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Hey, folks. This is part three of my series I'm calling My Best Friend Charlie. This is a true recount of how my best friend and I turned a new chapter in our friendship. While some of the details and conversation are thrown in to make the story flow better, the actual events is how my exploration with Charlie transpired. Charlie and I explored a lot and some of our explorations may outgrown some subreddits. So, please watch out for new chapters that may be posted. I spent a lot of time exploring my sexuality, so please stay tuned for other series that follows my time in the military, my times finding friends with benefits, first times to the bath house, random explorations with straight friends, etc.
Part 1: My Best Friend Charlie, Part 1
Part 2: My Best Friend Charlie, Part 2
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Charlie and I were enjoying our summer. After being home for a week and relaxing, I started my summer job working at my parent's restaurant. My days, and most weeknights, were spent serving tables and stashing away money for the upcoming school year. Charlie started a summer job working for a family friend at their farm. Our nights were typically full of hanging out with old friends, listening to their stories about life at their new schools. Many of our friends had moved far-and-wide to go to wherever it was they had been accepted. And, as it usually goes, a few stayed in our hometown and started apprenticeships in trades and working in family businesses. All of us seemed to enjoy the decisions we had made so far. d partying at my parents lake house. When we weren't just hanging out enjoying the downtime we were partying at my family's lake house.
Growing up I didn't realize just how fortunate we were. Our lake house wasn't very modest. Nestled on the banks of our local lake, it was about a 30 minute drive from the town we lived in. It sat on about two wooded acres with about 500 yards of beachfront. My family had it completely renovated and the end-result was a five-bedroom modern home with a large living room that could comfortably host 15 people. The living room was separated from the kitchen by a large island and on the other side of the island was a series of glass doors that served as both windows and access to the back deck. The back deck was fairly large, enclosed by glass windows that could be raised to let the breeze flow through the house. On the deck was a L-shaped bar area with bar stools, a pool table, an ice hockey table, and an outdoor seating area that sat in front of a large projector screen for watching TV. The stairs led down to a stone walkway that curved down to the lakefront. We had sand delivered to make a beach area and installed a firepit with swings and had several Adirondack chairs by the water. Off to the side was a two-story dock where we kept our pontoon boat on the first floor and a seating area on the second. The dock also had a ledge off the side where you could jump into the water for swimming. If we weren't working, most of our evenings were spent at this house enjoying the company of our friends and exploring the new chapter of our friendship.
It had been a week or so since our first exploration. Throughout those weeks the scene replayed in my head. I couldn't help but think about it. The excitement of seeing my best-friend's cock hard. The thrill of feeling his cock throb. The amazement at feeling his cock swell and his balls contract as he erupted a stream of cum onto his chest. His moans and heavy, raspy breathing echoed through my mind. I couldn't wait for the next opportunity for me to explore with Charlie. At the same time, I was trying to answer my own heavy questions. Am I gay? Does this make me bisexual? If we do anything further, will it mess up our best friendship? How do I bring it up again without seeming overly eager to play with my best friend's cock?
Friday finally came around and Charlie and I were both not scheduled to work. We headed out to the lake house around noon with a few friends and planned on cooking out and day drinking. The six of us spent the day eating, drinking, swimming, and just hanging out. As any tipsy college-aged kid does, as the beers became more plentiful we began thinking with our dicks. One of our friends asked if we could invite some more people over, in hopes that we could each get lucky with some of the girls. I obliged and sent a text to everyone I could think of. Before long, we had ourselves a party. There were probably around 25 people that showed up. The booze was flowing, the music was going, and we were all having a great time.
The night was fun. We were dancing, drinking, and having a great time. Somewhere around midnight one of the girls brought up the idea that we should all go skinny-dipping. None of us hesitated. We all stripped down and ran into the lake. I'd be lying if it didn't turn me on. It was like I had found a new side of myself. Not only was I noticing the incredibly hot women naked around me, but also experiencing the thrill of seeing cocks bounce and swing as they ran to jump into the water. It was truly the first time I had ever paid attention to the differences in different men's cocks. Some were naturally big, even when soft. Others, hopefully growers. Balls hung low and high. Some naturally hung to the left, while others hung directly down or to the right. Some were uncut, while others had mushroom heads. It was truly mesmerizing. Luckily, and I'm not sure how I controlled myself, my own cock didn't decide to reach for the stars. We all swam for around 10 minutes then headed back up to the beach area.
