This chapter shows how a fluid view of gender identity, irrespective of the reality of the gender of the pair, facilitates the emergence of the paternal as well as the maternal function in this therapeutic dyad. For the boy the desire to return to the maternal shelter very often brings his sexuality into play. Desire is frequently considered to be the province of Lacanian theorists. The chapter also shows how art facilitates in states which are otherwise inexpressible. When experience is unbearable the artwork, as an embodiment of the transference, may act as a container, mediating between artist/client and spectator/therapist. It shows that analysis in one session per week becomes viable when pictures play a central role and embody the transference. The chapter argues that the reality of the gender of the therapist-client pair is a significant factor. It focuses on particular transference–counter-transference issues encountered by the female therapist working with the male client.