I'm 28 years old and I've tried it hundreds of times over the course of my life, but have never been able to ejaculate due to not being able to get an erection and it being too painful to continue. I'll be masturbating for minutes on end and yet nothing happens, except pain. This is beyond frustrating beyond my sex drive is very high and I'm horny 24/7, but I can never masturbate or have sex. I'm seeing a doctor about this, however he is at a loss about what to do.