In the 1990s, a fascinating genre emerged: the virginity loss confessional genre, in which autobiographical stories of virginity loss are collected and curated. This article draws on the work of Michel Foucault and Kenneth Plummer to explicate the historical and theoretical bases behind this contemporary confessional storytelling practice, outlining the genre’s historical and therapeutic purposes. It also considers the significance of virginity loss and the relevance of these stories in the 21st century. It illustrates how and why virginity loss stories have been told in the past, and the reasons why publicly telling these stories has become a common practice in recent decades.