It can happen... I had a SB in North California who was a former Iranian fashion model. At 32 she was still extraordinarily hot! She had a job in financial services (with a competitor to my company!), drove a BMW and had a few SD's on the side with real money ($1m+ balances). She insisted on seeing me at least once a month. Go figure.
I think she just really liked the idea of having sex for money.
My advice:
Approach with caution, and fuck her brains out as often as you can. But be careful of "innocent" little add-on requests...
"Oh Hun, can you please get me a new phone? Someone at work dropped mine and the screen is cracked. I need a phone so we can stay in contact!"
"He babe! I need $300 to get my hair for this weekend trip with you.... Pleeezzee! You want me to be beautiful, don't you?"
"Oh no! I'm going to lose my car 'cause I can't cover the payment this month. I won't be able to see you without a car, Babe."
Etc. It's always an emergency and always not her fault, and always has an angle that threatens her ability to see you.
The answer to all of these is a polite no. Not "maybe" or "we'll see". Those will be taken as "yes". If she continues these asks she's working you over for more than you want to commit to funding