This chapter traces the inflection of various religio-cultural traditions and customs of erotic love and sex and ordering of sexual acts in sixteenth-century Istanbul as defined by literary and documentary sources. With its diverse population and as the seat of the Ottoman dynasty, Istanbul was one of the most crowded and diverse cities of the sixteenth century. It witnessed the formation of an elite class that distinguished itself from the majority of the urban population through ideological othering strategies and the establishment of law codes to order and rule the diverse communities in the city. Literary works that focused on the city and documents, including law codes and court records, reflect conflicting views on sexual relations: while chaste love among members of the elite was idealized in romances and sexual acts were criticized in satirical works, documents reflected the ways sexual acts and desires were regulated, controlled, and punished.