The increasing use of antiviral drugs, combined with an aging population, has resulted in a growing number of older adults living with HIV. Unfortunately, high-risk sexual behavior among older individuals with HIV has led to HIV retransmission. Our study aimed to analyze the sexual behavior of elderly men with HIV in Chongqing and evaluate the factors influencing high-risk sexual behavior using a logistic regression model. The study involved 774 participants with an average age of 62 years. Of the participants, 45.74% (N = 354) reported having sex in the past year, and 13.70% (N = 106) reported high-risk sexual behavior in the same period. Our study identified several factors associated with high-risk sexual behavior, such as low education level, commercial and temporary sexual partners, and lack of awareness and use of condoms. The results highlight the significant prevalence of high-risk sexual behavior among HIV-infected older men in Chongqing, and the potential risk of secondary transmission. Therefore, targeted interventions and education programs are needed, particularly for men over 50 years old, those with low education level, and those who engage in commercial or temporary sexual partnerships. Specifically, promoting condom use and increasing awareness of HIV/AIDS knowledge should be prioritized to decrease the prevalence of high-risk sexual behavior and prevent further transmission of the virus.