Crossdresser Heaven

Why do men cross dress?

Girl friends and wives want to know.

Why do men cross dress?

Why does my husband cross dress?

How can I make him stop cross dressing?

The unfortunate truth, is that there is no simple, one line answer to these questions. If there were, you probably wouldn’t be reading this article, and the debates on this topic would be silent.

Why do men crossdress?

Why do men crossdress?

In my personal experience, the fascination with woman’s clothes started when I was very young. I must have been about four years old, and I remember going to great lengths to procure and then wear my mom’s nightie. My most vivid memory is as a teenager, nervously buying a pair of pantyhose from a local supermarket and then wearing them home under my pants.

I felt (and still feel) a need to wear woman’s clothes, and I can’t quite explain where it comes from. The media like to think of cross dressing as a sexual perversion, and so naturally they see the desire to cross dress and purely for sexual gratification. The problem with this theory is that when I (and many others) first felt the desire to cross dress I didn’t know what sex was.

Many cross dressers I’ve asked describe the need as ‘feeling more comfortable wearing woman’s clothes’. This is sometimes (but not always) coupled with the desire to be seen as a woman. To not just dress like a woman, but behave like one as well, to wear make-up and otherwise pass as a woman. There are others who cross dress for sexual excitement. The need to cross dress is indeed a spectrum.

That still doesn’t answer the question why do men cross dress?

Marcy proposes a few interesting answers to this questions.

One argument is that transvestism of 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 to put 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.

Yet the true reason why men cross dress remains somewhat of a mystery. It is intensely personal, often confusing and sometimes guilt ridden. I’m hopeful that as society grows more tolerant of diverse gender expression we will see more cross dressers and transgendered stepping forward to share their stories. Without the need to justify their behavior, and no longer shamed by society perhaps we will be better able to answer this baffling question.

Comment and let me know, I would love to hear- why do you cross dress?

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About the Author

Vanessa Law is a women enjoying the freedom to be who she is every moment of her life! She blogs about the transgender journey at Please comment below and tell me what you think!

964 Enlightened Replies

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  1. Slippy says:

    For me, the desire to cross-dress comes from a feeling of ugliness as a man.

    I’ve always found women so attractive, desirable, and feel myself so undesirable, that I get great satisfaction being figuratively “on the inside, looking out from” the alternative sexuality that I admire so much. So in this respect it’s narcissism and vanity, and more of a need not to be me than to pass as a woman. (I know I can’t pass as a woman, but I still get there psychologically.)

    Plus, it’s less work than body-building, which I guess is a vanilla alternative.

  2. tara says:

    my wife loves me dressed and we have matching lingerie and clothes.

  3. katie says:

    I feel more comfortable when I am wearing women’s underwear and clothing but my wife is not very excepting of my desire

  4. Brendan says:

    Though I am without any interest in wearing women’s clothes (and, most of the time, men’s clothes too), I still find the subject of transvestism fascinating.
    It has me curious to think of where such a biological phenomenon has been seen elsewhere in nature. I think of birds and how the males are generally those with the brighter and more colourful plumage as compared to females. Perhaps transvestism is an echo of our ancient relation to the avian species?

  5. Candy says:

    I love to crossdress . I am very passable as a woman. I get complemented all the time when i am out in public. The reason i crossdress is i love the way womens close feel on me . i also love to feel sexy and fem. I have never had a problem while dressed out in public.

  6. alberta says:

    Dear ‘I love it how a person should just be what they fill inside ones yourself. hell’s bell’s to all those that can’t seem to talk about a ‘guy in dress’ out at 12 noon somewhere in public anywhere. it also should be understood that the ones that hate’ just by seeing the dress on a guy. they just are not ready to mind there own bizness’ someday a major movement will happen I just hope in I am around for it. the public will be hate free in the us states Till then I’ll stay home where it’s safe. truly yours. a.k.a stick pussy.

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