When, if ever, do you think the day will come when it's considered inoffensive (and complimentary if the $ amount is high) for a guy to offer P4P to any woman? Like asking someone if they are interested in selling their car, house, etc.
I suspect the answer is "never". Girls who are open to P4P can use a number of web sites to contact folks. So civvies who aren't open are always going to exist and won't take kindly to offers of money for a little somethin' somethin'.
Seriously, I suspect that even some girls open to P4P might take offense at contact through other channels. One thing to answer a web posting, another to just ask...
Not FS P4P, but I was once at a stripper's house when a couple of her friends came over. The stripper told me that one of them had one normal areola, darker than her skin, and one that was lighter. I offered $20 to see them and she showed them.
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Seriously, I suspect that even some girls open to P4P might take offense at contact through other channels. One thing to answer a web posting, another to just ask...