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.

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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?

EnFemme

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Blake
Blake
11 years ago

Well,…..uhm…..what can say…

Emily
Emily
11 years ago

First, I want to thank everyone on here for their openness and honesty-I’ve read through almost all the comments and this has been so helpful. Over the past 6 months I’ve noticed my boyfriend of almost 2 years wearing women’s panties and panty hose, thigh highs, etc. The first time I discovered it I had done laundry and was putting stuff away in his underwear drawer. My first inclination was not that he was wearing the thongs I saw, but rather that they belonged to another women. Once I figured out they were in fact his, I was actually relieved… Read more »

Cheryl
Cheryl
11 years ago
Reply to  Emily

It is really hard to give acvise on such a situation Emily. I think most would say let him come to you when he is ready. On the other hand he does need to know how much you love him even though he is dressing. You obviously don’t know if he is a crossdresser or transexual. Not really does need to be discussed. One suggestion is to take the items of clothing that you found and put them in the front room with a note that says I don’t love you any less. I have found that an open line… Read more »

dorthy
dorthy
11 years ago
Reply to  Emily

thanks for being suportive as hard as it is to wait if u still want to be with him think about shopping with him for girls closes that will be an enjoyment for both next time in a store take him there and hold it up to him and ask how u like it find one in his sixe that should break the ice

Blake
Blake
11 years ago

Well Emily,here is my view on this.Im a guy.I think why alot of guys like to wear female clothing is because well,….we all started out as a female,and i think some of the female brain chemistry is left behind a little.Im not a doc,but its logical to me.And if you read some of the things ive said here then cool.What i would do sometime Emily,when the both of you go shopping,go to a mall.Tell him you want to stop in at Victoria’s Secrets for a minute.He will more than happy to go there with you.(just a FYI,he can get a… Read more »

Blake
Blake
11 years ago

Just one quick note i forgot,when i hear the word “crossdressers"
it sounds a big degrading to me…dress as you feel people !

todd' class='avatar avatar-64 photo' height='64' width='64' />
todd
11 years ago

WOW ok i did it kind of anyway lol my GF and i went for a ride in the car to make a house payment and i was dressed for the first time outside the house and then the next day i was in the back yard in a skirt… sure felt good on the legs the wind blowing and all i felt free for the first time in a long time but still was worried id be seen by neighbors… but for the short time i was outside i felt soooo good… now i have a problem tho….i want… Read more »

todd' class='avatar avatar-64 photo' height='64' width='64' />
todd
11 years ago
Reply to  Vanessa Law

ty very much for this site as it has helped me answer so many inner questions i have had about myself for as long as i can remember … i wish i would found this place sooner… (wish i had looked)

Blake
Blake
11 years ago

Todd,just wear you skirt and carry on with life as normal as if you were in shorts or jeans.Just do it.99% of females like to see a guy in a skirt.Just last week i had a 14 yr old school girl told me “I really like you outfit" i then said THX

Mellisa
Mellisa
11 years ago

So I typed “Why Do I Cross dress" into google and POOF I was here. Although the article was a good warm up the comments have been terrific for me! Thank you so much! My story begins like most others. I am 35 years old, love woman, and enjoy toys. I started cross dressing around 10 years old when I would visit my grandmother for the summers, However it started with make up. Grandma was a make up queen, tons of it so I played with it before i would shower. One time she had a pair of stockings hanging… Read more »

Cheryl
Cheryl
11 years ago
Reply to  Mellisa

You are most welcome Mellisa. I am glad that you found something in my words that was helpful.

Hugs Cheryl

Blake
Blake
11 years ago

Hello again to all, I really think we should be asking THIS question instead > “Why Do WOMEN Cross dress" ? Because look what alot of them wear and styles that are after mens. For example…Boy shorts undies for women with a fly were modeled after what gender ?………..oh yea,…MALE.I see alot of females wearing guy jeans and dress shirt,or his sport coat,you name it.So then why cant a male do what the females do in reverse ? It goes to show ya that the equal rights movement was only for women,the men were not included,female actually have more rights… Read more »

Larry
Larry
11 years ago

Emily: Speaking from the guys point of view, When my wife found out she was totally supportive. What she did do was took me into the bedroom and put on her own lingerie. She then took out an oufit that she wantedme to wear. She told me that she found me totally sexy in it and wanted to see me in it more often. By doing this and accepting me for it, she alleviated all my fears. She knows I am still a Man but I enjoy the feel and comfort of womens lingerie. We have an incedible sex life… Read more »

Scarlet
Scarlet
11 years ago

I think the idea of clothes itself should reflect a strict catalog of male and female’s belongings is totally wrong. Think about a world with all the garments together with no catalogues, no sexual reference, no fashion preferences, then, the word " cross dressing" just suddenly disappeared. I like the idea of male and female should wear something different, but not strict necessarilly in need. I was born as the only son of my family. When I was 8 or something, I had a fresh idea, “Well, being boys for quite a while, seems like not very dramatic for me… Read more »

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