Fateful Encounter

Written by , on 2018-01-14, genre first times


We have all had encounters that we remember and those we want to forget, but this particular one I had has stuck in my mind, even though I have for so long tried to put it out of my mind. I periodically I find myself remembering this eventful time in my life and I slip back to when it all happened. Maybe I wish it would somehow materialize again or that I could somehow go back and relive the experience. I have mixed feeling about it, but when it creeps back into my thoughts and I end up thinking about what actually took place; I eventually take myself back to that fateful time in my life and revisit the experience but then I wish again to forget it ever happen.

When this all happened, I had just turned fifteen-year-old, a delinquent; skipping class and always hanging out at the local game room by the high school with friends. A group of us always hung there during school, after school, and on weekends and at the time, I had always been able to get a girl and I had several girl friends over the years, but being a rather shy young man, I was still a virgin, but that was all about to change. I was spending a lot of time at the game room near school during the day and had started to become good friends with a man that ran the game room, For this story, I will refer to him as John. John was probably twice my age, had dark skin and dark hair, and it was not until a little later that I found out he was the owner.

As I said, everyone at the school liked hanging out up at the game room during the day and sometime, even into the evening, including me. I really did not take notice of John to much at first, but I think he must have been watching me and noticing how much time I was spending at the game room, and at some point, he must have decided to see if he could encourage me somehow to be in a relationship with him. At the time, I had no idea John was gay but it would soon be quite evident.

At first, it all started out fairly innocent. Our conversations were nothing more than asking him for change to play on the machines or the casual, “Hello” as I entered the game room. However, it soon progressed to him give me free games on the pinball machines when I was hanging out there and a few of the older guys that worked at the game room even started giving me pot and pills from time to time. My friendship with John grew and soon he was asking me from time to tine to go out for breakfast or lunch with him, which at first I was reluctant to do, but John eventually convinced me it would be ok. At this point, I was actually enjoying skipping classes to hang out at the game room, even though my grades were hurting, I didn’t care.
The proposal
John had started taking out for breakfast or lunch a lot and our conversations were innocent on the surface, but I am quite sure he was looking to build me up, and looking for an opening to get me to sleep with him. There was one particular day that stands out and when I think about what happened it was the turning point in our friendship to one of being more of a relationship. It happened when we were out for breakfast on day and our simple conversation turned to a conversation about sex and girls. John asked if I had a girl friend and telling him no, 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, but I said, “Yea,” I think somehow, he knew I hadn’t, because he quickly asked if I had ever had sex. I hadn’t had sex yet and when I told him no, he laughingly asked, “Do you liked boys?” I quickly told him no I just hadn’t had the chance yet. He quickly changed the subject by asking what hair color I liked, boobs, asses, etc., and laughing a little, our conversation seemingly returned to a more normal one, but John needed to find out if there was a chance to get me in bed. When the conversation paused, he said, “I know you said you only like girls, I get it, but do you ever look at a guy and think, hey he’s attractive.” I again told him, “No, I don’t think about whether a guy is attractive or not.” As our conversation lulled, he said, “Well, I think some girls attractive but some are not so attractive,” and when I agreed, he continued by saying, “I also think there are some guys that are attractive too.” I was stunned, but he continued by saying, “You know, some actors and actresses are kind of good-looking,” do you know what I mean. I apprehensive agreed, and John chuckled saying, “See, I knew you understood that there are nice looking people, no matter if they are male or female.” I felt things relax a little and as our conversation paused again, John asked if everything was ok. I nodded and said that everything was good. He quickly said tried to change the subject by saying that he really enjoyed my company and told me it was nice to be able to talk with me. I too told him I enjoyed it too, which I think gave him a feeling that he need to continue with his subtle approach. The conversation continued to be easy going and then he casually told he was sorry if he had embarrassed me. I nodded my head and told him it was ok. John smiled and as he said, “Good,” he quickly continued by saying that he understood that I only like girls, and as I looked up in agreement, he must have felt the time was right to push the issue a little more or maybe he needed to. Pausing for a moment he said, “Well, I need to tell you something and I know since you’re such a good friend I can trust you.” Looking across the table, I wondered, “What was he going to tell me I thought?” and listening nervously, he told me he was a bisexual. He paused to see my reaction and not getting one, he asked me if I know what that was. I had never heard that term before and saying, “No,” he leaning forward and seemed to relish the opportunity to explain that it meant that he was attracted to women but that he sometimes found men to be attractive too. I was stunned, what was he trying to tell me? He continued by telling me that he also liked sleeping with women and sometimes he like sleeping with men too. I was speechless but continued by asking me what I thought about it. I did not know what to do or say, and as the conversation paused for a second; I told him that I was not sure. John then smiled at me and said, “I really enjoy our time together, and because you have been such a good friend, I felt it was important to tell you.” I became nervous and wondered, ”What was he saying? He reached his hand across the table and continued by said that he liked being able to spend time with me and pausing said, “I find you attractive.” I was so nervous, and the conversation paused again for a second, but he continued by saying, “I felt I needed to tell you that because I have had thought about asking you if you’d like to come over to my apartment.” The situation was making me very uneasy and I think he knew it too. I did not know what to do; this man was my only way back to school and he must have known that the conversation troubled me, so he immediately tried to calm the situation by saying to me not to worry, that he was not going to do anything unless I felt the same way. I was relieved for a moment but still nervous and speechless, I did not know what to do or say. We soon left the restaurant and headed back to the game room and in the car, I think he knew I was upset, but having played his hand, he needed to press the issue a little more, but needed to try to calm things down a little. John said, “Thanks for listening, that was such a load off my mind to tell you.” He continued by saying, “You’ve been such a good friend, I want to get you something for being such a good friend.” I remained quiet but as we pulled into the parking lot, he asked me to think about it and asked me to please not tell anyone about what he had told me, because people wouldn’t understand. I told him I wouldn’t tell anyone and that I would think about it; how could I not think about it, even though at the time, it wasn’t sitting well with me about having sex with another man, but I nodded my head and said, “Yes.’

