In the study of sexualities in Africa, slowly but steadily there is more space for research on non-normative desires and practices and especially of same-sex desires. Yet there are relatively few in-depth studies that research such experiences and practices as a subject in its own right, as opposed to as a component of sexual health and rights (cf. Tamale 2013). Consequently, knowledge, representation, and discourses about non-normative sexuality are either discussed in normative ways for their harmful effects, or same-sex desires are pioneered by activists of LGBTQI social movements and organisations and development agencies and LGBTQI activist scholars. The latter body of work takes the idea of non-normative desire more serious, and the notion of non-normative desire has become related to the notion of transgressive sexuality and of subjectivities that are suppressed by a hegemonic heterosexuality. However, Henrietta Moore warns us about the danger that theories of sexuality remain inadequate when analysing subjectivity primarily in terms of antagonism and/or subordination to normative structures (2007, see also Ortner 2005). Thinking in terms of suppression and empowerment may not capture the ambiguous, murky and powerful (Paglia 1991) realities of nonconforming desire. In this paper I would like to present three cases where people do not quite follow moral expectations, so as to delve deeper into understanding how and when the notion of transgressiveness -breaking a moral law or rule of behaviour- is productive but also when it is limiting. Some non-normative desire may be better understood in terms of manoeuvring personal desires and social expectations, that may or may not turn out to be agentic, empowering or productive. One case concerns the practice of infidelity, one of male virginity as an adult and one of same-sex intimacy.