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For high-school seniors like Skylar—who live in prosperous suburbs, have doting parents, attend good schools, and get excellent grades while studding their transcripts with extracurricular activities—the hardest part of the college application is often the personal essay. This was not a problem for Skylar.

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Skylar is a boy, but he was born a girl, and lived as one until the age of fourteen. Skylar would put it differently: At sixteen, he started getting testosterone injections every other week; just before he turned seventeen, he had a double mastectomy. Skylar is an F. Skylar lives in an affluent, wooded town near New Haven, a liberal enclave where nobody seriously challenged his decision to change gender. Some of his peers even expressed a certain envy.

About a Boy

This will be your ticket into your dream school. Many trans kids have a very hard time.

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They are bullied at school, rejected by their families, and consigned to marginal—even desperate—lives. Teen-agers who identify as transgender appear to be at higher risk for depression and suicide.

Many therapists have begun to speak of even very young children as transgender a category that few clinicians of past generations would have applied to them.

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