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alanj Amateur Jackinchatter

425 posts since 2014-04-18
77 year old homosexual male from indiana
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Many years ago I was the younger guy getting a blow job from an older married bisexual. Would love to get together with a much younger guy.
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Would love to hear more of that story plus some of your other adventures and fantasies.
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reading all these got me hard and dripping first thing in the morning. need an older man to cum take care of this...
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getnoff Professional Jackinchatter

1241 posts since 2006-12-20
64 year old
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I've had some great fun introducing younger guys to the pleasure of helping hands and willing mouths. There were several 19/22 is college aged guys away from home exploring, and a number of young men in their 20s who were experimenting. I'm always willing to be that older guy/mentor/helper.

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Fappy_Go_Fucky Amateur Jackinchatter

486 posts since 2013-09-30
59 year old curious male from Fort Collins, Colorado
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If I'm going to jump the fence and play with another man, I prefer older guys, I am one after all. But I've stroked with a couple of younger guys and I can see where it might be intimidating, but fortunately, the two that come to mind weren't.

The most memorable was in a video booth at the local adult bookstore. He didn't look 18 yet but he had to be. They're pretty rigorous there about the age posted on the door and if you look underage, they check. I saw them check him. I was about 45 at the time.

There were only the two of us in the back and when I chose my favorite booth and started to close the door, he slipped his hand in and held it so I knew he wanted to join me. He was wearing sandals and basketball shorts and as soon as the door was closed, while I was selecting a movie, he just stepped out of his shorts.

When I turned around, there he was, Nirvana t-shirt, sandals, ball cap with the logo of the local university, and a fairly small erection. I'm not huge by any means but he was maybe three inches or a little more, fairly thin, with a patch of dark pubic hair that made him look smaller.

I took mine out and we stood side-by-side watching a charming young woman being gangbanged on the tv screen. At one point, I reached over to touch his and as soon as my fingers touched that little cock, and it was hard as wood, he said, "Daddy, no!" and came immediately. Four or five long, thick streams across the floor. I'd never, ever had anyone call me that before so it struck me as funny. I was chuckling when I said, "Sorry," and he glared at me, but he went right on stroking, without losing his hard-on.

I kept my hands to myself and so did he. He was watching me while he slammed his two fingers and a thumb up and down his shaft. I thought he was going to hurt himself. He asked me to let him know when I was ready. When I was, I started to say but I think I only got as far as, "Uh, I . . . ". He bowed at the waist and took just the tip in his mouth and I filled it. When he leaned up and started to reach for his shorts, which were hung on the ashtray, I saw that he had shot another heavy load on the floor between his feet while I was cumming in his mouth.

He kissed me on the cheek, said, "Thanks," and slipped out the door, holding his shorts. I heard another door close so he must have gone from my booth to another because when I stepped out a few seconds later, he was nowhere to be seen.

Only ever saw him twice after that. Once more at the arcade, where we had another memorable encounter that involved very little masturbation and more of the other. And once at a movie, where he was walking in with his arm around a very nice looking young woman. So maybe, like me, he plays both sides of the fence.

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ladude25 Amateur Jackinchatter

334 posts since 2016-01-31
male from Pensacola FL
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45 m looking to jack with ynger
jeff saxon
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ChefYaz Amateur Jackinchatter

398 posts since 2017-04-14
bisexual male from Louisiana
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A few years ago, when Craigslist still had personal ads and the wife was out of town. I posted for a young guy that was thinking about "experimenting" with another guy.
One fellow responded.
When he showed up on my porch, he told me he was 20 but looked every bit of 16.
After about 20 minutes of chatting, (and coaxing) he told me about getting teased for getting hard in the shower after gym class.
During our conversation, I noted that he had his hands over his (obvious) erection in his jeans and had been looking at my crotch (I had on shorts that are basically boxers with pockets and I made no attempt to hide my erection).
When we came to "that" pause at the end of the conversation.
We looked at each other like "now what".
I then gestured toward his hands still over his crotch and said "don't be embarrassed, be proud....I'll show you mine if you show me yours"
We spent the next 30 or so minutes playing with each others cocks!
At the end, I shot my usual 2 quick squirts and he unloaded what seemed like a 1/2 gallon of cum!
Never heard from him again....I ran the same ad a few more times, only other response was a creepy 40 something guy that wanted me to fuck his ass....I declined.
I like to play with my cock!
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