Ive been dating my boyfriend for 3 months now and he's never had an orgasm. He's in his mid forties and we have had sex before we started dating; approx 3x in the last four yrs & I can only recall an orgasm once I think. We do talk about it occasionally because I have a challenge with it, not him. He says it's because he used to masturbate so often (no g/f) that he thinks he lost sensitivity. But our sex is phenominal, no complaints on either side, we're very open, very experimental etc and though he tried to reassure me that it's not a "bad thing" I can't help but think something might be wrong?? Should I just quit asking him or worrying about it and think "when he does he does?" or what?

It has nothing to do with you...

(Or everything - depending on how you look at it. :-)

He is a self-stimulation guy who now has stimulation girl. You.
He was probably used to porn and a toss before bed and what not...
And now needs a "trigger" to cue him to relax and finish with you.

Are you verbal in bed? You may surprise him with some fantasy talk.
Mix it up... And let him show you how he likes it (masturbate) when/if he doesn't finish.

Go slow. Don't make it orgasm/goal oriented. Make it about PLEASURE.

Good things will follow... and yeah, I'd not talk about it... just adds to it.
Wait a while longer, but make him know how much you LOVE sex and want it
And go for it... he'll let go eventually I'd bet...

So he can perform fine for you, but can't quite get there.

Have you tried to make it "all about him" as in telling him to not hold back? Sometimes holding back requires you to suppress the sensations, and then by the time its "ok" to release, its hard to build back up to that place.

Um... there are a few things you also can do also, if you haven't.

One "trick" to drive a guy over when its stalling is to try to reach around and tug, grab, pull some on his "guys". It can depend on the position, and it might not be easy, but for as much as we guys are protective about not getting racked, during sex the same things that might have us recoil normally can be interpreted as pleasure. I know it's a silly visual, but it one of the reasons a guy might like coming at you from behind... the swinging motion and "slapping" of the guys kicks up the sensations. So... a "reach around" might help?

And, I've posted this here a million times so people are probably tired of my saying it, but a great position that some may not have tried is him on the bed, on his back. You on top of him, your back to him, laying on top of him. Ease him inside you. He has some work to do, shifting you up and down toward his head and feet... so if his health isn't good it might not work. It really can work the legs some. But it puts weight in all the right spots and I think it is as powerful mentally and it feels physically.

He has access to your neck, ears, chest, while your hips put all the right pressure in all the right places, in particular some often overlooked sensual spots just outside the groin area. If you can angle yourself to the side a little you can turn your head hard and go after his ear with your mouth, especially when things are starting to level out...

Just a few things.