Cross Dressing – fool a Harley rider with a biker kiss on a date.

Click Here

One of the reasons why it is so hard to label or categorize cross dressers is that the experience is unique for each person. Why we cross dress and how we do it are as individual as we are. As you learn more about other cross dressers, you will recognize some common themes in their stories, but once you begin to look inward you enter a place where the only thing cross dressers have in common in the fact that they are unique.

This is neither frightening nor surprising. As my partner Lori points out somewhere else in this site, how we dress, whether we are cross dressing or not, is a form of self-expression. It’s true we have a basic need to be clothed, but dressing extends well beyond that basic need. Cross dressers simply have the advantage of being able to express themselves in many ways, something women have been able to do for many years now.

How we dress is also determined by what we do while we are dressed. For me, going out as Yvonne is something I would like to do more of, so I have to work harder at my appearance. If my outings were limited to club meetings with other cross dressers, I may not feel as strongly the need to pass.

In my mind, there is no “right” or “wrong” way for a cross dresser to look or act, except to say that only you know what is best for you. Cross dressing is closely linked to who we are as people and as such can serve as a guide to better understanding ourselves.

The only blanket statement I’ll make is to say that you should experiment with your look. If you can afford it. I enjoy shopping in general, especially for Yvonne, although never, sadly to say, as Yvonne, so I can usually spot a bargain when I see one. Yes, folks, it’s true: I never pay retail. Now you know the kind of person I am.

Now where was I….oh yea.

Experimenting means having time and a plan. I usually get to dress no more than twice a week, sometimes only once. If I am planning on going out, then I keep the experimenting to a minimum, if at all. The reason is simple. The biggest obstacle to passing in public is having confidence. People will notice you if you are tense and nervous. When I feel good about how I look, I can relax and enjoy what I am doing. Part of what helps me feel good about my look is following a routine that I know from past experience works.

On the other hand, if I’m planning on staying home, I may try new cosmetics or a new way of applying them. Since the outcome is in doubt, I may not want the pressure of trying to pass. Most likely, I will still look OK, but not be convinced of that. My rule at this stage is if I don’t feel comfortable with going out, I don’t push it.

Another problem I had was finding clothes I enjoyed wearing that were suitable for public appearances. When I started dressing again in 1996, I never imagined going out, so I indulged in a lot of fetish clothing, and you know what I’m talking about here. When I started shopping for clothes that I could wear out and not draw attention, I bought things that I thought I should wear, rather than things I wanted to wear. I forgot the rule that we use clothing as a form of self expression.

The result was I felt awful wearing the stuff, wasn’t comfortable with myself in public and didn’t enjoy the dressing experience. So I donated it all to Goodwill. Where, I might add, I found a denim skirt that was perfect for what I wanted. Chalk that one up to Karma.

There are many sources of great information on how to choose and apply makeup, wigs and clothes and how to mimic feminine mannerism. The next few pages will provide links to many of these places. At the same time, I’d like to share some of my own knowledge and experiences.

Why do some men feel the need to wear women’s clothes? Is it purely for sexual gratification, or do they derive other pleasures from it? We delve into the psychological urges behind transvestism.

Irene is 29. She has long blonde hair and a well-endowed figure. Every three months or so, her family goes away for the weekend and Irene spends Friday night to Sunday morning doing exactly what she wants to do..

‘I begin my weekend on Friday night, as soon as the car has left. I fill a bath up to the top and then pour in an entire bottle of bath oil. I soak and then shave my body so there isn’t a trace of body hair. I’ll use jars of moisturising cream and talc and perfume. I’ll go to bed wearing a silk nightie, with some women’s magazines, and try to decide what make-up I’ll be using the next day, and how I’ll do my hair. When the alarm clock goes, I’ll get myself a coffee, with milk and sweeteners, and then take hours getting made up. My hair has to be just right and my eye shadow and lipstick and nail polish have to match what I’m wearing. Deciding what to wear takes long enough and sometimes I’ll have to change the lot if the effect I’m looking for doesn’t work. When I’ve got dressed I then have to make sure my seams are straight and my handbag, coat, scarf and gloves are right before going out, probably just down to the supermarket or round the shops.’

Nothing unusual in this account, you might think, except for the fact that apart from during these weekends, ‘Irene’ is called John and is a black-haired, rugby-playing bank manager with a wife and two children. Every so often his wife takes the children for a weekend with their grandparents, and John has a chance to indulge his very private pastime of cross-dressing.

