The paper examines the relationship between patterns of male prostitution and the changing definitions (and regulation) of homosexual behavior in the late nineteenth and early twentieth centuries. A series of problems is explored. First, an attempt is made to delineate the changing patterns of legal and ideological control in the nineteenth century. This leads to a discussion of the second problem, the ways in which the social and legal context dictated the close relationship between the homosexual subcultures and the cash nexus represented by the prostitution relationship. The third problem concerns the ambivalent nature of the "prostitution," the complex self-concepts that developed, and the factors inhibiting the development of a distinctive subculture of male prostitution. The differences between female and male prostitution are discussed. The paper concludes by underlining the ambivalence of "male prostitution".