Through a close reading, this article explores a few aspects of gendered dissent in Li Ang’s story, “The Devil in a Chastity Belt,” which reveals the ambivalence and irony of a woman’s participation in the Taiwanese opposition movement. Instead of writing a stereotypical work of political fiction for the opposition movement that she supports, Li Ang interrogates the problematic intersection of gender and politics, while reclaiming some of the neglected aspects of oppositional history. While recognizing the inevitability of historical contingency, she nevertheless questions the politically-motivated choice of asceticism, heroism, and sacrifice over individual and familial well-being. Li juxtaposes seemingly trivial and disorderly details of ordinary life against the apparently important and grandiose arena of national politics, creating tension through their interaction and contention. She employs images—including the Devil, the female body, and sensory feelings—to perform gendered dissent. While the lyrical and trivial discourse gradually disrupts the political and didactic, the story’s open-ended conclusion inspires complex interpretations of the enigmatic symbol: the Devil wearing a chastity belt.