I knew a guy who would joke around about dumb guys who would believe the stripper likes them for real.

Then he did exactly that a month later, for weeks on end, and hundreds of dollars.

That is awesome.
I do have to wonder what is broken in me that makes me laugh at that stripper but hate on other predators who profit from the mental/emotional deficiencies of old people and their retirement funds

This must happen all the time. Between Oscar's comment above and that this story sounds like someone I used to know. Was she into Everquest or did the new generation of strippers carry on the tradition?

It's not really 'leading him on' though. The stripper's whole job is to act like they are interested in what the patrons have to say/aren't repulsed by them. If this guy was so deluded that he didn't realize that that fundamental transaction was taking place, you can't really put a shred of blame on the stripper; she was simply continuing to do her job without disabusing him of the fantasy.

The sad(?) thing is, while it varies from establishment to establishment, a slim majority of strippers are usually willing to just have sex for money outside of work if they are simply asked.

How do you slip a Harley into a thong?

The same thing happens with gay guys. I've mentioned gay doms but there are also a lot of bodybuilding gay guys that will bilk "donations" from "sponsors" ie older men they will flirt with.

A lot of the time they throw them a bone and just give them a facial every now and then but don't kiss or fuck the guy. I've heard stories of guys that got thousands of dollars of bodybuilding supplements, steroids, free gym memberships, thousands in gift cards to buy food. In return they do flexing sessions and allow their sponsors to just watch them. To be fair a lot of guys who are too old to get erections know what they're getting out of it but then some delude themselves and think it will turn into more. The idea that some of them never lived the life they wanted to because they were closeted and now were spending thousands on some boy toy who was just showing up once every couple of weeks to parade around their living room shirtless for a few minutes is just sad to me. They will never live out that dream, it's too late, the ship has sailed.

But on the bright side at least the world is becoming more equal opportunity when it comes to taking advantage of the desperate.

I would have given it a lot more stars. Duh.