We ended up at his apartment and when we eventually went into his bedroom, I knew what we were going to do. I wanted to feel him in me again, but I was nervous to do it.
I had never planned it, I actually stayed away from the game room for quite some time, but there was still a weird attraction I was feeling for John. Maybe it was because he was the first person to have sex with me or maybe it was all the attention he had given me, in either case, I still have a strange fascination to this day.
When I did start hanging out at the game room with friends again, I saw that John was now taking other boys out for lunch and breakfast. Seeing this made me a little jealous, to the point where I eventually wanted to approach him to see if he might still be interested in me. Over time, I got up the nerve and when I went up to him and we greeted each other, I hoped he’d suddenly ask me if I’d like to go out for lunch. Well it worked, and when he suggested going to get something to eat, I tried to act unconcerned but couldn’t help but smile. John smiled too, and then said, “Hang on.”
He was obviously excited, which made me a little nervous, but as I watched him, he went over and had a brief conversation with one of the game room attendants. After pointing over at me, he smiled, and as he came back over to where I was standing, he ushered us out the front door. As we headed off, we really didn’t say anything right away, but I could see out of the corner of my eye that he was curiously looking over at me. He eventually spoke up saying, “I’m glad you wanted to do this again.”
I wasn’t sure if he just meant going out for lunch or if he was suggesting that he thought I might want to have sex with him again. In either case I was nervous about it but deep down I did have an urge to be with him. When I didn’t reply, John reached over and touching my thigh asked, “Are you okay?”
Nodding as I continued to look down, John put his hand on my leg, which made me smile nervously as I now looked out the side window. At the restaurant, we spoke casually and when our conversation lulled, he leaned over the table slightly and asked, “Do you want to come over to my apartment?”
Looking up, I got really nervous, “What should I say,” I thought.
Seeing I was maybe a little apprehensive John said, “It’s okay, I understand if you don’t.”
In the back of my mind, I wanted to be with him, and not wanting to betray my feeling, I tried to find the right words. I found myself too nervous to say anything, and when John said, “How about we go over there and we can talk some more.”
I didn’t want to lose the chance, but I continued to be apprehensive about it and when John happened to say, “Let’s go over there, okay?”
Glancing over, I couldn’t help but smile, and as I nodded, I saw John was smiling too. He now reached across the table and as he took my hand, and we looked at each other, John immediately said, “Don’t worry, okay?”
John motioned for our waitress, and as he asked for the bill, I shyly looked down. After paying, John asked, “Are you ready?”
Hurrying us out of the restaurant and over to his car, we headed off. We again didn’t say anything and when John said, “We’ll be there in a little bit,” I shyly smiled and after a subtle nod, I looked out the side window.
As we pulled into his complex and parked out front, he again said, “Come on,” which made me instinctively, but nervously get out of the car. Following him to the door, I became extremely nervous to the point I almost decided to leave but as he opened the front door and held the door for me, I felt I had to go in.
Inside his apartment, we sat on his couch. It again was kind of dark in his apartment and as I sat there and looked around, I started to become a little anxious. Not looking at him directly, John scooted closer, and then asked, “Have you been with anyone since we did it?”
I had been with a girl, and we did make out, but we never had sex, and when I didn’t say anything John said, “It’s okay, I’m glad you’re here.”
It made me smile sheepishly but feeling a little ashamed, I continued to look down. I’m sure he could sense my apprehension and then as he touched my leg, John again asked, “Are you okay?”
Nervous, I didn’t say anything, I needed him to make the move and when he now placed his hand on my back and said, “Why don’t we go in the bedroom,” I instinctively looked up at him.
I was hesitant, but seeing John stand up, I found myself standing up too. John guided me toward his bedroom, and when I happened to slow down, John asked, “What’s wrong.”
Smiling as he looked at me, I blurted out, “I’m nervous.”
John again put his hand on my back and continued to guide me into his bedroom. As we went through the doorway John said, “Theres nothing to be scared about.“
The thought of having sex with him was suddenly racing through my head, “What am I doing,” I thought?
John continued to move me over to the bed and then as we faced each other, he unbuttoned his shirt, and then undid his pants. As he let them fall to the floor, I couldn’t help but look down. He was wearing tightie whitys and as I continued to watch, he adjusted his cock by gently pulling on it. Catching myself xstaring, I looked up. John was smiling and when he leaned into me, and tried to give me a kiss, I turned my head.
