Throughout history, sexuality has been one of the most censored topics in literature. When literary works travel across linguistic, cultural and geographical borders, sexual descriptions are often subject to an additional process of filtering to the rest of the texts. This filtering is the product of interacting with the status of literary censorship in the dynamic target context at a given historical moment. Using selected Japanese translations of the erotic Chinese classic Jin Ping Mei as a case study, this chapter investigates the rewriting of sexuality in literary translation. Recognising that translation is first and foremost a target culture phenomenon, the chapter aims to investigate how the social construction of sexuality evolved in the Japanese context, and how this evolution interacted with literary translation. In the process, it will reveal how factors such as the agency of censors, readers, translators and literary genres and modalities affected individual translation products. Based on extensive contextual analysis, the chapter argues that when it comes to erotic translations in which fidelity cannot be observed from the linguistic or textual level, there is perhaps a gained opportunity for translation studies to move its attention to contextual fidelity.