Throughout the night there had been a steady stream of folks coming in and out of the main house. I'm not sure if any of our friends had gotten the result they hoped for that night, but I know me and Charlie had not. As the morning pressed on, the few that stayed behind at found themselves on the couch or one of the guest bedrooms. We still had the music playing and it seemed that everyone was dead to the world. "Bro, it's only like 3 a.m., why is everyone passed out" Charlies asked. "I have no idea, man. I'm not tired at all." Neither Charlie or I were ready to call it a night. Charlie asked me if I wanted to grab a few more beers and go drink down by the water. I eagerly said yes and grabbed a few and we headed off to the beach.
We both sat down in chairs beside each other. We sat there in silence for a few minutes just enjoying the moment. The moon was shining bright and reflecting off the water, almost perfectly illuminating us with light that was dim enough to be relaxing but bright enough where we could see each other. As the silence pressed on, I began worrying that our friendship had been effected by our exploration together.
Charlie broke the silence first. "Look, bro, nothing is weird between us, right?"
"I hope not." I responded. "I've been thinking about it a lot this past week. I really enjoyed it and the thought of it happening again turns me on. But, I don't want to ruin our friendship."
"Bro, me too. I've been thinking about it and hoped you weren't weirded out. I enjoyed it too. It felt effortless and just like best friends helping each other out. I hope we can do it again."
I let out a sigh of relief. My fears of our friendship changing were relieved. "I don't know about you, but all of this alcohol has me horny as hell" I said.
"Me too, bro!"
"Let's do it again then, man!"
Unlike last time, we had a few people who ended up crashing for the night. I thought about it for a minute. Should we go back to the house? Is out here safe? What if someone catches us? I asked Charlie to head back to the house and make sure everyone was passed out. He got up and stumbled his way back to the house. After a few minutes he came back and let me know that everyone in the house was dead to the world.
"Bro, we could just jack off on the dock. It's kind of hidden from the main house and I doubt anyone is going to be out on the lake at this time." I mentioned. So, we got up and headed over to the dock. We sat down on the edge and let our feet hang off the side into the water. Neither one of us had our phone with us, so porn was out of the question. Oddly enough, he didn't even bring up porn. We were both still shirtless from swimming all day and we had our swim trunks on. As we sat next to each other, I eventually reached over and put my hand in his lap. His cock was already half erect. I could feel the chubniess of his cock through his trunks. I gave it a gentle squeeze and started slowly massaging it through his trunks. He let out a small sigh of relief, as if he had been horny all night and just couldn't find a way to release it. As I slowly massaged, I could feel it growing. It twitched as it swelled until it seemed as if his swim trunks could barely constrain it. I could feel his head outline through them and gently swirled my thumb around the tip of his head. He reached over and started doing the same to me. As he gently messaged I could feel mine becoming more and more hard.
After a few minutes I slipped my hand down his trunks. It felt just as great as I remembered. I slowly wrapped my hand around his cock and started stroking him underneath. After a few strokes, I reached over with both hands and pulled his trunks down. Where his trunks were keeping his cock under wraps, the second I pulled them down it shot back and hit him in the stomach. After his were completely off, I slipped mine down and sat them both on the dock behind me. For a few minutes we just sat there enjoying the feeling of stroking each other's cocks. I went from stroking him slowly, to swirling my thumb across the tip of his cock to spread his precum around. Then, would stroke down his shaft until I reached his balls and slowly caress them.
Neither one of us were in a hurry. As we sat there on the dock, enjoying the feeling and the moonlight, it seemed that both of us were just slowly exploring the other. Unlike last time, which seemed like a race to the finish line, this time seemed like a marathon. I don't know how to explain it other than it just felt more raw. This time, I noticed every vein. As I slowly stroked I could feel the two large veins that were on the top of his cock. I noticed the large mushroom head he had and how sensitive it was. When I would concentrate on his head, slowly swirling my fingers around, he would tense up and stiffen his legs and his breathing would become more heavy. As I massaged his balls, I could feel the veins and hear him sigh as I gently tugged on them. He let go of my cock for a minute to enjoy the moment. With the extra freedom to move around, I reached over with both hands. I began stroking him with one and tugging on and massaging his balls with the other. This moment was like ecstasy for me. I was sitting in the moonlight with my lifelong best friend, both of us rock hard and naked, stroking each other.
