Wednesday, December 03, 2003


Andy Williams and Ozzy Osbourne are both celebrating birthdays today. For some reason, I find this incredibly amusing.


I've been spending the last few days helping a friend make some discoveries about himself. Seems he's experimenting with cross dressing. On the one hand, it was, as you might guess, a bit of a surprise to Husband and I when he revealed this predilection. On the other, considering the things he's done over the years, it fell right in line. I wouldn't say that he was actually an outrageous person. Rather, he was always oscillating between high levels of self development and puzzling acts of self destruction as he struggled with his assorted issues. He was a rather bitter person.

But slap him in some thigh high black 6 inch platform heels, buttpads, breasts and a black mini skirt, and he cannot stop giggling.

I must admit I never expected to be playing dress maid to a transvestite. I'm learning a great deal, like I have no capacity for suffering those kinds of shoes. Or Underwear. Well, I knew about the underwear. I am no fan of Serious Support. When you see the words "Foundation Garments", this is what they mean. You could build a house with this stuff.

On the other hand (this is my third or forth hand in this post, isn't it? Must find another transition phrase) I'm surprising him with the assumptions I make about his new "hobby" -- like, that one day we will go shopping while he's wearing drag. This idea, and my blythe assumption of it, gave him pause, right before he fell over giggling about it.

The giggling is new. He's one of our more macho acting friends.

Unfortunately, he will never be a very pretty girl. As he says, he'll never "pass", so he's aiming to be a Man In A Dress -- but an impressive Man In A Dress. He'll have a major rack (which he cannot stop playing with) and a nice ass (which he cannot stop admiring). I feel possessive about that ass. I was the one who figured out what the spare pads were for and I'm the one assigned to putting them properly in place. I made that ass. I'm threatening to sign my name to it, "Ass by Sherri".

A big concern is secrecy/discretion. We don't live in an area highly friendly to alternative lifestyles. Moreover, there are any number of friends that simply Do Not Want To Know and there's no particular reason to ruin their day with it. It's a weird yet understandable situation. How lovely it would be if we knew with perfect confidence that all the people in our lives would accept everything about us. Lovely, but not practical. I think the most we can ask of anyone is mutual disinterest -- I won't shove what I do into your face, and you won't stare at things that upset you. We are acting as "way station", storing clothes and makeup and so forth, because our friend has room mates (who are those people who don't want to know so why torture them). If I wasn't certain that few (if any) people who know us both would read this site, I wouldn't write about it. And vagueness helps.

The biggest problem to arise is when our friend must end "dress up" and go back to the world. At this point he doesn't want to try living in drag. I don't know (and neither does he) if he is transexual. He's very definitely attracted to women exclusively. He bought himself Double D's and delights in just holding them in his hand, letting them jiggle. I think he likes retreating to his male persona to deal with some things. However, he's having so much fun being a girl that it leaks out when he's being a boy. Acting that way in prosthetic breasts and fuck-me pumps is one thing. Acting that way in sloppy sneakers and baggy jeans gives an entirely different effect.

My biggest observation is this. Drag Queens do not act like women. They do not act like men. They act like Drag Queens.

We have to find makeup foundation that matches his skin tone.

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