Sex markets, like many service industries, have been transformed by the digital revolution. I used digital multimethods, grounded in an ethnographic approach to examine the technological changes that have fundamentally changed the organisation of sex markets. Specifically, the research analyses digitally mediated sexual services from the perspectives of customers and workers and how their experiences inter-relate with the legal and regulatory structures. The findings suggest technological changes have created more fluidity between roles specially amongst men in the study, than has been recognised before. I suggest the legal framework legitimises digital sex work as entrepreneurial, while condemning public forms of sex work, yet all sex workers continue to navigate stigma associated with commercial sex. I conclude that the legal structures create uncertainty for sex workers and customers, and ultimately sex workers look to the platforms for safety rather than the police. This work is important as it revealed digital sex work could be better understood as a form of digital labour in the ‘gig economy’ showing the gender blindness of much of the mainstream literature on digital labour.