Hey, folks. This is part four 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 and discovering some new chapters with a few other friends as well. 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 outgrow some subreddits (moves past just being jerk buds). So, please watch out for new chapters that may be posted or just drop a follow. 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.

I've received a lot of advice and messages about these stories. I appreciate them all. Remembering the exploration and development of my friendships still causes me to have a raging, throbbing cock. I'm glad that it helps make some of yours throb too.

Part 1: My Best Friend Charlie, Part 1

Part 2: My Best Friend Charlie, Part 2

Part 3: My Best Friend Charlie, Part 3

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The morning hit me like a ton of bricks. Before I could even open my eyes my entire body felt heavy under the weight of the alcohol that I had drank the night before. My head throbbed and my eyes and throat were both dry. I could see the sunlight coming through the windows without even opening my eyes. By my best guess, it was probably around ten in the morning. I laid there for a moment thinking about the night before, thankful for the experience but regretting the amount of alcohol I drank. I was drenched in sweat, despite the fan being on high and me falling asleep in nothing but my underwear. As I laid there, I thought about the three times that Charlie and I had explored. Thinking about my best friend seemingly reduced the hangover effects. The more I thought about stroking with him, the more my headache subsided. The longer I laid there, the more my mind began to wander.

I thought about the first night we had crossed the line between straight best friends to what was turning into heteroflexible "jerk buds". Thinking about how we had partied with friends that night and ended up with the other's cock in each other's hand was becoming intoxicating. It was almost as if I was there. I could feel his cock swelling and I could hear his faint moans. I was imagining how his cock erupted for the first time and my first time really ever seeing another cock shoot ropes of cum. As my mind transitioned to the morning after that first night, I could feel my own cock beginning to swell in real life. As I remembered how we had slid our pants down with ease and watched porn the next morning, I began rubbing my cock through my underwear. As I remembered grabbing his cock, I reached down under my waistband and grabbed my own. I started at the head, slowly swirling my thumb around the head of my cock and then slowly working down my shaft. By this point, I was throbbing. I slipped my underwear down and tossed them off the bed, now completely naked in my bed with my throbbing cock in my hand. I just laid there, stroking my cock enjoying the memories. The three times were merging into one. My mind raced from laying on the dock the night before, feeling Charlie laying on my arm, his leg draped across me, with both of us stroking each other to us sitting on the couch, me cupping his balls, as he shot cum all over himself. As the memories flooded, I picked up the pace until I was stroking my cock at full speed.

I was definitely enjoying the moment. I had finally found a pace that felt amazing and knew that if I kept this pace up, I would be cumming in no time. I could feel it building. My body started tingling and I stiffened up my legs. I was imaging the night before, as Charlie stroked my cock fastly, his hand gliding up and down with his own cum as lubricant. Just as I imagined cumming the night before, my cock erupted, sending a wave of cum onto my body, followed by a river flowing out over my hands and onto my pubic hair. A few moments after I came, I heard something move by the door. I shot my eyes open and made eye contact with Craig. "Damn, dude. I'm sorry. I didn't know you were....." Craig said. I grabbed for the sheet and tried to cover up, wondering just how much Craig had seen. Had he been standing there the entire time? Had he just walked in? Did he see my cum or did he walk in to the aftermath of me laying on the bed panting, cock in hand, and cum splashed all over me? I covered up with the sheet and apologized, telling him I thought the door was locked. "I was just coming in to wake you up. Charlie made pancakes for all of us." I thanked him and said I would be down in a few minutes.

Craig had moved to town in 10th grade. I'm not quite sure of the whole story, but the rumor was that something had happened to his family and they decided to move away from the city into a smaller town to enjoy a more quiet way of life. Both of his parents worked from home which led to him spend most summers hanging out at friends house to give them quiet for the workday. He was a laid-back quirky kind of guy. He was an attractive, somehow pulling off the athletic nerd combo. He was tall and lanky, probably around 6 foot tall and not much more than 145 pounds soaking wet. He had a head full of curly dirty-blonde hair and constantly had to move it away from his glasses. Craig joined the cross country team not long after moving to town. Before long, he had made a name for himself as a phenomenal runner. His physique matched his sport of choice. Craig didn't have an ounce of fat on him. He wasn't ripped by any definition, but he was toned with shaped calves and a modest set of abs. During the off season, he could be spotted daily running through town shirtless with his short running shorts on. From the clearly visible bulge in his shorts, you could easily assume he was packing a respectable sized package.

