This is mainly for the ladies, but gents, feel free to chime in.
Where is the point where a generous, polite, sensuous older gentleman becomes an object of pity or jokes? I would like to think I'm not there yet, but at some point it has to happen, I think. I hope to have the sense to bail out in time.
My ATF had a gentleman client whom she was in love with. She could have had almost any man she wanted and I know she had multiple marriage proposals from well to do, handsome men including one Congressman and a CEO of a Fortune 500 company. But she turned them down to be his mistress/girlfriend. He was 78.
I am one of the old timers you speak of. Of all of the ladys I have been with I never felt like I was a pity fuck. Each and every one I have been with treated me like a prince. One called me grandpa behind my back but hell I am a grandpa. I hope they all remember me fondly as the old guy that was a joy to be with. When I die I hope some show up for my burial. My children kid me about my hobby but know the smile on my face is the result.
I think it is easier for children to know your happy with no strings attached then to accept someone who might be a replacement for their Mom. So as long as by your activities your still happy, physically and mentally able to perform. There should be no pity involved just gladness.
I was a provider to wonderful man similar to you - we had a very large age difference. He passed away at 82 though we had ten years together (though not in a true LTR fashion). We became very close and their never was the "pity" aspect of this. His kids and relatives knew of his "hobby" and we're glad he was happy. It is all in the attitude!
From talking with providers and these boards I don"t think for mature ladies there is an age. The ladies I have talked with are proud of their older clients for the most part. I think due to the nature of this business most of us would tend to drop out before we became objects of pity or jokes.
the gal whom you are paying to make you feel like you're still a 25 year old stud.
As for the people who see us together and cluck their tongues, fuck 'em.
As Groucho Marx once said: "You're only as old as the woman you feel." (And he knew too.)
She was in her early 40's and thought it was pretty great that they were still sexually active. One of them used a vacuum pump to get it up, but she said after that, he was good to go.
Fortunately, I think women are far more accepting of men's less than perfect appearance than we are of theirs.
your right in women it is a totally different then for a man. Men need the visual stimulation and the blood flow to the penis and we are good to go. If we happen to be mentally into it good but it is not needed as long as the stimulation keeps up. From the shows I have seen women need very little stimulation visually to start the blood flowing to the area, some don't even realize they are reacting even though instrumentation shows they are reacting. They have to be mentally into it so they need to mentally want it. So I guess they have developed more ability to look for the good in anyone to get mentally ready.
Fortunately, I think women are far more accepting of men's less than perfect appearance than we are of theirs.
"Where is the point where a generous, polite, sensuous older gentleman becomes an object of pity or jokes?"
To whom! There will always be someone to make remarks about us! The trick is to find someone whom you feel truly likes your company. I was reading an article a while back that talked about how a significant number of younger Japanese women like older, heavier, balder white men. Go figure, heh!?!
I guess as long as we don't show up in our depends, we're probably just fine! 
I absolutely adore older men but I agree leave the depends at home. They are a bit of a mood killer.
Got it. Great advice! Thanks for the feedback.