This chapter examines Cuban fiction about slavery emerging in the 1830s–1840s: Petrona y Rosalía (1838) by Félix Tanco y Bosmeniel; Francisco, el ingenio o las delicias del campo (1838–1839) by Anselmo Suárez y Romero; the short story “Cecilia Valdés” (1839) by Cirilo Villaverde (1812–1894), who later developed it into the novel Cecilia Valdés o La Loma del Ángel (1882); Autobiografía de un esclavo (1840) by Juan Francisco Manzano; and Sab (1841) by Gertrudis Gómez de Avellaneda. The chapter contextualizes the analysis in tensions between the demands for labor and “ad hoc moral alibis” characterizing Plantation America, particularly the improvised concepts of racial differentiation – Blackness and Black-and-white miscegenation – typifying responses to these tensions. The analysis of this literature as speculative writing that looks simultaneously toward the past and future links it to the sometimes improvisational and speculative nature of the new plantation-based societies, which were themselves entangled between speculative finance capital and moral reflections on freedom, and to the intensified anxieties about Cuba’s racialized future generated by the 1841 demographic census.