If the gal you are seeing is a regular who knows you always like two or more rounds, then often they initiate it, but when seeing a gal for the first time, more often than not the client must be clear about what they expect.

 
Back when two rounds was a thing for me, I would make it clear from the outset that I was looking for two, so seldom had any difficulty with that.

 
I recall one session (2 hours) where the gal insisted on a third, but the is rare.

 
Occasionally, I would be disappointed that the gal would resist a second round.   That was before I was more experienced and made my desires clear up front.

 
Back in the bad old days, some gals had a one and done policy where the session was over once you came, even if only a few minutes into the session, regardless of whether or not their ad said "one hour".   To fend off that embarrassment,  I would often masturbate just before heading out to the session so I'd at least have a decent 15 minuets of actual sex before coming.

I can't really make it happen until I have a 3-4 hrs of downtown. I have gone  for the 2nd shot maybe once or twice with a hooker in last 20+ yrs or mongering.  When i do overnights with my SBs I often go for 2nd round in the morning..

Hey MintyFreshness,  
  Maybe the last session(s) you had where the "PROVIDER(S)" were chatty.....Maybe they wanted you to kiss her and make the move. Have you thought about that?

Intermission.

Usually after intermission with the happiness of hydration it’s go time. Sometimes I will offer a massage to relax & calm a new friend, so it’s not to much pressure. Multiple pops are always available if able. Idk about other providers, but I am only speaking for myself. Maybe just speak out next time, and say something to your provider.

How much you used for the first round, and how much time is left.  If doubling your first number adds up to more time than you have left, they will usually not offer a second round.  It's not complicated.  

The ladies I've seen over the last few years all seemed to be expecting it after the first pop.  A few have even initiated, or at least tried.  But they all quickly realized that, given that I'm a superannuated player, it's just not gonna happen.  Mostly, the ladies stay naked, lounging around and giving me a come-hither look--until I start getting dressed.  I particularly like that some of my duo dates will continue playing with each other as a way of enticing me back to bed (at least that's what I tell myself).  Oh to be in my 20s again!

There's agencies that have that on their menu...And this can get complicated .Say you finished your first round and you have time for one more shot, then she  kinda :cough,cough: and sticks her palm out, like its gonna cost you sir....what a buzz kill, huh? But that's a different story in its own.
But, going back the original thread. I usually start the second round, if I'm feeling it and if we have time. Most ladies can pick up on the vibe of the guy. Usually it happens when we're relaxing after the first tryst, her legs draped over me while we're laying down,sharing a drink. Conversation is smooth...and then all of a sudden..."Oh,oh..what have we got here" and then it's off.

I think it really depend upon the situation and the two (or more) people involved.  

 
I love having her initiate, but if she doesn't I certainly will when I"m ready.  

 
If you want it a particular way, best to just say what you want.

If you never make a move, I think the girl would mostly likely think you are done.

This is contingent on what the provider advertised or agreed to ahead of the date. Always enquire ahead .

I have always went by the rule that an hour appt is an hour, 60 mins or a little more. So I am good w however many times he wants. But I also sometimes feel weird about initiating because you want them to know you are open to it but you don't want them to feel pressured or bad about it.  I usually ask "can you go more than once" at the beginning that way they can just pop one off if they do two.  

I have had men tell me that they have booked 2 hour or more appt and she still one and done them. I could see men would expect more than one if they book more than an hour and the provider should realize that because why would he book 2 hours if 20mins in he cums and then she leaves. That's not cool.