I live in a condo and living this close together you get to know your neighbors very well. Next door to me lives a lady who is 60. She is a widow. Her husband died about 10 years ago. She isn't beautiful nor is she ugly. Not in the least. For 60 she looks pretty nice. She is trim for her age and she has an outgoing personality. She is lonely though and since I moved here three years ago we have become good friends.
In the last three years we found ourselves several times talking about sex. Needless to say, she isn't having any sex. It isn't that she couldn't probably find an older gentleman she likes, it is that she is just resolved to being single the rest of her life. She doesn't try and get out to meet any older men anywhere.
About a year ago in one of these conversations she mentioned that she missed sex on one hand, and on the other hand she didn't really miss sex. She said with sex comes commitments and all that and she just doesn't want to go there again, not at her age. I asked her what she did about sex those times she felt she missed it. She gave me a little smile and she said she takes care of that herself on rare occasions. We both then had a nice chuckle.
I admitted I took care of myself too, and she was surprised I needed to do that now and then. I have been in and out of a few relationships, but I don't have a regular sex partner, not at all. I said that I did it because not only does it feel good, but men really need to keep their pipes clean for health reasons. She said she undertood that. That was the end of that discussion that day.
Maybe a week later we were talking again and she asked me if I was keeping my pipes clean, then she laughed, making a joke about it. I told her that, in fact, I was overdue and it was something I needed to do soon. Being kind of a joker by nature, I quipped, 'Wanna watch?' then I laughed like I was kidding. I was bowled over when she said 'SURE!' I said 'Really??' She said 'sure, anytime!'
There was something about the sudden naughtiness of it that I found thrilling. I started getting hard immediately. I said 'Damn, lets do it then!'
I took a seat on her sofa and she took a seat beside me. She had a huge smile on her face. By now I had a terrific bulge in my pants. I placed my fingers around the long hard shape and said 'look what this is doing to me already!'
I unsnapped my pants and unzipped, lifted my butt a bit, then slipped my pants and underwear down and all the way to my ankles, then I leaned back, pulled my shirt up a bit, and I let her look at my fully hard dick. She was saying 'oh, my ...' and stuff like that. She said 'this will be interesting. I haven't watched a man jack off in years. My husband used to do it in front of me now and then but that was many years ago.'
It was wildly exciting for me as she leaned a little bit on my left shoulder while I felt my dick with my right hand, running my hand gently up and down my dick. I showed her a few things I do when I jack off that feel especially good to me. It was almost like I was giving someone a lesson talking about it as I did it. She watched intently.
I finally stopped talking and started seriously jacking off, not fast, but at a moderate speed I knew I could last with for a while. When I was ready to cum, I lifted my shirt and shot cum all over my stomach. She told me she loved watching me do that, and she said as old as she was she was getting a tingle 'you know where' as she watched. I told her I truly loved doing that with her and I asked her if we could do it again sometime. She smiled and said 'certainly!'
OK, to cut this short, she is a regular masturbation partner with me now. We get togther about twice a week. She likes it because we are friends, not lovers, and there is no commitment. Sometimes she jacks me off and other times she watches me jack off. It took several months but she now gets naked and allows me to watch her masturbate too. For her age, she still looks good and I get quite hard seeing her naked. Our little relationship is very, very fun and I'm enjoying it tremendously. Thanks for listening!