I did this with a fuck buddy I had about 20 years ago. He lived in Milwaukee, and I went up to spend a weekend with him. We went out one night and had a few drinks. When we got back to his place, we had sucked each other when we got into bed, I put a new cockring on and fucked him. I was spooning him when I shot my load. We just stayed in that position and fell asleep. I woke up a few hours later and was still spooning him. I was still horny and I realized my dick was still hard and still in his ass. So I just started to slowly fuck him again. This woke him up and it didn't take long before I started shooting again. And we fell back to sleep with me still spooning him. I woke up again a few hours later and my dick was still hard in his ass. So I just started to fucking him again. I shot my load and this time I pulled out. I had to take the cockring off because it was starting to hurt. I am not sure if I had been hard that entire time, but I cannot imagine I would have stayed inside him if I had gone completely soft. I never did do that again. I stopped messing around with him shortly after that weekend. I was developing feelings for him and he told me he already had a boyfriend (that was news to me) and wasn't wanting anything serious. He was a great fuck!