A Fateful Day

The encounter that I am about to tell has stuck in my mind and I have for so long tried to put it out of my thoughts, but periodically I find myself slipping back and remembering this particular time. This all happened many years ago, but when I think about this one time, it feels like it had just happened. It may be that I wish it would happen again or that I could somehow go back and relive the experience all over again. I have mixed feeling about it, but when it creeps back into my thoughts and I end up thinking about what actually took place, it seem to go back to that fateful time in my life but then I wish again to forget.

It actually began in early spring when I was a fifteen-year-old delinquent, skipping class and hanging out at the local game room by the high school. I had been hanging out at this game room for quite some time, when I started to become good friends the owner of the game room. His name was John and he had dark hair; dark skinned and, he was much older than I was.

Many students would hang out up at the game room during the day and sometimes into the evening. This was a place to meet friends, play games, and just hang out if you did not have anything else to do. It was also a place where you could find drugs and alcohol, if you wanted it, or to hook up with someone. I did not really notice John to much at first, but I think he must have been watching me. He probably noticed the amount of time I was spending at the game room and during this time, I think John must have decided that he would see if I could be encouraged to become friends and maybe even build a relationship with one another.

Conversations with John wee innocent. I would ask for change to play the games or sometimes a casual, “Hello” when we saw each other. As time progressed, John would sometimes give me money to play on machines when I was hanging out there and our friendship eventually grow into where he would take me out for breakfast and lunch. It was definitely nice receiving this attention and I enjoyed skipping classes to hang out at the game room. When we would go out for breakfast or lunch, our conversations were always very casual, but I now know he was getting a feel for the situation and as I would later find out, he was actually building this friendship in hopes of have sex with me. John must have become a little impatient and felt it was time to test our friendship. One day, when we were out for breakfast, our simple conversation turned to a conversation about sex and girls. John asked if I had ever been with a girl and at the time, I had been with several girls but I had not gone all the way with any of them, so I said, “Yes”. We talked about what I was attracted to and he did the same, but using this line of questions, John turned the conversation to one about homosexuality.

He was trying to find out what I thought about homosexuals and if I ever found other men attractive. I told him that I thought it was wrong and I never looked at other men that way. John then asked, “So you have never slept in the same bed with one of your friends, not having sex, but sleeping together?” I said, “Well, yes but that is different,” and I told him that I was only interested in girls. I still felt our conversation was rather innocent, but it was about that was all about to change. John then mentioned that he was bisexual and asked if I know what that was. I had never heard that term before and he seemed to relish the opportunity to explain that he was attracted to women and that sometimes he found men to be attractive too. I was not sure where this was leading, but John explained that if he found a woman to be attractive and she found him attractive, they sometimes slept together and would have sex. He also said that sometimes when he found another man to be attractive, and that person was attracted to him, he enjoyed sleeping with that person too. I was kind of in shock and he continued the conversation by asking what I thought about that, and I told him that I was not sure how I felt. John now had the opening he was looking for and he explained that he found me to be someone he could really talk to about stuff and that I nice looking too. I did not know what to say, but he proceeded to tell me he had thoughts about wanting to sleep with me, not to have sex but to get closer to each other. This was a bold move on his part but it would ultimately tell him if I was interested at all in having sex with him, and it did pay off for him in the end. I did not know what to do or what to say.

I was somewhat flattered that he thought I was good looking, but to sleep with him, I quickly said, “No, I had never thought about sleep with him.” John then said, “We wouldn’t have to do anything, we can just lie in bed together and see how it goes.” I was silent. What was I going to do? This man is talking about wanting to sleep with me and he is my only way back to school. I was feeling very uneasy with the situation, and I think he knew it too. To relieve some of the stress, John said, “Don’t worry; I am not going to make you do anything you don’t want to do.” He was trying to smooth things out now, because he realized that he had pushed the conversation to fast. He now needed to make sure I was still open to spending time with him to make sure the opportunity was still there, before we left the restaurant and he wanted to make sure I was thinking about it, because if I was interested at all, the next offer he was going to make might just change my mind.

I was speechless and did not know what to say and I think he knew the subject had made me nervous. He again told me not to worry about it and as we left the restaurant, he held out his hand in hopes that I would shake it. I quickly shook his hand and we headed back to the game room. As we drove, he continued to try to smooth thing out and to make sure everything was still ok between the two of us. However, his real motive was to convince me to sleep with him and to change my mind about it or at least encourage me to keep thinking about it before we got out of the car. John told me that he hoped I would think about it and he then explained that he would give me anything if I would sleep with him, anything. John mentioned giving me money, having girls for me, buying me something. He even told me he would buy me a car. I was silent all the way back to the game room and when we got there, he asked me one last time to think about it and to let him know what it would take to change my mind. He was not going to let me out of the car until I had given him an answer, so I told him I would think about it but at the time, it did not sit well with me about sleeping with another man, but I did think about it.

