Part II Claire Emerges

[Claire Part 1][Claire Part 2]

It seems like only a few weeks ago that I told you about my Toronto friend Claire and how back in the 1960s living as Calvin he had hitchhiked across Canada only to find himself homeless and broke on the edge of Vancouver. Calvin had been picked up by a ‘handsome stranger’ who took him to his apartment and gave him a place to stay. You know the story. I don’t have to re-tell it. Suffice it to say that soon Calvin found himself in the murky world of male prostitution working for a sometimes drag queen named Dale. However Calvin did not find the world murky. He enjoyed the attention the older men gave him. He enjoyed the conversation, didn’t mind the sex and loved the money he was earning. That is all Claire could tell me before she had to leave to meet her friend of the evening.

“Contact me tomorrow and when we get together I’ll tell you how Claire came in to it,” were her final words to me.

Needless to say I could hardly wait for the tomorrow to come. I texted Claire about us meeting. I did not hear back for a while but when I did we set it up to meet at the Delta Chelsea Inn.

I love the Delta Chelsea Inn. It is a large full service hotel favored by business and government travelers who often unwind after work either in the gym, the rooftop pool or the lounge, three places this gal hangs out. The Delta Chelsea Inn is also close to Toronto’s lively gay district which by the way is centered on Church Street. You know what they say about Toronto: “all the churches are on Queen Street and all the queens are on Church Street”.

That may be true but this particular afternoon Claire and I, who could be called two old queens, were at the Delta Chelsea. In deference to the business crowd I was wearing a sheath dress and jacket. Claire appeared wearing a skirt and blouse, walking so smoothly in two inch heels. We noticed each other about simultaneously, she at the entrance, I sitting at one of the high tables playing with my iPhone in my lap but really studying the crowd to read if anyone was reading me. No one was.

Just as the server delivered my glass of chardonnay, Claire reached the table and ordered her crème de menthe. Did I tell you that gal had class?

“So, how was your date?” I asked innocently, knowing as soon as the words were out of my mouth that she was going to make a short story long. I will spare you a lot of the details Claire shared with me but one thing you may find interesting is that Claire’s date, a man in his 60s was once one of Toronto’s most popular crossdressers, if it is possible for a CD to be popular. He was one who had lots of friends in the community but one day about four years earlier, as he studied the wrinkling of his face and the sagging of his belly, he decided that he could no longer achieve the beautiful image he wanted to see in himself so he just gave it up. Cold turkey he gave up dressing. He still loved going to the swingers’ club and he still loved making love with the t-girls but he just did not get turned on by the thought of his own feminine image. Several months back Claire and her friend had decided that they should be regular dates at the club.

“I knew a t-gal like that once,” I chimed in. “She was from Australia. One year she went to the Southern Comfort Conference in Atlanta. She was getting on a bit in years. She looked at all the American beauties at the SCC and decided that she could no longer measure up. When she got home she rarely dressed and went out again.

“But let’s stop talking about the end game,” I said throwing in a chess analogy, “What about you? You promised to tell me how you got started dressing and so far all you’ve told me is that you were a boy whore in Vancouver one summer.”

“A teen escort, if you please,” Claire corrected me with a smile. “It’s all part of the same package. When Dale told me how much money I had earned in less than three weeks and told me I could earn just about that again in a few nights if I were to meet a few guys in drag, or en femme as we call it today.”

As the server delivered her second crème de menthe Claire started to recount her first encounters with Dale and his ‘friends’. I will spare you all that detail. The short of it was that Dale had a special friend coming in from California. He had expressed an interest in meeting a young passable ‘drag queen,’ if one could be found.

“Was he in the entertainment business?” I asked, thinking of one particular actor of the time who was now reputed to have been a like time cross dresser.

“He was and you would probably know his name but he was not in front of the cameras. Don’t bother trying to guess because even to this day I would not tell you.”

“Not Harvey Weinstein?” I joked.

Calvin dressed up looked a lot like actress Sandra Dee.

“No, I would not have touched that greasy, fat son of a bitch for any amount of money but no this was way before his time.”

I let Claire continue and finally she got around to telling me about her transformation, “Dale insisted that if I was going to date her friend I was going to do it in style, no half measures.”

Claire went on to explain how Dale meticulously transformed her in to an outward feminine image. ‘The inward part has to come from you,’ Dale had told Claire, ‘but I’m confident it will come as you see the new you emerge.’

