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. Claire 1 week ago

    Hi. I’ve recently have the “balls” to crossdress. Since I was a little boy I have always been fascinated by the female body. I remember playing dolls with my sister and secretly try on my mom’s clothes.
    As a teenager I fought it. I tried some of my mf’s clothes a few times over the course of 15 years.
    I understand I’m a male. Heterosexual and I’m ok with it. I just have preferred being born as a girl. I’m 35 now and I finally found the courage to embrace my inner femme. I told my gf, my sister and my best friend. They have been supporting so far. I’m planning to be open to everyone eventually. I’m very happy now. No sense of guilt anymore.

  2. Marcia Mischief 1 month ago

    Well this is good question. I personally dress because it makes me feel sexy and naughty Marcia mischief is my femme name and I have been dressing for about a year now but I am also happy with my male self too and also happily married. My wife found some transexual porn on my computer about 3 yrs into our 16yr relationship it was awkward to talk about at first but I have always been attracted to crossdressers/transexuals we sat down and talked about it and luckily she was very understanding and encouraging with me and we have grown on it from there going further in the bedroom buying a strapon and she also helps me do my makeup as I said I’m so lucky to have her wish I had talked about it sooner xx

  3. Jennifergordon 1 month ago

    I’ve been asking myself for years why I like to wear girls things. It all started around age 12. With my mother’s stockings. I’ve had long periods of not dressing but the thoughts never go away. At first I thought it was a sexual thing but it goes much deeper than that. I purged many times to no avail. The urges never go away. The crazy thought of a “cure” is pure folly. I live day to day with it the best I can. Right now in fact all I want to do is slip into my stockings and garter belt. I don’t fight it anymore. Just embrace the girl inside. I want to be in a full nylon slip right now! Enjoy! Jennifer.

  4. Lisa 2 months ago

    I don’t think anyone should cross dress it is so hurtful to a family. I did not know my husband was a cross dresser intell we were married for years I think what my husband did to our realationship was unforgivable and I will hate this about him. I will never see my husband the way I used to and I feel has if I have been so use

    • Jennifergordon 1 month ago

      Hi Lisa! I understand how you feel. I started wearing my mother’s stockings and slips around age 12. I have no idea why I like to wear girls clothes. I fought the urges for many years to no avail. Like all crossdressers you finally have to come to the conclusion that the dressing will never go away. I apologize to you for what we do. Acceptance is the only true path. Please try to see his side of things. I hope and pray things work out for you both! Jennifer.

  5. Mikey 2 months ago

    Low self-esteem for lack of appreciation from women.

  6. Becky Johnson 2 months ago

    I dress as pregnant woman.I have walked with other pregnant women,we meet once a week to have lunch.

  7. Mandy 2 months ago

    Hi everyone I’m new to this page but I have a burning question that’s been driving me crazy! Any advice or opinion is welcome. A few weeks ago I found some ladies clothes in the bin at my boyfriends house, he claimed they were things from his ex this is just the start- a week or two later I also found a huge strap on under his bed! I haven’t seen it since and that seemed weird- a week ago I decided to do a little snooping and found a pack pack under his bed full of womens clothes ( skimpy stuff, dresses shirt ect) along with a blonde wig, fake breasts, bra and some lipstick and blush- things have not been so great lately but we have always been adventurous in the bedroom.. my question is is it possible he is sleeping with someone else or could he be wearing theses clothes himself.. as I figure if he is sleeping with some other girl, why would he need fake breasts or is it possible he is with a guy? I don’t know
    Despite all this I am not judging him for cross dressing- in fact if he came to me and discussed this I would not have judged, I would have accepted. It’s the confusion with the strap on along with the women’s clothes! I just don’t know what to think?!

    • Sarah Daniels 2 months ago

      Perhaps it was for games with his ex. Or maybe its just some junk she left behind. Only way to know is to ask, but its tricky for sure. Maybe just be up front and ask. If you are open and honest etc, and your relationship is going okay just take it slow I guess.

    • Claire 1 week ago

      Hi. I think only you have the answer. Only you lnoe your man. Many CD’s as me are completely straight and faithful. It just happens we like to be femenine and sexy from time to time. Society is full of double standards. Women can wear men clothes without problem and still be sexy. Why men can not?

  8. Cheryl Tallman 4 months ago

    I can’t really say I can relate or understand the urge to do this, but I do understand the need to be who we are. If this is what makes you feel like your true authentic self, more power to you. I’ve heard, to your own self be true… Best wishes to you all.

    • Jennifergordon 1 month ago

      Thank you Cheryl! It’s who I am. Fighting it only brings on anxiety and depression. My life runs much smoother accepting the girl inside.

  9. Maria 7 months ago

    Hi there

    Yes thanks for the article! I am a crossdresser and have now accepted my femme alter ego as part of me! It’s definitely a sexual turn in seeing myself as Maria, my sexy alter ego because you are the woman you desire! Ihave always had a fascination for female clothes and it feels right when I am fully dressed up! Been crossdressing since around 1992

    • Jennifergordon 1 month ago

      Hi Maria! I started with my mother’s stockings around age 12. I’ve purged many, many times to no avail. We all seem to have basically the same story. I feel complete when the clothes are on. I’m over being angry anymore. The only cure is acceptance. I finally enjoy being Jennifer. Don’t fight it! Just embrace.

  10. Pantyhose40 7 months ago

    Hello I know it’s been a minute on your posts but like to publicly say I’m a married closeted crossdresser except to my wife. I too like many started very young I know I was five raised with Three sisters and a mom I was only boy I couldn’t wait for sis. To leave there room so u could snag pair of pantyhose and it was the 80 s women everywhere wore them with mini skirts I never knew why I had that earge to wear that stuff but did always at first thought fetish but older I got wasn’t sure why in public I’m a manly man closed doors other than my wife I’m in pantyhose dress heels stuffed bra. But this stuff it came little bit at time like it got stronger. The feelings the fantasy I was thinking born wrong sex was I gay wasn’t sure knew of no one like this now this was before internet but when internet came popular I researched was surprised how many men ( straight) has same issue or desire I felt little better knowing there’s thousands out there thanks for the moment had to get it out there I’m loving it

  11. Michael 7 months ago

    I like the feel of women under clothing because it makes me feel sexy.I wear pantys and bra when ever I can under clothing I get some looks but that makes me feel good thinking someone know what I have on.

  12. Kelly Jean 9 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…..

  13. […] 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 […]

  14. Giselle Reeves 1 year ago

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

  15. Rosaliy Lynne 1 year 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.

  16. Sallysim 1 year 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.

  17. Emma Mystique 1 year 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


  18. Sally come 1 year ago

    Why do we dress just makes me feel good

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