Billy, 14 (Ronny and Billy are not brothers, only cousins)
Let me start off by saying my cousins and I are very close. We've grown up hanging out with each other because we all live in the same part of town. Ronny, Billy and I are like the Three Amigos. We constantly play sports and video games and watch movies, the typical guy stuff. This story takes place one summer during a sleepover that was usually routine, but that night ended in a way that none of us expected.
Ronny and Billy are both athletic and play for their respective school sports teams, while I am not as athletic(6 feet, 200lbs) but still in decent shape. We always like t play pranks on echoer, and this day was no different. We were outside on the drive way shooting hoops and playing horse when Billy and I got the idea to 'pants' Ronny during his next shot. Billy and I smoothly positioned ourselves behind Ronny as he went up for his shot. Seconds later Ronny's shot fell and so did his pants! To our surprise, Ronny was wearing tightey whiteys! Billy and I chuckled a little while Ronny turned red with embarrassment. I thought every boy had switched to boxers by this time they were in middle school. At least this was what I had gathered from seeing my friends in boxers but also from simply living in the 21st century! I am a boxer briefs and boxer guy, while billy is a fan of the classic boxers(which we would all discover later).
After hanging out all day we made plans with our parents to stay over at my house for the night in the basement. We started with the typical guy stuff, then we watched a raunchy R rated movie with some brief nudity that got the hormones going. At this point we were in sleeping attire that consisted of bball shorts and a tshirt. During and after the nudity/sex scenes I noticed Ronny and Billy and even myself adjusting the position of or respective 'packages'. Billy had a tent due to his boxers, while Ronny and I could conceal our erections through our tighter forms of underwear. However due to the fidgeting, it was kinda obvious stuff was going on down there. But no one said anything about it till later.
After a few more rounds of video games, we decided to call it a night. Once in our sleeping bags laying next to each other on the basement floor we chatted about the hot girls Ronny and I's school, and questioned how the girls were at Billy's school. Then Ronny complained about his shirt being uncomfortable, so he took it off. Then I followed by removing mine, then Billy's came off soon after. Billy then asked us if we wanted to play Truth or Dare. I hadn't played since middle school with my friends, so I agreed saying 'sure.' Ronny had never played and took a minute to question the rules, but reluctantly agreed. I told Billy he should ask first because it was his idea to play. As is typical with TorD everyone wants truths first. We go a couple of rounds asking about puberty When did you start? Are you ahead or behind your friends? Have you noticed changes down there? etc. Then more questions like have you seen any boobs in real life? Have you seen a penis other than another family member's? Have you showered in a communal shower?
Silence in the room for 30 seconds.... after much tension I finally asked my cousins if they had ever masturbated.... More silence.... I said, 'It's ok if you do. I do, and Im proud. It's a natural thing that guys do. They say that 95% of guys admit that they masturbate, the other 5% lie abut it.' With my statement Ronny and Billy quickly admitted to choking their chickens! W went on asking each other questions like how often? do you cum?(which they both say they did) How do you get off? Are you circumcised?(which they both were) How long can you last? (me:stop and start 45min[could go longer but I get impacient] Ronny:25min[reasonable] Billy:1 hour[Yeah right!!! He is a horny 14 year old!!]) I told Billy that 1 hour is awfully long for a 14 year old and that I didn't believe him, then he confessed he lied about 1 hour.
We then participated in some 'dirty dares' but nothing gross. Hump the couch, dance like a stripper on the foundation pole, lock yourself in the bathroom and keep your clothes outside the door, etc.
Then another big question arose.... one that matters to every guy, that chicks could care less about... How long is your cock?Ronny asked, so I thought he should go first. 'About 5 inches'
I then went '6 inches'(now I am a little over 7')
Then Billy said he had never measured. I told him he should guess by using his hand, so he said 5.5 inches (which I actually believe because Billy looked further along than Ronny did even tho Billy was younger. But all in all, those are pretty decent cock sizes for 3 pubescent white boys.
The cock discussion then stopped and I asked Ronny why he wears tighty whiteys. He said that he liked the support but was also embarrassed to go out and buy them with his mother. (So being the nice cousin/friend I am, I took him out the next day to get some boxer briefs to make an easy transition to boxers)
With the truth or dare game dying down, I suggested we end the night on one last wild dare. A group dare! We all added to and embellished a group dare that would end the night. The three cousins would(with lights somewhat dimmed) strip naked and race around my circle shaped basement with our under where on our heads. We got out of our sleeping bags and said 'one two three' and then our clothe were off and the under where was on our heads. I said the first to go around 4 times and end on their sleeping bags wins the race. On the starting line I casually glanced over at my cousins to see Ronny's semi hard cock and Billys raging boner. I was semi hard at this point because of nerves and maybe somewhat horny because no one had gotten a good look at my penis before. Billy then said 'ready set go!' and like that we were running with our cocks and balls slapping our thighs and us chuckling along the way. Our underwear was all loosely located on our heads... Ronny had his white briefs, I had my red boxer briefs, and Billy had a plaid boxer. On the last lap we started pushing each other out of the way they were in the lead, but I was bigger than they were, so I was able to squeeze my way to the front of the pack. As I passed them I briefly noticed that their cocks were harder than steel, then I noticed my cock in between my legs hard and waving from side to side as a ran. Then Billy passed me at the very end and won the race.
We all looked down and noticed our solid members and I complimented them on a good race and their young but ample penises saying 'Nice dick bros, I see you weren't lying earlier' They then stared at mine hoping theirs would be a plump 6 inches very soon. They said thanks and Ronny said 'not only is it longer, it's fatter than a banana, like an ear of corn!' I told them both that with puberty their dicks would not only get longer, they would get thicker. I told them circumference around their dick was called girth.
Soon after Ronny said 'I have to go to the bathroom for a minute', I knew he wasn't going there to pee, and he wasn't going there to shit. So I said 'I gotta go too' and winked at Billy, so we followed each other (still naked with boners) to the bathroom. I said it's ok. 'As long as we touch each other, it's not gay' So with that Billy eagerly starts wanking. I follow and Ronny, disappointed that he can no longer masturbate in private kneels over the toilet bowl so he doesn't have to clean up his mess. I had never thought of that before! 'Good idea Ronny!' I said. So there we were, three cousins, three pals, three amigos kneeling around a toilet bowl going to town on our own dicks. After about 10 minutes I stood up to go get some body wash from the shower to use as lube. Billy said, 'What are you doing with that soap?' I told him circumcised people like to use it to keep their dicks from hurting. I squirted some on his cock, mine, and Ronny's. Slurping and smacking sounds now echoed through the small bathroom in my basement. I came really close to cumming 5 minutes later, but stopped to last a little longer. I noticed Ronny and Billy start to pant and breath harder. We were all whacking away occasionally stopping and switching hands to keep from getting tired. Jerking off can be a real workout sometimes... About 25 minutes into our session, Ronny says'idk if I can last much longer' 'Me neither' said Billy. 'ok guys give me another minute and we can try to all cum at the same time' I said. A minute later the panting and breathing and quiet moans increased until I said Ready? And before I could finish Ronny unleashed his milky white load into the toilet bowl. Billy sighed'AAAHHHH!' And simultaneously I yelled 'Here I GOOOOO!' and cum flew everywhere! My cum missed the toilet bowl and ended up on the back of the toilet seat. It was the most I had ever cummed in my entire life! We all three agreed that this was easily our best orgasm ever, while I have had better ones with a girl since.
What a fun and memorable night it was! I hope you all enjoyed my story, and I hope to submit more in the future. Feel free to leave comments!