This chapter disentangles the web of terms that knots together the medical naming of transsexualism, the mediatized practices of trans sex, and what might today be recognized as the multiplicities of trans* sexualities. Carla A. Pfeffer has named trans sexualities ‘a lacuna’ in theorizations of sexuality and desire (2014: 598). For a growing number of (trans) scholars, trans sexualities, sex, and their mediatized representations are vital academic and political concerns. Trans sex and sexuality reveals the myriad ways in which gender and sexuality are interdependent and mutually constitutive, moving forward studies of gender and sexuality in practice, in policy, and even philosophically. Close analysis of erotic (self-) representations brings to light the possibility of experiencing both sexual fluidity and stability, resolving a long-standing impasse in feminist and queer approaches to sexuality (Steinbock 2011). In this chapter I will focus on two domains that provide insight into the cultural shifts around how trans sexualities are mediatized: transfeminine activism in queer pornography and, by way of conclusion, some notes on news coverage of how to talk about trans sex.