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More thoughts on why men, or at least for myself, like to dress as women.

My original thoughts on why I have been attracted to dressing like a female I posted several years ago and is included in the “My Story” portion of my site and is reposted at the bottom of this page. Recently, through examining myself as well as other people I know (not TG) I have developed some more thoughts on it and decided to write about them.

Both of my new thoughts relate to how our society assigns roles and responsibilities and our reactions to those.
Firstly, I think there is a lot of overlap between men and women in their personalities and inclinations. We all know what the stereotypes are…in general, men are more aggressive etc and women are more caring and nurturing. Stereotypes are based on trends and are often true but within those true generalization are individuals that range from filling all of the stereotypes to none of them. Therefore, men can have many characteristics generally recognized as feminine and vice versa.
However, the stereotype is assumed of all, and anyone outside of that is considered odd. Therefore, many people try to suppress those inclinations. Sometimes without further issue, other times suppressing them is exhausting and the individual tries to find a way of expressing those inclinations. A male may see the role and expectations of the two sexes and feel that those of the female seem to fit his personality better. For myself, I find that occasional excursions into the world of femininity are enough. For others, living as the opposite sex seems to be their solution.

Another thing I’ve noticed is the importance of “control” in people’s lives. People need to feel like they have control over their own lives. We are constantly bombarded with rules, laws, requirements, social norms, etc. When people feel like they cannot control their lives within those parameters they look to exercise some freedom of choice outside them. For each person that may be different. One person might chose to steal from an oppressive employer. Another might have an affair when they feel trapped in a bad marriage. The act may not even be related to the situation as a man that feels trapped in his job but happy with his wife might feel more in control of his life by having an affair…etc. Possibly, the source of any “vice” is to exert personal choice by partaking in something that is outside what is acceptable when living inside the parameters of what is deemed acceptable has not been satisfactory for that individual. People get drunk, watch porn, graffiti, gamble, drive recklessly, etc not because the results of those things are productive in any way but because making the choice to act in that way makes the person feel like they have some degree of control over their own choices and actions.

To bring this back to the topic at hand, either through some biological or some personal experience, a portion of men are inclined to enhance their perception of control over their own lives by wearing women’s clothes (or even fully adopting an identity). Wearing feminine clothing is their way to say, “I may chose to play by most of societies rules but I can chose to do my own thing when I want.” I think it might be an overstatement to say that dressing enfemm is like giving society the middle-finger but I you get the idea.

Dressing enfemm in secret, staying in the closet, and even “under-dressing” can make someone feel like they are privately rebelling against perceived oppression. I’m sure cross-dressing doesn’t solve personal problems for most people, but when done in moderation and conscientiously, it is a heck of a lot better than some of the vices listed above.

So WHY do I like to wear women's clothes? What a question! I've been trying to answer that for a couple of decades now and still may not have the answer. I've had many theories. At first I thought I'd someday discover I was gay. But I never developed any attraction to men. Or maybe "misdirected adolescent sexual cravings and as I get older they will pass". Well, there may have been something to that one but they never passed. Or maybe an outward manifestation of a sensitive, feminine side, an appreciation for all things feminine? Not bad. Then there is the envy of women, who have so many styles of clothes, hair, make-up at their disposal to custom their look to their mood. Men can’t do a whole lot to look special. I am in awe of the "transformation" whether it's a girl looking special for an occasion or a man who can appear as the opposite sex.

Another great incentive is the "escape". Temporarily becoming Heidi is a great way to forget about life's everyday trials. When I'm feeling frustrated or anxious my imaginary world is an intoxicating drug. I am so carefree and upbeat. I read how someone else put it: Heidi lives in the moment, no future, no past, just enjoying the details at hand.

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