There has been a recent proliferation in the number of studies that are investigating the phenomenon that has been coined the victim–offender overlap. There has been noticeably less attention toward examining the sexual victimization and sex offending overlap. Acknowledging this gap in the literature, the present study provides an assessment of this overlap among a large sample of male prisoners with a focus on the cycle of violence hypothesis. Bivariate results reveal a considerable degree of overlap between sexual victimization and sex offending, and multivariate results estimated from a series of bivariate probit models simultaneously assessing both outcomes suggest that experiencing emotional abuse early on in the life-course is a robust risk factor for experiencing sexual victimization and demonstrating sex offending behavior. Furthermore, being physically neglected and witnessing family violence also emerged as significant risk factors for sexual victimization. Study limitations and policy implications are also discussed.