Freewheeling sexuality and gender experimentation defined the social and moral landscape of 1890s San Francisco. Middle class whites crafting titillating narratives on topics such as high divorce rates, mannish women, and extramarital sex centered Chinese and Japanese immigrants in particular. Amy Sueyoshi draws on everything from newspapers to felony case files to oral histories in order to examine how whites' pursuit of gender and sexual fulfillment gave rise to racial caricatures. As she reveals, white reporters, writers, artists, and others conflated Chinese and Japanese, previously seen as two races, into one. There emerged the Oriental—a single pan-Asian American stereotype weighted with sexual and gender meaning. Sueyoshi bridges feminist, queer, and ethnic studies to show how the white quest to forge new frontiers in gender and sexual freedom reinforced—and spawned—racial inequality through the ever evolving Oriental. Informed and fascinating, Discriminating Sex reconsiders the origins and expression of racial stereotyping in an American city.