Male sex work and male homosexuality have traditionally not been regulated as distinct issues in the same way as female sex work and sexuality. This chapter explores the reasons for this differential treatment and the gendered and (hetero)sexist stance on sex work. It exposes the legal–conceptual blurring of male homosexuality and male sex work and argues that the primary concern of the law has historically been combatting male homosexuality rather than male sex work in itself. It does this primarily by examining the laws created and applied to male homosexuality and male sex work in the United Kingdom and in New South Wales, Australia, from the late nineteenth century onwards. Following a historical discussion, the chapter examines the practical and conceptual reasons for the ongoing hetero(sexist) approach to sex work and explores whether the changes that new technologies have brought about to the sex work industry are likely to cause a shift in this approach.