Part one: Ryan's story
I broke up with my long-time girlfriend about four months ago. Things just weren’t working for us anymore. It’s a good thing we realized it before we got married.
Lately I’ve been warming up to a new girl where I work. I’m just going to take it easy and let her get to know me better, and when I think the time is right I’ll ask here out, maybe for a casual date. I know she likes baseball, so maybe I’ll suggest we take in a game together, or something like that
But that’s not what I want to tell you about. I was twenty-four when this started. I have a sister two years older and a brother who is nine years younger, so he and I have never been close. I always considered Mason more of a pest than anything else. My sister Julia had been married to Taylor for six years and he was now twenty-eight. He wasn’t particularly good-looking, but he was affable. Nobody in my family could be called handsome. We’re all pretty average.
Besides his easy out-going personality, Taylor’s most distinctive feature was a full, almost black beard which he kept closely trimmed. I was envious. I inherited my red hair from my grandfather. None of the other family members has red hair, only me.
Taylor had worked for years in a plumbing warehouse before becoming a professional plumber. He was strong, but not muscular. Years of junk food and beer had taken their toll. He wasn’t fat by any means, but didn’t have the body he’d had at one time.
When I was growing up we had been a one-car-family with a two car garage. Dad had converted the other half of the garage into a workshop. He liked to build things. Since Dad was no longer around I parked my pick-up in the garage and had turned the other half into a “man-cave”. It had an old futon, a couple of leather, swivel office-chairs, a TV and a fridge. Nobody ever went in there.
One Friday evening Taylor showed up with a six-pack and suggested we go in my private place and watch some obscure game that was on. The game wasn’t interesting and he persuaded me to put on a porn channel. After a very few minutes he asked if I jacked off. When you think about it, that’s a pretty dumb question. I mean, you already know the answer. As I said, I'm between girlfriends, and I was jacking off more than usual…a lot actually.
He said, “Do you want to do it now?” I was a little taken aback.
“Now? In front of you?”
“Well, what I meant is, I need to, and I wondered if you wanted to do it at the same time.”
I asked, “What brought this on?”
He grimaced, “It’s simple, Ryan, I don’t get much sex from your sister, and my nuts are bursting.”
I could believe that. Julia had always been a religious nut, with church going taking up most of Sunday, Wednesday evenings and on Friday evenings she did something having to do with church business. Church is where she had met Taylor, though it was obvious he didn’t share her enthusiasm.
Taylor was rubbing his already hard cock through his pants, and it was obvious he had a big cock, which peaked my interest. Something else I had inherited, although I don’t know from who, is a big cock. Really, my cock stands a full eight inches when hard, and is big around. I’m not cut, but my foreskin only covers about half the head and disappears when I’m completely hard. It’s sort of bullet shaped.
I shrugged, “Okay, I guess so.”
Taylor stood up, unbuttoned the top button of his pants, unzipped them and pulled them and his briefs off, then pulled off his T-shirt so he was completely naked except for his work-boots. His cock was amazing. It wasn’t as fat as mine, but it was a good inch longer, which is a big difference in cock sizes. Whereas mine stands straight up, his has a slight curve, pointing toward his belly button. It also has a knob-like head which was a purple color.
He looked at me. “Well?”
I hadn’t thought about getting naked, but it seemed wrong now to just pull my cock out, so I stood up and stripped. We sat back down and I flopped my semi-hard cock around to make it get hard.
Taylor said, “Nice,” which made me feel more relaxed about what we were doing, or about to do.
I got back up and found a can of that yellowish motor grease that had been there for years. We used that to grease up our cocks and wacked away. It was crazy, but it felt good. I didn’t know that jacking off with somebody else would add to the pleasure. It was somehow a kick to watch Taylor move his fist up and down that long piece of hard meat. I also didn’t know Taylor had such a filthy mouth, which also added to the forbidden thrill.
He’d say things like, “Yeah, jack that nice cock of yours,” and, “Come on Ryan, let me see that cum flow,” and, “That’s it; beat it hard."
When I came I shot my cum all over the damn place. Taylor came right afer me, and made as big a mess as I did.
