5-6 tops, probably when I was a teenager. My dick would be too sore to go more then that. Watched my last girlfriend go 9 times in a row once...hot
I have spent up to & over an hour sometimes doing kinky things anally on myself. I like trying to stretch it as far open as I can & keeping it open with objects that sometimes hurt for a start but then it eases off gradually.
I have done it 6 times in a day, but each was in a different location. Caravan, car, next to a river, shower, game viewing hide and just outside under the stars. I had been doing volunteer work at a game reserve and the work had been completed but I had two days there alone, sharing a caravan with a beautiful botany student. I was only 16 at the time while she was 24 and I didnt have the courage to think about flirting.
Was a girl I knew that was a few states away, we used to have phone sex so much it was incredible. I think we may of done it 10-12 times in a day, maybe give or take.. Daily these days I'm easily 5 times.
My record is 13 times in 24 hours. It was in years ago and a friend and I had a contest to see how many times in one day we could. We didnt do it together and he claimed he did 22 times. I do know after the third or fourth orgasm I was shooting blanks but it still felt great. We both agreed the next day we were pretty damn sore
I'm sure I've done high single-digits many times when I was younger, but probably never double-digits. These days, a good day is only 2, sadly. I did it a lot when I was younger, but if I knew what was going to happen when I got older, I definitely wouldn't have wasted any opportunities that I had.