Another great story of me when I was younger. Read the whole story!
I hope you guys enjoyed my Daniel series. There will be more of those to come but I wanted to write this story as it provides some background of when I was younger. Just a warning this story is LONG so take your time and try to read the whole thing as each part compliments the next.
I have always known I was different from everyone else. I never knew how but I hadn’t quite figured it out. At barely 16, I definitely looked young for my age. I wasn’t a late bloomer or anything like that but people regularly would think I was 14 or some 13 years old. I have blond hair and blue eyes standing at 5’6” and 110 pounds I was still awaiting my growth spurt. Up until I babysat Chris that’s what I thought was different about me.
Chris was a neighborhood kid that lived a few houses down from me and he is 9 almost 10 years old. His parents and my parents were friends so we knew each other pretty well. He moved into the neighborhood when he was about 7 and was super shy. He isn’t so much shy with me anymore but we’ve had a lot of people move in and out of the neighborhood because of the economy. He was cute, normal size for his age and wore glasses. He had blonde hair like me and brown eyes. Chris was about 4 ft 6 in and probably weighed about 80 pounds, pretty average for a boy his age. Some people thought he and I were brothers when we were together.
I’ve babysat Chris a few times. Mostly date nights; Fridays and Saturdays sometimes during the day too. One summer afternoon my parents got home and they wanted to talk to me. I was worried because I had no idea what it was about and they weren’t getting home until evening. After going all day worrying about what I might have done wrong my Mom and Dad got home. We were sitting down eating when my Mom had finally said, “What I wanted to tell you is that we are going out of town for a week.” I sighed in silence. “Is that all?” I replied. “Yes and no.” Dad replied. I gave them a funny look. “We won a trip on a cruise with the Delaney’s (Chris’s family).” In that 2 seconds I pieced together that since I’m an only child and Chris is an only child, with both my parents and his parents going on a cruise together I would have to babysit Chris. “Since the Delaney’s are going with us we had talked about you watching Chris for the time we were all gone.” My Mom said. “Now we wouldn’t ask you if you weren’t capable. Your mother and I have talked with the Delaney’s and they are fine with it too.” Dad said. “As long as you are fine with it, they will be willing to pay you too.” Mom replied. “Yeah, sure I don’t see why not.” I said pretty excitedly.
It came the day for both my parents and Chris’s parents to leave. It was decided that Chris would stay at my house since that was where all the food was. Chris was going to spend 5 days with me. We had simple rules nothing major as my parents knew I was really responsible.
After our parents left Chris and I were just hanging out watching TV. It was about 8:30 at night when Chris got up and said he was going to take a shower before going to bed. “OK, you know where it’s at right?” I said. “Yep” he said. He was in the shower for about 10 minutes and came out with a towel wrapped around him. He left his bag in the living room where his clothes were at. He grabbed his underwear from his bag and sat down on his couch. I wasn’t paying too much attention to him as I was watching a MX race on TV. Chris sat down on the couch with the towel next to me and put on his underwear under the towel. He sat there for about a couple minutes then “Do you care if you see me in my underwear?” Chris asked. I looked at him, smiled and said no. He took the towel off and put it on the door. He was wearing blue and green Gap briefs. I looked at him for a brief second and he sat back down on the couch. I couldn’t help but to look at his legs. He had both of his legs and feet on the couch as if he was keeping his crotch from view.
