In the later 70's I met a beautiful young woman (22 yo) on a train who had run away from her husband on their first wedding anniversary. She said she never had an orgasm of any kind. Her father was a famous person, and she had lived in a very repressed household (where masturbating was not allowed). It took 2 bottles of wine, 3 joints, and 6 (six !!) hours of mostly continuous fucking for her to relax enough and have her first orgasm. After that, she was always eager to try again -- and always succeeded. I later had to teach her how to masturbate, since she had never done it in her life.
More recently, I was discreetly approached by an (exceptionally beautiful -- actually, "stunning" would be the right description) married woman with a high-pressure executive job who couldn't have sex with her husband because of his medical conditions, who said she had been masturbating instead for several years, but had become unable to have an orgasm any more. We only tried 4 times, and did not succeed in her having an orgasm, although some of the 2-hour sessions -- mostly spent fucking -- were enjoyable even for her.
This is the first failure I can remember, of the many women who have come to me with some kind of similar situation (no sex for 20 years, no orgasms, etc). My opinion was that she had too many psychological barriers due to her situation, and her fear of being caught (she never even gave me her FIRST name, much less her family name, or where she lived !! ). I also think if we continued longer, and she would have allowed for a wider variety of "kinky" things, we might have found something that really excited her more.
It is also a sad reminder that unlike in movies and TV shows, in the Real World beautiful and smart women do not always have such a wonderful life. I know an even more poignant example, but I'm not prepared to discuss her tragic story now.