I've been masturbating on the average of once a day for the past 30 years. I've been divorced for about 5 years and since my divorce I have enjoyed the freedom of being able to do it almost anytime I want.
I have a friend from work who is married and we often have very frank discussions. She tells me about her sex life and I tell her about mine, although mine is usually about my masturbation sessions. When she can she calls me on the phone and she always asks me if she's interrupting anything. Sometimes when she calls I'll be watching a porno movie and jacking-off. If that happens, I tell her and she usually just chats with me as I do it. I get turned on by talking to her as I do it. She has never joined me but doesn't seem to mind me doing it.
A couple of months ago, she told me she was going to be in my neighborhood and was going to drop in. On that night, I got home from work and popped a movie in and started jacking off when she called from her car to tell me she was coming over. I told her what I was doing and she said that I had to finish before she got there. The pressure of having to hurry made it so that I couldn't cum and the next thing I hear the doorbell ring. I turned off the movie and pulled on my shorts and answered the door. I was obviously hard and when she came in, she looked down and said 'didn't you finish?' I told her no and asked if she would mind if I finished. She didn't want to but I told her that I was desperate so she let me jack off while she stayed in the other room. Before I came, I asked her to come in and she did and watched as I finished, shooting cum all over my chest and some on my face and in my hair. She laughed, while I cleaned up and we chatted for a while.
About two weeks later, she called again to say she was in the neighborhood and was coming over. I was again in the middle of doing it and told her. She said that I had to finish. We talked on the phone for a while and kept doing it until she pulled into my driveway. I was still jacking off and told her so. As she came up the walk way, I didn't bother turning off the movie or putting shorts on, and instead met her at the door slowly pumping my hard on and invited her in. She came in and sat down and watched the movie with me while I jacked off. I really enjoyed her being there and took my time. I had cum earlier in the day so it took me a long time anyway. When I finally came, it just squirted a little and I cleaned up. It was such a huge turn-on.
She told a friend about this and I suggested that she bring her friend over some day to watch. Her friend is interested and I'm hoping to do that soon.