In a sample of men who have sex with men (N = 404), 55 (14%) experienced anodyspareunia, frequent and severe pain during receptive anal sex. Most men with anodyspareunia described their pain as life-long, experienced psychological distress as a result, and avoided anal sex for periods of time. Men with anodyspareunia reported that psychological factors were the primary contributing cause of their pain. The findings contradict the myth that pain is a necessary consequence of receptive anal sex and show that anodyspareunia is similar to dyspareunia in women in terms of prevalence, mental health consequences, and contributing factors. Clinical criteria were developed to assist clinicians in diagnosing anodyspareunia.