From Playing Wrestling into Something More chapter 4 Sex Stories free 2024 – Y2 Stories

I was 9 and Mason, my friend, was 10 when we started experimenting on each other, and more.

Mason went to his cousins house the next weekend after our sleepover. I kinda missed seeing him and couldn’t wait for his short vacation to be over.

I saw Mason after school and we walked together. He shared to me what they did during the weekend with his cousins. As soon as we reached an alley, he grabbed my hand and pulled me to it. He told me he missed me so much. We looked around and when the coast was clear, we went on to kiss. I don’t know if you could call it passionate, but it was exceedingly hot.

I knew he wanted me to suck him, so I went down to his crotch. He unzipped his pants and pulled out his dick. I immediately put it inside my mouth. He started to moan as his cock was going in and out of my mouth. He held my head to control the tempo.

“Ohhhh…Harrison… please don’t stop!” as he was trying to catch his breath.

I knew he wouldn’t last long because his pacing was getting faster and faster. He held my head tight as he was cumming. I had the head of his cock in my throat. His cock was starting to go limp when I removed it from my mouth.

I got up and he told me how much happy he was. He followed it up by saying that he wished he had started to shoot his cum like his two cousins.

I was curious on what he had been up to with his cousins, so he told me that he’ll tell me more about it soon. We got out and headed home.

I just kept sucking him after school whenever we had a chance. We were lucky that we never got caught while doing it in the alley.

It was weekend again and he invited me to another sleepover. Of course l was glad to spend the night with Mason. I was eager to know his stories with his cousins.

After dinner, we watched a movie with his parents and at around 10:30pm we all went to bed. I had my sleeping bag laid out on Mason’s floor, but of course he wanted me to sleep beside him.

We tried to observe if everyone was already asleep. I asked Mason about his cousins. But he told me that instead of telling me stories, we should probably do it. Before I could even say a word, Mason started to kiss me. We were getting hot and heavy with all the kissing, necking, and petting. As if by magic, we were completely naked.

Mason grabbed a bottle of oil from his desk and started to rub it on his fingers. I was lying on my back and he asked me to put my legs up and show him my ass. I was shocked when he dropped oil on it. He whispered “This might hurt at first, but please trust me. Just try to relax.”

I had always trusted Mason with all of this experimentation we had been doing. I could feel the oil dripping from my anus. He then started to rub his fingers on my hole, and slowly inserted his index finger. My jaw dropped and I closed my eyes. It was quite painful, this was the first time something went in my anus. His finger was halfway through and I was already twitching.

“Hey, are you ok?” He asked. I just nodded. So he went on to fully thrust his finger inside me. He then slowly started to go in and out of my hole. His movement was going a bit faster, and I was starting to enjoy it a bit.

Before I could recover, he was now using two fingers inside of me! Now, this was twice as painful as before. I was almost tempted to ask him to stop, but I could see Mason was extremely enjoying it. He then laid his body next to mine and started kissing me on the lips. That lessened the pain I was feeling.

He paused for a while and said “Are you ready for this?” I asked “Ready for what?” He looked down to show me his fully erect dick. I couldn’t stop him now. We’re too deep into this. I gave a sigh and just nodded again.

He slowly removed his fingers from my hole and that gave me a relief. But that won’t be for too long. He grabbed the oil again and wasted no time in rubbing a large amount on his entire dick. It was now glistening with oil. Mason then started to mount me. My legs were quite open to receive his body.

He grabbed his dick and pointed its head towards my hole. I felt his cock poking my anus. He started to insert his dick inside me. We were both novices and he was having a hard time penetrating me. I could feel he was getting frustrated, but I knew Mason was very determined in everything that he does.

He put both of my legs on his shoulders so that my anus would be wide open. He was able to find my hole again and started to thrust his dick. I felt the head of his cock again slowly penetrating my boy pussy.

We were both looking down and focusing on what’s happening. After a bit more of a push, his head was now inside of me. I was writhing in pain, but I wanted him to continue.

He asked me to relax again and that’s what I did. He pushed even further and now half of his dick was finally in. Mason was starting to smile. I knew he was having a hard time as well. We were both now sweating and gasping for some air.

He gave a final push and he was now totally inside of me. That was quite painful and yet pleasurable. He removed my legs from his shoulders and he pressed his entire weight on me. My legs were now wrapped around his lower back.

He hasn’t started to move yet. We were both savoring this moment. My best friend was inside of me now. Our bodies had become one. We both started to kiss again.

While kissing, his butt started to do some slow thrusting movements. I could feel his cock moving inside of me. He’s not pulling out all the way through. He would just move his ass up and put it back all in. He kept doing that movement and he was already pumping on top of me.

It was painful but we are starting to enjoy this. I held his head and back closer to me as he kept on thrusting. We stopped kissing and just focused on fucking. Yes, we’re not virgins anymore at this point.

His thrusting movements were getting faster and faster as we are now both getting used to this. I couldn’t believe that my friend’s dick would fit inside my anus. But here we are, two very young boys exploring and enjoying the joys of sex.

I could feel that my hole was thoroughly filled with Mason’s cock. We started to kiss again while he kept on pounding me. We got used to the feeling of having his dick inside me.

“Ohhh…shoot! This is awesome. It’s so tight and hot inside” Mason mumbled.

I was also moaning but tried to keep it low because we don’t want his folks to barge in on us. They would have the shock of their lives seeing their handsome wrestler son, fucking and balls deep inside his best friend.

A couple more of pumping and felt that his cock had probably grown bigger inside of me. My dick also started to twitch and I knew I would be done soon.

Mason’s groin was rubbing my dick whenever he would fully thrust inside me. A couple more of his pumps and I knew I had climaxed. Mason then gave one last push, put his entire dick inside of me and started to grunt. He had also ejaculated inside me. Of course we’re too young to shoot cum, but we felt that we’re done.

Mason dropped his head to my side. We were running out of air. He hadn’t pulled out yet, but he kept doing those slow pumping on top of me.

He raised his body and pulled his dick inside of me. I was so relieved that his cock was finally out. I could feel my anus was so wet. We saw some specks of blood on Mason’s cock. I started to worry and he said that it’s just normal because he popped my cherry.

He grabbed some Kleenex and wiped us both. He then laid next to me and we hugged each other. I was still in pain, but I was quite happy that we finally had sex.