Building upon our exploration of gender in Islamic history we dive into the topic of gender bending and how it can help us see gender as socially constructed, historically contingent, and contextual. We explore multiple figures through Islamic history from the ghulamiyya to the the bacha posh, from the khawal and the köçek to finally the mustarjil. Each of these figures troubles the imagined gender binary and instead presents us with an understanding of gender that is flexible and fluid. We also explore the possibility of transmen in Islamic history. The emerging image is that of an Islamic world which has much more nuanced understanding of gender than modern people give it credit for.