Cross-dressing complicates the gender and sexual ambiguities already underwrite the process of adolescent growth and development. The cross-dressed warrior girls in Young Adult fiction-in Tamora Pierce`s series, The Song of the Lioness and Terry Prachett`s novel Monstrous Regiment-offer an interesting literary study as their transgendering opens a space to critique the cultural divisions along the female/male as well as homo/hetero axis. Boyhood and girlhood emerge as socially and culturally encoded performances rather than rigid identity categories. Despite the heteronormative trajectory of growth, the crossdressed heroines disrupt the naturalization of the growth as heterosexual and gendered. Adolescence becomes a fantastic space and time where the established codes of gender and sexuality are defamiliarized and hybridized.