A Life’s Strange and Sudden Turn

I met Claire under extraordinary circumstances. That was fitting as she was/ is an extraordinary person and she had an extraordinary story to tell. If only part of her story is true I would still be amazed.

Up in Toronto, Canada there is a club where swingers — those in to the ‘adult lifestyle’ go to meet and play. It is not in someone’s house. It is not in some poorly lit warehouse area. The club is located in a strip mall on one of the busiest streets in one of the trendiest areas in Toronto. There is a street car stop right outside the club’s front door. Well, okay when I say it is in the mall only the front door is at street level. The club name is discreetly marked and to access the club one must go down a flight of stairs.

Six nights a week and many afternoons, too, the club caters to various combinations of swingers –- couples, cougars, threesomes, bi nights -– they have it all and all includes ‘Trannie Tuesdays.’

Naturally Claire and I found ourselves there on a Tuesday night. We both fit somewhere on the TG spectrum. I call myself a crossdresser. Circumstances have made me determine that I do not want a gender transformation but I enjoy presenting and acting as female and feminine as I can and that includes the thrill of finding men who find me attractive. When I’m in Toronto I find them at the club.

Claire on the other hand is living full time as a woman and has for years but she has not gone through any of the surgical procedures. I’d call her not pre-op, not post-op but a non-op TS.

It’s hard to tell when we gals are wearing heels but I’d say that Claire is about 5’ 8” tall and a relatively slim build. She is elderly, probably in her 60s but so am I and that is probably what brought us together. Club dating is usually a younger gal’s game but there we were, both holding our own.

The club is huge. It has a spacious lounge area with bar, dance floor and relaxation area where members and guests can chat, size each other up or just relax and ‘re-charge the batteries.’ The ‘back rooms’ are the areas where consenting adults could go to play either privately or on open cushion areas. There is even an S&M play area.

I was sitting out in the lounge having a moment of re-charge when Claire came over to sit beside me. We exchanged first names and a bit about where we are from and what brought us to the club. My explanations were short but Claire was in a mood to talk especially when she found out that we both go way back and we both had come through the AIDS plague of the 1980s unscathed.

All of that is pretty standard stuff. What made Claire unique to me was her account of how she came to be living as a woman.

Imagine for a moment the scene. We were sitting in the lounge area of an ‘adult play’ club. Every so often a hot man would walk by wearing nothing more than a modest towel wrapped around his waist. That met a club rule -– no nudity in the lounge area. I usually like to check out the hot men but this time I was so involved in Claire’s story I hardly noticed them.

I have struggled a bit with how to retell the story to you. It would be pretty well impossible to recreate the dialogue. I remember what Claire told me but not how she told it or even all the questions I asked. So I’m going to try telling it in the ‘third person.’ I will be talking about Claire but not to Claire. When there is dialogue it will be me writing what Claire says was said at the time. Got it? Here goes.

It was late spring 1967, Canada’s centennial year. Calvin (a pseudonym) was restless for adventure. He decided that as soon as his last high school exam was finished he would hit the road hitchhiking from Toronto to Vancouver and then down the Pacific coast to California where some cousins would greet him. He then hoped to take a train through Chicago back home to Toronto. Calvin had always been a good student and he was confident that his provincial exam results would get him in to U of T.

It seems a lot of young people were hitting the road that year and in those days many drivers seemed willing to help them on their way. So true to his word with a few hundred dollars in cash and travelers’ checks Calvin was on his way west. His parents were not too happy to see him go but they trusted their son. I’ll spare you most of the details of his journey across the country. However I did enjoy Claire telling about crossing the Canadian prairies, visiting the Calgary Stampede and Banff National Park. It seems his trip through the Rockies was a bit hair raising as one ride came from one drinking driver and another from a pastor bent on creating one more born-again Christian/saved soul.

One thing young Calvin discovered was that even when hitchhiking and camping one has to eat and occasionally find a place to stay and clean up. Visiting the Stampede and other tourist attractions were not free. So it came to be that about 100 miles east of Vancouver, near a town called Chilliwack, Calvin found himself pretty well tapped out. He knew that when he got to Vancouver he would not have money for a meal or a place to stay. It seems funny today but in all his life young Calvin had not heard of soup kitchens or homeless shelters.

Calvin thought of staying in Chilliwack to look for farm or berry picking work but decided to press on to Vancouver. It took a while for his ride to come along and when it did Claire says she should have been suspicious. The driver in the new looking Mustang had passed Calvin and given him a bit of a look then turned around, drove past in the other direction, turned again and this time pulled to a stop by Calvin.

“Where are you going?” the driver asked.

“Vancouver.”

“So am I. Hop in.” Calvin loaded his back pack in to the back seat and slid in to the passenger seat.

