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.
Gray wishes he lived in a world where he could show his face in the newspaper.
Michael Rauner
Gray wishes he lived in a world where he could show his face in the newspaper.
Water has important healing properties for Gray. He swims long distances almost every day.
Michael Rauner
Water has important healing properties for Gray. He swims long distances almost every day.

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.

While at Mills College, an all-women's school in the East Bay, Gray tried to reconcile that by becoming a lesbian. Although Gray refused to provide any photographs of Stephanie, Google Images contains a small photo of a striking young woman with a short dark pixie cut, like that of Cranberries frontwoman Dolores O'Riordan. It's Stephanie's Fulbright picture, and she seems to be glaring at the camera. As a woman, Gray never did like pictures. Or mirrors. Or comments about her looks, particularly when they involved the word "butch." "I wasn't a butch woman," he still insists.

When Gray did try out a relationship with a woman, it fell apart after she lost interest in the sex. "I'd be way more comfortable with a guy tying me up and beating the shit out of me before I'd be comfortable performing oral sex on a woman," he says. "That's just who I am."

Back at the computer in Thailand, thoughts of transition were exploding into Gray's consciousness, and after a friend had directed her to the Web site www.xxboys.net, for the first time she was faced with a series of photographs of transgendered men. "I thought, 'That's me. I'm that,'" Gray says. "I could never look at a man or a woman and have said, 'That's me.'"

From there, Gray had what he describes as a breakdown, which involved getting rid of all mirrors and "fucking losing it." The transition from woman to man became a must. Without that, Gray couldn't see a future.

With three months to go in the Fulbright fellowship, Gray abandoned the project and flew back to America to undergo a transition. After learning of her decision, Gray's father took her off the family insurance, so she had to take out a loan.

A psychologist signed off on Gray's mental fitness for transition, and soon she was injecting testosterone at the hip. The hair came in fast on the face and chest. Some of it around the edges of his hairline even receded, man-style. The fat distribution changed. The voice gradually deepened, until it no longer gave any hint of femininity. Also, the hormones seemed to have a calming affect. Once a rapid-fire talker, Gray's conversation slowed a bit. Anxiety issues seemed to become less acute.

Gray's period eventually stopped, and a menopausal phase that included hot flashes set in. Though Gray's breasts were pretty small to begin with, he opted for a chest reconstruction and was surprised by the grief it caused. "Not to say I regret the decision, but I was like, whoa," he says. "Someone cut off part of my body."

When it was all over, Gray passed as a man completely.

Except for one small thing. Although the clit had grown to about half an inch, Gray has no penis. And he doesn't think he wants one. He says that his transition and gender identity has less to do with his own preferences, and more to do with how he is perceived by others.

If he could have lived in the world as a gay man who looked like a woman, he says he wouldn't have changed his gender. "God or whoever didn't make any mistake," he says. "I was supposed to be born a woman. It sucked, but it makes me who I am."


It's not unusual for those who choose to do sex work to have had troubled youths, but Gray says that his was textbook happy. "I was not abused mentally, physically, or sexually, at all," he says. "My mother is a saint. My father is MacGyver and a god."

But because they have a "healing relationship," Gray requested that no identifying information about his parents run in this story. They sent Gray and their other child, whom we'll call Mark, to Catholic school, where the nuns always embraced Stephanie and told her, "You could be a great nun someday." In addition to being a straight-A student, Stephanie played soccer and softball and seemed to always want to kick with the guys.

Steph "was always a tomboy," said Mark, a former vocalist in a touring Christian screamo band who now lives in China teaching English. When the men went hiking and took their shirts off, Steph did, too. When they played rough, Steph did, too. She had a fixation with male bonding, and seemed to idolize her father.

After Gray took a girlfriend, the siblings had long discussions about whether being gay was okay in the eyes of God, and Mark is still torn over it. But as far as the sibling relationship goes, something Mark dubbed "rays of love" prevailed. When he learned that his sister was going to become a man, that, too, was jarring, but he felt more prepared because of the lesbian thing. "That was almost an easing into this next step," he says. "Rays of love" over the sex change didn't come quite so easy with their parents, Mark remembers, but he leaves it at that.

