This chapter explores how anxieties regarding women’s ability to feign virtue contribute to the idea of female shamefastness as an enemy to be besieged and conquered by desiring men. This adversarial dynamic emerges clearly in personification allegories of varying scale and complexity, which present Shame as a stubborn adversary who must be defeated by Love by any means necessary, including by force. The chapter begins by considering the origins of the enmity between desire and shamefastness in the nature of personification allegory, focusing in particular on Prudentius’s treatment of lust (Sodomita Libido) and modesty (Pudicitia) in his Psychomachia. It then examines how personification allegories such as the medieval French Roman de la rose and its Middle English translation draw on anti-feminist tradition in order to explicitly establish female shamefastness as an obstacle or opponent to be overcome by male desire. The chapter’s final section turns to Lydgate’s discussion of female shamefastness in the Troy Book, and demonstrates how his depiction of Medea’s ‘staged’ shamefastness and his allegorization of her subsequent emotional turmoil articulate the anti-feminist logic that puts female honour at risk.