This paper interrogates the contradictions in the presentation of masculine identities in African literature and Kenyan literature in particular. This is done through a critical reading of Marjorie Oludhe’s Coming to birth. In the main, the paper examines the construction of masculinity in the society with a focus on gender roles, stereotypes, behaviour and general presentation of masculine qualities. In order to do this, the paper analyses how the rural and urban setups as presented in Coming to birth influence and alter the construction, maintaining and portrayal of masculinity as explored in the representative text. This approach allows for the interrogation of masculine behaviours and men’s struggle to perform masculine qualities and expectations fitting their identity. It is worth noting that the portrayal of male characters’ qualities in Coming to birth is marked by a level of frustration, anxiety, unfulfillment and hopelessness in the quest by men to show their masculine nature albeit elusive.