The history of queer and trans Puerto Rican and Diasporican literature is complex. Its relationship to American literature is fraught with issues of colonialism and linguistic exclusion. Careful analysis of a wide-ranging corpus from the late 19th and early 20th centuries by Alejandro Tapia y Rivera (1882), José de Diego Padró (1924), and Pedro Caballero (1931), reveals a longstanding interest in queer and trans experience in works written in Spanish in Puerto Rico and New York. The massive social transformations of the 1960s and 1970s led to the explosion of critical voices such as those of Luis Rafael Sánchez, Manuel Ramos Otero, and Luz María Umpierre. Their pioneering texts, and the complex writing of Nuyorican authors in English, opened the way for late 1990s and early 2000s authors such as Ángel Lozada and Mayra Santos-Febres, for the eventual creation of collectives such as Homoerótica in 2009, and for the widespread acclaim of writers such as Luis Negrón, Yolanda Arroyo Pizarro, Justin Torres, and Raquel Salas Rivera. “Queerness,” as such, and its Spanish-language variant “cuir,” have been spaces of possibility for Boricua expression for more than one hundred forty years.