This is a follow-up to my previous story, "First Time Sucking Cock". If you have not read that story, I invite you to do so. The two stories do not really build on each other, this is just a continuation of my journey.
Once I had built up the nerve to finally acted on my curiosity, I found that I had enjoyed both experiences that first day. I had chatted with lots of different people, male and female, that found the thought of two guys enjoying each other in any sexual way very erotic.
There was one woman that I had been chatting with for some time. She was very hesitant to share any pictures of herself with me because she did not feel good in her skin. Her husband did not want to have sex with her any longer and she just sort of felt alone. We had actually been chatting for a while before I told her anything about my curiosity.
She and I had clicked and she just loved hearing about my other sexual adventures from my younger years. Not that there was a lot, but she liked to live vicariously through my stories. After a while she asked if she could see pictures of me and so I started sharing pictures with her, none with faces, but pretty much everything else.
I remember the first time I sent her a picture of my hard cock she told me that it was beautiful! That was the first time I had anyone tell me that my cock was beautiful. She told me how she had masturbated just looking at my cock. I felt pretty good about being able to turn her on like that.
As we continued chatting back and forth, I had sent her more pictures and a few videos of me jacking off. She told me that she loved them all. Then one day she asked me if i would consider going on camera and showing myself live to her. We were chatting on what used to be called Hangouts and there was a live video option for chatting.
It really did not take me long to decide, as I loved the idea of her watching me live. I set-up my laptop so that the integrated camera would capture only from about the waist on down. (After our first video chat I purchased a separate camera so I could control the view better.)
When I went on camera she kept telling me how much she loved watching me play with my cock. She started to talk dirty to me, like she was right there in the room with me and guiding my every move. She was very good at it and it made things an even bigger turn on.
Even though I was telling her how good it felt stroking myself for her, I think she was surprised when I came. I shot so much that the amount surprised me as well. I knew I liked making videos that I was going to share with my online friends and how much I came in those videos, but doing it live for her was even better.
One day I told her about an experience that I had as a teenager with another teenager and that seemed to really turn her on. I said that I had not done anything with another guy since that summer because soon after that I got into girls and never really thought about it.
I then told her how things had been changing with my wife over the last several years, with menopause and everything else in our lives, which meant we were having sex less and less often. I told her how much I still liked having sex with my wife and the pleasure we each got, it just was not as often as I would like.
I then talked about the many different people I had been chatting with on-line, including many guys that were in similar situations. I talked about how many of them expressed an interest to try things with another guy since they did not want to cheat with a woman and the emotional risks involved with that.
I said that the guys I talked to, only wanted sexual release and no emotional attachment. She seemed very interested in my conversations with other guys. I told her about one guy that I connected with on-line that did not live that far from me, but he was very hesitant to meet-up. He was very nervous to actually try something with another guy.
I told him about how my lady friend and I chatted on Hangouts and had gone on webcam and she watched me jacking off. We decided that doing that would be a good first step. He and I went on webcam that very day and watched each other jacking off and both enjoyed it.
When I told her about how I had gone on camera with this new on-line friend she was very interested. With the capabilities that Hangouts had at that time, I knew that we could actually have a three-way conversation. I suggested to her that I would ask the other guy if he would be interested in going on webcam and the two of us would jackoff for her. She was over the moon horny with that suggestion.
I contacted my male friend and he was all for it as well. I got back to her and we set it all up for a specific day and time. When the time came, we all logged in and he and I turned on our webcams. She still did not want to show herself on camera at this point.
She told us how cool it was to see two guys playing with their nice looking cocks live right in front of her. She said it was not quite as good as if we were in the same room with her, but still very hot. At that point she started to sort of give us jackoff instructions. It was fun taking orders from her and she was soon cheering us on and it became a game to see who would cum first for her.