Why do some men like to crossdress?

This article will shed some light on the often hidden subject of crossdressing!

crossdresser putting on stockingsThe regrettable truth is that there is simply no straightforward, one simple answer to these types of questions. If there was, you probably wouldn’t be coming across this article, and the discussions on this subject would have been settled long ago.[break] In my personal experience, the fascination with woman’s clothing started when I was very young. I must have been about 7 years old, and I remember going to great lengths to get and then put on my mom’s lingerie. My most vibrant recollection is as a teenager, anxiously purchasing pantyhose from a local shop and then wearing them while walking home under my clothes.
I felt and still feel to this present day, a need to wear woman’s clothes almost on a daily basis, and I can’t quite explain where this feeling comes from. Many times I find the feeling hard to control, especially if I go a few days without dressing up.
The media likes to reason that cross dressing is a sexual perversion, and so naturally they see the desire to cross dress, 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. I believe coming across some Hustler and Playboy magazine when I was around 11 only magnified my crossdressing as seeing the sexy woman in the photos wearing lingerie and stockings turned something on inside of me that soon after those experiences I yearned to put on stockings and pantyhose. I remember the feeling my smooth, silky stockings was overwhelming. Although at this time I wasn’t shaving my legs. I recall stealing some of my mom’s pantyhose and cutting them up to make stockings out of them. Then I would use a rubber band to stop nylons from rolling down my legs.
I often would go to sleep wearing my home made stockings and carefully taking them off in the morning under the bed sheets and hiding them in the drawer under my bed before my mom would walk into the room.
why men crossdressMany cross dressers I’ve met over the years, describe the need as ‘feeling more comfortable wearing woman’s clothes’. This is sometimes coupled with the desire to be seen as a woman. To not simply dress like a woman, but behave like one as well, to wear make-up, lingerie, shoes and otherwise pass as a woman. There are others who cross dress for sexual excitement.
Cross-dressing covers a wide spectrum and therefore is hard to really define for any one group.
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 optimistic that as society grows more accepting of diverse gender expression we will see more crossdressers and transgendered stepping forward to share their stories and feel open about discussing cross dressing with family and friends, without the need to justify their behavior, and no longer shamed by everyone.
Even psychiatrists have a difficult time with the issue of cross dressing. They feel that it starts around puberty, but, some male children will experiment dressing up, for example in their sister’s clothing and race around the house and turn out to be full-fledged heterosexual males in years to come.

Psychiatrists don’t seem to know when it starts or really why crossdressing takes place.[break] Cross-dressing is another term for transvestism, and this and trans-sexuality and the association of both with homosexuality are often confused, even by some practicing cross-dressers. A typical transvestite would be a man who appears to be quite normal at all times when he is not cross-dressing. He is not likely to be homosexual, will prefer women as his sex partners and will most certainly not want to lose his penis.

For many transvestites, crossdresing is an intensely sexual activity. Most transvestites have their first cross-dressing experience around puberty or in adolescence. The first experience is likely to be sexually exciting and the young person will carry on with the practice.

In contrast, a typical male transsexual will not identify in any way with his physically normal male body. He believes that he is a woman and is trapped in the body of a man. To him, his penis is a mistake of nature and he will want to get rid of it.
Some men use cross-dressing for the purpose of sexual excitement. It seems that the majority of transvestites are no more likely to go on to trans-sexuality than a social drinker is to alcoholism or an occasional cannabis user to injecting hard drugs. Of course everyone has to start somewhere and there is some evidence to suggest that the longer you cross-dress, the further along the continuum may find yourself moving. I can relate somewhat to this theory as I have discovered over the years that my crossdressing has been evolving from simply putting on stockings and heels to full make up, wigs, clothing and even nails.

After their initial cross dressing experiences, transvestites will progress to one of 3 main groups:

He will stay with the type of garments he first used and have a fetish-like attachment to them.
His initial preferences will expand and he will slowly move on to other clothes and finally into the wish to be dressed completely as a woman and to pretend for periods of time that he is a woman, but he will not want to go beyond pretending and will wish to retain his male personality.
The third group will fringe on trans-sexuality in that they will live and pass as women for extended periods of time. The only real difference between these so-called crossdress“secondary” transsexuals and the full transsexual is that, again, like all the less extreme transvestites, they have no wish to actually be women.
There have always been plenty of men who get a sexual thrill from cross-dressing, but the accepted view of most experts in this field now is that these are not the majority.
Sex, particularly with other people is not the main reason why most men cross-dress and will masturbate because they, themselves, are the ideal woman, and the man no longer has to fear rejection, criticism or disappointment which might come with attempts of intercourse with a woman.
Cross-dressers usually will do this in secret and enjoy when the wife and kids leave the home. They have their day planned! They will even go so far as to shave off body hair, take a hot, perfumed, bubble bath, and dress in something silky.
However, many crossdressers just enjoy the feel of certain materials against their bodies and go no further than to dress as a woman. More and more crossdressers are “coming out of the closet” and if lucky, their wives will accept the way they are as long as they keep it private and away from friends and family.
In my particular case, my girlfriend knows I cross-dress and she has accepted it which I am very appreciative of her for doing so. Outside if my girlfriend, no one knows and this can be psychologically challenging for me at times.
I know some people will mock this and say I need help. I say to you have never walked in my shoes. Judge me if you want, it makes no difference.
Hope this helps you in your journey…


  1. Bobbie  August 7, 2015

    I love to cross dress I wear bras and paint your everday I wish I could be a woman but I am a crossdress

  2. Lacy  August 16, 2015

    Much of what you say here is so true of me as I’ve loved to dress starting at 10 in my mom’s bras and panties. I live my life with a family who knows nothing of my desires of feeling and being a girl and don’t want a to transition fully as love my penis. I find my crossdressing to be very sexually exciting and have done it on and off all my life but it wasn’t till later in life that I ended up dressing and having a date with a man who loved me fem. It was so exciting and had I done it earlier in my life it would have changed everything for we as we had a wonderful time including his taking me to bed and making love to me as a woman he knew I loved to be. Explaining why we feel this way is a mystery to me as when dressed I want to be with a man who loves me fem and please him in anyway I can. But when not dressed I have no interest in men. It’s like Jekyll and Hyde. I don’t question it anymore as it is what it is but just wish I could dress and date more but have put my life into a situation that it’s not possible. Too bad as love being a gurl.


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