Casual encounter

I did not take off my underwear for some reason, maybe as in an effort to keep some sense of pride though this whole thing or as long as possible. I only sat there for only a few seconds when I heard the door to the bathroom open. In looking back, I saw him coming out with what appeared to be only a long sleeved, button down shirt on. He turned off the bathroom light and as he started toward the bed, I looked to see if he was naked under the shirt, but I could not tell. As he got closer, I looked away and he sat next to me. He noticed that I had not taken off my underwear and asked, “What’s wrong?” I hesitantly said, “What?” He quickly dismissed it, rubbing my thigh said never mind. John then said, “Just relax, everything will be ok.” I nodded my head in approval and he told me to lie down on the bed. I laid on my back in the middle of the bed, not know what he wanted. John then motioned for me to move over to the edge of the bed, on my side so I was facing the wall with the window. He came around the bed and knelt on the floor in front of me. He started to rub my legs, my stomach, and then spreading my legs, he rubbing my cock through my underwear. I closed my eyes and tried to distance my thoughts from what was going on. He now wanted my underwear off and tried gently taking them off. He struggled and asked me to help him get them all the way off. I quickly sat up and pulled them off and John cast them off the end of the bed as I lay down again.

He repositioned me closer to the edge and returned to fondling my cock and ball. He wanted me hard and it did feel good as he rubbed my limp cock, trying to stroke it, but I was distancing my thoughts now and thus I was not getting hard. He now tried sucking my limp dick in an effort to get me hard, but still it was no use; I was not getting hard. He became frustrated and stopped sucking, but as he continued to fondle my cock, he asked me if it felt ok. I mumbled nodded my head, mumbling a yes, but he must have known that I had distancing myself, so he asked me to try. John was not going to stop until my dick was hard and I had cum, so I nodded my head, as he again started to suck my cock. I knew I had to cum so I thought about my cock in his mouth, thinking about how good it felt; wanting to cum in his mouth. I thought that if I could cum that maybe we would not do anything else, and then I would get the car just that easily. I wanted to cum in his mouth and it did feel good as he sucked and stroked my cock. Occasionally he would fondle my balls and suck them too; he even fingered my ass once, which was getting harder and harder. It was my first blowjob and it felt good, and I could feel myself about to cum in his mouth, but I was not fully hard yet. I wanted to be hard before I came, so I tried to hold back, but when I did this, I started to go limp again, and John felt it too. I had to make a decision; I had to do it now, hard or not, I needed to cum.

Soon I was close again. I held back somewhat letting it build and then I let it go, cumming in his mouth prematurely, which I think surprised John as my cock jerked a few times in his mouth, causing him to stop sucking and just pull on my cock as cum shot in his mouth. It was the first time anyone had sucked my cock and it felt good as he continued to try to suck me dry. However, almost immediately my cock went limp in his mouth. He tried to keep stroking my cock but soon disappointedly said,” Is that it?” I paused and said, “What?” but he quickly said, “It’s alright,” and asked if it felt good and I replied with a simple, “Yes.” John now got up off the floor, and directed me to move over into the middle of the bed. I scooted over and laid there on my stomach not knowing what he really wanted me to do but as he walked to the end of the bed behind me, he told me to get on all fours, like a dog. As I did, I could feel him climbing on the bed behind me now, telling me to move up toward the head of the bed a little. He gently rubbed on my ass as he inched closer, spreading my legs apart with his legs. John now had me pull a pillow out from under the covers so I could put my head down on it. He inched a little closer, spreading my legs a little more and spreading my ass cheeks and rubbing my ass. I could hear him opening something and then I could hear that he must be rubbing lubricant on his cock, but then John told me that I should really try to relax. I said ok, I could feel John smearing my hole with lube and slipping a finger in my ass, fingering my butt. It felt good as he gently fingered my ass with lube. ”Oh, yea,” John said, “you’re so nice,” and asked if I was ok. I nodded my head replying, “Yes.”

