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CONTEXT: Heterosexual anal sex is not uncommon in the United States, and it poses risk for STDs. However, who engages in it and why are not well understood, particularly among young adults. METHODS: In 2006-2008, data on sexual health-related topics were collected in surveys (483 respondents) and qualitative interviews (70 participants) with black and Puerto Rican 18-25-year-aids in Hartford and Philadelphia. Bivariate and multivariate analyses of survey data assessed predictors of anal sex with the most recent serious heterosexual partner. Interview transcripts were analyzed for anal sex experiences and reasons for and against engaging in this behavior. RESULTS: Some 34% of survey respondents had had anal sex; this behavior was more common with serious partners than with casual partners (22% vs. 8%). Black respondents were less likely than Puerto Ricans to report anal sex (odds ratio, 0.3); women were more likely to do so than were men (2.9). In the qualitative cohort, perceptions of anal sex as painful and unappealing were the predominant reasons for not having anal sex, whereas sexual pleasure and, in serious relationships, intimacy were the main reasons for engaging in it. Condom use during anal sex was rare and was motivated by STD or hygiene concerns. CONCLUSIONS: Heterosexual anal sex is not an infrequent behavior and should be considered in a broad sexual health context, not simply as an indicator of STD risk. Health providers should address it openly and, when appropriate, as a positive sexual and emotional experience. Perspectives on Sexual and Reproductive Health, 2010, 42(4):267-274, doi: 10.1363/4226710