A new reading of a rarely examined medieval Arabic text, Ibn Dāniyāl’s (d. 1310) shadow play titled “The Enchanted and the Enchanter (al-mutayyam wa-l-yutayyim),” suggests that the farcical comedy contains significant elements of the author’s own life story. On close examination, the cautionary tale, infamous for its outlandish depictions of a garden variety of “repulsive” sexual acts, manages, or pretends, to stay within the boundaries set forth by the premises of classical Islamic sex discourses. With an all-male cast, the beauty lauded, sexual fantasies projected, and desires produced illuminate a peculiar kind of aesthetics in erotica, created by, of, and for the segment of society that dominated sex discourses: free adult Muslim men. A sometime court jester and a popular entertainer, Ibn Dāniyāl’s hilarious yet sharp voice betrays an acute awareness of the constant shifts in attitudes and mores regarding male-male relationships at a pivotal time of the Mamluk Sultanate. Key words: Ibn Dāniyāl (d. 1310), Mamluk Sultanate (1250-1517), the Qalāwūnids, medieval Cairo, Arabic shadow theatre, homosocial entertainment, androgenous beauty