Fateful encounter

The encounter that I am about to tell has stuck in my mind even though I have for so long tried to forget it, I from time to time find myself remembering and slipping back to when it all took place. This all happened many years ago, but when I think about what happened, I feel as though it has just happened and I want to experience it again. It was a memorable affair in my life that I wish could happen again or that I could somehow go back to experience it all over again. When I think about what happened, I have mixed feeling about it, but whenever it creeps back into my thoughts it takes me back and I remember everything that happened, but then I wish again to forget it ever happened.
It all happened when I was a eighteen-year-old delinquent that was skipping class to hang out at the local game room that was by the high school. It did not take long before I everyone working at the game room knew me and I had become good friends with the owner. He was a man that was much older than I was, dark skinned, and very friendly and for this story, we will call him John. Everyone at the school liked to hang out at the game room during the day and even into the evening, some times. It was strange because at first, I did not really notice him to much at first, but I think he must have been watching me, and he noticed all the time I was spending at the game room. I think this must have been when he decided to see if I could be open to having a relationship with him.
He started out innocently by making casual conversation whenever he saw me, and it seemed he was always there when I walked in and would make a point to say hello to me. John was soon offering me free games on the machines when I was hanging out in an attempt to build our friendship further. I enjoyed skipping classes to hang out at the game room and gradually our friendship grew to the point of where he started asking me to go out with him for breakfast or for lunch from time to time. At first, I rejected his offer, but after a while, I did go and when we eventually went out, our conversations were innocent on the surface, but as I would later find out, he was actually probing in an attempt to find out if there was a possibility that I would be willing to have sex with him.
Everything stayed innocent until one particular day, when we were out for breakfast. Our simple conversation turned to a conversation about sex and girls, and in conversation, 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 and when he found that I had never had sex, he mocked me. This made me self-conscious and he seemed to recognize it and said he was sorry. I nodded my head in approval, but this as possibly the opening he was looking for to change the conversation to one about homosexuals. John asked if I ever found other men attractive or if I had ever thought about having sex with another man. I immediately 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. He said, “Ok, ok,” and I still felt that the conversation was rather innocent, but that was all about to change. John then skillfully mentioned that he was bisexual.
He looked at me and asked if I know what that was. I had never heard the term before and when I told him no and shook my head, 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 in shook as he continued by explaining that he liked having sex with women but sometimes he enjoyed sleeping with men too. I could not believe what I just heard. He paused looking at me and then continued the conversation by asking what I thought about it. He had shown his cards now and when I did not respond right away, he tried to smooth things over by saying, I am so glad we are friends and that you can keep it a secret.” It put me at a slight ease and he must have felt it too because he proceeded by saying, “You have been such a good friend and I have wanted to tell you about my feeling.” I was speechless and John continued by trying to tell me how he found me attractive and that he has wanted to tell me that he fantasizes about sleeping with me. I suddenly felt very uneasy with the situation and I think he knew he had pushed the issue a little too much, but it was out there now. I did not know what to do and John was my only way back to school.
He put his hand out and 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 was making me nervous. When he realized I was not interested in his advances, he calmly said, “Come on,” and we quickly left the restaurant and headed back to the game room. In the car, we were not talking so he pressed the issue a little more and asked me to think about it. When I did not reply, he tried to explain that he would give me anything if I would sleep with him. He mentioned money, girls, and even a car or a motorcycle. I remained silent all the way back to the game room and when we got there, he put his hand on my leg and asked me to not say anything about what we had talked about. I nodded my head in agreement and finished by asking me to think about it and to let him know what I would like to do it with him. I again nodded my head and said, ”Ok.” At the time, it did not sit well with me about having sex with another man, but I needed to get out of the car and after we got out of the car and went our separate ways; the only thing I could think about was his offer.
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 and we can talk about it.” I must have thought there was a possibility to entice me but I did not want to go. He continued to force the issue so I decided to go with him. On our way to the restaurant, he put his hand on my leg and asked me what he could do for me. I quickly said, “Nothing,” but 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 paused and smiled. I knew I had given him the opening he was looking for but I just wanted him to leave me alone.
