Stories shape our social reality. This research explores new ways of storytelling around the topic of HIV and AIDS by using augmented reality (AR) and electronic literature to experiment with the meaning, structure, and form that a story can take. Employing a mixed methodological approach that combines Research through Design, Transmedia Storytelling and Critical Design methodologies, this thesis unpacks the potential of digital technologies in retelling and revisioning the story of HIV and AIDS as a way to give voice to stories that are often left unheard. AR Disclosures is an interactive documentary installation that tells stories about HIV in the form of augmented reality latrinalia. Once Upon A Virus is an interactive dystopian fantasy that subverts fairy-tale motifs in order to explore themes of inequality in relation to the AIDS epidemic. These two exploratory prototypes aim to propose new ways in which storytellers might leverage evolving new media technologies and experimental storytelling techniques to tell the story of HIV and AIDS to a new audience, while contributing to a developing definition of what the practice of storytelling is and looks like today.