First time I had anal sex was when I was a young teen, with one of my good friends. I remember we found his older brothers penthouse and were mesmerized then naturally curious. We didn't know what to do so we both kind of of just rubbed ourselves over our shorts. I don't think either one of us came. We stopped when we heard his mom get home. Later we talked about the magazine and somehow talked about how one of the pictures the woman was getting fucked in her ass. I don't remember how we got talking about wondering how it would feel but I remember him asking if I might want to see.
The next day I went over to his house and told him let's try. We grabbed a blanket, some baby oil and went to the woods by his house. We found a nice spot with a bush we could crawl in, set the blanket down. I took my shorts off and he started rubbing the lotion on his finger and he fingered me. It felt weird at first, a little painful but also nice. After awhile he asked me what I thought I told him it felt good. He asked if I wanted to try it more? I told him yes and he got naked and I took my shirt off. We looked at the magazine and I got into the position the woman was in, on my hands and knees, and I felt more lotion on my ass and then pressure. Lots of pressure until pop he was in. I almost screamed and cried.
It wasn't long before he was fucking me and of course it didn't take long until he came. I didn't even realize that I had came too.