This chapter interprets El mundo alucinante (1965), the second novel of the Cuban writer Reinaldo Arenas, as a diachronic narrative that intertwines Arenas’ struggles in Revolutionary Cuba with those of the contentious republican priest Servando Teresa de Mier in New Spain, as both pursue personal and political freedom and self-determination. The author argues that El mundo alucinante unveils a literary coding between masculinity and migration that, within the context of Arenas, allegorically challenges the established ideas of manhood and brotherhood in Revolutionary Cuba. Servando’s multiple displacements and embodiments in the novel are interpreted as “trans-migrations” that enable Arenas to defy conventional notions of manhood in 1960s Cuba. Furthermore, the novel is read as a site for Arenas, as homosexual, dissident and later exiled writer, to assert his place within an aesthetic avant-garde that challenges the authority of the revolutionary political vanguard of the Cuban Revolution.