A Guide to Great Anal Sex

Conclusion: Go Pick Apples

Celeste:

We are at the end of the guide. I've volunteered to write a summary of the physical part, how to have great anal sex. Jimmy gets the harder assignment dealing with emotion, why to have great anal sex.

Here's my non-scientific explanation for how anal sex can take a woman to a pleasure point she might not even know existed. The two most erogenous areas in a woman's body are her clitoris and the furrow between her inner and outer sphincters. When they are stimulated simultaneously, they react to each other synergistically, sending pleasure messages to the brain not in a 1+1=2 ratio but as 1+1=4. That's the most basic concept, secret number one.

Armed with this knowledge, perform a simple test on yourself to see if you are receptive to anal sex. No one will ever know that you took it, unless you tell them. It will also be completely painless.

The next time you are in the mood to masturbate, take a pillow, fold it over on itself and slide it under your butt to provide easy access to your hole. Approaching from the rear, take the pointer finger of hand you don't masturbate with, lube it or just spit on it, and insert it into your ass. Slowly and gently push inward until you touch something that feels like a tight little rubber band. That is the outer sphincter that you can control. Push beyond it until you meet resistance. That is the inner sphincter that requires training. Do not push through it. That would be very likely to cause pain, perhaps sharp, shooting pain. Instead, run the ball of your fingertip around in the furrow between your outer and inner sphincter. When your comfortable with the sensation this creates, rest your finger in one spot and press in. I think that this spot should be off to the side, not the point closest to your vagina. That's way too much sensation for me. While continuing to press in, take your other hand and stroke your clit in your favorite way to an orgasm. Now, honestly answer the question of what you felt. If it was just a regular orgasm, you probably are not going to get a great deal of pleasure from anal sex for any number of reasons. If you're like me, however, this exercise will produce a very different experience from just masturbating. I feel a warm glow spreading upward through my body and sense a growing wetness. Then my body starts to tremble. As my orgasm approaches, my hips seem to rise up off the bed and then slam down when it hits. The first contraction is huge, followed by several smaller ones. If your experience is somewhat like mine, you probably will enjoy anal sex.

BTW, a guy can administer exactly the same test to himself the next time he jerks off.

If this test makes you want to go on, it's really only becomes a question of who's going to put what where and when, something Jimmy and I have written about in great detail.

Secret number two flow directly from secret number one. When you encounter the phrase "anal sex is not for everybody," it usually means one of two things. It may mean that you have moral or religious objections to it. In that case, congratulations on having a strong belief system that hopefully brings you happiness and peace of mind. It can, however, also mean that many women are reluctant to endure the pain of the early stages of insertion. Secret number two is that you don't have to penetrate through a woman's inner sphincter to have great anal sex. Frotting and rimming by themselves provide exquisite pleasure for a woman, as rimming does for a man. They should be in any lover's repertoire. I could easily see how anal outercourse and vaginal intercourse would be a perfect combination for many couples. Just never do them in that order in the same session. Never.

If you want to go on to penetration beyond the inner sphincter, reread the section on training and understand what is going to happen.

Do I want you ramming in and out of my ass? Not very often. Can you induce a huge orgasm in me by bottoming out and manhandling (literally) my clit? Yes. The physical sensations produced from this will overwhelm me. But that's not making love, however, that's dominating, possessing, and working out male fantasies.

Great anal sex is the sex of touch, and it requires restraint on the man's part. For us, it's Jimmy lightly running his fingers over my spine and causing goose bumps to break out everywhere as his penis pushes against my g-spot. It's his tongue licking between my inner and outer sphincter and making my body shake. It's him placing the rim of the head of his dick in my furrow, pulsing it but not pushing, and letting me luxuriate in the involuntary contractions that are going to lead me to a beautiful orgasm. It's all of this and so much more.

It turns out that ancient civilizations knew a great deal about gentle anal sex. If you want to learn what they knew, google "tantric anal sex" for explanations. These can be fairly technical and may use confusing Sanskrit terms, but Jennifer Lawless's blog is written in plain English and readable. Be sure not to miss her piece on massaging a man's prostate.

