This thesis examines how Antes que anochezca (1992), the memoir of Reinaldo Arenas, functions as a literary act of resistance against the persecution of gay individuals in Cuba, particularly in relation to the heteronormative, authoritarian masculinity promoted by Fidel Castro’s regime during the Cuban Revolution. It explores how the memoir frames exile as both a political and sexual experience that often transcends physical displacement, and analyzes how these intertwined dimensions contribute to the construction of what I conceptualize as an intercultural model of gay masculinity. This model destabilizes both the ideals of the Cuban Revolution and dominant Western conceptions of gay identity. The significance of this inquiry lies in its focus on the intersection of sexuality, exile, and masculinity within a context of political repression, expanding the understanding of diaspora to include dislocation from national identity; even when that exile remains internal, enforced through state restrictions on movement and expression. In an era where sexual rights and expressions remain contested globally, examining historical instances of state-sponsored homophobia, particularly in communist revolutions often idealized by the West, provides crucial insight into the politics of gender and identity. Methodologically, this study employs queer theory, particularly the frameworks of Raewyn Connell’s hegemonic masculinity, Judith Butler’s gender performativity, and José Esteban Muñoz’s disidentification, to offer a queer reading of Arenas’s text. The findings show that his memoir contests both Cuban and Western paradigms of masculinity by narrating a disidentificatory space of gay survival, critique, and self-construction in exile. By foregrounding gay identity and intercultural translation, this thesis fills a gap in existing scholarship on Arenas. Future research could extend this framework to comparative studies of other gay diasporic authors from authoritarian regimes. Finally, this thesis reclaims the Caribbean homophobic slur pájaro as an empowering, reappropriative term that subverts and challenges antigay discourse.