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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Latest posts by Vanessa Law (see all)

  1. Profile photo of Ashley
    Ashley 5 days ago

    My reason for dressing is because I love to feel, look, and act like a woman. I want to know fully what it is like to be a woman in every respect, to feel sexy and adored by men, to feel the eyes of the room on my delicate body adorned with pretty clothing, and to feel all the sexual energy I do choosing what I want and who I want as a woman. It just feels so powerful and sexy when I dress. I think the best way to sum it up is that I adore women so much that I want to be just like them, and become more and more girly every day.

  2. Profile photo of Carol Taylor
    Carol Taylor 6 days ago

    I cross dress because I enjoy it. I love wearing women’s clothes – or, my clothes as I prefer to think of them. I love how they make me feel, and for me it’s something really positive. I can understand and believe that for some who cross dress, they are making a statement about fashion or gender norms, but I think that for most of us, it’s who we are, who we want to be, or even who we hope to have the courage to be – one day

  3. Profile photo of Patricia Marie Allen
    Patricia Marie Allen 3 weeks ago

    Why do I cross-dress… Short answer — it’s who I am.

    Having discovered my feminine side at the tender age of 8 or 9, I’ve gone through several stages. In the beginning it was simply the fascination of looking like a girl. Later, in my early teens, an erotic element developed as I developed an interest in girls.

    As an aside: a dirty little secret. I used to dress up from the skin out, being sure to securely tuck the male equipment, then stand in front of a full length mirror and lift my skirt to see my panties. Part of that was erotic, part of it was seeing illusion of being female in the extreme. But that aspect lasted only a year or so.

    I lived in the mistaken idea that this was just something I did because I was bored. A hobby of sorts. I knew for sure that once I was grown, once I was married, I’d leave it all behind as an adolescent/teen memory. Even after got married and discovered I hadn’t left, or was the couldn’t leave, it behind, I stubbornly kept it as a separate part of my life, driving a wedge between the feminine expression and my male persona. I knew guys who were self-conscious about their hair and use what I termed as “beauty products” like shampoo and conditioner on their hair and I prided myself that I wasn’t wimpy like that. I washed my hair with Ivory soap in a “manly” fashion, not like those wusses who used that girly stuff.

    It wasn’t until my wife caught me dressed that I finally researched and made an attempt to reconcile myself with my feminine expression. It took years before I could unify my feminine expression with my male persona and just be me without any separation.

    I now refer to myself as a feminine male. My male body has served me well and I have no real issues with it. OK, so if my wife wouldn’t freak about it I’d have modest breast implants. But I’m happy with my role as husband, father and grandfather and I wouldn’t give up one aspect of that for a moment.

    Still I don’t own any men’s underwear, wear a bra w/breast forms 24/7 and I only have one pair of men’s pants and two men’s shirts and no men’s shoes, yet my closet is bulging with clothes, a small portion of which allows me to masquerade as a typical male, even though they came off the women’s rack. A sad commentary that women are allowed to be as masculine as they want, but men can’t even take a baby step toward feminine.

    Why all this for a man who can’t even imagine transitioning? As I said, I cross-dress because it’s who I am.

  4. Profile photo of Sheila Tampa
    Sheila Tampa 3 weeks ago

    Hi Girls,

    Like many of the previous commenters, I really don’t know EXACTLY why I crossdress. Like many others, I started trying on my mother’s clothes sometime between age 7 and 9. I especially loved panties and slips (and still do at age 71). My crossdressing at home was limited to the few occasions when I would be the only one at home and I knew the others would be out for at least a couple of hours or more. I occasionally would try on my mother’s high heel pumps and a dress. I did not try makeup, and I did not have access to a wig.

    When I moved into my own apartment, I started buying women’s clothing from catalogs. I didn’t buy a wig and makeup until I decided to join a Tri-Ess chapter. I felt guilty at times, and like so many others, purged my entire feminine collection completely at least 2 times. But, around age 40, I started a new collection, including quality breast forms for the first time, and just accepted that I loved dressing as a woman and acting as a woman when dressed.

