Childhood is a contradictory construct that contains narratives that tend to romanticise children as well as ‘darker’ notions that speak to their transgression and deviancy. In contemporary times, notions of childhood as an age of innocence have connected with increases in the regulation of intimate life, including its expression online, to dominate social and political discourse. However, there is another more confronting narrative of childhood that accepts that children may often have a level of maturity to make their own decisions, understand matters pertaining to their sexuality and question authority. While such narratives are often said to steal childhood and lead to deviancy and illicit behaviour, this chapter suggests that such outcomes lead us to question assumptions about what is ‘good’ and ‘bad’ in this context. In the result, acknowledging children’s right to transgress can disrupt the very definition of what is deviant or illicit.