This is an interesting question.
I tried searching my memory banks in order to answer accurately, and I can't specifically remember any P4P session where I shot my load more than once.
I didn't start doing P4P until after I was 40 years old, so my staying power and recharging time were both a bit decreased from my younger years. Another qualifier is that I don't do overnight P4P sessions, so just like your question states, I'm referring to one-hour (or an hour and a half) and two-hour appointments.
I'm the kind off guy who gets more out of the actual sex acts themselves than I do out of the finish, which basically means that for me, it's the journey that counts, not the destination. I like the screweing more than the spewing. I'm fortunate that generally speaking, I don't have dysfunction issues that plague a lot of men, I can usually last a good long time on most occasions. Once or twice, I couldn't finish at all, just stayed as hard and as turgid as I used to back when I was 20 years old, and as the time limit for ending the appointment was quickly approaching, I had to tell the woman that I wasn't going to cum. We tried changing positions, dirtier talk, harder fucking, deeper fucking, faster fucking, even tried switched to other activities, handjob or oral, but no dice. I have to admit that all of what we were doing by turning up the intensity was a wild ride on its own, almost like doubling a session, so I really liked that. She had to leave just like I did, so I told her not to worry about a happy ending, I was just as satisfied with the happy journey. Staying completely hard for an entire hour of sex, or 90 minutes or 2 hours, that was a blast.
Just like any older guy my age, there has been the odd "failure to properly launch" or "petering out before the final countdown", but they haven't happened often. On the first incident, where I had trouble even getting erect at the beginning of the session, I was with an older woman who had experience with that happening to other clients, she was smooth about it and together we amped up the foreplay to a level that soon produced a pup tent. I lasted the entire session, eventually came like a firehouse, everything was fine. On the second incident, about 3 quarters of the way through the session, I lost my erection and nothing seemed to work on getting it back. It didn't help that I was with a very young escort (mid or late 20's), and she took it personally that my dick had gone soft under her tutelage. She kept asking me why it had happened and why it wouldn't get hard again, really whiny. She actually thought I had done it on purpose and that I didn't want to finish, didn't want to get hard again. Her attitude was neither sexy not inspiring, it made things worse. I did want to finish, I did want to get hard again, but she didn't join me in trying to bring it back. I had to tell her that as the woman and as an escort, she was part of the equation and that I needed her help. She seemed turned off or offended by my suddenly flaccid condition, so between us, I did most of the work in getting myself action-ready again. Fortunately, it did get back up after 5 or 10 minutes, both of us sort of pretended that nothing had happened, and we picked up where we had left off. I shot my load after we got back into it.
I don't even attempt a second round these days, and I haven't attempted one in at least a decade. I guess I don't have the patience to sit around and wait for the buffering wheel to slowly show my percentage of ammo rebuilding, and after I fire the cannon once, my mind switches from Fuck Mode to Cleanup Mode and Return to Real Life Mode (which includes running my alibi checklist through my mind).
I do look forward to the day when I can schedule nice slow and relaxing extended sessions, either several hours or overnights. The thought of lazily and endlessly fucking for hours on end with multiple salvos and multiple breaks is certainly an enticing escalation of how I currently spend my time with escorts. I'm top of that, I'm especially looking forward to doing it as threesomes every now and then.
