The Need to Crossdress: Blessing or Curse?

I titled this article the “Need”, which I think accurately describes this compulsion we all seem to share here. Although dressing ourselves up to one extent or another in women’s clothes brings us together, we all travel a different road getting here. Some have dressed since childhood, others were smitten much later in life, either way, our paths are running together for this while. While some of us just dress occasionally, others here live full-time as a woman, and still others have transitioned, or are in the process of doing so. Many are simply happy to dress occasionally for decades. Even for those dressers who don’t do it often, to suggest that this is a “hobby” diminishes it much too much, and if this term is used, I find myself rather offended by it.

This is something that I’ve been thinking about for some time, as the act of dressing up in women’s clothes can cause us so much trouble and distress in many ways. The satisfaction when dressing can sometimes be described as a “high,” but is so often followed by a deep low with a promise to “never do it again” to ourselves, and often to others.

But that never seems to be true.

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After talking to many other CDs and TGs, the common thread is we really don’t seem to have a choice in all of this. Some of us have been told by someone to simply not do this anymore, and often we try, but it always seems to come back into our lives, whether it is days, months, years, or even decades later. It’s not as cut-and-dried as what kind of car do you like to drive, what brand of jeans do you like to wear, or where you like to have lunch, etc. Those are choices, this is a compulsion. So with all of the complications this causes in our lives – separations, divorces, lost jobs, friends, alienation from relatives, addiction, even suicide – why on Earth, would anyone ever WANT to do this?

Put like that, we must all be crazy, or something. However long we are able to cast away our feminine side, it always seems to come back to us, and more insistent than ever before. Like a debtor you’ve been avoiding for some time, you turn a corner, and there she is! Right in front of you, and insisting you pay her back with interest!

Most see-saw back and forth between our two sides, like a person with an eating disorder, binge and purge, over and over again. At times this must seem like some kind of curse that we are burdened with. Then when we give in – that indescribable euphoria, sexual for some, or just the peaceful feeling of not just wearing women’s clothes, but becoming feminine for a while. Mostly, it just feels “right”.

What is the allure of this mystic femininity that draws us in? For me, it’s the beauty which is the shape of a woman, the curve of her breasts, hips, and buttocks, but I have no idea why instead of just simply loving them, I want to look like one. My perspective is from a hetro person, though there are those here who identify as bi or gay. One’s presentation as either male, female, or androgynous, has nothing to do with one’s sexual preferences.

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I’m sure everyone here can attest that dressing up seems to become more and more addictive! For me, it was the charge I got from simply dressing up in women’s underwear for many years. Now I’ve progressed to an ever growing wardrobe of women’s underwear, skirts, tops, dresses, jeans, shorts, and even bathing suits. There is definitely something of a compulsive aspect to buying clothes, too. Then there is the look and feel of these clothes. The materials are generally softer than men’s, the colours and textures are so much nicer, the styles are more varied and often flamboyant. Though that’s the icing on the cake, I think. Even without those beautiful-looking things seducing me, I’d still want to dress up, even if all I had to wear were women’s Soviet-era clothes!

I was very confused for a while as to where this was taking me, and to an extent, I still am. However, at this point I have learned to accept my femme side as a real person, which has allowed me to start enjoying the ride much more. Personally, I feel that Amy really started to come into her own in January 2019, so I put her “birthday” as Jan 1 2019, though I now realize she has been with me in one way or another all my life. Back in the fall of 2018, I could not have imagined dressing up in pretty clothes, putting makeup on, and going out to a public place. Though these thoughts had crossed my mind for many years, I just thought I could never do it. On top of that, I felt it was simply wrong to want to. At that point I was still just dressing in women’s underwear, my own t-shirts, and jeans. Now I’m dressing up, doing makeup, and showing the world my feminine side, Amy.

Many things have led me to this point, some of them simply a bit of luck, but mostly joining CDH, and learning that I’m not so abnormal after all. There are tens of thousands here, and many others scattered throughout the world! There are also historical records that show men have been dressing as women for centuries, or longer. So this is nothing new at all in the broad spectrum of human nature.

I believe the key is to simply accept who you are, and not try to understand the “why” of this so much, as there is little in the way of answers to that question, I’ve found. It’s like, why is someone a musical genius, a talented artist, or a top athlete, for example? Why do some understand the intricacies of mathematics, and others struggle with simple addition? They simply are what they are. We somehow need to get to that point in our community and beyond.

At its simplest, these are just the clothes we choose to wear, and that by itself shouldn’t be able to hurt anyone. Though of course it often does, as society tells us men are supposed to act and dress a certain way. And since we aren’t wanting to conform to that norm, others get upset.

If you feel you need some professional help to get to the point where you are able to accept your gender fluid nature, then seek out a qualified counsellor, preferably one that has experience with gender issues. Once you can begin to accept yourself, then you can better enjoy this beautiful diversity which your life has given to you. Whether you choose to continue this journey as a crossdresser, or you feel the draw to make the transition into full time femininity, you are on this journey, and you may as well enjoy the ride.

After struggling with this for some time, I’m now at the point where I feel that this is a blessing in my life. It certainly makes things more complicated, and will continue to do so as I go through the rest of my life. Amy is as important a part of me as my wider-known male persona.

So, what do you think, is this a Blessing or a Curse for you?

Have you been able to go from one to the other?



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Amy Myers

I'm 60+, hetro, married, and love dressing up! I keep saying and feeling like I'm new to this, but I have dressed from time to time since my pre teens, but just late 2018 it seems to have become of a bigger part of me, rather than just a role I played from time to time. I'm interested in music, cars, photography, and plus other interests.

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Holly Morris
Holly Morris
1 year ago

HI Amy! What a wonderful article! I just came across your article today, so I’m glad I had the opportunity to find it and read it. Everything you wrote resonates so very strongly with me, as like many of us, I have struggled with this my entire life before I finally realized that Holly is a real person and has real dreams, desires and needs. It’s not just about dressing and making up like a woman, it’s about becoming a whole person. The truth is that Holly is as real as my male side, so being able to accept her… Read more »

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