The issue of sexuality in Singapore is an ambivalent discourse that crosses the borders between prohibition and endorsement, official and unofficial and private and public. On one level, homosexuality is prohibited and consensual same-sex desires are punishable as criminal offences. On another level, transgenderism is endorsed by the discourses of biology and medicine, and sanctioned (albeit unofficially) through state support and policy. This ambiguity manifests itself in numerous aspects of Singapore’s cultural location within both Asia and the West, and is exemplified also in recent discourse about New Asia. This chapter will investigate the culture of such an ambiguity by examining the consumption practices of computer-mediated communication (CMC) technology by lesbian, gay, bisexual and transgender communities in Singapore cyberspace.