This dissertation offers an analysis of the recurring trope of female masochism in Central European literary postmodernism. It investigates five foundational novels, from both sides of the Iron Curtain, written between 1961 and 1986: Milan Kundera’s The Unbearable Lightness of Being, Elfriede Jelinek’s The Piano Teacher, Peter Handke’s A Sorrow Beyond Dreams and Repetition, and Stanisław Lem’s Solaris. The dissertation argues that these texts deploy representations of female masochism in order to frame the relationship between culture and subject-building, against the background of the region’s borderland status within the cognitive map created by the Cold War. Despite the fact that masochism as a concept hails from Central European, and despite the popularity of masochistic tropes in Central European postmodernism (1960 and 1980), the theoretical debate on masochism rarely focuses on this literary geography. The dissertation offers two explanations for this critical lacuna: the invisibility of female masochism within the theoretical debate on masochism; and the difficulty of defining Cold War Central Europe due to its semiperipheral position.