The association of socialization patterns with unprotected anal intercourse (UAI) and HIV/STI prevalence remains underexplored in men who have sex with men (MSM) and transgender women (TW) in developing country settings. We evaluated the correlation of UAI, HIV, and syphilis with MSM/TW venue attendance and social network size among high-risk MSM and TW in Peru according to self-reported sexual identity. Frequency of venue attendance and MSM/TW social network size were lowest among heterosexual MSM and highest among TW respondents. Attendance (frequent or occasional) at MSM/TW venues was associated with increased odds of insertive UAI among heterosexual participants. Frequent venue attendance was associated with increased odds of receptive UAI among gay/homosexual, bisexual, and TW participants. Further investigation of the differing socialization patterns and associations with HIV/STI transmission within subgroups of Peruvian MSM and TW will enable more effective prevention interventions for these populations.