Based on the two clinical cases of a young adult and an adolescent in psychotherapy, this article reflects on the conscious and unconscious psychological aspects that are implicated in ‘first sexual experiences’. Regardless of the emotional circumstances that surround the actual experience and the way in which they take place, an aggressive, even violent fantasy is very frequently associated with the ‘first time’. This fantasy can complicate or hinder access to a shared sexuality with a partner. This article links such fantasies, on the one hand, to the Oedipal disappointment often experienced when a young person takes their initial step into genital sexuality, and, on the other, to the revival of an infantile sexuality endowed with a sense of separation. The exploration of the violent fantasies and death drive in therapy may facilitate the advent of a more consensual form of engagement with the other.