This paper examines a specific historical context of the virtual reality (VR), commonly associated with contemporary society, in order to consider its lineage. It sets up an argument that identifies archaeological examples, which worked with subjective perceptions of space, as predecessors to the digital technologies familiar in the 21 st century context. While the paper acknowledges the use of VR representation throughout history and around the world, the focus will be on key Roman villas, specifically on their frescos, and the importance of these immersion spaces in Roman society for reasons that approach both the social and introspective. As technology is not a term merely beholden to the digital, encompassing major revolutionary human advancements such as language or agriculture, the paper examines the historical technologies, i.e. the representational techniques, that produced virtual realities and immersive environments of the past. It uses the Ancient Roman context to illustrate the relationship between representation, subject(s), and society, which can be examined from a historical context and further applied to the contemporary.