This thread has got me thinking about completely non-orgasmic females. I am not including quickies sex or women too drunk to walk let alone climax or those occasion where the male is too drunk to finish the job, but women who never have experienced orgasm. I remember a lovely woman in her early 20s telling me not to bother licking her, as nothing would come of it. (Sorry for the pun.) She explained that a few years prior she had gone a day-long horse-riding trip that ruined her sexually. She said that she had stupidly dressed sexy, not properly for the long event over rocky terrain, as she wore sexy panties and tight jeans. At the day's end, a huge blister developed right next to her clitoris, which took a long time to vanish.
Where before, she had routinely fingered herself to several orgasm each night before falling asleep; now, she could cum one time out of five tries and never from cunnilingus. Her theory was that she had suffered permanent nerve damage. She still enjoyed intercourse, but she had never orgasmed due to it. Well, one night we tried anal sex; she orgasmed. At the time I had no idea how that was possible. Today, my best guess is that I was indirectly hitting her G-spot through her rectum wall.
The second woman that warned that she never orgasmed from cunnilingus had the tiniest clit I have ever seen. (She was super feminine, long delicate fingers and toes, along with an hourglass figure.) She told me that her masturbation seldom yielded any results and that enough men tried and failed that she assumed that she must be a lesbian. After three or four sex encounters with experienced lesbians, with no better results, she returned heterosexual sex, as she did quite like fucking and sucking cock, even though no orgasms resulted. Of course, I had to try cunnilingus, but I also failed.
One night we were in the 69 position with her on top. I didn't lick her; instead, I gently sucked her labia into my mouth and then released over and over, slowly. She became agitated, so I squeezed her breasts without touching her nipples, which were crazy sensitive. She seemed to be getting close, so I gently licked her clitoral hood, while I alternated squeezing one nipple and then the other. She orgasmed. Big. I then orgasmed. Alas, she later bitched about my orgasm, as she said it broke her string of orgasms (she had three and felt that an even bigger fourth was approaching—until my semen shoot up her throat and out her nose).
So, was it smooth sailing from that point on? No. Getting the precise nipple play timing was critical. One thing I discovered was that if I gave her a through massage before the sex, paying special attention to her thighs, she could achieve orgasm more readily. Also, any amount of alcohol ruined any chance of the big-O happening. (I wonder if pot would have helped.) I had mixed emotions when we broke up, but I was relieved to not to have to work so hard at making her orgasm. In fact, my next girlfriend could orgasm from repeatedly crossing and uncrossing her legs.