The United States continues to be affected by the HIV/AIDS epidemic, and now public health is faced with new challenges in mitigating the spread of the disease. African-Americans are disproportionately affected by HIV and a further understanding about the factors that influence high risk sexual behaviors needs to be continuously examined. The aim of this study was to understand and compare the the perception of HIV risk and factors associated with risk perception in high risk adult and adolescent groups. After multivariate analysis, having multiple partners was the only predictor of an increased risk perception among adults. Among adolescents, no significant relationship was found between HIV risk indicators and having an increased HIV risk perception. Both adults and adolescents appeared to underestimate their HIV risk based on their reported risk sexual behaviors. More work is necessary to help adolescents accurately assess their risk of infection.