He is a lot older than me. I know him from a social group and choir that we both go to. This is word-for-word true. I have absolutely no regrets.
I am alone by choice, and have been for about eight years now. He is/was married until last year when his wife suddenly died. He is a private person, and did not like talking about his loss, but one night, I managed to get him to talk. He had driven me home and I had made us both a drink. I asked him how he was feeling and he told me that he was coming to terms with it, but he told me that the thing he couldn't adjust to was a lifetime on his own. (Yes, he IS old enough for that to be a real possibility)
He also said that he missed the 'physical side' of his relationship. I muttered something about he could take care of himself, but he just smiled back and I knew I had messed up. It reminded me of my ex. He was physically incapable of orgasm unless he was with someone, and sometimes that gave him wet dreams that were so powerful they actually hurt him.
After a few moments, I asked him, what, given no holds barred, would he like to do. He just said that he would really like a woman to be with him while he 'took care' of himself. A little more chatting and I learned that all he wanted was someone to lie on the bed with him and hold his hand and maybe talk to him. In a moment, I had decided I would do that for him.
I led him into my bedroom and turned the lights down low and told him to get ready. A few minutes later, I slipped my t shirt and jeans off and lay on the bed beside him and felt the bed begin to move as he began to masturbate.
I held his free hand against my tummy and began to talk to him. Not 'dirty', just sexilly. And then I noticed that I was getting turned on, VERY turned on. Here was a man old enough to be my dad, and I was getting wet and my clit was on fire! I turned onto my back and said 'Hmmmm. This is SO sexy' And I took his hand and put it between my legs over my panties.
Well, in a trice I had decided I wanted more. I guided his hand under the elastic and between my thighs. I even had to encourage him to put his finger inside me but when he did, I almost came instantly. As he fingered me, I wrapped my hand around his cock and finished him off. I felt every pulse of his orgasm and that lovely smell of freshly ejaculated sperm was enough to send me over.
We lay there in each other's arms for a while before slipping under the covers.
We slept like that all night. In the morning, we both found something else to do with each other.
So, I have masturbated a much MUCH older man (and more) and it was like nothing else on earth. FAR more satisfying and really REALLY good!
Maybe the future looks brighter, for both of us.