I was a huge wimp when it came to pain, still am, but there are two things that stick out in my mind. When I was very young, I'd try and push everything inside or back and then keep it there with really tight undies. By the time I hit puberty, it was all too big to stay inside, so I would push it all back between my legs before I went to bed and hope that it would be gone when I woke up. I had my first orgasm this way actually; that was VERY strange.

One time at about age 13 or 14 I was doing this to get off, and I pulled it back when it was hard. SNAP! I broke the suspensory ligaments, and it hasn't worked right since. My eyes watered and I was afraid to touch it for a week, but I got over it.

I was afraid to do anything more until about a year ago.