The Road Not Taken: Part lll The Way It Was

I’m writing a series about my first foray in to the TG world. With acknowledgement to the poet, Robert Frost, I’m calling it The Road Not Taken because after a short time I veered off the path that lead many to gender re-assignment and a life different than they could have expected if they had remained the males they were born. But while I was on that road it was a trip I’ll never forget.

The St. Charles

In talking about the series with an old friend she shared a thought that I hadn’t considered. She said, “you know Linda many of your readers have no idea about the times and troubles of that era. Gen X’s, Gen Y’s, Millennials and the like would have no idea what it was like to live with transgender feelings in an era when it was a criminal offense for persons of the same sex to have sex with each other. That included having sex not only in a public place but also in their home. It was also an offense in most places for males to appear in public ‘disguised’ as women except on one day — Halloween.”

“And didn’t they do up Halloween in a big time way!” I exclaimed.

“Halloween at the St. Charles was big time news on the Toronto TV stations,” my friend continued, “I remember seeing TV news shows in Toronto where they would film the queens arriving in taxis to enter the St. Charles for their annual party. Hundreds of people would be there to see the men in their ‘outfits.’ It was like walking the red carpet.”

“The gals must have felt like celebrities,” I commented, “I was never there for a Halloween but I would have liked to be there.”

My friend continued, “Apparently it was a tough crowd. They applauded the gals who passed. Your Linda must have been one of those. However they could be pretty derisive towards those who didn’t make it to 100%. Then some yokels started showing up to toss eggs at the girls. That was the end of it! That was then and this is now.”

A man throws an egg at the trans folks at the St. Charles Halloween party.

My friend explained that most of the younger generations (and most of the world is younger than us two) would not think it a big deal about going to a gay bar, meeting a ‘tranny’ and having sex. Hopefully the sex would be safe sex but judging from the number of ads on Craigslist and dozens of other sites ‘taking a walk on the wild side’ seems almost a rite of passage for many young men and older men, too.

Let me explain for you what the 1960s were like for the young man who aspired to be a woman or even who felt sexual arousal at the thought of being a woman or at the touch of a woman’s clothing and lingerie.

First and foremost it was an era before political correctness. Everything that was out of the ordinary was fair game to be sneered at and mocked.

In that era male homosexuals were not called ‘gay.’ They were known as queers, fags, homos. The more pretentious in the world would call them Sodomites as if to love another man was to be the member of a cult. I knew of groups of guys in my high school who would brag about getting drunk on a weekend night and going out to find a queer to beat up.

In that era the words transgender and crossdresser had not yet been formed or at least were not in common usage.
Instead we who enjoyed feminine wardrobes would be grouped as either

• a transsexual, a rare person who went through years of tests and screening before being selected for usually experimental gender reassignment surgery. In that era transsexuals were considered to have a genetic abnormality supplying the male with an extra X chromosome.
• Or a drag queen who dressed en femme for entertainment purposes and we were told would wear male underwear because they were not really interested in being a woman.
• Or we could be classed as a transvestite, one who wore women’s clothing, usually just the lingerie, for personal sexual arousal.

That was it. There was no consideration of the concept that a person from birth or very early age could have a very strong emotional affinity to being of the other gender. Far be it for a man to just enjoy the feeling, sexual or not, of appearing and living as a woman, either permanently or in short bursts of enjoyment.
The folks of the 1960s had no concept of how wide the spectrum of the transgender world actually was. What they didn’t know they feared or mistrusted. It is called xenophobia. With the advent of the Internet and social media being so many years off in the future there were very few ways for people of like minds to get together to know that they were not alone.

In their loneliness I’m told many young people with transgender feelings dropped out of or became outcasts from their families, their communities and what should have been their closest supports.

Feeling outcast they usually left their home towns and drifted to the larger cities where they would eke out a living any way they could. In Canada the cities were usually Toronto and Vancouver if you were English speaking and Montreal for the French Canadians. The living was often as a male prostitute, model or actor in 8mm porn movies. Apparently there was a very high rate of suicide among the young transgender population of the time. Few had any chance at all to feel good about themselves.

There must have been older ‘crossdressers’ back in that era but in my short interlude in the community I never met any. Apparently there were small groups in the States centered on Virginia Prince and others who were getting together, coining such terms as crossdresser and taking some of the mystique out of our lifestyle. However they were still few and far between and the ways of spreading their ideas were primitive by today’s standards.

As I left my teen years in Canada I had no knowledge that there were any but a few drag queens playing a small number of night clubs across the country. They dressed to entertain. I had no idea that men could be dressing as women for their own pleasure.

I had my own pleasure. Sure I dated girls but I rarely got to bed with them. I had been schooled by my parents and my first girlfriend that ‘no’ meant no. I could accept that because I had regular release back at my room. The cure for any sexual frustration I might feel was masturbation. Three things brought me to climax when masturbating. One was thinking erotically about some girls I knew. Second was reading a book called Fanny Hill. (if you haven’t read or heard about it I suggest you get a copy. It is written in the style of 18th-19th century British novels such as Tom Jones and is filled with the most descriptive erotica I’ve ever come across). However my third stimulus to masturbation was my favorite. I enjoyed putting on a bra, slip and panties and playing with myself as I looked in a mirror. Climax came quickly and intensely. They were followed by short periods of regret and guilt, fortunately very short periods.

Occasionally and very privately I got the chance to dress more completely, finding old skirts and dresses in my grandmother’s closets or my mother’s laundry basket. There was also the time I dated a college girl for her dress size but that didn’t work out well.

Those were very private sessions and never involved makeup or even wearing a wig but when I met my friend Linda I was better prepared than most would be for the adventure to follow.

As my friend and I discussed our very occasional TG lives of the 1960s, our hit and miss learning and attempts to find literature on the subject she easily spotted one fact of my life. “I bet that back then there was no one, absolutely no one you would or could share your life with,” she commented, “I bet that back then no one knew about Linda.”

“You are so correct but back then I wasn’t even Linda. In fact some years later I chose the name to honor a friend of mine from that time. Whether I was in boy or girl mode she only called me Honey. So back then that is what I called my femme me.”

There you have it youngsters. And by youngsters I mean everyone under 50. Back in the day before social media it was possible to grow in to one’s 20s, graduate from one university and have one year of post-graduate at another, have self-pleasuring feelings around female attire and still know relatively nothing about the transgender culture. That I spend the next two months — only two months — so totally immersed in being a pseudo woman is amazing. It is amazing to me. However I knew that at the end of the two months I was going to have to make a choice that would determine the rest of my life and leave the discarded choice the ‘Road Not Taken.’

Next time I will resume my story. My two month growth which started with a nerdy college boy wandering in to a night club full of ‘drag queens’ and quickly moved from the boy becoming one of the girls to becoming one of the ‘working girls.’ What was to happen next would lead to one of the toughest decisions of my life. Read it all four weeks from now.

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Tags: crossdressing, featured, History, Identity, Transgender

Category: Transgender Fun & Entertainment, Transgender History