Older Men Experiment II

After my first encounter with another man as an adult, I went about 9 months before having the urge again. I answered another CL ad, and met a younger man, who brought video of his wife fucking. We sat next to each other and talked and masturbated. I think he wanted to do more, but he didn't ask. We had a good time, just masturbating ourselves. When we were finished, he said thanks and left.

I met two other men over the next few months, once each time. Pretty straightforward jacking to porn, no touching; just stroke and cum.

I then answered a CL ad, and met a guy at his work. He had a portable building outside as his office/bunkhouse, as he commuted from out of town. His employees assumed it was a business meeting, as I was dressed for one.

Inside, he had a TV with a video already up. It was a homemade video of a woman going down on another woman. Her ass and pussy were clearly visible, as it was taken from behind her. He said that is his wife. They were swingers, and he said she loves pussy.

We undressed waist down and sat in adjacent chairs. I was hard quickly as he described his wife's adventures with women, and he got to fuck her friends as well.

We stroked ourselves, and he asked if I had stroked another man. Yes, one, I said. He was so hard, and said he gets excited having fun with a new man. He asked to touch my penis, and I moved my hand away. He reached over and stroked it some, and I got the nerve to start stroking his cock. Like the first time, it was surreal. I was actually masturbating another man, which 40 years ago I thought I would never do.

We did this a few minutes, watching his wife with this other woman. He then moved down in front of me, placing a towel on the carpet. He knelt between my legs and started jacking me and caressing my balls. He said, "Watch my wife," and things like, "would you like to fuck her?" I was so hard by now. His technique was fantastic.  I asked if his wife likes anal. He said she loves it.  "Keep looking at her ass, imagine you're fucking her ass."  He changed his grip on my penis to simulate me entering her sphincter. He spat on my cock to lubricate it, and used both hand to stroke me.

It took about a minute of that, watching her ass bobbing on the screen and his amazing stroking of my cock, and I erupted. I actually shot the first pulse about six inches in the air, and it fell back onto his hand. He gently stroked me to several pulses of cum. It was unbelievably intense and felt so good. Almost a full body orgasm.

After I was done, he stayed knelt in front of me. I was spent, and said if he could wait a couple of minutes I would try to finish him. He was so worked up at making a newbie cum, he kept his left hand on my cock, and reached down (my cum still on his hand) and stroked himself. He came in about 30 seconds, grunting and moaning, shooting his load on the towel below.

I ended up meeting him three more times, and then we lost touch.

After that, I went over a year before meeting the next man.