This chapter sets the scene for the exploration of young people’s digital sexual cultures against the backdrop of global concerns about the failure of ‘Big Tech’ to protect minors from online sexual exploitation which has intensified public outcries about online safety and the need for protection. Moving beyond simplistic binaries of risk versus resource, this chapter argues that young people’s engagement with digital platforms can simultaneously foster sexual expressions of freedom and self-discovery while also reproducing constraints. With a focus on the project involving 420 young people aged 13 to 19 in South Africa, the chapter highlights the dual realities of risk and pleasure that characterise boys’ and girls’ interactions with digital technologies. The introduction also lays the groundwork for understanding the entanglement of gender, sexuality, and digital culture in the lives of young South Africans through new feminist materialism, arguing strongly for attention to both the human and more-than-human elements in their experiences. This book argues for a nuanced understanding that recognises young people’s sexual capacities in navigating digital environments whilst simultaneously addressing the materialisation of gendered inequalities that continue to harm women and girls.