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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Jon
Jon
15 years ago

For me it has to do with self-expression. Society defines certain expected social roles (also called gender roles) based specifically on whether someone has XX or XY. Some aspects of myself fit within the XY category that society claims is required of me, and some aspects of myself lie in the category marked only for those with XX. For so long of my life, I was refused to express those parts of me that are reserved for those with XX, so now it is so awesome to get a chance to dress in way that is complementary with my inner… Read more »

PHIL
PHIL
15 years ago

hi i came home as a new born in a dress .my oldest sister dressed me like this every day (mom and dad worked alot)at the age of three my ears hed ear rings in them as i got older this was just a normal thing then came the panthose and heels and makeup this was about 1968 yes i have a wife and 2 kids and 7 grandkids witch i love them all very much. but most people dont under stand this at all but as you can see i was raised this way and i like how i… Read more »

Erica
Erica
15 years ago
Reply to  Vanessa Law

I have dressed since I was 11 (17 years now). My wife and I were discussing this last night, and I have really no idea as to why the desire to dress as a woman is a part of who I am.

Someone mentioned genetics, and I believe from my own research into alcoholism and depression that cross dressing might be linked to both of these. In some ways for me dressing is like an addiction. This is sensible as I have multiple family members who are/have been alcoholic. Just a thought.

Erica

Zeljka
Zeljka
15 years ago
Reply to  PHIL

I cross dress since the 10 years of age, I have dressed my sisters’ pantyhose, my mother’s OBG with nylons of all colors, but my favorite was gray, skin, black and coffee. Then one summer holidays I was at a house of our family friends on the coast when a lady wanted to undress and I have had to put a blanket over my head, but of course I snicked “out" for a second and what I have seen – I have NEVER and will never forget: a beautiful strong woman dressed in black bra size E, black open bottom… Read more »

chris(aka sophie)
chris(aka sophie)
15 years ago
Reply to  PHIL

i like crossdressing me and my best friend both do crossdressing and love it he borrows his mums clothes and i borrow both of my mums clothes and they are proud of me crossdressing and really wanted me to be gay but i like women iand i always feel like i am one so me, my best friend, and my mums all go on a girls night out (they do our make up and buy our clothes though) the last noght i did was going to a crossdressers club in maidstone in kent its was really fun and thats where… Read more »

Jo
Jo
15 years ago

I should point out that I’m female, but the reasons why men crossdress has never been too complicated or hard to understand for me. When I was a young child, I remember wanting to be a boy. I felt I related more with that gender in just about every way. I used to put socks in my shorts lol. I was a serious tomboy until about 6th or 7th grade when I started going through puberty. I still liked mostly male-centric things including heavy metal/punk music but this is about the time where I discovered makeup and how much fun… Read more »

'kayla'
15 years ago

I never really delved into why I enjoy getting dressed up and in touch with my softer and more feminine side until finding this site. I suppose it has a lot to do with the fact that in my everyday world,I am the aggressor and a ‘take-charge’ type guy. When I need a good balance and to destress….I will open up the two suitcases that allows me to relax and luxuriate in satin and silks. I also tend to become much more submissive when dressing and this is why I truly believe my crossdressing really balances out my persona both… Read more »

William
William
15 years ago
Reply to  'kayla'

Why do men cross dress? Why do people smoke? Why do people sky dive? Why do people …? We do what is pleasing and feels good to us. As has been repeated over and over again, females can wear masculine clothes and nobody bats an eye. But for a male to wear female clothes and he is ridiculed. But there is hope that this may change in a few years. Men can wear ear rings now in public without shame. Also with the internet, this is getting more publicity and more men are wearing female clothes in public. I myself… Read more »

TinaTVee™
TinaTVee™
15 years ago
Reply to  'kayla'

G’day, I have been dressing up since 4yrs of age, playing dress up’s with the girls across the road. 39 yrs later, I now wear lingerie everyday, and sleep in stockings or pantihose, with a nightie or babydoll. The wife does’nt like it but she no longer gets cranky. I too just feel more comfortable, when wearing womens clothes, although I sometimes paint my face as it were, that does not really matter. I buy all my own stuff, and always have, with never a problem, although a couple of salesgirls have blushed quite a bit when they finally twigged… Read more »

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penny
15 years ago

hi all i have been crosdressing since i was about 12 yo am 50 now i was at a halloween party lost at a parlore game and had to don the clothing of oppositte sex. i was dressed totally from panties nylons garterbelrt reel frilly full petty cat and skirt.very nice stuffed bra and sweeter way too much make up also . well the reaction of all the boys and girls made me feel kind of strange in many ways . but i was and am completely addicted to dressing since that evening and always have found ways to dress… Read more »

DocChuck
DocChuck
15 years ago

I have been donning women’s clothing since I was a young man. I was lucky enough to find a woman who embraced my fetish and she allows me to endulge reguarly. I like the sturdier of undergarments. Full corsets with garters. I do have to say finding shoes I can walk in has been a real task. At my age, 67, I can hardly wear platform heels. I like the more comfortable shorter heel that has a peep toe. I enjoy painting my nails and wearing light cosmetics. I continue to dress in the privacy of my own home. Sometimes… Read more »

