The Road Not Taken, Part 4

In my last several contributions to TGForum, and I do mean contributions in every sense of the word, I have been writing about the events in my life during a summer a long time ago. It was so long ago that we are now coming up on its 50^th anniversary. Fifty years have probably dulled some memories and changed some details but the ending and the moral of the story remain unchanged. During the summer of ’68 I took some steps in a direction that could have led me on a far different road in life. I guess I could have let it define my life and say, ‘that’s it I’m a drag queen’ or ‘I’m transsexual.’ However at the end of the summer I decided to take my life in a different direction. I’ll write more on that later. In the meantime we are now in to June and I’m only a few weeks from the supposed start of my summer courses at the university.

That next three weeks saw me traveling down a road that a few weeks earlier I didn’t know existed let alone think I would be on it. My new friend Linda was one of the few ‘fairies,’ as they were usually called, with a regular job and income. Most of them eked out a living any way they could which meant partly doing drag shows, partly on welfare and partly by selling themselves for sex. When I joined the gang it was assumed I’d be selling myself, too. I had not intended to do that but one night with Mel and his $50 had me thinking: why not?

If I had more carefully considered the why nots I might have considered the chance of catching a disease, the chance of being beaten up or killed and the chance of being arrested as good reasons to not take that road.

Linda had me being careful. She knew I was working at the restaurant in the evenings so she arranged for me to meet a few men she had carefully screened. Most were out of town visitors who responded to a cryptic ad in a pulp newspaper called Midnight; or was it Hush? She suggested that I only meet my dates at hotels and that I engage in a bit of sex play before taking the money as apparently police might try to entrap us girls but would not engage in sex play with one of us to do it. She strongly cautioned against us selling ourselves on the street as that was where the danger lay.

As I recall the fees varied but still gave me an extra two hundred dollars or so each week. In those days that was a big amount of money. I was due to start a full-time job in September, one that would pay me $5,900 for the first year, roughly $150/week before taxes.

Sometime in late June I found time to check in with the university. I was expecting to tell them I would not be doing studies that summer. However, despite going in to the meeting expecting to come out on one road, I took another. Someone at the college had heard of my background in camping, canoeing and the great outdoors. In the late 1960s Outdoor Education was the coming thing in Ontario high schools and lots of teachers wanted to gain a certification they could only get during the summer. The university’s College of Education had cobbled together a course and they had a lead instructor. Knowing of my summer camp background he suggested I could help. It didn’t pay as much as I was earning on my back and on my knees but it was what I wanted to do. I went in to the meeting as a hooker and came out an outdoorsman.

Linda took it in good stride that I would be putting aside my fem life for a couple of weeks to pursue my studies, teach part time and help lead expeditions on the weekends. However before we parted ways Linda had one last surprise in store for me.

Ms. Jensen when she was “Honey.”

“Pack a bag,” she said, “we’re moving in to a motel for tomorrow evening.” The next evening was going to be Thursday, June 30^th, the night before Canada’s national holiday. I would be dressed as a male to check in and we were to get separate and adjoining rooms. I did not know why but I knew enough to know that Linda’s surprises were always pleasant ones. She also told me to pack my make-up, wig, high heels, my new leather mini-skirt and a white blouse, the one sheer enough to show my bra. “And of course pack those fish-net stockings and a garter belt.”

“You want me to look like a street girl?” I joked.

Linda just smiled back. “We’re going to have an adventure,” she replied.

That next afternoon we took a taxi over to the Jarvis Street Motel and checked in. The clerk did not wonder why we were getting separate rooms. After all we had different last names and this was Toronto in the 1960s. He expected it. He might also have known Linda and of her plans for the evening.

We went to an early dinner as boy and girl. As soon as we returned to the motel Linda got busy doing my makeover. When I commented that she seemed to be ‘tarting’ me up a bit more than usual she just smiled back. “When in Rome,” I think she might have said. However, when the make-up job was done and I had on my blouse and mini-skirt, I thought I could have passed for one of the girls in Irma La Douce, a favorite movie of mine.

Linda looked equally hot with a flared mini-skirt and low cut top. She wasn’t very chesty but as tall and slim as she was she looked like a fashion model.

“Grab your handbag,” she announced, “we’re going for a stroll.”

Just up the street from the motel was Maitland St. Linda steered us there. What I didn’t know until then was that Maitland was where the street ‘working’ queens gathered to meet their clients. Linda had determined that I could not say I’d truly ‘walked on the wild side’ until I actually had been out for a walk. When we arrived there were already two other working girls slowly walking the street but they were soon in cars and off to who knows where.

“You’ll know if a man is interested in you,” Linda advised, “he’ll circle the block up to Wellesley and back down Parliament. If he stops just ahead of you he wants you to come over. After that you are on your own to use your best judgement. Some will want you just to go in the car for a BJ. Some will want more and for that you have the room. Just make sure that each guy pays extra for the room. It’s best if you let him think he is the only man you will be with tonight.”

“The only man? How many will there be?”

“This is Toronto on a Thursday night,” Linda laughed, “It is like shooting fish in a barrel or catching them in an Ontario lake which is where a lot of these guys’ wives are. How many there are is up to you.”

“But what about the cops?”

“There seems to be an understanding here in Toronto. On Thursdays the cops look elsewhere. I think it is because too many important people are out here cruising on a Thursday night. You might see a provincial politician here,” explained Linda.

“You mean picking up one of us girls?”

“No, I mean as one of the girls,” she laughed.

We split up and soon I was alone. Linda had left with a man in a Chevrolet. Another girl came along. We chatted for a while until a man was signaling me over to his car. He looked nice and his car was clean. I decided to go.

To be continued. . . .

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Tags: crossdressing, featured, prostitution, Transgender

Category: Transgender Body & Soul