As we continued stroking, we both laid back on the dock. We were laying right next to each other, skin to skin. He put his leg over mine, interwining us even more. I stretched out my arm and he laid his head on my shoulder. This was definitely the closest and most intimate that we had done this. As we laid there on the dock, bodies connected, and staring up at the stars, we both stroked the other.
We were following each other's pace, stroking the other at the same speed. We were truly getting to know each other's cocks. As he stroked me I let my hand wander down below his balls. I slowly started massaging the area just below and he arched his back up a little, almost inviting me to explore more. For a second I thought about moving even further down, but I didn't want to ruin the moment should it be ill received. I slowly moved my hand back up and found his cock again, this time picking up the pace.
I could tell we were both nearing the finish line. Our breathing had gotten heavier, our balls a little tighter. I began stroking him faster and faster, alternating between a swirling motion and a full on up-and-down stroke. He mimicked my motions on my own cock. After a few minutes I felt the tell-tell sign.
Suddenly his cock seemed to grown even harder. I could feel the veins stiffen up. His breathing became unsteady. I imagined his body was feeling the same as mine. My own cock felt like it was warming up like a fire had been set to it. I could feel my balls tighten up close to my body and a warm flush start spreading all over my body, starting in my toes and working its way up to my head. His cock began throbbing and he arched his back up slightly, causing his head to burrow deeper into my arm. He let out a moan proceeded by a "fuck, fuck, fuck, bro...... don't stop. don't stop. yes. keep doing that." Then, all of a sudden, he erupted. Even laying on our backs looking up at the stars I could feel it through his cock. His cock twitched like a bull at a rodeo. I could feel it as he pumped shot after shot of cum onto his body. In his own ecstasy of the moment he had stopped stroking my cock. After his cock and cum shots calmed down, the last few spasms from his cock sent a slow flowing river of cum down onto my hands. His breathing calmed and he just laid there for a second. "Fuck, bro. I needed that. Holy shit that felt amazing" he said. I was still holding on to his cock feeling it slowly deflate after a victorious eruption. I let go and slowly started to stroke my own, forgetting that his cum had covered my hand. Using his cum as lube, I started stroking and he apologized. "Fuck, man. I'm sorry. I got lost in the moment. Let me finish it for you."
He grabbed my cock and started stroking like we were running out of time. As he stroked my cock I felt the feeling come back. The warmness started in my toes and quickly spread to the rest of my body. I reached down with my cum soaked hand and started massaging my balls as he stroked me until I felt it. It was like lightening struck me. My whole body convulsed and I erupted cum onto my chest, followed by shot after shot of cum, sending a stream from my chest down to my pubic hair. My cock had never been this sensitive before. Every stroke sent a lightening bolt through my body. It was amazing, but almost unbearable. I let out a laugh as I reached down and grabbed his wrist to get him to stop stroking me. "Fuck, man. That was the best cum shot I think I've had."
"Yeah, man. you almost hit yourself in the face with your own cum" he said while laughing.
Both of us sank back into the dock, staring up at the stars.
"You know, man. I'm glad we figured this out. It's pretty great just to get off with you." he said.
I couldn't help but agree. We laid there for a few more minutes, still soaked in cum. Afterwards we decided to go for a swim to clean ourselves off before heading back to the house to go to sleep for the night. We stumbled our way back to the house and tried to be extremely quiet. I'm not sure how long we had laid there on the dock stroking each other's cocks. I only hoped that no one had seen us.
As we walked into the living room, I noticed another friend of ours, Craig, was in the kitchen pouring himself a glass of water. We made eye contact for a second and gave each other the "bro" nod, before making our way to our own bedrooms.
I crashed down on to the bed and couldn't help but think about where our friendship was headed. The summer was halfway over, but I hoped Charlie and I could explore our new chapter more. I couldn't help but think ahead to when we both went back to school too. Eventually I dozed off, hoping that the hangover wouldn't be too bad in the morning.
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