HIV/AIDS rates in South Africa are among the highest in the world. Although the immediate transmission of HIV/AIDS takes place biologically, there are a number of other parameters which influence and in turn are affected by the disease. Part One of “Illness as Metaphor” gives an overview of the historical, socio-political, economic and cultural factors surrounding the HIV/AIDS epidemic. A larger section deals with the disastrous handling of the epidemic during the Mbeki government between 1998 and 2003 as well as the silence around the disease. Part Two investigates how the entanglement of these aspects and their impact on society and the individual are represented aesthetically in a small selection of contemporary South African literature dealing with the HIV/AIDS issue. The novels and plays chosen for this work are Sindiwe Magona’s Beauty’s Gift, and Kgebetli Moele’s The Book of the Dead, Sindiwe Magona’s only play Vukani!, and Mike van Graan’s Iago’s Last Dance. The texts have in common that they circle around the most disturbing phenomenon that men infect women with the deadly virus on purpose.