At the centre of the clerical vocation was the conundrum of balancing the clergy’s commitment to chastity with the many aspects of their professional training and responsibilities that either tacitly or overtly concerned sex. On a pedagogical level, there were pagan authors, like the sexually savvy Ovid, who were at the cornerstone of the acquisition of letters. But biblical tradition, theology, and ascetical literature also treated sexuality and sexual temptation very explicitly. Such concerns loom even larger on a practical level. The clergy had always assumed the responsibility of monitoring lay mortality. But the sexually explicit nature of their pastoral obligations would increase exponentially when the Church established a hegemony over marriage and made auricular confession mandatory for the laity in the high Middle Ages. This chapter provides an overview of the many different kinds of sources that lend insight into this, at times, fraught aspect of the clerical vocation.