Modern Indian society has witnessed rapid sociocultural transformation where loosening of cultural values is observed at all levels. In the era of transition, traditional norms and values are changing where young male individuals are found to be associated with high-risk multi-partner sexual behavior. Findings are based on a nationally representative sample of 45,231 and 65,704 men aged 15-54 during the period 2005-2006 and 2015-2016, respectively. The burden of high-risk sexual behaviors among men aged 15-54years in India over the last decade remains disproportionately higher among younger, unmarried, and urban men, who are mainly from economically better-off households. Despite tremendous efforts of the government of India as well as various state governments in condom promotion as part of the HIV/AIDS prevention program, the improvements in condom use over the last decade are not impressive as it has not yet reached the desired threshold level. The disparities in high-risk sexual behavior among men aged 15-54years, coming from rich and poor households, have narrowed. The findings of the study also underline an apparent paradox in the relationship between knowledge of HIV/AIDS and indulgence in high-risk sexual behavior and adopting safe sexual practices. It is recommended that all the HIV prevention programs in India should promote the concept of men as the responsible sexual partner. This concept may be promoted among young and unmarried men by reinforcing the shift from violence to respect and projecting the condom as a sexual stimulus rather than a means of disease prevention.