Jul 132003

My boyfriend and I love anal sex. When he penetrates me, I come and squirt all over the place. It’s not pee, but I definitely soak the bed. We both love it, but is this normal or am I special?

–Gushing Girl

Congratulations — it sounds like you are a female ejaculator! Many women have the ability to ejaculate either through direct or indirect stimulation of the G-spot, also known as the urethral sponge. The urethral sponge sits around the urethra, and its paraurethral glands produce ejaculatory fluid which can comes out of the urethra (which is why many people mistake it for urine). You can definitely achieve indirect G-spot stimulation through anal penetration, especially during certain positions which angle the body toward that all important spot, like doggie style with your head down and ass in the air. You and your guy have obviously found the magic spot, so keep on doing what you’re doing. Women who ejaculate often soak the bed, so I suggest you put down a towel or an absorbent bed pad before you get going.

Jun 072002

My girlfriend and I have been having anal sex for about four or five months. In fact, the first time I penetrated her was anally. After that, it’s been a once-in-a-while ritual where I get to have the pleasure of making love to her sexy ass. I enjoy it very much and she doesn’t mind letting me have my way, even though she says she receives little to no pleasure from it. We use plenty of lube and always warm up with shallow and slow penetration, deep breathing and lots of communication. We now do it now once every three weeks to a month, which is kind of my problem. I’d like to do it more often, but not too much.

I have two questions for you: How much anal sex do you think is healthy for a couple that wants to have a nice balance between the three major forms of sex (oral, vaginal and anal)? What kind of ways can I pleasure her when I do her in the ass? How can I make her come from anal sex?

–Booty Lover

There is no mathematical equation to determine “a nice balance,” nor is there any common recommendation about how much of one kind of sex a healthy couple should have. Sexuality and our particular practices are extremely unique to the individuals involved, and therefore so are our preferences and how often or little we indulge in them. I say if both you and your wife are content with how much sex you’re having, and the kinds of sex you’re having, then why mess with a good thing?

But it does sound like you’d like to add more anal sex to the menu, and your second question is the key to getting there. Because if you start to give her tremendous pleasure while you’re fucking her in the ass, then chances are she’ll want to do it more often. There are a number of ways to get a woman off while you’re fucking her ass. You can play with her clit while you penetrate her, or if the position you’re in makes that too difficult, encourage her to jerk herself off or even use a small vibrator. Clitoral stimulation combined with anal penetration is one of the ways some women can orgasm. If she likes double penetration, try putting a few fingers in her pussy or a slim dildo while you’re in her ass; this often increases the sensations in both places. Experiment with different positions in order to find her G-spot. Many women experience indirect G-spot stimulation through anal sex. You want to angle fingers, toys, or your cock toward the front of her body to find and stimulate the spot. Also, ask her what she’d like to do to make it feel not just better, but fantastic. Together, you can discover what will turn you both on.

Sep 282001

In one of your columns, regarding dildos and vibrators, you gave the following advice: “Just make sure that the vibrator is long enough like over 7″ for penetration, and, ideally, has a flared base.” While I can say from personal experience that a longer instrument is more satisfactory than a shorter one, real life does not treat you so kindly. My penis is 5 3/4 inches long, and the same in circumference, making it about 1.8 inches thick (when erect). In other words, short and thick. In fact 52 percent of men have an erect penis with a length of less than six inches. Only 4 1/2 percent of men have a penis length of 7 inches or more (My source is The Kinsey Report circa 1950). Therefore, I wonder if you could answer the following questions:

  1. Is a 5 to 6 inch penis too short to give adequate stimulation to your anal partner? Is it long enough to reach and massage the prostate with a male partner? Can it reach and massage the G-spot with a female partner?
  2. If, in fact, it is generally not long enough, are there any positions that are particularly recommended as shortening or compressing the anal channel to bring the sensitive surfaces within reach? Are they different for a male partner than a female partner?

—Short and Thick in Iowa

Well, you’ve obviously done your own research on the subject of anal pleasure, and you’ve given these matters a great deal of thought. While some people, both women and men, prefer a longer object in their asses, others are quite content with a member of your size. It’s really all a matter of individual taste, which is why one person might select a long, slender vibrating anal probe to bring herself to orgasm, but another person might choose something short and fat, like a robust butt plug, to push him over the edge. It just depends what you like.