A few days later, I ventured back to the game room to hang out with friends and he eventually cornered me and asked if I had thought about his proposition. I told him that I had thought about it but I was still unsure about it. He said, “Come on let’s go get something to eat.” Right then, he knew the opportunity of having sex with me was still there and in the car on our way to the restaurant, he said, “I am so glad you are thinking about it, and you have been such a good friend, what can I get for you for being such a good friend?” I just wanted to keep this on a friendly basis, so I told him I was not sure, but he was hard-pressed now to get an answer and again asked, “Come on, there has to be something you would really like to have.” At the restaurant, we did not really talk about it much, but I knew he wanted to find out what it would take to get me in bed. He again said, “You have been such a good friend, what it is I can get for you?” I knew he was going to keep pressing for a response so I told him that I would really like to have a car. John smiled with confidence and I knew I had given him the answer he was looking for. He casually asked, “Oh yea, what kind of car would you like to have?” I told him I was not sure, but he knew that he needed to keep this conversation going now, because he was almost there. He kept probing to know what kind of car I liked and he asked if I liked Camaros, Firebirds, Mustangs, etc. and I told him I was not sure what kind I wanted.

He did not want to lose this chance of getting me into bed, so as we drove back to the game room, he said to be sure to let him know what kind of car I would like to have and that he would get it for me. The conversation on the surface seemed to become innocent again and he made sure that I understood to let him know what kind of car I wanted and that he would be sure to get it, no strings attached. When he told me, No strings attached, I was seriously thinking about what kind of car I would like and not thinking that if I do tell him would I want that I would be giving him the opportunity of sleep with me, and not just once but maybe a few times. When we pulled into the parking lot, he made sure to remind me to let him know what kind of car I would like and I said I would and he immediately asked if I would be able to tell him tomorrow. I told him I would try and we got out of the car and went inside the game room.

John really had me thinking about what kind of car I would like to have and as I thought about all the different kinds of cars, but one kept coming to mind. It was a 1956 Chevy. However, in the back of my mind I thought, what would happen if I actually went through with it and told him? I was not sure, but having a car would be nice and he did say there would be no strings attached. A couple days went by before I went back up to the game room, and I tried to avoid John as best as possible, but he came up to me and asked if I had made a decision. I was not sure if I should answer, s I hesitated for a second and then I said, Yes, I had made a decision. John said, “Great, let’s go for a drive and you can tell me!” He was obviously excited as we left in his car and I told him that I would really like to have a ’56 Chevy. He told me that he would start looking for one. I then told him that I wanted it to be a two door with a V8 and I would like it to be midnight blue. He knew he had me now, all he needed to do was reel me in and he said he would get right on it.

A few days had passed, when one day I was up at the game room he came up to me and told me he had found the car and that he wanted to tell me about it. John was very good at building up the situation and as we drove, he started to describe it to me, and it sounded exactly like what I wanted. He told me that it just needed to be painted the mid night blue I wanted and that it was going to be ready it in a week or so. I was so excited and I wanted to see it and drive it, but now he had a question for me. In the back of my mind, I knew it was coming, but what could I do now. He said, “Well, now that I have found the car, what are you going to do for me?” I did not know what to say. John then said, “I will tell you what, you come over to my place with me tomorrow afternoon and give it a try. I was not sure at first what he was suggesting, but realized he wanted me to sleep with him. He then said, “If you don’t like it, we can stop and leave, and you can still have the car.” He also said, you think about and let me know. I was not sure, but said I would think about it and he patted me on the leg. We returned to the game room and he told me to come by tomorrow and let him know what I want to do and I agreed. I was so excited to have a car, but in the back of my mind, I was thinking about what might happen when we got to his place, but I wanted that car and I decided I would do it.

That night, I started to think about what was going to take place the next day when we went to his place and I knew I had better be ready for anything. My first thought was, “What if I end up cumming tomorrow?” I had not masturbated for a few days and I knew the next time I was to cum, it would be a lot. I did not want to cum to much for him tomorrow so I decided I had better relieve myself and that by tomorrow, I would still be able to cum for him. Then I thought about my ass and if he puts his finger in me or his cock in me, I did not want him to think I was not prepared so I made sure to take a crap before I left that morning for school and clean my ass real good too.

The next day, I went up to the game room around noon and was nervous about what was going to happen, but all I could think about was that car he promised. He came up to me and casually said, “Are you ready?” I simple replied, “Yes I am ready.” He said, “Are you sure?” I told him that I was sure. We got in his car and headed off to his place. I was not sure where we were going and I was very nervous as we drove because I knew where this was leading me. Along the way, I think to break the tension, he asked if I was hunger and if wanted to get something to eat first. I said, No, I just wanted to get over with it. We pulled into an apartment complex not far from the school and pulled in front of an apartment, and went inside. Inside, his apartment it was small, but nicely furnished and clean looking, and as I was looking around for a place to sit, he closed the blinds in the front room and then we went into the back bedroom. As we walked down the short hallway, I noticed there was a bathroom in the hallway and across from that; there was another room with the door closed. As we entered the back bedroom, he quickly closed the blinds, making it rather dark, but some light was able to slip past the closed blinds. It was a large bedroom with a bathroom toward the back and he had a king sized bed. He sat on the edge of the bed and motioned for me to sit next to him. He put his hand on my thigh and rubbing it, and telling me to relax and that everything would be all right. I simply nodded and he told me to go ahead and take off my clothes as he stood up and started walking toward the bathroom. He closed the door to the bathroom and I sat there quietly for a second. I then thought that I had better get undressing before he returns.

