It was late on a rainy fall day, and a college freshman named Rey was showing me the new tattoo on his arm. It commemorated his 500-mile hike through Europe the previous summer, which happened also to be, he said, the last time he was happy. We sat together for a while in his room talking, his tattoo of a piece with his spiky brown hair, oversize tribal earrings and very baggy jeans. He showed me a photo of himself and his girlfriend kissing, pointed out his small drum kit, a bass guitar that lay next to his rumpled clothes and towels and empty bottles of green tea, one full of dried flowers, and the ink self-portraits and drawings of nudes that he had tacked to the walls. Thick jasmine incense competed with his cigarette smoke. He changed the music on his laptop with the melancholy, slightly startled air of a college boy on his own for the first time.
Rey’s story, though, had some unusual dimensions. The elite college he began attending last year in New York City, with its academically competitive. fresh-faced students, happened to be a women’s school, Barnard. That’s because when Rey first entered the freshman class, he was a woman.
Rey, who asked that neither his last name nor his given name be used to protect his and his family’s privacy, grew up in Chappaqua, the affluent Westchester suburb that is home to the Clintons, and had a relatively ordinary, middle-class Jewish childhood. Rey, as he now calls himself, loved his younger brother, his parents were together and he was a good student, excelling in English and history. But he always had the distinct feeling that he wasn’t the sex he was supposed to be. As a kid, he was often mistaken for a boy, which was “mostly cool,” Rey said. “When I was 5, I told my parents not to correct people when strangers thought I was a boy. I was never a girl, really — I questioned my own gender, and other people also questioned my gender for me.” When Rey entered puberty, he felt the loss of the “tomboy” sobriquet acutely.
“My body changed in freshman year of high school, and it made me depressed,” Rey said. That year, he started to wonder whether he was really meant to become a woman. His friends in high school were almost all skater boys and musicians, and he related to them as if he were one of them. He began to define himself as “omnisexual,” although he was mostly attracted to women.
Long article on transmen at women's colleges:
http://www.nytimes.com/2008/03/16/magazine/16students-t.html?ref=magazine 
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