We describe the work of two groups of middle school youth as they authored stories set in their community, based on superhero and absurdist storytelling genres. Their storytelling was part of a weekly ELA project that took place from February through May 2017 in a public middle school in a neighborhood where economic inequality defines many facets of everyday life. Drawing on audio and video recordings from ten weekly storytelling events, field notes, interviews, and close readings of youth narratives, we describe how youth created and initiated proleptic bids and, thereby, opened proleptic gaps for improvising on and producing new material with the potential to rescript the meanings of childhood and equity in their communities. We argue that these bids and gaps made space for youth to not only critique but also move beyond dominant readings of their neighborhood, and we suggest that such openings are therefore necessary for transformative literacy pedagogy and practice. We further argue that proleptic pedagogy, in the form of joint storytelling, affords a compelling and sustainable space for youth to experience joy, friendship, and artist-authoring identities, all of which have been systematically eroded by federal, state, and district policies oriented to testing and closed meanings.