Can't orgasm

I can't decide where to post this, so this might be ok. When I was in grad school, I met a cute gal and we became friends. I was very blatant back then, and soon proposed an afternoon tryst. She said that she was not able to have orgasms, so didn't think it would be such a fun time. I convinced her that I'd love to have the challenge of helping her achieve orgasm and she agreed. This all sounds so strange as I am writing it now, but it is absolutely true. I met her at her apt, and we were quickly naked and in her bed. Over the next hour or more, I performed numerous erotic activities on her . She DID seem to be responding positively, but not to the level of orgasm or even near orgasm. I licked and pushed and poked and sucked and rubbed and wore myself out until it actually seemed that it just was NOT going to happen. She even had a vibrator which didn't make it happen...........I should have known that since she had obviously tried it herself. Slow, fast, hard, soft, wet, dry..........I'm telling you, nothing was successful. Now, many years later, I wonder if she might have responded to an anal approach. Rimming or a finger or fingers, or an enema or maybe even some pee play. I'd love to give it another try, but it wouldn't be vanilla this time. This person was attractive, and had a very nice body, with very attractive breasts, and a medium trimmed bush. I hope she solved her problem with achieving orgasms, but while I saw her a few more times at school, we never "tried" again, and I can't even remember her name.

As you alluded too, her "buttons" must have been well hidden.

I so enjoy taking the time to discover woman's pleasure points all over her body.

WOW. A challenge. Must have been fun trying 😃

My poor sub would sympathize with you. My buttons seem to be in some foreign language that were not translated very well. The buttons are there but they are just not working together. It has taken some time to get things figured out so that I can orgasm.