A “T-girl” in a Gay Fraternity

| Feb 8, 2010
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Linda JensenI had never met Claudia before that evening she joined me in the restaurant at Toronto’s Delta Chelsea Hotel. We exchanged messages after seeing each other’s ad on one of the free dating services offering a variety of contacts including the T4M category. We were both Ts advertising ourselves for Ms in the Vancouver, Canada area. That turned out to be a bit ironic as we both lived in eastern Canada, Ontario to be exact.

Claudia walked in to the restaurant not as if she owned the place but certainly as if she belonged. She asked the hostess for Ms. Jensen and was pointed in my direction. No heads turned and there were no unusual gesturing from one diner to another. One man’s eyes did follow her but it was obvious his interest did not extend above her legs and derriere.

I resisted the male inclination to rise to greet her. I extended my arm. “Claudia?” I asked.

“Yes, Dr Jensen, I presume?”

“Just Linda, I smiled, “How are you? Did you have any problem getting here?”

“No problem at all. I did get a last minute call from my daughter but since I’ev retired and come out to my family things are going a lot easier for me.”

We exchanged small talk about our families and who knows what, about how they react to knowing that one of the most successful male images in their lives has a strong feminine side.  We agreed that it goes well if it is kept on a need to know basis. No one else needs to know the strong sexual or bisexual side that each of us has.

“So how did Claudia come to be?’ I finally asked.

“Well I had an interest in women’s clothes for as long as I could remember.  I had loved secretly putting on my mother’s grandmother’s and sisters’ clothes. But in my teen years it became more a case of trying to find something that fit. I was getting to be a big girl. I also got busy with sports and dating girls so I put it all aside.

“It bloomed again in the early ’70s when I came here to Toronto to attend university and play football.”


“Yes. In my freshman year I didn’t get to play in any games but I was on the practice squad. I enjoyed the experience and it got me in to one of the more prestigious jock fraternities.”

“Which one?”

“Phi Delt.”

“I’m a Sigma Chi.”

“It gave me a good place to stay and a steady diet of interesting female companions who unwillingly let me fondle their undergarments – but only when they were wearing them or as I helped them to undress.”

“Ohhh, Tiger,” I said mockingly.

“The summer after my first year I stayed in Toronto for a job working in a bank down Younge Street. Here is where it gets interesting. One Friday evening I was walking up the street when I saw a guy I recognized from one of my classes getting out a taxi with a very pretty girl and going in to a bar. But it was not just any bar; it was the best known gay bar in Toronto.”

“The St Charles?” I asked.

“Yes. You knew of it?”

“I’m older than I pretend to be. Yes, I knew of the St. Charles. I even went there a couple of times.” I started to see where this was going as she mentioned the bar that was famous for its Halloween drag parties.

Claudia told of how he had followed his classmate and the friend in to the St Charles, eventually catching up with them in an upstairs dance hall. Claudia, then known as Claude, asked to join the couple and was welcomed. As they chatted it became apparent that the couple were just friends but also that the girlfriend was really a guy friend in drag. This revelation would have sent many jock football players out the door as fast as one could say ‘hup-one-two-three’ but not Claude. He stayed. He danced with the “girlfriend’ and got to meet a number of the other girls at the party.

“I was not freaked out at all,” said Claudia, “in fact I was really turned on by Marie. Of course my personal interest in women’s clothes helped my level of comfort. I was fascinated that a guy could look so good wearing a girl’s clothes.

“As the evening wound down they invited me to share a taxi with them back to ‘the house.’ I agreed and we made our way to a beautiful home up on Bedford Road, not far from Varsity Stadium.

“The Phi Kap house was there.”

“It wasn’t far from them but we were up the street on the opposite side.”


“Well I guess I got a bit ahead of myself but the short version of it was that evening I had my first T-girl sex experience with Marie and I loved it. She took off her dress and slip but left on her bra, garter and stockings. She also kept her wig and make-up on. We showered together and she made sure all our private parts were well cleaned. I was surprisingly comfortable handling her little penis. She introduced me to the pleasure of giving oral and anal sex.  When I did penetrate her it didn’t take long for me to climax.”

“What did you do then?”

“I must admit I did feel like leaving but Marie convinced me to have a sleep. I dozed off and did not wake up until the next morning. When I woke there was another guy I recognized from my history class. He was offering me a cup of coffee.

‘Good morning lover’, he said.


“Marie? I asked.

“Well in this mode I’m Mark but yes and thanks for the great time last night.”

“All I could say was ‘you’re welcome.’

“And welcome to the Gamma Alpha Upsilon house,” he replied.

