Unfortunately, way back then (~30 years ago) the rule was mostly one and done.
However, I met a few gals who would give me a full hour or at least let me come a second time. Today that is the rule, not the exception, at least with the better gals you meet on this board anyways.
One trick I used to pull was to jerk off about an hour before the date so the second round would last longer.
Now, it's just the opposite where it takes me a while to come, but I'm not complaining. The ride is better than the destination.
I like appointments of at least two hours to I can get off twice.
Does the provider allow for multiple pops? Trying jacking it before the session. Start with a lot of foreplay so that if you do cum early then you won't have 45 minutes of doing nothing.
It shouldn't be awkward. These girls are pros. So nothing surprises them anymore.
It is not awkward for me at all. For the clients for whom this has happened, the attention generally comes back to me which is of course always a great thing. Then there is lots of time for talking and cuddling and just being together. If a client asked me to help prolong it, I would, or if he appeared to want reassurance, i would offer it, but only if clearly wanted. Otherwise I just assume it is not a problem for him and enjoy the appointment. After all, he still felt wonderful, just maybe sooner than he planned.
The only time, a couple of times, I felt a little sad was when he came and then he acted like the appt was done and left. That is the client's prerogative but I would just assume he stayed for the duration, unless he really had somewhere he needed to be. But that is not everyone's style. I understand that.
mentioning to the lady that you are working on delaying, and ask her to work on some tease/denial play with you. I absolutely love that kind of thing - so much fun to get someone all worked up, and back off just before the point of no return. It also might help you build up both stamina and confidence so you're not worried about it.
Or, just don't worry about it regardless. I'm going to assume you want ladies to be more than just blow up dolls, so use some time initially talking over a drink, and the same after.
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