Casual encounter

It was now getting toward the end of the school year and one day when I happened to be up at the game room, John went out of his way to mention that he had recently moved closer to where I lived and that I should come over some time to visit. The apartment complex he had moved into was on the other side of the neighborhood, in a nice area. I was glad he told me and interested in visiting, but I was quite sure he did this in hopes of rekindling the situation over the summer by making it that much easier for me to come by his new place anytime I wanted. He then continued by asking me if I wanted to go see it. I was immediately suspicion, but it was the opening I was hoping for, so I nodded my head yes. We quickly got in the car and headed off. We did not talk a lot on our way, and to break the tension, he mentioned that I should try to come by sometime. I simply said, “UHHA,” but I was definitely interested. As we pulled in to the complex, John said, “Well here we are.” These were high-class apartments and as we parked, he said, “Come on,” and we went in. I was nervous as he closed the door and said, “Come on in.” When we walked inside it was dimly light with all the curtains closed.

It has been hard to remember this apartment but I do remember that it was quite spacious, with a large sections couch in the living room. I casually walked into the living room and as he closed the door behind us, a feeling of uneasiness came over me. As I moved further into the main room and I become nervous remembering what had happened before when we were alone, but then again why was I there? For some reason I was attracted to this kind of relationship. It was the first time I had had sex and I must have wanted to continue the relationship in hopes of making love with him again. As we moved around the front room, John asked if I wanted a tour as he moved toward the back of the apartment. He wanted to show me the bedroom and when I realized that was where we were headed, I fell back and John asked, “What’s wrong?” I turned away, wanting to stay in the front room. John came back to where I was saying, “It’s ok, why don’t we sit down,” as we both moved over to the sofa, I chose a spot of the couch near one end and John tried to sit next to me. I felt uncomfortable; but I knew I could easily leave and walk home at anytime.

We did not say anything for a while and as I looked around, he tried to break the tension first telling me how glad he was that we were still friends, and said that he was glad I wanted to come see his new apartment. I did not say anything, so he continued by saying that I could come by anytime. I was flattered by the attention and in the back of my mind, I wanted to do it with him again, but on the same note, I was hesitant. Our conversation paused again, and I remembered what had happened before and as thoughts of that day went through my mind, I had conflicting thoughts. What should I do? John now reached over and started to rub my thigh just as he did the last time, and he asked if I would like to see the rest of the apartment now. I did not know what to do. In a way, I wanted to stay but I was confused. John then stood up and casually started toward the back of the apartment where the bedroom was expecting me to follow him. I quickly stood up too, but instead of following, I said that I had to leave and started toward the door. John stopped and quickly came back to the front room, trying to persuade me to stay. I continued to make my way to the front door to leave, and just as I was about to go, John said, “Well, maybe you can come by another time.” In a way, I want to stay, knowing he wanted to get me in bed again, but I could not do it. As I left and walked home, I wondered if I would ever see him again, and if the car would ever materialize. I wanted the car, but how could I make it happen.

I did venture over to John’s apartment several times that summer, gradually became more and more comfortable when I visited, but it was never for very long and we never did it. I think he was waiting for me to make the first move now, when at the same time I was waiting for him to make the move. It could be the right situation was never there, or we were both apprehensive.

Summer was almost over and whenever I visited the game room with friends, John acted as if nothing ever happened, and I had a feeling that John had in someway moved on because as I looked on, he was leaving with other boys. I was somewhat jealous, because I knew what those boys were going to experience, but I was relieved in a way too. As I watched things unfold, I thought to myself that if he had moved on, then I should probably too. I had now became desperate in a way to make a conscious effort before it was to late, to try to tell John that I was ready to do it again, but as I prepared to return to school, I heard that the game room by the high school closed down right at the of summer. I could not believe it, how was I going to approach John now to tell him I wanted to do it. I went up to the strip mall where the game room was and it was gone, my plans were dashed to tell him how I felt. I knew where he lived, but then I remember that John owned another record store downtown. I talked a friend into going with me to see if we could find the record store, but really, I wanted to see if he was there and as soon as we walked in the door, I saw him behind the counter.

At first, he did not see me and I hurriedly walked with my friend toward the back before John had the opportunity to see me. I kept looking over to where John was as we casually looked around, being it was the first time we had ever been in this shop, but then John noticed us, and as I looked around, our eyes met. John nonchalantly walked toward us and confronted us asking if he could help us with anything, and saying, “Hey you guys used to come by the game room.” We both said, “Yea.” John looked at me, I wanted to tell him the truth but in front of my friend, I simply said we just wanted to stop in to check it out since the game room by the school had closed. John looked doubtful, but said, “If you need anything, let me know.” John smiled at me suspiciously, as our eyes met briefly and with that, I knew he knew why I was there. I became restless and suggested that we should probably go, but as we headed for the door to leave, John called to me to wait. My friend continued outside as he approached and told me that I should come by more often. I nodded my head, and he continued by telling me that he was still living in the same apartment, and that I should stop by sometime. I cautiously grinned and again nodded my head as I left.

