First Time Masturbating With Best Friend

This story happened a long time ago, somewhere in my very early 20's? I can't entirely remember.

I met my best friend in grade school. There was a brief period where we split ways, but we reunited in high school when we discovered a lot of overlap between us and our other friends. Turns out we all knew each other, so we all formed a big group. Eventually we all graduated high school, and all our friends grew up, moved away, or went their separate ways. Some we kept in contact with, but we all ended up leading different lives, and only rarely reunited. However, my best friend and I remained very close. We stayed in the same town, and eventually ended up working at the same place for some extra money.

We were, and still are pretty good friends. Around this time, we didn't share too much about our personal thoughts, but on occassion we did open up and confide in one another. He was the first person I came out to as bisexual. He was very accepting, in that, he simply said, "Cool." and we moved on from the subject. He is straight, and he always joked with me about how horny he was, and how much he jerked off. So, there wasn't too much we kept from each other. Eventually our masturbation habits were something we would just openly talk about. We would even share what kind of porn we liked watching while doing it

As I mentioned, we worked in the same place. Whenever we had a closing shift on Fridays, we would clock out, take my car, and head to a local fast-food place. We'd pick up some food, and head down to his house, and spend the night playing videogames, and just laugh it up. Sometimes it'd get so late that'd I'd spend the night. His housemates didn't mind it, as they were usually out Friday nights anyway. 

This happened to be one of those nights. We had just clocked out of work, and we were walking towards my car, eagerly anticipating a fun night of burgers and joking around. We got to his house and headed up to his small room, and just chit-chatted the night away, while we played games, and sipped on our sodas. His housemates were predictably out for the night, no doubt off having their own fun. So we were as loud as could be, just having fun.

After a few hours, we started settling down. My friend was now sitting by his computer, and was just scrolling through some random things to show me while we talked. Just some goofy pictures, comics, videos. Nothing too interesting. He then turned to me and says, "Oh dude! This reminds me. I've been meaning to show you this." He clicked on a folder. It was full of files. "What is all that?" I asked. He clicked on one, and it was pretty much what you guessed: Porn. Of all kinds too. All categorized. Some of it live action, some of it hentai, some of it in images, some in comic form. 

"Fuck. How long did it take you to collect all I this!?" I asked, laughing.

He answered, "It wasn't easy, but I'm gonna have to either delete it all or move it to an external drive soon... Did you want some of it?"

"Yeah, sure. Let's see what you have." I said. I reached into my bag, and pulled out a thumb drive and put it into his computer. 

I sat on his bed. "Show me the comics." I asked. We skimmed through some of them, and I chose out which were the hottest ones to me. Which ones spoke to my cock's sensibilities that is... He put them on the drive. "Want to see something cool!" He asked. He wandered the cursor over to another folder, and clicked an icon. It loaded up a Japanese hentai/sex game. "Pretty cool huh!?" He said. "Whoa! How do you play? What do you do?" I asked. He showed me the ropes of the game. Basically, the game had a flowchart of scenes you could unlock. Each one would lead into sex scenes featuring two, very hot, 3D modeled girls. Pretty basic stuff. But as basic as it was, it was starting to make my cock leak in my underwear. 

We played through the game, just joking around with it at first. As we went on however, our joking started turning into very lewd comments about what we would do with the girls, or any girl for that matter. I was starting to get very horned up. I looked over to where my friend was sitting and saw him pitching a tent in his pants. "Holy shit dude, are you popping a boner!?" I said. "I can't help it, bro! It's good shit!" He laughed. We were both having a good time, just smiling, laughing, and being crass. No one was home still, so we were as loud as we wanted to be. But, as we clicked on, we started getting quieter and quieter. We both stayed silent as we watched the 3D anime girls fucking and sucking on the screen. I had a huge erection at this point, and I needed to let it out. But, I had never masturbated with anyone before. I had thought about it, and fantasized. But, I didn't think I could ever do it, let alone with my best friend in the room.

