Technological advances like the Internet and Internet-enabled devices, such as smartphones, and the dating and hookup websites and apps available to the users of them, have transformed the nature, organization, and practice of sex work in fundamental ways. Some scholars have argued that these changes have contributed to a normalization of male exchange sex (i.e., providing sex in exchange for money, drugs, shelter, or goods), and in so doing, have diminished the stigma historically associated with it. However, little empirical research has focused on how male sex workers (MSWs), including those engaged in what might be called informal or incidental or casual sex work and primarily use dating/hookup websites and apps not designed for commercial to meet clients experience and manage stigma. To help fill this gap, we analyzed interview data from 180 MSWs who engaged in exchange sex and met their client on dating/hookup websites and apps. Most participants felt that sex work was still highly stigmatized in society at large, but many also felt it was generally accepted—if not completely normalized—within the gay community. Nevertheless, many struggled with the emotional impact of engaging in a stigmatized practice and most employed one or more of the following stigma management strategies: information management, distancing, discrediting the discreditors, asserting no other option existed, and challenging or reframing stereotypes and narratives. These findings indicate that MSWs, even those engaged in informal or incidental sex work, who meet clients on dating/hookup websites and apps are still strongly affected by sex work-related stigma and seek to manage it in various ways. Future research should investigate the sources of internalized stigma among this under-studied population of sex workers.