This happened in my sophmore year
Bobby was a geek. At least that is what I thought of him when he first walked in our class in the eighth grade. I was not alone in my thinking. All the guys in the class thought the same thing. All year long, we picked on him and called him all kind of names. I was on the baseball team. Somehow that seemed to make me superior. It seemed to give me the right to pick on the geeky guys. Bobby was the one that we talked about in the locker room. You know, whenever we wanted to insult one of the other guys. We would say that we saw him in the corner with Bobby.
The locker room was home to me. I had seen my share of naked guys. Most of us went through puberty together. We swam at my neighborhood pool. We would come home and all go to my bedroom and change. Sometimes we would goof around while drying off. We would check each other out and compare. It was not even embarrassing to get a 'woody' in front of the guys. We would make some smart-alecky remark and just go on. Sometimes we would joke about masturbation. Never would we admit to doing it. I think we knew that we all did. Publicly, though, it was a 'gay' thing to do. We were, however, comfortable with each other. In the summer following our seventh grade year, on a church camping trip, we decided to bathe in the lake, all together, nothing on. Our dads thought it was funny. It was kind of sexual, but in a 'straight' sort of way.
By the time we were in high school, Bobby was no longer the butt of our jokes. We had other things to worry about. We still thought little of him as a guy. It was in academics that Bobby was the star. Although we rolled our eyes when he would get the answers right, we would listen to his answers cause they were always right.
Bobby was a tall blonde, about six-one, and skinny. He always wore khakis and a golf shirt. He was always nicely dressed. I had only seen him once without a shirt. He was in the nurse's office. He had fallen and hurt a rib. His chest was a skinny boy's chest. There was no definition to his pecs. He had a little hair in the middle of his chest and a little around dime-sized nipples. I spoke to him and ask him if he was okay. He told me he was fine and thanked me for asking.
Report card time came around and the grade fairy had left me a sack of coal. My advisor told me that I would not be able to play baseball in the spring unless my grades improved. She advised me to get a tutor and gave me a list of several student tutors I could hire. Bobby's name was on the list. I asked her if he would be good. She told me that she had gotten good reports. I called him that night and he agreed to meet with me.
The first few sessions were in the library meeting room. Things were going very well. I was starting to understand my work much better. One day, we were scheduled to meet at the same place, but when we got there, we found the room occupied by the teachers. I told him we could go back to my place. He agreed.
At the house, my mom was using the table for scrapbooking, so we headed to my room. I decided to get comfortable. I went to my bathroom, took off my pants and shirt. I came back into the room and grabbed a shirt and some jogging shorts. It was nothing to me, but it seemed to make Bobby nervous. I said, 'Haven't you seen a guy in boxers before?' He said, 'Only myself and now you.' I apologized. Bobby accepted and we went on. He sat in my desk chair and I lay on the bed. He drilled me over questions for a test in history. After we were done, I got curious. I asked him about the girls in his life. He was quite candid in telling me that he had never had a girl friend. He had only chatted with a girl from England online. I expressed the opinion that it couldn't be any fun. He, once again, very candidly, told me that their chats were very much 'fun.' I asked how and he told me that they would describe themselves and what they would like to do with each other. I ask him if that left him horny. He said, 'only for a few minutes.' He left and my mind went to reeling.
The next day was Saturday. I went to the school to work out in the gym. As I passed the library, I saw Bobby tutoring another student. I waved at him and went on my way. After working out about an hour, I went to the snack bar to get a snack. Once again, I ran into Bobby as he was leaving. I asked him if he want to work out for a while. He was hesitant, but agreed. When we got to the workout room, everybody else had gone. I turned back on the lights and told Bobby to pick his machine. He did not know how to use the equipment, so I trained him on a few pieces. It did not take long until he was pretty sweaty. I told him he could take off his shirt. He did and continued to work. I asked if he had had a chat the night before with his English girl. He said that he had. I asked if it went well. He said very well. I wanted to know some of the things they said. He began telling me and I began to feel my dick starting to tent my jogging shorts. After a few minutes, he glimpsed down and saw it. His eyes got really big and he got quite. I said, 'What's wrong dude?' and he said' 'Doesn't that embarrass you?' I told him, 'Not really, we are two guys and it happens.' I could tell he was getting tired. I grabbed my towel and told him I was heading to the shower. He asked if he could use the showers, too. I said sure and he followed. I did as I always do. I got naked and walked into the shower room. He hesitated and wanted to know if there was a private shower? There was not one. I told him to just get in. He dropped his pants and came inside. He kept his back to me as we showered. We were still talking and he would turn his head. I was fully erect thinking about our conversation.
Now I was at the time about seven inches erect. My shaft pointed straight up. It was bothering me a little and it apparently bothered him a lot. I remembered what he said about not being horny for long after his chats. I knew what he meant, but I asked him anyway. He said that he masturbated. I acted like a stupid jock and led him to believe that I did not know what that meant. He told that he would rub it until it ejaculated. I told him to stop using such big words and to show me. I was really joking, but he turned around and said, 'okay.' I just couldn't stop him.
He had about eight inches of hard dick. Although he was blonde, his pubes were dark and he had quite a bit. He balls hung way down. Mine stick pretty close. As he stood there pumping his rod, his balls swung back and forth. I had never seen anything like that before. Pretty soon, I was aping him. Slowly and methodically I was moving my fist up and down my shaft. I was watching him. I could see him getting close. Then his body jerked and he squirted out three or four ropes of cum. I watched it as it went down the drain. And suddenly without much warning, I was oozing. It was so hot. Nothing had ever felt that good.
Bobby went to dry off, quite and nervous. I followed. I asked him if we could consider that a 'private lesson?' He agreed and said that it would be no charge. I wanted to have another lesson, but the opportunity never came up. I was afraid that trying to make it happen would come across as gay.
I did tell my best friend about it one night a few months later. He said that he had wanted to jack off with me for a long time. That will be another story.