customer or friend?

I would give her a small cash gift, how much will be based on your past experience with her.

The problem is not what what you do for her but what you two go through. She's not your friend. She may think of you as a good buddy, a nice samaritan who is really thoughtful, but has she ever taken the time, to just...hang out? To just talk with you, whether it be about nothing or something but the something never involving favors? Has she offered to hang out with you with no strings attached? Doubt it by the way you explain things. She's not truly your friend but she may be appreciatve of what you do. Bring cash either way, but don't mention it unless she asks. She's not your friend she probably expects cash and your just the good samaritan pl. Otherwise insead of sex, she'd take you out to eat. Much more fun, helps save you money and she gets to be friendly or at least show apperciation without getting smelly and sweaty from your wringly ol' thing.

I resemble that! She and i have been to dinner 3 times - once she offered to pay, but I said no. One night we got drunk on margaritas in a restaurant bar and she has poured her heart out to me a dozen times. I've done the same with her regarding my burden of being the caretaker for my wife with Alzheimers'. But 1/2 the time I feel she's bullshitting me but towards what end, I don't know. I live comfortably, but don't have deep pockets.

Anybody else notice he said billionaire, as in B, not M.

She told me his name and it meant nothing to me. He bought her a condo ( I'm guessing $150,000. She's wearing a Rolex & showed me pictures of their trips from the Northeast to Vegas, Montreal, Bermuda, California, and other spots. She's clearly well read, great vocabulary, the type of woman you could be comfortable taking to the Ritz. But something just ain't right. Her Facebook page is filled with jive talking brothers, tattooed friends, ( she has none), and references to a drug culture. She has told me about once getting over her head with coke, but learning a lesson from it. She's either a once in a lifetime find or an anchor which could drag me down.
There's one of her coworkers who I've been seeing OTC for 3 years and has started taking me for granted. This chick took M aside, said stay away from me or else. She told her to fuck off and I'd see whoever I wanted to. Why didn't I have these choices years ago when I could handle them?

My simple philosophy is if she is worth it then pay her.
Let her either say no this one is on me or try to arrange a a cheaper follow up experience.

As a general rule in life (not just when dealing with strippers) loaning money or helping someone out should always be written off as a loss. I have helped too many people move and never seen any reciprocity and never expect it either. If you loaned you guy buddy some money you wouldnt expect sex with him for repayment and you wouldnt rush to stop dealing with him until he repaid either, but you would probably not lend them something so quickly next time.

"If you loaned you guy buddy some money you wouldnt expect sex with him for repayment"

speak for yourselef.

"Several weeks ago she returned to work, told mmme she had been with a married billionaire whoo brought her on business trips in a private jet."

Sure, she did.

That was my first reaction, too. But I've seen the condo she says he bought her, I've seen the Rolex (maybe its a knockoff) and I've seen photos of their trips, including one with his jet in it. Is she bullshitting me? If so, I think she's fooling herself, too. She has been consistent with her stories and goes into great detail concerning which golf courses he played, which hotels they stayed in, etc. On a couple of occasions her mothers been there cheering her on. The mother is 40 years old and is a piece of work. Today she told me that when her daughter was born she was 16 and didn't know who the father was so she just picked one of the many guys it could have been. Sweet!

I don't know why you feel obligated to give this whore a dime. Strippers are masters of hard luck stories, and yes they can have an routine that goes to some lengths about. Every time they start one of their hard luck stories with me it makes me less inclined to feel any sympathy for them.

Don't give her a dime, and just tell her you don't want to her about it anymore. Then if she calls you a "jerk" say "thanks!"

You're probably right, but I look at her long legs, her sweet ass, and those pursed lips, all I can picture is my cum dripping from her lips. Totally irrational but stranger things have happened. The next week or two will help me decide if she's the whore you describe or the high end call girl she describes.

She's playing you. She makes you feel sorry for her and then gets money and other help from you without giving you sex. Classic.

I'm also in my 60's and my ATF is in her 20's. Sometimes she plays the sympathy card, and I fall for it. I give her extra money or help her out. But of course she's fucking young guys for free and spending my money on them.

It's OK, I think, to let yourself be played a little bit. It helps us old guys to indulge in the fantasy that a beautiful young girl loves us. But when she asks for a $5000 loan or a BMW or money for a start-up business or a condo--then it's time embrace your inner cynic and realize she's basically a whore.

"Should I plan on paying her? " One word "YES".

a million doesn't go very far anymore...

I think all the clues are already there--you just need to connect the dots. It looks like there may have been some "arrangement" with the high roller (B sounds better than M), but he may have had the same misconceptions that you may be suffering from. She "used" to have problems with cocaine? How about still does? The falling out was probably that high roller thought he was getting the hot, refined high-end escort, but in time he found out she was really a junkie who acted like a junkie: lied, stole, completely unreliable, self-centered, irrational. Not a good fit for a jet-setting crowd.

The only reason a beautiful woman with no tats hangs out (evidenced by FB) with the ghetto crowd is because she is really a junkie. It is hard to believe she just simply likes the rap lifestyle or the music or the posse. She is getting her habit fed. Now, for you, if you want the strung-out drama of a desperate junkie (which will surely come as the rising sun tomorrow), you can follow-through. But if you think that she has turned the corner and you will be getting that sophisticated hottie that all the other Forbes 500 guys would clamor for, I say you're wrong. All too often, we know deep down that we aren't getting the sleek Lamborghini but will wind up with the broken-down Corolla that is always in the shop. And we do it anyway. Either way you are going to be paying. Not all girls can be like our Carolynne--sleek, sultry, saucy, stunning, and having a raging libido.

She should have saved the $$$$$$$$$$ that the sugar daddy gave her or made sure she stayed with him.

She id definately broken and will likely be just like her mother in a few years. Get it while you can but don't be her white knight or she will become an albatross.

being an albatross is good work if you can get it.

If she is a junkie, then you are a resource - pure and simple. You are a friend if you are driving her to rehab.

That's kind of the exchange, isn't it? Money for sex and company. You can only delude yourself for so long that a young, attractive woman would want to hang out with us geezers because she LIKES us. It's the arrangement you sign up for, getting involved with women like that in the first place and we certainly can't fault them for fucking whomever they want for whatever price they choose (free or otherwise). If an exchange of money is involved with a stripper then you are a customer, but I suppose that if we didn't want to be we'd just start hanging out with women our own age ;)