I'm a provider, so I'll give you my perspective on the whole thing.  I'm not FS, I provide FBSM.  Whenever I see a client, I always take a few minutes at the beginning to find out what they want, even if it's someone I've seen before.  Maybe they want to change it up this time and do something different or maybe they want consistency and for every session to be the same - either way, I want for the experience to be pleasurable for the client.  So I always make the effort to find out because my priority is to make the client happy, every time.  

I also use that time to lay out the rules, so that I won't have to decline anything during the session.  I like for the session to flow nicely and it won't if they ask for something in the heat of it all, only to find out that I don't offer it - it's a major mood killer.  I also ask before we get started if they want one or two, even in a 30 minute session (because I aim to please, and it's my favorite part anyway).  And I always offer for the client to let me know during the session if they change their mind and feel ready for a second.  Maybe you can use this approach and talk to  her before the session starts, so you know exactly what will go down beforehand.

Personally, I would suggest at least trying another provider.  You may find another that you are more happy with, and one that will give you everything you want.  I definitely feel that you deserve that much, especially because you are offering a donation/gift.

1.  If you want a second cup just tell her something along the lines of WOW, that was so good I want to do it again.  Most girls that allow a second cup will enthusiastically get going on # 2.

2.  As far as seeing other providers, that is up to you, but it would give you something to compare your present level of service / satisfaction to, and you might find someone that is more in tune with your needs and desires.  Just do your research.

Most importantly, have fun and enjoy yourself.

1) Do I wait for her to initiate or should I just ask for a second cup? What is typical?

If you wait for her to offer a second cup you will most likely wait forever. Providing is a job and I don't know too many people who will intentionally work any harder than they have to. That doesn't mean they won't do the job very well if you help them to understand what they want.
Yes, you have to ask.  Give yourselves a few minutes of recovery time after the first pop and then say something like "That was great, can we go again?"

2) Should I move on to another provider?

Only if you don't get satisfaction from this one...

Ok, that takes care of question #2 I know you have to do all the research and contact a new escort and get screened. And there is the chance of having a bad time with a new experience. But I have found the "one and done" theory works.
I have a fav that I see regularly, but I like the variety the hobby has to offer.

Now question #2 I ask, when I desire a second cup. The key is initiating the second cup with enough time to finish. You know by reading the reviews which ladies offer a second and many ladies on their web site will mention offering MSOG.

Time to move on, don't worry about hurting the ladies feelings, just don't call her. Trust me she'll be fine and so will you when you find a lady that offers you that second cup.

I know for me, I will gladly do a second cup, espcially if there is 30 mins left, but I don't assume my client wants one unless he gives me a hint and then its good to go. Usually when the appt is set on the phone, I pretty much know a second cupmight be in the picture..price doesnt change. But at least I know, when #1 is over, wait a few and go for #2 a different way

You can always try someone else , but I am assuming since you have seen her 5 times the comfort level is there. You should talk more to her and tell her that you would like to try something different. "Hey, this time, I was thinking of trying to go twice, don't know if I can, but lets try". If she says no, I would most definately find a new provider, you are her regular and she should appreciate that and not take it for granted.

Just my opinion, and you know what they say, "opinions are like azzholes, everyones got one"

If you've seen this provider 5 times, I would imagine you talk to each other  - Just ask. There are too many that will rush the pop, so do a search for the body type, etc that you enjoy,  then check out the reviews and contact. You can tell plenty from a phone call.

Sometimes you guys want the same thing to keep you happy, sometimes you want to mix it up... she is not a mind reader and apparently has you figured as a Steady Eddie.

If you ask and she is not enthusiastic,
move on.  It's your time and your dime, you should get (within reason and boundaries) what you want from the session.

xoxo,
S.

.. suck on her boobie.. or lean in for a kiss! I mean, if you're 30 or 40 minutes into the session- touching her and sporting an erection.. something tells me she'll get the hint!

I kinda feel that you were ripped off.
You can't be that shy after 5 dates.

I always keep my friends busy the whole time. Unless they tell/show me different. It is your time.

any provider worth their salt will go for a 2nd cup if you have time for it without you saying a word.