I didn’t look too much longer and continued watching TV. After a while it was close to 10:00 and we were both tired. I took Chris to the guest room and then I went to my room. I was lying in bed in just my boxers reading a book. Then at 10:30 I heard Chris say my name quietly as if he wasn’t sure if I was awake or asleep with only my dim bed light on. “Yeah” I replied. He came through the door slowly. “Can I sleep with you?” He stopped and asked quietly. “Sure” I responded. He continued to walk slowly to me as if there was someone asleep in the room. I lifted up the covers so he could climb in. I almost thought about putting pajamas on because it was kind of weird. But I decided not to because I didn’t want to make Chris feel uncomfortable. He was already fine with getting in bed with me as it was. The instant he laid in the bed he snuggled right up to me and put his arms around my chest and his leg over my legs. For some reason his body felt so good against mine. The warmth and the smoothness were unspeakable. I tried to not think too much about it. “Are you scared or something?” I asked. “No, well maybe, my parents haven’t been gone this long before.” Chris said in his whisper voice. “Well mine too.” I replied. “But I’m glad you are watching me.” He looked up and smiled at me. I smiled back “I’m glad I’m watching you too.” He put his head down on my shoulder and I turned off the light. “Goodnight” Chris whispered. “Goodnight” I replied.
I woke up at about 6:30am the next day and Chris’s head was on my chest and his hand was on my stomach almost at my waist line. He was still asleep. I started stroking his hair down to his back. I noticed his briefs were down a little bit on his back and I could see down his butt. After a couple of minutes he rolled over in his sleep and the back of his head was on my chest. I looked down his chest and at his crotch and I could see he had a boner. I thought to myself if me stroking his hair and back gave him one or not. It looked average size I guess and his underwear was dragging in the front to see his pelvic bone just above his dick. I found myself that I was starting to get a boner too. I thought about reaching down to see his dick and what it looked like but I got up instead to take a shower. I covered him up so that way he wasn’t laying there almost naked. I got out of the shower and he was up. Chris got a shirt on and we went downstairs to eat cereal. When we were eating Chris said, “Sorry if I move around a lot” “It’s fine I didn’t notice, I’m a hard sleeper.” I responded while eating. “Yeah me too” Chris replied. “Your head was on my chest when I woke up” I said laughing. “Yeah, I do that” He laughed in response. We finished breakfast and had a full day of activities and playing around the neighborhood.
It was a practically a normal day. We rode bikes, hung out, played video games, ate lunch then dinner. Our parents could call the first day because of where they were at on the cruise they told me before they left. We were hanging out again at night watching TV. Chris was sitting with me on the couch with his head on my shoulder and my arm was on the back of the couch. Chris then sat up and took his shirt off then stood up and unbuttoned his pants. He looked at me and smiled “I don’t like to wear a lot of clothes at home” he said. “Oh, I don’t care” I replied. He pushed his pants down and sat with me again in his underwear. I put my arm around him and he snuggled closer.
It was getting close to 10:00 “Ready for bed?” I asked Chris. “Yeah, sure” He replied. “Can I sleep with you again?” Chris asked. “Sure” I responded. We both got up and headed for my room. “No shower tonight?” I asked as I was taking off my shirt. “Nah, I don’t really feel like it unless I have to.” “No it’s fine, that’s why our parents are on vacation.” I said. I took off my pants and I laid down on he climbed in bed with me. He did the same thing and cuddled up the same night as before. I could feel his dick against my side and his skin felt so good against mine. “I like to cuddle” Chris said. “I’ve noticed” I said chuckling trying not to think about getting a boner. I turned off the light and he said his goodnight whisper and I replied. After about 10 minutes I was still awake but my eyes were closed. I was having a hard time falling asleep because I was thinking about the morning.
After 5 more minutes I was still awake and I felt Chris shift. I kept my eyes closed because I wanted him to think I was still asleep so he would go to sleep. Then I heard him say in a low whisper “Tyler”. I didn’t respond. “Tyler” Chris whispered again. His hand was still on my chest and he slowly started moving it. I pretended I was asleep thinking he was just seeing if I was awake. He was moving his hand on my chest and stomach and it actually felt really good. I could tell his breathing sped up and I could feel his breath on my chest downward. I could tell Chris’s head was faced down and not on my face. He kept rubbing but moved down toward my stomach. I think at that point I knew what he was doing. I continued to pretend I was asleep.
