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Bill’s New Frock (1989) and Marvin Redpost: Is He a Girl? (1993) each tell of a boy who spends a short time living life as a female. This article reads these two chapter books in the light of the debates about the relationship between sex and gender that took place both within feminism and in the nascent queer and transgender movements in the years leading up to the early 1990s. It suggests some ways in which these apparently similar texts embody important ideological tensions and disparities, reflecting the wider gender politics of the period.