There is no doubt that our major cities are marketed as cosmopolitan metropolises, each branding itself with the unique and defining characteristics it offers dwellers in terms of liveability. Although the objective is to compete globally through differentiation, these contemporary cities share a commonality of being diverse: they are inhabited by multiple identities of difference. Managing “difference” presents built environment professionals with an array of cultural and subcultural identities that are not always obvious in the urban landscape. Planners, in particular, are challenged with managing conflicts that may arise when these identities are in close proximity to each other. This thesis focuses on one subculture identity—men who sell sex (MWSS). In Sydney, New South Wales (NSW), where the sex industry is decriminalised, private sex work and MWSS are considered identities of difference with high conflict rates. Through policy reviews, spatial mapping, and in-depth interviews with key stakeholders, this research explores both the permissibility of the land use termed “home occupation (sex services) (HOSS)” and the understanding of MWSS in metropolitan Sydney. Analysis of planning controls reveals that local governance does not often permit the HOSS and fails to recognise the diversity of operations and premises associated with sex work. The spatial mapping describes that there are MWSS in metropolitan Sydney regardless of current land-use policies. The stakeholder interviews expose the sensitivities around sex work even when decriminalised. This study challenges the ambiguity of planning policy relating to private sex work in Sydney, where councils often fail to acknowledge the HOSS as a separate land use. Findings reveal that sex work is a diverse occupation in Sydney. They dispel the stereotype that sex work is a disruptive activity in urban life and distinguish that private sex work is a legitimate activity, separate to large commercial sex-industry venues, and operating like any other home-based occupation. Policy needs to reflect this in order to provide sex workers with the same civic rights as other urban dwellers. Overall, the study conveys that private sex work and MWSS are an identity of difference which can exist cohesively in metropolitan Sydney.