Why Do I Crossdress?

Why Do I Crossdress

Why, why, why?

I imagine most of us have, sometime during the course our lives, sat down and pondered why we cross dress. Why we have that burning desire, no…, let me rephrase that: why we have that essential, irresistible, unforgiving urge need to now and then don women’s clothes and, for however long we are able, portray ourselves as female.

I guess a simple, yet somewhat flippant, answer would be: Well, I don’t know, I guess I just like to be like a woman now and then. However, if you spend some time contemplating this aspect of your character, you may find that there is more to it than that.

So, furrow your brow, takes a few moments to reflect and think:
Why do we do it?

Clearly, as with almost all T-people, it is something we were born with—so is it to do with whatever happened to us in our mother’s womb? The oft mentioned “Oestrogen wash” for example?

Or was it something in our social development, our upbringing where, say, we were the only male in a household of females? Or did we get cajoled into playing girls parts in school plays at school—and secretly enjoyed it?

Do we have a feminine looking body—in all or part? Maybe long slim legs below a male torso, or slender fingers, nice skin, long eyelashes and/or a girly lips/mouth?

What about our characters? Don’t like the rough and tumble of boys or men’s games, don’t like getting our hands dirty, but rather enjoy more passive activities such as reading, painting, even knitting (many men do!)? Don’t like the typical coarseness of men?

Do we simply admire the textures and feel of women’s clothes compared with the drab, coarse fabrics men usually have to wear; suit and tie, trousers and shirts, compared with skirts and tops, and dresses in silk and lace, nylon and satin, cotton and, oh, so many other fabrics and styles (long, short, mini, tight, flowing, loose…).

Let’s not dwell on shoes and boots and sandals, we’ll be here forever, but just think: high heels, low heels, flat shoes, thigh length boots, calf length boots, ankle boots; and hair adornments, earring, bracelets, rings, necklaces; scarves, shawls, cardigans… in colours sometimes we have never dreamt of.

Or is that we are simply, fundamentally women?

Women hidden inside a male shell; hidden because general society is hypocritical towards people who are just that little bit different. Fearful of something out of the ordinary, fearful of diversity, the majority suppress the minority (as always...).

Do we dress because we are rebels? Dress because women can wear men’s clothes and no-one makes any comments but, put a man in a dress, and the world might as well end?

Do we dress because it is our sanctuary, our shelter from the tough, tough world of being a man; from being the hunter and provider, being the figurehead?

Frankly, whilst I have my own opinions and thoughts about why we do what we do, if I’m truly honest, I’d have to say, despite all of my questions, a resounding: I don’t really know!

Still, this article this might give you something to think about the next time you slip in to a nice pair of panties and bra, breast forms, tights and a dress, and get ready to show the world the real you! Mightn’t it?


  • bill

    i love dressing as a woman it makes me crave the taste of a mans penis

  • Steve

    On and off for many years I've asked the question "Why do I crossdress?" Never finding a real concrete answer, and now I am pretty sure that I never will. Although, the question of "Why do I crossdress?' still surfaces now and again, I realize that the best thing to do is to accept it and enjoy it. So the best answer to this question is exactly what you wrote – "I don't know, I guess I just like to be like a woman now and then."

  • Casey

    I have been dressing since the of 5 or 6 I am alot now and have a wife who likes me dressing up for her. We will do things like go shopping for panties, clothes and whatever else we can think of. I have never been happier just wish I could dress up more often. It is nice to know that I am not alone in doing this and unfortunately my wife is the only one that knows this about me. I am not sure how to or if I should tell my family, not sure if I want them to know. But in some I want to let them know, what's a person supposed to do?


    I have always had a fascination with women's things…. Was always checking out my mothers clothes and make up… Always interested in women's fashion,,,, Hairstyles, and make up

    Have always been more passive, and love the feeling of being feminine….. Since taking hormone supplements, not only has my body changed, but the way I feel and think is more like a women…. I love it

  • JoAnn


    What a good , thoughtful article! Almost all your comments apply to me; however, I still enjoy watching and talking about football. I have enjoyed going back onto the hormone supplements from En Femme. After only 30 days, I see and feel a real difference. Like James above, the supplements allow me to feel femine even when I can't dress as I would like. Sometimes, I feel so isolated out here in the world we live in. It helps to know I am not alone.
    Thanks, JoAnn

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