To this day, Mark struggles with how to think about his brother's choices. Many people he knows — good people — tell him those choices are wrong. "But to react in a negative way is not Christlike behavior," he says. "It has caused me to think deeper into things," he says. "It has expanded my faith."

One thing Gray is not ready to explain to his brother — and therefore another failure in his desire to be fully known and accepted — is sex work.

28-yr-old FTM, look younger. 5'5", 130 lbs, lean muscled & high energy, HIV- & dd free, hairy w/ original plumbing, cock worshiping good Catholic boy sucker, swallower, piss bottom, loves to fuck to opera. you'll get more than you pay for. 415.265.6525.

This was a sex ad Gray could have used. But it was actually his bio for Formerly Known As, a recent art show at the Center for Sex and Culture with contributors who are sex workers. In their bios, the other entrants, who all seem to be writing memoirs, focused on artistic abilities and used creative photographs. But Gray juxtaposed the text above with an adorable picture of himself in the pool, wearing goggles and a giant smile.

Here's why. Gray worked as a hustler for about two years, and estimates that 40 percent of his clientele were college professors. There was one from Berkeley. One from Cal State East Bay. Some were retired and didn't say where they had worked. When not in the bedrooms of professors, though, Gray — who currently works at a college that he does not want named (another victory for societal norms, he laments) — says he's been judged harshly in academia for his edginess. He didn't feel like listing his academic credentials anymore. Instead, he decided to approach the bio as a piece of dramatic, yet accurate, performance art. "It's very much me," he says.

The idea of becoming a sex worker first occurred to Gray in Thailand, where some female sex worker friends had paid their way through college. Then, while back in San Francisco and undergoing his sex change, for which he would definitely need to make some money, he happened to read an essay by local sex worker and author Kirk Read in the anthology Nobody Passes. The essay is about Read's first two sex gigs, and how he had rearranged them in his mind to tell a more palatable story about sex work.

During Read's true first experience, he had snorted crystal meth, believing it to be coke, then sucked cock all night long in a dirty basement apartment, only to be shorted on payment. But instead of telling that story, he found himself reverting to his second appointment, in which he was paid in full and his client proclaimed him a healer.

This essay appealed very much to Gray's obsession with honesty, and ignited in him the desire to take "a beautiful risk" in defying conventional wisdom by becoming intimate with strangers. Sex work fascinated him, and he also liked the idea of being wanted so badly for his particular body that gay men were willing to pay.

So far, Gray says he hasn't gotten much grief over his vagina, which is surprising, considering gay men are often spooked by female anatomy. But when you consider that Gray's Craigslist ads were always upfront about his plumbing and that he announces his lack of a penis before he disrobes, it begins to make a little more sense. When he does get rejected, Gray feels terrible.

One night at Deco, men were strip-dancing, and some guy approached Gray and told him he should get up there and take it off. No way, Gray said. He didn't believe a vagina would go over well in a gay bar. But the guy kept pestering him to strip, and requesting a private show after, and finally Gray snapped.

"I don't think I'm what you're looking for," he told the guy.

"It's not like you're trans," the guy retorted. "You have an Adam's apple."

"Actually, I am," Gray fired back. "And that's my trachea."

The guy looked confused, so Gray took his hand and put it on his crotch. "I don't have a dick," he said. The guy stepped back, then bolted. From across the bar, a friend who saw what happened mouthed "I love you" to Gray. "I felt very protected," he said. "But that doesn't mean it doesn't hurt."

Gray is sensitive to criticism, even if it comes from a stranger. Luckily, in his sex work — which he says has provided him with meaningful experiences and a surplus of material for storytelling — his clients tend to shower him with compliments.

That's not all they shower on him. "A piss bottom," he explains earnestly, "is basically someone who likes to be peed on in various forms." Some even like to swallow it. Gray is into all things piss play.

