Online sexual engagement, exploration and even criminal offences among youth is a common practice, and there can be blurred borders between pubescent explorative engagements and illegal activities such as digital rape. At the same time, digital rape is a serious sexual, often violent crime, which can have devastating and long-lasting consequences for its victims. The focus of this chapter is to advance the perpetrator’s perspective through a case study. The methodological approach is qualitative and consists of interviews with a young boy, Alex, his diary and his Court judgements. The material tells about Alex’s logic related to online sexual activity, analyzed in light of theory of computer-mediated communication. A central focus is how this type of communication differs from face-to-face meetings, and how such meetings exceed the local and temporal by what we usually think of as rape. The chapter highlights some of the core challenges met when digital, often generation-specific transgressive practices cross boundaries, become illegal and meet courtrooms and legal provisions. The article points to the challenges of providing a research-based approach to policy interventions, legal initiatives and the need to accept the complex nature of computer-mediated communication. Further, it points to the need to develop a legal vocabulary that can be understood and find its legitimacy – in the Internet generation and beyond.