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First Time at Fifty

Posted by: Age: 50 Posted on: 0 comments
1 likes 690 views Category: Masturbation Male-Male Tags:

I finally had my first Male, Male encounter and here is my story.


I'm a happily married professional of 50 living in the South Eastern US. For the last several years I've fantasized about what it might be like to be with another male simply for the purpose of a mutual jack off. I placed an ad on an Internet site looking for a jack off buddy and was pleased to have a number of replies. I advertised for someone in Boston because I was going to travel there in a month and wanted to line things up if I could.

After corresponding with the ones who replied, I settled on a guy who was 48, married, had three kids, and lived in Kansas City. He was going to be in Boston the same week I was going to be there.

We met in my hotel lounge and spent a good hour relaxing and having some good conversation about our lives and, eventually, why we were pursuing this male-male experience. Like me he had never done this before and he had the same curiosity.

We eventually agreed to go to my room. Although I was quite nervous, I could feel the beginnings of a hard-on as we got into the elevator for the ride up to my floor. In the room we nervously made some small talk and I finally said, 'well, let's do this.' I reached over to him and felt his already hardening shaft through his pants as he began feeling mine. In minutes we were both rock hard and I unzipped my pants and let my naked hard dick spring upwards. He did the same, only he took his pants all the way off. I then did that too.

We stood facing each other and for the first time in my life I found myself looking at another man naked from the waist down with a big throbbing hard-on. Our hands automatically reached out for each others hard dick and we stood feeling each others massive hard-ons.

I found it interesting and extremely erotic to be holding this powerful, rock hard, throbbing, large big dick in my hand. I've been jacking myself off for many years and I certainly know what my own feels like, but feeling someone else's was a new experience for me.

We stroked each other simultaneously for a while, but agreed it would be better to do each other in turn. He sat on the side of the hotel bed and I stood more or less between his legs. He had his legs separated and his big balls swayed to and fro as I started jacking him off. He really got into it, closing his eyes and moaning as I jacked his big hard dick. I loved the feel of his dick in my hand. It was so hard and firm, yet soft on the outside. He tensed up and said he was going to cum. I gave him some more sturdy strokes and he spewed ropes of cum all over his stomach as he was leaning back.

He wiped the cum off his stomach and said 'now it's your turn.' I assumed the same position he was in and he started jacking me off. It felt so good to have someone else doing the work for a change. He made nice comments about my dick as he stroked me up and down, and finally I gave in and shot my load all over myself.

I cleaned up and we put our pants back on and I walked him back down to the lobby door where we said good-bye. In hindsight, if I could find someone like this again I would let a guy jack me off every night and I'd do the same for him. Besides feeling great, it was interesting to look at and feel another mans supreme hard-on. I haven't done this since that encounter but I think about doing it again all the time.



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