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. Profile photo of Karyn Lobelia
    Karyn Lobelia 3 days ago

    After our marriage , my wife Shelley wanted me to start being metrosexual and to wear my hair longer .At first , I wore women’s lingerie under women’s pants and shirts , jackets and even shoes in men’s styles . Some , I started wearing my nails in gloss and later French nails . I soon started wearing natural makeup after starting on hormones . I was wearing ear stuts in both ears . Soon I started wearing diamond tennis s braclets and ballet flats or Mary Janes . At work I starting having noticing a real change in the women working under me started treating me as an equal and started treating me as just one of the girls . I soon was being told that I needed to defer to one of my female workers decisions . Soon I had a few girl friends at work take to a salon where I dyed my hair in honey blonde ombré streaks and put up in a feminine hairstyle and my brows arched . Soon after that I started wearing dresses and skirts , I was really changing to my more natural style .

  2. Profile photo of Staci Andrews
    Staci Andrews 3 weeks ago

    I crossdress because it helps calm me from the stress of feeling like a woman trapped in a man’s body. While I know that being in women’s clothing doesn’t in itself make me a woman it does help me feel better about myself. I have felt I am female pretty much as long as I can remember. I remember being very disappointed when my parents insisted that I was a boy. I have always like all the same things that seem to be associated with being female and detested my body and body hair etc. Crossdressing helps me have a bit of a visual representation of being female even though my body does not show it.

    For most of my life I have been told, and thought, that I was sinful because of this and so I have hidden it from everyone I know. I wish I had told my wife before we ever married. I somehow thought this would go away if I just tried hard enough, but now at 62 years of age I finally understand that this is just who I am.

    I need the crossdressing to help me hide the maleness of my body as best I can so the outside of me more clearly resembles the real me. Of course it is great if I can pass as a women in public because that would make it easier to be myself all the time. But just having the clothes on even if I don’t pass is a comfort.

    I still love my wife and want to stay with her and hope that when I do finally tell her that she can come to love me for who and what I am.

  3. Brown John 5 months ago

    Now I am 47 years old straight man. The desire to wear panty and bra exist since childhood. During teenage, the objective of getting into female inner wears is mainly for masturbation. Now, sometimes I will be in complete female dress inside my male attire for the whole day before ending with a masturbation towards end of the day.
    Some views says that I turn into female to create an imaginary female to have sex with. The desire to try different type of clothes also increases, preferably newly washed clothes worn by another female and not a brand new cloth. Sometimes there is a desire to go public in female dress.
    Not sure what is the truth behind all this desires.

  4. Danielle 5 months ago

    I love to dress, love being a woman, it comes from deep inside this need and it is a very big need! But when I go out I am very passable and getting better all the time, it makes me feel so good when I get asked where did I get what I’m wearing or complimented by women how good I look. Hopefully one day we will be able to go out without worries, but if more and more of us took that step, things may change quicker than you think :) I am lucky to have the support of my girlfriend in so many ways :) But I love to be fem, it feels like its the real me coming out!

    • Profile photo of Vanessa Law Author
      Vanessa Law 4 months ago

      You go girl! Be true to yourself Danielle!

  5. Ginger 5 months ago

    I have always cross dressed for the sexual thrill of it. I am very submissive in bed and like the feeling of being sexy for a man. It gives me a very feminine feel and I seem to be treated better as a woman rather than a man. Men tend to look at you as being more pretty when made up in makeup and lingerie. As a woman even though I am not passable men still seem to be more attracted to me. It may be a shallow way of looking at things and a self esteem issue but I like it when men call me pretty and want to sleep with me

  6. Slippy 5 months ago

    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.

  7. tara 6 months ago

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

  8. katie 7 months ago

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

  9. Brendan 7 months ago

    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?

  10. Candy 7 months ago

    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.

    • Profile photo of Vanessa Law Author
      Vanessa Law 7 months ago

      Woohoo Candy! :) It’s great you’re able to shine your light for all to see! *hugs*

  11. alberta 7 months ago

    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.

  12. Nayomi 7 months ago
  13. Miisty 7 months ago

    I am not a cross dresser but my by friend is i am ok with the wearing of women’s clothing but he becomes a women can you help me find a sight to get some answers?

