Site icon My Weekend Shoes

Ah, the face of the Miserable Crossdresser.

I find that I get horribly depressed about my crossdressing habits every so often. Inevitably I wish that I hadn’t been cursed with such a strange desire/burden.

“Why do I need to do this? How did I get this way? Why can’t I be the same as everyone else?”

Some part of it is this in-built shame/guilt about it that I carry around, as if what I’m doing is wrong (nope), deviant (not really), or sinful (ATHEIST).
Another part of it is really just how I imagine a lot of women feel about themselves: not up to scratch. I’m a good looking guy, I think. But one thing I certainly won’t be good at is looking like a girl. Passing. That’s a fact. My broad shoulders and fairly masculine face (complete with a five o’ clock shadow that won’t quit) have seen to that. On top of that, I’m fairly hairy – Sasquatchian, some might say. Yes, I could shave – but I have the added annoyance that the hair is dark, and even after shaving, like my face, it can be easily seen under the skin. And I get terrible shaving rash. and in-grown hairs. And I’m a size 11w in shoes, and all the good stuff is in the sub-size-10 range. ERG

So what do I do about it? I’m honestly not sure. The fact that I am very much a male with all of the above features, and want to look and dress up like a girl for probably 25% of the time are unerring and undeniable facts of my existence that are at odds with each other. I’m a dilemma. Somewhat of a contradiction. A complete mess. And not insubstantially depressed about it all.

I heard Eddie Izzard once describe himself as “A complete boy, plus half a girl”. I think that’s a fairly good description of the state of affairs, but the complete-boy part really does step on the toes of the half-girl part sometimes.

tl;dr: Boo-hoo, look at the sad tranny (We don’t say that anymore).

have a picture.

Exit mobile version