I'm a Legend. No, Really.

I have a dirty little secret--I like to dress up as a man.

But only one night a year and only because I get money for it.

Really, it's not as naughty as it sounds--for the last 3 years I have won "Best Male Drag" at the local gay bar. I'm straight (too straight according to some of my friends) but for some reason I just find this a whole hell of a lot of fun.

I started down the male-drag path on Halloween 2005 when I dressed as a flashy '70s-style pimp complete with goatee, zebra-print jacket and giant red velvet "Bid Daddy" hat. I wore dark sunglasses and carried a cane with a golden dragon's head on it. I looked awesome and apparently the patrons at the bar agreed 'cause I walked out of there with an $25 extra bucks in my pocket. Well, that's a lie--I spent it on drinks. But I walked out of there with an envelope with "Best Male Drag" written on the outside and the proud knowledge that I could fake maleness better than any other woman in that bar that night.

The next year my friends and I decided to do a group costume and we all dressed up as the Village People. I went as the cop and I had some stiff (heh, heh--"stiff") competition from Kiki who was the sexiest construction worker I've ever seen in a gay bar, and my other friend Cootchie whom I feel should have won for her incredibly believable "leather man" (complete with actual motorcycle chaps!). However, once again I went home with that same little envelope and a standard of drag excellence to uphold.

I'm very proud of my 2007 entry. I worked hard (heh, heh,--"hard") to come up with an original idea and I came up with Ron Jeremy. Yes, that Ron Jeremy. I again donned a mustache, purchased some fake chest hair and darkened my arm hair with waterproof mascara. I made up a fake name tag from a porn convention, borrowed a Hawaiian shirt from my Honey and squeezed into my tightest jeans that would show off my fake "package"--a rolled up tea towel. I put on my sleaziest aviator shades and greased up my hair to darken it and keep it off my face and away I went, primed to compete in my third Halloween as "Best Male Drag".

Again I walked away with that envelope, but it was a hollow victory. I was the only entry! I guess word had gotten around that I was a force to be reckoned with (or, more likely, women in my city just aren't all that keen on dressing like men) so even though I won I was disappointed that no one had bothered to give me a run for my money. I decided then and there that I was hanging up my handlebar mustache. No more dressing up like a man for me.

This past Halloween none of us had our hearts in getting all dressed up so it was a non-event for my group of local friends. I was invited to 3 parties but I just couldn't get up the enthusiasm for coming up with a costume so I didn't go to any of them.

On Saturday Kiki needed to go dancing so we decided to hit our local gay bar (yes, that gay bar) and shake our various body parts on the dance floor. There were still a few die-hards with costumes on, but the festivities had already taken place the night before so none of us had the least intention of dressing up. I approched "Bradley the Shooter Boy" who MCs the Halloween costume competitions as "Miss Drew" and asked him who had taken up my crown as "Best Male Drag." He replied that they had to retire the category because no one had shown up to take the prize. Retire a category? Because I didn't slap on a fake mustache? I felt an odd combination of pride and guilt. I felt like my Hawaiian shirt and fake chest hair should be hanging from the ceiling like a retired basketball jersey, while at the same time I felt like I had somehow let the team down.

However, they haven't seen the last of me in male drag--apparently they're looking for judges for their "Miss Club Ren" annual drag competition. And the judges have to also be in drag. Any one have any suggestions?