Times Do Change, Part 2 The 1960s

The Lives of Crossdressers Through the Decades

Did I mention that the other Linda had become a pretty good soccer player? She was good enough to play on her school’s teams, both in high school and university. In those days soccer was not a varsity sport at her university but they usually had a strong club team with a number of preppies but most of the strength coming from British and African post-grad students. One of the school’s English professors enrolled and took undergrad courses each year so he could play for the university club’s top team.

‘What has that got to do with Linda’s crossdressing?’ You might ask. Well, I asked her, too.

“We played in a lot of tournaments against other college clubs,” replied Linda. “One time we were playing in Providence Rhode Island. As usual we had a Saturday evening banquet with a bit of drinking. We were not going anywhere in the tournament as we were already relegated to the consolation round. Our professor-teammate suggested a night on the town and most of us joined him.

“He led us to a bar with a drag show. I recall it was a good show with lots of ribald humor, suitable for the mixed crowd it was. Our college boy soccer team even got centered out a bit with offers that the girls could come back to our hotel. The guys all declined.

“But that was not what interested me,” claimed Linda. “In the audience were some ladies together. They were not drag queens and they were not gg’s. They must have had balls of steel, pardon the expression, to be out in public in that era not even under the cover of Hallowe’en.

“Of course, I was enthralled seeing other guys taking their crossdressing out of the closet and into a nightclub,” she continued, “Right then and there was step one for me deciding that I was also going to try for the full makeover and full breakout.”

“No kidding? I had a similar experience back in the ‘60s,” I exclaimed. “I was spending a summer in Toronto. Walking up Yonge Street I heard some nice dance music coming from a club upstairs. Dance music meant women and I was all for finding women. I was soon in the club and soon talking with one of the prettier ladies there. I loved her beige wool mini-skirt and jacket. I still remember it. She was slim and cute even though her breasts seemed a little small. At one point after looking around I told her that some of the girls looked like guys. ‘Honey, we’re all guys,’ she replied.”

“What did you do?” Linda asked me.

“I was gobsmacked but I did the only thing I could do. I went home with her and we made love!” I proclaimed a bit triumphantly. “But here’s a sign of those times,” I continued. “A few weeks later I went back to the club and it was deserted except for one T-gal on the door. I asked her where everybody was. She told me that the evening before a couple of Toronto’s finest, simply on beat patrol, had come up to the club to look around. The cops meant no trouble but such were the times that the girls present got scared and headed down the back fire escape and they had not come back the next night. Remember they didn’t have to be doing drugs or selling services to be charged with a crime. In staid old Toronto they just had to be dressed as they were to be guilty of something.”

“Yes, I remember those days,” replied Linda. She was keen to continue her story.

“So, the drag club was your Step One,” I prompted her, “what was Step Two?” I asked.

“Step Two and Three more or less happened together. My older sister decided to move out and she left a lot of her old clothes behind. She was much shorter than I was, but I knew from experience that we wore the same size bra and panties. I was soon to discover that I could fit her skirts and her sweaters but not her dresses.”

“Two out of three is not bad,” I interjected.

Here is the strange thing,” continued Linda, “Wearing bras, panties and slips—those were items I associated with sex. Seeing myself wearing them, I was in a constant state of arousal, that is until I ejaculated. But wearing a skirt and sweater that was ordinary day stuff that I didn’t necessarily link with sex. I discovered I could live a day as a normal woman if I were wearing normal clothes.”

“Been there; done that,” I said. “What was step number three?”

“Magazines,” Linda replied. “Of course, I came across soft core ones like Female Mimics International and Drag Queens. They were okay but not nearly the turn-on that I discovered in 1968.” She paused. I could see her take a drink. She could see me squirm in anticipation.”

“Okay, you win. What did you discover in 1968?” I pleaded.

“Do you remember a magazine called Penthouse Digest?” she asked. Of course, I remembered.

