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She wore a torn dress, and a neon blue wig whose braids were tied with multicolored condoms. Her pupils were feline-ovoid, her irises pale yellow. Below the unblinking eyes streamed a lava flow of red-glitter tearstains. Her pubic hair under the torn dress was a second wig, black and wiry — an Afro, and it seemed to expand through the sad striptease, from Gary Coleman to Richard Pryor to James Levine, until it finally detached from her body to reveal a gold sparkly painted penis.




"That's the one," I said to the cheering woman beside me, "who I want to have sex with."




After the show, minus two wigs, the performer stood there looking simultaneously vulnerable and hazardous in her glitter-bedraggled makeup and inhuman contact lenses. I was a little starstruck as I started a conversation. This was no ordinary post-gender, PTSD-addled, violated-clown drag queen, this was

the reigning Miss Trannyshack, the highest title attainable in new-wave drag north of Sunset Boulevard and west of the Hudson River. That night's performance had been my first exposure to the drag confection known as Raya Light, and standing there before what was left of her, I felt a powerful muscle of instinct — the one that impels me toward the mucous membranes of celebrities — go into a full seizure. The impact reverberated up my torso and through my organs of speech, which blurted, "So, do you want to go downstairs?"




Downstairs, in the sex dungeon, we found a spot on the far end of the upholstered room and reclined. As we lay in each other's arms with various sex acts going on around us and the occasional limb gratuitously grazing ours, Raya fed me a series of absurd, mostly unflattering falsehoods about herself and lightly barbed

insults directed at me. All I remember is laughing while I cringed, and the more I laughed, the more I wanted her. So I kissed her. She didn't kiss like a cat person, or a psychotic animated horror doll; she kissed like a guy, and she had a hard body. Then I went down on her, and a bitter taste filled my mouth: gold paint.




So much for oral sex. And anal sex in a basement dungeon on a first date, as everyone intuitively knows, is uncouth. After an hour of light foreplay and kidding around about icky subjects now forgotten (child molestation? open sores? the unsolicited caresses of adjacent dungeon dwellers?), it was nearing three in the morning, well past time for me to get my rocks off and go home to my boyfriend. But whatever impaired my memory that night had also made it difficult for me to come. I let Raya try for a while before I took matters into my own hands. I tried light and fast, hard and slow, without lube, with lube, more lube; I tried spiral strokes and bending it back, butt simulations, Raya's hands on my balls, her tongue in my ear and my nose in her armpit. Finally, I resorted to brute force, and ejaculated just at the point I thought my forearm might burst into flame.




Like many people who have sex in front of other people, I don't object to being watched. But I have my limits. Having half the room shout encouragement as I approach orgasm is pushing a boundary; having someone nearby bellow, "And the Oscar goes to…" when I've finally come, as happened in this case, is crossing it. Raya made a crass remark about my scenery-chewing ejaculation. "Thanks a lot," I said. She just laughed, and licked something off my chest.








"How was your night?" asked my boyfriend, James, the next morning.




"It was okay," I said. "I had sex with Miss Trannyshack 2006."




"Who is it?" James asked.



I told James about Raya's tragiclown persona. "She's forty," I said.




"How's the body?"



"Kind of amazing," I replied, thinking of the muscled hemispheres of her ass, the smooth and defined chest, the firm, gentle swell of her belly. "She said she was some kind of professional tennis player. But I'm not entirely sure — I could never really tell when she was bullshitting me."

James Googled Raya's boy name, revealing that she hadn't been bullshitting about the tennis. The previous year she'd ranked No. 2 in the U.S. senior men's division.




"He can beat your ass in tennis," James said, quoting a favorite song, "before you fuck his ass in bed. Did you get any pictures?"




James doesn't ask a lot in return for my sexual carte blanche. If I meet a guy I think James will like, I can bring him home to share. Otherwise, our policy is one of Do Ask, Do Tell: details, pictures and, if possible, video are the price of sexual freedom. I'm not sure my tricks actually believe me when I say I have to take the videotape for my boyfriend, but they usually relent.




One morning a few days later, after my second encounter with Raya, I came home to James without even an anecdote to justify my absence the night before. Raya and I had met at Trannyshack, which gets going at about 11:30 on Tuesday night. We'd hung around through the last act of the midnight show, had a few drinks and danced a little before heading back to her place. She drove a big boxy new Volvo and brought me back to her big boxy new outer-Mission loft. Inside, the place had the clutter you might expect from a bachelor-tranny tennis champion: unwashed dishes and bras strewn about, wigs and rackets, the Miss Trannyshack tiara and a few tennis trophies. Upstairs, the bed was positioned beside a full wall of closet-door mirrors, but all they reflected that night, before we passed out near four in the morning, was a futile search for condoms, the exhaustion of a minute supply of lube, the subsequent retrieval of I Can't Believe It's Not Butter Spray from the kitchen, and finally my passing out, smelling of margarine, after the weight of yet another withering remark about Oscar-worthy orgasms broke my will to come.