“I thought I knew the names of all the fraternities at U of T but I’d never heard of Gamma Alpha Upsilon. They were an unofficial fraternity and not members of the IFC.”

“The Inter-fraternity Council?”

“Yes and they were not recognized by the university, either but that did not bother them. This was in the days before Stonewall and gay pride took over.”

“What do you mean?” I asked

“Gamma Alpha Upsilon (the Greek letters are pronounced “gay”) was an all gay fraternity. It’s a long story but a Toronto businessman who was very wealthy but also a very closeted gay had a strong interest in the well being of certain U of T students who were from time to time being persecuted and run out of their housing. So he offered to buy and set up a ‘safe house’ for gay students on the condition that it cover its expenses and that the students be responsible for its upkeep. In return he was very well treated when he dropped in” Claudia said with a wink.

“GAY, that’s clever,” I said.

“It sure beat Phi Alpha Gamma as a choice for a name,” she winked.

“Tell me more.”

She continued, “On the outside the GAY house looked not much different from any other student boarding house except it was better maintained and on the inside it was immaculately decorated. We’re talking gay here.”

“So where did it go from there? Did you see them again?” I asked but I pretty well knew the answer.

“My night with Marie had rekindled my own interest in crossdressing. I stayed there all the next day and finally got up the nerve to ask Mark if I could try on some of Marie’s clothes. He agreed and by the time we were done he had fully made me over. It looked a little rough because I hadn’t shaved in a day and a half and I had a lot of body hair showing but I was still very turned on.

“For the rest of the summer I would return at least once a week to the GAY house where Marie would make me over and we would have sex. It never seemed like gay sex to me as my partner was always at least a bit en femme.”

“Were there any other crossdressers there?” I asked.

“It’s funny that term hadn’t come along yet but it kind of ‘retro-fits’,” she smiled. “Yes, well more accurately there were gay guys who did drag. It was much more common to be femme in the gay community then than it is now.  So a lot of the residents would do some dressing. Some were even bold enough to use it as a way to attract straight guys.”

“How did that work out?”

“Sometimes not too well as you can imagine but you know the temptation was strong. The house had a few strong rules and one of them was that no one was allowed to bring a ‘street date’ to the house. If you broke that rule you were expelled.”


“Yes, but they needed to be. Anyway that worked out for me because near the end of the summer one of the residents picked up a guy and brought him to the house. There was a bit of an issue and the resident was asked to leave. At that time I was really getting in to my femme identity. Everyone around the house was calling me Claudia so I asked if I could move in. I was accepted. That ended my football and resident Phi Delt days. I kept up my active membership for appearances and except for taking off my body hair not much else changed about my outward appearance my next three years at U of T.”

“I bet your social life changed a bit.”

“No kidding. Gamma Alpha Upsilon wasn’t quite the party house you might think. The residents were pretty serious students. They tended to be in Library Studies, Social Work and the College of Art. They weren’t great party animals and they were happy to have a safe house. Excuse my French but they weren’t anxious to fuck it up. We kept the parties for residents and only a few guests at a time. We never had an open door policy like some of the fraternities and therefore we were never raided.”

“How did they come up with that Gamma Alpha bit? That’s pretty cute.”

“Well, one of the first residents has to take responsibility for that,” said Claudia. “At first it was just known as ‘the house’ but one spring afternoon one of our sweet boys came home swooning over the ‘hunks’ sitting out on the steps at the Phi Kap house. Everyone agreed but it struck one of them that they should form their own fraternity.

Claudia described how there followed a period of merriment as the boys reveled in how they would compete in the Inter-fraternity games losing the tug of war so they could frolic in the mud bath and how their secret handshake could be a mutual crotch grab and so on.

“I bet they could have given new meaning to the term greek society.”

We laughed and I squirmed a bit as I thought of that special form of love-making I’d come to enjoy so much.

Claudia continued, “however when it was announced what the name should be ‘Gamma Alpha Upsilon or GAY for short’ they were all in favor and from that day forward they privately called it the GAY House. Around campus they referred to themselves as the Gamma Alphs.

“What about you,” I asked, “I didn’t know you were gay.”

“Well I was sort of an anomaly. I wasn’t gay but I wasn’t altogether straight. I was the exception to the rule but I was accepted,” she said. “We could dress as we liked so I was always dressed as Claudia inside the GAY house. I did get involved in many a sex session. Sex was pretty liberal in those days. I learned to love the taste of a man and the feeling of a man inside me. I really enjoyed the sensation of a man’s climax that I had caused. Most of the gay boys didn’t dress that much but when they did they really flamed it up right. One of the boys earned a bit of money doing drag shows as Anita Mann. He became friends with Craig Russell when Craig was just starting out. When Craig’s mother first discovered his cache of drag she threw him out of the house and he stayed with us for a few days. Very sad but what a wild character he was!”

