Our study aimed to understand the relationship between the status of high-risk sexual behaviors of male ≥50 years old (elderly men) and their family support in a rural county-level city in Chengdu. Multi-stage sampling was used to select rural elderly men from six towns to conduct an interview questionnaire survey. Ordinal logistic regression was used to analyze the relationship between high-risk sexual behavior and family factors. A total of 790 samples were included, and the prevalence of high-risk sexual behavior was 16.2%. Two-hundred thirty-nine men (30.3%) had three close family members. More than half of the men (n = 397) had never been provided financial support by family members (50.3%). More than half of men (n = 406) never communicate deeply with family members (51.4%). Logistic analysis reported that 50−59 years old (odds ratio [OR] = 1.928, 95% confidence interval [CI] = [1.070, 3.477]), unmarried, divorced/widowed, married and separated (OR = 8.232, 95% CI = [2.640, 25.673]; OR = 3.589, 95% CI = [1.713, 7.520]; OR = 3.003, 95% CI = [1.238, 7.280]) elderly men were more likely to be involved in commercial sex. Meanwhile, either never or often family financial support (OR = 0.435, 95% CI = [0.228, 0.830]; OR = 0.288, 95% CI = [0.095, 0.876]) helped elderly men to avoid commercial sex. This study predicts family factors may be affected by loneliness, life satisfaction, disposable economic condition, family responsibilities as the middle path, thus affect high-risk sexual behaviors in elderly men.