Among sixteenth-century Istanbul’s many social, economic, and political changes, the city saw a marked shift in how the state and society perceived and managed prostitution. Waves of migration had brought people from rural areas to this imperial capital for employment and access to resources. With a rising population and the introduction of outsiders to Istanbul, the city’s social and economic life began to evolve. One of the state's new concerns was the social phenomenon of rapidly increasing prostitution. In reaction to this phenomenon, the state developed new methods of punishment for prostitutes in Istanbul, implemented fines for prostitution, but also attempted to construct a new set of moral-political values and to create a "pure" city within the frame of those new values. Tracing the evolving values around prostitution with a literary voice reveals the human side to this change. The shehrengiz of the poet Azizi provides a significant literary voice to contrast the values promoted by the state. Azizi's shehrengiz challenges his own time in two different ways: first, he writes about women, whereas most poems in this genre focused on the beauty of boys. Second, Azizi writes about prostitutes. He clearly challenges the state's attempt to set new moral-legal values by writing about the beauty of prostitutes. Thus, Azizi’s shehrengiz was a parody of not only the corpus of shehrengiz poetry, but also the emerging sets of moral values. Whether his subversions of the literary establishment were intended or not, he ended up challenging his peers. Details regarding Azizi's position in the social strata give possible motivations for these challenges. He was a warder at Yedikule dungeons, a job that likely allowed for interaction with prostitutes, but a job that did not put him in "high" intellectual circles. Thus, one could interpret two possible, paradoxical motives he had for writing his original piece. First, one might understand that Azizi sought fame and respect among his famous contemporaries, and wrote a sensational shehrengiz to get attention. While his peers' tezkire entries showed their reluctance to praise his poem, they also admitted to its popular appeal. The second interpretation is that his lack of immediate fame allowed him to be critical of the canonical conventions of writing shehrengiz. He had the freedom to write his shehrengiz without concern for the criticism of his intellectual circles or for losing his prestigious position, which it seems he never had.