I was scared, and when he started feeling on my chest and eventually tried to take off my shirt, I couldn’t help but smile in anticipation. As I raised my arms, and let him take my shirt off, he casually threw it aside, smiling. John again felt on my chest, and then telling me, “Sit down,” he pushed me back onto the bed. Looking down as I sat on the bed, John immediately moved to sit next to me. He again put his hand on my back and as we faced each other, John again leaned over trying to kiss me. Again, not wanting to kiss him, I turned my head, which made John sternly say, “Relax.”
He was upset I didn’t want to kiss him, but for some reason he felt a need to get me to kiss. Continuing to look away, John grabbed my chin and then turning me to face him he said, Close your eyes.”
Apprehensively as I looked at him, I closed my eyes. I was nervous and when he did kiss me, I pulled away. I was shocked and when I opened my eyes, he could obviously tell I was scared. Smiling at me, he again said, “Close your eyes, it’s alright.”
As I again closed my eyes, John said, “Keep ‘em closed.”
Nodding, he leaned into me and as his lips pressed against mine, I winced. Kissing me again, he said, “See, that’s not so bad.”
Looking at him I smiled and said, “I’m just scared.”
John again said, Don’t worry,” and then told me, “Close your eyes.”
Smiling as I closed my eye, he again kissed me. It was nice, but suddenly when I felt him trying to push his tongue in my mouth, I pulled away. I think it frustrated him because he asked, “What’s wrong, don’t you like it?”
I was scared, it felt weird, and when he said, “Let’s try it one more time,” I knew he wasn’t about to give up trying.
John again said, “Close your eyes,” and as I did, he pressed his lips against mine and then leaning away slightly said, “See, that’s not so bad is it.”
Opening my eyes, I smiled, and then after giving a subtle little nod, John again tried to kiss me. Closing my eyes as we kissed, John whispered, “Open your mouth.”
I was scared, but did what he asked and as he pushed his tongue in my mouth, I closed my eyes even tighter. His tongue was all the way in my mouth, and as he tilted his head slightly, I found myself instinctively putting my tongue into his mouth too.
It was nice, but was still kind of weird and when we eventually stopped kissing, John said, “That wasn’t so bad, was it?”
When I didn’t say anything, John leaned up and then immediately started to undo my shorts. As he stood up and tugged at them, I smiled and leaning back a little, he pulled them over my feet. He was obviously excited and then holding them out, he smiled and then let them drop to the floor.
John again sat next to me and as he rubbed my thigh he said, “Why don’t you scoot back.”
Smiling, I slowly inched my way back and then as he leaned back on his one elbow, he said, “Why don’t you lay back.”
As I laid back, John started rubbing my cock through my underwear, and when he felt how hard I was, he asked, “Where was this the first time?”
Thinking he was joking, I smiled at him, and when I didn’t say anything, he immediately pulled the band down a little. John then reached into my underwear and pulling my cock out, he moved over to suck it. Laying back again and closing my eyes, I thought about cumming, but then he hastily sat up and started pulling my underwear down. Eventually taking them all the way off, he tossed them over the edge, and went back down taking my cock in his mouth again. I could tell he was struggling to pull down his underwear too, and when he sat back up, I leaned up to watch. As he got them down, I couldn’t help but watch as he pulled and stroked his dick.
He had a tan line and being he was dark complected, he had dark brown pubic hair and his cock was dark too. He was circumcised and even though he wasn’t fully hard, I could tell it was big. I liked seeing it and as I watched him rubbing it, it was such a turn on, I thought about wanting to touch it. Looking up at him briefly and seeing him smile, I think he could tell I was excited. Smiling too, I looked back down, and seeing the head of his cock mushroom out as he pulled the foreskin down, I had thoughts about suck it.
Looking back up at him, I wanted to feel him in me, but was nervous to tell him. John again leaned over to feel on my cock, and as we looked at each other he said, “I think you like this, huh.”
Smiling at each other, I’m sure he could tell I was open to having sex with him again. John now looked down, and as he pulled the skin back on my cock, exposing the head, he again suck it.
It felt good and as I again closed my eyes and lay back, John moved his hand down between my legs to fondle on my balls. Suddenly, I could feel John’s finger pressing against my butt hole. It was scared me but then realizing what he was doing, I spread my legs a little.
John was trying to spread my ass cheeks with his fingers, and when he pushed his finger into me, I squirmed a little. It felt good, it’s what I had wanted and when he looked up at me and asked, “Does that feel good,” I simply nodded.
Sucking my cock again as he slowly moved his finger in and out of my tight little hole, I couldn’t help but squirm a little more. I knew what he wanted, I wanted it to and when he looked up at me and said, “I wanta fuck you,” I instinctively leaned up on my elbows.
