The medieval quest for the Holy Grail could only be achieved by a very special man. He should be a virgin, utterly pure, and, according to certain of the early versions of the Grail legend, have a rather unusual gender profile: he may (in short) be castrated. The contextual correspondence between the representations of Perceval's ‘virgin gender’ in the early Grail cycles and the ‘spiritual eunuchs’ of the early Christian ascetic movement coalesce in sexual wounds. In both of these social contexts, perfect purity is valorized as a transformative grace which renders humans angelic; in both contexts the cultivation of purity represents direct action by the individual to mitigate the effects of the fall and loss of Eden which precipitated humanity into sexual desire. The literary milieu in which the Grail cycles took shape was infused with the idealization of virginity which characterized early Christian society, and immersed in hagiographic narratives which extolled the virtues of virgins. But one particularly pertinent dynamic linked the two environments: both dissect masculinity, teasing out a type of manhood in which sexual purity could be expressed. In medieval Europe, the eleventh-century Gregorian reforms required celibacy of the priesthood, and saw the development of the concept of virginity as a philosophical ideal as well as a religious principle. Both of these factors prompted a renewed interest in conceptualizing a ‘non-sexual’ man.