When I wear a dress I am not cross-dressing


Most days see me wearing women’s clothes, or should I say, clothes that are typically gendered as female.  I don’t go to the office dressed “en femme” and in truth, even wearing women’s clothes in my mind is not about being “en femme”.  This is an important distinction between cross-dressing and what I would call just dressing in gendered clothes.

I don’t wear skirts because they will make me pass, or because I get aroused by them.  I wear them because I like how they make me feel about my body, and because I look good in them.  I want to see the curves that I have and to accentuate them.  My self-image requires that for a happy sense of self.  Body image lies at the foundation of our confidence.

When I think of a cross-dresser, I generally assume that this is a fetish.  That cross-dressers are aroused by wearing women’s clothes, that putting on panties, hose, and clothes, putting on wigs and makeup, are all things that play into a narrative that the clothes turn you into something different.  I always wondered what was the matter with me to have a compulsion to wear women’s clothes, but to never feel even faint stirrings of sexual arousal while doing it.  I couldn’t explain it.  Makeup and wigs have never done it for me, in fact, they do the opposite of what they should—because I feel they make me look more male, by calling attention to me in a way that says, “something is off.”

There is an awful lot of online porn that is about cross-dressing, and it seems to me that very often there is a strand of humiliation that runs through it.  Sissy porn, in particular, taps into this idea, that dressing female and becoming a “slut” to men are somehow connected.  Degradation for many can be a very powerful aphrodisiac. I struggle with this in relation to myself.  I don’t judge and I do not discount the appeal of the whole “sissy” narrative, but I dress to feel good about myself, and somehow the “sissy” narrative feels like it is designed to arouse you by making you feel worthless and bad, or dirty.

As a gender dysphoric, finding a happy place for my own mental health, has to begin with a positive self-image.  I do this in several ways:

  • Build a lean, skinny, flexible body and do exercises that emphasise female attributes…try looking on youtube for exercises on “snatch waist”  or “booty lift” and you will get the idea.  Both of these have tightened up my waist and given me a firmer, lifted butt.
  • Diet and weight loss to ensure that women’s clothes fit—sleeves, legs, waist, butt…and that my body can be loose and move in them
  • Wear women’s clothes that flatter a skinny male body—long dresses, clothes designed for skinny women with flat chests, and skirts that show off my legs.

On and off over the years I have also practised tight-lacing corsetry.  For many years I did this while I was still growing, and although corsets are not supposedly changing your rib cage shape for good, I do believe that years of wearing one during the day and sleeping with it on a looser setting, did eventually make a difference.  Today, wearing a corset is the one nod I will make to altering my body, and save this for times when I am out in public and want my figure to be more curved.  Mostly this would see me wearing a pair of skinny jeans or cigarette pants and a white blouse.

I never wear wigs or make-up in public, though have tried them enough to know that they don’t work for me.  I do love to paint my nails though, but that doesn’t seem to count.

It encourages me that more and more young “boys” are having the courage to wear skirts and dresses in public.  This may be tied to the increasing openness towards trans people and trans issues.  I would guess that such “boys” are not cross-dressing, but are rather more likely to be trans.  No value judgement, just very different motivations, very different sexuality, very different goals.  And while the distinction may be trivial for most, in my mind we are not talking about a continuum here, the motivations are totally different.

As I understand it, most cross-dressers are straight (with the obvious exception of the drag queens). Separately, most trans people find their orientation changes during transition.  I don’t really know what to make of this, as I can’t imagine that will be what happens to me.

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