OBJECTIVE The primary aim of this article was to examine event-level associations between alcohol use and sexual risk taking across first and repeat oral and vaginal sex encounters among at-risk college student drinkers. METHODS Participants (n = 221; 51.1% women) provided information on alcohol consumption, sexual activity, and event-level data on their most recent (repeat and first) experiences with oral and vaginal sex. RESULTS Of the total sample, 80.5% reported ever engaging in oral or vaginal sex. Alcohol use was more likely in new, compared with, repeat sexual partnerships. In addition, for recent vaginal sex experiences with a repeat partner, alcohol use was more likely among those who were less committed to the relationship. For new sexual partnerships, regardless of the type of sex experience, knowing the partner for less time was associated with an increased likelihood of drinking. Alcohol use was also associated with fewer discussions of topics pertinent to safe sexual practices. Finally, there was a tendency for drinking in conjunction with a new vaginal sex experience to be associated with a lower likelihood of contraceptive use. CONCLUSIONS These findings highlight the need for integrated interventions targeting alcohol use and risky sexual practices among high-risk college students, with a particular focus on alcohol use during new sexual partnerships and the often-overlooked connection between drinking and oral sex experiences.