This study of young Black MSM (YBMSM) explored the correlates and outcomes of enhanced sexual pleasure from condom-protected sex. Six-hundred YBMSM were enrolled from an sexually transmitted infection clinic in the southern United States. Men completed a computer-assisted self-interview. A 3-item scale assessed perceptions related to condoms enhancing sexual pleasure. Nine of 14 correlates met the screening level of significance and were tested in a regression model. Three obtained multivariable significance: (1) Men discussing condom use with sex partners had greater odds (AOR = 1.67, 95 % CI 1.20-2.34) of experiencing enhanced pleasure; (2) Insertive-partners had lower odds (AOR = 0.63, 95 % CI 0.44-0.91) of experiencing enhanced pleasure; and (3) men scoring higher in internalized homophobia had lower odds (AOR = 0.66, 95 % CI 0.47-0.93) of experiencing enhanced pleasure. Also, men experiencing enhanced pleasure were less likely to report any condomless anal sex. The experience of enhanced sexual pleasure during condom-protected sex may be an important "target" of behavioral intervention efforts.