My recent SR (one month old) started hot and heavy with an SB asking for a really small PPM. So it progressed from once a week to twice a week and now she's pushing for 3X a week. I like her well enough, she's educated, employed, has a boyfriend so no drama. But this constant hinting for more and more is getting on my nerves. For example we had a bet about something which she won. The winner was supposed to choose an activity together. Instead she hinted she preferred the cash. Also when we go out she over-orders at restaurants and then doggie-bags. I fully understand they are in it for the cash but at the same time the sex is getting boring. Is it time to bail or have a frank discussion?

You said it yourself... the sex is getting boring and she is obviously starting to get on your nerves.  

On to the next one.

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Once the sex gets boring, time to move on.

I am surprised you even asked the question.

When the sex gets boring with an SB it's well past time to move on.

Not to mention that over-ordering shit won't fly with me for a second. I don't really mind being the guy fucking some college kid's GF because he can't or won't step up and treat her right, but I refuse to be "that guy" the one slobbering all over her, giving her gifts, money etc just so she can run home to him and share the food that I bought her.

I remember a friend of mine many years ago was raving about the "chemistry" he had with this hooker/SB he was seeing. She also happened to work for an agency who's owner was a friend of mine. One week he was raving about her yet again and told me he had "treated her" to a couple of grand so she could go visit her mother in Miami, and that he didn't mind even though it meant he wouldn't be able to see her that weekend. Little known to him, she was taking HIS money and taking her "real BF" to the beach that weekend, I never had the heart to tell him the truth. but I resolved to NEVER be "that guy"

GAGAMB HAS RULES??? LOL

You don't necessarily have to bail, but you do have to act to take back control.  

Personally, I don't care what she does with her money. And it is HERS, not yours, once you hand it over.  It took me a while to get my head screwed on about this. I used to get bent out of shape if she spent my cash on frivolous things, let alone another guy!  But remember that her inability to save or spend wisely is a primary driver of why she wants to suck your dick.  

Now the demands for more sessions per week and ordering extra food are a different issue.  You need to control this behavior by changing yours.  If she wants to go from 2x to 3x, don't be available.  In fact just be available once a week, or event once a month for a while.  If she asks for more time, tell her you're slammed at work, have family visiting from out of state, or whatever sounds good.  In fact, the more lame your excuse the faster she well see that you are deliberately walking back your interest.  

As for the meals, discover Denny's for a while, telling her you just want to grab a quick bite and get home (or to the hotel) to really focus your time on her fun! Better yet, grab a Taco Bell burrito before you meet and blow off the meal altogether.  

After a while, she will either bring her expectations back in line to the original arrangement or she will bail on you (and start banging an SD with a bigger wallet and less self-respect). Either way you win.  

-The Cat

No need to discuss, just go silent or tell her that you have money issues right now, if she still continues seeing you which I doubt then you got your renegotiation done without a discussion. Most probably if sex is not good then why burn the cash, just move on to the next one. That is what they do whenever they feel like.

Familiarity does breed contempt.

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SB's are just like any other kind of person. People treat you the way you train them to treat you, if you let it be known that it's ok to walk all over you, that is exactly how people will treat you.

I actually enjoy being generous, especially when things are going well for me, but I hate being used or taken advantage of, it takes away all the fun of giving.

Once the sex gets old or boring there's really hardly any point in trying to salvage the situation.  I've had several one time hookups with SBs that were simply not very good, so I moved on right away and did not see them again.  But if it starts out good and then deteriorates, cut your losses and move on.  

It's a two way street. You should bring new things on the table and explore together. Toys, threesomes sex workshops etc etc. it will add spice to sex.

As far as I am concerned "new pussy" is the best sex toy you can ever get.

I can't imagine having to "spice up" the sex in a paid relationship. The Sugar World is NOT real life. That's why we pay, so we don't have to work at spicing things up. We bring the sugar, she brings the spice. If I have to bring the spice, I damn sure am not going to bring the sugar as well.

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Yes you have a point. I just sharing what I get from my latest SB arrangement  by bringing the spice.  
Many SBs are novices and when she learns how to bring the spice the arrangement improves.
And for the same sugar I get much more--overnights and weekends and trips for nothing extra except of course the travel expense.