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This doctoral dissertation focuses on a corpus of seventy-three prose letters from the Imperial period, titled Erotic Letters and attributed to Philostratus. In this letter collection, different anonymous letter writers address male and female recipients who are mostly anonymous. I contextualize the Philostratean erotic discourse in terms of Greek Imperial literature and the rhetorical culture of the Second Sophistic. Unlike the letter corpora of Aelian and Alciphron, the Philostratean Letters take a strong interest in ancient pederasty. Furthermore, the ancient Greek novel provides a fruitful comparison for the study of this particular letter corpus. The Philostratean erotic discourse employs a series of etiquettes and erotic labels which trace back to earlier (classical or Hellenistic) periods of Greek literary history. In this sense, the Philostratean Erotic Letters situate themselves in a long-standing Greek erotic tradition and draw from the prestigious classical past. In the context of individual Philostratean letters, pederastic motifs are often employed in heterosexual narratives and subvert the expected erotic discourse. Heterosexual motifs (e.g. feet) are also employed in pederastic contexts thus creating a literary discourse, according to which there are all kinds of erotic possibilities and literary scenarios. The Letters construct the identities of the senders and the receivers as the Greek pepaideumenoi of the Imperial period. In this context, the erotic experience emphasizes the idea of literary and cultural paideia as being sexually stimulating. In the end, paideia is deemed worthier than actual sex. In all these respects, the letter corpus of the Philostratean Erotic Letters presents the reader with a unique and open-ended literary discourse, which equally juxtaposes different representations of erotic desire.