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Recreational Crossdresser: Is There Such a Person?

| Oct 19, 2015
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The twenty-fourth annual Southern Comfort Conference was the first one held away from Atlanta and the second one I have been able to attend.

Frankly, I loved their move to the Fort Lauderdale area and to the Bonaventure Resort and Conference Center. The Bonaventure had a very ‘resort’ feel to it and the conference facilities were first class. But that is not what I want to write.

Literally translated from French, Bonaventure means Good Adventure. I could certainly write about a few of those.

Ready for the course.

Ready for the course.

I could write about golfing very badly on a very hot day.

I could write about the experience of making my first seminar presentation. The topic was Internet Dating. Oh, could I write about that!

I could write about the fabulous pool party where more than a few very hot looking girls showed off the latest in breast implant surgery, suitably restrained by bikini tops, of course.

I could write about having a bit of one-on-one time with Jazz Jennings the ‘nearly from birth’ transgender teen who is now star of her own television reality show, I Am Jazz, who spoke at one of the conference luncheons. I sought her out to tell her what a marvelous public speaker she was and that in my years involved in education I could not recall a young person who spoke as well as her. I wished the straight A student well as she continues her education.

Jazz Jennings gives autographs.

Jazz Jennings gives autographs.

I met dozens of interesting people from all parts of the TG continuum. I could write a story about each of them but I have chosen just one. She and I spoke just for a little while and I did not catch her name but her personal outlook on the transgender world or more particularly her place in it struck me as unique. I now wonder if there are others who think like her. I wonder if I think like her.

I’ll call her Jennifer. That is a nice popular name that to me connotes beauty and independence, just as she presented herself, beautiful and independent.

We were sitting on one of the plush couches that lined the convention hallway of the Bonaventure. We were taking a break from the evening bar scene or perhaps it was the karaoke lounge.

You know how these conversations go -– How are you? How are you enjoying the SCC? Is this your first? Where are you from? You know how it goes. The conversation could have gone to a dead end and been forgotten but for some reason I was intrigued by her smile, her eyes and her sharp way of dressing and doing her makeup. She was not overdone like some crossdressers trying to stress their femininity or underdone like some transsexuals trying to show they do not need makeup to appear feminine. (These stereotypes do not apply to the majority but are simply stated to make a point. Jennifer looked very feminine and natural. At about 5’ 8” she seemed height and body appropriate, too.)

So I made a big assumption and asked if she was post-op, meaning had she had all the surgeries for what is now called ‘gender correction’.

That is when she floored me. “I am not post-op, pre-op, non-op. I am not planning on any gender re-assignment at all.” I noted to myself that she used the old term, ‘gender reassignment.’

“I’m sorry. You look so good and so feminine. I just naturally assumed you were TS. Are you doing this full-time?”

“Hardly.” Then she introduced me to a concept I had never thought of before. “I am just a recreational crossdresser.”

“A recreational crossdresser?” I repeated.

At the pool.

At the pool.

“Many crossdressers assume a female image because underneath it all they really desire to be a woman. They identify with females and they see themselves as emotionally female. It is circumstances of life, they say, that keep them in their male identity. Often it is job or family responsibility or the reality that they would not pass that well as a female but they think it is best to restrict their fem activity to when they can and how they can.”

“Yeah, that pretty well sums up me,” I reflected.

“At one time I probably thought the same,” Jennifer continued, “but as time has gone on and as gender transformation has become more main stream I have thought more about it for myself. A few years ago I came to realize that even if I was given the opportunity on a gold platter I would not change my gender. I enjoy being a man.”

“That will never make it as a song,” I quipped. “But if you enjoy being a man so much why is it you are here and why are you dressed like this?” I asked pointing to her gorgeous yellow dress.

“I have thought about that a lot,” Jennifer replied. “I do enjoy the presentation. I enjoy the compliments. I enjoy being attractive, especially to men.”

“Amen to that.”

TGF contributor Christine Zee's bikini photo shoot.

TGF contributor Christine Zee’s bikini photo shoot.

“I enjoy coming to Southern Comfort and sometimes to other conferences. Where I’m from I rarely get to meet other CDs and TSs. But most of all as Jennifer I just enjoy going out and doing things that women my age would do. I like to meet nice single men who will take me out to dinner, or to a show. I like to go shopping. I like to go to dances for the older singles. Occasionally I will go to church as Jennifer. I do all this without anyone that I know of knowing both Jennifer and the male me. No one but my two ex-partners.”

“But if you are doing all these things as a woman, surely you must want to be a woman?”

“Well, I have a pretty responsible job where, despite all the advances in society, gender re-assignment is not a good option.”

“What is that?” I was not sure I should have asked.

“I’m a boys’ PE teacher and basketball coach.”

“Surely they would find you some other teaching job if you were identified as gender dysphoric.”

“But I don’t want another job. I love the kids and we have a good chance of getting to States this year.”

“Then on the other side are you not taking some big risks?”

“Bingo!” Jennifer almost shouted, “That is the attraction of crossdressing for me. I have discovered I love the risk taking. The sense of danger that every time I leave the house or every time I walk through the mall I might be exposed: that is exciting. It gets my adrenaline going.”

“How so?”

“You know how some people take up sky diving or scuba diving or car racing?”

“I consider myself a bit of a drag racer. I’m always racing to get ready to go out.”

