By the early eighteenth century Edo (present-day Tokyo) was one of the largest cities in the world. Sex and erotic allure could be found in many guises in this commercialized urban setting, both in the city’s streets and in print. This chapter sets out to argue that sex assumed a multiplicity of meanings in this context that ranged from pleasure and procreation to potential pathology. To this purpose, it begins by tracing various discourses surrounding the three phenomena that have arguably received the most sustained attention in research to date, namely the sex trade, male same-sex desire, and the erotically explicit materials known as ‘spring pictures’ (Japanese shunga 春画/ shunpon 春本). The final sections aim to move beyond the standard narrative of the Edo period’s flourishing erotic culture by focusing on the female reproductive body, as well as medical and health discourses, thus aspiring to unsettle the paradigmatic character of this (male) pleasure-centred mode of sex and repudiate the monolithic view of early modern Japanese sexuality as unregulated.