Cross-dressing is another term for transvestism, and this and transsexuality and the association of both with homosexuality are often confused, even by some practising cross-dressers. Readers of Forum’s letters or Adviser pages will have noticed how often writers’ real or fantasy letters about their cross-dressing contain the almost inevitable question, ‘Am I turning into a woman?’ or the firm denial, ‘I am not a homosexual’. Is there a clear distinction, and what are the differences?

The accepted definition of a TV or transvestite is a man with a compulsion to dress like or otherwise personify a woman while still accepting the male identity. A typical transvestite would be a man who appears quite normal at all times when he is not cross-dressing. He is not likely to be homosexual, will prefer women as his sex partners and will most certainly not want to lose his penis. In contrast, a typical male transsexual will not identify in any way with his physically normal male body. He believes that he is a woman and is trapped in the body of a man. To him, his penis is a mistake of Nature and he will want to get rid of it.

A more formal distinction between transvestism and transsexualism is found in the diagnostic criteria accepted by most professionals working in this field. The American Psychiatric Association’s Diagnostic And Statistical Manual considers both behaviour patterns to be essentially disordered, and lists the criteria for transvestism as:

  • Recurrent and persistent cross- dressing by a heterosexual male.
  • Use of cross-dressing for the purpose of sexual excitement at least initially in the course of the disorder.
  • Intense frustration when cross- dressing is interfered with.
  • Does not meet the criteria for transsexualism.
The criteria for transsexualism are listed as:
  • A sense of discomfort or inappropriateness about one’s anatomic sex.
  • A wish to be rid of one’s own genitals and to live as a member of the other sex.
  • The disturbance has been continuous (not limited to periods of stress) for at least two years.
  • Absence of physical, intersex or genetic abnormality.
  • Not due to another mental disorder, such as schizophrenia.
Some professionals suggest there is not a clear distinction between transvestism and transsexuality and see it simply as a continuum, with the crossdressing man being at the beginning of an ever-increasing identification with the opposite sex, Most others accept that, as with most human activities, there are individual stopping points. The young man who initially puts on his sister’s knickers out of curiosity, gets a thrill and continues the practice, can stop at just that level and does not seem to have to move on to ‘stronger’ things. So you need not fear that if you have dabbled with the odd bit of cross-dressing yourself that you are on the inescapable path that eventually leads to requesting a sexchange operation. It would seem that the majority of transvestites are no more likely to go on to transsexuality than a social drinker is to alcoholism or an occasional cannabis user to injecting hard drugs. But, of course, everyone has to start somewhere and there is some evidence to suggest that the longer you cross-dress, the further along the continuum you may find yourself moving.

After his initial experiences, the transvestite will progress to one of three main groups:

  • He will stay with the type of garment or garments he first used and have a fetish-like attachment to them.
  • His initial preferences will expand and he will slowly move on to other clothes and finally into the wish to be dressed completely as a woman and to pretend for periods of time that he is a woman. But he will not want to go beyond pretending and will wish to retain his male personality.
  • The third group will fringe on transsexuality in that they will live and pass as women for extended periods. The only real difference between these so-called ‘secondary’ transsexuals and the full transsexual is that, again, like all the less extreme transvestites, they have no wish to actually be women.
Why do men cross-dress? One argument is that transvestism or cross- dressing is a way of offering a challenge to society’s preconceptions about gender. Some men cross-dress because they are unhappy at being men. Others didn’t mind the male state, but also like putting on women’s clothes occasionally, Some men cross-dress simply to make a passing social or fashion statement, and some because they have emotional needs that can only be met by the comfort that wearing women’s clothes gives them.

But for many transvestites, cross-dressing is an intensely sexual activity. Most transvestites have their first cross-dressing experience around puberty or in adolescence. The first experience is likely to be sexually exciting and the young person will carry on with the practice. However, transvestism is not just a sexual variation. There have always been plenty of men who get a sexual thrill from their cross- dressing, but the accepted view of most experts in this field now is that these are not the majority. Sex, particularly with other people, is not the main reason why most men cross-dress. Some transvestites do masturbate as part of their cross-dressing routine and it is easy to see why this is such an attractive prospect. After all, it is only like making love to yourself or with the idealise feminine image you have created for yourself. And you can do this without any fear of the rejection, criticism or disappointment which might come with attempts at intercourse with someone else—and you can create this image as many times and as often as you want. In most cases, the primary satisfaction is more cerebral: a feeling of comfort, a freeing of tension and intense enjoyment of total control.

A lot of the confusion and myth that surrounds transvestism probably comes from the fact that in the West it has always had a bad press and attracted hostile public reaction. Until recently, cross-dressing has been forced into being a very secretive activity. We have probably inherited some of our knee-jerk reactions to transvestism from the Old Testament attitude that cross-dressers would find ‘their blood shall be upon them’. Present-day disapproving Sun readers would find kindred spirits in the seventeenth-century subjects of the openly transvestite James I, who piously cried, ‘Elizabeth was king, now James is queen,’ while getting their vicarious kicks from reports of what the king was wearing today.