I'm not sure what it was. The game, the bawdy talk, or seeing my friend's cock bulging in his pants. But I got overwhelmed with a desparate need to masturbate, right then and there. Feeling bold, I went ahead and quietly unzipped my pants. I reached into my underwear and started stroking my throbbing, hard penis. My friend didn't seem to notice at all. He either didn't want to say anything, or he didn't want to call attention to it and make it weird. The thought rushed in my head, that I shouldn't be doing this with my friend, but the whole taboo-ness of it made me that much hornier. The atmosphere in the room suddenly changed. It went from silly and lewd, to a very quiet, intense silence. My nervousness was calmed however, when I decided to have another glance at my friend's bulge. Only, I saw him squeezing it now. 

"Oh good, you're doing it too?" I said.

"Oh, yeah. Why not!? It's just us right?" He chuckled, putting his hand in is pants.

We never took out our cocks. They stayed wrapped in our undies while we beat off in silence. The only sound being the filthy 3D girl moaning coming from the speakers. We were rubbing off for a good 30 minutes, when I started feeling the familiar tingle in my balls. "Fuck. I don't wanna cum in my pants. Should we stop?" I asked. "Hold up, I got you." He said, grabbing me some tissues. I lowered my undies and let my penis get some air. He looked over at me and goes, "Shit, that pretty big, dude." I was flattered, so I asked if I could see his. He declined. I later would find out that he was very self-conscious about his penis-size. So he kept his wrapped up, but kept stroking it vigorously. Making his bulge rise up and down rapidly.

I gave myself a few more tugs, and I felt my semen making its way out. "Oh dammit. Fuck... I'm gonna cum..." I quietly said, wrapping the tissues over my cock. I shuddered intensely as I unloaded what felt like several ropes of cum. Some of it oozing out the sides, running down my shaft. I looked to my friend, and saw his arm going faster and faster. Hand shoved down his pants, stroking his penis. When he came, he didn't moan out loud. He instead started with a low murmur, then finished off into a series of deep grunts and heavy breathing. I did hear him mutter, "Hmmmphhh... Fuck. Fuck...Hmmmmm." He had his eyes pressed shut during his ejaculation. He then let out a deep, satisfied sigh.

"Did you just cum in your pants?" I asked.

"Excuse me a minute." He stood up and waddled over to his bathroom. I heard his trousers hit the floor while he ran the sink for a bit. I threw away my wadded cum tissue, and put my cock away just in time for him to come back. His pants were on, but he was holding what were the remains of his sperm covered underwear. He tossed them into his dirty laundry pile in the corner.

The room was now very warm, and smelled like hot breath and cum. If his housemates had walked in at that second, they would have to be stupid to not know that something sexual had just happened. Things then were a little awkward. I wasn't sure what the next step to something like this would be. We kind of sat around just looking at his porn collection some more. Then in a flash our attitude changed and we started joking around again. Not sure what it was. By then it was already one in the morning, and I thought I should go, lest things suddenly become awkward again.

When I got home, I knew things would be okay when he messaged me saying, "Dude, when you left I did it again! I busted hard! That was fun doing it with you." I replied and said that I had a blast as well, and that I would totally be up for it again if it came up. That was the beginning of our soon to be many jerk-off sessions. We did it a lot in the coming years. Eventually he moved back in with his parents, and it didn't happen so much. Unless they were away, or he was at my place. Then, I got a girlfriend, and we stopped doing it altogether. That is until I told her that me and him used to be jerk off buds. She became terribly curious about it, and it led to us all starting a strange, and wonderful masturbation three-way tryst that lasted a long time. Tons of sperm and vaginal fluids were swapped between us. But, when she and I broke up, my friend and I resumed our mutual masturbation activities. Eventually those slowed down as we got older, and work became more of a priority in our lives.

It's been a long time since me and him have shared a wank together. There's many stories I could share about us that are all fun to recall. But the first time was one of the best.