The DS and I have passed a new, inevitable line in a stripper customer relationship. No, she doesn't want anal sex. But she has for the first time asked me for extra money.
We are smoking in the hot box. She says that she needs to talk to me about something. Whatever she has to say is clearly hard for her because it takes a while for her to tell me. From the way she approached the subject and how hesitant she was, I really thought it was going to be something serious. Turns out she says that she has a medical issue and doesn't have insurance to cover the cost. She wants to know if we can work something out so I could help her. She mentions that maybe I could see her more often for a while.
The way she made this request was the nicest way that I can imagine a dancer making such a request. She acknowledged many of the things I was thinking. For example, she acknowledged that many strippers regularly try to guilt their regulars into paying them extra money, that such requests have never been a part of our relationship, and she was very hesitant to ask because she knows that I value a relationship with a minimum of stripped shit. I have told her many times that one of the most awesome things about her is that she doesn't act like a stripper (except for taking off her clothes and having sex with me for money). So because she knows this about me, she is hesitant to make such a typical stripper move. And she apologized for asking over and over. It really was a very humble way of asking for money. In her words and actions, there was none of the stripper entitlement that we see so often among dancers.
She described the background of her medical issue which made her cry. And it's not an std, so get your mind out of the gutter. This is my dream stripper that we are taking about here. Obviously I know that women use tears and sex to manipulate men, but if this was manipulation it really was amazingly masterful. I've never seen her cry before, and it didn't seem in the slightest to be an act.
If I had never been to tuscl, I don't know that it would've crossed my mind that she might be lying. She really came across as very genuine. Plus I do know her very well, and I'm a pretty good judge of character and truthfulness. And I think she really does have this medical issue. And summer has been very slow, so it makes sense that she might have trouble covering such an expense.
But I have been to tuscl, and I have heard all of your stories about strippers' manipulative schemes. Hell, while she's talking I swear I can hear some of you warning me -- its stripper shit John, they all do this, you know it can't be true, run John run, etc etc. Given everyone's collective experience, I am forced to admit that this could all be manipulation and lies to get me to pay her even more. I don't think it is a lie, but I am not so pathetic that I don't acknowledge that possibility.
My question is how do I respond. I'm going to do something for her. She's never asked before, and she's the most amazing dancer imaginable. But I don't want to become an ATM that dispenses cash upon demand. Here are my current thoughts.
First, I plan to make clear that while I'm helping out this time, I do greatly value the fact that she isn't always trying to get extra money out of me and I expect this to be an exception and not the rule. I pay her above market rates already, and while she is totally worth it, this can't become a regular thing.
Second, I thought I'd suggest no (or minimal) shopping for the next few months and I'll just give her the cash that I wound usually use buying her things. This won't meet her entire need but it'll be significant.
Third, I'd like to find a way to see her more often. Then I just pay our agreed upon rate for those dates. The problem is that it's hard for me to travel to her town to see her more. I considered a trip but we already have our standard once every two month trip coming up soon. So I'm not sure how to work this but I'm going to try to find a way to pay her more without it being a hand out.
Fourth, no I will not give anyone her contact info so you guys can help her out. That's a nice gesture if you thought of it but it ain't gonna happen.
Any other suggestions for how I should handle this?


And so it begins....
In my experience (not saying it will be yours) this is just the beginning of the requests for money. I held on to money pits for way too long at times.
The true test to see if she genuinely likes/cares for you is if you tell her "no" one day and she still wants to keep seeing you. Or do the texts, sex, OTC, dates, etc.end?