This thesis provides an overview of the first empirical study of ‘incidental sex work’, a form of casual, occasional, unplanned commercial sex arranged on digital media platforms. Rather than advertising, the (50) young sexual minority men I interviewed agreed to sell sex after being propositioned by (125) older men on social networking sites and smartphone apps. Alongside qualitative interviews including photo-elicitation procedures, a survey of 1,473 Grindr users aged 18 to 28, from major cities across England and Wales, found that at least 14.6% had been paid for sex (8.2% incidentally). Interview participants had diverse experiences of acceptance and discrimination in their coming out narratives, sexual experiences, and social networks. Incidental sex work encounters involved a range of behaviours, including ‘vanilla’ and ‘kinky’ sex acts, forms of emotional labour, and webcamming. In most cases, participants framed their paid sexual experiences as comparable to unpaid sexual experiences. Economic motivations included low or insecure incomes, student debts, and the ability to consume (both ‘essential’ and ‘consumer’) goods and services, while sexual motivations included ‘boredom’, ‘desire’, ‘experimentation’, ‘opportunity’, and ‘thrill’. Almost all of the participants distanced themselves from conventional labels such as ‘escort’, ‘rent boy’ or ‘sex worker’, suggesting that their behaviours were not ‘regular’ or ‘professional’ enough to count, alongside a desire to avoid association with stigmatising stereotypes of sex work as criminal, immoral, and pathological. Most incorrectly believed that their behaviours were illegal, but also argued that state interventions would be ‘pointless’, ‘harmful’, or ‘impossible’. Highlighting historical and contemporary associations between sexual minorities (principally men who have sex with men and women who sell sex), this thesis draws on postmodern theories of class, gender, and sexuality to suggest that the boundaries between casual and commercial sex have become blurred by changing social attitudes and the proliferation of internet technologies, complicating the ubiquity of discourses of despair, sexual identity politics, and regulatory policy approaches