I'm 57 and I have been divorced for 15 years. I've been married twice and I'm not ever going there again! I'm content in my life but I get horny just like every other guy does. Other than getting laid occasionally by a life long lady friend most of my sex is with myself.
I have a neighbor two houses up the street who I've known since I moved into my house some 10 years ago. She is a widow of many years and she is in her late 60's. She is pleasant looking and very friendly. I cut her grass for her every week. We have had many discussions over the years and there is one thing I do like about her and that is she is a real straight shooter and doesn't mince words.
About a year ago we talked about sex. She told me she was wild and crazy in her youth and did many sexual things she shouldn't have done. She told me I was still not too old to go find a woman and have a relationship, but I told her I never wanted that again. She asked me what I did about sex. She knows about the occasional lady friend but she also knows that isn't a relationship and anyway, that's maybe only three times a year that I get laid. I told her frankly that I jacked off to keep myself from going crazy.
She said something like 'that would be interesting to watch.' I looked at her and told her if she wanted to watch me jack off I had no problems with that. I said 'in fact, if you want to watch right now I'll do it for you.'
She told me that would be OK with her. We went into her house because we had been sitting on her back porch. I found myself getting hard at the thought of this woman who I had known a long time was about to see my naked and hard jacking off.
She took a seat on the couch and I took my pants off in front of her. My dick was really hard. The anticipation of what was about to happen really had me 'up!'
'You have a nice dick,' she said. I walked into the kitchen and got some paper towels and walked back over and sat beside her on the couch and held my dick out so she could look at it really well, and I began to slowly jack off. She asked me many questions about how it felt. I was really excited. I asked her if she wanted to join me or at least take her clothes off but she said no to each of those questions. I didn't care, it felt incredibly good being watched by her.
When I was ready to cum I told her then I held the paper towel in front of and a bit under the end of my dick so she could see my cum squirting. She told me it was 'interesting' to watch me.
I told her I REALLY enjoyed doing that in front of her and I asked her if she didn't mind terribly, could I do it again sometime? She said she found it enjoyable to watch and, yes, I could do it again.
I now call her and ask her if I can come up and jack off and she always says OK unless she is going somewhere and then she simply gives me a time later in the day. I have done it many times now in front of her. She has never shown me any part of her body or participated. She just likes to watch me and that is OK with me.