WARNING: The following text contains scenes of textual nudity and graphic sex between consenting males. If you are offended by such material, or are under the legal age of consent to read such material, please do not read any further. All persons and events depicted in the following story are entirely fictitious. Any resemblance to those living or dead is purely coincidental.
"TEENAGE MOMENTS"
by Mikey Mark
"When I'm sixteen my dick is going to be ten inches long, just like my brother's."
"Bullshit. Yer just dreamin." Daryl was like that. Always exaggerating and bullshiting just for the fun of it.
"No way man. Its true."
"Yeah? Well I say mine's thicker than your's and that's more important to chicks." I read that in a Penthouse letters column and paraded my knowledge.
"Yours thicker than mine? Hah! Look who's dreamin now!"
"I'm not dreamin. Your dick may be as long and as skinny as you are, but its thickness that counts buddy, and I say mine's bigger and thicker than yours!" I doubted if it was true, but I loved to get Daryl going. You never knew what he might say next.
"No way dude! I seen yer little pecker. You'd need a pair of tweezers and some pepper to catch that one!"
"That is so old and tired. Can't you even think of something original? Besides, that was last summer and just after swimming in freezing cold water!" Tommy Johnson had gotten a big laugh out of all the guys when he pulled my swim trunks down to my ankles in front of everybody.
"So what's yer point? And I'll bet you still don't even have any pubic hair yet either!"
"Wanna put yer money where yer mouth is?" I didn't have any pubic hair last summer, but some had just grown in and I was proud of my new-found 'manly' condition.
"Sure! Anytime sucker!"
"You're the sucker!" It wasn't very witty, but hey, we were just a pair of fourteen year olds.
"Suck me sucker!"
"Yeah? You'd like that wouldn't you?" I wanted to say "I'd love to", but I was afraid to.
"Sure! You can suck on my big dick anytime you like dude!"
"There you go on about yer big dick again!" It was all I dared to say.
"You just wish you had one!"
"Yeah, right. So why don't ya put yer money where yer mouth is like I said?" Anything to get him to pull out his dick! I wanted to see it so bad it hurt.
"Cause I didn't know you were actually serious about wanting to lose yer money."
"You are so conceited. Yer going to lose and you can't face it." This was only half true.
"Tell ya what then, sucker, I'll be happy to wager real money, or anything else, that not only is my dick bigger than yours, but I can also cum more than you and faster too!"
"Yer on! How much?" I didn't care if I won or lost, the game sounded fun!
"Whatever ya got!"
"Yeah? I got ten bucks in my pocket." I offered.
"Okay dude. Yer on."
"We gotta set some rules here to settle this bet. You got any suggestions?" My mind reeled with possibilities but I was too embarrassed to say anything.
"Well, a ruler ought to tell which is bigger, and I figure we both gotta jerk off to settle the score on who can cum faster. As for seeing who can cum the most, I'd say we need something to catch our sperm in to be able to compare." Daryl always had a cool head on.
"Yeah, I suppose yer right."
"Hey! How about jerkin off in condoms? That oughta catch everything and make it easy to see who shoots more. What do ya think?
"Sounds good to me, except for the part about which dick is bigger. A ruler only measures length and I say thickness is what really counts." I pressed the point because I felt that the thickness of my dick was my strong suit.
"Fine. We'll measure the circumference and multiply that times the length to see which one is really the biggest."
"That sounds fair, but what if one of us wins one part of the bet, but loses in another? We've got to separate our bets." I just wanted everything spelled out ahead of time so that once I had my dick out, I'd know what I was supposed to do and that might prevent me from doing what I wasn't supposed to.
"Naw, if we did that, we'd just be handing the same ten bucks back and forth. I say we wrap all our bets together to make one winner. One point for the winner of each bet, winner take all. One point for the biggest dick, one point for the fastest shooter and one point for the most cum."
"How about one point for the biggest balls?" This seemed important.
"Sure, as long as we add one point for the most pubic hair."
I knew Daryl was going to do that. He had shown me his pubic hair growing in last summer by peeling down the front of his underwear, but that was all he revealed. He figured he had a head start on me there and Daryl was always quick to press an advantage.
"Okay by me. That makes five points total. Winner take all? Ten bucks?"
"You got it sucka!"
"So, like where are we going to do this?" I was always the practical one.
"Hmm. Good question. How about yer place?"
The thought of getting caught with our dicks out by my parents was too much. "No way man. Forget it." I replied.
"Okay then, my place, tomorrow after-school?"
