William Shakespeare and Margaret Cavendish each published plays and poems focusing on the precarious implications and cultural enactments of female chastity in their time. Their lives and writing careers bookend a time when chastity's place in English politics, religion, and social life was perceived as crucial for women while also being challenged and radically redefined. This paper engages in period-specific definitions of virginity and chastity, and with modern scholarship on the same, to explore the historicity of chastity and how representations of self-enforced chastity create opportunities for female political power in certain fiction contexts. Through a comparison of the female protagonists of Measure for Measure and Assaulted and Pursued Chastity—Isabella and Travellia—I argue that both characters are able to assert and gain practical forms of power within their respective systems of government, and not just in spiritual or economic spheres.