Seeing someone for the third time.  Her website has been updated to include VIP Services +$$$.   How do you ask what is included in those services?  I want to ask nicely, but I am tiptoeing around etiquette.  I asked what the new VIP was all about, and her response was "What do you want?"  Do you see that as an open invitation to be direct?

So, I say answer her. How you word it is key. I think if you're polite, she either says yes or no, or a mix of the two if you're asking for more than one thing. I'm glad to hear she at least asked you. It bothers me when I see VIP and have no way of knowing what it means.

You are right to be cautious here, but it seems like she opened the door for you to be explicit BUT...it so depends on her personality. Some women are just super easy going and don't get offended easily while others have a million rules and are more prone to have something like this set them off.  
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So, I have two options for you:
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1) Since you already have a date set with her, why not bring the extra money with you and ask her in person? That would be the safest route to take to be sure.
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2) But if you want to know before meeting, maybe reply with something like, "Is it ok to just speak totally honest about my request by email? I know some ladies dont like that, and I always respect that, so if you feel comfortable with me being totally upfront, lmk please." That should take you off the hook. lol.

Of course it's also a trap if your idea of what $$$ should get you is not in line with hers.

VIP = GFE

Depending what he is asking, some things might not be on the table the day of because they require prep. For example, I know many ladies who offer Greek will not allow it unless arranged in advance because they prep for it.

They may not be on the same page, so to speak, when it comes to what he can ask and what might land him in trouble with her. There aren't any hard and fast rules here as every woman is different and you and I do not know her personality type which is a big unknown here. In addition, text/email messaging especially can be fraught with potential miscommunication.  
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He has seen her several times now and clearly likes her, so there’s a chance, however small, that he misreads the situation and oversteps, even if it seems on the surface that she has given him the green light.  
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Personally, experience has taught me to err on the side of caution in these situations, especially since many women explicitly say never to mention sex acts in ANY email correspondence ever. He is wise to be cautious here.  
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Imho, in a business as legally risky and discretion sensitive as this one, it’s never bad advice to double check with a provider before doing something that could potentially be seen as a breach of etiquette, regardless of whether you or I would consider if that "breach" had any actual merit, since she seemingly gave him the ok previously.  
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Is my method overkill? Perhaps, but if he is more the risk averse type, and he sees himself getting together with this girl many more times in the future, my suggestion would virtually assure him of a positive outcome.

I hope by then you’ve established some kinda comfort level where you can ask .
Don’t be shy …who knows, you might get the grandfather rate with free anal.

Me personally, the invitation she provided is enough. At that point, I’d rather take my chances.

Everyone falls a bit differently on the risk aversion scale to be sure and there is no right or wrong re: same. The one last thing I would add, and I didn't catch it until just now, is that the OP has been doing this for 20 years or so and he was expressing a concern re: etiquette. That is telling to me.  
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When someone with that amount of experience is torn on what to do in a sitch, maybe my middle of the road approach will suit him best, but only he can answer that question as there are still several unknowns here.  
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Lastly, he has to ask himself what would happen if she gets upset and he loses her over it. I don't know the access he has to quality providers (that he can see) in his area, as that would play in to my advice to him as well.

Personally, I get concerned when anyone is so attached to a specific escort he’s afraid she may cut him off so easily. I understand the etiquette concerns. If she hadn’t invited him to ask, I would err safe initially. I try to live somewhere between respectful and without fear.

My thoughts exactly. By the time I've seen a pro 2 or 3 times I know her pretty well and have no fear of speaking with her explicitly. If she isn't comfortable answering then there's no reason for subsequent visits.

sadly i have seen more and more that  VIP is no longer just GFE  but includes  BBFS ...  i think our community is getting more comfortable with that than it should ...  reminds me of the guy who jumped off the 6th floor saying  "so far so good"  

He states she offers VIP +$$$, so it costs extra. This providers VIP is not the same as GFE.

The main reason I can think of for providers not wanting to discuss details is fear of opening themselves up to criminal charges if the client is actually LE.  

Just add a Zero to the price and you’re in the club

I see you've been out of the game for awhile,so this girl is someone you haven't seen in awhile. And now, you want to get reacquainted with her but she has updated her website and seeing that's its been a while...you noticed that she now has "evolved" and now has a VIP menu..How am I doing so far?? If I'm off base...then fuck it, I dunno.
But you contacted her, and she asked you what you had in mind, so with that....just tell her your kink.
And yes, that IS an open invitation to be direct...I dunno know what's the big deal?

There’s something about her response that turns me off and would have me looking elsewhere. It sounds like she’s trying to negotiate what VIP means instead of just being up front about what she offers. In my experience it isn’t a great sign. I also hate the term VIP because it has so many different meanings and usages. The word’s meaning is ambiguous as a result, and functionally worthless as a client. You won’t know what it means unless you ask, which results in your current situation.
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If you want to go through with it, just ask and be clear. Maybe use words like “greek” but don’t beat around the bush too much. Be fairly direct and ask for what you want. Maybe she’ll learn to be a little more clear in the future.

about offending a provider who is talking in code.  The only thing you want to find out is, "What's the code mean."  I find very few people are offended by humor.  I would say this . . . . "I'm not familiar with your terminology regarding VIP service.  Does that mean you are going to wax my car afterward, cook me dinner, or WHAT?"  If this offends, it tells me I shouldn't be seeing her anyway.  If she says it's BBFS, then I also wouldn't see her.  If she says it's BBBJ, DFK and/or DATY, then I still wouldn't see her because these services are a standard part of GFE service that I'm not going to pay an upcharge service.    If she says she is going to fuck me in a hired limo for the extra $300, then yes, I would see her.  Sounds like my kind of girl.   See, boys?  It's not complicated.

You are spot on Hpygolky, that was my exact line of thinking.  

Thanks for all the feedback.  I am glad I asked, as VIP didn't mean what I had hoped for.  

Usually a follow up brings us a conclusion to the story. What did VIP mean to her? What did VIP mean to you?

yes inquiring minds want to know !!