A few days later, I ventured back to the game room to hang out with friends and he asked if I had thought about it. I told him, “Yes that I had thought about it.” However, at the time I was still unsure. He said, “Come on let’s go get something to eat and we can talk about it.” On the way to the restaurant, I was quiet, because I was so nervous and noticing he asked what it was thinking, I said, “Nothing,” he said, “Come on, there must be something you really want,” and when I continued to not say anything, he became hard-pressed to get an answer. He said, “Come on, there must be something.” At the restaurant, we did not really talk about much, but I could sense 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. Pausing and looking up, I saw he was smiling. I now realized that I had given him the opening he was looking for and he quickly asked what kind of car I would like to have. I told him I was not sure, but he needed to keep the opening going and he kept probing to get me to tell him what kind of car I was interested in having. 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, the chance to possibly getting me to agree to have sex with him. 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 try to get it for me. As we pulled into the game room parking lot, he again told me to let him know what kind of car I want. At the time, I was only thinking about having a car and not thinking about that I was actually giving him the opportunity to have sex with me, and as it would turn out it would be more than just once. As we parked and started to get out of the car, he reminded me to let him know, and as I said I would, he immediately asked if I would be able to tell him tomorrow. I told him I would try.
For the next few days, all I thought about was what kind of car I would like to have and as I thought about all the different kinds of cars, one kept coming to mind: it was a 1956 Chevy, but now I worried about what would happen if I actually went though with it and told him? I was not sure, but later that week I went over to the game room and there he was. He eventually came up and casually asked how I was doing and then asked if I had made a decision. I was nervous and unsure as to how to answer, and when I didn’t reply right away he said, “Come on let’s go for a drive.” In the car, he asked again. I really wanted a car, but didn’t know what to do. Pausing for a moment, I told him what I wanted. He too paused and looking at me said, “Great,” obviously excited. I told him that I would really like to have a ’56 Chevy. He again said, “Great,” and told me that he would start looking for one, and in my excitement, 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 needed to keep this excitement going and smiling he told me would get right on it. As we returned to the game room, I was thrilled but the thrill turned to nervousness.
The Agreement
A few days past when I was at the game room, he came up to me and told me he had found the car and said 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, and knew it, but now he had a question for me. Pausing he continued the conversation by saying, “Well now that I have the car, are you ready to go with me.” I did not know what to say, but in the back of my mind, I knew there was going to be a catch to this whole thing. When I didn’t say anything he said, “I’ll tell you what, you come with me to my place tomorrow afternoon and give it a try and if you don’t like it, we can stop and I’ll still give you the car.” I felt a little better about it, and agreed to go with him. As we returned to the game room, he told me to come by tomorrow around noon. I was eager to have a car but worried about what was going to happen when I went with him to his place, but I also think deep down I was curious too. Later that same day when I was at home, I thought about everything I should do before tomorrow. I felt I needed to make sure I tried to clean myself out, not really know what was going to happen, but I think I had a good idea. I also realized I hadn’t cum for a few days and decided I should probably cum now so I can make it last longer tomorrow if he tries to make me cum.


