Part 3: Claire’s First Date

[Claire Part 1][Claire Part 2][Claire Part 3]

From Boy-toy to Escort in a Millisecond

It is quite strange how seemingly little things can make a big difference in a person’s life. Two women go out for dinner at a Vancouver restaurant called the White Spot. The White Spot was and is part of a chain of restaurants across the Vancouver area. No big deal: tens of thousands of people eat there every day. However for one of these women the dinner was life-changing.

The year was 1967. Claire, who up to then had been known as Calvin, sat enjoying the White Spot’s signature hamburger and thinking how much she was enjoying the feelings of the moment. She enjoyed the feeling of her skirt hem across her thigh. She enjoyed the feeling of her private parts constrained by the panties she was wearing. She enjoyed the feeling of her nylon stockings on her freshly shaven legs. She enjoyed the feeling of her bra across her back and around her chest. Most of all she enjoyed the realization that there she sat, a boy looking a bit like Sandra Dee, and no one was paying any attention. Today that is not such a big deal. People generally do not get in other people’s faces. However, in the Canada of the 1960s, gays and ‘trannies’ were still considered fair game for verbal abuse. Claire and Dale were getting no verbal abuse, not even second looks.

Dale had warned Claire that she still had a lot to learn. After the restaurant trip Claire was anxious to get back to her ‘boot camp’. Dale was also keen to resume the lessons. Actually she had never stopped. At the restaurant she had been saying things like: “Take a look around at the other women here. Observe how they sit, how they stand up and how they walk. See how effortlessly they pick up and hold their handbags. Look at the facial expressions and arm gestures as they talk to each other and how others might gesture as they talk to the man they are with. It is all part of the same package. We are going to be working on that when we get back to the condo.”

Claire suddenly felt a bit self-conscious. Dale saw the look. “Don’t worry,” she reassured Claire, “you are doing great. These are just little things that will make a difference for the men you are with.”

“Men?” Claire exclaimed quietly, “I thought this was all for one guy, you said a Hollywood big shot.”

“Girl, you have no idea. I think once I’ve finished, you will never want to hear the name Calvin ever again.”

Back to the present: “You know your friend Dale was so right about those mannerisms,” I told Claire, “It seems too many of us think crossdressing is just about dressing.”

“Well everybody has their own level and that is okay. We should accept each and every one for who they are and how they appear. But I think you and I have gone further and been accepted more than we could otherwise expect because we have both tried to embrace the whole package of femininity and not just the clothes,” my friend had replied.

Just then our server appeared in front of Claire and placed what would be her third crème de menthe in front of her. “With compliments of the gentleman at the end of the bar,” she said as she also handed over a bar coaster with a note on it. ‘Hi love. Remember me? —Sal’ the note read.

As soon as she had read the note Claire smiled and waved to Sal to come over. “You’ll love him,” Claire said to me.

‘I think I already have,’ I thought to myself as I recalled the handsome well-build, well-equipped Italian Canadian I had met once at a hotel out near the Toronto airport. ‘This should be interesting’.

“Sal, this is Linda. Linda meet Sal,”

“Actually I think we have already met,” Sal said. “Maybe it was about three years ago at the Airport Holiday Inn?”

“Yes, I remember. It’s great to see you again. How are you doing?” The small talk went on for a while. Claire thought it a laugh that we had both ‘known’ Sal. In her case it turned out to be several times.

Claire brought us back to our topic of the day, “So Sal, Linda and I were talking about there being ‘crossdressers and there being crossdressers. You are an experienced admirer. What is it that attracts you to us gals? Is there anything that turns you off?”

Sal looked at both of us as if thinking he might be about to step in to a trap. “Don’t be shy,” Claire urged, “we are both big girls and we won’t bite your head off. Just be honest. Linda needs to hear from you for some research she is doing.” I cringed at the little white lie.

“Well,” said Sal, choosing his words carefully, “you are two of the type of girls that I like.” You are the full deal. Besides dressing well you are careful with your makeup. You talk like women. You walk like women. You smile and flirt like women. I don’t feel defensive and protective when I’m out with either of you because the rest of the world is going to see us as a male/female couple.

“See,” smiled Claire, “I told you he was nice and smart. But Linda, that is what I meant about Dale saying she wanted to be sure I had the full package. I was lucky. Today the girls can get all that information through any number of YouTube videos but for us back in the day it was very much hit or miss. Dale was demanding but the results were worth it.

“As we walked back from the White Spot she had me walk arm in arm with her and match her strides,” Claire explained as Sal and I listened. “It was like learning to dance or to skate. Soon the stride was coming naturally. When we entered her condo we started up the stairs. She explained how to swing my hips just a bit and to let my butt protrude just enough to be sexy. When I had the climb mastered we turned around and walked down. “

“That’s great,” I joked, “Didn’t you say she lived about the 20^th floor?”

“We only did a few floors. My next lesson was how to smoke a cigarette. I didn’t and don’t smoke but Claire told me cigarettes were great ice breakers in a bar. If you wanted to meet someone pull out a cigarette and ask if he has a light. Always have cigarettes and a lighter in your purse. Of course,” she turned to Sal with a smile, “that doesn’t work so much anymore.”

“From walking and smoking we moved on to sitting and standing and holding my new purse. Dale told me that one of the toughest things for me to remember would be that I didn’t have a wallet and keys in my pocket. I had to guard my purse with my life but in a lady-like way.

