When I was around 12 my best friend and I were looking up porn and erotic stories to entertain ourselves. We read a story about boys who sucked each others cocks and generally fooled around. This got us into the habit of trading oral. Later we perused further and found videos of boys playing with dildos and getting fucked. We both experimented with fingering and small insertion. He did not like it, but I loved it. I tried and tried to get him to fuck me but he would not. We still played together weekly, but the only time I played with my hole was by myself in the shower.

By this time we were 13 about to be 14 and I thought about it a lot. I met a new boy who was at least 3 years older than me. He lived on the other side of the block. I had started talking to him while out biking one day. He invited me in to see his new nintendo. We played a wrestling game then wrestled some in the living room. I made a point to brush across his dick several times. He noticed and started leading with his crotch while we played. At one point he jokingly pulled it out and swung his semi hard dick back and forth. I jokingly got on my knees and dared him to do it. I closed my eyes and opened my mouth. I felt the tip touch my tongue. I think he expected me to pull back but I took his cock partially in to my mouth.

He pulled it out and said "shhh" even though we were not talking. He looked around to make sure no one saw, and then motioned outside. "I should go show you the old tree fort" he said. We climbed up and he shut the make shift hatch. He turned and sat on a stump used as the only chair. He pulled his dick out and started playing with it. I moved in watching, but waiting for instruction. He paused and kind of held it out. I took hold and slowly started stroking it. He asked if I enjoyed it, and if I had done it before, and who with? We talked for awhile and then I awkwardly blurted out that I wanted to try anal. I felt embarrassed so I hid myself by beginning to suck his cock. He laughed and put his hand on my head to speed up the rhythm. He went on to say that he had never tried it either but was interested in topping. I took my mouth off to ask about the meaning. He explained and I told him I think I am definitely a bottom. He laughed back then paused, so I put my mouth back on his dick and began jerking him off while running my tongue around the head of his cock. He said we could try.

I was so eager I didn't know what to do. He told me though, I guess he had thought about it before. Soon I was bent over with my ass arched back and out. He spit on his fingers and rubbed it on the tip of his dick. He set the tip against my hole and applied light pressure. I was almost there, and I pushed back slightly in anticipation. Tingling feelings and endorphins raced through my body as the first cock head pushed in to my ass. I could feel him pushing harder. Wanting to feel his dick all the way I tried to wiggle to let it slip in. Then his cock exploded with cum. I could feel it seeping out before his dick even started to soften. He tried to pump it even once but the semi flaccid penis was to soft to push back in my hole. Just like that I was no longer a virgin, and I was full of cum.

A few weeks later I met a guy online through CL. I told him I was not a virgin, and I was a bottom. I got picked up at a 7-11. I remember he pulled his dick out in the car and I was nervous because it was noticeably thicker. He had me stroke it for him and then took me to his house where he got me to get naked and had me take a shower so I could clean my self. He actually fucked me. I had no idea what I was in for. It was intense at first, but I was loving it by the time he blew his load in me. He bummed me a smoke and then started jerking me off slowly while fingering my now tender hole.