Men Dressing as Women

Men dressing as women, whether for performance or personal choice, is nothing new in cultural history. What’s changed dramatically in the last few years is the acceptance of transvestites, at least in Western cities. Men not only have more and better choices in clothes and accessories to turn themselves into women, they can acquire those products with great ease, thanks to better shops and, especially, the Internet.

Men have dressed as women for performance and comic effect, as well as enjoyment, for centuries.

Because women were not allowed to appear onstage, men dressed as women in theatre, beginning with Greek drama and carrying on until the 17th century in England. With so many of Shakespeare’s heroines disguising themselves as boys, actors found themselves double cross-dressing – boys playing girls playing boys. For audiences, this was all perfectly acceptable.

Even when women began to play women, the concept of men dressing as women did not leave the stage, especially in Britain. What changed was that the male performers tended to cross-dress for comedic effect. The music hall and pantomime stages regularly saw men in the most absurd drag playing decidedly outsized characters. This carried over when comedy troupes brought their work to television, most famously with the Monty Python team, who regularly employed drag to hilarious effect.

In America, men in drag were popular on the vaudeville circuit, but otherwise not widely seen.

Men who dress as women for their own pleasure have probably been around as long as civilization itself. The word “transvestite” was coined in the 19th century, around the time the act was categorized as a mental illness. Until recently, a man caught in public wearing women’s clothes was subject to arrest or worse, but society has grown considerably more tolerant, allowing everyone to express themselves far more freely.

It’s commonly assumed that all transvestites are gay, perhaps because the only exposure many people get to cross-dressing is seeing men in Gay Pride Parades, where they often dress in outrageous costumes. However, the men who do so in the parades usually only dress that way for a laugh once a year. In fact, the majority of transvestites identify as straight and are very happy being men – they just enjoy dressing up as women sometimes, or even just wearing women’s underwear.

It’s also assumed that transvestites derive sexual pleasure from dressing as women, but again, this is very rarely the case. They are just comfortable and happy when they cross-dress. The bulk of the discomfort associated with men dressing as women comes when a man decides to tell his partner or friends about it. Because so many people assume it has a sexual connotation, it can be difficult to understand. Fortunately, there are a number of support groups that can give information and assistance.

Support groups are more commonly used to help men who want to pass as women do so convincingly. The Internet has opened new vistas of possibilities for men who previously had to rely on information from theatrical circles to learn how to perfect their look. Moreover, men no longer have to look for women’s clothes and shoes in large sizes – a number of designers cater specifically to transvestites, designing clothes and shoes with men in mind so that they are more flattering, comfortable and realistic.

If you’re just beginning to explore your cross-dressing, you should start simple. Take your time practicing the art of walking naturally in heels, for example. As is demonstrated to great comic effect in Some Like It Hot, there’s a serious learning curve to getting the movement right. Nor do you want to wear close-fitting, attention-getting dresses until you are comfortable moving as a woman.

Shops that sell women’s clothes in men’s sizes will also have wigs, makeup, breast forms, bras and other support lingerie. They will also have advice for applying makeup to look as feminine as possible. Some men turn out to be prettier and sexier than real women!.

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