You become friends with someone. Someone quite normal, a regular guy. Time goes by and much to your surprise, you find out he is a crossdresser. Here’s the intimate and social perspective of an (un)conventional transvestite.

Like any other Sunday I was feeling depressed over a guy and decided to go to San Telmo for a drink. Somebody had recommended a pub on Perú Street, so without giving it much thought I walked there straight ahead chewing my brains. I walked in and asked for a stout beer and immediately headed to the back. Yes, back there where the outlaws drink on Sunday to concentrate on the pool table fetishism.

I remember we were only a few people, the music was playing low. I found a spot next to a group of middle-aged men. I asked for permission to put my pint on their table and sat right next to an English guy. White-colored, with pink on his cheeks and a beer belly. I don’t remember exactly who stepped forward to break the ice, but I know that this very same night we ended up having the typical introductory talk of the first encounter. Without realizing, I was becoming friends with Sir Michael Doherty, originally from the cold lands of Manchester in the UK. 55 years old, IT analyst, who likes soccer and is a Manchester City big time fan. We talked about Carlos Tevez, Oasis, Morrissey, the Spice Girls, the Royal Family and of course, fish and chips. He told me he had just sold his house and moved to Buenos Aires, searching for a new life. Nothing unusual, I thought.

I started going to the pub with more frequency, becoming a regular, and the English guy–like a honourable beer drinking English citizen–already was. Weeks past by and that feeling of nothing unusual broke when I saw my friend had painted his toes with red polish. That certainly caught my attention and I must have made a joke about it, but the doubts stayed in the bottom of the pint. I thought that we all have our right to have our own eccentricity and that there was no difference to me between the Mike today and the Mike from a couple of days ago. That night I got drunk and I dared to ask. I remember Mike laughing of my innocence and his peculiar answer “Eccentric? This is not eccentric…I am a crossdresser!”

The confession led me to a variety of doubts and questions that, with time, erased from my mind the inaccurate and monolithic idea I had about crossdressing. “I must have been 3 or 4 years of age when I tried my aunt’s old fashioned corset and I felt something. The feeling was not sexual but there was a sensation in the nether regions”, Michael remembered. “When I got to puberty I started wearing my sister’s stuff. Then I went out stealing underwear from clothes lines and just sat in a field wearing whatever I had managed to steal that night. I was nearly caught a few times but I just had to do it”.

Crossdressing is not only expressed as a simple act of curiosity in the early youth for a lot of kids. In some cases, it is also sustained in time as a process, and that is not always related to the sexual orientation of the individual, as most of us might think. Society prejudices and feels threatened in many ways by a perversion like this. Society, as usual, sweeps under its moral carpet everything that might disturb its status quo, everything that might make us feel uncomfortable or checkmate us. In this matter, Mike says that society in general is quite accepting, as long as his actions do not disturb their certainties. But still, he went through a couple of violent episodes back in London. “I have been beaten up a few times. One time I was thrown through a shop window, which brings out the drama queen in me! It means I have suffered for my condition. I have had things thrown at me and I have been called a freak. Given what I sometimes wear I can’t really complain at being called a freak!”.

From ignorance, anyone would say that crossdressing is a type of behaviour related to sexual perversions, prostitution, promiscuity and sordidness. Let’s be clear, it can be, but not different from other personal fantasies or intimate disciplines. I dared to ask to Mike the ultimate question, the one that he had to give a lot of thought before answering. What is crossdressing for you? After a deep silence, he replied “Wearing women’s clothes. The thrill of seeing women in pretty, strappy things–I don’t actually have to be wearing clothes to get a certain thrill…” and he adds “Not being a man. There is a sexual thrill and a masochistic element. Being judged kindly by women who see me as less of a threat. I am sometimes patronized because I am seen as a boy rather than a man, I like that although it makes me feel guilty. I am still capable of an erection when I look at a woman!” Crossdressing is, from this point of view, something more subtle and more of an esthetical matter than we are used to think of. It’s about narcissism and developing contact with deep desire without being afraid of being sentenced by others. It’s the clothes, the touch of the stockings to the legs, the new nail polish, the act of making yourself someone you truly want.

“Lesbian women never mind too much, some really don’t care, others encourage it from a feminist perspective. There are some who think it’s pathetic and question why anyone would want to dress the way I do. Gay men in London were quite mean and bitchy, especially because I am straight.” When asked about how heterosexuals react to crossdressing, Mike says “Straight women largely don’t care, some think it’s pathetic and funny, some think it’s great fun and want to help me get dressed. Straight men will sometimes give me a look of contempt as though I’m not a real man. But the majority are fine with it”.

Why is crossdressing such a big deal? Why does society feel threatened? Why can’t we think outside the box? Why are we filled with fear and indignation? Why do they teach us this is wrong? So many questions remain unanswered still in the twenty first century.

I’ve been friends with Michael for the last 3 years now. I got to know the macho version of him, but I also got to know him in the raw. In fact, that has led us to a deeper level of communication and a greater level of conspiracy to achieve eccentric projects together. Mike is a man who is fascinated by dressing up as a woman. He’s unique but he can also be your dad, your brother, your literature teacher, your boss, your neighbor, even your couple or fuck buddy. Don’t judge or don’t think further, just be prepared for the thrill.

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  • Helena

    My husband is a crossdresser, when I knew it I did not know how to react…(we were unmarried yet)…”what does it mean in real life” I had to ask….and he had to explain very clear to me that he did not want to become a female…once that was clear, everything was smoother.
    He spends with me about half of his time as a male and half as a female, I learnt to love his female side, but I got in love with the male side….so I asked him not to avoid that one in our relationship.
    I have to admit he is very handsome as a man and absolutely passable as a woman..even a pretty one….We have learnt to enhance female atributes when crossdressed. He is tall and quite thin with gynecomastia ( I suspect this triggered his CD), not a small case, but not a gigantic one either, he fills more than perfectly a B cup and acceptably a C cup….but please do not get wrong, in his male clothes it is hardly noticeable. His thin body makes easier to get to get a female shape with some paddings…butt, hips, even breast. Despite his gynecomastia, in order to give him realistic proportion some padding is needed..but gynecomastia helps him to achieve a superb cleavage. As his hair is a bit receiding ( well quite receiding now, hahaha) he has always used wigs, he has a couple of them, very good quality and with a defined forehead, similar to those of Hollywood, difficult to notice they are fake. He took a make-up course…he is great with that…sometimes he makes me up. Besides he usually distract the structure of his face with glasses and a scarf. And plays very well with the fashion in order to hide his shoulders, that are bigger than the average woman….even though his face is not “angelical”(but passable, and indeed nice) as a woamn his body in female clothings puts me green with envy…specially with high hills. Out of our local town, he has gone out with me as female more than once, and I can say that we have the same number of men trying to flirt with each of us…most of them realized we are “lesbians” eventually.
    I was pretty astonished when he got a weekend job on a car expo as hostess (it last for nearly a year), those were hard money time for us. He hardly had to speak… but the funniest was that he was given the uniform…even underwears. They have just asked for a picture and measurements explaining the job, and was hired without an interview… when they realized he was a guy, they were happy with his behaviour and he was not fired.