Confessions from a Cross-Dresser Convention


Anyone who knows me knows that I am a sucker for unique people and experiences. Add to that, I’m somewhat outgoing, uninhibited, and I love to learn why people do the things they do—all traits I’m thankful were bestowed upon me from birth. They make for many exciting opportunities and life experiences.

Enter Cincinnati, Ohio, 1996. I was staying in a Holiday Inn on the east side of town, enroute to another Ohio destination, when I happened upon a perfect opportunity—an annual cross-dresser convention was taking place at our hotel! After getting the kids into bed (5 and 2 at the time), my ex-husband, supportive of my inquisitive streak, pushed me out the door and told me to carpe diem (seize the day)!

Living my whole life only in Wyoming and southwest Florida (home of the conservative senior citizens), I had very little cross-dresser experience to go on. Admittedly, I carried assumptions (judgments) about them, and I hoped to find out if any were true. For starters, I thought cross-dressers were committed to the lifestyle 24/7, that they wanted to be women, that they may in fact be homosexuals, and that they were probably doing it, in part, for attention or the novelty of it.

My first impression when I walked into the lounge area where many were socializing for the evening was, “I have never seen an uglier bunch of women in my life!” It’s not that the men themselves were unattractive, but they sure could have used some hair, wardrobe, and makeup tips! These were far from professionals, I could tell that right away. Most of them were decked out in gaudy jewelry, flashy, flamboyant colors and tacky clothing combinations, and horrendous makeup application. I saw everything from black net stockings and BIG HAIR blond wigs, to high heels and neon red lipstick (actually, they all had on high heels and were far from graceful or at home in them).

The “gals” seemed readily willing to accept a stranger in their midst, so I sat down at the bar and began conversing. I asked questions and listened late into the night. Larry-Kimberly, a plumber, was a happily married man with two kids who hid his once a week cross-dresser habit from his family. I asked him where he kept his weekend paraphernalia and he told me he kept it hidden in trash sacks in the back of a closet.

Thirty something Todd-Joyce, a police officer, told me he used to be a pole vaulter on his college track team, and he still had the physique—barely concealed under his frills—to prove it. He too was married and had no intention of expressing his feminine side more than once a week.

Of all the “gals” I visited with that evening, not one of them was a homosexual (not that it would have mattered), but were all married men sworn to secrecy. When I asked what they told their families as to where they went on the weekends, it was usually “golfing” or “to a sporting event” (you wives should think about that).

Not one wanted to be a woman but merely did the cross-dresser thing as outlet for their mischievous, risk-seeking, adventurous natures, without doing anything particularly damaging to themselves or their families. I’m not suggesting that their lying to their wives was the right thing to do, but I’m just saying that they could have been out doing a lot worse things. And though it was a long time ago, and I’m probably missing many fantastic, juicy details, each one had an engaging, multi-dimensional story to tell of their life as a regular Joe.

Hanging out with cross-dressers gave me yet another opportunity in life to learn about people, and how I have misjudged them or misunderstood them. I still think I was right that many of them did it for the novelty and perhaps the attention, but I found out that my previous judgments were mostly wrong.

I also found out that, at the core, they are not much different than me. After all, they weren’t the only ones sitting in a hotel at a cross-dresser convention.

"Gloria" the fantastic babysitter (see comments)

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