The next day, I made sure to try to cleaning myself out a little, I took a long shower, even masturbated a little, to make I was able to get hard. Around noon, I headed up to the game room and was so 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?” Pausing, for a moment I simply replied, “Yes. “Are you sure,” ” he asked. When again I told him yes, he told me go ahead and go outside and told me he’d be right out. When he came out, he was smiling and we quickly we got in his car and headed off to his place.

The Act
As we drove, thought were racing through my mind. I knew we where going to his apartment, and 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, I’m ok,” and soon we pulled into an apartment complex not far from the school. As we parked out front, we quickly went inside. His apartment was nicely furnished bright and clean looking and as I looked around, he proceeded to close the blinds in the front room and then he quickly ushered me 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 part way. As we entered the back bedroom, he told me to go ahead and sit on the bed. As I did, he went over and closed the blinds, which immediately darkened the room; muting the little bit of light that did manage to come in. It was a king size bed and as I quickly scanned the room I could see it was a large bedroom with a bathroom toward the back. He now sat on the edge of the bed next to me and asked if I was ok. I nodded my head yes and as I did he put his hand on my thigh and rubbing it and telling me to relax and said not to worry, everything would be all right. I simply nodded and as I did, he stood up and he told me to go ahead and take off my clothes, and said that he would be right back. I watched as he walked toward the bathroom, which I presumed was where he was going to take off his clothes.
As he closed the door, I sat there quietly for a second and then figured I had better start getting 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 kept my underwear on, probably to give me some sense of security. I sat there for what seemed like a few minutes, and then I heard the door to the bathroom open. John stepped out, he turned off the light and walked toward me as I sat on the bed. He was wearing a long sleeved, button down shirt and as I watched him walking toward me I tried to see what he looked like naked and tried to see if I could see his cock, but it was too dark and his shirt conveniently covered him. I looked away got closer and sat next to me. He asked if I was ok and immediately noticing that I still had on my underwear asking, “What’s wrong?” I said, “What?” and as I did, he quickly dismissed it and told me to go ahead and lay down on the bed. Not actually knowing what he wanted, I turned and laid in the middle of the bed John then instructed me to move to the edge and asked me to lay on my side. I quickly shifted to my side and inched over until I was near the edge of the bed. This had me facing toward the wall that had the window with the closed blinds. As I lay on my side, he came around to that side of the bed, knelt on the floor in front of me, and started to rub my body and legs. He then propped my one leg up, which spread my legs, exposing my crotch. He then started rubbing my cock through my underwear and as he did, I tried to distance my thoughts from what was going on. After a little while, he tried to take off my underwear, but struggling he asked me to help him. I quickly sat up, took them off, casting them to the floor, over the end of the bed, and quickly returned to my position. He now tried anxiously to get my dick hard, rubbing my cock and fondling my balls, eventually taking my limp cock into his mouth sucking and stroking it, but with me trying so hard to distance my thoughts, my dick wouldn’t get hard, which soon caused him to stop. When he stopped, he asked, “Does it felt okay,” which brought me back into what was going on. I nodded in agreement and John then asked me to try to concentrate. I nodded again and as he started rubbing my cock, eventually sucking my cock again, I realized he wasn’t going to let me go until I had cum. I imagined cumming in his mouth and as I did, my cock started to get hard and noticing he stopped sucking my cock and as he continued rubbing my cock he said, “Yea, that’s it.” It did feel good in his mouth, and as he kept stroking and sucking my cock, I was really getting into it and I was starting to feel as though I was close to cum, but I wasn’t all the way hard. I tried to hold back, feeling I needed to wait until I was harder, but when I did, I started to lose my hard on. I had to concentrate again on cumming and soon I could feel it, I was close to cumming. I wasn’t hard but I needed to cum, so I concentrated and let it go, cumming in his mouth prematurely. I think it surprised him a little, maybe because I didn’t tell him I was going to cum, or maybe because I wasn’t hard but after the initial jerks and burst of cum in his mouth, he continued to suck, and my cum spilled into his mouth.
My cock quickly went limp in his mouth and in a disappointed voice he said,” Is that it,” and as I said, “What,” he quickly said, “I hope it felt good.” When I didn’t reply, he stood up and told me to move over into the middle of the bed. I quickly scooted over to the middle of the bed and not know what he wanted, I laid on my stomach. John had moved to the end of the bed and seeing me lying on my stomach said. “That’s it, now get on all fours, you know like a dog.” As I got on all fours, he told me to move up toward the head of the bed a little. I was nervous, and wondered, “What was going to happen?” I could feel him climb on the bed behind me, and as he inched closer, he spread my legs slightly. He told me to put my head down on the pillow, which caused my ass to spread a little and made it feel as though my ass was in the air. He gently rubbed my back and my ass, eventually spreading my ass cheeks, and upon seeing my tight virgin hole, said, “That’s nice.” There was a slight pause, but then I could hear him opening what I assumed was a tube of KY. I listened, and could hear what I thought was him sloppily rubbing his cock with KY and after a short pause he touched my tight little hole with his finger, which immediately caused me to flinch, and pulling away, fearing he was trying to push his cock in me. As I rose up slightly, John right away said, “Don’t worry, relax” and told me to put my head back down. He gently touched my hole, dabbing it lightly with lube, he then slowly pressed his finger against my hole, eventually pushing his finger into me. It caused me to tighten a little, which had John tell me, “Try to relax.” I nodded and as he continued to finger me he said,” Oh, you’re really tight,” and asked if I was doing ok as he moved his finger in and out. It did feel good, so I replied, “Yes,” but as he took his finger out of me, he moved closer and spread my legs a little further apart with his knees, telling me to relax. I nodded my head in agreement and I could feel him pushing the head of his cock against my hole. The pressure of him trying to push his cock in me didn’t hurt at first, but when the head of his cock finally penetrated me, it all of a sudden was so painful, I rose up on all fours and pulled away in pain. This