This chapter presents a discussion of sadomasochism (S/M). Drawing on secondary data from academic studies and published accounts by practitioners of sadomasochism, the authors present S/M as a disorganizing set of practices revealing the socially grounded nature of self, being, the body, desire and pleasure. They argue that this genre of sexual behavior can be understood as allowing those who indulge to express forbidden and dangerous desires, to respond to the compulsive return of the abject. It is the disorganizing and organizing character of S/M which is the authors' central concern in this chapter. In addition to an extended consideration of the various facets of the limit experience that is S/M, they discuss what it might teach us in terms of the modern organization, given the dialectical character of power relations in the S/M encounter. The authors also consider trust in this regard, suggesting that S/M both depends on and creates deep intimacies which stand in complete contrast to the shallow, truncated and instrumental bonds typical of the organization. Finally, they consider the challenge that S/M poses to the mind/body dualism, and thus, when extended, to the boundaries of organizations themselves. The authors begin, however, with an analysis of the ways in which this kind of sex reconfigures notions of pleasure.