This chapter focuses on the lives and literary production of two Puerto Rican female writers, Carmen María Colón Pellot, the mulatto schoolteacher, social worker, poet, and author of Ámbar mulato (1938) and Clara Lair, aka, María de las Mercedes Negrón Muňoz, the white-Creole patrician literary figure and author of Arras de cristal (1937). Both explored what Toni Morrison described as “the fears and desires that reside in the writerly conscious” from explicitly opposite racial perspectives in 1930s Puerto Rico. Discursive acts provide elements of unconscious autobiography and thus their verses make possible an understanding of what drew these two women to write their respective poetry collections. Which, in turn, enables an analysis of the ways that Colón Pellot and Lair positioned themselves within the national discussion taking place among Puerto Ricans (in this case, in the Island) on foundational issues such as Puerto Rican identity, ‘womanhood,’ and ‘race’ within the debate unfolding amidst overwhelmingly masculinist and racist, white-Creole parameters canonically exemplified by the elite local Revista Índice in 1929.