A Beautiful Risk

Tired of hiding the truth, she transitioned into a male sex worker. He’s been in a struggle with societal norms — and himself — ever since.

On a damp Wednesday evening, while chain-smoking on the patio at a Tenderloin gay dive bar, Stephen Gray decided he wanted to rehearse. His performance, which would be part of an art exhibition put on by male sex workers, was a little more than a week away. He had yet to show it to anybody.

Gray downed the last of his straight-up Maker's Mark, stubbed out a Marlboro Light, and trotted back into the dim caverns of Deco, one of his regular hangouts. Still, for what he wanted to do, he'd need permission from the bartender.

As he squeezed into a group of men ensconced at the bar, Gray quickly became the center of their attention: a role he plays well.

Michael Rauner
Naked but for a cross, Gray reads a story he wrote about the night he was penetrated by an HIV-positive client.
Michael Rauner
Naked but for a cross, Gray reads a story he wrote about the night he was penetrated by an HIV-positive client.

At 28, Gray is fit, boyish, and effortlessly articulate — a gay man's dream. He looked out intently from behind smart rectangular-framed glasses and wondered aloud whether he could put on a little, um, X-rated performance?

"I wouldn't mind," the bartender said, scrunching his face. "But I'm not sure about them." He indicated a group of guys sitting at the edge of the bar with a clear view of the adjoining room where Gray hoped to perform. Gray would have to ask them if it was okay.

"Okay?" one said. It was better than okay.

"I'm not what you think," Gray warned.

Whatever, the men agreed. This is San Francisco.

Gray took his place in front of a cranberry crushed-velvet curtain, placed his typewritten story in his mouth, and removed his jacket, his AIDS Walk T-shirt, his A's hat, his jeans, and everything else. He stacked them in a tidy pile and held the story just below his chest, which is punctuated with two nipple rings. Thick trails of hair trace his areolas and plunge down his midsection into a soft, hirsute patch. Below it, there's only thigh.

As in, Gray doesn't have a dick.

Even though he has gone through a standard female-to-male transition, he has opted to keep what he refers to as "original plumbing."

At the back of the bar, somebody cackled and Gray went rigid. That's one of the risks of baring it all, and Gray is no stranger to those risks. People might not like what they see. It might scare them. They might judge him. So although he craves the attention, and wants to reveal his entire being to this bar, to San Francisco, and to the entire world, he finds himself bumping up against stigma and shame.

Making it even more difficult, Gray spent the first two decades of life as a girl who could do no wrong. But he got tired of hiding the truth, so he transitioned and became a sex worker, and he's been in a war with societal norms — and himself — ever since. One lost battle in the effort to expose all: Stephen Gray is a made-up name.


Gray's telling of the story of his former self usually requires a lot of energy, cigarettes, and alcohol. Luckily, the last two are in high supply at Deco, and Gray is almost always up for an impassioned discussion about the challenge of being Gray. He settles down onto an outside bar stool, and in an elfin voice and a highly focused manner, he begins to talk. He talks for more than two hours, stopping only intermittently to be asked a question.

Gray's perfect girlhood began in Anaheim, California, but the man he is today was born in Thailand a little over five years ago, in what is known as the gay ghetto of Bangkok.

He was once a young woman (we'll call her Stephanie Gray), a driven scholar who was fluent in Thai and had been awarded a prestigious Fulbright fellowship. Fulbright grant money — which has funded a significant number of people who later received Nobel Peace prizes — paid for Gray to live in Thailand while volunteering as an HIV caregiver at an orphanage and fighting to procure antiretroviral drugs in northern Thailand. She had also planned to study how stigma surrounding female sex workers there affected the perceptions of how HIV can be contracted. But her plan was slowly going awry.

Gray often found herself surrounded by empty whiskey bottles and hunched over her computer, typing away at a novel. It was mainly about the people she had known who had died of AIDS, but there was something else that seemed determined to fight its way in. Gray had a creeping suspicion that she was actually a man in a woman's body. And not only that — a gay man.

For most of his former life as Stephanie, Gray dated men, but rarely felt comfortable in those relationships. The idea of being part of what he calls "a heteronormative couple," where the man would open the door for the woman and tell her how pretty she looked, was appalling. To compensate for that, Gray felt the need to play the dominant female and controller of men.

But something was still wrong. Although she desired men, and in fact, she was "dreaming of sucking cock every night," something about heterosexuality didn't click. Gray felt a barrier between herself and men.

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