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My Highschool Buddies Part 1

Posted by: Author: Age: 46 now, 15 - 18 then Posted on: 0 comments
1 likes 1365 views Category: Masturbation Male-Male Tags: highschool buddies

A true account of what my best friends and I did during our highschool years. A long story, like some of the others, but I feel the setup helps.


I became fast friends with Ian, Cory and Kevin. Once school let out for the summer we were inseparable. Ian and I would sleep over at each others houses several times a week and we'd all sleep over somewhere several times a month. Even though I was the 'new guy' they never treated me as such and enjoyed teasing me for my accent, short haircut, and 'backward country ways'. It was all in good fun and I'd tease them back calling them 'rubes' and such.

This was before computers so we'd spend most of our time outside playing ball in the street, shooting hoops, swimming in Corys pool or hanging at the beach. Out of earshot of adults we'd tell crude jokes, boast about our non-existent overendowment, put each other down about small penis size, cuss like sailors, etc.

Unlike some of our other friends that would never admit to touching themselves we all knew we were daily masturbaters and traded our small collection of skin magazines with each other and would talk about what girl we fantasized about when jerking off. I even let Ian use my room a couple times when he had relatives over and was stuck bunking with his brothers and complained he didn't get a chance for his daily release.

They all seemed so comfortable talking about this I wondered if they had ever messed around together but I never got up the nerve to ask 'Hey, y'all ever jack off together?' Little did I know they had and several things that happened late that summer maybe led up to me being initiated into their mutual fun.


Ian and I became 'besties' as he called it. An instant non-sexual attraction and bond I can't describe but I think all guys know what I mean. He was 6' tall, kind of lanky and had the blackest hair of anyone I've ever seen. So black it shined kind of purple in the sun. Above the waist he was fairly hairless. Not much in his pits and a few around his areola and the center of his chest. Below the beltline he was covered with a coat of fine black hair covering butt and all and mixed in with his curly pubes. Being from England he wasn't circumcised and had a foreskin that hung at least an inch off the end when soft. His skin tone was very white, including his penis and scrotum (which was hairless) so it stood out.

One night when sleeping over we were in his large bed talking about our upcoming sophmore year when he blurted out he was thinking of getting circumcised, he was sick of the taunts and stares in the lockerroom. I told him not to and maybe they were jealous, ignorant, or curious. I admitted I was curious and wondered how it 'worked' and if he could explain it to me.

Instead of a verbal explanation he said he'd show me the difference and to pull my briefs off so I could compare. This may sound like an odd way of doing things but we were comfortable with each other and had seen each other naked daily showering after gym. His penis was a lot different than mine. I had hair on my wrinkly scrotum where he had none and his skin was smooth with no visible veins. Pulling his foreskin back he showed me where there was skin under the bottom side of his glans that held the skin over his head and how I was scarred from having mine cut off.

I made mention of his extra long foreskin and how the others I'd seen didn't hang off so much. And how soft his skin looked compared to mine and the texture of my glans appeared rougher. Throwing caution to the wind I asked if I could touch it. Ian didn't say anything but offered me his penis by pointing it at me. I lightly pinched the end with my fingers marvelling at how soft it was and pulled it back and forth over his head a few times. This made Ian start to swell and he giggled a bit and told me to stop or he'd spew. He then asked if he could touch mine and I did the same and pointed my dick at him and he gently squeezed my hard shaft a few times and ran his thumb over my head and then let go.

We looked at each others erections for a minute or so, looked at each other, and then pulled up our briefs and talked about something else until we dozed off. There was no awkwardness or sexual tension, even with the erections. It seemed so natural to compare and we never mentioned it again.


Cory and I also became close friends. Not as tight as Ian and I but we bonded quickly. When I first met Cory I was confused by my attraction to him, I'd never had sexual feelings for another guy before. To me he was an adonis. Tan skin, swimmer/surfer toned build, blue eyes, bleach blonde hair, a treasure trail from his navel down into his shorts, perfect teeth and no hint of ever having acne. Even the smell of his sweat turned me on.

He had an easy going attitude and seemed perpetually happy. He had a natural charisma and knew it but never flaunted it. He was casual with his nudity and I enjoyed seeing him naked when we'd change to swim, I don't know how I didn't become erect. Odd thing was we had 'twin' dicks. They looked exactly the same, same size, same pubic hair color, same prominent vein running down the top of the shaft and curving around to the right just before the circumcision scar, and naturally tan.

One afternoon at my house Cory, Kevin and I had finished working out with my weights and were in my room goofing around doing muscleman poses in front of my mirrored closet doors, shirtless. We started comparing our development and how we were so different even though only four months apart in age. I don't remember now why, but we ended up in my bathroom to shave my chest and stomach. I think it had to do with me looking much older than 15. I wasn't overly hairy but had more than guys our age.

For whatever reason, Cory did the shaving and smeared shaving cream all over my chest and stomach, commenting on how my nipples got hard at his touch. His hands on my body, wiping after shaving and feeling his breath on my body as he kneeled in front of me gave me a chubby. When he got to my waist he pulled my shorts down an inch to finish and he brushed my bulge with the palm of his hand by accident. He said sorry and I said no problem, his hands all over me had gotten me kind of hard and I couldn't help it. He then gave my bulge a couple squeezes saying 'honk honk' which we all laughed at. I also remember him commenting on how spongy it was. His touch didn't make me erect but shrunk me up, I was stunned so much that he'd do that. I don't remember what we did after the shaving but I remember that Cory did apologize if it had made me feel weird but I told him since he was my friend it was ok and didn't bother me, I was just surprised.


Kevin and I also became fairly close, not as close as I was with Ian and Cory. Kevin was Corys best friend and I never understood why, they were as different as night and day. Kevin was shy, bookish, quiet and a nerd in my eyes. His hair was unkempt and oily. He had almost no muscle definition, always had a few zits, Buddy Holly style glasses and only wore white t-shirts and bluejeans or bluejeans shorts. He rarely took his shirt off no matter how hot and when swimming would burn quickly.

He never changed with us and would use the bathroom which I found odd since he wore his briefs under his trunks. Once in a while we'd all skinnydip in Corys pool but Kevin would only strip to his briefs saying that was as naked as he'd get. It wasn't like he was small in the penis department. You could easily see it through his wet briefs and it seemed average to me.

Once in a while Kevin could be really funny and he'd relax and open up. I think his attitude had a lot to do with his parents. To put it bluntly, his mom was a witch and his dad perpetually drunk. He had three sisters they doted over and treated Kevin like a slave. It was obvious he hated his life at home and would often comment on how he couldn't wait to turn 18 and just leave. I wasn't to find out until years later why Kevin was such an introvert.


That's enough of a setup for now, I need to take a break. Part 2 will have the true story of what took place late that summer sleeping over at Corys.



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