Praise poetry is an ambiguous genre in Kiswahili Literature. This is portrayed in its definition and manner in which it is used to create and maintain hegemonic masculinities. Although praise poetry is classified as a genre of Oral Literature, the language used captures the linguistic aspects that portray masculinity in various ways. The Isukha praise poetry that is chanted during the Shilembe ritual and the indigenous sport of Mayo is one of the ways in which masculinity is portrayed during bullfighting in this community. In this praise poetry, stylistic devices have been used to convey information using the semantic approach in context. This article highlights application of the masculinity theory and critical discourse analysis theory in the analysis of the stylistic devices used in praise poetry during the ritual of Shilembe and the indigenous sport of Mayo to portray masculinity. Though there are also other types of genre that portray masculinity in this community, but praise poetry is peculiar and distinct in this context, as it involves bullfighting.