Ah, the face of the Miserable Crossdresser. 7


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.

have a picture.


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7 thoughts on “Ah, the face of the Miserable Crossdresser.

  • sissyalyssa

    Are you reading my mind? You just described me, but better than I ever could. Thank You!!! It’s such a relief to know that I’m not alone in my daily struggle with my crossdressing dilema.

    • MyWeekendShoes Post author

      I think there’s probably more of us in this situation than we think! Hopefully we can become more open and more forthcoming with the struggles that we face on a daily basis. Part of the reason for this blog is to present us as we are – normal people with the same basic issues as other people… but with a few others tacked on!

  • Dite

    :( I recently discovered these things about myself and I feel the same way.. A friend suggested cross-playing, which is like anime cosplaying but with the added oomph of “cross”. I’m not a huge anime fan but after being shown some stuff that can be tailored to whatever size you need (not to mention it’s just flipping gorgeous and over the top), I just may try it out.

    Also, i also hate my face. I get told I’m handsome but all it does is make my insides itchier, since that’s the opposite side of the spectrum to what I want to hear sometimes..

    Oh, for the record, you look adorable in that pic.

  • MyWeekendShoes Post author

    Thanks for the compliment!

    I know how you feel! I’m not really into anime either, but I seriously considered getting into crossplay just so that it could be an outlet. I suspect that the popularity of crossplay is at least partly driven by people such as ourselves (though I have no hard evidence) !

    • melinda

      I suspect in dating a guy who likes to cross dress. It wouldn’t bother me if he felt this way. I’m just curious on how to know for sure I have grilled him about being gay but he says he’s not. My nities n panties have come up missing hmmmm what r some tell tell signs

    • MyWeekendShoes Post author

      It’s hard to say – he might still be feeling shame about it, in which case it’s going to be a little difficult to get him to own up to, if indeed he is crossdressing. It might be worth making some suggestions like daring him to wear your panties or something and see how that goes, and then possibly escalate it.