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 mind, 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.
This all happened I was a fifteen-year-old delinquent that was skipping class and always hanging out at the local game room by the high school. After a short time, I had started to become good friends with a man that was slightly older than I was and I found out he was actually the owner of the game room near my high school. Everyone at the school liked to hang out there during the day and even into the evening some days. I did not really notice him to much at first, but I think he must have been watching me, and noticing all the time I was spending at the game room, and I think he must have decided to see if I could be encouraged to have a relationship with him.
It all started out fairly innocent at first and our conversations were nothing more than asking for change or the casual, “Hello” as I entered the game room. However, it progressed to give me free games on the pinball machines when I was hanging out there and in time, it grow into him asking me to go out for breakfasts and lunches on from time to time. Somewhere along the way, I even started receiving pot and pills from some of the older guys that worked at the game room. I was actually enjoying skipping classes to hang out at the game room, it felt like a home.
When we would go out for breakfast or lunch, our conversations were innocent on the surface, but I am quite sure he was trying to get a feel for the situation and trying to build me up and find out if I would be willing to have sex with him. There was one particular day, when we were out for breakfast, our simple conversation turned to a conversation about sex and girls, and he asked if I had ever been with a girl. At the time, I had been with several girls but I had not gone all the way. Then the conversation ultimately turned to one about homosexuals and if I ever found other men attractive or if I had ever thought about having sex with another man. I of course said No, that I had never been attracted to other men and that I would never have sex with another man; I was only attracted to girls. I still felt that the conversation was rather innocent, but it was about to turn. He then mentioned that he was bisexual and asked if I know what that was. I had never heard that word 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. He then explained that he like having sex with women but sometimes he enjoyed sleeping with men 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 and then he told me that he was attracted to me and that he wanted to sleep with me. I suddenly felt very uneasy with the situation and I think he knew it too. I did not know what to do and this man was my only way back to school. He then told me not to worry, that he was not going to do anything unless I felt the same way, but he wanted me to know how he felt. I was speechless and did not know what to say and I think he knew the subject made me nervous. We soon left the restaurant and headed back to the game room. In the car, he pressed the issue a little more and told me he hoped I would think about it and he told me that he would give me anything if I would sleep with him. He mentioned money, girls, and even a car. I was silent all the way back to the game room and when we got there, he said to please think about it and to let him know what I would like to do it with him. I told him that I would think about it but at the time, it did not sit well with me about having sex 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 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.” In the car on our way to the restaurant, he asked what it was that I would really like to have. I told him nothing and he was hard-pressed 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 much, but I felt that he wanted to continue to find out what it would take to get me in bed. Eventually, I told him that I would really like to have a car. He smiled and I knew I had given him the opening he was looking for and he asked what kind of car I would like to have. I told him I was not sure, but he needed to keep this open and he kept probing to know what kind. 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 possibly having sex with me. We left the restaurant and as we were driving back to the game room, he said to let him know what kind of car I would like to have and that he would get me whatever kind I wanted. The conversation seemed to become innocent again; I tell him what kind of car I want and he will get it for me, no strings attached. However I was only thinking about having a car and not thinking that when I tell him what I would like that I was also giving him the opportunity to possibly have sex with me, and not just once but many times. When we pulled into the parking lot, he reminded me to let him know what kind of car I would like. 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.
He had really got me thinking about what kind of car I would like to have and as I thought about all the different kinds of cars, one that I kept coming to mind and it was a 1956 Chevy, but what would happen if I actually went though with it and told him? I was not sure, but the next day when I went over to the game room, there he was and he came up to me and asked if I had made a decision. I was unsure as to how to answer, but I said that I had made a decision. He 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 said he would get right on it.
A few days later, he came up to me and told me he had found the car and that we should take a drive and talk about it. He was very good and in the car, he said he had seen the car, it was very nice, all it needed was to be painted, and that I could have it in a week or so. I was so excited to see it and drive it, but now he had a question for me. He said that now that he had the car I wanted what I would do for him. I did not know what to say and I should have realized there was a catch to this whole thing. He said, “I will tell you what, you come over to my place with me tomorrow afternoon and try it, if you don’t like it, I will stop and we will leave and you can still have the car.” We returned to the game room and he told me to come by tomorrow and let him know what I want to do. I was eager to have a car and worried about what would happen at his house, but I was curious 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 it was taking 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, let’s just go do it.” We pulled into an apartment complex not far from the school and parked out front of an apartment, and went inside. I noticed his apartment was nicely furnished and clean looking and as I looked around, he proceeded to close the blinds in the front room and then we went into the back bedroom. As we walked down the short hallway, I noticed a bathroom in the hall and across from that; there was another bedroom with the door closed. As we entered the back bedroom, he closed the blinds. It soon became rather dark in the room, but some light did manage to come in through the closed blinds. It was a quite large bedroom with a bathroom toward the back and a king sized bed. He sat on the edge of the bed and motioned for me to sit next to him by patting the bed. He put his hand on my thigh and rubbing it, told 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. He said he would be right back as he went into the bathroom presumably to take off his clothes as I sat there quietly for a second. I then thought