Abstract This study examines Barbara Kimenye’s imagination of boyhood masculinities in the selected adventure stories from the Moses series. It is based on the understanding that gender is a social construct. The Research Report contributes to children’s literature and gender scholarships. In particular, through textual analysis of primary texts and gender related theoretical framework, I highlight various categories of masculine behaviour based on boy characters’ power, control and popularity at Mukibi Educational Institute – Kimenye’s fictitious boarding school in Moses series. I tease out complexities of both individuals’ and groups’ notions of manliness and how they manifest in various locales. I argue that there are many ways of being a boy. I also highlight how the author deploys satire to imagine a boarding school and how this space allows construction and performance of specific boyhood masculinities. In addition, I highlight Kimenye’s depiction of corporal punishment and family relatives and how these also allow for construction and performance of particular man-like behaviour by her boy characters. Kimenye’s imagination of girlhood masculinities is also explored by examining boy characters’ stereotypes on girls and how through Sekabanja – a girl character – the author manages to deconstruct this by portraying her [Sekabanja] as behaving as expected of a boy. In addition, I highlight Kimenye’s representation of enactment of gender inequalities in a mixed sex school. I also underline how illustrations also participate in the imagination of girlhood masculinities. I argue that by portraying a girl – Sekabanja – as behaving as expected of boys if not better, Kimenye is highlighting gender as a social construct and participating in deconstruction of stereotypes on girls and women through a literary technique.