Mommy, Where Do Crossdressers Come From?

| Jul 27, 2015
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Last time I wrote I told you about Mary. She is the long time crossdressing friend who had the theory that a large part of the attraction to crossdressing is that thrill in anticipating the danger that at any time she might be outed to the world. There was for her a sense of excitement as well as a sense of accomplishment when she would pull off another foray into womanhood while ‘passing.’ For her, crossdressing was not at all about seeking to be the woman she should have been. She lived in the moment to see how much like a woman she could be.

We talked about that over pre-dinner cocktails. She was full of comment and surprises for me that evening. Once we had settled at the dinner table and placed our orders with our server she started again.

“Remember that column you wrote about the pre-op transsexual who had caused a furor at a meeting when she declared that crossdressers weren’t really transgender?”

“I sure do. That broke up the meeting and killed that potential support group before it really got going.” This had happened at what was meant to be the founding meeting of a new group in Florida. The comment was probably made innocently enough and to me it was simply one person expressing one opinion. It didn’t have to be a correct opinion or an opinion I agreed with but to me she had a right to say it. Not so to several others who took the comment as a strong and discriminatory slight on their character. I just remember thinking every person has a right to an opinion and in a support group we should be respecting the expression of that opinion.

“I’m surprised you remember it and I’m surprised you read it. Sometimes I wonder if anyone reads my articles. What about it?” I could sense Mary wanted to talk about the incident, not the article.

“It’s a good thing I wasn’t there,” she said, “I probably would have been siding with the TS.”

“What?” I asked, “You don’t think crossdressers are transgendered?” I could not keep my voice down.

“Not really.”

“Of course we are. Aren’t we? We take on the role of the gender different from our biological sex. We may not feel we should be the other gender full time but as we put on our female identity we are in an identity different than our biological sex. That’s transgendered.

“Why do you think we go to all the trouble of doing the makeup, putting on dresses, feminizing our appearance and mannerisms if it Is not to be in the role that society expects of our preferred gender?” I continued, “Look in any dictionary. It will define that transgender has a wider meaning than transsexual. Transsexual is about actually changing gender from male to female or vice versa; transgender is about how a person feels he or she should be identified or how a person acts in relation to our society’s norms. That means that because we sit here dressing and acting as women but biologically underneath all this we are males then we are transgendered. Of course we are.”

“You may be right.” Mary said and then paused.

‘Oh oh, here it comes,’ I thought. Mary had a way of toning down our little debates by giving credit to my views and then hitting me with a totally opposite hypothesis. But what could be opposite here? She and I and many thousands like us dress to appear as female because we are comfortable with our female identity.

“It is true that during the time that I am Mary I enjoy and revel in the role of being a female,” she started. “It is just like that old musical number, I Enjoy Being a Girl. I really do enjoy being a girl.”

“That was the first number I ever performed on stage in my short-lived drag career,” I interjected.

“Of course it was,” she countered with a bit of mockery in her voice suggesting I should not have interrupted her. “However that enjoyment does not go beyond the moment for me. When I am not dressed and even when I am dressed I am not pining for the day when I can have my gender re-assignment. I do not look at those who have transformed and say, ‘that should be me. Caitlyn Trans-Jenner is not a model for how I want to live my life.”

“But how can you say you are not transgendered when you’ve told me what a thrill it is to be en femme and to be accepted as femme and even to have men sexually excited by the feminine image of you?”

Mary was quick to respond, “For me it is not much different than an actor who loves being on stage. Over the course of his or her career that actor will play many characters that exhibit personalities different than his normal personality and if he is good at it people will accept that characterization for the stage or movie role but not assign those characteristics to him away from the role. Nobody thinks Anthony Hopkins is a sadistic killer, do they?

“So I enjoy the role. I enjoy that sometimes men get aroused by my feminine image. As I said earlier I even enjoy the risk of being exposed in this role. However if a team from ‘Transgender Clearing House’ were to appear at my door and say, “Mary Francis you have just won a New Gender. You have won an all-expense paid trip to the Menard Clinic in Montreal where your penis and balls will be removed, a vagina will be formed and you will receive absolutely free two gorgeous C-cup breasts’ I would turn them down.”

“No, send them to me, please send them to me.”

“I could but I think you would turn them down, too. If you wanted to be a female you would have made the change long ago. I know you well enough Linda to know that there is not anything you desire that you will deny yourself.”

“But that doesn’t mean I’m not transgendered. It is just other circumstances that hold me back.”

“As I said, you may be right, Linda. It just doesn’t work for me. I am a male who enjoys playing at being a girl.”

“But where do these feelings of enjoying ‘playing’ as a girl come from then? Everything is done to program us males to be masculine. We are expected to enjoy rough sports. We boys are expected to like trucks and tools, fishing and hunting.”

“Do you enjoy any of those things, Linda?”

“Well, except for the sports, no.”

“Have you ever heard of Masters and Johnson?”

“The sexologists? Yes years ago but not recently. What have they got to do with anything?”

“Some years ago they published a book called Heterosexuality. It was basically an encyclopedia of human sexual behavior. I didn’t read all of it but of course I was interested in what they had to say about transgender issues. I do not recall them having much to say about transsexuality but they did deal with the heterosexual transvestite which they defined pretty well the way we would use the term crossdresser today. They give an interesting explanation for transvestite/crossdressing behavior. To them it is not genetic and not nurture, at least not conscious nurturing. I don’t know if they got it right or if it applies to many but it does seem to work for me.