"Are yer parents going to be home?" This seemed important.
"Yeah, but we can hang out in the tree-house. Nobody can see us up there."
"That sounds cool." Actually, it sounded fantastic, but I couldn't really let on how I excited I was.
"Okay then, I'll see ya at school tomorrow!"
"Right! See ya later!" And with that, I rode home on my bike, with a boner the whole way. It was uncomfortable as all heck, but that just made me hornier. I strategically used my backpack to cover myself as I slipped inside the house and headed for the sanctity of my bedroom. I was sweatin from the ride home in the hot afternoon sunshine and that wild conversation with Daryl was still spinning in my head.
Was this really going to happen? Was I actually going to see Daryl pull out his cock and jerk off with it? It was almost too much to think about. Daryl and I were almost exactly the same age and body size, in the same grade at school and lived about six doors apart. Despite the fact that we hung around together almost all the time, I'd never actually seen him naked. I knew he had a dick because he showed a bulge in his shorts sometimes, but that was about it.
I was dying to see his cock. I wanted to touch it and kiss him, but I figured that might be taking too much of a chance. Daryl was the epitome of straightness. He drooled over Penthouse magazines and talked about 'pussy' almost non-stop. He also had to be one of the absolute cutest guys at school with dirty blond colored hair and blue-gray eyes. He was thinner than me, but a far better athlete, being a superb runner and natural soccer star.
Staring down at my throbbing member, I argued with myself about 'holding off' for tomorrow's competition, but I didn't really stand much of a chance and ended up pounding my young cock in earnest. I came pretty quick, and I wondered if I'd be quick enough to beat Daryl. Being a virgin, I didn't really know how fast was fast, or how much sperm was enough. All that would change the next day though, so I cleaned up my mess and tried to do my homework.
The rest of the evening and school the next day went agonizingly slow. I ran into Daryl at lunch and we exchanged a few insults about our impending match up, and I ended up getting a boner that lasted throughout most of my afternoon classes. After school got out, we met outside at the bike-racks and continued to toss around the insults and joked about upping our wager.
"So, what do you say we add something interesting to our bet?"
"Like what?" My mind spun with the possibilities.
"Like the loser has to do whatever the winner says."
"As long as there was a time-limit on that!" Always the cautious one, I had to define everything.
"Sure! Just one day after-school Loser has to do whatever the winner says."
"Okay, yer on!" It was nuts, but how could I refuse Daryl? I was flushed with the excitement of our competition, and for the first time considered the ramifications of losing. Ten bucks I didn't care about and would have gladly given to Daryl just for the chance of watching him jerk off. But doing whatever he says? Would he make me suck his cock? What else might he have in mind?
I wasn't the only one 'adjusting myself' when we climbed off our bikes in Daryl's garage and headed for the tree-house out back.
"Hey dude. Did ya bring a condom?"
"Sure, I always carry one!" Like a good little boy scout, I was always prepared.
"Like you'd need it!"
"Yeah, sometimes I do!" This was pure boasting. I was a virgin and Daryl knew it.
"Only in yer dreams pal!"
"Enough is enough! Lets just get up there and settle this bet!" I was anxious and excited as all heck.
Up the old wooden ladder we went and sat down on the floor of the rickety old tree-house. Daryl's dad had built it when Daryl was little and the place was looking a little worse for the wear. But it suited our purpose as it was private.
"Alright dude, lets do it!"
"Have you got everything we'll need?" I asked.
"Sure do! Here's the ruler and a strip of cloth to wrap around to measure the circumference. Here's my condom and we can use my watch to time ourselves.
"Sounds good to me. You go first." I was shy and figured my boner would give me away.
"You got yer ten bucks sucker?"
"Fer sure." I pulled out the money to prove it.
"Okay then, here goes nothing!"
With that, Daryl undid the button and zipper on his shorts and pulled down the front of his Calvins to reveal his half-hard cock. I was absolutely beautiful.
"So dude, what do ya think of that?"
"It's yer dick. Don't look all that big to me!" I was desperately trying to play down my excitement. Daryl's dick was big and beautiful and I knew I was going to lose.
"Yeah, right! Why don't you grab that ruler and measure it?"
I wasn't ready for this turn of events and fumbled with the ruler trying to get into position in front of him. Once I had it in hand, I reached towards Daryl's crotch but I wasn't sure how to proceed, the proximity of his throbbing cock confused my thoughts, while waves of nervous energy poured over me.
"Just do it buddy! Grab hold of it. It won't bite!"
