This chapter focuses on the complex intersections between the sexual rights and anti-apartheid movements. It discusses several local and transnational cultural flows and shows how they were renegotiated within the liberation struggle in the 1970s and 1980s, and during the transitional decade of the 1990s, to produce a particularly localised sexual politics. In this period, sexual rights in South Africa would come into dialogue with the activist and ideological networks of the anti-apartheid movement. Rather than conceptualising human rights as universal, this chapter traces how twentieth-century human rights is a contested ideological form that is inhabited differently in different contexts. With a particular emphasis on activist Simon Nkoli, this chapter examines how the anti-apartheid movement’s initial homophobia gives way to a more inclusive recognition of sexual rights as constitutive of an indivisible human rights project. This chapter engages closely with three cultural texts that offer snapshots of different moments in this history, namely Gerald Kraak novel Ice in the Lungs (2006), Robert Colman’s stage drama Your Loving Simon (2003), and Beverley Ditsie and Nicky Newman’s documentary film Simon & I (2002).