I took of my shoes, my shirt, pants, and my socks, and piled them at the end of the bed. I decided I would leave my underwear on and I sat there waiting. Hearing the door to the bathroom open, I looked over to see him come out wearing nothing more than a long sleeved button down shirt that appeared to be unbuttoned. As he walked over to the bed, I tried to see what his body looked like and especially how big his cock was, but his shirt covered everything. John then sat next to me and noticed I still had on my underwear. He asked, “What’s wrong?” referring to me still having my underwear on, and I said, “What do you mean?” He dismissed it, realizing I was nervous about being there and he tried to lean over toward me, apparently trying to kiss me but I turned my head. John then rubbed my shoulders for a second and told me to go ahead and lay down on the bed, near the edge. He had me face toward the window as he came around to that side of the bed and knelt on the floor by me. He had me lay on my side and he started by rubbing my chest, stomach and legs. He moved me closer to the edge of the bed, spread my legs apart and started rubbing my cock through my underwear. I tried to distance my thoughts from what was going on, but as he was trying to take off my underwear, he brought my thoughts back to what was happening by asking me to help take off my underwear. As I lay back down on the bed, he started fondling my cock and my balls.

He took my soft cock in his mouth, sucking it, but because I was trying to distance my thoughts, I was not getting hard for him. Frustrated, he stopped sucking and asked me if it felt ok. I told him yes, and he asked me to help him get my cock hard. I agreed to try and he started to suck and stroking my cock again. I tried to concentrate on getting hard because I knew John was not going to stop until I cum for him because that would tell him I was willing to go all the way with him. After awhile, my cock started getting hard as I focused on trying to cum in his mouth, and it was actually starting to feel good too. As I got harder, he must have felt it harden because he started stroking my cock as he sucked. It really felt good and as I got close, he started to finger my ass. This really felt good with my cock in his mouth and him fingering my ass at the same time. I knew there was no turning back for me now and soon I could feel myself near to cumming. I was ready to cum but I was still not fully hard, so I tried to hold back, but then I just wanted to get it done and I decided it was time to cum in his mouth. When I came, I think it surprised him at first, as my cock started to buck and dribble cum in his mouth.

He continued to suck and pull on my cock but it was all ready starting to become soft while still in his mouth. He disappointedly said,” Is that it?” I said, “What?” and he quickly said never mind and asked if it felt good. I replied with a simple, “Yes.” He told me to lay on my stomach in the middle of the bed as he got up off the floor. I moved to the middle of the bed for him and laid there on my stomach. He was now at the end of the bed and he told me to get on all fours, like a dog and move up toward the head of the bed. I could feel him climbing on the bed behind me now and he told me that I would really need to try to relax. I could feel him inch closer to me and felt him start rubbing my ass. He told me to take a pillow out of the bed and put my head down on it. He then told me to spread my legs a little and arch my back. I could hear him stroking his cock lubricate and then told me again to relax. I felt him start to rub my butthole with lube and he slipped a finger in my ass and started fingering my ass a little. He asked if it felt ok and told me how nice and tight I was. He then asked if I was ready and I replied, “Yes.” He also told me it might hurt a little at first but that I should try to relax. I could now feel his hard cock against my butt hole as he tried to penetrate me. It was ok at first, but then it really started to hurt and he asked me if I was doing ok. I told it hurt and I tried to pull away from him, but when I rose up on all fours he took his cock out of me and as he did, he told me, ok and he also said that I needed try to relax more and that the hurting would eventually stop, but that I needed to relax. He said to tell him when it stopped hurting, of course so he could try again. It hurt for a little while, but I tried to delay him putting his cock in me as long as possible. He asked a couple times if I was ready to try again and finally he had waited long enough. He said, “Ok. Let’s try again, but this time I really need you to try to relax this time when I am in you.” I agreed and he put more lubricate on my ass and proceeded to push his hard cock in my as again. Again, it hurt and I tried to have him take it out, but he refused and held on to my hips, keeping his cock in me. He then asked how I was doing and if I was doing ok. I replied that I was ok and then he started moving his hard cock in and out of my tight hole and when he did, it started to hurt again. I told him it was hurting again and he just told me to relax. I rose up and tried to wiggle free but he again held me tight and kept his cock moving slowly in and out of me.