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The purpose of this study is to centralize, into women's history, the marginalized historical voices of women activists working in sexualized labor (and/or those using sexualized economic strategies). This thesis situates the work of Josie Washburn, a former madam who turned self advocate in 1907, squarely within the Progressive Era debate on prostitution, By centralizing women's voices of sexualized lahor, it provides a means to track the long-term evolution of the intersections between women's sexualized labor choices, traditional labor choices, self-advocacy, popular media, and social/political movements on behalf of women. This study asserts that a majority Progressive Era working women utilized sexualized labor strategies to survive the substandard wages of paid employment. Working women bartered their time and bodies in numerous different ways that included dating for luxuries (such as shoes) to professional prostitute in brothels. Thus, the history of sexual labor (clandestine to professional) is central to the grand narrative of women's history. Furthermore, this study compares the challenges and issues faced by Progressive Era prostitutes to that of sex workers during the 19508 - 1990s. The comparison reveals that the women who formed the sex workers movement of the 1980s confronted problems remarkably similar to those faced by Josie Washburn in the late nineteenth century.