I didn’t say anything and then as John sat up, he coaxed me to sit up too by saying, “Come on.”
I was nervous, but immediately found myself doing what he said. I wanted to do it, but needed him to again initiate it and as I knelt in front of him, he put his hand on my back and said, “Why don’t you get on all fours.”
Smiling, I quickly moved to the middle of the bed and as I got in position, he moved behind me. John had now moved to kneel right between my legs, and after he spread them a little with his knees, he gently started rubbing my ass. As he moved my ass cheeks back and forth, he eventually spread them and remarked, “Oh yea.”
Anxiously wanting to feel him pushing into me, John leaned against me, and let his cock ride in my crack, I started to worry a little. John then started moving his cock up and down my crack, and when he said, “Just relax,” I suddenly started having second thoughts.
I wasn’t ready; I knew it was going to hurt, but I wanted to feel it, and then as John leaned over me, reaching up to the head of the bed, I watched as he grabbed a tube of KY out from what must have been a small pocket up under the headboard.
Seeing this as he leaned back up and knelt behind me, I felt a little relief knowing he was going to use lube again. Listening, I heard him squeeze a little out, and when I felt it dripping in the crack of my ass, a feeling of uneasiness came over me. John again placed his cock against my crack, and when he started sliding it up and down, I tried to relax.
It was such a turn on, I couldn’t help but press back into him in anticipation, and when he felt me doing this, he pulled away slightly. I again heard him squeezing a little more lube out, and when I heard him smearing some on his cock, I put my head down.
This exposed my puckered little hole and when I felt John press his finger into me, I tried to relax. It felt good and when john said, “You’re really tight,” I couldn’t help but smile to myself.
He was obviously turned on and I could tell he was jerking off as he finger fucked me, and when I said, “Oh yea,” and arched my back, John asked, “Do you like that?”
Nodding my head as he continued to finger my ass, I again subtly said , Aw,” but I was nervous about what was going to happen next. It felt good and when he stopped fingering me and moved up closer, I knew what he was going to do.
Knowing it was going to hurt, I tried to relax as much as I could in anticipation of him pushing into me. I was excited to feel him in me and when John said, “Try to relax, okay,” I knew what was coming
I could feel him trying to guide the head of his cock into me and then as I felt him going into me, I told him, “Go slow.”
It hurt, and when I raised up, and reached back pushing on him, I told him to stop. John immediately pulled out and sitting back he asked, “Are you okay?”
I nodded my head and smiling to myself, I again asked him to go slow. Putting my head down again, John immediately tried to push into me again. I tried to relax and yea it still hurt, but as I slowly rocked back and fort, letting him go in, it didn’t hurt quite so bad.
He was in me now and when he again asked if I was okay, I nodded saying, “Yea.”
I wanted him to cum in me, I wanted to feel it and as he fucked me, I knew what to do. John now started fucking me, obviously wanting to cum, I know I wanted him to, but then he suddenly stopped. “What was wrong,” I thought, and as he pulled out he said, “Turn over.”
I was confused about what he wanted, but when he pushed me over until I was laying on my back, I couldn’t help but smile. John now grabbed a pillow from under the covers and then telling me to lift my butt up, he tucked it under my ass. I tried to get comfortable, and when he lifted my legs up in the air, deliberately exposing my tight little hole, I smiled in excitement.
I knew what he wanted to do and as I tried to keep my legs up for him, he scooted closer. John now intently tried to put his cock in me but suddenly as he leaned forward it easily slipped in. It hurt, and not expecting it, I pulled away. John could see it hurt, and as he pulled out a little he said, “Sorry.”
It was actually okay now and when I said, “It’s okay,” he smiled.
As I watched John slowly moving his cock in and out of me, I again thought about him cumming in me. John eventually looked up, and when saw I was watching, he smiled and then leaning forward, he kissed me on the cheek. As he looked at me he asked, “Does that feel okay?
Nodding, I smiled and then as I laid back, John pushed into me a little more. It hurt a little, and when I looked up, and saw he was smiling, I smiled too. John now leaned up and said, “Close your eyes.”
Smiling, I did what he said and as we kissed, he push his tongue in my mouth. Continuing to kiss, I tried to keep my legs up, and when John suddenly started fucking me harder, bucking his hips into me faster and faster, it started to hurt.
Trying to block it out, I grabbed a handful of sheets, clinching them. I hoped he’d cum soon, and when John suddenly stopped kissing me and wrapped his hands under my shoulders, I simply said, “Cum.”