A couple days later, I got a call and when I answered the phone, it was John on the other line. I was surprised as he casually asked if I knew who it was, quickly saying, “It’s John!” I paused and smiling said, “Hi!” We chatted briefly and then John asked why I had not come by his apartment. I was surprised at first and he asked if I wanted to come by sometime. I was nervous, but said, “Sure.” John paused on the other line, but quickly suggested, “How about I come by and pick you up?” I paused for a second and then replied, “Now?” and he gladly said, “Yea.” I was hesitant, but told him ok. No one was home so when he pulled up out front, I hurried out and got in the car with him. When I opened the door, John said hi, and I replied hi too as we drove off. A feeling of anxiety came over me and John told me that he was glad to see me, continuing by telling me that he was surprised that I came looking for him.

I did not know what to say so I just sat there. We soon pulled up to his apartment and went inside. John closed the door and asked me to go ahead and sit down as he closed the door and followed me to the couch. As we sat on the coach making idle conversation, John scooted closer putting his hand on my leg and reiterating how glad he was to see me again. He then casually asked, “Well, would you like to see the rest of the apartment,” as he stood up. I became very nervous, sitting there frozen, but then he said, “Come on.” I stood up and followed him to the bedroom and as we entered, John turned to me and asked, “Why did you come looking for me,” and when I did not say anything He spoke up saying, “I think I know why you’re here.” I was nervous; did he really know why I was there? John closed the door behind us, and turned the lights off, gradually moving us over to the bed, where he had me sit down. I tried not to look at him as he sat on the bed next to me, and began rubbing my back. John put his hand on my thigh, leaned into me saying, “Don’t worry,” and I closed my eyes as he kissed me on the cheek.

He then took hold of my chin, turning my head slightly, kissing me on the lips, which caused me to flinch slightly I kept my eyes closed, as he continued to kiss me and eventually sucked on my neck, while rubbing my chest. He again gently kissed me, pushing his tongue into my mouth, making me uneasy, but I wanted to keep going so I continued kissing with him. John then took my hand, placing it on his crotch as we kissed, having me gently squeeze his cock through his pants. I had never seen his cock, but it felt big and as he tried to take my shirt off, he stood in front of me and finished taking my shit off, throwing it to the side. John now leaned forward, gently pushing me to lying on the bed and saying, “lay down.” He undid my pants, pulling them and my underwear off, casting them to the side. As I laying there naked, John quickly took off his shirt and I looked up as he took off his pants and underwear, letting them fall to the floor.

His cock was big and I continued to watch as he slowly stroked his cock, seemingly wanting me to watch, and I so wanted to feel cock and maybe suck it, but as he quickly climbed on bed, and laid next to me, trying to kiss me, I tried not to show any emotions, turning my head, rejecting his advancement. He quickly positioned himself now, kneeling in front of me, spreading my legs, and rubbing the insides of my legs up toward my crotch. I relaxed as he continued touching me but then he reached forward, grabbed a pillow, telling me to lift up off the bed as he pushed it under me. My ass was raised now and John positioned himself in between my legs, lifting and spreading my legs further saying, “Oh yea.” As he started to fondle my cock, I thought to myself, “What was I going to do?” It felt so good and I knew what he wanted to do. I was in a vulnerable position with my ass exposed.

John pushed a finger against my tight hole, and as I laid back and relaxed, he pushed his finger in me. It felt good as he fingered me and then pushed his cock in my ass. It hurt and in this position, it was hard to pull back. John told me to relax as he pulled me closer, keeping his cock in me. It did hurt, but soon subsided as he started thrusting his cock in and out of me. I could not move very well, and I wanted to feel his cock jerking in me, and know he was cumming in me. I could hear his cock going in and out and soon John was out of breath and told me,”I’m going to cum.” I tried to relax anticipating the fell of his cock throbbing cum in me, and out of breathe he said, “Oh yea,” as he pushed his cock deep in me, holding me. It hurt, but I could feel his cock throbbing inside me as he came. John lay on top of me, kissing my chest and gradually pulling his cock out, rolling over, laying next to me.

As he pulled his cock out, I could feel cum oozed from my ass. I pulled the pillow out from under me and John pulled me close, looking me in the eyes, kissing me again, and letting him slip his tongue into my mouth. What had I done? I was in deep now, but as we laid there John started to fall asleep so I lay there quietly thinking, “Should I stay?” I decided I would leave after John fell asleep, but as I laid there, I too fell asleep. When I did wake and realized what had happened, I crept out of bed, and John rolled over, never waking up as I quickly dressed and left.

The next day, John called to ask me why I left. I did not have a reason, but I told him I just thought it was best. He asked if I had a good time and if I would like to come over again. I paused and when I did not reply John said anytime I want to come over. I told him ok and hung up the phone.

The car never materialized and I never again would have sex with him, but for a long time now, I have try to find someone, the right someone to share this experience of anal sex again and to explore my true feeling, but these days, casual sex could have deadly consequences. I have tried to meet other men and even transsexuals in hopes of hooking up to experience what it is like again having someone inside me and maybe even feel myself inside too, but when I start to consider what might happen and what could happen, I end up not follow through. I have continued to fantasize about my experience with John and about being with other men, thinking about John sucked my cock, and how it might feel to suck someone else's cock, and how good it felt when John's cock was in me and when I knew he had cum in me. I continue to fantasize about being with other men and transsexuals, however the feeling of a dildo in my ass, while masturbating gets old quick and I do so want to feel the real thing again.