Background: Condomless anal sex (CAS) accounts for most HIV infections among men who have sex with men (MSM). Knowledge of one’s HIV status through routine testing remains essential for reducing HIV transmission. We assessed the associations between demographic, behavioral, and prevention characteristics of MSM who engaged in CAS and HIV testing in the Dallas and Houston, Texas metropolitan statistical areas (MSA) in 2008 and 2014 and examined changes in CAS and HIV testing prevalence during this period. Methods: Data from the National HIV Behavioral Surveillance for 2008 and 2014 MSM cycles in Dallas and Houston were used for this analysis. We compared proportions of self-reported CAS and HIV testing and determined the adjusted prevalence ratios (aPR) using generalized estimating equations. Results: The overall adjusted prevalence of CAS among MSM in Dallas and Houston remained stable over time. MSM who had one sexual partner were 9 (aPR = 9.21, 95% confidence interval [CI] = 3.83–14.91, P < 0.0001) and 7 (aPR = 6.92, 95% CI = 2.29–20.92, P = 0.001) times more likely to engage in CAS in Dallas and Houston. CAS increased significantly by 36% (aPR = 1.36, 95% CI = 1.00–1.85, P = 0.052) among young MSM (18–29 years) in Houston. Overall, the prevalence of HIV testing in Dallas increased significantly by 63% from 2008 to 2014 (aPR = 1.63, 95% CI: 1.12–2.36, P = 0.010) and across the subgroups. In Houston, HIV testing was generally stable, overall and across most subgroups, except for race/ethnicity, education al status and number of sexual partners. Conclusion: The study highlights the need to tailor intervention efforts to each MSA unique circumstances and specific at-risk subpopulations as a mean to help reduce new HIV infection. In addition, the adoption of mutually-reinforcing HIV prevention interventions are recommended to overcome individual- and structural-level barriers to HIV testing especially in the MSM communities where testing are plateauing.