This thesis captures the experiences and perspectives of a new generation of parents who identify and raise a child as transgender. Drawing on in-depth interview data with 56 parents, who speak to 43 cases of significant childhood gender variance, I explore several dimensions of the trans-parenting phenomenon that illuminate new cultural reckonings with gender, sexuality, the body, the binary, and identity. First, I examine the wealth of interactions and observations parents have with and of their children, through which parents ultimately come to understand their children as transgender. These stories highlight the child-directed, child-centered dynamics of childhood socialization in a new context---gendered childrearing and (trans)gender identity development---dynamics that are the vehicle of trans-affirmative parenting. Next, I turn to parents' and professionals' distinctions between, and sometimes re-interpretations of, "trans" and "gay" understandings of non-normative expression. I then explore parents' newfound reckonings with non-binary identities and expressions, both practically and conceptually. Lastly, I consider parents' privacy negotiations on behalf of their children, along with their biomedical accounts for their children's transgender embodiment, and the cisgender body logics that undergird both. Taken together, the analyses across these different domains of parents' experiences expose the cultural work that is giving (trans)gendered subjectivities increasing viability and intelligibility at particularly early points it the life course. The research also shows the prevailing constraints that a binary order imposes on more gender-variant and non-binary subjectivities and embodiments, especially for children assigned male and trans-feminine possibilities, as well as the raced and classed inflections of this parenting model.