My Buddy Mike and the Dick Bets

We were both eighteen before any of this started.

My best friend Mike and I teased each other a lot growing up, and sometimes it got a little too real and serious. Firstly, we are both straight, and at least between the two of us, it was always just normal to be very comfortable with each other and even make each other get a boner as a joke, sometimes by groping the other’s dick and stuff like that. But actual gay stuff was terrifying to me, and It never went as far as jerking off together, until of course at one point it did.

We used to be about the same size, and we had similar looks. Brown, curly hair. Blue eyes that girls would call “cute”, although we had very little ability to have real conversations with them. We were always average looking guys, I would say, but Mike always wanted to prove he was somewhat “better” than me in some way, and while I wasn’t very competitive in general, it led to us finding ways to posture ourselves in various attempts at superiority.

At some point, our little jabs at each other made it so we had to compare dick size in order to soothe our egos. The first time, we tried measuring separately in the bathroom with a ruler, but when we both came back into the room with a measurement of “about five inches” we realized that we had no idea how to agree where the “start” of the dick should be, so we had to get hard in front of each other and put our dicks side by side to compare directly. 

The first time I saw it, I recall that his pinkish meat tube had a slight curve to it, whereas mine went straight forward. We pressed our dicks together, both of us pressing ourselves into the other, so that we could feel the heat of each other’s dick against our own. We both tried to angle them to find an advantage, but besides the slight difference in shape, we were pretty much identical in the cock. We dropped our dicks and gave each other a high five, agreeing that there was no clear winner. That seemed to settle both of our curiosities, at least for a day or so.

But when I measured myself again a week later, I decided that I had definitely grown by at least one tiny notch on the ruler, and when I told him about it and sent him a pic, he sent back a pic of himself as well, declaring that he also believed he had grown. Naturally, we had to compare in person again. This time, when we slowly moved our hips together, my dick touched his body with the tiniest space left, and after several careful re-attempts, he reluctantly agreed that I was actually a millimeter or so longer than him. Having my first win on the books was a bit of a thrill, and I honestly looked forward to continuing this competition as our dicks continued to lengthen.

I gloated, and I rubbed it in by telling him, “Don’t worry, your little boy cock is still beautiful.” He hated it, but it became a running joke between us.

We were right in this period of growth for both of our bodies, and we were changing literally by the day. We compared again a few days later, and then again. Within just a few months, we had compared dozens of times, and depending on the timing of our growth spurts, sometimes I was bigger, and sometimes he was bigger. Either way, we always teased each other, finding some way to justify our own individual superiority and emphasize it, whether it was length, girth, or some other natural detail like who had more pubes or who had “better balls”. Our dicks were eventually both over six inches, but I was edging over him in both length and girth, and it was clear I was going to have the larger dick when this was done.

I believe that’s why he upped the ante one time, and declared a new challenge.

“The real test of masculinity is who makes more cum,” he said once after we had measured our hard dicks next to each other yet again.

“That’s so gross dude,” I said, in shock that he would even mention that. I had lost all inhibitions about nudity with him, but the idea of cum simply grossed me out. That shit was the last thing I wanted to see coming out of Mike. 

Still, he pressed on. “You’re afraid your little baby loads won’t compare to my monster jizz volcano,” he said while wiggling his dick from the base.

My mouth dropped open in shock. I couldn’t believe he would escalate it like that. I looked down at his hard dick, then back up to his manically smiling face. We were hormonal males with no limits, but I was taken aback at the idea of actually cumming in front of my friend, whereas he seemed keen and uninhibited about it. The look in his eye gave me further pause. I narrowed my eyes at him, holding my own boner in front of me as I studied his face, looking for a clue as to what the fuck he was thinking. It was like he had something to prove, perhaps a lot to prove. It didn’t help matters that I was also growing more than him in general, a couple inches taller already, and a natural muscle tone that looked more “manly” in a way. 

He needed this, so I shrugged and said, “Aight, let’s do it,” and grabbed my dick, facing his desk.

He threw some porn on his phone and leaned it against the wall behind his desk. “You can cum there,” he said, pointing to the spot in front of me. “I’ll do it here, and we’ll see who has a bigger puddle.”

Again the idea, and talking about it, made me cringe internally. I had never brought myself to orgasm with literally any other person in the room, except maybe once or twice when I had to share a room with my brother, but that was literally a last resort situation. And on the converse, I had never had a friend jerk off in the same room as me, except again I’m pretty sure my brother was rubbing out his own loads in the top bunk while I pretended not to notice. 

But at least there was porn playing, and the pretext of a competition, so there was something to wrap my head around at least, and make this less bizarre. 

