It is common knowledge that sex and pornography are among the major drivers of the Internet phenomenal success. The consumption of adult material is believed to have made a substantial contribute towards the establishment of e-commerce, and the development of novel communication technologies and interaction styles to increase the sense of physical presence of the partners. These include 360-degree visualisation techniques, desktop odorizers, sophisticated dildonics (electronic sex toys controlled by a computer) and teledildonics, or sex toys involving two partners over a network connection. Despite cybersex is such an important part of on-line behaviour and requires specialised interfaces, the HCI literature is mostly silent about this issue. On the contrary, the topic has witnessed some popularity within psychologists and clinicians since the late ‘90s. Mental health professionals initially labelled Internet sexuality as pathological. This perspective reflected a medical model with an emphasis on addiction, compulsivity and immorality. It posited that due to the interactive nature of the Internet, cybersex allowed a person to operationalize sexual fantasies that would otherwise have self-extinguished in the real world. Recently, a more open and positive view emerged. This adaptive perspective regards on-line sexuality as a new expression of sexual behaviour, emphasizing sexual exploration and relatedness. In this view, cybersex is regarded as an innovative form of sexual recreation ranging along a continuum from ‘normal’ to problematic’ expression. Most of the research on on-line sexual behaviour has addressed interpersonal relationships mediated by computers. Studies suggest that people who spend longer time on-line for sexual pursuit, tend to prefer chat rooms to pornographic web-site, as they are gratified by the social and interactive nature of these settings. This paper addresses a different type of interaction where the sexual partner is an artificial creature.