Ceuta (Sabta in Arabic), one of a few territories in North Africa still held by Spain, from the 17th through early 20th centuries was a Spanish penal colony and then home to a military prison and today functions as a veritable fortress prison for African migrants trying to enter Europe. Given that until 1898 the insurgents against the Spanish crown from the Americas, among them major figures from Cuban and Peruvian history, were sentenced to confinement in Ceuta, this Spanish enclave has a nodal role in Spanish empire-building and the vestiges of the colonial enterprise that continue to operate till this day. In my paper I examine writings that either bear witness to Ceuta as a penal colony in which the Spanish crown tried to contain those seeking autonomy in its colonies in the Americas or protest Ceuta's condition as a Spanish possession (an "autonomous city" according to Spanish terminology). For 19th and early 20th century Latin American writers Ceuta was a site of exile and captivity and, once independence from Spain was achieved, calls for solidarity with North Africa as a Spanish colony gave way to Orientalist conceptions of North Africa as a savage Muslim threat to masculinity. Meanwhile, Moroccans writing after independence from France and Spain conceive of Ceuta itself as a captive [asi?ra] of Spain. Drawing on the lore surrounding women captives that arose in the encounter between Christians and Muslims around the Mediterranean and particularly in the Iberian Peninsula with the rise and fall of al-Andalus, Moroccan writers craft a sexualized version of Ceuta as a damsel in distress in their efforts to decry continued Spanish control of the area. Building upon recent studies that consider the role of confinement and exile in politics (Roniger, Green, and Yankelevich, 2014 and Khalili, 2012) and the established role of sexuality in colonial territorial possession (e.g., McClintock, 1995) I examine these works to understand the transhistorical, transcontinental colonial power dynamics that run through Ceuta and use sexuality to create and maintain North/South hierarchies. My analysis of these memoirs, plays, poems, and narratives exposes the enduring structures of power that both create and limit cultural and political alliances between the Arab world and Latin America.