He doesn't like to try to intellectualize that desire, because he feels it's very intuitive. Just something he likes to be subjected to. He's really into fluids, though, so if he had to guess at why he loves piss so much, he'd say it's because piss doesn't carry HIV.


The sex-positive movement in San Francisco is arguably the strongest in the nation, and although Prop. K, which would have decriminalized prostitution, didn't pass, there's a strong contingent here that touts the ability of sex work to improve lives.

Sex workers frequently claim that theirs is a job like any other, an exchange where two people get what they want. Some say it's even better than that, because they are offering intimacy to some extraordinarily lonely people. There's a word for that they use: healers.

Those same healers, however, will simultaneously admit that they sometimes opt out of sex work for personal reasons. Emotionally revitalizing a client can be emotionally draining, they say, and part of being able to keep the job under control is to know when to take a break.

In recent years, plenty of academics have come out in support of the idea that sex workers are healers and that their profession should be legalized, including Jeffrey T. Parsons, professor and chair of psychology at Hunter College, where he researches sexuality.

"There are psychologically well-adjusted sex workers out there," he said. It just depends how and why the sex work is done. For "the male escort of the 21st century" — who doesn't live in a brothel or have a pimp — Parsons doesn't see a problem: "He advertises. He screens his clients before they come over. He may very well negotiate what's going to happen ahead of time. He has a lot of agency in the work that he does."

Parsons would appear to be describing someone like Gray. But as much as Gray has enjoyed his sex work, there have also been times when he has experienced guilt and shame about it.

During a spiritual healing session of his own (the "hippy-dippy" kind, not a sex encounter), he realized that the image of one particular professor having sex with him had been chasing him for months, and he didn't like it. He realized he felt like a failure in connection with the sex work, which was why he was hiding it from friends and family members.

Comparing it to a fall from grace, he says he was no longer perfect or good in the eyes of others. He was, in fact, a criminal, and eventually he internalized that. But after recognizing that he was feeling guilty for no good reason, he says he was able to move past it. "What is so fucking wrong with being a sex worker?" he now demands to know.

While he may have emerged from his own guilt, Gray is still seeking the general approval that came so easily to his former female self. Sometimes that need, coupled with his tendency to take risks, can get him into trouble.

About two years ago, Gray was in the Castro at a client's home, and they were sitting on the couch, drinking beers and talking about death. The client had lost quite a few gay friends to AIDS in the '80s, and was himself HIV-positive. Gray had lost people to AIDS in Thailand. In bonding over their losses, "I became really attached to him," Gray says. In fact, he often became attached to clients, and sometimes had a hard time continuing to charge for sex he liked.

Gray wound up performing oral sex on the client on the couch. They then took a shower, where foreplay continued. The client pissed in Gray's mouth, then carried him to the bedroom. The naked men began rubbing their genitalia together, and Gray liked it very much. He felt a strong connection with this man.

Then something changed. Although there was no discussion, the client was seemingly making an attempt to penetrate him. Was he really going to do it? Gray felt paralyzed. He said nothing.

The client inserted his penis — without a condom — into Gray and had sex with him, which had the potential to expose him to HIV.

As an HIV-prevention counselor for the city of San Francisco, Gray obviously knew better. He knew he was supposed to speak up. But he couldn't. "You always think that when you are raped, you'll be like, 'Fuck you. Get off me,'" he says. "I was thinking, 'I have to do whatever this guy wants me to do, and then I'm out of here.' My body did me a favor, and I kinda floated out."

A couple of days later, a still-paralyzed Gray talked about what happened with a friend, who insisted the encounter had been rape. Gray determined that he needed a post-exposure prophylactic — a kind of morning-after pill that fights HIV contraction. He had a 72-hour window in which to do so.

On the third day, he broke down crying at work and had to explain to his boss that he believed he was raped, and might have been exposed to HIV. His boss — a queeny gay man — said, "Honey, this is serious," and sent Gray to a clinic, where he took an assortment of medications. "I puked a lot," he says. "It feels like shit."

Gray says he tested negative for HIV, and feels extremely lucky.

