The Church prefers to think that all sinners can be saved. Hagiography that leads to this moral has been popular among creative writers, and the more accentuated the sin, and the more dramatic the change undergone by the repentant sinner, the more satisfactory the example is. This is the official reason for the pleasure taken in the genre of the saintly former prostitute, or as Andrew Beresford calls them, the holy harlot. The harlotry and the holiness are not simultaneous; the repentant woman suffers for a long time before becoming a candidate for saintliness. Five such cases feature in the literature of medieval Castile: Thaïs, Pelagia, Mary Magdalene, Mary the Egyptian and yet a third Mary, the ‘niece of Abraham’. The stories differ considerably one from another, so they are not the result of a common template (or ‘common ethos’, in Beresford's terminology). Only Thaïs and Pelagia are discussed at length here, with two Castilian versions of the Life of the former and three of the latter being critically edited. In an attempt to compromise between the desires of the philologist and those of the more general reader, sufficient emendations have been made to annoy the former without providing an easy read for the latter. The narratives are recounted and analysed in considerable detail. Those of Thaïs and Pelagia have in common their Greek origins, and are called ‘legends’ from the start, without any attempt to decide if they contain a grain of truth. The prostitute Thaïs is ‘saved’ by the cleric Paphnutius who tricks her by asking her to make love with him in public; she refuses, and then he causes her to repent by pointing out that God sees what she is doing even in private. Pelagia is ‘saved’ by Nonnus, a cleric who falls for her and exclaims that her body is more beautiful than his soul; she is, however, so taken by a sermon of his that he is able to baptise her. Both women go on to live the most ascetic of lives in cells in the harshest of deserts, thereby acquiring beauty and grace in their souls as they lose it in their bodies. Jacobus De Voragine included expanded Latin versions in the Legenda aurea. The three fifteenth-century Castilian manuscript versions of Thaïs's tale derive from that; two similar versions which call her ‘Tarsis’ rework the Latin to create a more vivid impact, but neither fills more than two printed pages in this edition. There are four Castilian manuscripts that include the Pelagia story, only two of which coincide; the three tales are here called the Ystoria, the Vida and the Vida y conversión (de Santa Pelagia). This third one is considerably longer (nearly eight pages) and ‘only tangentially’ related to the Legenda aurea. Andrew Beresford considers carefully but speculatively the development of attitudes towards sexual sin and salvation over the thousand years in which these tales evolved, discussing the different social roles of prostitutes through modern gendered sociological analyses; on the other hand the equally modern view which sees such tales as being tasteless manifestations of both a hatred of beauty and pleasure and a delight in suffering and pain, recoiling from them as symptoms of mere bigotry and sadistic cruelty, is not considered at all.