Using in-depth interviews and participant observations, I examine how two groups of heterosexual high school US football players alter differently the construction of heterosexuality and masculinity after joining collegiate cheerleading. First, I show that informants from both groups make masculinity accessible to gay men before next describing how they reconcile heterosexuality with limited forms of same-sex sex. Forty-percent of the heterosexual men I interview confirm engaging in same-sex sex, although they differently frame the requirements for it. I suggest these findings have various meaning for the relationship between sexuality and masculinity, as both groups somewhat strengthen and contest the borders of heterosexuality and masculinity. These findings beckon consideration as to how the relationship among sport, sexuality, and homophobia is changing.