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’m in my late 50′s and have had a penchant for wearing women’s clothes srince I was about 8 years old. Several years ago I started wearing women’s underwear and hosiery and don’t wear men’s underwear at all now. My wife accepts this and I think encourages it. One day out shopping in a supermarket a skirt was on the cheapie rail and, on a whim, I asked if I could buy it and she agreed. That started my skirt wearing and I wear them in the house whenever I can. I bought many different skirts off ebay. My wife is quite understanding but even she sometimes accuses me of being gay (I’m not) or wanting to be a woman (I don’t). I think that she has misunderstood my needs because she encouraged me to nuy all things feminine including make-up. I don’t mind a little neautral or pale lipstick or nail varnish but that’s as far as it goes. I don’t want to wear dresses or frilly blouses or such. I like wearing skirts because they are soooooo comfortable especially in hot weather and I wish that I could get others to see this and accept it. I don’t really know why I am like I am but I am comfortable with it. My latest is that I would like to have a go at making my own skirts. As I don’t sleep a lot sometimes I go for a walk wearing a skirt in the early hours of the morning and it’s so relaxing.
Hello, My boyfriend enjoys dressing as a woman in skirts and dresses and has lots of high-heeled shoes that he’ll wear around the house a lot. He says he likes the freedom that skirts provide with or without a thong. He wears make-up when he dresses as a woman and I must say he applies very well. This is a new world for me. Going out in public with him as a woman is quite challenging for me. I love the man that he is and I don’t want to lose sight of that part of him but I do have to say that I enjoy this feminine side of him because he is so sensitive and understanding. I’ve always thought that the best person to understand a woman is another woman. Skirts and dresses are definitely very comfortable in hot weather and I even feel more femininely free around him.
Hi Maria,
You sound a very understanding person,and your boyfriend’s lucky to have you (you’re lucky to have each other).I can see why you don’t want to lose him as a man,and it must be challenging (for both of you) going out.
I hope you find a balance,and keep talking with each other.
Natalie x
You sound like a great person. One would be lucky to be with you.
For whatever reason cross dressing is something new to me. I’ve known that men have and are doing this in the world and like gays and lesbians etc., it is something to learn to accept. You can’t deny who a person is just because it doesn’t feel right to you. I’ve got a ways to go to feeling more comfortable with my b/f cd. When I looked under his bed one day and saw a high-heeled shoe I actually felt relieved when I realized it was probably his shoes moreso than another woman’s. He is sexy as a man but am not sure how comfortable he is when I tell him that. I’ve also told him that he has good taste in dressing as a woman in the clothes he has worn and the make-up that he has applied. He isn’t gawdy at all which I do appreciate and I appreciate his sense of humor when it comes to wearing the high heels around the house for cleaning ceiling fans and other high places. He is a tall guy and I enjoy his sensitiveness to me as a woman. This is interesting to me in that a previous relationship left me feeling less than a woman and I was married to a very manly man. His CD is a whole different world to which I’m trying to live in with him.
I am wondering about my husband. Here are the facts…
1. I found Capri (little cigarettes) twice now after I had been out of town.
2. I was unpacking his overnight bag from a trip that he was on and found a vibrating butt plug.
3. He was out of town recently and had two packages delivered. I opened one to find a womens blouse (from a cross dressing website) and the other I googled the return address and it is also from a crosser dressing website.
4. I have found catalogs that showcase cross-dressing clothing.
My concern is that he is gay (because of the butt plug) but he hides so much. What did I get myself into, I don’t trust him at all.
the cigirette part i dont know nothin but i have used anal toys anything i can get my hands on and i have never been with a woman all the toys a woman would use i have used dildoes butt plugs bannanas cuccumbers anything else that will fit ive used a few other things that might not even been used buy a woman
to jenny,
I had the same feelings and reactions as you when i found the vibrating butt plug too! and at first he was really tryin to come up with some good reasons why it was not his.
this started my is he gay or bi thoughts! and severe trust issues.
even 17 yrs later i still think he has been with a man at least once,although he denies it. and he still hides things on occasion, but i love himand until i have some real good proof of an affair, i just deal with it, its just how he is.
