The Angolan writer José Luandino Vieira was imprisoned by the Portuguese colonial regime from 1962 to 1972, first in a Luanda prison, then, after 1964, in the Tarrafal concentration camp on the island of Santiago. Most of Vieira’s fiction was written during his incarceration. His early stories and short novels presented the mixing of the Portuguese and Kimbundu languages in the poor musseques (Black townships) around Luanda as a potentially revolutionary idiom capable of forging the future Angolan nation. The present article argues that, due to external pressures that accumulated in 1968, Vieira’s short novel João Vêncio: os seus amores marks a watershed in its more free-flowing linguistic experimentation and its explicit account, glossed over by earlier criticism, of a homosexual male relationship. Through textual analysis and the study of intertextual references to the work of João Guimarães Rosa and Ernest Hemingway, this article establishes João Vêncio: os seus amores as both a pioneering work of gay fiction in Angolan literature and the necessary prelude to the books that Vieira would write during his final years in Tarrafal.