In one of his aphoristic contemplations on photography, Walter Benjamin stated that, “The illiteracy of the future,’ someone has said, will be ignorance not of reading or writing, but of photography.” The images of female-to-male corssdressing in Qajar photography may be said to perfectly exemplify Benjamin’s dictum. Upon looking at these often mesmerizing photographs some important questions emerge: what is the logic operative behind these photographs? Why did the women in these photographs dress in men’s clothing? What were the commercial circulation of these photographs, if any? And for whose gaze were such photographs staged? And perhaps most importantly, what are the gender and sexual dynamics operative in these photographs? In this article, some tentative answers will be provided to these questions, with the overarching argument that these photographs largely represent the preference for male homoeroticism in the Qajar sexual imaginary, typified by such terms as amrad (young adolescent male), ghilman (youth) and wildan (boys). Though the images of women crossdressing as young boys or youth represent them as the object of desire for adult males (mukhannas), and stages the notions of beauty intimately linked to the culture of male homoeroticism prevalent in Qajar society, yet in some of the photographs it can also gesture towards female masculinity and lesbianism in which women crossdress in male attire, both to be desired by women and as desiring subjects. The photographic images that will be analyzed here are drawn from the rich digital archive collection at Harvard, “Women’s Worlds in Qajar Iran,” and still others from Persian textual sources. Many of the photographic images of female-to-male crossdressing fall within the sphere of male entertainment, such as prostitutes (rusbi) and musicians (motribs). There are photographs of women prostitutes corressdressing as boys/youth as well as musicians who are entertainers; they represent figures that entertain the male elite of Qajar society and the Qajar court. Among the anomalies and exceptions to this rule in the photographs is the figure of a young crossdressing female Babi warrior-commander in Qajar Iran, Zaynab, who did not crossdress in any of the above two senses, but rather as a figure who crossdressed as a man in order to fight the Qajar troops alongside her male co-religionists in Iran. Finally, what ties all the photographic images together is the marginalized status of these women in Qajar society.