Emboldened, I took it in my hands and laid the ruler down on top of it, pressing it down to stretch it out to his fullest. I was so nervous and excited that I could barely read the numbers on the ruler. Sweat was beading on my forehead and running into my eyes and making it even more difficult! When I finally managed to get it right, I could barely believe it as I read off the tick marks, "eight and a half inches".
"Now measure it around with that strip of cloth I brought."
It was small scrap of leather, long and thin, and it wrapped easily around him. My hands trembled being so near to his cock. It felt warm and smooth to the touch and was beautifully circumcised, having a perfectly shaped head. A drop of pre-cum started to ooze out his piss-slit while I measured his thickness. Again, I could barely read the numbers on the ruler from the sweat running into my eyes.
"Five and a quarter inches." I called out.
"Okay, you write that down while I put this condom on."
I used a small half-chewed pencil that was conveniently laying on a ledge nearby.
"Now multiply the two numbers together."
"Yeah, that's what I'm doing, give me a sec." Math was never one of my strong suits. "Eight point five times five point two-five equals forty-four point six-two-five." I announced.
"Yeah? Well that sounds about right. You got the watch ready?"
Daryl had unrolled a condom onto his cock and was holding it ready. He looked unbelievably hot. I picked up his watch and noted the second hand approaching the twelve. "Okay, five seconds, four, three, two, one, go!"
With that, Daryl started jerking his beautiful cock. He used on hand wrapped firmly about the base and used the other to slide up and down the length. His hand was moving like a blur and I was torn between looking at his cock bobbing up and down or the twisted look of passion on his beautiful face.
"Oh fuck man, I'm cumming!" He was sure making a lot of noise, and his whole body was rigid as he continued pounding away. "Oh yeah man, here it is!"
With that, Daryl's pounding stopped and he just laid there while I looked down at the watch quickly noting the time and then returning my eyes to the sight of Daryl's cock twitching around while it filled up the condom. Once his dick stopped twitching, Daryl leaned over and slipped the condom off his cock, being careful not to spill a drop.
"One minute and ten seconds." I announced, my eyes still drawn to the sight of his now softening dick.
"Yeah? Not bad eh? Now its yer turn buddy!"
So it was. Considering the fact that I had just watched my best buddy jack himself off in front of me, I wasn't too embarrassed to pull out my own fully erect member.
"Wow! That's some pecker ya got there buddy! Heck of a lot bigger than it was last summer!"
I could barely speak and I didn't trust my voice right then as Daryl was pressing close against me and his hands were only inches from my cock. When he pressed the ruler down along the top of my boner and called out the length, there was a sound of satisfaction in his voice.
"Six and three-quarters!"
"Now measure it around!"
I thought I was going to cum from the feeling of Daryl's hands fumbling around my stiff cock while he wrapped the leather strip around my cock and then abruptly left me high and dry when he pulled away.
Laying the cloth up against the ruler he called out the measurement, "five and a half".
Using the same half-chewed pencil, Daryl did the calculations and announced the fact that "six point seven-five times five point five equals thirty-seven point one-two-five."
That made his dick bigger than mine and Daryl was mighty pleased with that result, though I suppose it was a forgone conclusion anyway.
"Alright, now lets see you shoot yer load now!"
I slipped the condom over the head of my cock and felt its tightness roll over me. Daryl had his watch in hand while he counted off for me.
"Ten seconds...five...four...three...two...one...go!"
I started flailing as fast as I could. I wanted to cum so bad that it hurt. Watching Daryl do it before me just made me hornier! I figured it couldn't have been more than thirty seconds before I felt my release and hot juice started to fill up the condom while I collapsed.
"One minute and fifteen seconds, you lose again sucker!"
"Hey, are you sure? It felt a lot quicker than that."
"No way man, I'm sure!"
The last three parts of our bet were judgment calls. Kneeling on the wooden floor of the tree-house with our pants around our thighs, we both peered at each others balls and it was obvious that Daryl's were bigger and hung lower than mine. And there was no doubt that he had more brownish pubic hair than I did. But when we held up the two condoms filled with our juices, I was proud to note that mine looked and felt heavier. It took a bit of coaxing, but Daryl did concede that point. Nevertheless, Daryl had won our little bet four points to one and I handed over my ten bucks.
"Thanks dude! I'll be looking forward to tomorrow after-school to collect the other half of the bet! Same place?"
"Uh, yeah, I guess so."
"Kewl! Now lets get cleaned up and go raid the kitchen!"