Where it happened: His house
This was really weird for me. I was asked to sit with my mom’s friends kid while his mom and dad when to a christmas party that was about an hour away. Keven was about ten or so and he could be a real smartass when he wanted. About ten o’clock his mom called and said they were stuck in a snow storm and can’t get home and asked if I could stay til morning. I said OK and called my mom and told her. Things were slowing down and Kevin came over and layed down on the couch next to me and we watched TV. He was dressed for bed in his underwear and a tee shirt. I was in my sweats. I don’t have much for boobs so I was just wearing the sweatshirt. I kind of got the feeling he didn’t get alot of attention. He was being very affectionate and sweet on the couch. We lightly hugged each other and periodically he would rub me lightly on my leg or back but for only a few seconds. Then by accident, he ran his hand a little under my sweatshirt. I know I should have stopped him but it wasn’t very far up my shirt. When he did it again and I knew it was no accident. This kid was feeling me up. We were watching Risky Business. Tom Cruise really turns me on. Kevin slowly worked his way up to my chest and I kept acting as if I hadn’t noticed. He was so gentle and cool about it and he moved so slowly. Then all of a sudden he pulled his hand out and stopped altogether. I could tell he was getting turned on by the movie too. He kept tugging at his underwear and when the light from the TV hit him just right I could see a bulge in his shorts that had to be a hard on but I didn’t think 10 year olds could get hard. Again he started gently up my top but he suddenly reversed and headed under my waistband. I put my hand on his and stopped him. He quietly said “OK, I was just curious” in his raspy voice and removed his hand. After giving it some thought I decided what could it hurt? He was just curious. I was kind of enjoying his company anyway. So I said OK. He waited a while before he got up the nerve to start over. The sweats and my panties were tight and binding and he was having a real hard time exploring although he was still being real gentle. So I decided to help him out a little and I pushed them down to the floor and kicked them off. I got a classic look of disbelief from him. I stretched out on the couch and he moved down to get a good look. I knew I probably shouldn’t be doing this. He gently moved my hairs aside and lightly touched me. He played around the outside for a long time and then began slowly exploring and gently massaging the inner rim and my clit. I knew we had to stop soon but I was really getting turned on. He was being so patient and gentle. I was on the verge of cumming for about a half hour as he explored deeper. He moved his hands up my stomach and slowly pushed my shirt up to my neck. He had pulled his shirt off and I began caressing his firm arms and back. He slowly moved further up and and over me and I moved my hands down his back. At the same time I noticed my hands were now down to his ass I felt his hard dick against my inner thigh. I was a scared when I discovered he was totally naked. I didn’t know what to do next. My heart was pounding and I knew this wasn’t possible. Without saying a word, he began gently pressing the head of his dick against my thigh while searching for the opening and I decided I wanted this to happen. I so hot and I didn’t care about whether it was the right thing to do. I reached down and moved his dick up and over and between my lips. He was only about four inches long but I wanted it bad. I grabbed his arms and told him to push, push harder. He held his breath and his whole body tensed as he pushed. He pushed his dick all the way in on the first try. He stayed there not knowing what to do I guess and I told him to slide out a little now back in. That was the extent of the lesson. He caught on real fast. His body shuddered within about half a minute or so and he was breathing real hard so I knew he had just cum but he kept going anyway. His thrusts were getting more confident and harder as he went. His dick fell out four of five times and I quickly put it back in. I came real hard real fast because he had me worked up in what turned out to be my best foreplay experience ever. He tired quickly because he was really thrusting fast and hard. I couldn’t beleive this was happening let alone with a kid as young and as bratty as Kevin. I learned alot about boys that night. I also learned how a small boy can be so much more mature than most of the 16 to 20 year olds I dated. We spent the remainder of the night together in his bed and in the shower. We fucked three more times before his parents got home the next afternoon. His mom gave me fifty bucks and asked me if he was good. I told her he was great. At least for me, the first time was the best. Not because it was the best sex, but because it was the best experience.