My first time was when I was 15 with a boy who was the same age in our tree house up above my parents house. He was one of my best friends and we would hang out in the tree house all the time. Him and one other friend used to bring Playboy and Penthouse magazines that they had stolen from their dads to the tree house. When they first started doing that, we would all just sit there and talk about them and laugh. They would get aroused and start to rub there crotch area over their pants. I was shy at first and I can remember focusing more on the hot guys in the pictures that were having sex with the women rather than at the women themselves. This went on for several weeks until late one evening one of the guys started to rub the other ones crotch. And then he (Josh) in turn started to rub mine. I guess it was like a circle jerk with only crotch rubbing. It later progressed to each of us sucking the other person off. Not shooting him in the face but just getting close and then jerking off to completion. We started doing that everytime we hung out in the tree house which was every other day. Eventually I talked my mom into letting me spend the night at Josh's house. The other guy just sort of ended up falling out of the circle of friends.
The first night I spent at his house I slept in his bed and him in the floor in his room. I noticed before we layed down that he had locked his bedroom door. We layed there for a few minutes talking about random things until he stated that the floor was too hard for him, and I either needed to trade him or let him lay beside of me laughing as he said it trying to pass it off as a joke. I told him that I didnt care if he got in the bed with me, and that it was big enough for both of us laughing as well. He said "Fine, if youre not going to trade, I'm laying up there with you." We lay there for a few minutes side by side, very awkwardly. Then he started to tell me about a girl that he was talking to at school and how he was going to bring her home one night and "fuck" her. He was pretty vulgar about it and the thought of it made me a little sick, but i noticed it aroused him. He started to touch himself just like before in the tree house. Then I started to touch myself as well. It went on for a little while until he started to rub my crotch like before, and I did the same to him. I could tell it was going to lead to more oral action like it had always before in the tree house, so i pulled down my pj bottoms and he did the same. I started to suck him off, and half way through he told me to stop for a second. He put his pj's back on and went to the bathroom. I thought for sure that he was no longer interested at that point and that the whole thing had gotten way too intimate or whatever.
When he came back and layed back down to my surprise he pulled his pj's back off and then from one of the pockets he pulled out a small bottle of moisturizing lotion. I was for sure that he just wanted to jerk off with it and had no idea of his intentions. He started rubbing it on his cock. he closed the lid and dropped it in the floor beside the bed. I was a little confused until he told me to turn onto my stomach. My confusion suddenly changed from scared, to excited, and then back to scared again. He didnt ask me if I wanted to but he didnt have to. I was so curious and hard that i didnt care. I wanted him so much that it overshadowed the fear.
I lay there on my stomach trembling from fear, nervousness or excitement, im not for sure which. Maybe a combination of all three. Then he strattled me, one leg on each side of my ass checks. I could feel the tip of his head touching my cheeks and then start to press in between them. I was afraid to stop clenching and at the same time afraid to keep clenching because i didnt want him to think that i didnt want to do it, because i wanted it so much. I wanted him. So i relaxed my ass a little and i could feel him start to enter my hole. I had to grab the side of the bed to keep from screaming from the initial pain. He slid into me, and not even slow at first. He just started pounding me like he didnt care if it hurt me or not. I was practically in tears but I wanted it more than anything. He started pounding so hard and so fast, and then even started to pull my hair. My ass started to go numb from the pain of having him inside me. I stopped focusing on the pain and on him on top of me pounding and enjoying it. He put his face down to the side of my face like he was holding me and protecting me from something and i glanced to the side at his face and could see how much he liked it and wanted me too. He just kept pounding and fucking me, not slowing down even once. I reached around and grabbed his ass cheeks and pulled him in further. Making him pound as deep and hard as he could. It didnt hurt anymore it felt great. It lasted for about 10 - 15 minutes. I came about halfway through with him inside