Claire tried to make it sound like an easy gentle process of transformation but in reality it must have been ‘Drag Queen Boot Camp.’ Claire had to master in two or three days what many of us have taken years to learn.

Of course there was:

• the hot foamy bath to soften her skin
• removing most of her body hair, leaving only a short, shaped patch of pubic hair
• learning to shave her face really close first by softening the beard with hot towels. She learned how that brought the hair roots closer to the surface. She had shaven with the grain of the hair and then against it. “You should be able to rub your fingers upwards across your cheeks and chin and feel no hair,” Dale had taught her.
• She learned how to put on a bra, stuff it and insert foam rubble ‘falsies,’ a staple of every crossdresser and many women in that era before silicon breast forms. It was in putting on the bra that Claire says gave the first inkling of arousal. Dale even showed her how to uses some sports tape to pull her chest together under the bra to create the illusion of cleavage.
• Dale taught her how to wear panties and a garter belt. “The garter belt always goes on first,” said Dale, “that way it is easier to take off the panties if you need to.” That explained to Claire why Calvin’s girlfriend had always worn her garter belt on the outside. Garter belt? It might as well have been a chastity belt!

Claire was really enjoying it by the time she slipped on her first slip. When she looked in the mirror she saw what looked like a woman’s body with the cleavage screaming out from under her slip. But from the neck up it still was the same old Calvin.

That didn’t last long. “Here, sit,” Dale said as she motioned to a chair in front of a table and large well-lit mirror. Claire was not sure how long they spent but it was at least the better part of the day. Apparently Dale believed that if you give a gal a makeover she has a nice make up job for an evening. Teach her to apply the makeup and she will be gorgeous for a lifetime.

Again the lessons were step-by-step and meticulous. Dale sat beside Claire and showed her the importance of moisturizing, then picking and applying the right shade of foundation. She plucked a bit at Claire’s eyebrows then showed Claire how she could give them a feminine shape that would not ‘raise others’ eyebrows’ when out as Calvin. They spent a lot of time with eyeliner, mascara and eyeshadow. Frosty blue was a popular shade of eyeshadow at the time, Claire said. I knew that but I had learned the hard way that frosty blue eyeshadow does not go very well with frosty blue eyes. Her lipstick completed the look. “Never, ever, ever, ever be dressed as a girl and not have lipstick on,” Dale had told Claire.

Claire said she had found it tough to get the hang of using the eyeliner pencil and even the mascara brush but Dale was a great teacher and with each success she would give Claire an encouraging squeeze between her legs. Wearing lipstick came naturally to her.

Finally Claire was ready for her crowning glory, the wig. Actually I don’t know if it was a Crowning Glory wig but apparently when Dale showed Claire how to put it on and Claire took yet another look in the mirror she says she thought Sandra Dee was looking back at her.

Dale then gave Claire a blouse and skirt to wear. The blouse was relatively easy but our Claire had to be shown how the skirt zipper was placed to her rear. Dale also showed Claire how to ‘blouse out’ her blouse so that it was not tucked in tight to her skirt. Claire immediately liked the look.

“You look perfect,” said Dale, “Our friend likes young blonde women and you definitely fit that image. Let’s get a bite to eat and then we’ll continue with the lessons.”

“There’s more?” asked Claire as she looked in the mirror and saw what she though was a gorgeous girl looking back.”

“Yes, there’s more. We have only dealt with the surface but you are ready for your first visit to a restaurant. Come on. Pick up that purse and let’s go! Oh and clip on these earrings. They’ll look great with your dress.”

Before Claire could think about it the two gals were out of the apartment, down the elevator, on to the street and off to the nearest White Spot restaurant. She was glad that for her first trip out Dale had fitted her with a pair of low shoes, hardly any heel at all. But even with that Dale was offering advice that perhaps she would want to take shorter strides.

The White Spot restaurant today: Different facade, same great service.

The dinner was uneventful but delicious. The two gals attracted little attention. The waitress apparently knew Dale but was careful to say things like ‘what would you two girls like for desert?’ This short outing gave Claire the confidence to know that with a little more practice she could be comfortable and totally passable on the street or on a date.

Next time: the lessons continue and the Hollywood big shot arrives in town.

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Tags: crossdressing, featured

Category: Transgender Fun & Entertainment