Recent studies have documented changes in the prevalence and timing of first sexual experiences by gender and sexual identity; yet much of this research has failed to consider how these identities intersect with generational differences to influence young people’s sexual experiences. Moreover, extant work in this area has largely focused on sexual behaviors that are concordant with societal expectations based on sexual identity. Using data from the 2011–2017 National Survey of Family Growth, we examine how gender, sexual identity, and generation intersect to shape engagement in and the timing of first same-gender sexual experiences and first vaginal intercourse. Multivariable results show that, in general, engagement in same-gender sexual behaviors has increased across generations, while engagement in vaginal intercourse has decreased. Shifts in the timing of first same-gender sexual experience were found to be contingent on generation for bisexual women and gay men, whereas shifts in the timing of first vaginal intercourse were contingent on generation for straight women and men. Insights from this study underscore the importance of considering how multiple aspects of personal identity and the broader social context in which young people are raised, intersect to influence various sexual experiences.