In this article, we explore how ten men who took part in naked photoshoots for charitable purposes make sense of their embodiment as men. Through semi-structured interviews, we look at how participation in such a novel experience of nudity with other men underpins transformations of masculine conventions as well as some of the tensions present in these men’s accounts of the events. We highlight three significant discourses that exemplify these patterns: Nudity as Enabler of Intimacy; Surveillance and Insecurities; Producing the Natural Body. Our findings showcase the important ways that men can and do engage critically with masculinity while at the same time exploring some of the ambivalent ways that these challenges can manifest.