His athletic abilities were balanced out by his love of reading and a desire to excel at school. Craig was rarely at parties during high school. Shortly after moving, Craig had started dating Rachel and the two of them dated until midway through their first year at college. We all assumed that the two of them had had sex, but they never talked about it. Their troubles began after they had been accepted to two different colleges in separate states. Craig had taken a cross-country scholarship to attend a major university in the next state over. Rachel accepted an academic scholarship at a university in our own state, roughly an 8 hour drive from the college Craig was set to attend. They tried a long-distance relationship the first semester; however, the distance, and I would assume the temptation of much closer love, proved too difficult and they broke up just before spring break. Craig didn't seem overly affected and chose to bury his time to studying and working out. This was the first time we had seen each other since graduation and I was surprised at the change in his appearance. He had put on some muscle mass and developed much more toned arms and abs.

After Craig closed the door, I pulled the sheet back and looked down at the puddle of cum that had collected on my stomach. I cupped my hand below it to avoid spilling it on the sheets and floor and ran to the bathroom to clean up. I washed the cum away as best as I could, threw some shorts on without underwear, and tossed a tank top on. A few seconds later, I arrived in the kitchen and was greeted by the smell of pancakes, coffee, and a group of folks who seemed way to jovial for the hangover I was experiencing. Charlie gave me a gentle smile and an approving nod as he tossed two large pancakes on a plate for me. I made my way over to the coffee pot, poured myself a cup, and joined the group around the island in hopes that the pancakes would soak up whatever was left inside my stomach and make my hangover disappear.

After we ate some of the group that had crashed the night before parted ways with the agreement that we'd meet back up in a few days to party one last time before summer was up and we all went our separate ways for the year. Craig and Sam had no plans for the day and asked if they could hang back with me and Charlie and play some videogames and swim. I was hoping for some alone time with Charlie but happily agreed since we don't get to see each other most of the year. Charlie turned the X-Box on and we settled in on the couch playing Madden, taking turns doing one versus one matches with our favorite teams. Somewhere around noon we cracked open the first beer. As the beers flowed, the smack talking increased, but we were all having a great time. After a few hours of smack talking and playing around, Sam asked if we could take a dip in the lake. We turned the X-Box off, grabbed a few beers, and headed down to the beach area. We were all just hanging out, listening to music, drinking beers, and enjoying being able to catch up with each other.

Charlie and Sam headed back up to the house to replenish the beers and left me and Craig down at the beach area. A few seconds after they left Craig broke the silence.

"Hey, bro. Sorry I walked in on you. Hope it didn't embarrass you too bad."

"You're good man. That's not the first time someone's watched me jack off and cum."

"Wait, you knew I was watching?" Craig asked, this time with shyness in his voice. Oh, shit, I thought to myself. I was just teasing him, but was he really watching me? How long was he standing there I thought to myself. I decided to just play it cool.

"Yeah, man. It's no big deal. I was just incredibly horny and couldn't stop until I shot my load. Hopefully you learned some new techniques", following my words with a playful punch to his arm. He blushed at the realization that I had known he was there and at the fact that I looked down and noticed he had a chub he was trying to conceal. I could tell he was feeling slightly uncomfortable, so I finished with a "Besides, dude. Bros jerk all the time together. No harm, No foul"

"Really?" he quickly responded. "There's something I wanted to mention this morning. I thought I saw....."

Just then, we heard Sam and Charlie loudly joking with each other as they made their way down the path to the beach area. They tossed us some new beers and we hung out for a few more hours before Charlie and Sam had to head off for work, leaving Craig and I to ourselves.

As the day turned into night, Craig and I continued drinking and hanging out. It was like it had always been, just with a hint of sexual tension left over from our unfinished discussion by the water. Our conversation had went in waves, rolling from sports, to college life, to his breakup with Rachel. We talked quite a bit about his relationship with her and the struggles he had faced after their breakup. He shly admitted that he hadn't had sex or been touched by anyone since before Christmas break. I did the mental math and was shocked at the realization. It had been almost nine months since this man had had his cock touched by another human. I couldn't even begin to imagine the sexual frustration he had built up over those long nine months. And it perfectly explained the chub I had noticed in his pants the entire evening. We were both in gym shorts and shirtless and it looked like he wasn't wearing any underwear. At times I could almost make out his cockhead through his pants and could see the bulge that he had discreetly tried to adjust multiple times. I don't know if my recent explorations with Charlie had given me a boost of confidence or had ignited a side of me that I didn't know existed, but I knew I wanted to jack off with him. I wanted to feel what I had seen over the years hidden behind those running shorts. And, as a friend, I empathized with how he was struggling sexually.

Eventually I just reached the point of not caring. At a break in our conversation I motioned towards his bulge and asked if he had any plans to take care of "that". He turned beet red and shly said "damn, dude, I was hoping you wouldn't notice that. I don't know what my problem is, man. Ever since walking in on you this morning it's just been coming and going." I told him I know how that feels and usually when I'm horny I just have to stroke one out or it'll just keep happening. He asked if I minded if he used the bathroom to jack off. "Bro, why don't we just do it right here." I said. "I've been horny all day too."

