Nothing really, lmnopqrstu,

It's up to HIM why he's holding back. It could be a million reasons - he doesn't want to lose control; he doesn't want to share this aspect of himself with you; he gets off watching you squirm and metaphorically  "beg" for it (a modified version of a power exchange) - and now he wants you to be "in total control."

My experience with men who want to be "totally controlled" is that sometimes they don't ejaculate or orgasm in the conventional sense, mainly because they ARE into the power exchange - a sort of modified version of BDSM.

I don't know this man, but I think he is just as much of a "mindfucker" as he is into the usual in-and-out with the liquid finish. And maybe of all people, he has chosen YOU to enact this game with. He may really sense your urgency and that probably turns him on even more. Maybe he expects you to really work yourself into a total frenzy next time - and still deny you the "final prize."

Personally, I'm getting turned on just writing about it - no wonder he's got you going
The Love Goddess

I have a very good regular client. He is in excellent shape, light drinker, eats well, and is very healthy. He sees several other ladies who are all different shapes and sizes. He and I are close to the same age. We have seen each other several times.

I enjoy his company and I am guessing he likes my company as well. He is one of the only clients who has the personality that almost demands a toned down relaxed version of me.

Here is the problem:

I can cum, squirt, squeal and scream. He gets me there every time with no problems. However, for some weird reason no matter how much I try, or try to not try, no matter how long or short the session is, I cannot get him to cum.

He cums with everyone else he sees, but no such pleasure for me. I would love to experience that with him.

We are switching things up for our next visit. He will be coming to my in-call, and he wants me to be in total control. So that is why I am electing to do in-call instead of me coming to his place.

I am very focused on totally relaxing him with the full pamper treatment, drawing a bath, rose petals, cooking him a light meal, his drink of choice, and a hot oil massage complete with a rinse off shower.

What am I missing?

I see a couple of ladies who enjoy the sex being a little longer and more vigorous than I'm usually capable of these days without a little help. Unfortunately, one side effect is that it can make it difficult to ejaculate. It could be that he enjoys the protracted sex with you so much that he wants to make sure he performs and is taking Viagra, etc.

Maybe he's overstimulated.  It could also be that he's having orgasms and just not ejaculating.  Does he have a taoist or tantric practice of protecting his chi?  The only thing I know (in a mechanincal sense) that shortens the distance to ejaculation is prostate stimulation.

impossible to know from this distance.    
One detail...  you probably have already done this but be sure of optomim condom fit.   I'm very aware since I had this problem in the past.   What gets a guy off is friction in just the right places.  The condom must some move in order to cause friction.  It needs some lube but too much will cut the friction to zero.   Shape can be important too, allowing movement while still staying on.  The most erotic experience I've had with a provider was when she applied the C with her mouth.  I barely felt it go on & there was no interruption in the action.

Control the environment.  Comfortable in every way.  Free of distractions.  Music should block out noises but not draw attention away from the action.   His focus on pleasing you, can detract from his focus on his pleasure.  It's ok to please you...  but at some point the focus must shift.

Now, if you have been so well satisfied...  Are you able to apply a good firm squeeze when necessary to take him over the edge?  I have found some women can not.  I have gotten tired & frustrated...  expending my energy...  when it might have been better for her to recover before proceeding.    

It may be he's holding back for some reason...  he may not even know...  
Best wishes,
skb

Extremely effective. Very interesting that he cums with others and not with you. I can tell you that chemistry and familiarity makes all the difference for me. I release with only half the providers I see. A lot just depends on my mood, maybe he finds you relaxing to be with?

How certain are you that he climaxes with others?
From the male perspective, it all seems quite unusual.
Could he have a motive [or a psychological reason] for being disingenuous?

It could be the condom you are using. There are some that just don't work for me, no feeling.  You could try using a female condom, in my experience it is the next best thing to nothing at all.

It actually seems to happen more when I am having a good time, and I do not think it has anything to do with mind-fucking since I would prefer to finish, but it is not that critical.

Here is how it seems to work.

I am having a good time, a very good time, and I want it to continue. So I get close a couple of times but slow up, distract myself, or whatever so that I do not hit the finish line so I can keep going. Eventually I get to a point where (assuming the sex is hot) I am sort of perpetually in a panting stage of near orgasm, but I can no longer get quite past it. Or sometime I begin to lose interest, but usually in that case I can just finish before I get to the "high state of enjoyment with no finish."

Realistically, I am pretty sure there are a few options for me to finish - the right HJ, BJ, or perhaps a little anal encounter might switch things up enough to get over the finish line, but by this time the big O is pretty much beside the point. I am a quivering mass of very happy jelly.

I also understand how this can be upsetting to my partner so I have been working on a way to explain it. Not quite sure I have figured that out, though I do insist I had a hell of a good time, quite honestly. I suppose this inevitably leads me to state that the orgasm may be overrated, or at least focused on to the extent that a lot of other very enjoyable near-orgasmic states are blown through.

But that is just me.

So, OP, the point is that you actually may be sharing something special, and not missing out on anything. After all, wonderful sex without O is the exception, isn't it? So you are not like all the other girls, and since he keeps coming back, you should consider that a compliment.

Thanks for all the great info LG. Wish I had talked to you in high school - the years of confusion I would have avoided!