This Article explores masculinity in rural areas, and it addresses bullying and harassment of gay, bisexual, transgender, and otherwise gender non-conforming boys and men. While all men are under constant pressure to perform masculinity correctly and act like a "real" man, rural boys and men experience unique forms and degrees of gender policing and victimization. The confluence of geographic, social, religious, and economic characteristics common in many rural areas results in few available options for exhibiting acceptable masculinity; even benign and seemingly gender neutral traits quickly become proxies for effeminacy. Moreover, the cultural salience of rurality in the construction of all masculinities helps explain why certain men everywhere are targets for ridicule and abuse. The law must protect these boys and men from discrimination, and this Article suggests that a broader interpretation of the Title VII and Title IX "sex stereotyping" doctrine, conscientious of the social context in which discrimination occurs, is one necessary and achievable route.