Afterward, he began to reevaluate his feelings about a lot of things, including HIV and sex work. He had always hated HIV, to the point where he wished it were a person, so he could punch it in the face. He once believed he wanted to have sex with someone who was HIV-positive without a condom as a way of standing up to it, as if to say "Fuck you." But after the incident and having to confront fears of actually contracting the disease, that fantasy seemed dangerous and stupid.

Although Gray continued doing sex work, he found himself feeling withdrawn.

"I stopped having sex for free," he says, and then quickly adds, "Even though sex is never free." He moved in with his mother in Anaheim, and worked as an HIV educator in a prison. He stopped talking about sex outside of his job, and for about six months he stopped having sex altogether. Most mornings, he swam laps, which became a kind of escape. He still swims almost every day, and also gives swim lessons to kids and the disabled. He also turned to faith: He is devoutly Catholic, and still goes to Holy Redeemer in the Castro every Sunday.

As for the client, Gray never talked to him again.

A couple of months ago, Gray — seeking some cash and maybe a thrill — placed another sex ad on Craigslist. That same client answered. Although Gray isn't sure whether the man knew whose ad he had responded to, he let it be, and says he wishes him well.

That shrugging off seems to be part of a larger pattern for Gray, who has a hard time thinking of anyone as his enemy, or standing up for himself. He says he's always felt close to vulnerability, and seems intent on allowing others to control his fate. That is, apparently, all a part of the beautiful risk.

"It was a healing experience to know this man," he says of his alleged rapist. "It was really interesting."


At the Center for Sex and Culture on the night of June 4, the packed house was baked in body heat. Just as it had been the previous night, San Francisco's first sex worker art performance, Formerly Known As, was sold out. Attendees sipped Tecate and brown-bagged wine, and those who didn't get a seat procured impromptu floor mats.

The first act involved two sex workers who had reworked biblical hymns into sex-work theme songs. Other standouts included an animation sequence by former professional diver Scott Upper revolving around a set of disembodied shark jaws and projected on a screen, and "The Pornographic Imagination," a doleful song by a Satanist in a sportcoat who called himself Christraper Sings.

With two acts left, emcee Kirk Read took the stage and thanked the audience. "This is like church, in a way," he said. "We're listening to each other."

"Hallelujah," someone cried.

"Our next performer," Read continued, was Stephen Gray. "He's a good Catholic boy ... and I believe he's a Fulbright scholar. I have very high hopes for this young man."

Gray took the stage and disrobed. When he was finished, he stood proudly as a man with no penis, and the audience burst into wild applause.

"This is a piece that I wrote about a man who was and still is a very special client," he said. "It's called 'Jimmy Inside Me.'"

Gray read confidently, sometimes shifting his weight from one foot to the other, and taking care not to go too fast or too slow. The story wasn't exactly straightforward, and although it documented the night he was penetrated by his HIV-positive client, it also wove in Gray's emotions, memories, and dreams, including his androgyny and his obsession with his father. "I will always be in between the masculine and the feminine, like a channel, where blood and sweat and cum once flowed," he read.

"There is a girl with me, in the air above my body," he continued. "A little girl boy. She cries and I hold her hand and run through the terrain of that place where this thing is, this thing I want to devour. That I want to battle in the heavens."

When the story was over, the audience broke into whoops and hollers in perhaps the strongest reaction of the night. Gray gathered up his clothes and walked back down the aisle naked, waving at the audience with the hand in which he carried his shoes. He disappeared into the darkness at the back of the room as Read reclaimed the stage. "God, the human body is such a miracle," he said. "Sometimes I feel like more people getting naked in public is the only way."

For the last act, a tall black performance artist stripped down and did unspeakable things with a corncob. Then the lights came on to signify the end of the show.

As people filed out of the room, many stopped to talk to Gray, congratulating him and shaking his hand. "Where could I read your stuff?" one guy asked.

Gray was composed and steady. And although the performance has its challenges — he was hot, and had a hard time standing still for so long — he felt good about it. "It's better than when I read it to myself," he says. "It's better than reading alone."

Peter Jamison contributed to the reporting for this story.

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