Why do men become cross-dressers? If we had all been lucky enough to have been able to follow the path laid down by Sigmund Freud for our development, there would be no problems and no transvestites or transsexuals. His master plan was that a boy went through five psychosexual stages of development—the oral, anal, phallic, latent and genital—and of these, the phallic stage, at about three to five years, was the most important in giving a proper gender identity. This was the famed Oedipus complex stage where the boy wants to possess his mother and sees his father as a rival for his attentions. Then, bang on cue, he see his mother or sister in the buff. He then makes the pretty smart deduction for an infant of this age that she’s had her penis cut off for being nasty to daddy and decides his won’t meet the same fate. He dumps his mother, takes up with dad and toddles off into the sunset with a copper-bottomed male gender identity. How the fact that, as anyone knows, every Jewish boy loves his mother survives this transition is a mystery that is beyond the understanding of us ungodly non-Freudians.

For those of us who have to follow a less than perfect route in our development, it is factors in the four areas of sex, gender, gender identity and gender role which will decide whether we are totally happy in our suits and trousers or will feel the need to reach for the lipstick and frillies occasionally.

Sex is the purely biological element of our sexual identity. That is, the chromosomes, hormones and genitalia that make you born a man in physical terms and will allow you to mature into taking the male role in the sexual act in later years. This is true in the majority of cases, but once we move on from the purely biological and into the other three non-physical areas, the influencing factors become more numerous and less clearly defined.

Gender and sex are usually synonymous for the majority of people and if you emerge from the womb with a penis, you will be of the male gender for the rest of your life. But since gender is to do with feelings, thoughts, behaviour and fantasies related to sex that aren’t primarily due to simple biology, the variations, the grey areas and the uncertainties can multiply rapidly. The picture is further complicated by each society’s idea of what is appropriate for males and females and by what cues, clues, rewards or punishments you have been given about being ‘male’ or ‘female’ since you were born as a blank page on which other people and influences would write.

Gender identity is our sense of feeling of to which sex we belong. Again, for the majority of people there is little problem with this. Most children will have the confirmed conviction that they are undoubtedly a boy or a girl by about the age of three, and this conviction about their ‘core’ gender identity will stay more or less constant for the rest of their lives.

Gender role is the public face of personal gender identity. That is, everything that you say or do that indicates to others to what degree you are ‘male’ or ‘female’, and from the feedback might be made to adjust your own gender identity. There is obviously an acceptable gender role in every society and men particularly learn their acceptable gender roles and internalise them from their earliest years. This is how the myths like ‘Real men don’t cry’ are born and maintained and any man who doesn’t pay at least lip service to them is open to social ridicule.

There are a few curious factors to be considered when we look at cross-dressing. For a start, it is a mainly male activity. Is this because women who want the freedom to express the masculine side of their natures in their clothes and behaviour can do so with far more ease? After all, nobody turns a hair any more at women in trousers, women with short hair or even women in ‘business suits’ and ties. We call it fashion, not cross-dressing. And women who smoke or drive motor cycles or indulge in any other activity that our parents might have seen as ‘masculine’ are similarly unnoticed and unchallenged. But when a man cross-dresses, he doesn’t just dress as a woman. He dresses as a particular fantasy of what a stereotypical woman might look like and act like if she had had an overdose of Barbara Cartland. Why also is it always the most self-proclaiming ‘masculine’ men—the athletic jocks, the servicemen, the policemen etc.—who are first to jump into drag if given the slightest of excuses?

What are men saying when they cross-dress? That they want to be pampered, spoilt and cared for, as they think the baby dolls they ape are treated? Women dress in severe suits when they want a share of the goodies men try to keep for themselves in this society – power and influence. It is reasonable that the other half of the human race would like a fair share of what women have—the chance to indulge their sensual natures and an unashamed love of pleasure.

Transvestism happens in societies which separate elements of human experience into female or male, insisting that women do one thing and men another, that women feel one way and men another. If you can accept that in your sexual preferences and practices you stand somewhere on a line that stretches from exclusive heterosexuality through bisexuality to exclusive homosexuality, could there not be a similar line for the ‘male’ and ‘female’ components that make up your own personality? The transvestite does, and perhaps even the most macho of men does so, too, albeit unconsciously. The only real difference here seems to be one of degree and the fact that the transvestite gets into ‘her’ closet with a little bit more self-awareness and honesty about his own needs than the rest of us.