“The next morning Claire had me bathe, shave and apply my makeup. It was just another day at boot camp. At breakfast Claire explained the importance of altering my eating habits. Women, with smaller mouths, will take smaller bites and chew completely. She told me the importance of keeping my mouth closed when chewing. She explained that for sure my first date was going to involve dinner in a fancy restaurant. Every woman there will have been groomed since childhood on proper table manners. She wanted me to fit in. More than once she reminded me to sit up and keep my shoulders back. I came to like doing that as it brought the best feeling to my bra and falsies.

“Then we met one of Dale’s male friends for lunch. My lesson for the session was how to listen to a man. We may think it demeaning and counter to women’s lib today but in those days a man and woman in conversation were just different from two men or two women. I was taught to defer and to show interest in what he was saying, not to argue and most importantly to laugh at his jokes.”

“You know I still find that useful strategy today,” I commented, “and when I know I’m doing it by choice I don’t feel as if I’m being demeaned.

“Hey, does that mean I’m not as funny as you gals led me to believe?” asked Sal. We both laughed politely. “But what I want to know,” asked Sal, “is that you both were born male and presumably went through puberty as males. So how do you get such soft feminine voices? And men when they speak their voices drop at the end of what they are saying. You are like real women and your voices go up in pitch.”

“I’m afraid were not allowed to tell you our secret,” Claire said with a wink, “it takes practice and I have been practicing since that second day of my drag queen boot camp. Dale was very good at working me through changing my pitch and speech pattern.”

At about that time Sal excused himself saying he had to get home. Thanks for that as I was anxious to learn how Claire’s first night on the town with the Hollywood big-shot went. Claire was also bursting to tell me. “Talk about going from zero to full speed in no time at all. Four days after the first time I put on a bra I was readying myself to get picked up for a date on the town. Claire had arranged that ‘Donald’ would come to the condo so we could meet; he could ‘examine the goods’ and conduct a bit of business with Claire. Then he and I would be on our way.”

According to Claire all went well and Dale sent her to ‘refresh her make-up’ while the two old friends settled certain details. All that out of the way, Claire was Donald’s for the night. They headed out for dinner at the Hotel Vancouver where Donald just happened to be staying. Claire was wearing a slim fitting sheath dress with a necklace and matching dangling earrings. She had wanted to go with higher heels but Dale urged her to stick to no more than one inch. “These Hollywood guys are not the tallest people in the world,” she laughed.

With dinner concluding, Claire expected to be invited upstairs to see something. She was in for a surprise. “We’re going to The Cave,” said Donald, “I’m meeting someone there and I think you will like him.”

Claire had barely heard of the Cave but it was THE entertainment night spot in Vancouver back in the day. Claire said she was in Heaven to be escorted to a front table in the crowded night club. If people were looking at her it was because of the man she was with or perhaps they were wondering if somehow Sandra Dee had just walked in. One woman pulled a notebook out of her purse and asked the two for their autographs but a server/bodyguard moved between them and politely asked her to return to her table.

“So who did you meet? Are you going to tell me?”

“Del Shannon.”

“Del Shannon! Really?” I knew of Del Shannon. When I was very young and hanging around the older teens his records were among their favorites. However his career had suffered as his genre of music had been overtaken in popularity by the Beatles, Motown and ‘acid rock’.

“Yes, he was playing there that week and but most of his time was spent as a music producer and Donald was interested in talking to him about doing the production on an upcoming movie. After his set he came over and sat with us. He and Donald talked about things I didn’t understand but they were getting along and they agreed to something. I remember Del saying that he’d have to run it by ‘his people’ but he was sure they could work it out.”

“Did they?” I asked.

“You know I never found out. That was my one and only brush with Hollywood business and with Donald. He wasn’t in Vancouver for a long time and I was going to have to head back to Toronto soon. My plans to visit my cousins in the States were already shot.

“So after his business was over Donald became a lot more interested in me and in getting me in to bed. We slipped out of the club and in to a cab for the short ride back to his hotel. I’ll spare you a lot of the details but he was as attentive to me in bed,” smiled Claire, “as he was to Del Shannon when they were discussing business.

“He was loving and romantic but when he was done he was done. Just as when he concluded his business with Del he was ready to move on when he had finished with me. I knew it was time for me to move on.”

“Haven’t we both seen a lot of that over the years?” I chimed in.

“I was just as happy to get back to Dale. The male Dale greeted me and he helped me reach the satisfaction I had been denied with Donald. I loved that about Dale.

“I stayed a few more days with Dale and then it was time to head home to get to school. With the money Dale had saved for me I was able to fly home. I left all my Claire clothes with Dale. Most of them had been bought by her anyway. At the time I figured that would be another closed chapter in my life. Girl was I wrong! I tell you what: you buy me dinner and you’ll hear the rest of my story.”

“Did you ever think of blowing off university and staying with Dale?” I asked.

Claire shrugged, “That might have been on my mind but Dale got me the ticket and the day before I flew out another young man showed up at Dale’s door. It turns out I had been the summer fill-in for Dale’s regular young boy-toy who had been out of town on a summer job, now returning to studies by day and escort work by night. When we all went to bed Dale and his regular slept in the master bedroom. I slept alone in the other room. It was a good message for me to get out of town.

We headed to the Delta Chelsea’s dining room and if you think you have heard a strange story up to now come back in four weeks for more twists than a New York pretzel.

To be continued….

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Tags: crossdressing, featured

Category: Fiction, Transgender Fun & Entertainment