I love Jimmy for many reasons, but one of them is because he practices the anal sex of touch. He knows that he's in the most delicate and sensitive spot in my body because I want him there. He also know these principles for bringing me pleasure and being a great, sensitive, physical lover:

1. 95 times out of a hundred, shallow trumps deep penetration and that I'll tell him when this isn't going to be true. There's nothing deeper in my body than my g-spot that you can touch and bring me additional pleasure.

2. 95 times out of a hundred, slow and gentle thrusting trumps fast and hard.

3. Even better, don't thrust at all. Usually, I want to fuck myself on his dick, not have him fuck me. I know exactly how to shift my hips so that he reaches the magic spots I want to have touched at any particularly moment and he, no matter how considerate he is, can only guess. Here's a guarantee. Let the woman lead and she'll take a lover to new levels of pleasure for himself that make bottoming out totally forgettable.

4. I don't want Jimmy to touch my clit. That's imposing his will on me. Believe me, I know how to bring myself to an orgasm when I want to have one.

5. Many times, however, I don't want to proceed in a straight line from arousal to an orgasm. There's nothing wrong with me or with our relationship. Rather, I want to spend the day on the delicious edge of remembering my last orgasm or anticipating the next. Thinking about the pleasures of anal sex can be as enjoyable, sometimes more enjoyable, than the act itself.

Jimmy's understanding of all this makes him a great lover.

Jim:

We wanted to end this series with how Celeste and my relationship developed because it answers the question of why, not how, we have great anal sex. Unfortunately, it's a saccharine boy meets girls, boy and girl lose each other, boy and girl get back together and ride off into the sunset type story. There is an important lesson in it, however, which is why we wanted to conclude with it.

Celeste and I met during our sophomore year in college when we were in a calculus class together. I was a naïve kid with limited sexual experience. Celeste was a dream to me: bright, witty, and extremely attractive. I pursued her and we started to date very casually. As the sexual revolution was in full swing, these dates frequently ended with her masturbating me and seeing her "own little water fountain" as she called it in action "Oh," she'd say, "I want to feel that." The problem was that she was a good Roman Catholic and I, while not as faithful, also attended church regularly. We both knew that the church refused to sanction the use of birth control devices and so, without telling me, Celeste began the training for anal sex that we have described. You can laugh, but we started ass fucking because we wanted to be good Catholics, not have children, and still enjoy a sexual relationship. It isn't very logical in retrospect, but it made sense at the time.

[Anal sex as a method of birth control is very unreliable. It growing popularity (see part eight) has, however, had an important effect on population growth. This Wednesday, USA Today had a front-page article about how American couples are having fewer babies and at a later age. "Experts" were puzzled by this trend and could not exactly explain it. There probably are complicated economic and social explanations that are more important, but it's also a fact that as more and more couples are discovering the pleasures of ass fucking, fewer babies are being born.]

Eventually, I fumbled and bumbled my way through the introductory phases of anal sex with a very patient Celeste, who put up with many premature ejaculations and other mistakes on my part. Finally, I mastered the two "secrets" and the five rules even though she must have thought, although she never said anything, that I was a slow learner. We went on to have a riotously sensual sophomore year: great, casual anal sex that was non-committal, but pleasurable beyond belief.

Then Celeste left for her junior year abroad and I had the opportunity to "play the field," something I did with great enthusiasm. I went out with a series of girls, most of whom I took to bed, penetrated only as deeply as they wanted, and all of whom experienced intense orgasms that were a new experience for them and provoked two reactions: "I didn't know that was possible" and "let's do it again." But a funny thing happened. The more I anal sex I engaged in, the less pleasure it brought me.

Things came to a head one day in the fraternity house when a friend said to me "Jim, my man, you're becoming a big man on campus. I heard two girls talking at the student union and one said 'You ought to go out on a date with Jim. He really knows how to make a girl feel good. Believe me, I know.'"

Instead of being proud of this reputation, I was devastated. What was I becoming? I thought. I was a dick for hire. I was using girls but they they were also using me. The intensity of the physical pleasure prevented forming any meaningful relations.