“They used to run articles about different sex themes, perhaps cover ten or so different subjects in one magazine. That way they could sell magazines to ten or so different fetish groups. One of their frequent themes was the male interested in wearing female clothing. Remember the word ‘crossdresser’ was just coming into existence.

“I read one article where the guy’s girlfriend got him to try on her clothing and of course he loved it and they had great sex. Another was about a guy being caught dressed when his wife came home early. Again, great sex. The best thing about the Penthouse Digest stories: there was always a happy ending with great sex.”

“Yes, I remember Penthouse Digest,” I inserted, “we were probably reading the same issues.”

“Not only did I read them I wrote one for them, submitted it but they never published or even acknowledged it,” said Linda.

“So, what got Linda out of the closet and into the clubs?” I asked.

“Not so fast. That would be a while yet,” she cautioned. “Remember, I was a young teacher with a wife and child and another on the way. A lot of the time I was working days and doing marking and lesson prep in the evening. My wife got a job in the evenings selling wigs at the local KMart while I also did the baby sitting. When our girl went to sleep, I had a precious hour to get out my meagre stash of clothes and dress to my heart’s content.”

“Don’t tell me. She came home early and discovered you wearing one of her dresses.”

“Not exactly. I came home from school one day. She was in a fit. She had found the stash of clothes I had hidden in the attic and she made the decision that I had a secret girlfriend.”

“This is sounding like a Penthouse story.”

“A bit. She was really hounding me. I wanted to tell her the stuff must have been left by a previous tenant, but she had found a sales slip dated only a few weeks earlier. What was the least bad option? I decided to lay it out that the clothes were mine. She doubted it at first but that evening she made me try on the clothes. Of course, they fit. But you know how it is when you are alone. Being dressed you see the most beautiful image looking back from the mirror. With her present, I just felt hideous standing there with no wig, no heels and no makeup.

“That was the end of it for a few days but that Friday my wife asked her parents to take our daughter so we could have some quiet time together. They agreed. They loved the girl.

“Then came the big surprise. After dinner my wife told me to take a shower and have a shave. I agreed thinking all must be forgiven and we were going to be back to great sex.”

“The fact that you are telling me tells me there was more to it.”

Linda continued. “When I got out of the shower, I found the contents of my clothing stash spread out on our bed. There was a pair of heels beside them and one of her KMart wigs as well. She told me to start getting dressed. Nervously, I started. When I had the panties and bra on, she told me to stop and sit at her vanity.”

“Was she part dominatrix?” I interjected.

“I was thinking the same thing and I was starting to enjoy it,” replied Linda. “Anyway, she applied foundation, eye color, mascara and lipstick. She was good with makeup. She told me to finish dressing. She even helped me with the zipper on the one dress I owned. Then came the heavenly moment, the crowning glory, so to speak. She fitted the wig onto my head.”

“How did you feel, being dressed in front of someone who a few days earlier knew nothing of your hobby?” I asked.

Linda replied that without doubt she was nervous through the whole experience. She expected a shoe to drop like maybe the whole gang of their friends to jump out of the second bedroom with cameras rolling and yell ‘Surprise!’. But no, the evening ended with some great love-making with Linda enjoying giving woman to woman oral’ I hope she doesn’t mind me sharing with you how she was titillated by her wife’s gentle fingering you know where.

It sure sounded like a souped-up Penthouse Digest story to me, but Linda swore it was true.

Did they live happily ever after? Not for long. Apparently Linda’s wife got involved in a workplace romance. She and the (now two) kids moved out and Linda became a weekend dad. She also had her pick of lady-friends at the local Parents Without Partners group.  She ended the decade back in the closet and craving the memories of the evenings when she got fully dressed.

She would get halfway through the 1970s before some twists of life allowed her to develop her femme lifestyle. I’ll tell you more next month.

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Tags: crossdressing, featured, History

Category: crossdressing, History