In 2014 Canada’s prostitution laws underwent legal reform. The new legal regime criminalized, among other things, the purchase of a sexual service. Arguably, because their existence challenges the underlying rational of the Protection of Communities and Exploited Persons Act (that sex work is male violence against women), men sex workers and their clients have been excluded from the conversation. Moreover, there is a glaring gap in the literature in terms of men’s experiences hiring men sex workers. Drawing upon ten in-depth one-on-one interviews with men who self-identify as clients of men escorts, this thesis explores the commercial sexual exchange, risks and their management, stigma, and identity. The findings challenge the prevailing narrative of sex workers’ clients as either exploiters or pathetic losers, highlight the diversity of clients, nuance the range of experiences, and draw attention to the complexity of the relationships between clients and the escorts they hire.