Sounds like you are encouraging the behavior. Yes, you need to put him on your "Do Not See" list. You need to stop encouraging him by using him when you need the money. He won't stop asking for discounts but you take the full donation when you call him and he only gets 10 minutes. Is that fair? Answer to that is No.
It's decision time for you. You created this situation. Now you need to decide. End it or put up with it.
There is fault on both sides in this case. That's my blunt, honest opinion.

...and I get the feeling there is more to this story.

You're not being mean, you're being a good business woman if you let him loose. He's breaking your rules, forget about his being consistent, you'll find another consistent client. Remember, clients are like buses, there's always another one coming.  

Posted By: badbiz

Had to cancel an nooner today because this client is nutso! I really can't afford to say no, but he won't abide by any guidelines I have set up! I am new, and he is totally new too, but the ways I have tried to work with him and he just doesn't care and is totally disrespecting my business and my time. I want to tell him off and tell him to find it elsewhere, but I know when I need to, I can call him and he will come, even for 10 mins but pay me regularly. Ok so, I say no discussions on my phone we can talk about encounter when we meet and he sends texts all day while at work saying he's horny, and he wants to F*ck and everything! Then, I say no discussing $ and then he asks me every time, how much, how much, how much? He expressed he wanted some specific roleplaying/ fantasy done, but when I let him know, he needs to pay an upcharge and I need more time for the appointment, he wants a discount? I NEVER told him he was entitled to a discount, I agreed to his roleplay/ fantasy, but I do require some time to fulfill what he wants done and I need to purchase props. He's somewhat consistent, but when we do meet he has OCD and has too wash and needs boatloads of wipes before and after. IDK if I should keep him for the easy stuff and decline the more in depth visits or just let him pass because if Uncle LEO is around, this dude is sure to get me busted! So I guess my inquiry is should I just let him go? And I hate being mean to people but I don't like being disrespected!

Let's hope that you smarten up over time...

If you're going to be "successful" in this biz you're going to need to learn, and quickly how to deal with guys like this.  And your post is really all over the place in terms of "boundaries".

First, you claim that HE texts you relentlessly discussing items that shouldn't be discussed electronically.  That should be a VERY easy fix...just tell him in NO uncertain terms that should he send you any more of these you will put him on your DNS list (and set it up on your phone as an ignore).  So this is on YOU...since you can't control what any john will do.

Then you discuss he's seen you quiite a bit, but there seems to be an issue of compensation.  Why?  Your fees are what they are.  And if he is seeking something else, you can either agree, or disagree.  And if he wants to persist, again it is YOUR decision to terminate this immediately.

Then your last item I find a bit unusual.  To have a guy that is into cleanliness I would think is a very positive attribute.  Wait till you get the guy who wants to be rimmed and still has shit in his ass.

I know that the bucks are needed, but to "risk" being in a bad place as you think you will be, time to move on.  Run some ads, calll the other clients you have, get a part (full) time job.

If you don't figure this out quickly, you will find others taking advantage of you as well.  Perhaps you should consider contacting an agency in your area and spend some time there "learning the ropes" of this business.  Being an indy from the get go is tough, and it sounds like you are NOT in a position to teach yourself.

Good luck to you in whatever route you go.

You've been nice and expressed your displeasure and given him a chance to behave better, which he has refused to do.  Cut him loose.

you treated your hair stylest, doctor, or accountant like he is treating you, what do you think will happen?

Cut him loose.

So you don't want to shut your business down.  Being friendly is not necessarily bad...  to a point.  You've got to be the pro & control the relationship.  Anybody who pushes your limits, you wind them down or shut them off.  Providers have to do it every day.  You try to be nice.  You tell them "it's you"...  that you are getting too close.   Sometimes, you can successfully control this but in this case I doubt it (because you've tried).  
All the rules & cautions are there for a reason...  to help keep everyone safe.  Your only responsibility is to yourself.  This is the down side of being an independant.  In an agency, the manager would handle this client.  You have to switch to your manager hat.
H  

...someone needs to know what's up.
Personally, I prefer a seasoned Hobbyist and one that's wiser than I am so I can be free minded and relaxed with no cares in the world but getting laid n paid....ohh yeah!!
What a beautiful day..!