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.

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.'"

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.

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."

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