I knew he was probably close, because he was breathing hard and when I tried to match his thrusts, wanting him to cum, he said, “Stop!”
He continued to fuck me and then suddenly in an out of breath voice said, I’m going to cum.”
Pushing deep into me he stopped for a moment, and as he slowly moved his cock in and out, I could feel his cock faintly throb as cum pumped inside me. His cock bucked a few times, and feeling he had cum a lot, I smiled to myself. John then leaned up and as he kissed me, I smiled and wrapped my arms around his neck.
John now leaned away and as he pulled out, I leaned up to watch. He was trying to squeeze the last little bit out, and seeing he was still relatively hard, it made me smile. Continuing to watch as John now leaned forward, trying to guide his cock back in me, I tried to relax. John’s cock slipped in easily and feeling cum seeping out I lay back again, as he gradually started pumping me again.
He was obviously going limp, and then as he pulled away again, he let it slip out. I could feel cum was now oozing out of me, and when John looked down and saw his cum, he smile. Looking back up at me he asked, “Are you okay.”
Smiling, I nodded and as John laid on top of me again, he gave me a kiss. It was nice, it was what I had wanted and then as he rolled off me and we lay together holding each other, he asked, “Do you wanta cum?”
“Of course I want to,” I thought and then as John started giving me a handjob, I laid back. It felt good, I wanted to cum and when he started sucking me, I thought about fuck him. I wanted to ask, I wanted to try it and when John happened to stop, and ask, “Does that feel good,” I smiled sheepishly.
Continuing to jerk me off, he suddenly asked, “Do you want to try fucking me?”
I was shocked, “How did he know,” I thought and when I didn’t say anything, I think he knew I wanted to try it.
Saying, “Come on,” as he got up on his knees, I quickly shifted until I was behind him.
John smeared a little K Y on his puckered little hole, even fingering it a little. At first, it was kind of a turn on to see his tight little hole and think about being in him, but as I jerked off, and John reached back, pulling me closer, I became nervous about fucking him. I had never done it before, not with a girl and definitely not with a guy. I wanted to try but as I got in position and tried to push my cock in his ass, I started to go limp. I couldn’t believe it; I wanted to do it, and as I desperately tried to get hard, I suddenly realized it wasn’t going to happen.
Dejected, I rolled over and as I laid on my back, and covered my face John asked, “What’s wrong?”
I was embarrassed, and as I covered my face and lay there, it had to be obvious, especially seeing my cock was limp. As John leaned toward me, he said, “It’s okay.”
I knew John was looking at me, and then as he reached over and tried to get me hard again, I tried to smile. John then asked, “Do you want me to help you?”
Bashfully, I smiled and as he started stroked my cocky I closed my eyes. I tried to concentrate and as I started to get hard, John leaned over and taking my cock in his mouth, he started sucking it. I wanted to cum, I wanted to him to know I liked being with him. As I started to get hard, John looked up at me and asked, “Does that feel good?”
I was trying to concentrate on cumming, and as I got close, I told him, “I’m going to cum. John immediately started sucking me and even though I wasn’t hard, I tried to think about cumming in his mouth.
John now said, “Cum for me,” and as I started bucked my hips, it didn’t take long before cum was shooting out on my stomach.
Continuing to stroke me as I went limp and cum dribbling out, I reached down and told him to stop. I was done and as he let go and we lay there, John remarked, “That was a lot.”
Smiling at him, he looked down as he ran fingers through the cum on my stomach. I was glad to have cum, I felt I needed to but I still felt a little ashamed that I wasn’t able to fuck him.
As we laid together, I felt I needed to leave, and when I told him, John tried to convince me to stay. “What could I do,” I thought, and so I decided to stay.
Continuing to lay together and hold each other, John eventually rolled to his other side and we both fell a sleep. In the morning when I woke up, I laid there for a moment, thinking about what had happened, I told myself, “I couldn’t stay, I had to leave,” and after getting up and using the bathroom, I quickly got started getting dressed. John was sitting up now and as I started to leave, John threw on a robe, but before I left, John said, Thanks.”
Smiling as I went out the door. I still felt a little embarrassed, embarrassed that I couldn’t do it, and as i headed home I thought to myself, “Maybe I’m not a top, maybe I’m only a bottom,” but then said to myself, “What am I saying?”
We still see each other and talk in passing, but we do tend to keep our distance. I still wanted to see him again and I hoped I get another chance, but as of now, the opportunity hasn’t presented itself. I still have conflicting thoughts for time to time, and I don’t think he really knows how much I want to be with him, but I’m sure he’d like to do it again.