crossdresser






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Generally I don’t like going out on weekends if my wife is around, because we don’t really get to see each other too much on account of A: full time job, and B: Commute time, but when the opportunity to go out dressed presents itself, I at least try to take it. On this occasion, I packed up a bag and headed into SF to hang out with a friend of mine. Got to her place. Got changed. Got made up. Got nervous. Got outta there!

Out on the town… Sorry, town…



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A lot of stuff has happened over the last few months. I’ve been out a few times with friends. Completely dressed up in flapper garb at a company party. And generally just being more open and honest about everything. Feels good :) One thing I’ve learned today, however: sunlight does not do wonders for my face. Frickin’ stubble! No getting around it for now though.

Newest pics


I’ve been a bit on the snowed-under side of things for what seems like months now. A few weeks ago, I bought some new clothes, and hadn’t really had a chance to actually try them out. In between working on side-projects, and being summoned to squash bugs on sunday mornings, I finally managed to get a chance to get dressed up and take some pics.   It was a bit too dark for the webcam after a while

While you were watching the Superbowl, I was attempting makeup.



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So last night, after much hemming and hawing, I put on an outfit, and left my apartment with a friend. Out in public. Oh god. The wine in my system seemed to calm my nerves, and the fact that there was a friendly face with me helped too. My expectations were mostly to be, you know, beaten with sticks, set-upon by a bloodthirsty pack of homophobes, each kitted out with a gut-spilling spear, a sign saying “KILL ALL TRANNYS” (because clearly, they wouldn’t be able to spell ‘Trannies’) and a loudspeaker to announce to anyone outside the nearby vicinity that, […]

Out in public: A whole new world


Ok. So in a previous post I mentioned how much I wanted a pair of black, sparkly TOMS shoes. So I bought them. And I don’t like them. I’m not really sure what the issue is – they still look cool in the picture, but on… I just haven’t found anything that works with them, in either male or female mode. Maybe it’s because they’re not heels. Maybe in going for the black-sparkly, they turned out to be a bit too dull. Maybe it’ll just take a bit longer to figure out the right outfit. Maybe I should’ve gone for the red! […]

TOMS, Part Deux



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  As usual, you take thirty or forty photos, pick the one or two good (or at least, not-terrible) ones, and then discard the rest. This one’s not too bad – one day I’ll have to deal with my freshly-shaved face differently, on account of my stupidly dark stubble. Maybe better foundation/concealer. Or something else. Would love to hear some tips! Somewhat full-length. But sitting. Couldn’t get a good standing pic :( I desperately love these boots! I’ve got a bit of a stupid-face going on. Then again, you didn’t see the other ones :S Some days are good and […]

New pics!


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“All right”, I thought. “Today, I’m gonna go for it.” 30 mins in the shower shaving legs, arms. Another ten mins in the bathroom while I shave my face. Moisturize. Looking pretty good. Grab some clothes out of the closet. Tight t-shirt, ridiculously skinny jeans, pink suede heels (trust me, they look better than they sound). Wig, forms. Mirror.   Oh hey, my lip has inexplicably swelled up, and there’s a small scab on my nose that, all combined together, makes me feel really, hideously ugly. Feel fat and mishapen.     Well, I guess we’re done here. :/

Annoying.



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Being a crossdresser’s pretty tough – there’s this thing that you want to do, but it’s (annoyingly, and stupidly) frowned upon by most people (or at least, the internal paranoiac seems to think so). It’s also hugely visible – it’s difficult to not stand out of the crowd when you’re 6’3 in clicky heels. And yet, that urge to wear what you want and not be shunned or shamed is pretty strong. So what do you do? There are a few ways that I’ve battled with it out and about – and one thing I’ve found that somewhat sates the […]

How To Crossdress (Sneakily)


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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 […]

Ah, the face of the Miserable Crossdresser.