Oldest Gay Friendship Sex Stories - Page 12

Convincing my Hung Scout Camp Roomie to go skinny dipping

We were both good swimmers, so we were assigned to be instructors in the swimming class. God, that was hard on me! For hours each day I had to try now to let him or anyone else see how many times I started at his perfect body and how many times I had to stay under the water to make sure that neither he nor any of the other scouts saw the enormous erection that I usually sported. We gave several classes a day and had enough breaks between them to just sit in the shade and get better acquainted. It wasn't long before I know most of the story of his life and he knew most of mine. It turned out that we were both only children and had had no siblings around as we grew up. Surprisingly, he was quite shy around others and I began to wonder if he could be as innocent and virginal as I!
3.7 2368 words 11 mins young men  anal sex fucking  big cock  blowjob  pool  shower

First Time Fuck at 7-11

Jason had no idea, (or at least that's what I thought) that I was not only gay but very attracted to him. Jason looked a lot like the actor who plays Jack on Dawson's Creek. Dark hair, about 5'11", and with eyes that would make any guy weak in the knees. Although I was nervous about jerking off in front of him, the chance to see his cock was something that I couldn't pass up.
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Cabin Fever

Once we had our tools in hand, we began our task. George had the lawn and leaf rake and started raking up the dead weeds and grass. Bobby had the shovel, and was working at getting out the dead plants and bushes. I had the trash bag, and I was picking up all the loose trash, paper, and old aluminum cans that were scattered about. I was amazed at the amount of trash the wind had managed to blow around the cabin.
3.8 5408 words 24 mins anal sex fucking  massage  shower

Sleep over at Charlies house

Well, with all that there sports playin' Old Charley can work up quite a sweat. Now, all the guys in school like Old Charley 'cause he's a good sport. But, they get real downright bothered about having to sit in the same classroom all afternoon with Old Charley who is beginning to smell like a bull elephant in heat. So they start pesterin' Old Charley 'cause he don't take showers like the rest of them.
3.4 3078 words 14 mins locker room  shower

One Hot Night

He pulled me jeans off and smiled, his eyes partly closed with lust, as he admired my rock-hard 9-inch cock through my thong. I felt his breath as he gently slipped the thong off with his teeth. I was in my glory, harder than ever, my cock straining through its own flesh and shining with precum at the tip. He began to lick the lip lightly, with the tip of his tongue. He then went down to my heavy balls, taking them in his mouth and rolling them with his tongue, moaning softly. He then licked and sucked his way up my thick shaft all the way back to the beautiful head of my cock and put the whole head wetly into his mouth, his thick lips parted sensually.
3.7 1003 words 4 mins anal sex fucking  straight men  big cock

Rich Man's Son

My first real chance at independence came when I was sent away to the "correct" preparatory school (Groton, of course). It turned out that my roommate (Charles Lowell Carlyle) was also an only child from an old Connecticut family that had close ties to the Lowell family in Massachusetts. Both of our families were delighted when they found out with whom their son was rooming and were doubly pleased when we let it be known that we actually liked each other! Charlie was a much under his parents' thumbs as I was, but he, too, had an independent streak bursting to express itself and we both kind of re-enforced each other's feeble attempts to live our own lives.
3.4 5580 words 25 mins anal sex fucking  twink  big cock  blowjob  deepthroat  massage  shower

In the Hot Tub with Trent

Although I thought I was used to living in a "city", I'll have to admit that the size of Des Moines really impressed me at first. I've since seen Chicago and New York, so I've had to redefine my definition of "big", but that's another story. Anyway, I moved to the city, found a nice bottom half of an old duplex in what was once considered a definite slum area of the city but which has since been "rediscovered" by yuppies who have pumped a lot of money into fixing it up again. It is still old a little run-down, but is getting better and is definitely considered by my generation as "the place to live".
3.5 3872 words 17 mins anal sex fucking  balls sucking  big cock  blowjob

Brief Weekend With Shawn At Convention

We finished getting undressed and lay in the bed, holding and hugging each other. He said its been a long time since anyone showed him any affection. I told him I loved being affectionate and was hoping we could do even more. We kissed as I played with his hairy crotch and he asked what I would like us to be doing. I said I'd love to feel him inside me tonight. His eyes widened and he asked if I was sure. I told him it would mean a lot to me if he did it. He stuttered a bit and said he didn't have a condom. I told him he could do it without one. He was surprised and asked if I was sure. I said there was no one I knew who's cum I'd want inside me more than his.
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An Evening With Santiago

I asked what they did together. Santiago said the guy liked uncut cocks, and in exchange for letting him play with his cock, the guy would suck him off. I asked if he swallowed his cum, and Santiago said the guy loved to swallow. I told him I only would do this for him because we are good friends. He asked how I like to get guys off. I said I leave it up to them. I would do whatever they liked. His cock was starting to get bigger in his swimsuit. He said it could be cool, but he warned me that he shoots very big loads of cum, and it gets pretty messy. I told him that was no problem for me. He smiled and said if I really wanted to do it, to go ahead.
3.3 1684 words 7 mins young men  hairy  big cock  blowjob

After Work With My Coworker

We lived together for a few months, and he moved out.
3.2 1358 words 6 mins hairy  chubby  big cock

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