I lubed it up and gave it a try. No go. I got as much pleasure as if I were simply bringing my arm in and out of the cuff on a pulse measuring station at a drug store.
I am circumcised, and I normally masturbate by placing the heel of my palm in the area between my shaft and scrotum and humping. Things like pillows can work, too.
What the hell should I do short of seeing a doctor? I know my virginity isn't going anywhere soon, so I can afford to take my time on it.