It is, however, one that has been asked and answered many times over the years on this board.

I don't think it has to do with your phrasing, as much as it has to do with that particular girl's personality and views on the subject. Let's assume for the moment you are meeting her for the first time. Many ladies want to feel comfortable with you by chatting you up for 10-15 minutes before the fun begins. If you rush those type of girls you may experience some push back.  
Of course, some others wont care at all as not all providers handle these situations exactly the same.  
There are also providers who will state somewhere, either on their website or ad, that its 1 orgasm for 1 hour. They may word that differently, but you will get the hint.  
There are two possibilities: increase to 90 minutes (but with rate inflation I understand that may not be possible) or see the girl first, build some rapport and let her get to know you, then ask her during pillow talk of date 2 or 3.  
That's the beauty of seeing someone multiple times, as her trust in you grows and deepens, she may open up some possibilities that wouldn't be available upon an initial meeting. This has happened to me on many topics over the years be they BDSM play, fetish requests, etc.

If you post a bounty on each load she pulls out of you I bet you'll get your wish lol

You're setting yourself up for undo pressure to "perform" and for her to "get you off" twice within 60 minutes. And I have to say, but we're not young bucks anymore...age creeps up on us.
But, this is what I would do.
First I would look for a someone who is apt to MSOG (See her reviews) definitely avoid the one and done girls. As someone mentioned, maybe a 90 minute session will give you more time to catch your breath.
And this is me.. I would look for a mature woman. Avoid the young chicks, they don't have the patience or experience in dealing with a gent with your goals.
And so with all that I mentioned, add this...relax, enjoy the moment. Let it flow and if it happens, great, if not...don't sweat it.
Once you find someone who gets you, then enjoy and let her light you up like a pin ball machine.

You think you've got problems?  I am 15 YO than you. And I am just enjoying what comes my way. Which is pretty good. Surprisingly good.So enjoy it whenever it is.

I am 60 also.  Most of the time I will book a 2 hour appointment for 2 pops.   Its extremely important that you do a lot of walking for blood circulation on a regular basis.  It also helps that the provider you are seeing does a lot of walking that helps strength her kagal muscles for kung-fu pussy vice grip.  

This is what I do for 2 pops in a hour.  I have a refractory time of 10 minutes.  

1. Choose providers that are very attractive that give you an instant hard on.    

2. The provider needs to have tight grip especially for 2nd round.  Some providers who do greek will ask them to greek them for the 2nd round, generally the anus is tighter than the pussy.

3. Book a appointment in the morning when you are well rested up.

4.  2 days before appointment do leg workout

5.  Day before the appointment do dead lifts.

6.  Drink pineapple juice between rounds.

7.  Before the appointment make sure to be well fueled and well rested.

As had been previously mentioned, the first time with any provider, not surprisingly, the girls will want to spend some time to get to know you (which is why, many ladies insist on a 90 minute session for a first meeting).  So, putting the pressure on right at the start may not have the results that you desire.  Therefore, I advise two strategies.  Unfortunately, both of them are going to require a greater investment in time and money.

 
1)  Find a girl that you really like, such that you are happy to see her twice.  In the first one hour session, let her know that you intend to book her again, and you'd really like to set a goal of two shots.  Most of the ladies that I've met would accept that challenge.

 
2)  If you insist on seeing a new girl every time, schedule an extended session (e.g. 90 minutes, 2 hours).  Embrace the fact that you're a more seasoned partner now.  Allow yourself the time to relax and recover, and allow her the time to get to know you and your body.

 
P.S.  Not a stupid question.

Be happy for that one good one!

That will give you more recovery time and a better chance at two orgasms.

Next time you meet someone you really click with ask at the end of the session, "how about if next time we..."
Asking someone you don't know before the session risks an awkward situation if she's not game or has a high ask.

 
Now if you already have someone you want to see again, during booking, I might ask something like "is there an extra donation for MSOG?"

 
If your only goal is to unload twice in an hour, best to get #1 out of your system as soon as possible. A BBBJ in the shower is a nice start. You can ride out your recovery time with small talk or returning the favor until the urge hits you again. It's your money, you need to set the rhythm.

Almost every one-hour session I have, I experience two orgasms within the hour . . . . one for me and one for her.  Lol

Sexual performance is actually a very, very good marker of overall health. If you want to perform better, the only real way is to take care of yourself. That's hydration, eating clean, laying off the sauce, getting good sleep, exercise (including kegels), maintaining a healthy weight, etc.

 
I know that's a tall order just for an additional pop, but, health pays dividends.

 
 
Personally, my current record is 5 in a couple hours. Probably could have done more, but, I was pretty gassed after that and needed a break. The secret to that is to have really good pelvic floor muscles and understand how to use them, then when you get pushed over the edge, hold your breath and clamp down hard, stop all stimulation, and then relax as you take a breath. You get a 75% orgasm out of the deal, but, no refractory period so you can get right back to it in like 10 seconds.  

 
TL;DR; If you want to fuck like you're 20, you need to be healthy like when you were 20.