This qualitative study explores how perceptions of masculinity, sexual intimate relationships and sex-for-pay (SFP) shape the experiences of men who pay women for sex (MPWS). Semi-structured interviews were conducted with 16 Israeli MPWS. Participants were recruited through an STD community clinic, an anonymous online survey, ads posted in online forums for MPWS, and an organization for the abolition of prostitution. The findings offer a complex understanding of the experiences of MPWS, based on the intersections between their views of sexuality within long-term intimate relationships, and their perceptions of the acceptability of SFP within dominant discourses of masculinity. The findings comprise four experiential patterns of the multi-layered practice of paying for sex: Agonizing, Ambivalent, Intermittent and Simultaneous.