Objectives: In the context of women's vulnerability to sexual violence, HIV infection and unintended pregnancy in South Africa, this paper explores the ways in which teenage mothers who are in school reflect on their experiences of pregnancy and motherhood. We attempt to understand how teenage mothers reflect on their experiences within the cultural and institutionalised discourses in which they are embedded, and how their reflections lead to critical assessment and questioning of the dominant discourses of femininity that compromise women's sexual health. Methods: This paper draws on findings from a study with a selected group of teenage mothers in a Durban school. Main data collection strategies comprised individual and group interviews. Participants' reflections on their experiences of teenage motherhood are discussed in relation to three themes: "regret and pride", "contesting female victimhood" and "lessons learned". Results: Many teenage mothers indicate that being pregnant and having a child while still at school provides an impetus to take control of their lives. The data suggest that study participants use their reflections to construct a version of femininity that enables them to express themselves in ways that demonstrate greater agency. Conclusion: The greater agency expressed by teenage mothers has implications for their future sexual health and prevention of subsequent unintended pregnancies. In particular, it opens up possibilities for engaging them as peers in health education focusing on prevention of unintended pregnancy, by drawing on useful insights from lessons learned.