Is it possible to retire from crossdressing?

My friend Linda and I were meeting via Skype to discuss our series of articles about the history of crossdressing in America over the last 50+ years. We had been part of the scene for many of those years and thought we had developed a considerable insight into the changing scene.

We were just coming aboard when the term crossdresser was coming into common usage to describe those people, mostly males, who fit between the ‘fetishistic transvestites’ and transexuals along the widening transgender spectrum.

We had good memories of the changing public attitudes as we each went shopping en femme and noticed a drop in the incidents of stolen glances and sometimes hostility among other shoppers to now a seeming indifference from the others. It seems to me that now, the only one who ‘reads’ and cares are probably other crossdressers who happen to be in drab that day.

We both considered the 1990s as the Golden Era for crossdressing. There were so many drag and t-friendly clubs. There were support groups thriving everywhere, special weekend conventions several times a year and the new Internet was bringing more information and more communication to everyone who wanted it.

We lamented a slight decline in the club and convention scene though the early 2000s but we enjoyed our expanded love lives brought to us courtesy of websites such as Craig’s List and Transgenderdate.com.

We had lived it all as the years flew by. We had hardly noticed the passage of time. Perhaps it was our wigs that kept us feeling young. Well, the wigs and pretty full social lives.

Then Covid hit. Travel was restricted, clubs were shut down, all for the good purpose of trying to keep us safe. I was and am a supporter of these safety precautions and so, I think, is the other Linda. But we sure have been missing our social lives. I get out occasionally and look forward to getting out more. Even when I do go out, I find myself keeping my distance, not so quick to get intimate and I’ll wear a mask when I’m with a group of strangers. To me the mask is like making sure a man is wearing a condom if we are having penetrating sex. I know I don’t have an STD. He may say he doesn’t but maybe he doesn’t even know he’s infectious. Same with Covid. If there are, say, 50 people at a party and one of them is Covid positive but asymptomatic. Do I want to take the chance that the person I’m with is the infectious one? No, not me.

But I digress. My friend Linda and I had set up for a Skype call one evening. For me that meant telling my partner that I would need the computer room and that I would be transforming while she prepared dinner. (We share cooking duties in our household). I enjoyed the Skype calls as it was one of my few remaining times to get fully dressed and made up. Even though Linda would only see me most of the time from the neck up we both always took time to stand up, step back and show our outfit of the evening. For me that evening it was a navy-blue knee-length pencil skirt, a light orange blouse and a silver grey wig.

Linda: she wore. . .WHAT!? I thought at first I might have accidentally logged in with some stranger. The screen showed an older mostly bald guy wearing a man’s golf shirt and apparently a pair of jean shorts. The screen name said it was Linda but he did not look like her. “Yes, it’s me,” the guy said, “at least it’s the new me.”

It dawned on me that I had seen this guy once before. Linda and I had met up in Buffalo, NY some years ago. We had decided to take turns escorting each other out on the town. On the Friday night, with she en femme and me in drab I had taken her to a Sabers hockey game, a late dinner and then ended the evening at a gay/drag club in downtown Buffalo.

The next evening, I was dolled up as the male Linda took me to dinner, a symphony concert and yes, back to the drag club.

Why did we do that? Good question. Back in the day there were still times and places where even the most passable of crossdressers might feel uncomfortable in a public venue. We wanted to see if having a male companion would lessen the attention otherwise brought to one or two t-gals out on the town. Our conclusion was that having a male companion was like having a free pass to anonymity.

But you know what? I told that story to a gal friend of mine. She said it was not just t-girls that a male companion protects. She told me that when she is out with another lady or a group, she is often aware of the stares and sometimes leers from the men around. If she were to be out alone then it was as if she were fair game for every lecher in town. But a man gave protection. It was as if there was a male code, she suggested, men don’t walk on each other’s turf.

So why was Linda in drab that evening while we met on Skype? She knew I looked forward to seeing and complimenting her feminine image.

