Sissy boy experience is about not being a “real” boy or man and the social trouble that this causes. The scholarly work about sissy boys and their experience tends, on the whole, to consider the term to denote young people whose assigned sex at birth is male and who do not conform to the expected performance of gender that is understood to be properly masculine. This entry considers the way in which sissy boy experience has been considered in some literature and outlines a way in which the experience of naming boys as sissy might afford a disruptive resource for reworking systems of sex and gender.