It’s A New World for Crossdressers

| Jan 2, 2023
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For some time, I have been lamenting about how Covid has kicked the normalcy out of the lives of the average sex-craving crossdressers.

I don’t mean the ones who sneak on their wives’ bras and panties then play with themselves in front of a mirror. Business as usual for them—unless their wives are working from and staying home more often.

I mean the ones who could easily be called non-op transgender as they (we) are feminine in every way except for the lack of surgery and—oh yes—we spend a significant part of our lives in male mode. Across the country, T-friendly night clubs have closed or changed format in great numbers. I visit Florida a lot and within a year of each other the fabulous Flamingo Resort in St. Petersburg and the iconic Parliament House in Orlando were sold off, closed and demolished. Was it just coincidence that Covid restrictions came along and told their customers to stay home? Perhaps, but I know I never went near those places once the Covid viruses started raging through the state.

It seems more and more difficult to find a nice bar in which to hang out and wait for a good looking—but perhaps shy—admirer to pass by. It seems I am not the only one finding the ‘trolling’ a bit uncertain.
This did not happen to me, but I wish it had. I hope you enjoy the experience and perhaps try to live it vicariously as I did. This is Katie’s story.

Katie is a 50-something crossdresser. She may be 70-something but all dolled up she can pass as being in her 50s. She is as cute as they come which in CD terms means she is tall, average build, somewhat muscular with larger than passable hands and eyes that radiate their blueness, particularly when she chooses a dark wig. Like all passable CDs, she knows she has a good chance of being read. She also knows from experience that by being respectful of the female image she has a very good chance of being accepted.
One thing though: Katie does not look like a Katie. I told her she looked more like a Katherine, a young Katherine Hepburn, maybe. She exudes class.

“Katherine was my original femme name,” she explained, “I chose it because that was the name of my first girlfriend and she had let me try on her bikini once when we were making out. I owe my interest to her. Katie is just what I put on my badge at one weekend event to make me seem more friendly. It worked so I kept the name.”

“So, the social lives of crossdressers are not as dead as I make it out to be?” I asked Katie.
“There is not doubt that many clubs have gone and others have changed their operations to appeal to different clientele but there is still life in our lives,” she replied with a sparkle. I could tell Katie had something to tell me.

Katie had been to Orlando. She had been there Tuesday to Saturday for a conference and trade show in the I-Drive area but decided to move closer to downtown, to the Crowne Plaza for the weekend.

“Hey, that’s where I used to stay,” I chirped in, “it was so close to the Parliament House and on weekends the rates were very good.”

“Well, the PH is gone and the rates are not so good any more but I like the place and it has a nice hotel lounge,” Katie replied, “you can meet some interesting people there.”

So, what happened that has you all revved up?” I asked, “Spare no details.”

“Well, I got invited to the trade show wrap up cocktail party and didn’t get to the hotel until later than I expected. I grabbed a quick dinner then got to the process of getting dolled up. I must admit to getting invested in the Army-Navy football game. It was a close. . .”

”Okay,” I said with a wink while putting my hand on her arm, “There are some details you can leave out.”
“My plan was to head over to a club called Southern Nights.”

“I know it,” I said, “I went there occasionally for a break from the Parliament House. Nice intimate drag show and a diverse crowd.”

“That must have been a Friday night and some years ago,” retorted Katie.

“I went there on a Saturday,” she continued. “the first thing I noticed was that all parking on site was valet only and the nearest block or so were all strictly ‘No Parking’. The next thing I noticed was even though it was early, there was a line up to get in. And, nearly everyone waiting to get in was a young female dressed in black spandex and most of them quite overweight. I was going to look way out of place wearing my Christmas red party dress.

“I know about the line up to get in,” I interjected, “Ever since the massacre at the Quest nobody gets into a gay club in Orlando, perhaps across Florida, without being carded and searched. Frankly I wouldn’t have it any other way.”

“Yes, I don’t have a problem with the I.D. issue and frankly if it wasn’t for the line up, I would not have noticed the personality of the crowd. So, I struck out at the Southern Nights. I suddenly didn’t feel like going in. I felt my night was going to be a bust.” Katie lamented.

“What did you do?” I asked. Katie’s night wasn’t going to be a bust. She had told me there was a story there.

“I did what every girl does when she is feeling blue. I went shopping,” Katie replied, “Luckily there was a Ross nearby.”

“Crossdress For Less, you mean?”

“Yes, I was a bit too dolled up for that crowd and the store security took note of me right away but that’s okay. I found some nice dresses and skirts to try on and even picked out two sundresses to buy,” Katie continued. But she said he hit a roadblock when going to make her purchases. There was something like a dozen people in line but only one cashier working. It seemed like those dozen were all trying to check out with all their Christmas shopping in the carts.

Katie decided to return her dresses to the rack and walk out. Security followed her for a bit, she said, until she turned to face him and showed him her open and empty hands. He apparently turned away.

“I then went back to the hotel. I was ready to call it a night,” said Katie.

“You can’t strike it rich every night,” I commiserated.

“What are you talking about? I still got lucky. I’m sure glad I don’t quit as easily as you do,” Katie chided.

“Why, what happened? Knowing you, you probably walked into the hotel, met some guy in the elevator and he said, ‘let’s go have a drink in the bar’ or something like that.”

