This book is an exploration of both mainstream and independent media. Grounded in qualitative methods, this book explores three trans masculine run YouTube channels alongside the streaming productions: The Chilling Adventures of Sabrina, Orange is the New Black, and Transparent. Analyzing and contrasting these narratives illuminates how even the most progressive of pop culture productions fail to present multi-dimensional transgender narratives, thereby intensifying stigma and shame for those outside of the binary (male or female, man or woman, gay or straight). In contrast, trans masculine produced YouTube vlogs, such as those discussed in this book, can help audience members unlearn the ways in which the continuum of sex, gender, and sexual orientation has been simplified and obscured through corporate media. These vlogs thus exemplify the various ways in which independent media acts as an educational tool toward greater awareness, and perhaps empathy, of/for the self and others in regards to sexual identity.