This happened two weeks ago.
I was in a hotel lounge relaxing and a well dressed woman, aged about sixty, sat down beside me. We talked for about two hours. At one point she asked me if I was the typical male on the 'hunt' there in the hotel.
I laughed and said 'No, not really.' I had just ended a relationship and I wasn't about to get into another one. She said she wasn't on a hunt either, especially at her age. We both had a chuckle over that. I was feeling comfortable with her and I joked that all I needed to keep me company was...and I pointed to my hand. She laughed and I followed with 'and it doesn't talk back to me either!' She giggled and laughed at that.
She then said something like, 'me too, I know what you mean.' I was going to let that talk die there but she kept the talk up, like, 'I can do it whenever I want and sometimes I think it's better than the real thing.' Again, I agreed. Now I was guilty of adding to the fire by saying 'I like to watch women do that.' She smiled at me and said 'and I like to watch men do that too.'
I guess it was quite involuntary, but I started getting hard. I offered, 'I'll do it for you if you'll do it for me!' She told me then that sounded like a fun idea! She said that I seemed like a very nice guy and she thought she could trust me.
She wasn't bad for her age. She had a rather thin body and nice hooters. I asked where we should go? She said how about her house only a mile away. I followed her down there in my car groping my hard-on as I drove. I just let it show as I walked from her driveway to her front door. My pants were bulging!
Inside she wasted no time. She immediately bent over and put her hand against my pants and gripped me saying 'Looks like you are all ready to do it!' I just unzipped and dropped my pants and stepped out of them, then pulled my boxers down over my feet. She smiled and passionately took my dick in her hand and felt it and started stroking it. I said, 'wait a second, I'm watching you too!' She stood right in front of me and undressed. Her boobs hung and her once hairy pussy was thinning out, but all in all not too bad at all.
She said 'do you like it naughty?' and I said I did. She laid back against the arm of the couch and spread her legs wide and let me look at her pussy. I could tell it had been well used in her lifetime, but I still liked looking at it. I sat in front of her and spread my legs so she could have a good look at my balls and dick and I started jacking as she rubbed her clit and fingered her pussy. We made dirty filthy talk as we did this to help heighten the moment. She could really say some nasty stuff!
When I was ready I got up and stood beside her and I came all over her tits and big nipples. She loved it! She kept working her pussy and then she finally came too.
When I was leaving, she told me if I ever wanted to jack off for her again I knew where she lived. I haven't been back yet, but I think I'm about due for a big cum so I'll probably make a visit any day now!!