“Nice,” was all he could say as the driver accelerated the Mustang toward Vancouver.

Claire said that on looking back at their conversation was innocent enough. The driver who introduced himself as Dale seemed genuinely interested in Calvin and his adventures crossing the country, about his high school days and about his plans for the future. Calvin had thought it normal when Dale asked if any drivers had made passes at him. “No they haven’t,” said Calvin. It occurred to him afterwards if he’d added that ‘if one of those queers did try anything he’d kill him’ the ride and everything would have turned out very differently.

As they approached Vancouver Dale asked Calvin where he would like to be dropped. “I don’t know,” Calvin replied, “I’m all out of money. I don’t have a place to stay or food to eat. Do you know where I can find some quick work?”

“Don’t worry about that,” Dale replied, “You can come stay with me for a while. I’ve got plenty of room and you look like you could use a good meal and a shower. Would you like that?”

“I would but I don’t want to impose on you,” Calvin said while thinking there was nothing he would like better than to impose on his new companion.

“Then it’s settled. You will be my guest tonight and then we’ll see what happens. I just have one stop to make and then we’ll be at my place.

After a stop to pick up groceries and what looked like a couple of bottles of wine. Dale and Calvin arrived at a nice looking apartment building in downtown Vancouver, not far from Stanley Park.

“Home sweet home,” said Dale, “Bring your bag and I’ll carry the groceries.”

The two made their way to one of the top floors where Dale’s apartment had a gorgeous view overlooking Vancouver’s harbor. “Nice,” Calvin said again.

You probably know how all this is going to unfold so I won’t bore you with a lot of details. Suffice it to say that Dale convinced Calvin to take a long warm bath while the host put all Calvin’s clothes in the washing machine. Then while Calvin bathed Dale poured him a large glass of wine and started to cook dinner.

When Calvin finished his bath and had shaved with a razor Dale provided he found a pair of slippers and a plush robe waiting for him. “Your clothes will be ready soon but in the meantime we can’t have you running around naked, can we?” said the host who by this time was wearing a matching robe and slippers except Calvin’s robe was pink, Dale’s was blue. Do you get where this might be going?

Clair told me that the dinner was fabulous and the wine, two bottles worth, went down easily. Dale seemed genuinely interested in young Calvin’s life, again asking about his parents, his schooling, plans for university and if he had a girlfriend. Calvin reported that there was no girlfriend at present. There was a girl that he had been dating but they broke it off when both decided to attend different universities and Calvin had told her he wouldn’t be sticking around for the summer.

“Do you miss her” Dale asked.

“Not really,” replied Calvin, “We had great times and she is the only girl I’ve had sex with but I was never over the moon in love with her. How about you? You must be married?” Calvin continued as he patted the pink robe.

“No I’m not married and probably never will be. I’ve never found a woman that interests me that much. I just keep that robe for special guests,” said the host as he reached over and patted Calvin’s hand.

“I’m glad I’m special and I’m so glad you invited me to stay. I don’t know where I would be if I wasn’t here,” Calvin smiled as he nervously let Dale’s hand rest on his.

At this point I interjected that I guess Claire knew that Dale was going to ‘try something’ and how had young Calvin felt about it?

“Oh, I was pretty sure he was going to try something, as you call it and I was pretty sure I was going to let him. What was the alternative? I was homeless and broke. If he wanted to play with me and I said no I could find myself out on the street. I had nowhere to go and as I think back I don’t think there was anywhere else I wanted to be. I was enjoying the attention of an older man who seemed very interested in me. I didn’t know it at the time but I was being seduced,” Claire replied.

It was Calvin who suggested that he was tired and asked if he could go to bed. It was no surprise to him when Dale said there was only one bed available and would Calvin mind if they slept in the same bed. Calvin didn’t mind.

Getting in to bed Calvin wondered what Dale would want to do. Would he want to kiss? Would he fondle his penis? To Calvin’s surprise the older man simply said goodnight and turned off the light. Soon Calvin was fast asleep.

At some point in the night Calvin found himself dreaming. He was back in time, the summer before. He was at his family cottage and his girlfriend was visiting. They had slipped out during the night to go for a moonlight swim out to a raft. There she had proceeded to give him oral sex, a regular event between them whenever there was a risk of her getting pregnant. It was a great dream and it felt great. Only as Calvin awoke he realized it was not his girlfriend but Dale that was down on him.

“Hello, sleepyhead,” Dale interrupted his oral massaging, “would you like me to stop?”

“No, not if you don’t want to,” Calvin replied, “that feels good.” It was a comment that sealed his fate.

Dale continued his oral play and Calvin continued to enjoy it right up to his inevitable climax. As Dale got up to visit the bathroom to clean up Calvin briefly considered bolting but fatigue took over. He fell back to sleep.

