True story from my horny youth. I later found out Donovan had other experiences with a guy I ended up hooking up with in high school
In eighth grade, I played basketball for my middle school team. Our league had 'A' and 'B' teams-based largely on talent. I played on the 'B' team.
By the time I reached middle school, I was masturbating an average of three times a day-always first thing in the morning, as soon as I got home from school, and when I went to bed. It was not uncommon to rub one out in the evening, as well, while doing 'homework.'
I was also aware by this point that I was attracted to other guys-often, my first thing after school jerk was recalling some of the guys I had seen in the showers after gym class.
To give you some idea of what I looked like, by eighth grade I had finished my growth spurt, and already stood six feet tall. I was a little heavy, around 230 lbs, and had already developed a fair amount of body hair under my arms and above my dick. Speaking of which, I was (and am) a grower, not a shower-soft, my circumcised dick was about three inches, but I get a good 6 3/4 inches hard. These were my dimensions then, as well. My cock sticks straight out from my body, with a slight bend to the left about halfway down the shaft. I have auburn hair and brown eyes. All in all, I was a pretty average eighth grader.
Alright, enough background. As I mentioned I was on the 'B' team, and we were playing in the end-of-season tournament in a town about 2 hours away. I convinced my mom to get a couple hotel rooms near the tournament site, rather than drive there and back over the two days of the tournament. My mom, her boyfriend, and my grandmother would stay in one room, and I would stay in the other with three of my teammates (we carpooled to games).
For the overnight, I was rooming with three guys with whom I was friendly, but not close friends: Donovan, who was a stocky kids with curly black hair and of mixed race with a southeast asian influence; Joe, who was a tall lanky white kid; and Bear, who had an olive complexion and stood about 5'6'.
I had seen Joe and Bear naked in gym classes in seventh or eighth grade, but had never seen Donovan's dick. I knew Bear's had grown a bit, and stuck out from his groin about 3-4 inches when he was showering. He had some pubes, but was still growing. Joe, even though he was about my height, hadn't yet really seen his cock grow, and it stuck straight out from his hairless crotch about two inches.
So, after the opening games, we checked into the hotel. There were two beds in the room, and we'd gotten two roll-aways. It made for tight quarters, but we preferred it to sharing (I wouldn't have minded, but...).
We were all sweaty from the game, and began to shower. Being all guys, and used to the locker rooms at school, we kept the door open to the bathroom so people could do other things to get ready for bed (brush their teeth, etc). I took advantage to scope out Donovan's package-he was the best hung of us, about four inches limp with a large cock head-he was the only one of us whose dick truly dangled. I was impressed, and little turned on.
As the showers wrapped up, we spent some time watching tv and lounging about the room. This being 1992, we were almost all in briefs-white ones for Donovan and I, gray bikini briefs for Bear. Joe was the most modest of the group, wearing sweatpants.
I didn't have set plan in mind, but I had brought a few Playboy magazines with me to share. As we lounged about, I brought them out and showed them to the rest of the guys.
This started a conversation about every 14 year olds favorite topic: sex! As we were sitting on our bunks, flipping through the magazines, I felt my cock stiffen. I was lying on my stomach, as were the others. After talking for a bit, Bear stood up to go to the bathroom.
As he stood, Donovan noticed his bulge and said 'Hey Bear, nice boner.' His dick was pushing out the front of his briefs about 5 inches. Bear blushed and didn't say anything.
Donovan, perhaps realizing he'd embarrassed his friend, said 'Dude, no worries...I'm hard too.' He then sat up on his knees, and his erection was obvious-it was pressing up against his stomach, barely held in place by his underwear. The bulbous head was clearly outlined beneath the thin material. My own cock twitched and got even harder.
'Yeah, me too.' I said. I also sat up, my dick tenting my briefs to their fullest. 'Joe, what about you?'
'Um, yeah..' Joe was under the covers of his bed, but didn't show his arousal to us the way we were.
Bear just shrugged. 'Yeah, I guess it's no big deal.' And with that, he went into the bathroom, and we could hear his piss hitting the toilet.
While he was in there, Donovan and I continued to chat flip through the magazines. Joe announced he was going to sleep, and tossed his magazine aside.
Bear emerged from the bathroom, his bulge no longer as prominent as he'd softened a bit while pissing.
As we were chatting, Bear mentioned that he had a condom in his wallet. Donovan and I were intrigued, as we'd never seen one.
'Can I check it out?' asked Donovan.
'Sure. I have another one at home.'
Bear handed Donovan the condom, and Donovan took it out of it's packaging. As he examined it, our talk turned to our dicks. We each discussed their quirks-did they bend? Did they grow a lot? We decided to compare boners.