I tried to focus on the girl getting stuffed on the iphone screen while Mike started stroking his throbbing, red meat stick right next to me. His other hand gripped the desk as he leaned forward, accidentally touching my bare thigh and making me flinch away from him. Neither of us said anything as I focused on furiously stroking my own hog and trying to get to the end of this weird moment in my life. It only took a minute, because I did not want to prolong this thing, and I got over the edge by picturing that slutty girl sitting on my face, and I closed my eyes, pretending Mike was a million miles away. Then I opened my eyes and looked down at my cock as I had the weirdest orgasm of my life, with Mike clearly stroking himself inches away from me in the corner of my field of vision. 

I squirted a standard load for me, a few decently sized white ropes splashing down on the desk in front of me, followed by a bit more oozing jizz that mostly stuck to my hand and the head of my dick. I tried to let it all drip into the puddle on the desk, but obviously some of that shit doesn’t do what you want it to do. 

I saw him look over at my pile, then back down to his own dick as he came right after me, and I watched through squinted eyes, as if to shield myself from the visual that I would never be able to unsee, as he released only a single, small, white squirt followed by a few drops of clear boy juice. 

To my amusement, it was immediately clear that he had lost yet again. His face was red, as much with embarrassment as with effort from the wank sesh. 

“Nice volcano”, I said, using air quotes, trying to make sure the mood was light after a surreal post nut feeling that I was sure he felt as well.

“Damn,” he said, surprisingly jovial. “Gotta give it up, you have a hella load.”

“Yeah,” I said. “Good game.”

I held my hand out to dap it up, and he met it instinctively, creating a perfect, loud dap, but inadvertently sending drops of jizz off our hands into the air, hitting both of us in the face. We both flinched, realizing with horror what our dumb teen male brains had done. We were able to chuckle about it as we wiped our juicy cum mixture off our faces.

“Alright,” he said, and I looked up at him. 

Then, to my further horror, he added, “Just wait for the rematch.”

I looked at him with wide eyes, incredulous, as I held up my hands, holding chunks of both of our jizz that I had wiped from my face. “You want MORE of THIS??”

—[]—

The competitive sessions continued over time, and my comfort with jerking off together grew until it just felt like a normal thing, maybe even preferable to my solo wank sessions at home. It was a contest or a bet every single time, always instigated by him, but the sad part was that eventually I surpassed him in every measure. There was no point in competing anymore. My dick was unequivocally both thicker and longer than his, and even my loads were pretty much always bigger. We eventually compared both squirting distance and total volume, believe it or not, and while there were a few times where he managed to actually shoot a sizable load, I still beat him easily. Even my pubes were bushier than his, to the point where I actually started trimming them down to look more clean cut. I had passed seven inches in dick length, and I was still growing, whereas he seemed stuck at around six, or just a little under if measured honestly.

After yet another growth spurt, I dwarfed him completely in a physical sense. I was probably three inches taller than him once I hit five-eleven, and my muscles had picked up some mass after joining the wrestling team. I could even clap my ass cheeks like those girls on instagram, and I did it for the guys on wrestling team pretty much every time we were in the showers together. It became a running joke that I was “caked up”. So when it came to hanging out with Mike, it honestly started to look like he was my little brother, even though we were the same age. 

“It doesn’t have to be a competition,” I said multiple times in response to his routine requests for yet another rematch, “We could just jerk off, dude.”

But he was of the mind that, “No, that’s gay. If nothing’s at stake, we’d just be a couple fags playing with our cocks.”

I chuckled the first time he said that. There was no chill in him. He was either super competitive or some sort of gambling addict. He needed the rush of “win or lose” to make anything worthwhile, and for some reason, his obsession was centered on comparisons centered on his own crotch.

I started to like jerking off together, even more than beating it alone to be honest. At one point, I found the idea of beating it alone to be so boring, that when Mike wasn’t around one day, I literally knocked on my brother’s door to ask him if he wanted to watch porn together. Luckily, he wasn’t home, and I almost slapped myself in the face for that later.

With Mike though, I assumed that the competitions would simply end at some point when he got tired of losing. But of course, ever the instigator, he still had other ideas to escalate his penchant for cock-related games of competition.

“New contest,” he said one day while I was doing homework at his house. 

“Oh god,” I said, closing my eyes, dropping my face in my book and just waiting for whatever hellfire he was about to announce.

“We need to see who cums faster, which would make them the loser,” he said, matter-of-factly. My mind flashed to some videos I had seen on twitter of guys cumming prematurely while their girlfriends made fun of them. So now Mike wanted to prove he could “last longer” than me. I just shook my head, muttering curses about why I ever became friends with him, and what I had gotten myself into. The next thing he said was the craziest part though.

“We have to jerk each other off though,” he blurted out. 

Upon seeing my flabbergasted reaction, he added, “It’s the only way to be sure it’s fair!”