When Calvin awoke he had no idea what time it was but full daylight was streaming in through the bedroom’s partially open curtains. He heard Dale busy somewhere in the apartment. After a quick visit to the adjoining bathroom Calvin slipped on his robe and went looking for Dale. By this time he had determined that he would not say no to another blow job.

However he found Dale busy in the kitchen. Only this time it was more a ‘Dale Evans’ than a ‘Dale Robertson’. Dale was wearing a skirt and blouse, heels, a wig and full make up.

Calvin knew about drag queens. He had heard about the Hallowe’en parties at the St. Charles back home in Toronto. He had just never expected to meet one. “Look at you!” he exclaimed.

“Oh this is just a little something I throw on when I’m in the mood,” said Dale, “Are you surprised? Do you like?”

“I guess I’m surprised but you are quite pretty,” Calvin said. His surprise was that he had actually felt and said that.

“Here, sit down. I have made you breakfast. Then there is something I’d like to discuss with you.”

It was already about noon. Calvin was famished. He had no problem putting down his large plate of pancakes and sausage. Dale restricted ‘herself’ to toast and coffee.

“Your clothes are cleaned and they are laid out in the second bedroom,” Dale finally commented, “You are welcome to pack and leave or you are welcome to stay as long as you would like.”

“Thank you so much. You know it seemed like a dream but I enjoyed what happened last night,” replied the young man. He wasn’t aware that what had happened between them, two consenting adult age males, was still technically illegal in Canada but even if he had been it would not have mattered. It felt good for him.

“I enjoyed it too,” smiled Dale.

As Calvin entered the second bedroom he discovered two things. One was the available second bed, no surprise there, he thought with a smile. The other was a crisp new centennial souvenir $20 bill sitting on top of his newly cleaned clothes.

Twenty dollars was a fair bit of money back in those days. It would probably last him for close to a week on the road but he felt he should decline it. Dale had done so much for him already. He returned to the kitchen with the $20 in hand.

“What is this for?” he asked. “I can’t accept this. You have done so much for me already. I’ll get by.”

“No. It’s yours. You earned it. You earned it by letting me have sex with you and if you are interested there is a lot more where that came from.”

So there it was. Dale was seducing Calvin for the purpose of recruiting him in to male prostitution. Calvin could have run but instead he asked, “How much more?” It was too late to protest that he wasn’t that kind of guy. He had let a virtual stranger go down on him and he had just slipped a $20 bill in to the pocket of his robe.

“Well you could make several hundred dollars a week by meeting with select friends of mine. You can stay here and all friends will be approved by me. Want to try it?”

“I guess it couldn’t hurt to try.” Just as easily as that Calvin had decided to prostitute himself.

“Well there are a few things you will have to learn, some for your own protection and some for pleasure.”

“Like what?”

“You are going to have to learn to fake pleasure even if you don’t feel it. You are going to have to learn how to give oral sex, deep oral sex but mostly my friends will want you to be a nice guy who will be happy and respectful.”

I won’t go in to a lot of details but Claire told me that for the next several days Calvin met a number of men, obviously wealthy men who expressed pleasure in his company. Calvin had always been comfortable with adults and that came in handy as he talked with his ‘dates.’ It seems the city had a large number of men who enjoyed the sexual company of older teenage males. Claire said it was as if they were a cult. It also seemed that a lot of these guys had originally been exposed to man-teen sex when they were the teens and the experience had been their first sexual awakening. Claire said many were married but they enjoyed occasionally going back to their sexual roots.

Claire said that after a few days she had asked about her earnings. When Dale told her how much she had earned she knew she already had enough money to complete her trip and get back home. However she decided to stick around a bit longer.

“But what has this got to do with you becoming Claire?” I asked somewhat impatiently.

“I was just getting to that but now it is going to have to wait,” she replied as she nodded toward a man that had just entered the lounge.

“Look, I’m going to have to break this off,” continued Claire, “My date has arrived. Here’s my card. Contact me tomorrow and we’ll set up a time to get together. I’m finding it a bit therapeutic to be telling this story so I enjoy talking with you. I like that you are not passing judgement on me.”

Passing judgement? Internally I thought she was just playing me along. How could all of this have happened? But on the other hand it was the 1960s. It was a more carefree time and many of us young men did not go out in the world as well prepared and defensive as the young are today. I determined that I would get together with Claire and learn the rest of her story.

But look gals. I have taken up too much of your time already. Come back in four weeks so I can tell you how Dale converted Calvin to Claire and changed his life forever.

To be continued…

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Tags: crossdressing, featured, Identity, Transgender

Category: Transgender Body & Soul, Transgender Fun & Entertainment