that I had better started undressing before he returns and I took of my shoes, my shirt, pants, and my socks, and piled them at the end of the bed. I felt it was important for some reason to keep my underwear on though. I sat there for only a few seconds, and I heard the door to the bathroom open and he came out with what appeared to be only a long sleeved, button down shirt on. He walked over and sat next to me. He noticed that I still had on my underwear and asked, “What’s wrong?” referring to me still having my underwear on, and I said, “What?” He dismissed it and told me to lie down on the bed, near the edge and facing the wall. He came around the bed and knelt on the floor in front of by me. I started to rub my body and legs and the spread my legs, rubbing my cock through my underwear. I was trying to distance my thoughts from what was going on and thus I was not hard. He started to take off my underwear and asked me to help him get them all the way off. I laid back down a he tried to get my dick hard by rubbing my cock and balls. He eventually tried sucking my dick but I think because I was trying so hard to distance my thoughts, my dick would get hard. He stopped sucking and stroked it, asking me if it felt ok and for me to help him get it hard. He started to suck my cock again and I was trying to let it get hard for him, because I knew he was not going to let me go without cumming. I thought about getting hard for him and cumming in his mouth. It started to feel good in his mouth and I was now starting to get hard as he sucked and stroked my cock. He kept stroking my cock and occasionally he would rub my balls and finger my ass. Now I was really into it and as my cock grew harder, I could feel myself about to cum in his mouth, but I was not very hard yet. I tried to hold back until I was all the way hard, but I could not. I let it go, cumming in his mouth prematurely and I think it surprised him. I could feel my cock throbbing in his mouth and him sucking for every drop. My cock almost immediately went soft while still in his mouth and 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.” As he got up off the floor, he told me to move over into the middle of the bed for him. I laid there on my stomach not know what he wanted and as he walked to the end of the bed behind me, he told me to get on all fours, like a dog and move up toward the head of the bed. I could feel him getting on the bed behind me now and he told me that I would need to relax now. I could feel him inch closer and he told me to put my head down on the pillow and spread my legs a little. I could hear something that sounded like he was rubbing lubricate on his cock and then he told me again to relax and I felt him start to rub my butthole with lube too. He put a finger in my ass and started fingering my ass and he said,” Oh, you’re nice and tight.” 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 my tight ass. 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 trying to moving his cock in and out of me. After a short time, he again asked if I was ok and he started really moving his cock in and out fast and fast. My cock was getting hard as he moved in and out of me and it even started to feel good having moving in and out of me, but suddenly I could tell he was frustrated and he stopped. He explained that I need to help too and that I needed to move back and forth with him. I should push back when he pushed forward and then pull forward when he pulls out. We tried again and he said, “That’s it, keep going.” I did and it felt good this time and I was really trying to get into it. He even reached around me and played with my now hard cock as he was fucking. Then he quit playing with my cock and tried to do shorter quick strokes as he was fucking me. It was hard to keep the same action going, but then all of a sudden, he pulled me close and his , don’t cock went way inside me and it hurt. I tried to pull away but he held me close and out of breath he said, No, don’t move!” I now knew he must be cumming in me and could feel his hard cock jerking inside me. He was now out of breath and he hunched over me, slowly moving his cock in and out of me again. He kissed me on the back and told me how good it felt and asked me if I liked it too. When I did not say anything, he pulled his cock out of me and told me that I had better go into the bathroom and clean myself out. He told me to use the hall bathroom and to come back to the bedroom when I was finished. I got off the bed and hurried into the bathroom. I was not sure what he meant by cleaning myself out, but I sat on the toilet and wiped my butt and tried to push out whatever was inside. I managed to push out some KY jelly and what looked to be cum, but I was not sure. After a few minutes, I returned to the bedroom where he was waiting for me on the bed. He told me that he really liked making love to me and that he wanted to do it again. I told me again to get on all fours with my head down and he again got on the bed behind me. It put some more KY around my butthole and in my ass too, and told me to relax again. I wondered how he could be able to do it again after cumming just a few minutes ago. I tried not to let him penetrate my ass again, but his hard cock seemed to be able to penetrate my ass more easily than before. I did not want to do it anymore and I decided that this time I would not help by moving back and forth, as he fucked me. He noticed almost right away and asked what was wrong? I told him that I did not want to do it anymore. He reached around taking my hard cock in his hand and said, “Come, I thought you liked it.” “Let’s do it one more time.” He tried fucking me but it did not work. As he was trying to fuck me the second time, I thought that it actually felt good, but he had told me we would only do it once. He told me to go clean up again and to go ahead and get dressed. He in turn went into the bathroom to get dressed as I sat there on the bed. When he came out, he sat by me again and told me, how nice it was making love with me and he asked if I would like to try it again sometime. I was again once again powerless. He was my ride back to the game room and I did not know what to say, so I said nothing. We left the apartment and drove back to the game room. I could still feel his cum oozing out of me and when I got home, I showered and tried again to push his cum out of me.
A few days later, I returned to the game room to ask about the car he had promised me and upon asking him about it, we got in his car and drove around. He explained that the deal was to do it more than once and that I did not do my part so the deal was off. I was in shock. He said if you want to do it again with me, we could consider the deal back on again, but only if we were to do it again. I did not know what to say. I wanted the car, but did not want to have sex with him again. We went back to the game room and he said, “I still have the car and if you want to try it again, I’ll give you the car.” I stayed away from the game room for a long time and when I did return, we were friendly, but it seemed that he was still looking for an opening to continue the relationship, and maybe in a way I was too. He mentioned to me that he was moving closer to me and I did visit once, but felt uneasy when I entered his apartment.
The car never materialized and I never again had sex with him. I did try to contact him much later, but never did find him. I have wanted to try it again, but these days, it could have deadly consequences.