Why some men enjoy dressing up as woman is a bit of a mystery (besides of having a good time, of course, wink*). The root of the question is “why some men love to cross dress?” and while the case can be said for many other things in life, like “why do some get turned on by whips?” “Others with mummification?” “Or why people love chocolate… well, scratch that, chocolate is a universal item that unites all of us a humans, wink*, thing is, like many other things some people enjoy and others not, it has to do with the brain and with each individual. But cross dressers have been a fixture of research for a long time and they have several theories as to why men cross dress. I found it interesting and thought I would share them in case you were curious; now, after some experience and discussing, most men have told be that one is not exclusive to the other and most of the time is a combination of these common reasons.
The first reason is maybe the most obvious one (hello captain, wink*): Arousal and fetishism. Those are probably the first reasons why men cross dress, since they love the feminine clothing. Sometimes is the visual appeal of lingerie, corsets and heels. Sometimes is how these items feel. Others enjoy the process of looking like a woman; the preparation it takes to get there. The thing is, most of the times dressing up as a woman will lead to some form of sexual release; whether that is masturbation, sex with a woman or with a man. Sometimes a heterosexual man will want to have vaginal sex with their partner, but others will prefer to be penetrated or fantasize about being with another man.
Most men will turn to cross dressing because of the society (another blame on it, wink*). Society tends to view some behaviors as “masculine” and others as “feminine”; for example, if a man wants to be more passive, gentle and sensitive, chances are he will turn to cross dressing as an outlet just because these manners are considered “womanly acts”. In that same vein, other men will also dress to be more flirtatious, to feel beautiful and glamorous.
Just as well, some cross dressers will turn to it when they are going through a lot of pressure in their lives. Dressing as a woman will allow them to step out of that tension and masculine pressure, kind of like a refuge.
For some cross dressers, the thrill comes with fooling the world and that is why they enjoy crossing dress in public; think about it like a secret you only know and how thrilling that can be. If you can pass as a woman, the deception or masquerade is successful, so basically a pat in the back is needed.
The whole process of getting dressed and preparing everything is enough for some men; the skills required to pass as a woman are certainly not as easy as they look (as any woman can tell you, ha ha). Finding the right clothes, properly applying make up and how to act are an art form.
Now, there are some theories that hold the hypothesis that both men and woman are androgynous (having characteristics of both genders, for those who don’t remember biology lessons, wink*). That theory says culture and society are the ones who make men become men and women become women. So, this creates some left over residue of your opposite sex and for some people that burden is so great, they have to express it somehow… and voila! Gender switches are born!
If we are going with that theory, some men even have a very distinct personality when they are dressed as a woman. They can even refer to it as some other person and put a name, just like an alter ego. Instead of saying “I had a great time last night playing with you” it would be something like “_____ had a great time last night playing with you”’. She will probably have a life of his own, with its own personality and all; but the man will always be aware these is something more of an illusion or a fantasy (not a split personality territory!).
On the other hand, some men argue that there’s actually some jealousy towards women and they cross dress to be more like them. Or they just envy a woman’s body. And if you are thinking about transexualism, you are not wrong, because these motives are nearer towards that than just cross-dressing. Although some men also discuss they feel those things but they want to keep their penises, so there’s a very large range here (in case you haven’t noticed it yet, wink*).