Male and female students manifest different behaviors in condomless sex. This cross-sectional, exploratory, correlational study examined the differences in risk factors for condomless sex between male and female high school students, using secondary data from 4,968 sexually active males and females participating in the 2011 National Youth Risk Behavior Survey. Results in descriptive statistics and multivariate binary logistic regressions revealed that condomless sex was reported as 39.70% in general. A greater proportion of females engaged in condomless sex (23.26%) than did males (16.44%). Physical abuse by sex partners was a common reason for failure to use condoms regardless of gender. Lower condom use was found in (1) those experiencing forced sex by a partner in males, (2) female smokers, and (3) female with multiple sex partners. Thus, sexual health education should address the different risk factors and consider gender characteristics to reduce condomless sex.