He looked at me with mixed emotions. I could tell he wanted to, but could also tell that he was hesitant. I also understood where that hesitation came from. A few weeks ago I would have never imagined jacking off with a friend, let alone jacking off a friend. "It's not gay, bro" I calmly reassured him. "It's just two bros helping each other out in a time of need." He quickly responded, "I get that man. Hell, I'm down."

At this point there was no hiding his bulge. His cock had become fully erect and was clearly visible through his shorts. I took a few steps forward until I was standing right in front of him. I sat my beer down on the table, slowly reached out, and rested my hand on his cock. He let out a sigh, but he didn't say no or move away. After a few seconds, I understood that this was happening. I slowly began to massage him through his shorts as he closed his eyes. He just stood there, eyes closed, breathing unsteadily, as I massaged his cock and gently stroking it through his shorts. After a few more strokes, I began sliding his shorts down until they dropped to his ankles. He stepped out of them and he asked me to take mine off too. His underwear looked like they were screaming trying to constrain his cock and a large stain at the head showed that he was leaking precum. I took another step forward, now only inches away from his body. I slid my right hand down his boxers and felt his hard cock against my skin for the first time.

As we made skin to skin contact he let out a low moan, almost sighing in relief that someone else was touching his cock. I grabbed it and tugged gently a few times. He reached down and slid his boxers down, exposing his cock for the first time. I looked down and was impressed by what I saw. He was around 6.5 inches long and fairly girthy. His cock was thick enough to where when I wrapped my hand around it, my fingers didn't overlap. His pubic hair was neatly trimmed with a happy trail leading from his cock to his belly button. He was circumcised, leaving a fairly large cockhead that seemed like it was begging to be played with. Below his cock was a healthy set of balls that were hanging low and slowly swayed with every stroke. I was standing close enough to where I could smell the musk from a day of swimming and hanging out in the sun. The moment was almost as intoxicating as the alcohol from the day.

The summer had been full of firsts, but not in a thousand years would I have guessed that in twenty-four hour's time I would have my hand wrapped around two of my friend's cocks. After a few minutes of stroking him, I slid my own boxers down and began stroking myself as I tugged on his cock. We were still standing in the middle of the kitchen throughout this. Not a thought in the world of what if someone came over and walked in on us. I'm not sure what it was about this time, but it felt much more intimate than the last three times between me and Charlie. Eventually he reached down and grabbed my cock, slowly stroking.

"Fuck, man. I really needed this. This feels great." he said as we both stroked the others cocks. We were standing inches away from each other slowly stroking. He would let out the occasional moan and his breathing would go from heavy to light and back to heavy. I took my free hand and brushed it up against his stomach, tracing a line down to his balls, until I began massaging them as I stroked him. He stepped even closer and I took both of our cocks in my hand, his on top of mine, stroking us both with our precum as lube.

With one hand stroking our cocks together, I took the other and began slightly tugging on his balls towards the ground. I picked up the pace, stroking faster, and thrusting my own cock into my hand to cause friction to the bottom of his cock. His breathing became heavier and his moans became more frequent. I could tell he was getting close. He put both of his hands on my shoulders and barely managed to utter "I'm going to cum, bro. Don't stop that. Oh, shit, I'm going to cum". I felt his cock stiffen, his balls tighten, and he let out a loud moan as his cock exploded. As he came, he tightened his grip on my shoulders and leaned closer into me. I felt his first shot hit my pubic hair. The shots after that flooded my own cock and grip and was quickly spread around both our cocks as I continued stroking him. I could feel his cock throb on mine and could feel his cock pulsating in my grip as it sent shot after shot of hot and slippery cum out.

The feeling sent me over the edge. My entire body shuttered as I sent an explosive cum shot that seemed to come from the entirety of my body. The first shot hit his balls, followed by a heavy flow that fell onto the floor. We stood there for a minute, evaluating what had just happened in silence. I could tell he was feeling awkward about what had just happened. In an attempt to provide some comfort, I let him know that this wasn't the first time I had done this. He quietly admitted that he had seen me and Charlie the night before, stroking each other on the dock. I had completely forgotten that we had seen him getting water when we came into the house. He followed that up by telling me that he was happy we had done this and it felt great to be able to cum without him having to jack himself off. I agreed and let him know I hope we have the opportunity to do it again.

I headed off to the master bath to shower off, leaving the mess of cum on the kitchen floor. After a quick shower, I found my way to the bed, lost in thought about how this summer had developed. There was two weeks left of summer vacation and I wasn't looking forward to it ending. I couldn't help but wonder if I would have another opportunity to jack off with either Charlie or Craig and secretly hoped for the chance to do it with both of them together. At a bare minimum, I hoped that this new found friendship would continue once Charlie and I returned to school. I finally drifted off to sleep, hoping for another good day tomorrow.