For youth who challenge the culturally fixed gender dichotomy through nonconventional gender expression, societal reaction can be harsh. Uncovering these youth voices as they pioneer new gender frontiers through pathways of language and social dialogue provides the focus for this manuscript. Drawing from discursive, narrative practices, we sat in on a transgender youth conversation group and positioned ourselves as outsider witnesses. The manuscript presents the tellings of the youth and our retellings, as reflective listeners, of their narratives of identity and social relevance. This research offers readers the opportunity to step into the lives of gender-nonconforming youth who are at a very different place in understanding gender identity than most professionals working with youth populations.