He again told me to relax and mentioned to me that it might hurt a little at first, but tried to reassure me that it would stop as long as I relax. I said ok and soon I could feel his hard cock against my butt hole as he tried to push it in me. It was ok at first, but then it really started to hurt as he tried to push his cock in me. I pulled away slightly and when I did, John asked me if I was doing ok, and before he could stop me, I quickly pulled away, causing him to pull out. He asked. “What’s wrong?” and I immediately told him it was hurting and as I tried to rise up on all fours, he told me to keep my head down. He was obviously annoyed and said, “Ok, well you need try to relax more and that the hurting would eventually stop, but that I needed to relax.” Frustrated he told me to tell him when the hurting had stopped. He of course wanted to try again and it did hurt for a little while, but I was not going to tell him, I did not want him to put his cock in me again so I put it off as long as possible in hopes of not doing it anymore. He asked a couple times if I was ready to try again and finally he decided that 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. It did hurt a little but was subsiding so I replied that I was ok. John slowly pushed his cock further and further in my ass, which hurt and I tried again to pull away but he held me tight. It was a dull aching and I tried to relax as much as I could as he started moving his hard cock in and out of my tight hole. It started to hurt more and when I told him it was hurting again, he stopped and simply told me to relax. I rose up and tried to wiggle free but he held me firmly and kept trying to moving his cock in and out of me. After a short time, he again asked if I was ok. He was not going to stop until he had cum so I tried to relax as he really tried to move his cock in and out fast and fast. My cock was getting hard as he moved in and out of me and it was kind of starting to feel good having is cock going in and out of me, but suddenly I could tell he was annoyed about something and he stopped. He explained that I need to help too and that I needed to move back and forth with him. He explained that I should try to push back and forward with him. 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, but unexpectedly his cock slip out.

He quickly put it back in me and as he continued, he explained not to go so fast. As we started up again, John reached around me this time playing with my now hard cock and remarked, “Where was this earlier?” Soon he stopped and seemed to concentrate his thrusts with short quick strokes as he continued to fuck me. It was hard to keep the same action going, but then all of a sudden, he pulled me close, and forced his cock deep in me, which hurt. I tried to pull away but he held me close and out of breath said, “No, don’t move!” I now knew he must be cumming in me and could feel his cock jerking inside me. Out of breath and thoroughly spent now, John hunched over me, which forced me to lay flat. He kissed me on the back and slowly moving his cock in and out of me, saying how good it felt and asked me if I was ok. When I did not say anything, he gradually pulled his cock out of me and as he rolled of the bed told me that I had better go into the bathroom and clean myself out. John walked toward the back bathroom and told me to use the hall bathroom and that I should 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 put his cock in my ass again, but as hard as I tried not to let him put his cock in me, it seemed that he was able to push his cock in my ass more easily than before. I did not want to do it anymore and I decided that this time I would not move 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 on, I thought you liked it.” “Let’s do it one more time.” It did feel good this time, but he had told me we would only do it once. He now tried forcibly moving me back and forth, fucking me, but it was not work.

Frustrated, he stopped, pulled his cock out, and rolled off the bed. He walked toward the bathroom and told me to go ahead and get dressed. As he closed the door to the bathroom, I quickly got dressed and sat on the bed waiting. When he came out, he sat by me again and told me, how nice and rubbing my thigh asked if I would like to try it again sometime. I again felt trapped; he was my ride back to the game room and I did not know what to say, and when I did not reply, he said, “Ok, let’s go.” We left the apartment and headed back to the game room John asked if I wanted him to drive me home, which I eagerly replied, “Yes.” As we drove, I could feel his cum and KY oozing out of me and as soon as he dropped me off, I went into the shower and tried again to push his cum out of me. I was scared about what I had done and wanted to distance myself from John.

However, a few days later, I returned to the game room to ask about the car that he had promised me. When I found him, he was friendly and asked how everything was going. I said everything is good, but what about the car. John was taken aback and he quickly suggested that we go for a ride. I said ok and we got in his car. As we drove around, he explained that our deal was that I would sleep with him, and because I did not do my part, he felt the deal was off. I was in shock; I was under the impression that I only had to do it once, but he continued by saying, “Well if you want to try it again, we could consider the deal back on, but only if we were to do it again.” I did not know what to say. I wanted the car, but did not feel I had to do it with him again; we did it once; that was the deal, I thought. I was upset and felt used.

We went back to the game room and before getting out of the car, he told me that he still had the car and if I was still interested in doing it again that he would give me the car.” I was irritated as I walked away and ended up staying away from the game room for a long time, but when I did go back, John carried himself confidently and brazenly acted as if nothing was wrong. We continued to be friendly to one another, because he knew I was probably distressed about the car and that there was a possibility that I would be willing to do it again to get the car. His new brash attitude made it hard to approach him to say I was willing to do it again and with his attitude, it had become obvious that John wanted me to be the one to initiate the need to continue the relationship, but how was I going to do it? I now felt unwanted and tried to forget about having the car, but in the back of my mind, I did want to continue our sexual relationship.