Anejaculation is defined as the inability to ejaculate semen despite sexual stimulation by intercourse or masturbation. It may result from organic or psychological causes and can be classified as orgasmic, anorgasmic, and situational. Situational anejaculation may be present in intercourse type. This means existence of ejaculation by masturbation, but not during sexual intercourse. Performance anxiety, hostility toward the partner, dysfunctional psychosexual development, and unconscious desire to avoid pregnancy are the possible underlying conditions. We herein report situational anejaculation in 24-, 26-, 34-year-old males who presented with inability to ejaculate intra-vaginally since they got married. All of them were the sole males in their family, had a childhood in a conservative community, and had arranged marriages. Due to the negative aspects of psychosexual counselling in rural societies, it was not possible to continue the follow-up and treatment of patients. Despite this, the authors conclude that this clinical course of situational intercourse anejaculation suggests a psychological problem in these patients.