This chapter discusses how sexuality was used in political critique in late medieval Europe. In the Middle Ages the union of the king and the queen symbolized the social contract, and the royal marriage represented the bond between the king and his subjects. Negative descriptions of a royal marriage could therefore be used to signal discontent with a king’s reign. The chapter analyses a number of late medieval texts in order to expose reoccurring critical discourses that built on perceptions of gender and sexuality. We argue that sexual matters were used deliberately to highlight fundamental shortcomings in how a country was governed. A king’s inability to be sexually active indicated a lack of masculine authority. Kingly masculinity and dominance were closely linked and an effeminate king was an unthinkable proposition. In addition, since the king and queen were regarded as a unit, his behaviour impacted how she was judged. If the king was believed to lack masculine dominance and to be unable to control his wife, this could unleash the dangerous power that lay within queenship itself. The queen could be become unruly and adulterous. The incapable king and his unruly queen represented a dysfunctional rulership and failed regency.