I think surprised him because his cock to slip out of me and he asked me what was wrong. I quickly told him it hurt and pausing he replied, “Okay,” and said that I needed to try to relax more and told me to let him know when it stopped hurting. I nodded my head and put it back down on the pillow. I tried to delay him for as long as possible, hoping he would stop wanting to do it, but after asking me a couple times how I was doing, he had decided that he had waited long enough because he said, “Ok, let’s try it again.” He moved closer again, spread my leg and told me to relax, and said the pain would go away. I nodded my head and he again put lube on my hole and briefly pushed his finger in me again. He again tried to push the head of his cock in me again, I tried to relax, but immediately, it hurt and again I pulled away, causing his cock slipped out of me again. I told him it still hurt and could hear in his voice that he was irritated, because in a frustrated voice he said, “Okay, let me know when your okay.” However, this time he didn’t wait long before saying, Okay, let’s try it again,” and repeated that I had to relax this time and again explain that the pain would eventually go away, but I needed to relax. Like before, I knew he wasn’t going to stop until he got to fuck me, so this time I told myself to really try to relax and nodding my head, he immediately tried to again push his cock in me. It still hurt, I couldn’t do it, and trying to pull away, he held my hips not letting me pull away this time. I reached back, trying to push him away and saying it hurt. He held me, keeping his cock in me and quickly said, “I’ll stop but you need to relax.” It continued to hurt and after a little bit he asked if I was doing ok. When I didn’t reply he slowly continued to push his cock in me again. It continued to hurt the more he pushed and reaching back again, I asked him to stop. He stopped for a moment and taking hold my hand he continued to push his cock in me until he was pretty much all the way in. He asked how I was doing and even though it continued to hurt, I told him I was ok. He let go of my hand, and started moving his cock in and out of my tight hole. It started to hurt again, so I reached back pushing him away and telling him it was hurting. He stopped and when he told me to relax, I rose up and tried to wiggle free, but wasn’t going to let me loose. He held me tight and kept trying to moving his cock in and out of me as he held my hips. He continued by moving me back and forth, as held my hips, fucking. It eventually started to feel good and my cock got hard because of his cock moving in and out of me. However, he suddenly stopped, I could sense he was frustrated again and out of breathe explained, “I need you to help too,” I didn’t know what he meant until he explained that I needed to move back and forth with him. He again took hold of my hips and started moving me back forth showing me what he meant and said, “That’s it, keep going.” As I tried to keep the same motion, it started to feel good and I was really trying to get into it as he fucked me. Recognizing it I think, he reached around me, fondling my cock, which was now hard and said, “Oh yea, that’s it,” He only held my cock briefly and when he let go, he again took hold of my hips with both hands and started shorter quick strokes as he fucked me. It was hard to keep the same motion going, but then he suddenly said, “I’m gonna to cum.” He pulled me close, pushing his cock way inside me; it hurt and trying to pull away, he held me close and out of breath said, No, don’t move.” I knew he must be cumming in me and keeping my head down, I could feel his cock jerking inside me. He was out of breath now and as he hunched over me, and slowly moved his cock in and out of me before eventually pushing me flat on my stomach, He asked if I was ok, and then said, “That felt really good,” and asked if I liked it. When I did not say anything, he slowly pulled his cock out of me and as he rolled off the bed, he told me that I should go into the bathroom to clean myself out and directed me to use the hall bathroom. I quickly got off the bed and as I hurried into the bathroom, he told me to come back when I was finished. I was not sure what he meant by cleaning myself out, but as I stood there in the bathroom, I could feel something oozing out of my ass, so I sat on the toilet and wiping my butt, I tried to push out whatever was inside me. I managed to push out some of whatever was in me and as I looked in the toilet I could see that some had sank to the bottom and some floated, I figured it must have been his cum that sunk, but I was not sure. After a few minutes, I returned to the bedroom, and as I entered, he asked if I was ok as he moved closer to me. I nodding my head yes, and as he rubbed my back, he told me to get on the bed again. I thought to myself, “What was he going to do,” as I slowly got on the bed again. He had me move up and to put my head down on the pillow like last time and he immediately got on the bed behind me. He again spread my legs and fingered my ass with KY. What was I going to do, I didn’t want to do it again, but as he moved closer, spreading my legs further apart, he told me to relax. I started to wonder, “How could he be hard again so soon; he had just cum a few minutes ago.” I tried to tighten my ass in an attempt to stop him from putting his cock in me, but it was no use, his cock went in easily this time. I thought we were only going to do it once, I did not want to do it again, but his cock was in me now and grabbing me by my hips, he started moving his cock in and out of me. I decided I would not help by moving back and forth, as he fucked me and it didn’t take very long before he recognized I wasn’t helping. He was frustrated as he trued to forcefully move me back and forth so his cock was going in and out of me. He soon stopped and asked me what was wrong. I said, I thought we were only going to do it once. He then reached around taking hold of my cock, rubbing it and said, “I thought you liked it,” and taking hold of my hips said, “Come on, let’s do it one more time,” and he started to again fuck me by moving me back and forth. I didn’t want to do it anymore, but as he forced me to do it, it started to feel good, but suddenly he became so frustrated he stopped, quickly took his cock out of me and got off the bed. He told me to go ahead and get dressed and as I turned, I watched as he went into the bathroom. As he closed the door, I got off the bed and quickly got dressed and sat on the bed waiting. When he came out, he sat by me and pausing told me how nice it was with me and he asked if I would like to try it again some other time. I felt powerless, what could I do; I did not know what to say, and when I didn’t reply, we ended up leaving the apartment and in the car he told me he was giving me a ride home. We didn’t say much on the way and as I got out of the car I could feel the lube was leaking out of me and it was probably his cum too, I thought. When he dropped me off, he asked if I was ok and as I got out of the car, I told him I was ok. I quickly went inside and began to worry about what had happened. I hastily went into the bathroom and took a shower where I tried again to push his cum out of me.

