jackslash-->"I get these requests all the time, and if I cut off every stripper who asked I would be pretty lonely. I don't blame them for asking. I usually tell them no. Some favs who I've been banging regularly I will lend a little cash (like $200). Do they ever repay me? No. But I don't mind sharing a little of the wealth with a young lady who pretends to like sucking my wizened old dick."
I think there's just a natural evolution in how you look at things. A guy who has never experienced this before, is going to have lotsoffun's reaction: "WTF! Fucking bitch! I'm crossing her off my list". A guy who has been clubbing for decades can handle it a bit more dispassionately, after the zillionth time he's been asking. Partly, it's not something new to him so doesn't kick off all kinds of defensive instincts. Partly, he doesn't feel nervous or uncomfortable about counterproposing something that meets HIS needs, too.
I've had an ATF with whom I sometimes floated her money before our OTC (I refuse to do Western Union and this was years ago before Venmo, so she actually gave me her checking account number and real name, and I'd just go to the bank and put cash in her account), and she always came through. On more than one occasion during OTC, I spent more cash than I expected on partying, drinking, dinner, so that I couldn't pay her all I owed her at the end of the night, I'd offer to take us to the ATM but she'd just wave her hand and tell me to put it in her account tomorrow. So, as I always say: you need to be smart enough to have rules, and wise enough to know when you should break them.