All characters are over 18 and consenting adults.
In the first part of this story, my two friends and I had graduated high school and were spending our summer together. Brent, Joe and I had spent a day and night getting to know each others bodies. This was our first time experimenting with male on male sex and we all enjoyed what we had done so far.
The next day we all went to work, since we were still trying to save money for college, but agreed to swim later. We met at Brent's house and swam before dinner. After Brent grilled some hamburgers for us, we jumped back in the pool. We swam and splashed and hung out around the pool the rest of the evening. When the sun went down and since Brent's parents were out of town, we felt free to remove our swim suits.
We swam and occasionally grabbed each others dicks. After a couple of hours, we slipped out of the pool and went down to Brent's room. He lived in the basement and had a waterbed. Joe agreed to sleep on the floor and Brent and I would share the bed, for now.
Since we were already naked, as soon as we laid down took about two seconds for Brent to find my cock and start rubbing. I reached over and took his cock in my hand. It felt nice and warm and grew quickly. Brent's cock was smaller than mine and I could only use two or three fingers to grip him. I would be happy about this later. Joe heard us and jumped in beside Brent and said "hey, I want to play too." We picked up just like our first time. Except this time I had a hold of Brent, Brent had a hold of me and Joe was free to enjoy.
I lay there thinking about what we were doing and had a thought. I heard jokes and stories of men screwing other men in their butt. I felt a twitch in my ass and got very excited by this thought. I rolled onto my side and slid my ass over so it was next to Brent and he began to rub massage my ass. His hand rubbed my butt and then he would slide a finger down my crack until he found my hole. He would pull back like he was afraid of where this might lead. Each time he would slide a finger down to my hole, I let out a moan. Just to let him know I was ok with it.
After the third or fourth time he touched me and I moaned, Brent turned to Joe and said "I think Brad wants to butt fuck." This must have excited Joe because I heard him cum quickly. Brent rolled over next to me. Then I felt his hands on my ass again but this time when he reached my hole he rubbed something warm on it. Then It hit me, he had scooped up Joe's cum and was using it as lube. Then I felt him put his cock in my crack and start moving down. We had never done this before, so I grabbed his cock and helped him find my hole. I lined him up with my entrance and pushed against his cock, to encourage him.
Brent started pushing but stopped quickly. I told him "I'm ready just keep going." He pushed harder and harder. I felt a little pain but relaxed just a little and in he went. Once he was all the way in, I took a breath, and said "yeah, keep going." He started slowly moving in and out. I'm not sure if he was moving slow because he didn't want to hurt me or if he didn't want to cum too fast. This is when I realized, I loved his dick in me and wanted it again and again. I also knew we would be doing this the rest of the summer.
Brent continued fucking me and Joe kept looking over Brent's shoulder to watch. Brent was giving me so much pleasure that I got harder and harder the longer it lasted. I lost track of how long we fucked but Brent started grunting to let me know he was almost there. I told him "It's ok, just cum in me, I want you to." He grabbed my hips and pushed into me one last time and came. I could actually feel him pulsing in my ass.
Joe was watching and said "wow, when can I do that." Brent pulled out and rolled onto his back. Joe couldn't stand it and came around the bed so he could lay next to me. Joe saw my cock and how hard it was and began to jack me off. I was so excited from the ass fucking that I didn't last long. I put my hand on Joe's shoulder to encourage him. He licked his hand and then started sliding up and down on me. I couldn't take anymore and began to cum. I shot all over my chest and some hit my cheek. Joe just keep pumping until every drop shot out. "Wow Brad, I like watching you cum," Joe said.
As we all laid there, exhausted and relaxed, a thought hit me. I had just had my first ass fuck and now had two of my friends cum in my ass. Joe's, as lube, had been pushed in by Brent and then Brent came in me as well. This thought would be the fantasy of many masturbation sessions throughout my life. Even now, thirty years later I still use this memory when I jack off.