This study sought to conduct an in depth analysis of women’s first sexual experiences looking for factors contributing to the experience and the emotional outcomes of first intercourse. Fourteen heterosexual, female, college students were interviewed about their first sexual experience and sexual background using a semi-structured interview format. The narratives derived from these interviews described definitions for first sexual experience, forms and effects of sexual education, reasons to engage in intercourse, influence and interactions with first sexual partner, shifts in sexual beliefs through development, meanings assigned to first intercourse, and regrets of first intercourse. Also included in the study is the advice the participants would give to other women prior to first intercourse to help women navigate the decision to engage in intercourse. The results of this study found an apparent lack of sexual education and inconsistent resources from which women gain knowledge regarding sexual experiences, and most interestingly two distinct belief shifts regarding intercourse, one prior to the experience and one resulting from the experience. The conclusions drawn from this research include a need for further research into the effect first sexual intercourse has on the emotional sexual development of women and a call for increased education to prevent damaging first experiences and promote sexual health in women.