The association between play and pleasure may seem natural, even intuitive. Although the hedonism associated with playful activities is generally evident in normally developing children, for children who have experienced early relational trauma (Bonneville-Baruchel, 2015), play can be related to displeasure, suffering and great psychological distress (Romano, 2010). Play, then, does not seem to obey the pleasure principle, nor for that matter the reality principle, in the same way that it is neither entirely in the realm of either reality or fantasy (Winnicott, 1975). This theoretical and clinical paper focuses on the evolution of the nature and role of pleasure in the psychotherapy of children who have experienced early relational trauma and who are able to experience pleasure. It attempts to demonstrate that for these children, pleasure is initially related to sensoriality, but that access to psychotherapy and pretend play allows a transition from a form of pleasure associated with the senses to one which is linked to meaning. The characteristics of play in traumatized children are outlined and clinical vignettes are presented to illustrate different manifestations of pleasure in children with early relational trauma.