I am 61 and dating a wonderful woman of 55. Our sex life is phenomenal. The chemistry between us makes us both feel like teenagers again. The only problem is her failure to achieve orgasm.

According to her, this has been a problem with her for all of her adult life, not just with me. The only way that she has been able to achieve orgasm (and it's very, very infrequently) is after I ejaculate inside of her, she lays on her stomach, legs together and my stimulating her digitally. Once, I was able to bring her to orgasm by massaging her G spot while, at the same time, using a small vibrator on her clitoris. We have made love countless times and she has only been able to "get there" twice! She gets right to the brink, tries and tries and then loses it. This is extremely frustrating not only to her but to me as well as I really want to please her. Any suggestions would be most helpful!

That she can have orgasms, even rarely, is a good start. Has she ever tried masturbating, either with her hand or a vibrator? Sometimes a woman can teach herself exactly what she needs to have an orgasm and then, maybe, transfer that knowledge to her partner. I say maybe because some women need to concentrate so much in order to have an orgasm that having a partner with her is too much of a distraction. The manner in which she does have orgasms indicates that possibility, since she has her head down and her legs together. She probably feels too vulnerable lying on her back with her legs spread. Have you ever tried masturbating her while she was partially dressed, say with a robe or negligee, maybe even with panties on. If she’s more comfortable covered up, but can have orgasms, that would be better than nothing.
You should also know that some women reach a plateau in their arousal. Then there’s a pause and only a while later can they begin to grow more aroused, sufficiently to have an orgasm. Perhaps she’s telling you to stop when she feels she’s “losing it” but if you continued to stimulate her clitoris, she might be able to become more aroused again. And if she always requires the stronger sensations of a vibrator on her clitoris, then use one. In fact, be aware that the ones that are plugged into the wall offer stronger sensations than the battery operated ones, so you might want to try different varieties.