Retro Rerun: To Tell or Not To Tell. . .

Memoirs of a Transgendered Lady 1996: “To Tell or Not To Tell”

By Roberta Angela Dee

On several occasions, I’ve dealt with the issue of whether or not to tell a gentleman that I am a transgender woman. What I share with you ladies here is only one of several such occurrences.

I began living as a woman in 1981 while still living on Long Island. I had not had surgery of any kind, but had a distinctively feminine figure from having already taken a combination of female hormones — Premarin (estrogen) and Provera (progesterone) for three years.

In 1984 Ronald Reagan was President of the United States of America, Vanessa Williams was Miss America, Amadeus was a favorite film, and I moved to Westwego, Louisiana to begin my first job as an independent subcontractor for an electrical generating station still under construction.

I arrived in Westwego in October, 3 months before Mardi Gras or “Fat Tuesday” as it is sometimes called. The facility where I was employed was 40 miles away in another town, or parish, as they’re called in Louisiana.

The most wonderful aspect of being an independent contractor was that no one cared if you were African- American or white, fat or thin, or male or female. All that mattered was that you did your job and got the job done on schedule.

At the somewhat muddy construction site, I typically wore tight Western jeans and a white Poet blouse — a distinctively feminine combination, when you considered my environment. We worked 12 hours a day, and usually, 7 days a week. Yet, I somehow managed to find time to take the drive from Westwego and over the Mississippi River Bridge, to spend some time in The French Quarter where people from all over the planet came to party all night long particularly during Mardi Gras.

At this time, I’m 32 years old 6 feet tall, weigh 155 pounds (very slender) and I measure 40B – 30 – 40 — what I measure today, although I’ve added a few pounds. Still, I “passed” easily and had no problem on the streets of New Orleans. Nor did I have a problem showing off my breasts from a tavern’s balcony for the crowds of intoxicated males on the grounds below. They loved the exposure, and I loved the attention.

On one particular evening, I was dressed to attract even the most docile male beast. I wore knee-high shiny black boots, black hose, a white pleated mini skirt, and a white military style jacket opened enough to expose a generous amount of cleavage. And, ladies, did I ever get the guys attention.

Tourist and native residents of New Orleans are sashaying down the streets with alcoholic drinks in hand, singing and laughing — with several couples dancing — and everyone having a gay old time. It’s one o’clock in the morning and I slip into a bar called “Papa Joe’s” that caters to a mixed clientele of gay, straight and transgender people. No sooner than I sit at the bar and order a black Russian, a young man of apparent German descent approaches me and offers to pay for my drink. He’s cute as a button, but I tell him that I’m just cruising and couldn’t impose on him, as I had no intentions of staying more than a few minutes. But he politely insisted and I graciously accepted.

His name was Andy. I cannot recall his last name. And, if I was to meet him tomorrow, I would not know who he was. What I do remember of him was his dirty-blonde hair and that he had one blue eye and one green eye. This alone made him fascinating to gaze upon. But there was more than his hair and his eyes. He was a marvelous conversationalist, but also took the time to ask questions about me and to listen to my replies. Each gesture spoke of a gentleman cavorting about a lady. And that was the quality about him that appealed to me most: he never once treated me as anyone less than a perfect lady. And even in my rather sultry attire, I played the part as best I knew how.

Already a few minutes had become an hour. And so, when he invited me out to an early morning breakfast, again I accepted.

The waitress, I believe, assumed that I was just another girl picked up by a stranger to be a companion for a night. Still, she was professionally polite, as her position demanded.

Since we were in a very public place, I was less fearful of him reacting in any way that was hostile. So I merely told him that I was a transgender woman, that I was born a male but had been taking hormones for several years. I also told him that in the masculine sense I was impotent, but liked both genders — male and female.

I told him because I firmly believe that every relation, even one fated for a single evening, deserves to be initiated on an honest footing. More importantly, if he truly liked me for my personality, then my real or perceived gender should not matter.

He had invited me out as a gentleman invites a lady out for the evening. And I provided the companionship of a lady. So, the only question of important should be whether or not we would become intimate.

In this instance, the gentleman had already suspected that I was transgender. And since he himself was bisexual, it did not matter to him.

On other occasions, the gentleman did not know and was astonished to discover my secret. Fortunately, I’ve always been careful about the demeanor of the individual with whom I’ve conversed. And, I’ve always selected a public place to reveal my secret. On a few occasions, the gentleman expressed some measure of disgust and left me to foot the bill, but mostly the outcome has been favorable.

That evening, Andy and I made love, and it was a beautiful exchange of physical passion and emotional eroticism. Some might say it was affair between two men. Others might concede that for all practical purposes, it was a man and a woman.

I do not write to convince you one way or the other. This is simply my story for you to judge however it pleases you.

Like to make a comment? Login here and use the comment area below.

Tags: featured, partners, passing, Transgender

Category: Transgender Body & Soul