Why do some men cross-dress? This is almost as inane a question as why do birds fly? Or why do mammals grow hair? Why does the sun rise in the morning and set at night? Why do humans snore? Why do bees sting? Why do balls bounce? Why do wheels roll? Why is the sky blue?
Why do some men cross-dress?
As with all the other psychological questions, this one has no definite answer. People will cross-dress simply because they feel the need, feel the urge to. Something in the brain tells them that dressing like the opposite gender will make everything better and will make the pain go away. The key, of course, is to delve deeper and find out where that pain is originating in the first place.
Several factors go into causing people to dress like someone completely unlike themselves. Cross-dressers aren't necessarily homosexual, but just people that desire to be the opposite sex. For instance, if a man dresses like a woman, it's because the man no longer wants to be the man, but wants a fresh start, a new existence. Becoming a woman on the outside may convince this man that he is a woman on the inside as well. Of course, this is impossible. Once a man, always a man, but it's the mental aspect of the situation that can convince this of a person.
Low self-esteem can be a major factor. People who cross-dress generally aren't happy with the way their life is going. Recent events may have made matters worse, to the point where they no longer want to be who they were born to be. They'd rather be someone else, take up an entirely different identity altogether. By cross-dressing, they can basically start a whole new life as a whole new person. They can experience everything from a different perspective (that is, the perspective of the opposite gender).
Men who cross-dress do so in an attempt to transform their lives. These are men that generally get little respect from friends, family and co-workers. They may be taunted, teased, mocked, ridiculed, and laughed at for the person they are. And what a shame that is.
I know the feeling. I had some low points in my life that brought two scenarios into my head: killing myself, or becoming somebody else. While there were indeed two times in my life I can remember wanting to seriously kill myself, I never did. Instead, I chose the second option, but went about it in a couple different ways. At first, I simply changed my attitude and my personality. I became someone everyone would love, but in that attempt, it only made people look at me as a stranger trapped in an average man's body.
Since that didn't work, I went out one night, after a long work day, and bought two dresses, a bra, some makeup, and a wig. I went home, put it all on, and transformed myself into a woman. Upon looking in the mirror, I saw my real self come out, or at least what I thought my real self was. I wasn't homosexual, I told myself - just in a state of deep denial and deep pain. I looked at myself, and saw a completely different person. I saw someone that people would like, that people would want to be around. I considered myself beautiful, and so I went out.
I wasn't embarrassed, nor was I ashamed of the way I looked. I felt comfortable with my body. I went to a bar and sat down at a table. I ordered myself a drink, and sat there lonely, waiting for a man to come my way. In a way, it was an experiment of my strength as a man, my endurance as a human being. I wanted to see if my life would be any different under a dress. But, as it turned out, nothing changed. And my feelings of a new-found freedom soon turned into the sad, depressing state I was in earlier that day.
To this day, I never cross-dressed again. I can't say I understand for sure why some men cross-dress. I guess they just want to feel better about themselves. They want to feel wanted, desired, important, and open with themselves and the world. That I can fully understand. Everyone just wants to feel loved. Everyone needs an identity. Everyone needs to feel like they make a difference in the world.
We're all people on the inside, no matter what kind of clothing we wear. The only thing that differentiates us is how we express our being. If it takes cross-dressing to make a man feel better, then who's to question it? If some men need a dress to give them that self-consciousness, then so be it.