First sexual intercourse is considered to be a major life transition, but it is not always a pleasurable experience, especially for females. The major purposes of this research were to examine gender differences in emotional reactions (pleasure, anxiety, and guilt) to first intercourse and to test possible explanations for these gender differences. Based on data collected from 1,659 college students who had had sexual intercourse, we found that men reported experiencing more pleasure and anxiety than did women, whereas men reported experiencing less guilt than did women. Men's greater subjective pleasure in response to first intercourse was explained, in part, by their greater likelihood of having an orgasm. Similar gender differences in emotional reactions were found regardless of the stage and length of the relationship in which first intercourse occurred; both genders reported more pleasure, more anxiety, and less guilt when sex occurred in a close relationship than in a casual one. However, continuing involvement in the relationship was associated with a pleasurable reaction for women. Other ways in which gender was related to the first intercourse experience are also presented.