Medieval Persian pornography constitutes one of the richest and unexplored subfields of Middle Eastern literatures. Oscillating between disturbingly demeaning invectives, explicit representations of intimate body parts, and titillating explorations of sexual desire, obscene poetry interacts with the mainstream genres of the Persian literary canon at multiple levels and through unexpected points of contact. Comparisons with the medieval pornographic traditions of the West have inspired scholars to conceive of Persian pornographic poems as “counter-texts” to the courtly lyric tradition (i.e., amatory qasidas, ghazals, etc.). Counter-textual readings enable us to reconsider the contextual power of obscene literature to explore the human body from perspectives that bridge the gap between courtly ideals of beauty and physical experiences of desire. By relying on counter-textual affinities between courtly lyricism and obscene poetry, this paper addresses the problem of gender in Persian literary pornography and its connection with the representation of the human body beyond sexual binaries. While Persian ghazals tend to un-gender the body of their idealized objects of desire (even when specific physical traits seem to suggest same-sex interactions among men), pornographic counter-texts dwell extensively on gender-specific intimate body parts and clothing. When analyzed within the same literary canon, juxtapositions between ungendered idealized representations and gendered depictions of the beloved’s body open new windows into the fluidity with which medieval Persian authors imagined physical expressions of desire. Insights based on the theory of counter-textuality and contemporary paradigms emerging from the field of gender studies will be applied to the analysis of “trans-gendering” amatory ghazals by the medieval princess Jahan Malik Khatun (fl. 14th c. CE) and short obscene texts by Suzani Samarqandi (12th c.), Sa‘di Shirazi (13th c.), and ‘Ubayd Zakani (14th c.). This critically informed philological approach will show how forays into the neglected space of literary pornography can help us make better sense of the complexity of shifting gender representations in classical Persian poetry.