Then I felt his hand make his way on my waistline of my boxers, then on my pubic hair and then my dick. I was still soft and I kept myself from flinching or any body movement. He started to rub my dick on top of my boxers and I started to get a hard on. At the same time I could feel his hard dick on my side too. He was slowly shifting his hips and humping me as he rubbed my dick. It felt so good; I didn’t want him to stop. I wondered if he had done this the night before. I had a full hard on and I could tell he did too. He stopped rubbing my dick and I could feel him shift a little more. His hand slowly grabbed my dick and he slowly pumped it over my boxers. I was in heaven and this was the first time something like this had happen. After a little bit he stopped and I felt his hand making its way under my waistband. He was going for it. I felt his hand touch my dick. I could tell he was trying to figure it out but he got a hold of it. His hand on my dick felt so good. I felt his other hand come and he slowly grabbed the waist band and pulled it down so he could see it. He paused for a second, I’m assuming to look at my 16 year old dick. It probably looked big to him, I was probably about 5 ½ inches and I am circumcised. I had pubic hair but not a lot at the time, hardly any on my balls and it was a light color like my hair.
At that time Chris sat up. One of his legs was still over mine and his dick was now on my thigh still hard. He kept on hand on my waistband to keep it down and the other on my cock. I kept my eyes closed the entire time and I was obviously selling him on that I was dead asleep. Then he did something I wasn’t expecting at all, he licked the head of my cock. I flinched a little as I wasn’t expecting that at all. I knew he was experimenting but I think this was different. After a couple seconds he licked it again and again but they were small licks. Then he put his mouth on the head of my dick and I could feel his tongue working around. It felt so good. He was trying to suck my dick but I could tell he was learning how to do it. After a couple of minutes he stopped and put my waistband back up. I have to say I was disappointed he stopped but I could tell he was slowly moving. I was trying to figure out what he was doing until I felt him on top of me. He straddled my legs and felt both of his hands on my waistband and he slowly pulled my boxers up and over my hard on. I could tell he was being really careful. I thought to myself if I was sleeping would I wake up?
Once he got my boxers just below my dick and balls he laid down on top of me. Then I noticed he didn’t have his underwear on. He was completely naked and his hard dick was on my hard dick. His chest felt so good on mine and his arms were above my shoulders. His head was on my upper chest close to my collar bone and he was looking to the side while he slowly pumped himself on me. I opened one eye and I could his ass cheeks. He stopped and I closed my eyes quickly. He lifted his head up from what I could tell and he brought his face close to mine. He could feel his breathing on my face and a couple seconds later he kissed me on the lips. He held it for a few seconds then broke it.
Chris slowly got up being careful to not wake me up as if I was asleep. He grabbed my waistband and lifted it back over my dick. He shifted a little with what I assumed him putting his underwear back on. Then within a few minutes he was at my side snuggling again. Both our dicks were still hard. I felt his dick getting soft on my side but I was so horny, I wanted to jack off so bad. But I was able to subside that. I think I finally fell asleep around 11 after all the activities. I honestly couldn’t believe what just happened and I wondered if he had done that the night before. I debated in my head if I was going to confront him or just play it cool.
I woke up the next morning and Chris was already up playing Xbox downstairs in his underwear. “You’re up” I managed to get out. “Yeah” he replied fixated on the game. I stood there and looked at him while he was playing the game. I decided to play it cool and see what he does. “Want some breakfast?” I asked. “Sure!” He paused the game and got up. He came over to the table and sat down. “I hope I didn’t move around a lot.” Chris managed to get out. “I didn’t notice” I replied calmly. “I guess I tend to do that” he said eating his breakfast.
I played it cool all day with him. I did notice that he was looking at me more, or I just didn’t notice that before. Through out the day I wondered if he was gay or if he had done that before and if he would do it again. I made it through the day and night. We talked to our parents and said we were having fun and everything was OK.
After dinner we watched more TV and played some Xbox. He then got up “I’m going to take a shower since I didn’t take one yesterday.” “OK, sounds good.” Christ started getting undressed and got down to his underwear and took those off too in the living room. I took a few looks and saw his dick as he was grabbing a new pair of underwear. It looked small but it wasn’t hard and I could tell he wasn’t circumcised. “OK, I’m getting in” Chris said with giving me a full front view of him. “OK” I said. I couldn’t help to think that was an invitation.
