Why do men cross dress?

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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444 Comments - Leave a comment
  1. Blake says:

    To Samantha,
    Watch this video Samantha…the boy in this video might give you the courage to be you in female clothes,I think this boy is VERY courageous for doing what he is doing…an INSPIRATION for anybody..click on this link or do a copy paste..

    http://www.huffingtonpost.com/2011/10/26/bobby-montoya-girl-scouts_n_1033308.html

    • Samantha says:

      To Blake

      thank you very much for the link to this video and thank you for all your help i thank you very much i mean before i came on here and started talking and reading i felt all alone with what i liked to do so i always felt wierd and out of place so now im just glad that there are pepople out there that think the same way i do :) i have to say you all helped me a great deal to relize that im not alone in this world and i dont know how to thank you enough for all of your insparation :) i think tmro and more often then enough im going to be trying to start going out dressed :) cauyse when im dressed i always feel so much more comfertable and it makes me happy and thats all that matters :)

      thank you
      love Samantha xoxox

  2. Blake says:

    This is a better link….its not really about the girl scouts to be my point im trying to make,the first half of it is tho…

    http://www.inquisitr.com/154249/7-year-old-boy-wants-to-be-a-girl-scout/

  3. Blake says:

    To Samantha,
    Just start out first wearing just a skirt,nothing else but a tank top or a regular shirt of what you would normally wear..then take it from there in stages

    • Samantha says:

      To Blake

      yeaa i will except im not going to start off with a skrit, im going to start off with some girls skinny jeans and then maybe after tht ill do a shirt as well and then my high heels and then off from there :) i mean when i first started out at all i started off wearing a thong actually and now im trying to wear my skinnies out in public and after that then the skirt and tops and more :)

  4. Blake says:

    Samantha,
    If you like thongs,which i do to,i get mine custom made so a guy has enuff material in the front to hold yer “stuff”…..here is where i get mine made http://www.swicthongs.com …any colour any style and so on,check it out you will like them.Val does a fantastic job on making thongs for guys.When i was wearing jeans,i only wore Levis 518 super stretch,they are snug on the butt makes the butt look nice,or Hydrolic jeans,both are girls..

  5. Chasity says:

    I am a crossdresser and have been for a very long time. Is there some advice you could give me for my new wife to explain to her that she does not need to worry about me turning gay or feeling wierd towards me. I need help bad. I want to help her to understand. But as a crossdresser myself and as many crossdresser’s i can not explain to her why i do it. If you could be of some help i would greatly appriciate it.
    Than you.

  6. JENNIFER says:

    I been a life long cross dresser since i was about 5 to 10 years of age , and i am now 55.I still do not understand my need to dress as a girl.I feel strongly i was born in the wrong sex.I feel more at ease while dress as a girl.I do most of the time have my own fantasys of having sex as a girl with a man ( either my husband or boyfriend and at times have rape sexual attacks fantasys as well ).I think i dress as a girl because it helps me feel at ease and gives me the chance to think about in my dream world or fantasy of having sex as a girl/woman.

  7. Rachel says:

    This is nothing new, but I crossdress becuase it is comfortable and relaxing. Mainly, I just like women’s clothes better. I love femininity and want to be as feminine as possible (in some regards, but I also like being a man sometimes). I don’t necessarily want to “pass” — usually. I just want to wear the pretty dress and relax.

    For me, sometimes there is a sexual aspect to it. I love wearing panties or lingerie to bed with my wife (a rarity). It just makes everything that much more fun. I love having an orgasm while dressed up and pretty as well. This is not the main reason at all though, it is more of an added bonus.

  8. Vanessa Law says:

    Rachel, thanks for sharing love. Great to hear from you.

    Hugs,
    Vanessa

  9. Theresa says:

    I think in the same way that you do. I have crosssdressed since I was 10, I’m 38 now and I’m not really passable as a woman without a great deal of effort. For the most part I crossdress because i like womens clothes better. I am not into makeup and wigs and don’t see it ever being a real issue. Although there is a sexual or more a sensuous side of crossdressing, I think that there are many of us who use it as an escape from our very regular everyday lives. I love womens lingerie and especially shoes. However I also like being a man. I do manly things for work and also as hobbies. But there is a great release in coming home and shaving my legs and slipping into a nice pair of pantyhose, a silky nightgown and a pair of high heels. Not all of us want to be a woman full time nor we want to have sex with men. This is a very popular misconception that many people have and as result, crossdressers unlike many gay or lesbian people are even less accepted in society. Recently I have been able to have my wife accept my crossdressing as a part of me and she is incredibly supportive. But she also knows that it is MY preference to keep it quiet. I have told many of my female friends that I have done drag shows as a way to test the waters, and much to my surprise they think its great. At any rate I hope that my small contribution to this post reaches someone somewhere.

  10. eve says:

    remember who the first crossdresser was? adam he wore one of eves big leafs

  11. Eric Whitney says:

    I recently wrote about a crossdressing client on my blog. Actually, he just liked to wear a nightgown in bed. I think he also found the outward expression of his femininity very relaxing.

    http://wp.me/sK78O-lanz

  12. msC says:

    I just discovered my boyfriends basket of goodies and at first I freaked out because I knew for some time he was hiding something from me. I told him that I want to join in on whatever it is. Now I know and I can accept this but I want to understand the need to dress up and fantasize, would you men be willing to talk and share these fantasies with your wife if she was open and non judgemental about it?
    How do I approach this with him without him freaking out?

  13. Kaydi says:

    Hallelujah! I needed this-you’re my svioar.

  14. kuchel says:

    HI
    I am in the same boat you are in. I tried to explain to her, and she wont budge. The problem is there is no point in arguing whose mind is closed or not in a rational state. It is quite difficult to argue with them, I guess next to impossible.

  15. cntlvr4u says:

    I personally would love to converse with an understanding woman on this subject. I have told my wife and she is aware of my panty fetsih, but is NOT willing to open her mind or even try to understand any of it. She has actually gone so far as to forbid me to do it. Yes, I would love to be able to be open and honest with my wife, unfortunately this is not the case. I truly believe our relationship would be strenghtened by having her approval and support.

    Maybe you could slowly incorporate it into your lovemaking by asking him to wear your dirty panties while you have sex. Maybe even suggest a girls night in where you offer to paint his nails and give him bubble bath.

    If you would like to converse directly, my email is cntlvr4u@hotmail.com

  16. Ty says:

    I’m a straight guy who crossdresses in private. The reason I do it it’s a turn on. It’s a role play thing. The problem with sharing it is that he might be afraid you’ll tell people. I would wait until you guys are having sex and I’d put your panties on him. Turn it intoa kinky thing. Rub him through the panties. Maybe put a double ended dildo in youand wear his underwear. Make him rub your dildo through the underwear. This is how it hapenned for me. It’s a way to get involved and have fun too.

  17. Christina says:

    Bring up the subject of crossdressing during conversation and see how he reacts. Act like you have an open curiosity and he will eventually open up, because it is what I would want if I were him.

  18. Mike (Mikelle) says:

    You could start by asking him if he wants to wear a nightie to bed (you might have to buy him one) or lay his stuff out on the bed one evening and just ask him if he would wear it in front of you

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