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No Sacred Cows  
Toby Young
Sunday 17th October 2004

I was a Lesbian for a Night


As far back as I can remember I always wanted to be a lesbian.

I admit it's a strange ambition. If I like women, what's wrong with being a straight man? Two words: Pillow fight. Most men fantasize about spying on lesbians; I want to be one. So I became one. With the help of a crack special effects team I disguised myself as a woman and embarked on a whistlestop tour of New York's hottest lesbian clubs. The plan was to approach gorgeous young lesbians, draw them into my confidence, then make out with them on the dance floor.

Things did not go according to plan.

Looking at myself in the mirror, there was one major problem: The bulge in my crotch. (Okay, it was a minor problem.) How exactly did professional female impersonators hide their genitals? I made a few inquiries and discovered that an essential component of every transvestite's wardrobe is a pair of "tuck-in panties." Next came hair and make-up. At 7.30pm on the night in question, a husband-and-wife special effects team came to my apartment, armed with a selection of wigs and a suitcase full of make-up. About an hour later I inspected their handiwork in my bathroom mirror. Good God! I had no idea I could look so pretty. I was a knockout.

Shortly after the special effects team left, Olga and Caroline arrived. Rather than turn up at the clubs on my own, I thought I'd be safer if I went with two attractive women. I stalked up and down an imaginary catwalk in my living room and asked them what they thought. Pretty cute, huh?

"I was going to pretend I fancied you much more as a woman but I can't go through with it," deadpanned Caroline. "In fact, you look so gross, I don't think I'll ever fancy you again, even as a man."

I turned to Olga for support. Olga's from Greece and her taste is a little more sophisticated.

"You look imbaisable," she said.

"See," I said to Caroline. "She likes me."

"That's French for absolutely unfuckable," Olga explained.

The first stop was Ruby Fruit on Hudson Street. The women in Ruby Fruit are not what you'd call lipstick lesbians. They're hard-core dykes. I'd been warned by several veterans of the New York gay scene that if the denizens of Ruby Fruit discovered I was a man there was a good chance they'd beat the crap out of me. I joked that I wasn't scared of a bunch of lesbians but, in reality, I was terrified. Several of them looked like German shot-puters. We decided to make a sharp exit.

Olga was so traumatized by Ruby Fruit, she decided not to join Caroline and me at our next stop: Henrietta Hudson. On Friday nights Henrietta Hudson turns into the G Spot which, according to The New York Press, is full of "cute downtown lesbians." I wasn't disappointed. The dance floor was heaving with gorgeous young lesbians rubbing up against each other and sticking their tongues down each other's throats. I grabbed Caroline and headed into the fray. Within a few minutes, we'd singled out a pair of hotties that could have given Ellen DeGeneres and Anne Heche a run for their money. By the end of the first song I was dancing opposite a blonde goddess, a smile glued to my face.

I introduced myself as "Jennifer", asked her if she wanted a drink and retreated to the bar to collect my thoughts. What if she wanted to go home with me? After fooling around with her for ten minutes, it would be pretty obvious I was a man. How would she respond when I whipped off my "tuck-in panties?" I bolted down a double-Scotch and headed back to the dance floor.

Strangely, she was nowhere to be seen.

"Sorry Jennifer," said Caroline. "You weren't her type."

I was devastated. The problem wasn't that she'd suspected I was a man. I was just one ugly ass lesbian.

The final stop was Mother on 14th Street which plays host to the Clit Club. Inside the atmosphere was electric. Lithe young bodies writhed around on the dance floor as Latin house music was pumped out of the PA system. The place was so packed it was almost impossible to move. Suddenly, someone tapped me on the shoulder.

"Aren't you Toby Young?"

I spun round in horror. There, standing before me, was a woman I'd met several times before on the New York literary circuit. She had a reputation as a hard-line feminist.

"No," I said, trying to pitch my voice as high as I could without sounding ludicrous. "My name's Jennifer."

She nodded skeptically.

"Can I buy you a drink?" I squeaked.

"Are you working on a story?" she demanded to know as I tried to squeeze past.

She made a grab for my wig but I dodged out of the way. This was getting ugly. Dragging Caroline behind me, I pushed my way to the exit as fast as I could. Were we being followed? I didn't dare look. After we'd run a couple of blocks we finally hailed a cab and I decided to call it a night. Being a lesbian had been a lot less fun than I'd hoped. In fact, it was downright dangerous. Next time I have an urge to make a voyage of discovery, I think I'll stick to East Timor.

GQ, February, 2000

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