The day after the pool incident we were both still obsessing over the thought of what could happen. I knew this because James called me that morning and asked if I wanted to hang out again today. Of course I said yes and that I just needed to tell my parents and I’d be over in about an hour. 

I took my little jon boat over because I had more fun driving it and also didn’t want to get all sweaty from riding my bike to his house. I pulled into his canal and parked the boat at his dock. James came out and said his parents were still home and would be leaving to go to their friend’s house for a party/cookout in the next hour or so. They asked if we wanted to come and we made up some excuse to stay home and play or do something at his house.

We decided to go inside and hang out in his room for a little bit while waiting for his parents to leave. We waited there awkwardly both thinking about yesterday, he broke the silence and got straight to the point bringing up our conversation and the “twenty bucks is twenty bucks” line I’d said to him. 

He asked me if I was actually joking and told me I didn’t have to if I didn’t want to. But immediately followed up with “But if you are willing, I’d still gladly pay you!” 

Feeling kind of awkward with the thought of getting paid to do it, I told him that I didn’t want the money. He kind of hung his head in disappointment misunderstanding me. He must of thought I didn’t want to anymore and that I really was joking or that I had changed my mind. I could hear the disapointment in his voice as we talked. I didn’t really have the courage to just come out and say what I wanted to. I’ve always been kind of shy and not much of a talker in person. Over the years through online anonymity I've become much more open. 

We ended up playing some video games in his room while waiting for his parents to leave. He was at his desk on his computer and I was on the floor playing games on the TV. While I had zoned out playing a racing game trying to concentrate and not crash. James had gone on the internet and pulled up some porn and started browsing with out me noticing. I finally realized this when I heard the sounds of porn playing which broke my trance on the game. 

So I paused my game and crawled over next to him, kneeling and looking over his shoulder at what was playing. I also saw that James was rubbing his cock down the leg of his pants, slowly stroking it with the palm of his hand. This immediately made me hard thinking about what was under his shorts. 

I interrupted him and asked if his parents had left yet and he said they left about five minutes ago. They didn’t even say bye, he just happened to see their car pull away through his window. So we both sat and watched as this girl on the screen knelt before a muscular fit guy with what looked like an eight inch cock. She would look up and give those, good girl, puppy dog eyes while she licked up and down his shaft and took the head of his cock in her mouth. 

At this point we were both rubbing ourselves through our shorts and James said that he couldn’t take it anymore and wanted to jerk off. He asked if I minded if he pulled it out and started to jerk off to what we were watching. I said no, and that I didn’t mind. So he pulls out his cock and now I get to see it much closer and better than before. 

I was right, he is bigger than I am. Like I said before I’m very average, only five and a half inches long, and only five inches around. James on the other hand was at least seven inches and looked thicker than me. If I had to guess by just me looking at it, he was maybe five and a half or six inches around. 

Luckily he was focused on the screen so much I got to stare and really take in the sight of his dick as he started to stroke it with his pants pulled halfway down his thighs. His cock had a nice helmet, about as big around as his shaft and he also had a slight curve upward in his cock. Which I found fascinating, because mine is as straight as an arrow.

At this point he looked back at me still rubbing my cock through my shorts sitting on the ground next to him. He caught me staring not at the screen but at his cock making me divert my attention back to the screen pretending like I wasn't just looking at his dick. 

He asked if I was going to pull mine out and join him jerking off. Again being naturally shy I mumbled and hesitated to answer his question. James then said that it sure looked like I wanted to, pointing out the tent that I was pitching in my pants. 

Clearly seeing what he was working with now, I told him not to laugh because I wasn’t as big as him. Fearing that he was going to make fun of me. He suprisingly said “I wouldn’t do that, you can’t be that small, and plus you’ve seen mine now. It’s only fair I get to see yours.”

So I pulled my pants down just enough for it to come out and in hindsight I should of pulled them down further. Because my waist band was partially covering me, it probably made me look even smaller. He gave it a look and again I was suprised as he reassured me that I wasn’t tiny, just average. He followed that up by making a dig at me saying “But I knew I was bigger,” and smirked at me after he said it.

We both kept jerking off to the video playing on his computer. I continued kneeling next to his office chair but sat up to get a better view (of both his cock and the screen). He glanced over at me, again catching me looking down at his cock and not the screen. This prompted him to be the bold one and he asked me if I wanted to touch it. I just kind of stared and nodded I guess because he rolled his chair back and turned to face towards me. He let go of his cock and it flopped onto his stomach with a bit of a thud as he leaned back and scooted closer to the edge of the seat. 

At this point my mind was numb and I couldn’t believe what was happening. It was just so tempting as it stared back at me. I just reached out and slowly grabbed it and picked it up just under his head. It was such a weird feeling to touch another guy’s dick. It was hard and warm but it felt nothing like mine, it almost felt rubbery. Maybe because I can feel my dick being touched, where as I only feel his dick through the touch of my hand. It felt much more girthy than mine. The tips of my index finger and thumb were just barely touching while grasped around his cock. I swear I could even feel his blood flowing through it especially as he flexed and made it jump and move. 

