The timing of first sexual intercourse is often defined in terms of chronological age, with particular focus on "early" first sex. Arguments can be made for a more nuanced concept of readiness and appropriateness of timing of first intercourse. Using data from the third National Survey of Sexual Attitudes and Lifestyles (Natsal-3), conducted in 2010-2012, this study examined whether a context-based measure of first intercourse-termed sexual competence-was associated with subsequent sexual health in a population-based sample of 17-to 24-year-olds residing in Britain (n = 2,784). Participants were classified as "sexually competent" at first intercourse if they reported the following four criteria: contraceptive protection, autonomy of decision (not due to external influences), that both partners were "equally willing," and that it happened at the "right time." A lack of sexual competence at first intercourse was independently associated with testing positive for human papillomavirus (HPV) at interview; low sexual function in the past year; and among women only, reported sexually transmitted infection (STI) diagnosis ever; unplanned pregnancy in the past year; and having ever experienced nonvolitional sex. These findings provide empirical support for defining the nature of first intercourse with reference to contextual aspects of the experience, as opposed to a sole focus on chronological age at occurrence.