The Milesian tale originates in ancient Greek and Roman literature. According to most authorities, it is a short story, fable, or folktale featuring love and adventure, usually being erotic and titillating. M. C. Howatson, in The Oxford Companion to Classical Literature (1989), voices the traditional view that it is the source "of such medieval collections of tales as the Gesta Romanorum, the Decameron of Boccaccio, and the Heptameron of Marguerite of Navarre."But Gottskálk Jensson of the University of Copenhagen, Denmark, offers a dissenting view or corrective, arguing that the original Milesian tale wasThis resulted in "a complicated narrative fabric: a travelogue carried by a main narrator with numerous subordinate tales carried by subordinate narrative voices." The best complete example of this would be Apuleius' The Golden Ass, a Roman novel written in the 2nd century of the Common Era. Apuleius introduces his novel with the words "At ego tibi sermone isto Milesio varias fabulas conseram" ("But let me join together different stories in that Milesian style") , which suggests that it isn't each story that is a Milesian tale but rather the entire joined-together collection. The idea of the Milesian tale also served as a model for the episodic narratives strung together in Petronius' Satyricon.

In any case, the name Milesian tale originates from the Milesiaka of Aristides of Miletus (Greek: Ἀριστείδης ὁ Μιλήσιος; fl. 2nd century BCE), who was a writer of shameless and amusing tales with some salacious content and unexpected plot twists. Aristides set his tales in Miletus, which had a reputation for a luxurious, easy-going lifestyle, akin to that of Sybaris in Magna Graecia; there is no reason to think that he was in any sense "of" Miletus himself.

Later, in the 1st century BCE, the serious-minded historian Lucius Cornelius Sisenna for an intellectual relaxation translated Aristides into Latin under the title Milesiae fabulae (Milesian Fables), and the term "Milesian tale" gained currency in the ancient world. Milesian tales gained a reputation for ribaldry: Ovid, in Tristia, contrasts the boldness of Aristides and others with his own Ars Amatoria, for which he was punished by exile. In the dialogue on the kinds of love, Erotes, Lucian of Samosata—if in fact he was the author—praised Aristides in passing, saying that after a day of listening to erotic stories he felt like Aristides, "that enchanting spinner of bawdy yarns." This suggests that the lost Milesiaka had for its framing device Aristides himself, retelling what he had been hearing of the goings-on at Miletus.

Plutarch, in his Life of Crassus, tells us that after the defeat of Carrhae in 53 BCE, some Milesian fables were found in the baggage of the Parthians' Roman prisoners.

Though the idea of the Milesian tale served as a model for the episodic narratives strung together in Petronius' Satyricon and The Golden Ass of Lucius Apuleius (2nd century CE), neither Aristides' Greek text nor the Latin translation survived the centuries of literate disapproval of such disgraceful secular hijinks, written with verve and panache, essential elements of the style. The lengthiest survivor from this literature is the tale of Cupid and Psyche, found in Apuleius, which Sir Richard Burton observed, "makes us deeply regret the disappearance of the others."Aristidean saucy and disreputable heroes and spicy, fast-paced anecdote resurfaced in the medieval fabliaux. Chaucer's The Miller's Tale is in Aristides' tradition, as are some of the saltier tales in Boccaccio's Decameron or the Heptameron of Margaret of Angoulême.