I'm surprised you haven't already sent him packing. The situation is probably different for each client, but when it would appear that the time to cut ties is when you're not comfortable with him anymore, and the money just isn't worth it. I told my regular that if she ever got tired of me, just come out and say so. Luckily for me, it hasn't happened yet.

In my business, I have a client who receives 50% off of his purchases.  I do that for a lot of reasons, but mostly because he brings a lot to the table for me too.  Even with the discount, I'm still making money from him, just not as much as my normal prices would bring.  He has been a long time customer and someone I can count on to make purchases frequently.  He is a respected member of my particular business commodity, and he makes recommendations often which results in even more business for me.

I've had others tell me he is just using me and that he is sometimes demanding.  But on balance, he is an asset to my business, someone who I enjoy doing business with, and someone I can depend on.  Bottom line, I make money, he's happy, and he continues to indirectly bring good things to my business.  Now, I could very easily throw him to curb, drop his business, lose the recommendations that he makes, but for what?  Just so I can feel good that I stuck to my principles and forbid any free rides?  Wouldn't be a very good winning hand for me.

I think anytime you are dreading the thought of seeing someone , its time for both parties to make a change.
Follow your "gut".
Take guilt out of the equation, too. That is a wasted emotion.
xxoo

Your words above are exactly what makes a lady stop posting as to sort the regulars out and only see the ones who still hold a morsel of respect for her. I have found you can not tell everyone you WIll do anal as they will try to shove any object in your ass.. about the discounts.. does your apartment people give you a discount.. or the hotel or your internet provider.. or even the place you advertise with ..? and dont you pay your rent every month as well as your bills and you never get a discount so why should you be expected to give someone a discount? .. I am sorry you have to go through this.. just shake it off .. go get a drink and hold your head up .. about when to fire? I had a prickly dick mf that came one day and kicked my dog( lil bitty one) and well i told him right there .. i cant see you if you disrespect my puppy.... IJS.. DTSFC( i just say.. dont take shit from clients)

Then it's time to Fire the Client.

If you wanna more subtle approach than "You're Fired!":
Raise your fees on your services - for him - to the point he cannot afford to see you "Fees are now (3x normal rate)".
Services for him get restricted or eliminated. i.e. "No Soup For You!".
Set a obnoxious alarmed timer and kick him out on time, clothes & all. Or do a countdown clock "You have 5 minutes.." lol

Do any of these, he'll get the hint.

Personally, I'd give a Dear John letter like an old dentist sent me once.
Basically, "We feel that we can no longer satisfy your needs, so please seek the services of another provider. We will forward your records at your written request."

Or blowing your mental status out of the water so that you are no good to work for the rest of the day.  It's time to say adios.  

If a client truly enjoys seeing you, he would be paying full price and tipping on top of that.  

When they are constantly asking for more and donating less, they are a liability.  Yes they push for discounts so they can see more ladies.  If you can't afford to play, then don't expect discounts to do so.

It has been my experience that the ones who ask for a discount never turn out good in any way.  If I allow the discount, then I get reference requests from ladies who charge 3 times more than I do!  WTF!    

I've had ladies come crying to me on the phone asking me about clients who beg them for discounts only to get shit on in the end.  

Stop allowing an inch and they won't take a 10 miles!

I agree totally with Caitlin. I have seen her many times. You put all into a session and only ask to get rewarded correctly.When I was in pro wrestling I would give it my all in the ring. Some promoters tried to stiiff me with money. It is the same in escorting. Your body and giving it all sells. It is about the money. I have seen top independents and many models at agencies. Every one of them loved me because I treated them well and never asked for discounts. I also never asked or insulted them either. I remained a great gentlemen. If an escort sets her price high, it was no different then when I commanded a higher price for wrestling. The client can pay it or go somewhere else It is all about quality and when you lose that, you have lowered yourself. Stay true to yourself

If I am correct you have recently been offering a pretty nice discount. If a guy asks for more and you "want" to give it that is one thing but if a guy is just being pushy or taking advantage of you being nice then cut him off. Tell him you won't see him if he acts that way again. You can do it nicely. How he handles it is the problem. In 25+ years in the restaurant and bar biz I had to tell lots of "good" customers to change their behavior or suffer the consequences. Some were smart and calmed down, took the taxi home I offered and left without incident. Some became angry and belligerent and had to be escorted out to not be allowed back in until I had spoken to them again when they were sober. You can't let the idea of a lost customer define your happiness in your business.

I for one would always wish that a lady felt comfortable enough with me to tell when I am over stepping a boundary whether it is sexually or time or whatever. I saw a lady recently who had been very generous with her time and donation. I was glad when she said “Listen we could obviously talk for hours but..." Sometimes I am having such an amazing time that I forget time, especially when I am entertaining in my home.

When the respect is lost on either side of this business deal the fun goes away and that is a loss for both people.

Good Luck Caitlin!

Willy

Kicked your puppy???? I hope you kicked him right back. And I don't mean just to the curb.

... and I am looking to get hired!

Caitlin,
  I found this article and although it is written for general businesses, it has some great points that resonated with me.  Their points are also relevant to our industry.  I hope this helps you in some way.  Best of luck to you!
Sincerely, Morgan Marie

This "gentleman" is clearly taking advantage of your good and sweet nature. He's asking and asking and asking and never giving anything back. This is a classic type of friend who always needs and demands and never offers any return. I've had a few girlfriends like this (and male friends, too, but obviously they weren't sexual in nature), and they can pound the upbeat and smiling core of your humanity into remnants of nothingness. I know I don't bring enough financially to the table to repeat repeatedly and consistently enough to make discounts worthwhile, so I never ask. Even if he repeats enough to make the discounts worth it from a financial point of view, it seems like he's slurping away parts of your soul. Not worth it, IMHO. Your soul and other things are too sweet.

He obviously doesn't understand this is a business deal and your livelihood he's messing with....ask him when he goes to his favorite resturant to call the manager over to the table and ask for 15% off the bill....because he's a "regular" there and see how far that goes...or better yet after he orders the most expensive dish on the menu and eats it try just not paying for it...can you spell dishwasher? Sounds like a lame A-Hole to me and you deserve better! Vent over eom

Ginger...you always say it so nicely....that's why your so special....muah