I'll start

I used to work as a rent boy in college. I had one regular who was in his 80s and he likes to sit in a chair and would stuff ten crumpled up hundred dollar bills in my mouth one at a time while I masturbated while saying "I'm a worthless faggot whore" until I came. It was an easy $1000 a session. Some months I would get three sessions.

He showed me some photos of himself at my age and we looked almost exactly the same so I don't know what issues he was working through but I got a nice wank and 1000 bucks. He was rich as fuck and would send a driver to pick me up and drop me off and I wasn't allowed to talk to the driver at all. The driver used to try to get me to engage in conversation but I didn't want to risk losing such an easy gig so I never said a word to him.