60 Years of Changing Times, Decade by Decade, Part 1

“The line it is drawn
The curse it is cast
The slow one now
Will later be fast
As the present now
Will later be past
The order is rapidly fadin’
And the first one now
Will later be last
For the times they are a-changin’”

Last verse of The Times They Are A-changin’ by Bob Dylan

In 1964 Bob Dylan wrote and sang that ‘the times they are a-changin’ It is pretty safe to say that the times have been a-changing for the near 60 years since and probably for the thousands of years before.

The changing times are as true in the wonderful world of crossdressing as they are in other parts of society.

I have a crossdresser friend, also with the chosen name Linda, who is now in her 70s. She claims to have been a crossdresser since before there was a word for it.

“Well, weren’t you then just a common everyday transvestite?” I jokingly asked her.

Mistake. “A transvestite!” she shot back, “those are the guys who just put on some lingerie for the sexual thrill. I have always been much more than that.”

I had to change the subject. “So, what did you do in the war, mommy?”

“World War II? I don’t go back that far but almost.”

With only a slight encouragement from me the other Linda launched into a decade by decade telling of her life as Linda and how through the decades her crossdressing times had seemed to be continually changing.

One of her very oldest memories in life, she says it was probably 1950 but it could have been 1949 based on where the family was living — was of her mother catching the son wearing mom’s bathing suit. It must have been a strange image, a four-year-old boy probably holding the shoulder straps to keep his mother’s bathing suit from falling. Linda says she doesn’t remember anything about the incident and only remembers it because she was there when her mom told her best friend how cute this son had looked wearing her bathing suit.

‘How cute’: really? I bet there are thousands of crossdressers who wish that had been our parents’ reaction when they first caught us!

Did that set the pattern for the rest of Linda’s life? There was no parent threatening to beat the living daylights out of him if they ever again caught him wearing girls’ or women’s clothes. No, instead the boy heard that he was cute. What child does not want to be considered cute. Certainly, the boy Linda was cherished that response. The bathing suit was only the first of many forays into crossdressing for the young Linda. “I was way too young to have an erection or ejaculation, so these were far from sexual experiences,” proclaimed Linda.

She had a point there, didn’t she?

“I went through the 1950s doing very little of any kind of crossdressing. I was just too busy leading a boy’s life. Sports, paper route, other odd jobs and eventually crushes on many of the girls in my classes. I found myself arranging to sit behind girls in my classes. In our school the girls had to wear skirts and white blouses as a uniform. By sixth grade most of the girls had switched from tee-shirts to bras underneath their blouses. When I was supposed to be learning math or history or something else, I was endlessly studying the bra straps under the blouse of the girl in front. I wondered how the straps must have felt. Actually, I knew how they felt. By then I had picked up my own bra and panties out of some discarded clothing meant to be delivered to some charity shop. I just longed to know how it would feel to wear the bra all day long.”

“I hear you,” I chimed in as Linda paused for a breath or a drink, or both.

“Then the big day came,” continued Linda, “I know it was 1959 and I was 13, going on 14”

“Not 13 going on 30?” I asked remembering an old way of describing teens advanced in their years.

“Not me,” she countered, “I was more like 13 going on eleven. Puberty had not struck. I was somewhat tall but quite thin and still waiting for the first time I could run a shaver across my face. I had fallen way behind my friends athletically and the girls certainly did not see me as dating material. Nor I them. For me the expression “getting into her pants” really meant a desire to put on a pair of a girl’s panties”.

Yes, yes, been there done that, I thought. “So, tell me about the big day, ALRADY,” I said in my not very convincing New York accent.

“In retrospect I think there must have been a bet or a dare going around the class. For Hallowe’en there was going to be a costume day at school. Some of the cool girls who normally would not speak to me approached me out of the blue, asked me to sit with them at lunch. We talked about the upcoming Hallowe’en Day and they asked what I was going to wear.”

“I think I know where this is heading,” I interjected. Now we have seen or read the plot many times but back in the 1950s who knew?

“Yes, hindsight is everything but back then I was in heaven just sitting with these girls who all wore beautiful bras and had boobs starting to fill out the cups. When I told them I had no idea for a Hallowe’en costume the girls asked if I wanted to help them. They wanted to be a popular female singing group but they were short one member, they told me. They thought I would look a lot like one of the group’s singers. Would I play along, they asked.

“Probably quicker than I should have,” Linda says she agreed. It was set they would meet at one of the girl’s places a few days before Hallowe’en when they could try on the costumes, matching pencil skirts, blouses and high school letterman sweaters that the girls had scored from somewhere and have a rehearsal.

“Do I have to wear a bra?” Linda says she tried to protest.

“Yes, you do, and a girdle, too. We don’t want anything popping out,” one girl said as the others laughed.

