“Cruising Baghdad” examines masculinity and sexuality in interwar Iraq through forms of homosocial and homoerotic notions of friendship and relationships. Moving from the homosocial to the explicitly homoerotic, this paper engages with both sanctioned and normative friendships and relationships as well as more illicit, nonnormative, and unsanctioned practices and desires. It turns to literature as an important repository of critical and alternative voices as well as alternative visions of sexuality, masculinity, state, and society. More specifically, it examines and discusses these questions through the fictional and autobiographical writings of Iraqi communist, teacher, and prose writer Dhu al-Nun Ayyub. Ayyub was born in Mosul and graduated from the Higher Teachers Training College in Baghdad, which had been established in 1923 and which where to educate many prominent Iraqi intellectuals. He died in 1988 in Vienna. Ayyub is considered to be one of the pioneers of Iraqi fiction and is recognized for the satirical and often sociopolitical flavor of his works, but the literary quality if his works is often described as less mature and less developed than the works of the 1950s generation. The homosocial, homoerotic, and sexual themes in Ayyub’s writings have received little attention. Only one critical work in Arabic exists on Ayyub’s eight volume confessional autobiography. This paper focuses primarily on the short stories published in the collection Sadiqi (My Friend, 1938) and argues that the sexualized description and celebration of the male body in Ayyub’s short stories represent instances of homosocial and homosexual desire. Ayyub’s short stories also highlight the ways in which the disciplinary and militarist discourses of the state in interwar Iraq were challenged from a number of different positions and by a number of different actors. In other words, this paper suggests, without reducing sexual desire to resistance, that Ayyub’s short stories raise important questions about how Iraqi men responded to, complicated, and subverted the nationalist and militaristic body image propagated by the state as well as normative sexuality. Finally, this paper hopes to open up a window onto our understanding of masculinity, male culture and friendship as well as relation(ships) in an almost exclusively homosoical public sphere in which friendship, leisure, and social relations were gendered and constructed along same-sex lines. In tandem, “Cruising Baghdad” attempts to visualize the relationship between, friendship, sexuality, space, and leisure in the modern city of Baghdad.