It was an inappropriate quip. Jennifer just smirked a bit and continued, “Our lives have become so programmed to safety that in our daily lives we do not encounter risk. Our ancestors lived with risk every day of their lives — risk of disease that could not be cured with a pill or a needle, risk of your horse bolting, risk of catastrophic fire, and risk of death or injury on the job. Risk was everywhere and it gave a certain edge to life. People had to be on guard against those risks. Now we are so programmed to safety that we rarely think of the risks in life. “

“Unless perhaps if you are a college student,” I interjected thinking of the latest campus tragedy that had happened the day before and making a hand gesture of someone shooting a gun.

“Yes, but even that sense of risk does not last more than a day or two. If it did we would get serious about gun restrictions.”

Jennifer was fascinating me. I wanted to get back to the topic at hand. “Are you telling me that you crossdress because you are a risk junkie?”

“Well partly I am. Maybe even mostly I am. I rarely dress just to sit around the house. When I dress I’m going out either shopping, trying on dresses and there is a bit of risk in that as technically that is illegal in my state. It has not happened in decades but I’m always wondering if the next person I come across in the mall will make an issue of my presence, if someone will call mall security if she sees me in the women’s rest room or if a store clerk will deny me access to the fitting rooms. It is always a thrill when I pass.”

“I have theories about that,” I interjected. “Stores have their own policies on risk aversion. They are very adverse to being sued or being hit with a human rights complaint. So they train their employees to look the other way if someone even somewhat passable shows up to try on some clothes. They don’t want to take the risk that we might be genuine female. The cost of an expensive lawsuit far outweighs the risk of anyone complaining about our presence so we get a pass even if we don’t pass.

“As for the redneck who might be reading us in the mall, we are all wary enough to be looking out for the next crazy with a gun. We never know when we could be saying the wrong thing to the wrong person so we just keep our mouth shut and look the other way.”

“So we know we’re harmless but they don’t?” asked Jennifer.

“That’s my theory but more in my case than in yours,” I flirted. “no one is going to be reading you.”

“Thanks,” she flirted back with a smile.

“You say you like to meet men for blind dates. So do I,” I continued, “Isn’t that classic risk taking behavior? Even genuine women know that.”

“Every woman knows that blind dates can be risky and knows to be on her guard,” she added. “I’m no different except for women it is an underlying fear for her safety. For me there is also the thrill to anticipate how he will react to me and the amazing sense of inner elation when his reaction is positive and the date turns out to be an enjoyable one.”

“Don’t you ever meet a man you would like to continue dating? I know I would love to have a steady squeeze but the men I meet are always ones I meet when I am on the road.”

Linda on her man hunt.

Linda on her man hunt.

“I’ve tried it,” Jennifer responded, “but very soon familiarity sets in and the thrill is gone. Unlike most singles I’m not looking for a life mate. I’m looking for adventure. And, like you said in your presentation, there are plenty of fish in the sea.”

“I did say that, didn’t I?”

I would like to say our conversation continued well in to the night but it didn’t. Some girls who knew Jennifer came by and rescued her from me. We promised to chat again but we never did. I last saw her that evening heading for the karaoke lounge with her three friends. I headed back to the hotel bar half-heartedly on a man hunt but soon to leave to make some notes about my conversation with Jennifer while it was still fresh in my mind.

The evening got me thinking. Are there many like Jennifer who crossdress more for the sense of adventure and risk than as a way of expressing our repressed feminine personalities? Is there really such a person as a ‘recreational crossdresser’? Surely there must be some sense of female gender identity present but I think she may have something there. What do you think?

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Category: Transgender Fun & Entertainment

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. Graham Graham says:

    I don’t have a “repressed feminine personality” … at least not that I’m aware of. Indeed, if I have a feminine personality at all (supposedly by dint of my wearing dresses and colouring my long hair, for instance), one can hardly say that I repress it! I expect some would argue that the fact that I wear dresses and colour my hair demonstrates a need to express a “feminine side”; however, I reject this – such behaviours aren’t proof-positive of a feminine side, but merely indicate that the way I prefer to present myself happens to be more aligned with how women present than how men present. In other words, just because society has arbitrarily determined that only women may wear dresses, the fact that I wear a dress doesn’t make me a woman. To me, how I present is just a part of my whole personality; I have other personality traits which are more conventionally masculine, and I don’t try to hide those either.

    On the other issue – the sense of adventure – there exists the possibility every time I leave my house that I may be verbally or physically attacked by anyone who takes a disliking to the way I dress. It’s a small risk most of the time, but it exists nevertheless. If I’m going somewhere new, or somewhere that I know there will be a lot of people, I get a little apprehensive, but I also get an adrenaline kick. So in a way, my life is a continual series of adventures which I have no option but to confront head-on.

    Given that what I’m doing is crossdressing (technically speaking), I guess that – by the above definition – I’m a recreational crossdresser …

  2. Jazz; I’ve only seen her on Youtube but she’s a real character. Very attractive, head screwed on well, very communicative and a good example from all points of view.
    Jennifer? My reaction is – what a very sensible lady! She has her own view and goes along with it, so good luck to her. We’re all on the spectrum somewhere, including her – no-one is right or wrong, just individuals. We are all completely different people in the rest of our lives, so why draw firm lines in the TG parts? It seems from your description that she looks great, and if she enjoys the buzz that’s great for her.

    • tasidevil tasidevil says:

      Most interesting, Linda. Sometimes I wonder if that description fits me as I love the risk of crossdressing. It’s just that I feel all too natural when dressed.

      For me the best book that really explains crossdressing is JJ Allen’s book, The Man in the Red Velvet Dress which is reviewed on Sister House ( She does an admirable job of describing the nine different types of crossdressers and one of them is what she calls the “social crossdresser”. It aligns closely with with your recreational crossdresser, so yes, I think you hit the nail on the head

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