However, John was excited with the chance of getting me in bed and he quickly said, “Ok,” and asked what kind of car I would like to have. I told him I was not sure, but he wanted to keep our conversation open and he kept probing to know what kind of car. When I did not say anything, 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 of having sex with me and I think if I had given him an answer right then, he would have tried to take me to his place. He did not want to push too much now; because he felt I was open to thought of sleeping with him for a price if he allowed me some space. We ended up leaving 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 try to get me whatever kind I wanted. The conversation seemed to become innocent again and I was able to get away from him and his advances. It had worked but as we pulled into the parking lot, he reminded me to let him know what kind of car I would like. I told him I would and he immediately asked if I might be able to tell him tomorrow. I told him I would try and we got out of the car and separated as we went back into the game room.
I really did want a car and I thought about the different kinds of cars that I would like to have, not considering the implication of my answer. Thoughts were racing through my head but at the time I was only thinking about having a car, and not thinking about when or if I tell him what I would like that I would be opening myself up to having sex with him, and probably not just once, but many times.
I was confused about what to do but John had me thinking about what kind of car I would like to have and I really wanted one too. As I thought about all the different kinds of cars, one kept coming to mind and it was a 1956 Chevy, but now how do I approach John or should I even go through with it. I was troubled about what to do, what would happen if I actually went though with it? I was not sure, but the next day when I went over to the game room, there he was and he of course approached me and asked if I had made a decision. I was unsure as to how to answer, but I really wanted a car so 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 got in his car, and left. John put his hand on my leg and rubbing it, he told me he was glad to do this for me. I did not say anything and he asked me what I decided on. I hesitated and then told him that I would really like to have a ’56 Chevy. He looked at me and told me that he would start looking for one. He knew I was excited and I continued to tell 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 and again told me how glad he was that he could do this for me.
After only few days later, he came up to me and told me he had found the car and he explained that we should take a drive and talk about it. He was very good and in the car, he said he had already seen the car, and told me it was very nice. All it needed was to be painted, and that he could get it in a week or so. I was so excited to see it and drive it, and in all the excitement, I had forgotten the deal but he was about to remind me because he now had a question for me. He now said, “Well now that I have the car, when do you think you’d like to come over to my place.” I did not know what to say and I should have realized this was what he was looking for all the time. Pausing, 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. We will leave and you can still have the car. What do you think?” I did not say anything and he said, “Ok, well you think about it.” I nodded my head in agreement and when we returned to the game, he asked me to come by the next day to let him know what I want to do. I again nodded my head and said I would. I was eager to have a car and curious too, but hesitant about what would happen if I went through with it.
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The next day, as I went up to the game room, I was anxious to find out what would happen when I told John what I had decided. It kept running through my mind, but all I could think about was that car he promised. As I walked in the door to the game room, he came up to me and casually said, “Are you ready?” I simple nodded my head and replied, “Yes.” He asked, “Are you sure?” I hesitated and told him yes. John said, “Ok, let’s go then.” We quickly went out, got into his car, and headed off to his place. I started to get nervous as we drove; I was not sure if I really wanted to do it now, and I did not know how tell him that I had second thoughts. What was I going to do now? We continued to drive and now all I could think of was what I was going to be asked to do once we got to his place and really I had no idea what John was going to make me do. We were not saying much as we drove and I think to break the tension, he asked if wanted to get something to eat first. I said, “No,” and he nodded his he and told me everything would be all right. We soon pulled into an apartment complex not to far from the school and parked out front of an apartment. As we exited the car, I looked around to see if anyone was watching us and then we quickly went inside.
