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.

EnFemme

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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Chloe
Chloe
15 years ago

My soon-to-be-ex-wife knew about my cross dressing, & barely tolerated it. I don’t pretend to understand it myself, so why should I expect anyone else too? I’m just much happier as a woman. I don’t hate being a man, I just need to be girly sometimes. I always thought “if I could only find a woman that liked my crossdressing, I’d be happy" Well now I have! I’ve found the perfect girl friend. It just does not get any better than playing dress up with her. We have such a great time together. Sometimes I’m a man, sometimes I’m a… Read more »

Kevin
Kevin
15 years ago

why do I crossdress? I crossdress because I like the feeling of womens clothing on my body, it makes me feel so sexy. I feel like the women’s body is the most beautiful thing in the world. I have never told my family of my fantasies of being dressed up all sexy like a women. My wife would surely not understand. I have a girlfriend though that understands fully. When we are together she even helps me dress up by applying my makeup and helping me find the right things to wear so that I look good in my outfits… Read more »

Kenneth Brix
Kenneth Brix
15 years ago

Kevin said he likes to cross dress because “I have a feminine side…"

I like his answer and I think it is the main reason I like to do it as well. Most—if not all of us men—are part female, and to dress that way (at least occasionally) seems entirely natural to me.

And by the way, Deuteronomy 22:5, when properly translated, does NOT prohibit cross dressing, a fact I recently learned which causes me to love God more than ever!

Raechel
Raechel
15 years ago

I dress because I love fine clothes and the highest of heels. I feel wonderful while wearing skirts and heels. I’ve shopped as a man for womens clothes and find most sales people are not too concerned. Some are just wonderful. I found the most wonderful shoe boutique about a year ago and it’s my second home. The sales staff (my girls) are the sweetest things in the world. They have been so nice and accepting of me. I really think I’ve made an impact with them too. The more folks we show who we are and the more people… Read more »

Patrice
Patrice
15 years ago

I feel so relaxed when I dress as a woman. The feeling of pretty lingerie under a dress or skirt and blouse combo is unbelievable. I feel less stressed and can really relate to my feminine side. A woman is so lucky to be able to wear such pretty things, from undies to their outermost garments. I love wearing makeup and a pretty wig. Heels and stockings ( I prefer control tops over garter and stockings) are tremendous. Nothing like smooth sexy legs. I am completely hairless on my body with exception of one place. I practice being a woman… Read more »

crystina
crystina
15 years ago
Reply to  Vanessa Law

to me crossdressing is more than just wearing the cloths and makeup. most of my life (and still going) i have felt that i am more like a stage actor playing a part. i play the part of the all american boy who played football, dated cheerleaders, and acted agressive. i also play the part of the good son who cares for his parents and is the dependable man everyone can turn to in need. but when i dress even if it is only a little makeup for 5 minutes to have a quick smoke i feel as if i… Read more »

Daniel
Daniel
15 years ago

Honestly, I personally cross dress because I try to ignore sex and gender boundaries in life. Dresses, skirts and (for reasons I can’t explain) high heels feel very loose and comfortable to me, certainly much more so than suits, so I wear them whenever I can (not very often, since I’m still a minor and my parents disapprove…) I also wear other general women’s clothing, like pants and shirts. To answer the question more concisely, I cross dress because some pieces of women’s clothing are just really awesome, and I would wear them if they were men’s clothing instead. I… Read more »

Daniel
Daniel
15 years ago

Thank you! I’m not entirely sure what your question is asking, but of the gender of clothing switched (that is, currently male clothing people female clothing, and vice versa), I would wear both types of clothing, although then I would tend toward wearing the (newly) male clothing more often, again because my parents push for male clothing. Although honestly, I must say that I like currently female clothing better than currently male clothing, on average. It tends to be much more comfortable and colorful.

Daniel
Daniel
15 years ago
Reply to  Daniel

Sorry, in my second sentence I accidentally typed ‘people’ instead of ‘became’. No idea why… The parenthetical should read “(that is, currently male clothing became female clothing, and vice versa)". My mistake

Patrice
Patrice
15 years ago

Great thoughts, Daniel. I wish you well as you start out towards womanhood. You will find each day more exciting than the next. As you mentioned, female clothes are so much prettier and more colorful. Pretty styles, heels, makeup, lingerie – oh, how we love these. I’ve been “dressing" for more years than I want to remember. One thing I’m sure of, Daniel, is that I completely love and adore dressing as a girl. I wish you well as you take “your first steps in your pretty heels, stockings, etc". You will love, and wish you were, a real girl.… Read more »

Leon Martinez
Leon Martinez
15 years ago

rather than to ask yourself why men dress this way i would ask you to think more logically rather than emotionally. because as a man i have found the truth and that is that, what have women faught for in the past in regard to jobs social factors. the first instance was for political conquest in regard to being able to vote, this was only for men to a new PM. Also you now have the opportunity to get paid the same as a man, you also have the oppotunity to wear MANLY Garments from past generations and call it… Read more »

Patrice
Patrice
15 years ago

I crossdress because I feel female most of the time. I feel so comfortable putting on a pretty bra and nice pair of panties. I love wearing my control tops over the panties. My toenails are painted 90 % of the time. Of course, my legs, and most other body hair is gone. I usually use a hair remover for my chest, or on places wear I can’t shave. My figure is feminine. After I put on a dress or skirt/blouse combo, I’m starting to feel like a woman. I love to do my makeup, from eyeliner, mascara, rouge, lipstick,… Read more »

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