“I’m seriously thinking of retiring,” she told me.

“What are you talking about. You retired years ago,” I replied but I knew what she was talking about.

“No, I think I’m going to pack up my skirts and dresses, throw in my heels, my jewelry, high heeled boots that I haven’t worn in 30 years, coats and wigs and get rid of it all.”

“What? No, you can’t do that.” I protested, “No one ever retires from crossdressing.”

“How do you know that,” Linda retorted, “You know we used to see friends year after year at different clubs and conventions or we would meet them online. Then we wouldn’t encounter them anymore. Sometimes we would hear that they had passed away. If we didn’t hear anything we would also assume they were now dead, right?”

“Yes, I guess so.”

“Well, what if they were not dead but had just ‘retired’ from crossdressing? Isn’t that possible?” pronounced Linda, I think in defense of what she was about to say.

“Yes, I guess it’s possible and certainly preferable to the alternative. But why? Why would you want to retire, as you call it?” I continued, “You know that if you were transexual there would be no question of you retiring. You are in it for life. You are as close as anyone I know to being TS. Why would you want to bail out?” I asked almost desperately. I felt as if I was going to be losing my best friend. “You’re not ill are you and you don’t want to tell me?” I asked as a horrible thought came into my mind.

“No, no. I’m fine,” Linda reassured me as she launched into an analogy. “You know in professional sports how some players have long and great careers and then suddenly retire. They say they want to ‘go out on top’”.

“Yes,” I replied suggesting a bit of hope, “like Tom Brady.” Brady is the star quarterback who announced his retirement and then apparently changed his mind and came out of retirement barely a month later.

“No, I’m no Tom Brady and I’m not at the top of my game,” Linda replied with a bit of lament in her voice. “I am more like the journeyman pro who hangs around the league perhaps a bit too long then realizes that younger players are just a bit bigger, faster and stronger. For the pro, when the club management suggests they might have to make a move to ‘free up cap room’ he knows it is time to move on. In my case it is when I looked in the mirror and did not get excited by what I saw and I went to a ‘tranny night’ and no one there seemed excited by what they saw. When, after a little weight gain during lockdown I realized most of my outfits did not quite fit and my tummy bulge was out of control that all said to me that a lifestyle change was in order.

“Then the straw that broke the camel’s back came when I realized this afternoon that I was expected to get dolled up to meet with you on Skype and I asked myself, ‘Aww, do I have to?’ That is when I realized it was time to pack it in.”

“You mean you just made the decision just today? I hope you will sleep on it,” I said hopefully.

“Of course, I’ll think on it. Tomorrow is Sunday so I can’t go rushing off to dump a load of boxes on the Salvation Army, can I?”

“Take your time,” I urged but in my heart I was starting to realize that a lot of what Linda was saying just made sense. Crossdressing is not a job. It is not an activity where anyone’s life depends on her participation. If it is no longer fun for her then she should just not do it.

“I’m pretty well decided,” she declared. “I’m going to keep an outfit or two for emergencies but everything else is going. You know I figured it has been close to 50 years since my last purge. It is high time for another.”

“My God, I’m going to miss you but if you go through with it can you send me that honey blonde Henry Margu wig that you have for special occasions?”

“Well, that did not take long for the vultures to start circling.” Linda shot back. “Of course, it will be yours.” For a second, she was out of screen before coming back with a wig that had been lovingly set on its stand. “See I have it here ready for you.”

Oh damn! She was serious. “I’m going to miss you, my friend,” I nearly cried.

“Oh you haven’t seen the last of me,” she replied. “Old crossdressers never die. They just become admirers.”

And that is how I learned of Linda’s ‘retirement’ from crossdressing. I regretted that I was losing one of my BTFs (Best Trans Friends) but it was great to know I would have another dependable admirer-friend to call on when I would come her way or she mine.

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Category: crossdressing