While a number of studies have explored the correlates of casual sexual behavior, few have examined how malleable psychosocial characteristics such as sexual satisfaction and reasons to have sex interact with each other in predicting risky sexual behavior. The present study examined the interaction of gender, sexual satisfaction, and reasons for having sex as predictors of propensity to engage in casual sexual behavior (sexual permissiveness) in a sample of 269 women and 86 men [mean age (M) = 22.05years, standard deviation (SD) = 3.02]. Among men who reported having sex relatively frequently for non-sexual, goal-oriented reasons, higher levels of sexual satisfaction were associated with lower levels of sexual permissiveness, while for men who reported having sex relatively less frequently for goal-oriented reasons, sexual satisfaction was unrelated to sexual permissiveness. Among women, sexual satisfaction was associated with lower sexual permissiveness only for those who reported having sex relatively infrequently for goal-oriented reasons. For women who reported frequently having sex for physical pleasure, higher levels of sexual satisfaction were associated with lower sexual permissiveness. Satisfaction was associated with lower sexual permissiveness for men independently from their physical motives to have sex. There was no relationship between having sex for insecurity reasons and propensity for casual sex. These findings are explored in the context of the protective factors of sexual satisfaction and the role of gender in moderating these relationships.