M.A. / The post-apartheid period has seen growing literary interest in issues of gender and sexuality. This dissertation reads literature as a type of cultural history and engages critically with the discursive and epistemological role of fiction within a broader palimpsest of discourses, theories and nomenclatures relating to sexuality. It maps the limitations of existing epistemological hierarchies and argues for the recognition of fiction as an ephemeral and complementary archive of same-sex subjectivities. While fiction can construct and shift signifying regimes, it also engages with the complexities and nuances of individual subjectivities as well as the affective elements of narratives in interesting and important ways. Focussing particularly on K. Sello Duiker’s The Quiet Violence of Dreams (2001), Gerald Kraak’s Ice in the Lungs (2006), and Mark Behr’s Kings of the Water (2009), this dissertation examines the ways in which representations of non-heteronormative sexualities impact on post-transitional literary culture in South Africa. Transition-era texts and discourses tend to serve particular political imperatives that demand the politicisation of identities. This dissertation destabilises the existing taxonomies of sexual identities and foregrounds the fluidity of both sexual desire and individual subjectivities. Furthermore, this dissertation interrogates the signifying regimes and discursive practices with which same-sex intimacies between men are represented. In addition, it interrogates the prevailing frameworks for the study of masculinities and shows how the novels under consideration illustrate alternative ways of conceptualising gender performativity. While there are of course a multiplicity of masculinities, through a close reading of the novels I argue that the performativity of masculinities is produced by the indeterminate, though undeniable, intersections between cultural gender norms and individual agency. This dissertation’s analysis of gender representations identifies masculinities as the site for the interrogation of myriad historical and cultural discourses including those relating to the South African Defence Force, the anti-apartheid movement and post-apartheid Cape Town. Accordingly, I argue that the three post-transitional novels under consideration resist the politics of collective mobilisation and undermine ideologically-sanctioned ‘official’ histories. As both a literary and a cultural history, this dissertation engages not only with the literariness of the novels but also with how they contribute to a broader cultural history of same-sex male subjectivities in South Africa.