This study examines the colossal amount of vulnerability around male sexuality in urban Zimbabwe and how such vulnerability shaped male sexuality and male perceptions to Sexual health. It is about how men in the urban arena handled the colonial shame of being, at best, second class citizens and, at worst, subjects and how in their attempts to deal with such shame, they appropriated different perceptions to their sexuality and manhood which had serious implications on how both the colonial and post-colonial governments dealt with Sexual health. It investigates the indignity on African male pride caused by living in a segregated and controlled urban environment and the impact it had on their sexuality especially when their beliefs in their maleness got blurred with the realities brought about by the colonial and post-colonial city. It asks poignant questions on how it felt to be a man in the city which carried a great deal of negative connotations and heavily impacted the way African men viewed, packaged and presented their manhood. It explores how the “tribal” African man had to rearrange his sexuality in order to conform to the demands of an urban environment that was socially engineered to control him and at the same time maintain the cultural and social values of the African rural society that raised him and instigated his manhood. It assesses the key areas of friction in the shaping of African masculinity occasioned by European colonial and later African governments’ attempts to control them. This control of urban Africans was initially driven by the imagined social chaos in the minds of Europeans prompted by the unwanted presence of “unsupervised” and “uncivilised “Africans in the colonial city. This study argues that in order to better understand and therefore better package health awareness messages and programmes for the urban areas in Zimbabwe, there is a need to understand how the mindset of African urban men have been shaped and impacted by the nature and character of colonial and post-colonial urban local governance and the broader nature and character of colonial policy especially towards Africans.