I waited a few days m I was before returning to the game room. John approached me and asked how I was and after telling him I was ok I ask about the car he had promised me, he said. “Let’s go for a ride.” I was reluctant to go but wanted to find out about the car. As he pulled out of the parking lot and drove, he tried to explain that the deal was to sleep with him and told me that I didn’t do that. I was in shock, “What was I going to do?” He then told me if I would try doing it again, he would consider giving me the car, 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. He then asked, “What do you think.” I paused and then said, “I thought we were only going to do it once.” He replied, “I thought you liked it.” I didn’t know what to do, I wanted the car, but didn’t want to do it again. We went back to the game room and he said to let him know if you want to try it again, and made sure to say that he would give me the car if I would try it again. I was distraught and ended up stayed away from the game room for a long time. When I did return, we were friendly to each other, like nothing ever happened, but it seemed that he was still looking for an opening to continue the relationship, and maybe in a way I actually wanted to do it again too. After about a month, he mentioned to me that he was moving to an apartment closer to where my parents lived. I was surprised, and then he told me that I should come by some time. I knew where his new apartment was and I was immediately curious and wondered what he was up to, but deep down I knew the reason he moved closer to where I lived was that he was still looking for a way to get me alone so that he could have sex with me again. He then explained that he still had the car and again said I should come by. I later realized that he had gone to this extreme because it was the end of the school year and he knew I probably wouldn’t be visiting the game room over the summer, so he wanted to create a way to keep in contact with me and hopefully have me to visit him.