Inside, I noticed his apartment was nice. It was clean looking and as I continued to look around, John proceeded to close the blinds in the front room. He then motioned for me to follow him down a hallway toward the back. As we walked down the short hallway and went into the back bedroom, I noticed a bathroom in the hall and across from that; there was another bedroom with the door closed. John walked over to the window and closed the blinds, darkening the room a little, and I was glad he did, so no one could look in. It was a large bedroom with what appear to be a bathroom toward the back and a king sized bed against one wall. He sat on the edge of the bed and motioned for me to sit next to him by patting the bed. As I sat down next to him, he put his hand on my thigh and rubbing it, told me to relax, 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 too. As I sat there quietly for a second I thought that, I had better started undressing before he returns. I took of my shoes, my shirt, pants, and my socks, and piled them at the end of the bed. For some reason to keep my underwear on and to this day, I do not know why, but I suspect it was to hang on to something as long as possible. I had only just finished taking my clothes off when I heard the door to the bathroom open. I turned to see John turning off the light to the bathroom and walk toward me. He appeared to be wearing only a long sleeved, button down shirt and nothing else and as he got closer, I turned away. He sat next to me and putting his hand on my thigh, he noticed that I still had on my underwear. John asked, “What’s wrong?” because I was not completely naked, and I said, “What?” He quickly dismissed it and told me to lie down on the bed. As I did, he asked me to move over near the edge so I was facing the wall with the window. He came around the bed, knelt on the floor in front of me, and started to rub my body and legs. He gentle spread my legs, rubbing my cock through my underwear and propping my one leg up. I was trying to distance my thoughts from what was going on and I think because of this I was not hard. He started to take off my underwear and having trouble asked me to help him get them all the way off.
I quickly did and lay back down. John again propped my leg up, exposing my crotch. He tried to get my dick hard by stroking my cock and balls. He eventually did try sucking my dick but it was still rather limp because I was trying so hard to distance my thoughts. He stopped sucking and stroked it, asking me if it felt ok and then suggested I should try to help him get it hard. He started to suck my cock again and this time I thought about my cock being sucked so it would get hard for him, because I thought that maybe this was all I had to do for him is get hard and cum in his mouth, and he’d give me the car. It started to feel good in his mouth and as I thought about getting hard and cumming in his mouth, I got hard as he sucked and stroked my cock. He kept stroking my cock and from time to time, he rubbed my balls and even fingered my ass. I could feel myself about to cum in his mouth, but I was not very hard yet. I did not know if I should tell him I was going to cum or just do it. I tried to hold back until I was all the way hard, but I decided to cum. Cumming in his mouth prematurely I think it surprised him and I could feel my cock jerking in his mouth.
He stopped stroking and just took hold sucking my cock. 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, “That’s ok, I hope it felt good.” I simply nodded my head. As he got up off the floor, I though to myself, “It’s all over.” However, he told me to move over into the middle of the bed for him and reluctantly I did, lying on my stomach not knowing what he was going to do now. 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 started to rub my back and ass. John explained that I should try to relax now and I could feel him inching himself closer. He told me to put my head down on the pillow and he spread my legs a little. I could hear him flip open something and I hear him rubbing what sounded like KY on his cock.
John then told me again to relax and I could feel him start to rub my butthole with lube too. I pulled away slightly and he said, ”Just relax.” I tried to relax but when he put a finger in my ass, I tightened up. He said, “It’s ok,” as he continued fingering my ass. John remarked,” Oh, you’re nice and tight.” He then asked if I was ok and I said, “Aha.” He told me it might hurt a little at first but that I should try to relax. He moved closer, pushing my legs apart with his legs and I could now feel his hard cock against my butt hole. I could feel the head of his cock against my tiny hole and then I felt him trying to push his cock in me, to penetrate my tight ass. It was ok at first, but as he continued to push his cock in me, it really started to hurt and I quickly pulled away from him rising up on all fours. He tried to grab me and hold me but his cock slipped out of me. I told it hurt and he said, “Ok.” He then told me that I needed to relax more and that the pain would eventually stop, but that I needed to relax more and to try to keep his cock in me. He said to tell him when it stopped hurting, of course so he could try again. It only hurt for a little while, but I tried to delay him putting his cock back 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. “Ok, let’s try again,” he said, “but this time, really try to relax when I am in you.” I agreed and he put more KY on my ass, positioned himself between my legs, and tried pushing his hard cock in me again. The head of his cock went in me again, and again it hurt. I tried to wiggle free but he held me tight this time. I ask him to stop, which he did but he continued holding on to my hips to keep his cock in me. It did not really hurt as much as it ached. He told me to relax and that the hurting would go away. I tried to relax but it continued to ache. After a little while, John asked how I was doing and if I was doing ok. I replied that it was still hurting a little and I could feel him slowly trying to push his cock in me further. He was in me all the way now and it did still hurt a little bit, but John wanted to cum in me. I could now feel him start slowly moving his cock in and out of me, and when he did, it started to hurt again. I tried to tell him it was hurting again and he just told me to relax. I tried to rise up again and wiggle free but he again held me tight. “What’s wrong,” he said, “just try to relax,” as he gradually kept moving his cock in and out of me.
