This paper examines the trajectories of two characters in Laura Antillano's short story, "Tuna de mar" (1991), as they navigate interrelated systems of power and attempt to position themselves closer to, or further away from, the margins. Set in the late eighteenth century, the tale features a female protagonist who escapes prostitution and joins a pirate fraternity disguised as a man. The male narrator relates her story with an uneven hand, acknowledging her accomplishments while suppressing her voice and perspective, despite having gone through a gender shift of his own. My analysis will reveal the ways in which the protagonist and the narrator rebel against and are reinscribed within hegemonic power structures. I will further analyze the layering of different experiences of marginalization within the story, which provides a context in which to discuss the interdependent nature of colonialism and patriarchy within the history of Maracaibo (Venezuela). Finally, I stress the relevance of this story for considering contemporary Latin American and Caribbean realities, including the marginalization and displacement of sex workers, the gendering of power, and the use of drag as a subversive strategy to undermine global economic as well as patriarchal power structures.