The article explores pathways to male transactional sex, focusing on entering, soliciting practices, role of pimps, client characteristics, and negotiations. Little scientific literature exists regarding male transactional sex in India, who represent a high-risk group for HIV infection. Case studies with 10 men who engage in transactional sex were conducted, who were recruited using purposive snowball sampling and interviewed at a social service organization. Participants differed in their sexual identity, sex roles, soliciting practices, and clients. Most of them listed economic crisis as their reason for entering transactional sex. Strategies to find clients included self-solicitation and referrals, while pimps played a major role in solicitation, negotiations, and events of crisis. The relationship among men who engage in transactional sex, pimps, and clients involves points of negotiation, opportunities, and limitations. HIV prevention should focus on identifying and addressing the groups' unique needs and working with pimps on risk-reduction strategies and crisis interventions.