    • Amy 7 months ago

      Hie everyone,
      As we all know,we all start out as females,then nature does its thing if we are going to be
      a Male or Female. I believe that there is a little of the “female” side is left in the male.For me,im TG,which means, transgender for the new people here.I am a M to F or a TG girl.I live my life as female,just as other females do.I am more comfortable than ever.

    • Amy 7 months ago

      For me,being TG has nothing to do with arousal or anything of the sexual turn on nature.IT JUST FEELS the way it should of been from the start.

  14. Alicia 8 months ago

    My reason for cross dressing well I always felt like a girl since I was 10 years old I always played with dolls and have tea party with my sister and her friends well one day nobody was home so I went to my sister room I found her panties and Bras once they were on OMG it felt so nice that when I knew I should have been born a girl I wanted to change my gender but my mother and father would not allow it back then it was a sin so I would take some of my sister and mom panties and Beas hide them and wear them in the woods acting like a little girl well as I got older I started buying my own women clothes I were them just about every day I also did Hormones for a year but they made me sick so I had to stop I am 56 now I feel like a woman I always wanted to feel like I will never change my men clothes are almost gone soon they will be all gone no matter what I wear I always act like a woman cause that what I am

  15. carryli servina 8 months ago

    I have 2 reasons why I dress. I prefer the feel of woman’s undergarments. And when I dress up fully (as I always have at least a bra and panties on) I enjoy the feeling of the fantasy I am someone else

  16. Nayomi 8 months ago

    Yeah! I love it.

  17. Steve 8 months ago

    I’m a 41 year old straight male, and yep!, I also did the pinch my mum or sister’s nighties and stuff when I was a kid. This originally started when I was about 8 years old then it stopped for a while, it then manifested again at about 13 years old. Items of clothing would go missing, it caused arguments between my two sisters.

    I kept my crossdressing to myself until I was about 36 years old and then one day I thought “f*** it” and decided to tell my family, then some of my friends, and some of my cousins. Not one of them has turned against me upon being enlightened.

    When it comes to shopping I just don’t give a rat’s what others may be thinking or saying, I’ve had a few people giving funny looks as I take my time looking at what I might be buying. There was one incident where a woman tutted and muttered to her accomplice “f***ing weirdo”, I then held the garment up against me and said “don’t you think it suits me then!”, I then called over to a shop assitant and asked what knickers would go best with it. Funny thing about this is I wasn’t actually buying for myself that day, it was Valentine’s day and I was buying for the woman that was in my life at then time. I say the ones that think crossdressing or transvestism is some kind of perveted problem are themselve’s the problem, and that’s their problem.

  18. chris 9 months ago

    Funny someone mentioned their mothers night gown. That’s the first time I remember wearing something girly. Unfortunately I’m a big hairy guy who doesn’t have the fine features to pass as a woman. I look ridiculous it’s not happening. I do sometimes put on my wife’s undies and I squeeze into a pair of heels when no one is around.
    I really wish I could dress like a young girl. I see them so pretty in their cute outfits. Sometimes I feel ripped off I wasn’t born a girl though I don’t have any homosexual feelings toward men. If I get reborn I hope to come back an attractive lesbian.

    • Amy 9 months ago

      Hie Chris,
      If your hairy,then you can shave it all and then just be careful one foods,you can do it !
      Cut out fried foods and cut the carbs,…i wish the best to you Chris,and others in the same situation…….

  19. nayomi2438 9 months ago

    Please forgive any typos, my mind just took off on this and I could not stop. Maybe its too long but it is what I feel.

    I’ve been cross dressing at some level for about 50 years. I am fortunate enough to have a loving and supportive wife that probably would love for me to dress up more than I do. How lucky am I, right? Fear of social backlash keeps me very private about my desire though we do sometimes go out with me in full dress as long as it is in a place that has a low risk of running into someone we know, places like downtown or a parks that are an hour or more from home. Nothing can explain the exhilaration of those times.

    Why do men cross dress? I hear this question about cross dressing so much. The response is usually the same old thing about there are as many different reasons as there are people. Yes there is an underlying truth to that response but I think there is something more common, more primal. The basic life cycle requires that we experience many stages of development. I also want to quickly mention that I do not believe that a cross dressers, sissy, drag queen, or trans person are the same thing. I am only talking about men that like to wear or dress up in under garments, clothing, shoes, or items that are accepted as specifically female.

