Fan fiction may be a relatively new form of transformative storytelling, but it is one that has polarised views from critics, scholars, and the general public. As a practice concerned with the amateur writing produced by fans derived from existing media, it has earned both critical condemnation as an unauthorised, illegal, and ‘transgressive’ practice, as well as the fascination of scholars concerned with participatory culture and media fans’ reinterpretation of existing material. This thesis explores the ternary relationship between creators, content, and community in relation to the retelling of stories (how individuals, communities, and online subcultures appropriate, adapt, and transform stories to new purpose). It does so by first examining myth, folklore, and fairy tales in a sociohistorical and sociocultural context and establishing the fundamental characteristics of transformative storytelling, then applying this analysis to fan fiction, both as a cultural practice and regarding its critical and legal reception. To explore the transformative roots of storytelling in a contemporary setting, it examines the intertextual relationship between professionally published and fan published works: the Harry Potter series (1997 – 2007) by J. K. Rowling, Carry On (2015) by Rainbow Rowell, and rebel rebel (2018) by BasicBathsheba. In doing so, it considers queerness in contemporary literature and the inherent queerness of producing/consuming queer ‘slash’ fan fiction, participatory culture, the legalities of transformative works, and how transformative texts trouble the assumed dichotomy between professionally published and fan published fiction. It argues that if new forms of transformative texts, such as fan fiction, are deemed ‘transgressive’ then this legacy of transgression is a long one, and that transformative texts hold cultural value not despite their transgressive nature, but because of it.