This essay describes how women’s genitalia came to be symbolized in the hybrid beast-woman form of the “octopussy,” tracking its origins to Victor Hugo’s novel, Les travailleurs de la mer (1866). Highlighting the centrality and sensationalism of an octopus attack on a sailor, the essay argues that Hugo’s highly gendered language helped transform the episode from a man/animal encounter into the ravishing of the male protagonist by an assertive female. This reading is supported by an examination of the terrified reactions of contemporary readers and by looking at the cultural appropriation of the octopus following the novel’s publication. The French word for octopus came to denote a sexually assertive and economically ambitious woman who traded upon her erotic charms. The emergence of this social type derived its aesthetic power from channeling contemporary anxieties tied to gender normativity, class distinction, racial purity, and other sacred boundaries. This fretful symbolization of autonomous female anatomy remains with us, the author notes, in such popular images as the octopussy of James Bond notoriety and the evil Ursula in Disney’s Little Mermaid, a figure that catalyzes fears related to the rise of capitalism: the orifice the octopussy wields so shamelessly comes to stand for the always already penetrated subjectivity of liberal economics and politics.