    I never felt like a “woman trapped in a male body”, and was OK being a guy most of the time. Now, at age 71, I am very happy to be a crossdresser. I regularly attend the meetings and dinners of a TG social and support group. I have also attended 6 Southern Comfort Conferences (SCC) and will be attending this September’s SCC. SCC is probably the most well-known TG gathering in the USA (and maybe the world). I attended one Keystone Conference, which is another popular TG conference. I occasionally go out (but not very often) completely dressed as a woman.

    Back to the topic’s question … why do I crossdress? I’m guessing the following points all play a part:
    1) from the very first time I tried it right up to the present, I just found it to be exciting and very pleasurable;
    2) I have always been a bit of a non-conformist, and I think the fact that crossdressing was (and still is to a lesser degree) a “social taboo” makes it even more exciting;
    3) I’m very liberal and open-minded, and with that mindset, I feel there’s nothing wrong with crossdressing and why not do it if I like it;
    4) and, finally, maybe the simplest reason … crossdressing is just flat out FUN!

    I often kid my fellow crossdressers and say … “I know crossdressing is not exactly a hobby (it’s more than that), but if it were counted as a hobby, it sure beats bowling or stamp collecting! (Sorry, bowlers and stamp collectors … no offense intended).



  5. Profile photo of Jennifergordon
    Jennifergordon 3 weeks ago

    Panties forever!

  6. Profile photo of Jaye Dee Bowman
    Jaye Dee Bowman 3 weeks ago

    Why do I crossdress???? I do it because it makes me feel more at ease with myself. I also have a “need” to feel the snugness of my bra(w/forms), the silky feeling that my panties give me when I’m wearing them, the joy of stockings or pantyhose on my legs, the sound of my heels on a floor, the rustle of my skirt when I walk, the feel of my blouse or my dress on my skin, the length of my hair tickling my neck, the joy of applying my make-up.
    This is how I become the girl that lives inside of me and this is how I let her out. If I could, I would transition totally and never look back to the male part of me that always felt guilt and ashamed. THAT IS WHY I CROSSDRESS

  7. Profile photo of Jennifergordon
    Jennifergordon 3 weeks ago

    I love my panties, nylons and dresses. Not giving them up! Jennifer.

  8. Profile photo of jamey Trusty
    jamey Trusty 3 weeks ago

    I have been crossdressing since I was a child don’t know what really started it. I almost feel like a split personality when I dress male am all male and when I dress woman its the same. I have tried going out in public but like the knowledge and grace to fully pull it off i honestly fell like that man in drag. Recently with you help and a newly purchase you a cheap down under I really feel more like a woman. I am saving my money for a better down under but this is the first time I really feel complete. I have tried all the taping and was miserable and confined. I am trying to learn more and more on how to blend in. I also want to add i have been married for 22 years and she is very supportive. I also have 2 grown daughters who know my female half and also are supportive.i am 59 years old and retired military also totally work in a mans world. My stepson is the only other male who knows i exist. I try to keep my secret from my grandsons and don’t want them to misunderstand. I do most of my dressing after work and behind close doors and if I do go out it is way out of town so there is very little chance of being recognized by one of my coworkers or friends. I tried once in town and a no longer so call friend spilled his guts to my then coworkers. I worked real hard to discredit him saying you know me guys you honestly believe I Crossdresser. I am real country so I was able to convince them. Little do they know so I stay out of town or state if I decide to go out in public but haven’t had the best luck in pulling it off. Looking forward to learning more ways to blend in so I can enjoy my feminine freedom.

