My 52 year old b/f has not been able to ejaculate recently. He tells me it's his problem, not mine... I still feel inadequate though. I know he masturbates frequently and I know he has a woman he has phone sex with. Could his problem be too much masturbation or perhaps he's trying to keep two women satisfied? Could he have prostrate problems? He does get hard but doesn't always stay hard. He does ejaculate but only 1 out of 3 times.