It stopped hurting and he kept moving his cock in and out faster and faster. It started to feel good having his cock in me and my cock was getting hard as his cock went in and of me, but suddenly I could tell he was frustrated. He stopped and explained that I need to help too; John told me that I needed to move back and forth with him. I should try to rock back and forth, as he pushes forward and pulls back. He tried again and he moved me back and forth with him. He said, “That’s it, keep going.” I did and it felt good this time and I really trying to get into it. He even reached around me and played with my hard cock as he continued fucking me. Now he quit playing with my cock and his motions became shorter, quicker strokes as he fucked me. It was hard for me to keep the same action going, but then all of a sudden, he pushed his cock way in me and pulled me close. I tried to pull away to keep the motion going, but he held me close and out of breath he said, No, don’t move!” I knew he must be cumming in me and could feel his hard cock jerking inside me. Out of breath, he hunched over me, slowly moving his cock in and out of me again and then he kissed me on the back.
John then said, “That felt so good,” and asked me if I liked it too. When I did not say anything, I could feel him slowly rise up, pulling his cock out of me. As he got up, he told me that I had better go into the bathroom and clean myself out. He walked toward the back bathroom and motioned for me to use the hall bathroom. Before I left, he told me to hurry back to the bedroom when I was finished. I got off the bed and rushed into the bathroom. I was not sure what he meant by cleaning myself out, but as I was peeing I could feel what I thought was KY seeping from my ass. I sat on the toilet and wiped my butt. When I looked at the paper there was KY on the paper and was it cum too? I was worried so I tried to push out whatever was inside me. I managed to push out some KY jelly and what looked like cum, but I was not sure. Afterwards, I realized that the KY seemed to float in the water and it was John’s cum that had sank to the bottom.
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 he motioned for me to get on the bed again. What was I going to do? He had me get on all fours again with my head down and again he climbed on the bed behind me. He told me to relax as he put KY on his cock and fingered my ass too. 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, 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 he could not do it if I was not helping. He kept trying and as he was trying to fuck me the second time, I thought that it actually felt good, but he had told me that we would only do it once.
Frustrated, he withdrew his cock from my ass and as he got off the bed, he told me to go ahead and get dressed. He hurriedly went into the bathroom to get dressed, leaving me there on the bed. I quickly rounded up my clothes and got dressed. 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 powerless. He was my ride back to the game room and I did not know what to say, so I said nothing. John said,”Well, you think about it.” We left the apartment and drove back to the game room. He suggested that he give me a ride home in which I accepted. When I got out of the car, John said, “See yea later.” I did not say anything as I closed the door and hurried inside. I could feel KY and cum oozing out of me and I felt a need to get everything out of me. I showered and tried again to push as much of his cum out of me as I could. I worried and did not return to the game room for several days.
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, he said, “Let’s go for a ride.” We got in his car, drove around and he asked how I was doing. When I did not say anything he proceed to explained that the deal was spend the night with him and he reminded me that it was for a car and that he expected that we would do it more than once. I did not know what to say but he continued by telling me that I did not do my part so the deal was off. I was in shock. What was I going to do now? He put his hand out toward me and said, “If you want to do it again with me, we could consider the deal back on.” 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 do it again, the car is yours.” I stayed away from the game room for a long time and when I did return, we were still on friendly terms, 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 where I lived and he suggest that I should come over sometime.
It was very close to summer break and I think he knew I would not be coming by the game room so he decided to move closer to me so he could keep the chance of sleeping with me open and possibly, I did too. When I did visit his new apartment, he had me come in and sit down. It felt uneasy when I entered his apartment, but I was still thinking he might give me the car.
The car never materialized and I never again had sex with him. I did try to contact him much later, but I was never able to find him. I have wanted to try it again, but these days, it could have deadly consequences.