“One other thing: we had a pretty obvious rule that whatever happened at the GAY house stayed at the GAY House. When we saw each other around campus we weren’t giving each other the secret handshake or anything like that.”

“That made a lot of sense given that the times weren’t as liberal as they are today.”

“Also it was funny but it was as if the boys had two personalities. Outside the house and around campus most would act and talk very straight but as soon as they were inside the door they would be prancing and talking with the gay lisp.”

“And you?” I asked.

“I would go through the biggest metamorphosis of all. I went to classes as Claude. I had part time jobs as Claude but I had fun as Claudia,” she winked. “It wasn’t long before I was going with Marie to the St. Charles and Christine’s. Naturally I also did a few drag shows. I even went on tour in western Ontario with a show Craig put together. My specialty was ’50s-’60s numbers like Norman and My Boyfriend’s Back.”

“I remember that one.”

“We had fun with it. We would pick out the wimpiest guy in the audience and cue him to help. Then I would lip sync in the face of the biggest guy around “My boyfriend’s back and you’re gonna be in trouble….”  At the end the little guy would come out and flex his muscles and we would walk off the stage together. Usually I would tower over him. The audience loved it.”

“How did it all end?”

“I graduated in ‘75. The GAY house kept going but fell on tough times in the ’80s when their benefactor died. I heard he was an early victim of AIDS.”

“As for me,” Claudia went on, “I had pretty well decided to go in to teaching. I knew that to do so I would have to make a break with the GAY house and my crossdressing. I took my teacher training in London (Ontario) and got a job in that area.”

“It obviously worked out?”

“Well hell yes!” she exclaimed, “I was a pretty good teacher. I loved coaching and I married the girl’s Phys Ed head.  We had three lovely children who are now all grown and starting to make me a grandparent. For many years I had made a complete break from my GAY days.”

“So how did Claudia come back?”
“In two words, the Internet.”

I nodded knowingly. Claudia continued, “in the mid ’90s my wife and I got a PC for the home and soon followed computers for all the children as we were all quickly doing our own thing on the Internet. Of course I was doing my educational work, writing papers and building my consulting career but I also found time via Lycos and Alta Vista to catch up on the world of crossdressing. It wasn’t long before I was regularly hitting sites like TGForum, Karen’s Closet and anything else I could find. As the urges returned I got myself to Toronto and to Wildside where I had a makeover ‘I called it my refresher course’ and then there was no holding me back.

“I was becoming popular across North America as a conference speaker. That gave me the opportunity to get time away to be Claudia.”

“What does your wife think of all this now?” I asked as I gestured to the outfit the lovely Claudia was wearing.

“Does she know?”

“She wasn’t wild about it but as I was rekindling my love of being Claudia, Patricia had her own thing going. She had gotten back in touch with one of her former basketball players and the two had started a romance. I learned about it when a friend of mine said he’d seen the two women holding hands as they went up an escalator in a Hamilton area mall.  I asked Pat about it and she asked me about some of the things she had found on our computer. We talked it out and agreed our time together had come to an end. It was all very friendly. Everyone, including the kids, adjusted well.”

“That brings us to the present,” said Claudia. “I see we have both been using the Internet to broaden our range of acquaintances. Are you having any luck here in Toronto?”

We compared notes on our Toronto dates. We found a couple of names were common to both of us. We laughed as we compared the lines they give us.

As we finished our dinner and I insisted on signing the cheque to my room I contemplated asking Claudia to join me. She beat me to it.

“You know I will be very insulted if you do not invite me up for a nightcap.”

We took the elevator to the 23rd floor. Our elevator companions paid no attention. As soon as we entered the room the ‘do not disturb’ sign went on the door. It was all “to good to be true!”

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Category: Transgender Fun & Entertainment

Linda Jensen

About the Author ()

Canadian writer Linda Jensen is a long time contributor to TGForum. Before the days of the Internet Linda started her writing with the Transvestian newspaper. Her writing ranges from factual accounts of her adventures to fiction although frankly sometimes her real life adventures are stranger than the fiction. Linda is married to a loving partner who upon learning about Linda said, "she was part of you before I met you. Although I didn't know it she was part of the package I fell in love with. I don't want to mess up that package." "Does it get any better than that?" asks Linda.

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  1. says:

    I would have loved to have been in some of our places…..but you look so good that few could ever do it as well as you..thank you for the short epic….Candy

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