I took a shower as well while he was. I almost went in there with him, in fact, I stood at the door ready to open it and go in but I decided not to. I took a quick shower and got into some boxer briefs. When I got back to the living room Chris was sitting on the couch in some white Gap briefs. I was beginning to think that this kid wasn’t only cute but hot too. I sat on the couch and Chris instantly came up to me and snuggled.
We got into bed that night and I told him I was tired. He said he was too. After about 15 minutes of being in bed I slowed my breathing and tried to pretend I was asleep. Chris was laying with me the same as usual; his chest against my side, leg laid over me and hand on my chest. I was wondering when he was going to start then I felt his hand move down my chest. This time he didn’t waste anytime jacking me off. I got a boner pretty fast and he was already working it. He got up and I could hear he was taking his underwear off. I could then feel both his hands in my waistband. He pulled my underwear over my dick and then I could feel him trying to pull them down. He got them down to my upper thighs and then took a hold of my dick and started sucking it again. He had one hand on the base of my dick and the other on my stomach. I could tell he was experimenting with it as he was trying to take my dick deeper but he couldn’t. After a few more minutes he stopped. I could feel him moving up until his hard dick was against mine. He then sat up so my dick was straddled between his legs. He started moving back and forth letting my dick rub between his ass and balls.
I was wondering if he thought I would ever wake up and if he was worried about that or he really did think I was a heavy sleeper. He laid back down on me and had his head to his side on my chest. Chris put his legs on the outside of mine so my legs were in between him. He had one arm back and it looked like he was fingering his ass. He took his other hand back and was using both hands to finger his ass. He did that for about 45 seconds until he sat back up. I felt him spit on the head of my dick then I felt it on his asshole. He had a hold of my dick while he was straddling me. I couldn’t believe what he was doing. He was slowly lowering himself down on my dick then I felt my head pop into his ass. Chris let out a very quiet moan. He started to go up and down until my dick was about half way in. It felt so good and I wanted to keep pretending I was asleep. Chris started jacking himself off from what I could tell. Then I thought to myself could he orgasm yet?
After about 5 more minutes I was staring to worry because I knew I was close to cumming. I decided to shift in my sleep and it made him stop and pull out. I think he got scared after that because he quickly got my underwear back up and he put his underwear back on. I then decided I would somehow tell him in the morning I knew what he was doing and that I wanted to continue.
In the morning I was up at 8:00 and downstairs. At about 8:15 Chris came down. “Hey” he said. “What’s up” I replied playing it cool. “Nothing” Chris said. He was still in just his underwear and walked over in the kitchen. “Sorry if I moved around a lot” he said grabbing a bowl. “I don’t care” I replied. I got up and walked over to him with his back to me and I was just fixated on his ass that I just fucked that night. I got behind him and put my arms around his stomach. “It’s totally fine” I whispered in his ear. My dick was already hard and I pushed my dick against his ass and I moved my hand down to his dick. “I would love to finish what you started last night” I whispered again. I kept one had on his dick which was getting hard and the other on his chest. “You were awake?” He asked. “Yes and last night too.” I started kissing his neck and rubbing his hard dick on top of his underwear. “I was afraid you wouldn’t want to” Chris said. “I want to” I replied.
As I was humping him and I reached into his underwear and started to jack him off. I looked over his should to see his dick. It was actually a good size erect and I kept jacking him off. I had never seen an uncircumcised dick before that. Chris pulled his underwear down to his ankles and I followed by doing the same thing. I put my dick between his ass cheeks and humped him some more. “I liked how you kissed me the other night.” I said into his ear. I turned his head up to me and started kissing him. Chris kissed back as best as he could and we were both learning. He turned around and we kept kissing I grabbed his butt with one hand and his thigh and lifted it with my other hand.
