This article explores the relationship between skepticism and sexual nonconformity in Italy from the sixteenth to the eighteenth century. In the inquisitorial cases under examination, the praise of sexual freedom was supported by a heretical re-reading of the myth of the Fall from Grace. The criticism of religious deception is the link between sexual freedom and skepticism: these dissenters accused the elites of enforcing a morality based on a reward in the afterlife to keep people under control. Although these ideas have been mostly associated with seventeenth-century erudite libertines, this research shows them emerging almost a century before, in cross-class environments where forbidden books circulated widely. The article will explore how the written word was creatively re-appropriated in these composite social contexts, analyzing the influence of a Mediterranean tradition of radical doubt that cut across the boundaries dividing the three Abrahamic faiths. In particular, it will focus on the cultural exchanges between Christianity and Islam.