Abstract: This investigation into the online male sex trade in Melbourne explores the Internet's rise in popularity as a marketplace for male sex workers (MSWs). It examines the ways in which clients and workers engage with the Internet, as well as the effect(s) of this new domain upon workers and their professional encounters. The study finds that engaging in sex work is a common experience for young, attractive gay men, with many opting to offer their services (illegally) online in favour of more traditional sites (e.g. street, brothel/agency and print) due to a number of perceived advantages - such as anonymity, convenience and greater economic rewards. In turn, clients of MSWs also prefer to use the Internet for reasons pertaining to privacy and convenience. The marketing strategies employed by MSWs widely exploit stereotypes associated with (gay) masculinity in a market where visual representations of sexuality are of paramount importance. The study examines workers‟ perceptions of success. Many associate long-term success in the industry with an ability to self-monitor, allowing for the maintenance of a wealthy client base. Finally, the study investigates the key legislative and social issues that may complicate the working and personal lives of Internet-based male sex workers (IMSWs).