He looked down at me as I started stroking him. Eventually relaxing and leaning all the way back in his chair closing his eyes. I started watching the girl still sucking away at the cock on the screen. She was now more eagerly sucking and trying to fit as much of the guys cock in her mouth as possible. This was making me super horny wanting to try and do the same thing to James.

At this point I was emboldened or maybe just numb from the situation. I spoke up and said that I didn’t want the money, I didn’t mind getting nothing. James perked up at this and replied asking me “Really, are you sure?” Again I said no and that I didn’t mind. 

I proceeded to scoot closer in between his legs, kneeling in front of him. I tried looking up at him like the girl on screen did and give my best puppy dog eyes as I looked at him and his cock staring back at me. He put his hand at its base and pointed it straight up so I got to really see how big it was. It felt like it was almost as big as my face being that close to it now. I took my hand and replaced his with mine wrapping it around his cock and pointing it straight at me. 

I was now so close to it that I got my first smell of his musk. It was intoxicating, and it almost felt surreal being where I was. Now that it was pointing straight at me I saw a bit of pre-cum starting to leak out. I took that as my queue to stick my tongue out and catch it by licking the bottom side of his tip. My first taste of his pre-cum, and it tasted amazing. It tasted saltier than my own cum but still sweet and I absolutely loved it. 

I turned his cock to the side and started licking and kissing up and down the shaft a few times like I had seen the girls in pornos do. I did this until I finally worked my way back to the tip and stuck his tip in my mouth. Him being thicker than me, his cock felt big in my mouth compared to the various things I had pretended to be cocks using my own cock as a gage for size. But It still wasn’t too big that my mouth couldn’t fit around it. 

I proceeded to bob my head and wet his cock more and more with my saliva. Slowly working further down past the tip, taking him deeper into my mouth. I was making it almost half way down his cock and I decided to look up to see what his reaction to this was. I could immediately tell he was breathing heavier and really enjoying it. He was closing his eyes still and he began to thrust his hips every time I’d go down on him. He was trying to get me to go further down on his cock. 

He placed his hand on the back of my head grabbing my hair but still letting me control the pace and depth for the most part. I could hear the porn playing in the background and I distinctly remember hearing the guy tell the girl sucking his cock that she was a good girl. Hearing this drove me absolutely nuts, and I couldn’t help but moan a little with James’ cock half way in my mouth. Mimicing what the girl was doing in the porn sucking with more enthusiasm as both of us were moaning and breathing heavier. 

I tried to see how far down I could go and only made it just past half way down before gagging and choking. I think he liked me gagging on it because he sat up still holding the back of my head and immediately pushed my head back down onto his cock. I gagged some more coughing and choking on him as he tried to work his cock further down my throat, holding my head pressing me into him.

I pushed my hands against his hips telling him I needed to come up. With his dick leaving my mouth I coughed trying to catch my breath as quick as possible so I could continue sucking his cock. After a few breaths I moved my head back down on to his cock. Letting him know I was ready to continue. I kept sucking with enthusiasm but now he was controlling the pace and depth by holding my hair grabbing the back of my head pushing and pulling me off his cock. I was just moaning and being a willing mouth to receive what he would give me.

This didn’t last much longer, I could hear him getting louder and felt his cock swell even more. He told me he was about to cum and pulled his dick out and started stroking it in front of my face. I think he was trying to be nice and not cum in my mouth, but that’s what I wanted. So I told him I wanted to taste it and then wrapped my lips back around his cock. I think he liked what I said because he lasted another three seconds before cumming in my mouth. 

The first rope of cum shot right in the back of my throat causing me to gag and pull off of his cock. The second rope I was able to get mostly in my mouth and on my lips and face. I tried my best to keep from coughing and losing any of it. The last couple pumps of cum I was able to wrap my lips back around his cock and catch in my mouth. But my mouth soon overflowed causing some to dribbled out the corners. 

I honestly didn’t expect so much cum. I only came that much if I edged myself for a couple hours. And even then I still don’t know if I’ve ever came as much as he did. It was so hot, my throat was sore, my jaw was sore and my neck was tired. I swallowed  as best I could and just looked back at James. I took my finger and wiped up what I could off my face and licked my finger clean and then stuck his cock back in my mouth cleaning off what I had missed while looking up at him.

The only words he could say were “Oh, you liked that didn’t you?” I just nodded and said uh huh while continuing to keep eye contact. James said “Well we can do this whenever you want” and I told him that sounds good to me.

Not wanting it to be too awkward, we both cleaned up and I ended up leaving after. Before I left James asked me one more time if I was sure I didn’t want the money, and I told him no I wanted to do this. But this time he responded with “That’s what I thought,” and smirked at me.

I immediately went home and locked myself in my room and came so hard reliving what had happened in my head. I jerked off the rest of the day thinking about it. Each time I ate the cum off of my hand pretending it was James.

Thanks for reading. This story was mostly true, except I may have exaggerated how well I was able to handle his cock the first time. It was a bit more teary eyed and messy and inexperienced. But everything did actually happen, I just made it sound better and more experienced and slutty like I invisioned myself while doing it. In the next part I will tell you about more of our encounters over the next few weeks.