New Place
I wanted that car and was curious about if it was over at his new apartment, so I eventually I did venture over to visit and scope things out. As I approached the door to his apartment, I became nervous, but I knocked on the door. Stepping back I wondered, “What was I doing,” but I was there. When he answered the door and asked me to come in, a feeling of uneasiness came over me. As I proceeded inside, the front room was rather large, but he was keeping it somewhat dark; the curtains were closed and as I looked around, he quickly motioned for me to go into the living room area and said, “Go ahead and have a seat.” As I moved further into the living room, looking for a place to sit, eventually sitting on the couch. As I sat down, he had followed right behind me, and sat down on the couch too. He asking me how I was doing, and then said, “I’m glad you decided to come by.” As I looked at him and nodded, he smiled and reached over, touching me on my leg. I flinched, which caused him to take his hand away and pausing for a second, he said, “What’s wrong?” When I didn’t say anything, he quickly said, “You know, I still think about the time we spent together,” and pausing asked me, “Have you thought about it?” I nodded my head yes and as I did, he smiled and touching my thigh again said, “I’m, really glad you decided to come over.” I was nervous, and when he continued, he asked if I wanted to try it again. I quickly stood up and told him I had to go. He was visibly upset but let me leave, but as I left, he told me to come over again and said, “Maybe next time you can stay a little longer.” After that, I never spent time with him again, and the car never did materialized. However, when I returned to the game room several months later, I saw he was starting to take other boys to lunch and breakfast, probably doing the same thing to them. I did try to contact him much later, but never did find him. I have thought about trying to have sex with another guy, but these days, it could have deadly consequences.

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