“They grouped transvestite or crossdressing behavior under a category called paraphilia. You have heard of Pedophilia and Necrophilia? Those are pretty serious sexual aberrations where the behavior is harmful to others. Well, in their context, paraphilia are similar but considered much milder and not necessarily harmful to others. So yes, they considered us to be sexually attracted to clothes of the opposite gender but what was most interesting is how they considered that attraction came to be.

Now here I must pause and ask you dear readers. Are you following this so far? I am trying to recreate a conversation where I didn’t have a recording device and I didn’t take notes. I may not have things exactly as they happened or were said but I have the essence of the conversation. However what followed was Mary’s explanation of a long-forgotten or long-discarded theory of human sexual development. I’ll paraphrase as best I can. Masters and Johnson knew about pleasure centers in our brains. They felt those centers were there and active almost from infancy. Through these centers we learned our earliest pleasures and our reaction to certain tastes, touches, sounds, smells and even our pleasures associated with sex. According to them we did not have to be in or through puberty to develop associations with sexual pleasure. To them stimuli and associated responses in the age range of five to eight could determine what we find sexually pleasurable later in life.

“So for instance,” I remember offering, “if a young boy were to just happen to be looking at or touching a bit of lingerie and if that happened to coincide with a pleasurable sexual thought, that would be enough to influence his sexual behavior later in life? I doubt that.”

“It would be a start,” countered Mary, “there was a stimulus and a little reward. If the action were to be repeated the young lad might also find the reward being repeated, classic stimulus — response.”

“Kind of like Pavlov’s dogs?”

“Pretty much,” offered Mary, “Pavlov would say that if a boy were thinking about trying on his mother’s lingerie, for instance, and then trying it on and getting aroused pretty soon just the thought alone would be enough to cause the arousal.”

“That was me in a nutshell,” I laughed.

“Me too,” I remember Mary saying. She went on to say that the stimuli did not always have to be pleasant ones. For instance, a boy caught trying on his mother’s lingerie may be scolded and ordered to stop. The fact that act is forbidden and told is naughty could make the action more desired. According to Mary that was like the forbidden fruit. Being told we cannot do something makes us by human nature more inclined to want to try it: the reason it is being denied must be rooted in the pleasure it gives.

“That may be,” I countered, “but my earliest memories were of being caught trying on my mother’s bathing suit and later being rewarded in a funny way as my mom told her friend how cute I had looked. That kind of praise was hard to come by in my family. It was encouraging.”

“That works, too,” said Mary, “So our desire to dress, to crossdress, in my view, is not rooted in any genetic determination that you or I should have been born female. It is just that you and I as males that have become wired — yes by actions we were not really aware were happening — to enjoy the sensation of wearing female clothing and appearing to be female. I can’t distinctly remember but that wiring was probably helped along by me getting some sort of pre-pubescent erection while trying on lingerie.

“I am a male that has enjoyed success appearing as a woman. The success started at an early age with self-stimulation and reward. It continued as I ventured out of the closet and found the company of others who enjoyed the company of Mary. Each success and verbal reward brings more pleasure for me and thus more desire to repeat the action.”

“I think you are in a minority on that idea, Mary. I think most of us feel our desire to crossdress is rooted in more deeply held feelings of gender dysphoria,” I said without really knowing what that phrase meant.

Thankfully she didn’t challenge me to explain. “You are definitely correct. I know lots of us who genuinely feel they should have been born female because that is where their mind and emotions are. But for me to paraphrase your song ‘I enjoy being a boy playing at being a girl’.”

With that as if right on cue our after dinner coffee and two cognac arrived at our table.  “We did not order these,” I told the server, pointing to the cognac snifters.

“They are from the two gentlemen sitting at the bar,” she replied.

Mary looked over, raised a glass and smiled. The invitation was obvious. The gentlemen picked up their drinks to join us. ‘Let the games begin again,’ I thought to myself.

But ladies: what do you think? Is there anything to Mary’s theory? Use the comment area below to tell us what you think.

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Category: Transgender Body & Soul

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.

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  1. tasidevil tasidevil says:

    WOW, you open up a sensitive topic, Linda and one which you best stay away from. You do not want to be associated in any way with that list of paraphilas if for the legal issues alone. See

    When I first started giving classes at WVU on cross-dressing, the instructor was looping cross-dressing in with the paraphilas’ and I had to correct her. I know that sexual stimulation is big for many CDs but I place them in the fetishistic CD category. For those of us that enjoy dressing as women because it’s part of who we are, I remember the scene from “Transparent” where Maura says, “I’ve been cross-dressing all my life, cross-dressing as a man”

    That instructor is now a close friend with a PHD in counseling and I’ll ask her if her view has changed at all.

    • I guess that if we’re honest, most of us were sexually stimulated by cross-dressing, and it probably feature in many of our ‘wet dreams’.
      But since I ‘came out’ in 1984 cross dressing has given me great relaxation.
      But I have another reason for enjoying presenting publicly as female (which I was doing for eleven years or so prior to re-growing my beard).
      My main hobby is amateur drama; while it seldom fails to scare the shit out of me going on stage, it’s worth it for the adrenaline rush and successfully playing a part. So that also became one of my great pleasures of going out dressed – the fact that I was playing a part convincingly. I was always fully aware of what I was, but it was nice that people were ‘taken-in’ by the act. I’ve written a piece about that aspect, from the drama point of view, which has been published in a mag over here in the UK. I titled it “Street Acting” – because that’s what I was doing – close up and without the protection of a proscenium arch.