Hopefully the 2 of you can discussthese things, and not get crazy like i did
Hi Jenny,
A man that likes anal stimulation does not mean he is gay. The prostrate is a very sensitive and can supply a fantastic orgasm. I am a straight CD male who enjoys such. Being you found those items i would suggest that you plan a nice evening for him, maybe at a hotel, pick up an out fit for him to wear and have it lying on the bed for him at the hotel, and i would get a strap on for yourself and give him a night to remember. Your relationship might just go to a whole new level of bliss and your concerns would transform into a deeper love with a man that is completely in touch with his feminine side. If i was your man that is what i would love. there is nothing wrong with anal stimulation, its society that has labeled it “Gay” break the chain and have some fun!
To Jenny,
What does crossdressing(which i hate that word description)have to
do with him being gay ? If a woman wears a man suit,is she a lesbian ? Any the other items doesn’t mean a thing,men that are straight and gay male that likes those sensations,like most men are afraid to say or do so.Im not
I love the way my boyfriend treats me and I’m getting more used to his cross dressing around home. He is a special man and we’ve just gotten into the anal stimulation….especially for him. I so much want to make him happy as he does me. CD is new to me and he does have good taste in the clothes he buys. He’s very thin so everything looks good on his slender body. He seems to feel pretty comfortable around me and I want him to continue to feel so.
Hi Everyone. I am not sure all the time what I feel like I am. I am a person who loves to wear skirts around the house but in public I kinda feel nervous because of other people staring and comments from them. I do have on time wear skirts in public because they feel so comfortable and I get the air in all the right places. I just am a person who is not passable women and also gets told I am gay because im in women clothing. No one seems to understand.
I’m getting more used to my boyfriend’s cd. He told me he’s the same person whether he is in women’s clothes or not. That made me feel better. I guess I was relieved to have not lost the man I originally became attracted to.
I’m just going to answer the question at the top of the thread.
How can I make him stop cross dressing?
You probably can’t. I guess you could try an ultimatum. Threatening to leave? Telling all his mates or work people about it. Humiliating may work. Makes me feel pretty crap though when my partner does it. Then she bitches about how sad I am and to get over it.
I would try to accept it and not worry to much about it. There are bigger issues in the world to be honest. Like AIDS, Malaria, Wars and Starvation. Does it really matter your boyfriend/husband likes to slip on a skirt every so often? I suppose you could just leave him if its really so bad.
I dont care that my girlfriend loves to wear guys clothes.
She doesn’t even wear any makeup nor does she style her hair.
She hates it when I dress up. Makes me feel pretty crap about myself.
She says “its not normal”. I have never judged her like she judges me.
Its pretty sexist if you ask me. Kind of borderline discrimination.
I don’t wanna start a huge fight on here but I think its kinda sexist to stop men Xdressing.
I thought in the 21st century people might be able to forget about assigned roles and stereotypes.
I think its sad, makes me sad anyway.
Melody ♥
Hi i`m Alicia i dont know why i cross dress but i been doing since i was ten year old i started with my sister bras and panties i try them and i was hooked i tryed to stop but i cant when i am dressed it seem all my stress go away my girlfriend and daughter know and happy with it i like wearing women clothes more the wearing men women clothes are very sexy i like the ideal of looking pretty and feeling sexy i did go on hormones i do have breast and since the hormones i did get interested in men i not on hormones anymore i still feel the same about men i am Bisexual i am BBW FEEL GOOD TO SPEAK ABOUT IT
To Alicia,
Thats way coool..just being yourself is great.Like the Disney Ch
says “JUST BE YOU” and thats what i tell people when they do ask why im wearing a skirt,but that is a very rare occations.Most of the time they just ask about my tattoo’s.Just yesterday,i was out doing some running around,i was wearing a black and red plaid pleated skirt(3 inches above my knee)and a red tank top,i was heading to my car to go,and this lady,about 50 or so,very cute i might add,and she said to me “That’s a cute skirt” i said “thx” and then she said “more men should wear skirts i think”.So its not really that big of issue for me.
I dont wear jeans anymore,other than to work on my cars of course…..More power to you Alicia and others as well