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…

 in Being Out  tagged crossdresser / drunk / makeup / out and about / shoes / wigs by
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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

 in Crossdresser Pics  tagged clothes / crossdresser / crossdresser pics / crossdresser pictures / goodpics / makeup / transvestite / wigs by
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.

 in Crossdresser Pics  tagged AmericanEagle / clothes / crossdresser / crossdresser pics / crossdresser pictures / goodpics / jeans / makeup / shoes / wigs by
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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

 in Being Out  tagged crossdresser / handbags / hats / makeup / Pics / public / shoes / wigs by
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

 in Miscellaneous  tagged crossdresser / shoes / TOMS by
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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!

 in Crossdresser Pics  tagged americanapparel / clothes / crossdresser / crossdresser pics / crossdresser pictures / hats / makeup / Pics / shoes / transvestite / wigs by
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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.

 in Miscellaneous  tagged crossdresser / depression / sad by