“Close. I decided to check out the bar and there was a good crowd with some nice looking, tall men.”

“Just your type,” I said to Katie who herself stood over six feet when she was wearing heels.

Apparently. she had not been long at the bar, sipping on a glass of wine when yet another tall man came into the bar, looked around a bit and chose the bar seat next to Katie.

“Is this seat taken,” he asked.

“I was saving it for you,” Katie replied with a coy smile.

“What was this all about? What happened?” I asked excitedly.

“Have you ever heard of a basketball team, the Toronto Raptors?” asked Katie.

“Of course, I have. They’re Canada’s team! Was this guy a player for the Raptors?”

“No,” said Katie, “He wasn’t that tall. It seems the Raptors had two games in a row in Orlando, Friday and Sunday, so a bunch of guys from Toronto signed up for a trip to Orlando to watch the games and go to a theme park on the off day. My friend had spent the day at Universal but left the group early to get back to the hotel. He intended to do some work at the hotel but he was coming in at the same time I was. I guess he liked what he saw. He told me later that he went to his room, freshened up a bit and decided to take a shot at meeting me.”

“A shot at getting you into bed, you mean.”

“Well, I guess so but at first, he was subtle about it. He never let on whether he knew I was trans or not.

“We chatted for a long time as more people came into the bar. Even when some of his friends from the Raptors fan trip came in, he didn’t shy away from talking with me. In fact, he introduced me to some. ‘Guys, this is Katherine,’ was all he said, very nonchalantly as if that had been my name all my life. Soon we were a group talking about basketball and why the Raptors who had shown so much promise at one time were producing such mediocre results. Apparently, they had looked lackluster in losing to the Orlando team the night before.

“I asked the group if Canadians were all so tall. One of them replied that all weren’t but these guys were basketball fans because they had been basketball players and they were basketball players because in grade school or high school they had been recruited onto the team because they were taller than most. These guys liked the game and stayed with it playing rec league ball and going to the odd Raptors game. My new friend even helps coach a high school team in Toronto.

“Then one turned the table on me. ‘You’re not so short, yourself. Do you or did you ever play ball?’ he asked. I replied truthfully that volleyball had been my game. Luckily, none of them pushed for details and I didn’t have to explain that one year my team had been boys’ state champs.”

“Weren’t they reading you?” I asked.

“I thought maybe not,” Katie replied. She was having a great time. Her friend was treating her like a princess. The other guys would chat for a while, then move on. Others would move in. It turns out I think there were about 20 in the fan group and she met most of them. “And you know what,” Katie exclaimed to me, “they had all read me but it didn’t make any difference to them. I guess in Toronto almost everybody has a trans friend or work colleague or knows someone who knows someone who has or is transitioning. They had learned that we are not monsters, not perverts and not to be feared.

“Eventually the bar was winding down and guys started drifting off to their rooms. I decided it was time for me to turn in, too. We agreed to meet for breakfast the next morning. But not too early because they were getting together for a playground game first thing.”

“So did your friend call you or nudge you,” I asked with a smile.
“What happened in Orlando is staying in Orlando,” Katie smiled back with a wink. “You know what a nice change it is from 20 to 30 years ago when guys would only meet us and talk with us on the sly. That evening in Orlando I could have been one of their colleagues or friends or sister, even. They didn’t assume I must be on the make. I was just another person in the crowd.”

‘Thirty years?’ I thought to myself, ‘How old IS this girl?’

“So that must be another reason drag clubs are in trouble,” I surmised. “Why go to a gay bar when you stand a good chance of connecting with someone at your friendly neighborhood hotel lounge?”

“My thoughts exactly,” concluded Katie.

About a week after that exchange Katie wrote to me and mentioned our conversation about Orlando and how we crossdressers seemed to be getting more acceptance in the ‘real world’. She wanted to add a caution that the acceptance does not go for all CDs.

“I scoured the Internet for images to prove my point. See the diagram. The crossdressers on the left will attract negative attention wherever they go. But I found the images on the right and I’d be happy to be with them anyplace, anytime,” Katie proclaimed.

I grinned when I looked at the images Katie had found.


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Category: crossdressing

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.

Comments (3)

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  1. Laurence Kilbride says:

    Just had to tell you I laughed myself sissy just reading the last four words of the intro.

  2. Jill Suzanne Smith says:

    This article brought back memories for me. I was in Orlando for work about 20 years ago and like Katie I would get dressed up and go out after work. I would usually go shopping but one time I did drive to Parliament House. I was in my 50’s at the time and the people going in looked to be much younger so I chickened out and didn’t go in. It looks like I missed my chance to go since it’s now gone.
    I totally agree about the pictures Katie sent you. When people dress inappropriately it sheds a negative light on all of us. I’ve always dressed as any fashionable woman my age does and 99% of my contact with the public has been positive.

  3. Linda Jensen Linda Jensen says:

    I must apologize for the major factual error that I did not catch in proofreading. The gay club mass shooting that killed so many in Orlando was not at the Quest. (That is a small club in Clearwater) It was at the Pulse. So many people lost their lives it feels disrespectful to not have clearly recalled the name of the place of the carnage. My apologies to all.