Retro Rerun: I Remember the St. Charles

Someone, sometime is going to write the definitive history of drag clubs in North America. That someone won’t be me. I don’t know that much about them but I do remember a short period of time at the St. Charles Hotel on Yonge Street in Toronto.

The St. Charles wasn’t really a hotel; it was just a big bar. Actually it contained two bars and an upstairs dance club. In the late 1960s the St. Charles was the only openly homosexual club in Toronto. (The appellation ‘gay’ was yet to take the politically correct place of terms like fag and queer) On many nights the two downstairs rooms, with their large matching horseshoe shaped bars, would be crowded with men. On Halloween, television crews and curious onlookers would crowd the street outside the St. Charles to watch and hoot at the arrival of fancily costumed queens as they arrived for their big party. The girls must have been very brave indeed to face the derision and catcalls that were considered fair comment in those less enlightened days.

My personal experience at the St. Charles was limited to the early summer of 1968, so I don’t know how long it was open or how popular it was. But even in that short time it had a lasting impact on my life. I was in Toronto, having just finished a year of graduate studies at the university. My wife and baby had been with me for much of the year. However, to cut expenses they had gone back to spend the summer with her parents while I took a smaller apartment, enrolled in a summer course and worked at a restaurant on Yonge Street earning more money in two evenings than I could in a week of working at my previous job in a bank.

I didn’t have much free time but one evening my shift at the restaurant ended early so I decided to walk up Yonge Street to see what action I could find. I looked in on the men at the St. Charles bars but I wasn’t going in there, “No way!” Instead I was drawn to the sound of dance music coming from upstairs. I walked up the stairs and found a very pretty lady taking and selling tickets at the door. Yes, there was dancing and yes, it would go to 1:00 a.m. and yes I could go in, she answered to my questions. Paying my two dollars, I entered the room and saw a crowd of about twenty women and ten men – great odds for the young lounge lizard I was. Soon I was dancing with and sitting with a very cute blonde girl named Linda. She was a hairdresser and a lovely dancer. I still remember she was wearing a beige mini-skirt and matching jacket. I also danced with other girls in her group and was having a great time.

Now here I should perhaps pause and explain that at that time I didn’t know much about crossdressing. I don’t think the word had been invented. I did know that I got excited by putting on lingerie and I knew about transsexuals like Christine Jorgensen and Britain’s Roberta Cowell, and about drag shows, but it never occurred to me that men, gay or not would dress like women to go out for a normal night out like the one I was on and I didn’t think I could ever be fooled by a man passing as a woman.

So it came as a big surprise to me that, after looking around more carefully at the rest of the crowd, I said to Linda, “You know some of these girls look like guys.” Her reply, “Honey, we’re all guys.” I was surprised and fascinated; some of the girls were big and a little awkward and I could believe they were men but not Linda; she was so pretty, so feminine. If I had not had and purged several collections of feminine underwear, if I was not currently privately wearing bras panties and nighties my wife had left behind I probably would have walked out of the club. Instead I stayed with Linda and when she invited me to go with her to a friend’s apartment I agreed.

We were four in the cab, three ‘girls’ and me. When we arrived at the apartment two of the girls sat in the living room, turned on the television and lit up a joint. Linda and I retired to someone’s bedroom where we talked and started kissing and caressing each other. I don’t remember much of what we talked except Linda said she was saving money to go to Japan for a sex change operation. Maybe that news made me feel that I was actually going to make love to a woman, not a man. Linda had every bit the appearance of a young, slim woman — lovely blonde hair, smooth skin and nice legs. And, like my wife, she wouldn’t perform oral sex on me. She was my first anal sex experience and she taught me to be gentle and patient. Linda did let me hold her penis as I moved inside her so I know that after a short time of intercourse we both climaxed at about the same time.

I would like to say that Linda and I spent the night together and became good friends and lovers but after our climax I had a serious attack of post coital let-down. I left and never saw her again. However, a few years later I read in a newspaper that a Toronto girl named Linda had become the first person to receive a sex change operation in Canada. I hoped it was my Linda. After our brief meeting Linda became an inspiration for me. It started to occur to me that I could take my transvestite fetish from the bra and panties stage to perhaps dressing completely and going out in public myself. Then years later when I needed a name to go with my new femme identity I ‘borrowed’ Linda’s.

Several weeks later I made my second and last visit to the St. Charles. It was much quieter than the first night and instead of a lady there was a man on the door. He told me that the night before two police officers had visited the club and the girls had scrambled out the back door in a panic. The girls were pretty spooked so in those pre-Stonewall days they weren’t likely to come back that night. So I got a drink and returned to talk to the guy on the door. I asked him about the girl who had been there on my previous visit.

“Did she look like this?” he asked, pulling a photo out of his wallet and showing it to me.

“Yes,” I said.

“That’s me,” he assured me as he looked at my disbelieving face.

We talked a while longer and because it was such a quiet night he closed up early and invited me home with him. I went and this time my partner did give me oral sex; I remained a passive partner. I left soon after but for the rest of the summer I would go back to his apartment about once a week, sometimes finding a man, sometimes a woman but always finding someone willing to take me to bed.

At the end of summer I left Toronto and resumed my wedded life and although my wife and I would soon divorce I did not have another sexual relationship with a man until over twenty years later and those have been only as my own ‘Linda.’

About ten years after that summer I returned to Toronto and to the St. Charles. It was a changed world. Formerly effeminate ‘fags’ had grown mustaches, put on leather and T-shirts and become ‘gays’. The St. Charles was facing competition from a growing number of other clubs and the queens had disappeared from the scene. One man who said he’d been around the St. Charles a long time even refused to acknowledge there ever had been a drag bar there. I was left thinking I’d imagined the whole thing.

Now the St. Charles is gone, the gay scene has become a village and queens, crossdressers and transvestites have reemerged in a number of bars, clubs and support groups. Last summer I visited a transgender support group in Toronto and met up with a ‘veteran’ TS who had also been at the St. Charles in the heyday of the late ’60s. She confirmed my impression of the fun times. But she was no help in telling me what might have become of my two lovers from ’68, gone perhaps; but not forgotten.

Tags: crossdressing, featured, History

Category: Transgender Fun & Entertainment, Transgender History