Perhaps not all women can because of mental barriers; to some it goes against their views/beliefs and cannot relax and enjoy it. Other times their partners cannot perform it in a way that is pleasurable for both of them. It takes time, some patience and caring for your partner - and some men just care about their own pleasure.
We would only start anal after she had at least one orgasm by other means (manual stimulation, clitorial or vaginal), that way she was relaxed and also anal seemed to be a lot better for her.
She would described it as different from the other 2 (clitorial or vaginal), which means she could orgasm through 3 different ways and all of them were slightly different from each other.
As for cuming, I'm not sure what you're asking - she would orgasm just with anal alone but she did not squirt, for that you have to stimulate a different area.
Best results (with my partner) were when (and this is the only way I can describe it) I tried to stimulate her G-spot doing anal. I don't know if that's possible but that was the angle that produced better results.
Hope it was helpful.
We've played around with each others' butts a while, using small and medium buttplugs to evoke pleasure and intensify vaginal intercourse. Having a small vibrator vaginally has shown to alleviate discomfort if she feels any.
Penetration with my penis is, however, a little different since it is bigger, not nearly as tapered and, no matter how much lube you use (on top of a condom), not as smooth and slippery as a toy. It might hurt after a time for her - probably too soon for either of us to achieve an orgasm - and has to be done very slowly. That's part of the reason we only rarely try actual anal intercourse.
Recently, however, I managed for her to have an orgasm exclusively by anal stimulation with my tongue. First time that this happened to her. I played with and licked her clitoris and labiae before that a little until I noticed she was veeery sensitive in the anal region that night. I like giving oral sex, I don't really care if vaginal or anal.
She'd just taken a shower and was feeling comfortable within her bowels - if your bowels are unsettled or you feel pressure in your final digestive parts it often reduces the pleasure you feel and makes you uneasy about having your partner play with you that way.
The technique is called "rimming"/"rimjob" as you generally lick around the sensitive muscular ring of the sphincter. You can also try to insert your tongue as far as possigle - which is not very far at all - since it is probably the smoothest, best lubed and most flexible thing you're able to insert. Be aware that there might be traces of feces caught in the sphincter's folds, however, depending on time passed since last bowel movement and cleaning.
I figured that I'd try to get her to an anal orgasm and voilà, it took a while and was very stressful for my tongue and neck (weird angles), but I feel that it was worth it. I did use my hands to massage and straddle her buttocks and thighs, but left her vaginal area untouched. That could even have resulted in overstimulation.
I consider this a good sign that she'll be no less willing to work on anal intercourse than before.
hello im a lady who lives on my own i am widowed and i seek sexual satisfaction from masturbation. ive been told to experiment with different toys in different shapes and sizes with flavoured lubricunt, however i personally found myself anally satified with many kitchen appliances such as hand whisks wooden spoons and a part of my blender (not the blade) i was just asking if this is healthy for my anus due to my violent masturbation and age ive been constipated and was wondering if i should seek medical advise from my doctor. if he says i should stop, how do i? its got to an addictive stage of up to 7 times a day. should i be worried about my addiction, afterall i could jam one of my kitchen appliances up my anus. Should i seek profesional help? Yours sincerly, Mildred Taylor