To inform the development and assess potential use of rectal microbicide gels for HIV prevention among men who have sex with men (MSM), we examined the dynamics and contexts of commercial lubricant use during receptive anal intercourse (RAI) within this population. From 2007 to 2010, 168 HIV-negative MSM living in Los Angeles who practice RAI completed computer-assisted self-interviews, which collected information on their last sexual event with ≤3 recent partners, at baseline, three months, and one-year study visits. Logistic generalized linear mixed models were used to identify individual- and sexual event-level characteristics associated with commercial lubricant use during RAI at the last sexual event within 421 partnerships reported by participants over the course of follow-up. During RAI at their last sexual event, 57% of partnerships used a condom and 69% used commercial lubricant. Among partnerships that used commercial lubricant, 56% reported lubricant application by both members of the partnership, 66% first applied lubricant during sex, but before penetration, and 98% applied lubricant at multiple locations. The relationship between substance use and commercial lubricant use varied by condom use (interaction p-value = 0.01). Substance use was positively associated with commercial lubricant use within partnerships that did not use condoms during RAI at their last sexual event (AOR = 4.47, 95% [corrected] [CI]: 1.63-12.28), but no association was observed within partnerships that did use condoms (AOR = 0.66, 95% CI: 0.23-1.85). Commercial lubricant use during RAI was also positively associated with reporting more sexual partners (AOR = 1.18, 95% CI: 1.05-1.31), while older age (units = 5 years; AOR = 0.75, 95% CI: 0.61-0.94), homelessness (past year; AOR = 0.32, 95% CI: 0.13-0.76), and having sex with an older (>10 years) partner (AOR = 0.37, 95% CI: 0.14-0.95) were negatively associated with commercial lubricant use. These factors should be considered in the development of rectal microbicide gels to enhance their acceptability and use among MSM.