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?



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 it can be. I always had short hair, usually only 2-3 inches long, I preferred it that way but always sort of felt I didn’t look girlie enough compared to my peers. I remember during my eight grade graduation when I wore a floor length gown, I just felt akward like a guy in a dress.
It wasn’t until the end of highschool that I actually wore a pair of high heels. Sure, I wore shoes that happened to have a heel, but these were sexy, strappy, black, stiletto heels that belonged to my sister and I was used to wearing doc martens. I was just trying them on with a skirt I owned but never wore and it was such an unexpectedly exciting moment. My legs looked long and sexy, my ass looked hot, I couldn’t walk in them but I still felt like the sexiest girl in the world. It felt euphoric and I suddenly knew what the fuss was about. I felt comfortable in women’s clothes and wearing them really boosted my confidence in myself.
I imagine for men, crossdressing is a lot of the same exciting feelings. Let’s face it, being girlie can be a great amount of fun! It can make you feel desirable and confident and delicate all at once.
I think society’s stance on gender roles is antiquated to say the least. Obviously, things can never be so black and white or should I say, blue and pink. “Male” and “female” characteristics shouldn’t have to be mutually exclusive. It breaks my heart when something so harmless is so misunderstood and vilified on the basis that it isn’t “normal”. From what I understand, “being normal” seems pretty boring and restrictive to me and I don’t want any part in it.
The fact that so many crossdressers live in shame or in fear that someone will find out about their secret is heartbreaking to me. I sincerely hope that they can make peace with themselves, and that maybe one day society will follow suit.
Stay strong, boys and girls.
Jo, thanks for sharing – I’d never though of it like that. It’s wonderful to hear this from your perspective as a women, who grew to love feminine clothes.
I can definitely vouch for my experience the thrill of looking good, feeling desirable and confident when wearing women’s clothes. If I take it as a purely intellectual exercise it’s somewhat absurd to think that it would be the case, but my experience and emotions tell me otherwise.
Thanks again for your support Jo – I hope to see you around crossdresser heaven again.
Hugs,
Vanessa
Sophie, it’s wonderful that you are strong enough to be who you are. The most important thing is to be true to yourself, even when others have different expectations on you.
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 emotionally as well as spiritually.
I’ve always said…”If it makes you feel good and doesn’t hurt anyone else….what’s wrong with it?”
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 work out in my yard, front and back, in skirts and dresses. Every other week I cut the grass in my skirt or dress. The neighbors have seen me like this and have gotten use to it. They have come over to talk to me about other things while I am in my skirt or dress and they have not said anything. I even had one young woman selling steaks try to get me to buy some while I was outside in a dress. She did not say anything about my dress nor did she appear uncomfortable about it.
I did one time late at night go to the post office and purchased stamps while wearing a short denim skirt. Other customers in line did not say anything. I also purchased gas for my car while I was out and had to go inside to pay cash for it. The clerk and another person inside did not say anything.
Only if “everyone” starts going out in public in a skirt or dress will it become acceptable. It just takes being able to take criticism. I hope to get up more courage soon and go to the grocery store in my dress or skirt.
Being a single male living alone makes doing these things easy for me.
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 that I was buying for me and not wife! Just do as you please!
Kayla, that’s an interesting observation, that perhaps the more feminine side brings the whole being into better balance. You need to be careful who you ask your question to though, since I can imagine certain folks who would find something wrong with it
Here’s hoping that society evolves past this prejudice as well.
William – I agree, the Internet has been a fantastic thing for the transgendered, and I deeply appreciate all the ladies online who have shared their stories. When you’re alone and uncertain about what is happening inside you it’s scary. With others we have a chance to realize that we’re part of a community.
I see it as a tremendously positive thing that the next generation would have grown up on the Internet, and largely with less fear expressing themselves (if the videos I’ve seen on youtube are any indication
)
Those moments when we can be who we are and be accepted are heaven, aren’t they?
I agree with you – if more of us started going out in public acceptance would come sooner. I wrote about this a few months back (http://www.crossdresserheaven.com/a-call-to-crossdressing-action-its-not-just-the-transgendered-who-suffer/) – let me know what you think.
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 and more as time goes on and now i raelize that i need more fem timethan i would have ever realized i would luv all cds and wish we all did not hide so much and came out to support and play with each other
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 when the wife is home sometimes when she is not. I like to feel comfortable yet have some firm fabrics to hold in my midsection.
This year I intend to try some wigs. I always wanted to have long curly hair. I am looking at a wig catalog currently to try and see what I might choose. It is very nice to find a space to discuss these things with others.
