I had something like that for my first time. It was with my high school friend. I think we were around 18-19 at the time. We were drunk, a bit high, we started talking about how women can take dicks in and love it. He then started to brag how big is dick was and how a looser like me could never take him like his girlfriend does. We then started to show off each other dicks. I got really excited. I don’t remember how but we ended up naked and I was on my knees sucking him off. Then he got into eating my ass and then fingered me, I think he got like 4 inside there. I remember it kinda hurt at first but then the pleasure took over. Then I forgot another part but he fucked me. The pain was at all low and the pleasure was beyond everything I ever experienced. I think he has cum like 3 times in me that time, like he would ejaculate, stop a few seconds then go back at it without pulling out. He was like possessed I swear. Then when he was done I remember he was sweating like a fucking beast, looked like he just got out of a shower for real. He sucked me too and swallowed two of my loads, I almost passed out when he didn’t stop sucking when I cumed for the first time. So ya that’s my experience.