All the time when I was younger. When I was living on the street I'd get picked up a lot and sometimes paid in cash ($100-200) or in exchange to get high or even for just a place to sleep/take a shower. I was horny and homeless so I didn't really give a fuck how much $$$ they'd offer.
There was the guy who gave me and a friend a ride to the park and paid us some money to watch us tickle each other's feet on the way. Dropped me off and i got to cruising the park, where I promptly got spit roasted in the bushes and fucked raw by a couple strangers while my buddy kept lookout.
The closeted religious guy who was a repeat customer who just paid to cuddle and massage but nothing more.
The hot rich muscled lawyer daddy. His late 80s sugar daddy partner couldn't get it up anymore but still enjoyed watching him fuck me, as he lay in bed next to us.
Guy who developed feelings for me apparently after a few times. He was really into sniffing my pits.
The OCD clean guy, who made me strip down first step into his house, and put everything in a big plastic bag, step into some clean slippers and proceed straight to the shower without touching anything before he'd fuck me.
Lots more.