Shortly after the execution of Charles I and the establishment of the new Free State, authors sympathetic to the republican regime began developing increasingly lurid tales not simply about the dead king, but also about his extended family. It highlighted the Stuarts’ political misrule and religious indifference, but it also advanced a remarkably detailed, and eye-catching, account of their sexual depravity. Charles preyed on court ladies; James was addicted to lithe young men; Anne of Denmark – not surprisingly – had a marked preference for Nordic males; Mary Queen and Scots was sexually voracious, just as her mother Mary of Guise had been. All paid a steep religious and political price for their unchecked libidos, for by 1649, God – these authors all argued – had marked the entire family was destruction. This systematic denunciation of the Stuarts in the early 1650s, furthermore, corresponded almost exactly with the Third Civil War in which the Free State faced off against the unholy alliance of Charles II and the Scottish Covenanters. The direct political relationship between the emerging Black Legend and the Republic becomes even clearer since it was partly written and almost certainly coordinated by John Milton, Marchmont Nedham and their protégés. This chapter examines this development of the rhetoric of an Accursed Family in the early 1650s, and in the process, it underscores the utility of Ann Hughes’ work of printed culture and sexual politics during the English Revolution.