This article considers the figure of the male virgin in Sherilee Gray’s Breaking Him, an erotic contemporary romance novel. In particular, this article considers the ways in which the novel works to maintain the hero’s masculinity, while also considering how the novel challenges masculinity. While the virgin hero may appear to challenge ideas of masculinity, particularly the sexualized hero, this article shows the ways in which the hero is constructed as masculine despite his virginal status. To these ends, I draw on recent scholarship in popular romance studies, porn studies, and critical studies of men and masculinities. Additionally, this article advances the idea of the “case study” as a model for the study of popular romance fiction. The “case study” as a model allows for a deep engagement with the text, while also looking outward to its possible value in the study of other cases.