Well, that was that Friday, and a one-time thing, right?
No, the next Friday he was back, and there was a repeat performance, a difference being he didn’t have to say anything to convince me to do it. We’d made a mess the first time what with the grease and the cum spurting everywhere, so this time before I got naked I got some proper lubricant and a couple of rags.
There was also another even bigger difference.
This time Taylor came first, and then reached over and started feeling my cock. I guess I was shocked in some mild way, but the whole situation was so crazy that nothing seemed that shocking, and again, I felt great. So I let him have at it.
He’d jack me and say, “Man, you’ve got a nice cock,” and, “I like the way your cock feels,” and, “Yeah, let me bring you off; I want to make that cum spurt.”
If there was precum, which there usually was, he’d smear it all over my cockhead with his thumb. And when I came he’d squeeze my cock and make the cum ooze out and down my cock and smear it all up and down, coating my cock with it. And sometimes he’s catch his own cum in his hand and use that to jack me off.
As you can tell, I’m not just talking about the second Friday night. This was Friday night after Friday night, week after week. It had quickly become our Friday routine. A once-a-week jack-off-orgy.
Another innovation he came up with after a couple of months is one night he rolled his chair around so he was right in front of me and began rubbing the heads of our cocks together. Again, who knew? I almost came right then. And sometimes he’d put them side by side, his cock pointing at my balls, and wrap his big hand around and jack them both at the same time. I mean Wow! I never touched his cock, never wanted to, but if he wanted to feel mine, welcome to it.
This went on for somewhere around eight months, and then there were a couple of missed Fridays, and then no more. I didn’t know what had happened, if he had gotten bored or moved on to new things or what, but I have to say I really missed our sessions. Jacking off alone didn’t seem nearly as satisfying as it had in the past, but I didn’t feel I could say anything about it when I saw him.
It was always just, “Hi, how’s it going?” or, “What’s new?”
I still like being around him a lot, and maybe someday I’ll just say, “Hey, Taylor, how about us jacking off together again?”
I might even offer to jack his cock, if I think it might help. Who knows?
Part two: Mason's story
When I was fifteen I realized that I was gay, but didn’t know what to do about it. So now here I was almost seventeen and I had never had sexual contact with anyone. I would have liked to talk to someone, but I didn’t know who that could be. I have an older brother, but Ryan’s nine years older than me and we’ve never talked about anything serious or done anything together. I think when I was born he was resentful, but I don’t know that for a fact since, as I said, we never discuss things.
My older sister is married to a nice guy named Taylor. He isn’t handsome or anything, but I think he’s sexy. He has a really dark-brown beard that makes him look sort of mysterious. Or at least that’s what I think. I think he’s about twenty-nine, which makes him even older than my brother, but I always thought I could talk to him easier, but I didn’t know how to even approach him.
Months before, he’d started coming over on Fridays to spend time with Ryan. They’d go into Ryan’s “private space” that mere mortals weren’t allowed to enter and do I don’t know what. I know they watched TV, and I guess every game broadcast, and they drank beer, but jeeze, every Friday? Boring. Well, that’s what I thought. One night when he was leaving Taylor said he wanted to talk to me about something serious and secretive, and could I come over to his house at seven the next Friday.
I knew the front door was kept locked but the back one was always open when someone was at home, so I rode my bike around back, leaned it against the barbecue and went in.
The house was quiet so I called out, “Taylor?”
He yelled back, “In here, the bedroom.”
I went down the hall and into the room. He was propped up in the bed looking at a magazine. I had seen him shirtless before and knew his chest and stomach were covered with hair, as were the lower part of his arms, but he didn’t have hair on his shoulders or back, which I liked. He was wearing khakis and white socks.
He said, “Jump up here,” and patted the bed beside him.
I kicked off my shoes and climbed onto the bed. He opened a drawer in the night table and dropped the mag in, closing the drawer.
He looked at me. “Well, how are you?”
I grinned. “Fine.”
He continued looking in my eyes for a few more long seconds, then said, “There’s something serious I want to talk to you about.
