Well Heeled

No matter how much of a transvestite, cross-dresser or drag queen you may think you are you are't anything until you step into a pair of high-heeled shoes.

One could write a book on the social implications and ramifications of the high-heeled shoe in our society, it's history and it's impact on fashion. I don't have enough time to cover that story but I will tell you one of my own.

I remember the time period but the details have gotten sketchy with time. I had confessed my cross-dressing to my girlfriend with whom I was living. We were open and talked about it and she was very understanding. She made suggestions for make-up and wardrobe but honestly, I was interested in looking sluttier than her. Not that it was competitive in any way but she was a woman of style and beauty.

Anyway, It was a Saturday, I drove into New York City to Lee's Mardi Gras boutique over at the end of 14th Street. At Lee's you'd ring the bell at street level and then wait for the elevator and the door to open, step into the tiny elevator and rise up to the showroom floor. The people at Lee's have always been super friendly and helpful. That first time in there I was nearly overcome by the clothing, undergarment and shoe selection available to someone my size. I picked out a pair of black leather pumps with a three-inch spike heel and tried them on, of course I was wearing pantyhose beneath my jeans.

After leaving, I put them on in the car and drove home wearing them.

One night soon after that, I was anxious to give my shoes and myself a road test. My girlfriend was asleep; dead to the world. Excited by the prospect of stepping out on a warm New York night dressed in my female finery. I put on a pair of dark pantyhose a short black skirt and some kind of loose black top. With some make-up applied in the car I probably thought I looked pretty good,

I drove into Manhattan and parked on the lower east side near the Pyramid, a dance club with a reputation for being friendly to gender benders which was my intended destination. When I reached the door of the club I stopped, I didn't go in, I couldn't tell if there was a door policy and the people standing in doorway were bouncers who were ignoring me or just people standing blocking the door. I don't remember how long I stood in front of that club on Avenue A. I felt stupid, yet individually defiant; a man dressed in women's clothing at night on the sidewalk in the most famous city in the world.

At some point I changed my mind about going in (Maybe it was based on a fear of crossing some barrier that it would be just too difficult to come back from,} then I walked across the street and through Tompkin's park. Sitting on a bench, just reveling in the fact that I was wearing a skirt, pantyhose and high heels out in public. The only person who approached me was someone selling ecstasy, and he was very non-judgmental about my attire.


After sitting alone in the park for a while I felt like I needed to connect with someone or to experience some cross-dressed sexual thrill. I walked back to the car then drove to a peep show near fourteenth street and third. I walked into the peep and got barely a raised eyebrow. I carefully studied the menus of the various videos available in each booth, as if making just the right choice would assure the ultimate sexual titillation and thrill. And, upon seeing me make the right selection a handsome stranger would approach me and profess his or her own secret sexual fetish, which would mesh perfectly with my own. I went into a booth and watched a couple of bucks worth of a bisexual-cross-dressing lesbian video then walked around the nearly empty store. I left disappointed; there had been no discernable interaction with another human being recognizing how I was dressed. Walking across Third Avenue to my car a convertible full of young men drove past and yelled out "Nice Legs!" they hooted off down the Avenue.

The night wasn't yet over so I drove to another peep on Eighth Avenue near Madison Square Garden. Whenever you enter a peep the rest of the customers always look up, some kind of instinctive reflex harkening back to fight or flight and a time when places like this could still get raided. So I tried to give everyone an eyeful as I strut into the shop, my long legs in a short skirt tottering on top of high heels. The few customers that are in the store look me up and down and decide I'm not their cup of kink. Just like the last place I'd walked in to, I'm in here looking for the impossible, someone who'll share my fetish and become my friend as we get to know each other.

That really wasn't going to happen here.

I walked around the shop admiring the displays of magazines, videos and sexual devices. Feeling on display myself and reveling in that feeling. When I approached the clerk at the raised counter for video tokens he looks down at me and says with a open empathy, "Honey, get a wig!"

I drove home humbled by the experience. Brought back down to earth by a clerk in a polyester flower-print shirt and a comb-over working the overnight in a Manhattan porno shop.

I bought a wig.