For me, with most ladies, the first date was as good as it got. I have been back on a lot of second dates, asking myself what I was thinking. I have a good idea why that is the case, but this is not the question you asked.
There have been those special few that I enjoyed seeing over and over, letting things develop. It is different depending on the lady, how you click together, and you, so it is hard to predict how it will go for you, but here are some possibilties.
If the lady either does not really like providing and/or dislikes you (this may not be apparent to you for a while), she will gradually begin to take you for granted and the performance will deteriorate. When that happens you have two choices - one is to assume something is wrong and try to fix it, and the other is to walk. Trying to fix it is almost always a terrible decision, IMO, because the problem has nothing to do with you and is not something you can fix.
The next situation is that she is a professional who likes her job and wants return clients. Once she determines that you are a good client, she will work harder to please you as she learns what you enjoy. This can work in a number of ways, depending on her approach. Some ladies are pretty rigid in how they provide, each session being very similar to the last. With them the sessions may adjust a little to focus on the parts you enjoy most, but that is the extent of the change.
On the other hand, some ladies are adventurous. With them each session is different, and as you get to know each other better they will be open to, even suggest or offer, different things. Do you want a comfortable, predictable experience, or always changing play? Once you know that, you can also better predict whether things will develop well with a given lady.
You will also discover that some ladies prefer to extend the social part of the dates and minimize the sexual, while others prefer the opposite. Male bluster aside, there is an attraction to both approaches and only you can decide what works for you. But if you want to fuck her for 90 minutes without stop, and she would prefer to talk, hold hands and rub your neck for 60 minutes, then screw for 30, the dates are not going to improve.
Depending on how often you see the lady and her approach to this, you may also get offered other things - these could include a better rate, a little more flexilbility about time, etc. The key thing to remember is that she is doing these things because you are a good customer. If you start demanding something extra, you will stop being a good customer and the likelihood of getting special treatment goes way down. Wait for her to ask or offer, though if you feel like something is a deal breaker, it is better to tell her so before you just disappear.
In the end, you should do what you feel like doing. If you enjoy a lady and want to see her again, go back. If you feel like seeing someone new, do that. Going back to see a lady because you expect it to get better in some way is a losing game as there is no guarantee she will do anything more or different. For the past six months, I have only been seeing the same ladies, but for a long time before that I saw two or three new ladies every month. Maybe I finally found the right ladies, or maybe something about me has changed - most probably it is some of both.
Hope that helps.
zig