Why do men crossdress?

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.

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.

En Femme Style

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?


More Articles by Vanessa Law

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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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Noble Member
5 years ago

Hi girls, it’s Scarlett and I wanted to ask this question in a different kind of way by asking you when your wife found out, one way or another, that you were a cross dresser, what were the reasons you gave her (after she stopped freaking out) as to why you love the thrill of cross dressing? Now I’ll start with not the reasons I told my wife why I cross dress because she still doesn’t want to know and wants me to keep it private and not cross dress while she’s present in the house. I also have to… Read more »

Edmund Dauntes
3 years ago

Hello all. I go by Edmund Dauntes. I am a 60yo straight cross dressing man. I love the feminine form, I love to look at, smell, fantazize about beautiful wemon. I am married 26 years, my wife would not approve. The reasons that I cross dress go way back. I will list them in chronographal order. At birth, I was placed between my mothers breasts to suckle. She used to wear those nylon night gowns. I believe that created a powerful impression in me For a great appreciation for boobs and slippery nylon fabrics. I still love those things today.… Read more »

Ichiro Kobayashi
1 month ago

As a man who crossdress or I should say underdress, Why? Short answer: It’s comfortable to wear. Why? Complicated answer: For Japanese sports PE bloomers. It’s comfortable, it retains heat in winter 🥶, to me it looks like a cross between men’s brief underwear and women’s “granny" brief panties, and lastly I can feel open and relaxed while wearing Japanese sports PE bloomers. Why? Complicated answer 2: For women’s panties . It’s comfortable, I can get in touch with my feminine side, I can wear something different, I can feel sexy, and it’s soft to wear. Lastly I want to… Read more »

Active Member
1 month ago

Comment and let me know, I would love to hear- why do you cross dress?   Short answer? I don’t know for sure. A few years ago, I saw some nice looking women’s clothes and said to myself that they looked nice. I’d like to wear that. Slowly, I started buying pieces, here and there, eventually having enough to make outfits. I liked it (my wife wasn’t so pleased). I had no plans at all to transform or anything like that. I frequently went against the grain of society and see crossdressing as being no different. There is no dysphoria… Read more »

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