So I just stopped going out. I was very discrete, but I just didn't date any more, and went into what friends described as a "monkish phase." That summer I worked construction, prepared an outline for my senior thesis, and kept far away from all things sexual.

In the fall, Celeste came back from Paris and we found unexpectedly ourselves in a seminar entitled: "Books That Shocked the Twentieth Century." One of the texts was D.H. Lawrence's Lady Chatterley's Lover, the story of the affair between a noble woman and her gamekeeper. We discussed it in a Saturday class (that tells you how long ago this was), after which Celeste and I ended up having coffee together. "You know," she said, "Lady Chatterley and Oliver weren't only having a scandalous affair, they were making love through the back door. Remember how much fun that was?" Yielding to temptation, I said "let's go back to my place and remember together." Up we got and headed for my apartment. I remember trying to hold my books in front of me so that nobody could see my erection.

We had gotten about half way across campus when Celeste stopped and said something that literally changed our lives: "You know, Jim (I wasn't Jimmy yet), "we can always fuck, but it's perfect weather for apple picking and we can't always do that. Let's do that instead. Drive over and meet me in an hour." For some reason, I felt a sense of total relief when she said that.

So I went home, got in my ancient Volkswagen bug (the one with the engine in the back and the little lever that opened the reserve gas tank in the ceiling. I loved that car,) and drove over to her place. She came out with a picnic hamper and an empty bushel basket. We drove out to a local orchard and spent the rest of the morning and afternoon picking apples, talking about her time in Paris, having a really nice lunch, and laughing when she stole the ladder and wouldn't give it back while I was up a tree. Then it was back to her apartment and an evening spent coring and pealing apples, milling them, cooking them, adding the sugar and cinnamon, and sealing applesauce in sterilized mason jars for distribution to our friends the next day. When we finished, Celeste gave me a kiss on the cheek and said "that was really fun. See you tomorrow." As I left, I was as happy as I had been in a long time.

The next week we attended a slide show on owls that we both wanted to see, then movies, then dinners, hand holding, and long walks. After about a month, we went to bed together—and the sex was wonderful, as it would have been the Saturday morning of the seminar, but with a profound difference. Now we knew and enjoyed each other on a personal level we never had before. I knew that she had been named for a nurse who saved her grandfather's life during World War I, she that I could do an imitation of Richard Nixon that made her laugh so hard she had to ask me to stop, and thousands of other things. After that, when we did whatever we did in bed or elsewhere, it wasn't blindingly sensual but impersonal sex. We were speaking a language of commitment and that commitment led to love, marriage, and true happiness.

What we realized as we worked on this writing project was that where we began was not where we were ending up. We began wanting to write a guide, to explain our experiences with anal sex, to demystify it and to make its pleasures available to readers. On a that level, we succeeded—or at least many of you have been kind enough to say we did. We've detailed our physical experiences as openly and as honestly as we could. If A does x with B, y is the result.

On a deeper level, however, we've haven't written a guide, we've written a dictionary. It explains ways we express our love, support and commitment for each other through anal sex. Each act has a meaning that we both understand. When I put my tongue in exactly the right spot and Celeste screams into her pillow, I'm saying "I know this makes you happy and because it makes you happy, it makes me happy." When I frot her at night and feel the tension drain out of her body as she drifts off to sleep, I'm saying "I'm glad you're part of my life, thank you for spending the day with me, and I'll be here for you in the morning." When Celeste docks with me and her sphincters begin rhythmically to milk me, she's saying "I love you and I want you to be as happy as I am."

You can and should write your own dictionary, but you have to pick apples first.

At home, we have an old-fashioned hope chest, filled with the mementos of our lives: a football I threw for a winning touchdown in high school, a fulsome newspaper review of Celeste rendition of an show-stopping aria, lots of baby books, and the like. You know what else you would find in that chest carefully wrapped in a blanket from the Grand Canyon hiking trip? The one remaining mason jar of applesauce from the day that changed our lives thirty-five years ago.

A long and happy life to you all.

Celeste and Jim

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