  9. Profile photo of LingerieLouise
    LingerieLouise 3 weeks ago

    When I was going to high school my mates dared me to go to the annual dance dressed as a girl. It was the local boys and girls high school social get together. I knew a girl who went to that school and she lent me a uniform and gave me basic instruction to pull off my stunt. All I purchased was a wig from the local party supply shop. My female impersonation was meant to be a joke and I was to announce myself by taking off my hairpiece while dancing. I was astonished to discover no one at the dance saw through my disguise and I enjoyed what I was doing like I could not believe. There I was performing what I could best describe as a female acting roll. I was fascinated to see how long I could continue with this masquerade until I revealed myself. People were saying things like, ‘now you have to dance with the boys tonight’ and ‘the boys want to meet you’ I was truly being accepted as a girl when all the while that was not really my intention. Of course, I saw my mates that made the dare on the other side of the hall when I spontaneously decided, because of my success as passing as a girl, not to disclose my identity. That night no one knew I was a guy. I decided to leave early when the first girls left, because I felt I had achieved something special and didn’t want to take anymore chances. The ironic thing was that when back in school with my mates they all said that I did not go to the dance, that I chickened out. I could not convince them that the tallish smiling blonde they laid their eyes more than once was actually me. My mates simply did not believe me and I felt it was something special indeed to be a boy who could pass as a girl in the close company of so many people at a dance.

  10. Profile photo of Cecily
    Cecily 1 month ago

    Hi I’m Cecily
    I am new here I am more curious at this point then anything I have had these feelings more then likely for a while but have just started coming out lately I am married so it’s hard to figure things out but I am trying to work on it not quite sure of what my style is but hopefully I can work through this and figure out how I want to do this

  11. Profile photo of Rosaliy Lynne
    Rosaliy Lynne 1 month ago

    Why do I crossdress? I never really came up with an acceptable reason for it. As a child I was always different but no one, not even I, understood why. In grade school, I did not relate well with other boys and never really got into boy activities. Oh I shot hoops, jumped rope, climbed the bars at the park, played cowboys and indians and other kid games but I just never really fit in.

    In high school, one day it just hit me, I had to dress as a girl. Believe me when I say I spent a lot of time trying to figure out why. I enjoyed the change of clothing but that did not seem reason enough after all, boys were taught not to wear girl clothes. Actually, I believe it was part of religious education that boys did not dress as girls and vice versa.

    So I decided to acquire some girl clothes. If the things I got fit I kept them to wear secretly and the rest I threw out. There was an element of sexual erotica too at first but that didn’t explain the need either and that was short lived anyway.

    I have always had a good eye for what to wear so it wasn’t a fashion statement. At first I enjoyed being the girl some times and then switching back to the guy.

    Guilt, fear of getting caught dressed that way, being teased or called names, those thins also figured in the mix and made in necessary to hide that part.

    The only thing I decided made any sense was that the girl side was part of who I am and since that was the case it could not be wrong. Not that simple though. It took years before I accepted that and embraced this other side of me. Eventually I realized that this is who I am and so here I am today, this lovely woman who still does not know why I started crossdressing but who now also realizes it doesn’t matter. I am who I am and that is good enough for me.

  12. Jennifer Elise 2 months ago

    Like you, I started dressing from an early age. 4 or 5 maybe. Truth be told, I can’t remember a time where I didn’t wear women’s clothes. Even when I was in the Army, I found a way. It certainly didn’t start out as sexual. At 4 I didn’t understand what sex was. It just felt right. It was the only time I felt like me. Thus is still the reason. It’s not that I don’t like men’s clothes, I just feel more comfortable in women’s clothes. I wish it were accepted. I hate that it’s even called crossdressing. Ellen isn’t called a crossdresser because she wears what are traditionally men’s clothes. I just want to be me, and I only feel that way in a skirt or dress.

    • Profile photo of Ricki
      Ricki 3 weeks ago

      I do agree we have a double standard when it comes to dressing .women dress in pants and shirts and lately in their pjs and it is acceptable however when a guy wears a dress the name calling begins . I love a dress and the freedom it provides far more than jeans or pants I guess if women are giving up dresses the we should do it for them lol

    • Profile photo of Tracey Rose
      Tracey Rose 3 weeks ago

      very true!

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