Maria Jackson
Maria Jackson
15 years ago
Reply to  DocChuck

I am a gay man and I am 60 years old and considering getting into cross dressing. It’s an idea I have thought of many times but never seriously considered until I met a guy online a few hours ago who told me about his desire to meet a cross dresser and how he wanted another guy to play the female role. I told him about my having a mustache and he said he couldn’t handle that. When I offered to shave it off for him he told me more about being a “gurl" as he referred to it and… Read more »

Valerie
Valerie
15 years ago
Reply to  Maria Jackson

Why do men crossdress? Well their brains are hard-wired for it. About 50% of males will dress in women’s clothes some time in their life. They will do it as a joke, to amuse others and have a laugh. They will not feel any emotional connection with the event. If you are in a war and capture some prisoners and make them wear feminine clothes, it will considered torture, and the world will be shocked. However, about 10% of normal, healthy, heterosexual men will say the whole idea is wonderfully pleasurable. What is doing on with those men? Well, its… Read more »

fayyee
fayyee
15 years ago
Reply to  Vanessa Law

nervous

Rain
Rain
15 years ago
Reply to  fayyee

I just wanted to say something along the lines of what Jo mentioned. I am a male, and cross dress, for what reasons I do not know. After reading what Jo mentioned though, I felt like she might be on to something. I thought about some things that help me, and about the way society is today. Well, I live in Japan, and the society was different here back in the past. The typical clothes in Japan were not much different for women and men. Long flowing silk dresses. I own both womens and mens kimonos, and have to say,… Read more »

vasanth
vasanth
15 years ago
Reply to  Rain

I am cd from my 15 years… iam unhappy to be a men.so i like to be women,so i wear sarees,chudis and i want to become a women.please help me.

Charity
Charity
15 years ago
Reply to  vasanth

Another very happy girlfriend of a CD here. I loved dressing up and girly things like doing our nails and hair with my female friends when I was younger, and doing this with my boyfriend now brings back pleasant memories. It’s still just as much fun. I love buying clothes, especially sexy panties, for him. Part of the fun in that is that he can wear much smaller sizes than I can, those sexy clothes for smaller-sized women, and I think I live vicariously through him a bit in that way. Having sex with him is a strange mixture of… Read more »

Will
Will
15 years ago

I’m a 45 year old outdoorsy male in Idaho and Wyoming and I’ve crossdressed since I was about 9 or 10 when I found a pair of high heels in the garage that was going to be donated. Shoes are main thing but I also wear other things that enhance them: nail polish, pantyhose, toe rings, leather pants, skirts, most anything except wigs and makeup. I love women and have never been gay. It’s just the feeling I get when I wear womens clothes and shoes (gotta have the shoes – heels, boots, clogs, or sandals) Yes, it’s so fun… Read more »

Janet
Janet
15 years ago
Reply to  Vanessa Law

So we ask why do we crossdress..? It is a question more of being who we are. I do because I fell right. I fell normal and natural. Do I like the guy in me most of the time. But do I like the girl in me, the one who has the eye for color and what looks good and casual. Yes!!!! But do I sexually enjoy it, No not to what you would consider sexual as per societies limited perception on gender and the roles we play.. I don’t get off on the clothes I live for my clothes..… Read more »

Justina
Justina
15 years ago

I have been crossdressing since I was 12. I 1st got the urge to do it when I was watching a spanish movie with my parents where this guy put on his wifes panties on accident. Seeing that made something in my brain trigger. It seemed so naughty to me and the panties looked so pretty I jus had to try it! I have 3 sisters so it was easy for me to get a hold of some nice underwear. It was a pretty pair of pink bikini cut panties with a heart on the ass that said “cute” on… Read more »

Sam Davey
Sam Davey
14 years ago
Reply to  Vanessa Law

firstly I would like to say thanks to everyone that has posted on this thread as it is comforting to think that I am not ‘alone’ in this world. I first began to dress when I was 12 or 13. I am now 37 and have been married for 8 years. My wife does not know and I do not think that she would be very supportive. I have tried to talk to her about it discreetly but I sensed that she sees the traditional male and female roles are necessary in the relationship for it to work and adding… Read more »

not understanding
not understanding
14 years ago
Reply to  Sam Davey

My dad is a crossdresser and even though I love him I do not understand why he would do this… I am open to people choosing whatever life style suits them but can you please help me understand if you know you like to wear womens clothes why not choose a lifestyle that is suitable to your needs. Why would you involve a woman that wants to have a normal life and kids? Even though you say you feel alone, have you all of you felt what this might to a family or to the children of that family? I… Read more »

NoOne
NoOne
14 years ago

I agree that it is completely selfish to not tell someone that you’re a cross-dresser before getting married, or even engaged. In my mind, how can they know me if I’m hiding a major or even minor part of my life. I’ve lost relationships because of this, but I don’t see them as losses, I see them as another chance to find the one that will accept me the way I am.

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