Chris broke our kiss, kneeled down and started sucking my dick. I put my hands on his head while he sucked. “You’re getting better” I said. He stopped sucking for a second “I’ve been practicing” he said chuckling. I let out a chuckle too. “Stand up” I said. Chris stood up. “My turn” I said. I knelt down and started sucking his dick. I was able to take it all the way in as it wasn’t big. Chris put his hands on my head and I put his hands on his ass. I could tell he liked it because he was thrusting his hips as I was sucking. After a couple of minutes I stopped “Let’s go to my room” I said. “OK” he replied. We got to my room and he laid on my bed and started rubbing his dick. “Now what” Chris asked. “We are going to finish what you started last night.” I walked over to the bed and I realized something. “Hang on I’m going to get something.” I went to the bathroom and got some petroleum jelly. I got some and sat on the bed. Chris instinctively put his legs up. I got some on my fingers and started rubbing it on Chris’ asshole. I then took some and rubbed some on my dick. “This will probably be easier than last night.” I laughed. “Probably, I never thought of that” Chris said. I lined up my dick with his hole and started to push in. My head popped in and he let out a moan. He had his head back and mouth open. I started pushing in and out. It was much easier with the petroleum jelly. I sped up and was able to get my dick almost all the way in.
I started jacking him off and he got a boner again. It probably felt good for him because my finger still had some jelly on them. While I was fucking him I was playing with his foreskin; pulling it back to see his head. After a couple of minutes I said “Let’s change position. Let’s do it the way you were doing it last night.” I pulled my dick out and laid on my back. He got on top of me and grabbed my dick and pointed it up. He sat on my dick and it went in fairly easy. I raised my knees up and put my hands on his thighs. Chris leaned forward and put his hands above my head to support him self and he started rocking back and forth. I matched with his rocking and my thrusts. He lay on top of me and I put my hands around his back. Chris was letting out a few moans during the thrusts.
After a few more minutes I felt that I was going to cum. I decided to cum in his ass. My thrusts sped up and I was helping Chris’ thrusts by having both my hands on his ass. After about 5 more thrusts I started cumming. To that day that was the most intense orgasm I ever had. I don’t know how much was cum and how much was part of the orgasm but it felt so good. Chris looked at me and smiled. I then kissed him and he kissed back. “Time to clean up” I said. “Yeah, I’m all slippery now” Chris said chuckling. He and I got up and went to the shower.
It felt awkward that we didn’t talk at all when we messed around. “Are you OK?” I asked while I was starting the shower. “Yeah, I’m fine.” I got the water to a good temperature, climbed in and Chris followed. “That wasn’t your first time doing that stuff, was it?” I said then got my hair wet. “Well not really.” Chris said looking down. “I was afraid you wouldn’t want to do that stuff and I actually thought you were asleep every night.” “Every night? You did it the first night too?” I asked. Chris got worried as if that wasn’t OK. “Yeah, I thought you were pretending that night too.” Chris looked worried instantly. I stood there and thought for a minute how I woke up with him. “Are you going to tell?” Chris said almost crying. “No, of course not.” I hugged him under the stream of the shower. He put his arms around me too. “But you can’t tell anyone either, it has to be our little secret.” I said to him in his ear while hugging him. “I won’t, I promise.” I broke the hug and I looked at him and he smiled. I went in and kissed him. He kissed back and put his hand on my neck. I stopped and looked at him “So who have done this with before?” I asked. “A friend.” Chris said apprehensively. “How old is he?” “13, he’s actually my friend’s brother.” He said. “And we still mess around too.” I began to think about that. “What’s his name?” “Bryce, he lives in the neighborhood next to us.” “I know him” I said. “We should see if he wants to meet you” Chris said with a smile. “I definitely want to meet the new Bryce” I smile back. I was already getting a boner thinking about a threesome and I went in and started to kiss Chris again wrapping my arms around him under the shower. Chris responded with the same thing having a boner already.