We were each nervous-I know my heart was beating a mile a minute. I was about to fullfill a desire I'd had for at least 3 years-I was going to see another boy's boner!
Glancing at each other, none of us wanted to be the first to expose our stiff dicks. Sure, we'd seen each other soft, but this was a whole different thing-we were sexually aroused, and each of us was undoubtedly worried about being accused of being a fag.
Worried that the moment might pass, I reached down and flipped my boner out the fly of my briefs. I gave it a light stroke as I showed it off to my teammates.
'Nice one.' Donovan complimented me. As he did so, he pulled his briefs down and hooked them under his balls. His cock, stiff as a board with an upward sweep, bounced out. Slightly veined, capped with his round head, it looked awesome to me.
Bear soon followed suit, also pulling his hard-on out of the fly of his briefs. It stuck straight out, about 5 inches, with a narrow head that was barely larger than the shaft.
Using our own fingers, we each took rough measurements of our own cocks. To my surprise, I was the largest-slightly, over Donovan.
As we sat there, our dicks exposed, Donovan decided to put the condom on to see what it felt like. He stretched it over his cock, unrolling it down to his full bush. I thought it looked really hot.
Since we'd exposed ourselves, I'd been giving my own cock an occasional stroke or two. We hadn't really discussed masturbation. I was as turned on as I'd ever been, and really wanted to jack off with these guys. I was also afraid of going too far, and being labeled a queer.
Fortunately, I had help.
'So, how often do you guys jack off?' The question came from Donovan, whose condom-covered cock was almost visibly throbbing.
I, being a slight coward, responded with a question: 'how often do you do it?'
'Ah....about once a week' was his reply. With his admission out there, I felt more comfortable admitting that I jacked, but did not admit how much I did it.
'I do it about once every day or so' was my reply.
Bear was still hesitant. 'I don't really jack off. I prefer the feel of a mouth.' Bear had earlier told us stories about his supposed encounters with a couple girls in our class. I don't think either Donovan or I really believed him.
With our admissions (mostly) out in the open, I decided to push things forward. 'I don't know about you guys, but I've gotta take care of this or I'm not going to get any sleep.'
And with that, I reached down, wrapped my hand around my rigid penis, and began to stroke. Donovan and Bear were both watching me.
'I'd like to, but I have to use lube. I didn't bring any with me,' Donovan said.
'I've got some shaving gel you can use,' suggested Bear.
'Yeah, that'd work.' Donovan stood up and walked over to the bathroom, his dick wagging in front of him. He returned with a handful of shaving gel, which he proceeded to smear over his cock after removing the condom.
With Donovan starting, Bear relented and reached down to begin playing with his dick. I was sitting on the edge of my bed; Donovan was back on his haunches, sitting with his legs tucked beneath him; Bear was laying on his side.
I was incredibly aroused. I knew I would have to work to not shoot my load right away-and I wanted this to last. As I continued my practiced stroke-four quick strokes near the head of my dick, followed by a long stroke all the way down, I watched closely as Bear and Donovan stroked their cocks. Donovan, like me, was using a full fisted stroke, while Bear was stroking with three fingers on the top and bottom of his shaft.
'I wonder who will cum first?' I wondered aloud.
'Probably me' replied Donovan.
'I dunno, I'm pretty close' I replied. That was the end of the conversation for a few minutes.
The only sounds in the room was the sound of hand stroking flesh, with the wet sound of Donovan's masturbation the loudest. Each of us was making quiet moans or other sounds of pleasure.
Suddenly, Donovan gave a gasp and he sat up straighter, raising his ass off his feet. He brought up his other hand, and used it to catch his cum as it began to squirt from his slit.
Seeing Donovan blow his load brought me right up to the edge, and then I was over it. I came as hard as I ever had before, my semen squirting forcefully out across the carpet in the hotel room. My dick was spasming with great intensity, and I was astonished at how much jizz was firing out-I had already cum that morning.
As I came down from my orgasm, I noticed Donovan get up and walk to the bathroom to clean up. The foamy shaving cream was still covering his softening dick and was in his pubes. I followed him a moment later to pee, as I always have to after blowing my load. When I came out, Bear had stopped stroking and was back under the covers.
'Did you cum?' I asked him.
'Um, yeah. I wiped up with a tissue.' I was skeptical, but didn't have a way to force the issue.
We turned out the lights, and sleep began to overtake us. I was so aroused by what I had seen, however, that I jacked off quietly in my bed, squirting another load into the sheets.
This was the only circle jerk I experienced in my youth, and I wished I'd had opportunities for more. I wish I'd invited Donovan over for a sleep-over, but it wasn't to be.
Anyhow, that's my story. Thanks for reading. I hope you enjoyed it!