Why do men cross dress?

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.

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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  1. Kelly Jean 2 months ago

    It simply is part of who I am. My urge to slip on Mother’s silky nylon panties came naturally as a young teenager and from deep within me…..

  2. […] cross dress? Phew, an even tougher but great question. I explored this in some detail in my article ‘why do men cross dress‘. The short answer is that no one knows for sure and many men have different reasons for why they […]

  3. Profile photo of Giselle Reeves
    Giselle Reeves 9 months ago

    it is a compulsion that has gotten hold of me since i was 13 years old

  4. Profile photo of ...
    ... 9 months ago

    back in high school, as I have shared in various posts, it was something “I had to do.” Why? I did not know then but I believe it is something about my early development that left me in between, as it were. Growing up as a boy, I never really fit in any ‘peer groups’ and I did relate better with the girls. In one foster home I even played dolls with my foster sister. I had fun even with the paper cut out dolls and the clothes that just went on by bending the tabs over the doll body. As grew I found I was more intuitive than a ‘boy’ should be. I thought differently too never really getting into all the boy thoughts and activities. Oh, I tried to fit in with the boys but that never worked.

    Understanding why we cross dress is as easy as understanding women from a man’s perspective.

    How can we be stopped from cross dressing? In my experience that is a ‘not going to happen’ thing. I, myself, frequently put it aside up through my several marriages, sometimes for a year or more, but it always came back.

    Now I am this woman and am very happy and balanced.

  5. Profile photo of Sallysim
    Sallysim 9 months ago

    Simple really, I Crossdress because I feel happier and more myself as a woman. I feel it’s the real me. I love going out in public en femme, and being a man is just plain boring.

  6. Profile photo of Emma Mystique
    Emma Mystique 9 months ago

    My first crossdressing experience was when I was 7. I had a day off of school and I had inherited my sisters wardrobe, all of my boy cloths had replaced hers as she had left to be with her boyfriend, but 1 draw had one of her swiming costumes. As of course curiosity got the better of me and i decided to put it on. it was ok a bit snug in places and loose in other (as we all know eh girls)! Then what should happen.. yep my father walks in and asks what i wanted for lunch! shock, panic and a sence of self preservation, I dived under my bed and casually asked for a bacon roll! nothing was ever said about that day.

    My second chance to dress up is when I asked my mum if I could try on some of her cloths.. A puzzled look from a question from a 13 year old boy to ask, so we went into her room and got out all the things i needed: underwear, shoes and her work cloths. When i had finally got changed, she bluntly stated that this was the first and only time that I could dress that way, thinking nothing more about it there is where it stopped.

    I finished school, went to college, and when it came to going to university at 22 I’m not sure what, how or why it happened, a little voice whispered in my ear “well, what are you waiting for?” So roll on a couple of months later and I had acquired my very own underwear, some skirts and blouses, dresses and some heels – No makeup, wig or accessories to go with everything. Then after one heavy weekend of drinking (as you do in college) I decided to show everything I had to a fellow flat mate (who was a girl) I wasn’t nervious, apprihensive or worried about what she would say. she went through my things asking if I was gay, how long had I done it and thanking me for sharing with her one of my deepest secrets.
    After she had been through everything she said to me that most of it was too old for me! she then asked if I had a fem name when I was dressed (nope) so she came up with Emma, the following weeked we went shopping for some new(ish) things, which looked way better and fitted better on me than my original stuff I had purchased before. Uni came and went, I dressed up a couple of times, but still only by myself before I left for home I asked my flatmate if she could possibly give me one of her uniforms – as she worked in a hotel, with a little giggle she agreed and the day after low and behold, I had one of her uniforms. After a lot of moans, grunts and stuffings I finally managed to wiggle into it – and she did say I looked pretty in it which made all the effort more worth while.
    Now many years later and quite a few purges later, I finally told my mother that a liked to dress up now and again, she just smiled at me and said that she had known for quite a while what I did.
    My profile picture is when I was doing a fancy dress piece for a halloween day where I worked, I got a fair few comments of how pretty I looked, but we mostly had a laugh and a giggle about it.
    Which takes me to now.. as I am typing away on my keyboard in a nice summer dress, glancing at my pink toenails, I think to myself why havn’t I done this sooner? yes I had my little stash of things, but never got around to wearing them. but after I joined CDH, I tried on my old stuff – most of it fits me better then when I first bought it! I’ve started wearing my night gown to bed, shaved my legs a couple of times, painted my toes and am awaiting a reply to do a beauty therapy course..
    I am a bloke in a dress and to be honest I’m fine with that! One day I may want to go further but at 36 there is plenty of time ahead of me to sort it out.

    PS. thanks for taking the time to read this post I hope you have found it usefulful to get to know me a bit more.

    Hugs and kisses


  7. Profile photo of
    Sally come 9 months ago

    Why do we dress just makes me feel good

  8. Profile photo of Tammy
    Tammy 10 months ago

    In my opinion, there’s a larger issue that needs to be raised to the world. Why shouldn’t people experiment with gender? In modern society, are there any “good” reasons for traditional gender roles? The arguments would fill a book, but that’s no reason to avoid the discussion. In the meantime, the easiest answer to the title question is because we like to. That might not be much of an answer, but it’s no different than asking someone why they eat chocolate.

  9. Profile photo of Monika Sweet
    Monika Sweet 11 months ago

    why Men Cross dress… my pick, we are hard wired like that. We are born with the traits of both sexes to different degrees. Some has this balance, others are skewed to extreme ends… who are bent more towards being male stay males and never feel that urge to Crossdress while the ones who are on the other extreme go for extreme measures to transform themselves to be the woman they believe they are. The others who are in between these two extremes become Crossdressers with some or little inclination to transition.

    Why are we hardwired like that… that’s a question yet to be answered like numerous other mysteries about the human mind and how it works.

  10. Profile photo of
    Dianne Baldwin 11 months ago

    I love the feel of silky panties , bra and forms and I’m a lot more confident as a female.

    • Profile photo of Monika Sweet
      Monika Sweet 9 months ago

      Men have so little choice when it comes to clothing, style, fashion, etc.


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