I've been fortunate in that I've had the chance to help a few women over the years work from being anorgasmic or having a really hard time having an orgasm (say, taking 30+ minutes, or not having ever had one) to big 'ol rolling multiple orgasms.
I take little or no credit for this: this is a journey the woman has to take, not I.
I have, however, collected some pointers that may help others along this path.
The way I approach it causes some women to get quite angry. I really do want only the best sexual outcomes for all women, but that doesn't stop some people from getting upset anyways. Please, keep hate mail about this essay to yourself. I'll delete it unread.
This essay is from a North American/US perspective, as well as a rather geeky one. It is, of necessity, very sexist. I am male, but I don't see any reason that this advice couldn't be useful to women with female partners.
I don't know whether sharing this essay with the person you're helping is a good idea or not; please do feel free to give me feedback about that, or anything else here, at rlpowell@digitalkingdom.org.
FIXME
In my experience, most women are capable of pretty serious multiple orgasms, acheived easily.
By "most" here I mean "every woman I've spent more than a year of serious relationship time with". I can think of maybe one exception; it was a while ago, so I'm not sure.
By "pretty serious multiple orgasms" I mean a normal sex session including a dozen or so, sometimes all chained together in a nice rolling wave.
By "easily" I mean less than ten minutes, as often as not, to the first orgasm, and the others following pretty easily after that.
I am certain that there are women for whom this journey isn't possible; there is nothing about humans that is absolutely predictable. Maybe I'm just lucky. But I think a lot more women can go there than give themselves credit for it, and I blame our society's shitty attitude towards women's sexuality.
This isn't a sexual technique manual. I'm not going to tell you some exact technique for clitoral stimulation or g-spot rubbing or what have you; that isn't how this works.
Similarily, if your goal is to be able to pick up chicks by bragging about your vast orgasm-inducing skills, this isn't for you.
This essay is about a journey that you take with your partner. It requires kindness, love, and a lot of patience. Months of it.
If you're not up for that, find something else to read.