This chapter contends that Manto’s trials signify a paradoxical sociopolitical context when it came to questions of women and sexuality: middle-class women became more visible in public and more highly educated in the formal sense, but there was also a shift in expressions of sexuality. This chapter argues that a complex and critical reassessment of Manto’s ethical self-fashioning through an examination of official documents, literary materials, and debates within progressive literary circles over representations of sexuality, enhances an understanding of the larger cultural and political developments of a turbulent period when it comes to the politics of sexuality. Finally, moral discourses, particularly around sexuality, were also prevalent within progressive, communist, and socialist intellectual circles as well, giving rise to hegemonic definitions and distinctions about who constituted the ideal literary progressive.