As it was time to head back to class, the girls parted with one saying she would call with further details. Linda was elated, apparently too elated to notice some smirking at the JV football table near the door. If she thought anything it was that those guys were just jealous.

Linda says it seemed like an eternity until the appointed day came. The dress rehearsal. And she did mean dress. The girls had switched the costume idea from skirt and blouse to dress and crinoline. Apparently, they had decided that Linda did not have the hips to do the skirt justice.

“How old were these girls?” I asked.

“Fourteen going on thirty,” the other Linda said with a smile. “It didn’t take me long to figure out these girls were playing for keeps. They were used to winning and they wanted to win the Hallowe’en costume contest.

“Do you remember a ’50s group called The Chordettes?” the other Linda asked me.

The actual Chordettes.

“Sure I do but not from the ’50s,” I said with a smile. “Their big hit was Mr. Sandman. That was an oldies standard at dances I used to go to.”

“That and Lollipop,” corrected Linda. “Lollipop was a big hit in ‘59 so the girls decided we were going to sing it during the talent contest part of the day. “

“You were a singer?”

“No, we pretty soon discovered that none of us were singers so we decided to have someone play the record and we would lip sync, or we called it miming. But let me tell you the girls went all-in on the makeup — thick eyeliner and false eyelashes, foundation and rouge and dark red lipstick. By the time they had finished with me I was sure glad I had that girdle on. I got my first erection and to this day I don’t know whether it was the attention of the girls or the feel of the clothes that triggered it.”

“I vote for Door #2.” Then I asked, “What about your hair? Did you have wig?”

“We all had wigs,” Linda exclaimed. “A couple of the girls were blondes and they wanted to look and sound authentic. The Chordettes were all brunettes. “I tell you we looked pretty good. At the dress rehearsal the girls swore me to secrecy. Not to worry I was not going to tell anyone how much I enjoyed being a pseudo Chordette.”

“Now really,” I asked, “back in those days every girl going out or performing like The Chordettes would have been wearing heels. How did you pull that off?”

“I’m surprised the girls didn’t get suspicious about that. Of course, I had been wearing my mother’s heels around the house. I was an old hand at wearing heels. But after one of the girls asked why I was so good on heels I started to fake some stumbles now and then. I promised to practice a lot before the big day.

“So, it came Hallowe’en day. I left home as usual but went to one of my new friend’s places to get into my costume and be at the school for the afternoon assembly and costume show. By then the girls had some ideas for jazzing up their performance. You know the number Lollipop is supposed to be the age of innocence personified. Well, the girls threw in some gestures that suggested perhaps their cherished lollipop was hiding under the skirt of my dress. The audience was in the dark. With all of us in wigs they thought we were just four girls from the school that they were trying hard to recognize. We were pulling it off. They had arranged to cut off Lollipop and finish with Mr. Sandman the other big Chordettes hit. We transitioned from one tune to the next flawlessly and had a lot of the students singing along. But we had something special: the great costume reveal.”

“Not what I’m thinking?” I exclaimed.

“You would probably expect it. You have been to enough drag shows but the audience and I were taken totally by surprise. Do you know near the end of the song and the girls are singing to Mr. Sandman and a deep male voice cuts in to drawl “Yes”? Well, they wanted me to deliver that line in person with as deep a voice as I could muster. What I didn’t know would happen was that as I delivered the line one of the other girls would come up behind me and pull off my wig.”

“Holy crap, you must have died!” I exclaimed.

“At first I wanted to crawl right under the stage. The audience was shocked. But the girls were great. They must have rehearsed it too. They came up and hugged me. They pulled off their wigs and soon the audience was on their feet cheering. I think as soon as the school saw the cool girls were okay with this bit of drag show then it must be alright.

“Did you win?” I asked.

“Hands down!” Linda exuded her pride still at an event more than 60 years in the past.

“I’ll bet it was difficult to put that Linda genie back in the bottle.”

“You know it was impossible,” Linda agreed, “Of course I played the straight guy around the school and having some of the cool girls as my friends certainly elevated my status among my peers. At home I would get out my special wardrobe from time to time and even practice on makeup the girls had taught me how to wear. And I learned one other important lesson.”

“What was that?” I asked.

“In those days crossdressers, transvestites, drag queens, whatever you wanted to call us, were held in low regard and in many places it was actually illegal for a man to appear in public dressed as a woman. Except on Hallowe’en. Apparently that law was suspended for Hallowe’en. I was to take great advantage of that in the years to come.

“But back to the school days: I was 13 then and puberty was about to strike me with a vengeance. I’ll have to tell you about it sometime.”

I told her I would be holding her to that promise and when she does tell me you readers will be the first to know all about it.

“One final question,” I asked Linda. “Looking back on it do you think those girls had some intuitive inkling of the trans tendency building inside you?”

“We’ll never know, will we,” she replied.

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Tags: crossdressing, featured

Category: History, Transgender Fun & Entertainment