Hi! I believe I can be of help in this issue.
First, let me say I can imagine how frustrating, disappointing, and worrisome this situation must be for you.
And it is that frustration, disappointment and worry that I want to address here because I believe that this is where you can have the most success in making a positive change for yourself. This problem is a form of anorgasmia. This can occur to an older, mature male when his genital muscles get conditioned to masturbation exclusively. The mind creates that sex pattern and sticks to it. Then when a different type of situation is introduced it doesn't respond accurately, which causes anxiety. Which then reinforces the brain to do what it knows to do and respond to what it knows to respond to and in the same way, which causes more frustration and the vicious cycle is underway.
I am glad we have ruled out the presence of an organic, medical condition causing your anorgasmia. Psychological causes are the most common in anorgasmia and so we can focus on this. I'd like to make three suggestions to you as an answer to your question and directions for you to follow.
One: I rarely recommend hypnosis. But here I'm going to agree with you and recommend it! Why? Because there is no other symptom of a life problem that is debilitating going on. Now here's the important statement about hypnotherapy: hypnotherapy can help with a specific problem and that's why I'm thinking of it. HOWEVER, there are good and honest hypnotists and there are other types. Your only way of assessing is two ways: first, make sure he or she is a licensed psychologist or psychotherapist. Don't let anyone tell you they are a licensed hypnotherapist. There is no licensure in most states that I know of. It's all a "self-licensing" which is not good enough. So you want to know his or her license number as a psychologist and call the state licensing board to make sure there have been no complaints filed.
Two: psychotherapy. You would want to seek an experienced sex therapist. By that I mean a psychologist or psychotherapist who is certified by either the AASECT (http://www.aasect.org/) or the American Board of Sexology (http://www.americanboardofsexology.com/). They each have a listing of their certified therapists. The American Board of Sexology is a bit more prestigious but that's not a big deal here. You want to find someone who seems to you very experienced in male problems as opposed to female problems. So, interview the therapists before deciding on the one he will go to therapy with.
Three: Okay, this is the "do-it-yourself" answer. I sense from your question that you would like to get this kind of help if you can. That's possible but you have to agree that you aren't going to feel like a failure if you don't succeed.
Okay. First, one of the biggest reasons for anorgasmia, along with religious beliefs and guilt, is performance anxiety. And you have already identified that as the culprit, right?
Performance anxiety is a built up fear of not being able to ejaculate, not being able to impress one's partner, etc. It works its way into the person's subconscious mind until the person doesn't even recognize that is the anxiety. It happens to athletes in their sport when they go into a slump. They get performance anxiety. So how do you work on it on your own?
You have to not make it SUCH a big deal for any self-help approach to work. You have to accept, okay, you have a hang-up; you can't have a good erection and an orgasm right now. This is not the end of the world. Why? Because the self-help I'm trying to teach you is that the key to sex you have to work on is: PLEASURE and not the erection to ORGASM routine! I need you to instead of identifying how you can have the erections and orgasms instead reorient your view to how can you have pleasure. If she's having pleasure through orgasms, great. One day you may too. But that doesn't mean that if she touches you, intercourse when it is available for however long it is available, and oral sex can't be pleasurable. If it's pleasurable, enjoy it. When you tire of it ask her to stop. Same with her. The purpose of your having sex together is to ENJOY each other, not a script.
Therefore, I would like you to print out my answer and the two of you read it and discuss it. So, the key: when it stops being pleasurable; when you and/or she's tired of it, that's when she's had enough and you've had enough. End of story until she feels like having pleasure again or you do. If that means the two of you watch a movie and then go to sleep or have some more pleasure, fine. If it means just her coming and you can relax while she strokes your back, fine. Do you both see the picture? You're too focused on this stereotype and you need to get out of that box right now because you're not there.
So, learn to love with pleasure and have a good time together with your partner and enjoy. Pleasure is relevant! And pleasure doesn't have to be such a stereotype...
And again, don't feel bad if that doesn't work on its own and you seek the help of qualified sex therapist. That's okay, too!
I wish you the very best!
Please remember to click the green accept button. Feel free to continue the discussion; my goal is to get you the best answers possible. Bonuses are always appreciated! If I can be of further help with any issue, just put "for Dr. Mark" in the front of your new question, and I'll be the one to answer it. All the best, XXXXX XXXXX