The aim of this study was to determine the association between psychosocial determinants of unprotected receptive anal intercourse (URAI) and unprotected insertive anal intercourse (UIAI). Data from 417 HIV positive men who have sex with men (MSM) in the Multicenter AIDS Cohort Study from April 1999 to March 2012 were analyzed and adjusted odds were calculated. It was found that 66% (n = 277) and 72% (n = 299) reported any UIAI or URAI over follow-up, respectively. Cumulative cART-years (median = 5.30 years) was associated with 33 and 47% increases in UIAI and URAI, respectively. Not having reduced concern about HIV transmission (UIAI: OR 0.37, p-value = 0.0004; URAI: OR 0.57, p-value = 0.04), increased safe sex fatigue (UIAI: OR 2.32, 95% p-value = 0.0002; URAI: OR 1.94, p-value = 0.003), and sexual sensation seeking (UIAI: OR 1.76, p-value = 0.002; URAI: OR 1.56, p-value = 0.02) were associated with UIAI and URAI. Serosorting was associated with UIAI (OR 6.11, p-value < 0.0001) and URAI (OR 6.80, p-value < 0.0001). Findings suggest that negative attitudes about HIV transmission are sustained among older men who have sex with men.