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.