation a protected category, but not gender identity and expression. The debate surrounding this puts the “T” group in a precarious position, and we appreciate the efforts of the gay community to support us.

So, what is a cross-dresser? One definition would be that we are people who wear clothing usually worn by the opposite sex, such as males who present as female. Most who fit this category are, by definition, men.

In today’s society, clothing options have expanded dramatically for women. They can wear overalls, steel-toed boots, and have hair cut short—and unless they are at a formal function, few people will say anything. But let a man put on a dress and high heels, and all hell breaks loose. Clothing typically seen as female represents “the weaker sex,” and why would a man want to surrender to that? The politics of clothing is a fascinating topic. Importantly, cross-dressing is not considered a pathological behavior by the majority of mental-health professionals.

There are many types of cross-dressers—from those with supportive wives and families to those in situations where a wife or girlfriend completely rejects the thought of “her man” dressing as a woman. Having a disapproving partner usually results in the cross-dresser leading a closeted double life, in constant fear that their clothing stash will be discovered. Others enjoy great confidence, enabling them to go out in public, presenting as female and “passing” without getting “read.”

How does a man discover he is a cross-dresser possessing “the nylon gene”? For me, the journey began in the late ’50s when I was 12. It was a time of glamorous feminine apparel and accessories. I was curious to see what it felt like to wear these items—to get the rush of trying something forbidden. Like many of us, the first women’s clothes I tried on belonged to my mother, and I got hooked. At 17, I gave my femme persona the name “Sylvia” and discovered from a newspaper that there was a name for my secret—“transvestite”—which was thought to be curable through electric shock treatments. Being a resilient person, I pressed on.

In college during the turbulent late-’60s and early-’70s, I assembled my first feminine wardrobe. Then, after meeting my wife in the late ’70s, I “purged” by discarding every piece of feminine attire in the belief that I could “go straight.” My profession was banking, and Texas in the mid-’80s was roiled by the S&L collapse. For me, it meant long days … and nights. One evening in downtown Houston, I walked by a women’s shop and fell in love with the lingerie and a beautiful outfit displayed in the window. While dressing later that evening, I realized denying reality was impossible. I re-entered the world of closeted cross-dressing.

In 2002, I came out to the members of Helping TransGenders Anonymous (HGTA), and then joined the Tau Chi Chapter of Tri-Ess (The Society of the Second Self), who helped my wife understand my need. The lost years of fear ended, and I began making up for lost time, entering my “activist phase.” My activities over the last decade include a stint on the Unity Committee, being a co-facilitator of Tau Chi, adding the Houston Area Women’s Center to the list of Tau Chi charities, joining the Community Leaders Network Group, marching in the Pride parade, being presented with the Dee McKeller award at the Unity Banquet, giving two talks at Rice University, appearing “dressed” in public numerous times, and most recently, attending [email protected] after a LaCage aux Folles performance, as evidenced by my photo with a “La Cagelle.”

I have evolved from a repressed, confused young man for whom cross-dressing was a heady rush into a person who sees cross-dressing as a way to access my feminine side—a side valuing empathy, compassion, communication, art, and many other attributes. According to Jungian psychology, cross-dressing is a manifestation of the anima (or feminine side) that enables my personality to be more complete. (And my wife Sylvia likes to sparkle and have fun, too!)

“Life is a banquet, and most people are starving to death,” opined Auntie Mame. Try to be an involved member of the LGBT community. I am indebted to two organizations—Tau Chi Chapter of Tri-Ess (The Society of the Second-Self) and HTGA. If it weren’t for them, I’d still be frightened of buying a pair of pantyhose at the drug store.

So there’s my story: confusion, undertaking the quest, difficulty, hope, and completion with hard-won insight. My hope is that this article inspires other cross-dressers to know that they can ultimately have confidence and self-respect. You are not alone, and it gets better—but you must reach out and take the first step.

To quote a song from La Cage, “Life’s not worth a damn ’til you can say I am what I am!” And what I am is a cross-dresser!

click for More of Sylvia’s Journey



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