When I first started exploring my sexual life, there were times I would have jack off marathons. The marathons usually happened on a weekend, and I would have about 20 to 30 orgasms in those 2 days. I would jack off and have an orgasm. Instead of stopping, I would keep jacking off and have a 2nd orgasm. The best part was I would use the cum as lube to keep jacking off. I would keep going and get a 3rd orgasm. Sometimes I would keep going and get a 4th and 5th orgasm, but by that point, nothing was cumming out when I had the 4th and 5th orgasms. And the more orgasms I had, the longer it would take to get the next one. By the end of the weekend, I would have jacked off so much that my dick was sore. Two different times I rubbed the skin raw and would have a sore.
Those days are long over for me. Now I am lucky if I can jack off 3 times a day, most days I stop at 2.