I talk to my brother and he told me a x girl friend/wink " (a working girl ) needed to borrow some money for rent because a gentleman stole it and now she's going to be homeless .  
 You know, last month she needed a car payment made by him !  
 What do I say to him ? Dumb ass""""""" lol or just laugh at him every time  
 WHAT DO YOU GUYS THINK SHE WILL SAY next time .  
Has this ever happen to anyone here?

I'm seriously turned off when a girl is so entirely dependent on a guy so constantly like that. Regardless of how good looking she thinks she is, it's a major turn off that is enough to kill my erection.  

Imagine my surprise when I discovered there really wasn't any fabulously wealthy Nigerian prince who needed my help.

Yes, I have helped out a few. It was purely to help a needy friend and nothing was expected in return. Would I do it again, yes; I would.

The sleazy underbelly of NYC was back in the late 80's when I was 18 years old and decided that it was time to lose my virginity.  I was a nerdy kid from Queens who never went to "the City" but was now commuting to college in manhattan every day.  Awkward, I could never connect with the girls as anything other than a "friend" so where did you look for a hooker back then?  42nd Street!!!  The Deuce!
After playing around with peep shows and porn theaters for a while I flat out asked a shady character where to find a whore.  Seeing my wide eyed innocence he told me that for $40 I could "go inside that door right there" around the corner and "my girl will take care of you".  So I handed him the cash, went in the doorway and found myself confronted by an apartment building doorman.  That guy asked me "can I help you?" And when I stammered out my embarrassed query as to where the "girl" was, he shook his head and told me, "you've been had kid".  Going back outside I looked for the dude, but never saw him again.

In trade....no girl has lost sight of the help I provided when needed..Help for someone that has become a friend is not an awful thing to do..

That's why people who have been around will tell each other never to lend money, but just give it to her.. As in don't expect to see it back once it leaves your hand. If you see it back, great...

but he's going down a road that any clear thinking person would not go down.   Now if he's given her a loan with a hard date set and she repay's him,  sure . I don't get from your story it's a loan he's helping her pay her bills. Just because their dating doesn't means he's obligated to pay her bills.   She will continue to  rely on him  until he put's a stop to it.

The session was over and I ducked into the bathroom.  In less than a minute she'd taken several hundred  bucks from my wallet.  Lesson learned, from then on my wallet and passport were locked in the safe.
I did once advance a gal a few hundred to get her car out of impound.  It was for a session I'd already booked.  She was good for it.

True enough. A provider once asked if I could give her some money, as she hadn't been working lately. I told her I could give her an advance toward our next session, but I couldn't just give her money outright.  

Maybe I should step up a notch or two. lol

Thanks to the wise members here...  I'm willing to book an appointment with a gal if I would have anyway.  I'm not in the gift business.