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A Guide to Great Anal Sex Pt. 01

My name is Jim. Celeste, my wife of thirty-two years, and I are almost exclusively ass fuckers. Anal intercourse for us is not a once in a while event, but our preferred method of expressing our deep commitment to and love for each other. This is for a very simple reason. Celeste would openly tell you that the weakest orgasm she experiences when I am in her ass is at least twice as intense as the strongest she has when I am in her vagina. If the purpose of intercourse is pleasure, we seek the greatest pleasure possible.

I. Introduction and the female anatomy

With so much misinformation available about anal intercourse, we thought it might be useful to share what we think we know in the hopes that this knowledge will bring the same pleasure to others that it brings us. (I'm writing this so that there will be no confusion about voices, but these lessons are a joint enterprise. The reader will identify easily many of the sections contributed by Celeste).

What follows is not fantasy. There are no sixteen inches penises involved nor women ejaculating across rooms. It is a factual, practical guide, underwritten by the following caveats:

1) This is Celeste and my reality. We have been in a monogamous, and extremely happy, sexual relationship for the entirety of our married life. Your reality may well be different and that may change your experiences.

2) Great sex depends upon both partners being within their comfort zones. If you are uncomfortable with the concept of anal intercourse for any reason-philosophical, religious, or physical-no amount of knowledge is going to bring you pleasure. Don't waste your time reading what follows if this is the case.

3) Neither Celeste nor I are doctors. However, the intensity of the orgasms Celeste experiences during anal intercourse suggest that any woman with either heart or blood pressure issues should consult her physician before experimenting with anything that follows.

4) Never, ever, ever move anything--toy, finger, tongue, or penis—from a woman's anus to her vagina. You're just asking the trouble: STDs and the like.

5) Just to get the subject of elimination out of the way, one obviously doesn't engage in anal intercourse when a bowel movement is impending or your intestines are upset. That aside, elimination isn't an issue. As for cleanliness, a bidet is perfect, but a soapy finger and a detachable shower head work just fine.


The key to great anal sex is knowledge of the complex female anatomy involved. This includes 1) the clitoris; 2) the g-spot and 3) the inner and outer sphincters of the anus.

Women and men know where the pea-shaped protrusion of the clitoris is located and that its stimulation leads to orgasms. What is less well known is that 85% of the clitoris lies under the skin. It has been described as shaped like the wishbone of a turkey (what you used to dry out after Thanksgiving dinner and then snap with a sibling, the holder of the longer piece getting his or her wish) or a horseshoe. The arms of the clitoris arc around the walls of the vagina and curve back toward the anus. A woman can experience swelling, non-orgasmic pleasure simply by having lubricated fingers, hers or yours, gently rub the walls of the vagina, not touching the hood. (Celeste insists that this is the point to say something about fingers. Ladies: if you want to size up a potential lover, forget his butt, eyes, or any fantasy you may have about his penis. Instead, look at his hands; they're a major clue as to how considerate a lover he will be. Neatly trimmed and filed nails may not be a sure sign of a great performer in bed, but rough, dirty, or unclipped nails scream "stay away." Fingers are very important to anal sex and there should be no rough edges to their nails.)

The g-spot is more controversial; some doubt its actual existence. Celeste and I both think she has one, located about two inches into the vagina on the front wall. It is a small, spongy area, the stimulation of which heightens her pleasure. Constant direct pressure on it, combined with clitoral stimulation, can lead to her ejaculating.

Finally, it is critical to understand the sphincters, a pair of muscles lying just inside the anal opening. The human body contains more than fifty pairs of these. One set, for example, make it impossible to breathe and swallow at the same and another how we blink our eyes. Although it is no more alluring than the image of a wishbone, think of the anal sphincters as two miniature rubber bands lying one atop the other. The critical piece of knowledge is that the outer sphincter is a voluntary muscle. Both men and women can control it by simple contractions. It is the inner sphincter that causes problems, and pain, because it is an involuntary muscle that has to be trained to relax. (Much more on this in a subsequent lesson). The furrow between the outer and inner sphincter is also important. Its stimulation seems to produce significant quantities of oxytocins in Celeste, a chemical release that heightens feelings of relaxation and well-being in the brain.

Great orgasms for Celeste result from the simultaneous stimulation of 1) the head of her clitoris, 2) the end tips of her clitoris located near the anus, 3) her g-spot, and 4) the furrow between her inner and outer sphincter. The most intense orgasm she can achieve comes when she lies on her side with her pointer finger pressing against her g-spot while she strokes her clitoris with her thumb and I massage the half of the sphincter furrow closest to her vagina with a well-lubricated (and warmed) pointer finger. This simultaneously stimulates all four key components giving her sexual pleasure that is obviously impossible during vaginal intercourse. After only a brief period, her body almost seems to levitate off the bed, slam down into it as her orgasm occurs (my finger can feel the powerful vaginal contractions that occur) and she screams into her pillow.

Skeptics are invited to try this for themselves, but partners should discuss the intensity of the orgasm that may occur in advance so that there will be no surprises. You should also know that intensity does not equal pleasure. Celeste only occasionally wants me to use my finger. The experience, she says, "is like being hit with a stun gun." She much prefers the use of my tongue or penis in her ass. (More on this in another lesson).

Finally, Celeste asks that we include brief mention of what she calls "the world's best sleeping pill" here. This consists of my gently massaging of the half of the semi-circle of her sphincter furrow lying furthest from her vagina without any other touching on the part of either of us. That releases oxytocins without sexual arousal. When I do this, I can actually feel her body relax, her muscles unwind, and hear the beginnings of deep rhythmic breathing. If I do it longer enough, she frequently falls sound asleep. Even if you have no interest in anal intercourse, you should try this relaxation exercise.

II. Training for anal intercourse (to follow shortly).

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