Shame I have to do this.  We've been seeing each other 1-2 times a month for about 7 months.  Good sex, conversation, and no strings.  However, she got herself into a small bind.  I gave her cash for it and she blew it.  Still in a bind and begging me to see her.  I forgave her the first time because I didn't have time to see her so I gave her cash anyway as a gift.  Second time, I could only meet for a quick coffee and BJ but still gave her full allowance.  And she fucked up again.

Fool me once. Shame on you
Fool me twice, shame on me...

As much as we don't want this to be primarily transactional, the underlying premise is quid pro quo. Our SB's expect us to be reliable, consistent, trustworthy, and "professional" in the sense that we stay organized, communicate well, and deliver on our commitments.  

 
And SD's have the same expectations from SB's, though we generally grant more grace for under-performers in their less-than-professional business-person behavior.  

 
However, at some point we have to make a judgement call when she's not living up to our expectations and/or needs. Perhaps the best way to measure this is to look at the opportunity costs of status quo vs dropping and replacing her.  

 
You gave her cash to help her three times. She used your cash for other purposes. That means either she never really had a problem, or she was taking advantage of your generosity. Both are violations of your trust. If you cannot trust her, how can you stay in an arrangement with her?  

 
Finally, what could you have done with all that wasted cash?  I suggest that you could have had some pretty amazing BCD time with a new SB.  

 
You made the right decision.

 
Life is good

 
The Cat