    I believe after birth we, as babies sense things and learn to laugh, learn what is scary, and learn what is happy by events taking place around us. We learn to crawl then walk, we cry then talk. We develop personalities based on our experiences, the actions of people around us, and the environment we live. Our core instinct is to explore and evolve. But more primal than that, our instinct drives us to feel comfortable and protected, happy and loved. That feeling came to many children through the women in their lives.

    As we grow up it is simply natural for us to seek comfort and peace. Females often are the just the people that provide us that comfort, that peace. Perhaps it was only one particular person or many but through contact with them our comfort levels were met and our emotional needs were satisfied. This satisfaction and bond was emotionally connected and enshrouding in the essence of what made them feminine. This could manifest itself in lingerie, dresses, or whatever our exposure or perception of femininity was early in life. This was our first step to cross dressing. Putting on that garment; panties, bra, stockings, or dress was a potent moment that gave us an overpowering sense of pleasure in our souls, an epiphany. Our journey began on a road with no defined end. Every dress up moment is an attempt to experience that emotional fulfillment, that sense of pleasure so powerful that we will spend the reminder of our lives hiding, cheating, lying, or whatever it takes to have that moment again.

    It is so common to hear that cross dressing started so early in life. For many this had no sexual connection but as our bodies and hormones grew into puberty it was only natural for this connection to the female form to become a stimulating event too. There is a natural connection to ladies in underwear and sexual arousal. After all we are tactile people. Who can fault a boy if he became sexually aroused during puberty and then continue to seek comfort and happiness through dressing up as a sexual tool.

    This is my theory and I know there are always exceptions. I attribute that to every person having an individual life experience just as no two snowflakes can be identical, no two childhoods can be identical either. My belief is this explains the number of choices we cross dressers make in regards to the level of dress we seek, our choice of preferred items, and the style of cloth we prefer. What we had as choices when we borrowed from a hamper or closet or perhaps what we saw in magazines or stores when we enjoyed a fantasy moment greatly influenced how we progressed in our desires. As we continue to move through life the environment surrounding us either gave us room to grow or forced us to suppress our true selves. We all took different paths and came in contact with different people along those paths. Life thrust us into a variety of situations and we are now where we are.

    I believe in my heart and soul that so many more people are like us than we think. The shame that society has pushed on men is so emotionally damaging and hurtful to the point that I think many men are overly aggressive because they do not feel they can express themselves any other way. They hide behind the true feelings they have because expression would make them less manly. We think society frowns on the male finding joy, peace, and freedom in those things thought to be feminine but I am fairly certain that many “real men” have very sensitive feelings and would behave differently if they thought they could be accepted. My hope is that as time passes more men will accept their feelings and so will not threaten others that chose to make style choices that are not considered manly. Perhaps the inaction of those we fear will really be an admission of their own emotions and desires. What a wonderful world this could be.

    The statements in this message are to be considered my own opinion and not an official representation anyone else. I have no research data of any kind, other than my own experience, nor any formal datum to share. Actual life events may vary. If your condition persists, contact another crossdresser for support. Keep out of reach of children. Avoid prolonged exposure to narrow minded people. Keep mentally cool and stay away from dark places. Any resemblance to real persons, living or not is purely coincidental but definitely intended to be me. If you totally agree with the above opinions you’re crazier than I am. If you don’t agree that’s fine too.

    • G Sienia 2 months ago

      Thank you so much for offering your insight. You have the best answer yet than anything else I researched. I just needed to understand the pull of cross dressing for a seemingly “normal” man. I agree with you about the comfort of a woman. That makes a lot of sense. Again, well said!

  20. John 11 months ago

    I’ve worn full-cut, over-sized cotton panties BACKARDS for a bit over twenty years. Once in a while, I like to wear a camisole. I recently read someone’s theory that for SOME
    cross-dressers, they felt rejected by their mothers at a very young age because they weren’t daughters. I cannot confirm whether this theory has any basis or validity; but I can confirm the “gender rejection: experience at a very, very young age.

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