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 I realized it was something I want to try. He sent me his picture and told me to get back when get my new look together. I feel excited by this and feel like I can start a new life even though I’m 60. I’m trying to find anyone who can give me advise. I’m shaving off the hair on my face before going to bed.
Maria, thanks for sharing your comment – I can whole heartedly recommend crossdressing (though I’m a bit biased
). Growing up in a less tolerant time, you’re probably already used to the social cost of being different, which is the one caution I would give someone who was considering crossdressing as a choice.
Take a look around Crossdresser Heaven, I’ve got tips on everything from dressing to makeup to feminine deportment. Let me know if there are other areas you’d be interested in hearing more about.
Best wishes,
Vanessa
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 in their brains. Their brains are hard-wired to release dopamine and other neurotransmitters when they feminize themselves. These neurotransmitters are powerful chemicals. They produce sensations of well-being, pleasure, sexual gratification, and self-identity. They affect the reward centers of the brain and thus mimic the addiction response. These men feel as if they NEED to crossdress.
Their crossdressing may begin as a small child who admire girls and feminine things. They may believe that girls have it better in life than boys. Their early crossdressing may be an attempt to pretend to live as their idols. Most crossdressers have their first experience during puberty. Their hormones are just beginning to flow, and their experience is very memorable. They may get an immediate errection, the may get goosebumps, and their body may quiver. It’s like, WOW!! What was that!
In youth, crossdressing may be closely associated with sex and masturbation. As the crossdresser ages, it gets harder to generate the same stimulus. He may still find comfort and relief from stress by crossdressing. He may work harder at creating a female alter-ego. It’s all part of an effort to increase the release of neurotransmitters.
Here is a simple experiment to determine the association of self-feminization with neurotransmitters. Dress up in your favorite feminine clothes. How do you feel? Wonderful? Good. Now masturbate. When you masturbate your brain releases a rush of neurotransmitters followed by a depletion of them. Immediately following your masturbation how do you feel about your feminine clothes? Most will admit they feel disgust with their crossdressing (for a few minutes). At this point these men are experiencing the same sensation to self-feminization as the other 90%.
Crossdressing is neither good nor bad. However, since it mimics the addiction response you need to keep things under control. If you do not control it, it will control you.
DocChuck, that’s awesome! You are truly blessed to find such a special woman.
Would your wife be willing to go to a beauty store with you to try on the wigs? That could be a fun, bonding experience for you girls.
Hugs,
Vanessa
nervous
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, that while I do get excited wearing womens kimonos, I actually feel much more comfortable and enjoy wearing mens kimonos better. A kimono is no boring ordinary thing. It takes a lot of time to put on (and take off
feels great, and really makes you stand out. A mans kimono makes me feel confident and really seems to give me peace. They are still worn today in Japan, and it is an accepted attire. It might be something that others can look into. It might help. Or at least help you figure out some of your own feelings too. When both my girlfriend and I are wearing kimonos it is some of the most enjoyable times I ever have.
Rain, that’s an interesting observation – perhaps for some people it’s not so much about the clothes being of the opposite gender, but the quality and extraordinarity (if that’s a word) of the clothing. Boring, dull and scratchy is difficult to fall in love with. Sensuous, silky flowing gowns stand out and make you feel good – even if they’re traditionally men’s clothing.
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.
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 like/not like having sex with a different person, too, and I enjoy that as well. Now I’m not sure I’d ever want to have another boyfriend who DOESN’T crossdress.
@Charity: Wonderful to hear from you love! My heart soars when I hear from women like yourself who have not only accepted their husband’s/boyfriend’s crossdressing, but rejoice in it. I think at times as crossdressers we find it so difficult to accept ourselves that the thought of another loving us not just in spite of this, but in some way because of it, is a powerful message!
@Chloe: Hon, I’m so happy to hear that you’ve found such a special person in your life who loves you for who you are!
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 to me and gets me really aroused. But, it’s more than that. Most importantly is that the props of womens clothes and shoes help me get closer into the spirit of the sexy women I love so much. So I feel the the cross dressing helps me be more complete of a man, not less.
Hi Will, so true – it’s hard to define, and can’t be captured by just a sexual feeling.
Tina – great advice! Do as you please, and be confident while you’re doing it.
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.. I enjoy being in as much women’s clothing as I can to the comfort I fell when I am out doing things guy or girl… I want to pass more readily because shopping is easier but 24/7 I haven’t comes to terms with yet.. Another battle and another time… But I dress to be me!!!!! Does it matter how I look or what my sexual orientation is? I enjoy me that is all that matters.. After that is is society that leaves me stranded.. Luv Janet