I haven't read this whole thread but I often ask SPs in massage shops whether they allow 2 pops, some do and when they do, I often manage it. I time it so that during the 1st hour I have a HE within the first 25 min and then ask her again about 10-15 min before the hour is up as I know it will take me longer to reach climax.
Technique - what I often find is that a simple wanking / masturbation method doesn't do it for me, in fact it kind of kills the mood makes my man go to sleep. As someone correctly said in the first few posts on this thread, it's often more about mental state than physical action. I mean, of course you need physical action but I always tell them to use two hands in a cork screw manner with each hands (well oiled) going in opposite directions as if giving someone a childhood Chinese burn on their wrist, but of course, easy on the old fella. I get powerful orgasams with this lingam massage.
I often just close my eyes and think dirty because its the thinking dirty bit they pushes me over the edge / threshold to get a powerful orgasmic cumshot. I have to admit, I'm often complimented on the amount of my delivery and getting tired of the same lame comment by SPs saying "oh my god, you clearly haven't emptied your sac for ages". Dumb SPs haven't clocked on to the fact its not as if my balls are turning blue and need emptying like a cow's udder.
It's all in the technique - to get a strong orgasam, a state of mind where the body and mind cannot guess the sensation of two hands going in opposite direction, creates a perfect and very pleasurable sensation that leads (well me anyway) to a powerful cumshot.
As for the 2nd pop, if I'm running out of time and despite all of the above, it's still not happening, I turn over to lie on my front and ask her to reach from under and behind. WHY? Because again it's another sensation that is different from a simple and crappy wanking sensation. I've cum almost 100% of the time (2nd pop) within 20-30 min of the 1st pop, when I'm lieing down, and butt raised slightly off the massage table and getting her to massage or wank away whilst my mental state is somewhere else.
I encourage you to try the above steps, and report your findings or "outcomes" here on my suggestion.