This dissertation treats the study of the representation and construction of male images that subvert, transgress and deconstruct hegemonic models of masculinity. The selected literary works---influenced by poststructuralist, postmodern and feminist criticism and the socio-economic changes which have occurred in the last thirty years---challenge and contest the nature of patriarchal ideals of masculinity. Thus, aware of the artificiality of the concept of hegemonic masculinity, the male characters depicted in the selected four novels opt to embrace behaviors that defy the rules prescribed by society. In order to suspend gender binary relations, these male characters must create their own personal spaces in which they are free to behave and interact with others as they please. In Manuel Puig's The Kiss of the Spiderwoman (1975), the characters Molina and ValentIn defy oppression by setting their own gender roles in an Argentinean prison. Mario Vargas Llosa chooses the bedroom and the bathroom in In Praise of the Stepmother (1988) as places for don Rigoberto to explore his body and sexuality, which free him from his obscure public existence. In The Notebooks of Don Rigoberto (1997), a sequel to the previous novel, don Rigoberto uses his personal diaries as a transgressive tool to denounce gender inequalities, to develop his own theory of eroticism, and to explore his deepest sexual fantasies, which pose his absent wife, Lucrecia, as protagonist. Finally, the Cuba of the nineties, portrayed in Pedro Juan Gutierrez's El Rey de La Habana (1999), becomes the landscape of transgression and subversion, where its citizens, among them the protagonist Rey, have to exploit themselves and others in order to survive hunger and misery. Moral and physical corruption as well as violence become the symbols of this new hypermasculinity.