Know that a 5 or 6 inch penis absolutely can stimulate a person’s ass just fine. Equally important, you can easily reach the prostate gland in men and the G-spot in women, since both “spots” are located just a few inches inside the rectum. In fact, I encourage most men who are using their cocks to stimulate the G-spot not to penetrate fully, since you’ll slide right by the G-spot (the same is true for the prostate).

As for positions, putting the receptive partner in doggie-style position (or what I call modified doggie style, where the head is down and the ass is in the air) can afford you a perfect angle to hit the G spot or the prostate and give you the opportunity for deeper penetration. You cannot actually “compress the anal channel,” but you can get in there deeper at that angle.

As for the differences in male and female anal anatomy, our anatomy is nearly identical except that men have a prostate gland (which can be stimulated through the rectum) and women have a G-spot (which can be directly stimulated through vaginal penetration and indirectly stimulated through anal penetration). Please don’t feel like your cock is inadequate, Short and Thick; as long as you know how to use it, you can bring your partner plenty of pleasure.

Aug 052001

I am in a relationship with woman, and we both want to try anal sex. But I have one concern. I know that it’s going to feel really good for me, because I am a guy, but what will it feel like for her? Do women get off on anal penetration, and if they do, then how exactly? Can my girlfriend come from it?

—What’s In It For Her?

Rest assured that there is plenty in it for her. First, let’s talk about the physical aspects of anal sex. Anorectal anatomy is nearly identical in men and women, and the entire area — the anus, anal canal, and rectum — is extremely rich in nerve endings and sensitive to stimulation of all kinds, including penetration. Because of this level of sensitivity, exploring our asses can bring us incredible sexual pleasure.

The one distinction in men and women’s anal anatomy is that men have a prostate gland, which can be reached and stimulated through the rectum. Although women don’t have a prostate, they do have a G-spot. The G-spot is reached through the front wall of the vagina, but it can also be indirectly stimulated through anal penetration. Since all that separates the rectum and the vagina is a thin membrane, if you angle a finger, toy, or penis toward the front wall of the vagina, women still may experience G-spot stimulation. Many women find that the G-spot stimulation they get from anal sex is one way they can have an orgasm. Another way for her to orgasm is to add clitoral stimulation as you penetrate her. Give her clit some rubbing action or let her jerk herself off with her hand or a vibrator while you do her in the ass, and see what happens.

In addition to the bundle of physical pleasure that anal stimulation brings, there are complex emotional and psychological issues that contribute to the erotic experience. For some people, the idea that anal sex is naughty, forbidden and taboo is very exciting, and adds to their enjoyment of it. For others, the great amount of trust one must have in a partner heightens the physical pleasure; allowing your partner to penetrate you in this special place says, “Here is a delicate part of my body, and I trust you not to hurt me but to make me feel very good.” That power exchange can be very intense for lovers. Anal sex is often represented in popular culture as violent and degrading; however, in reality, it can be extremely intimate, connecting, and even spiritual.

Sep 292000

My husband and I just experienced anal sex. We have tried this adventure before, but it has always been painful to me. Your advice for him to stimulate other areas helped me relax this time. Also, we found the doggie-style/head down/butt up position comfortable for both of us. My husband is an anal sex lover, and now I feel I can fulfill his passions and enjoy the experience myself. Thank you so much for such knowledgeable information and guidance. Now, for my question: does an anal orgasm come with experience, and is it more intense than the vaginal orgasm?

—T. D.

It is letters like yours that make my job so fulfilling! When I know that my work has helped someone experience the mind-blowing pleasures of anal sex, I feel that my mission is accomplished. On to your question about anal orgasms. Women experience pleasure from anal sex is a variety of different ways. The anal area is so rich in nerve endings that stimulating such an erogenous zone could certainly bring you to orgasm. Some women like to combine clitoral stimulation with anal penetration. When I work my clit while my ass is being fucked, and I come, the orgasm definitely feels different than if I was just having clit stimulation. It feels stronger, more intense, and like more of a full-body orgasm, rather than one primarily centered between my legs.

Although we don’t have a prostate gland like men, women do have a G-spot. The G-spot is reached through the front wall of the vagina, but it can also be indirectly stimulated through anal penetration. If you angle a finger, toy, or penis towards the front wall of the vagina, you may experience G-spot stimulation and come that way.

In addition to the bundle of physical pleasure that anal stimulation brings, there are complex emotional and psychological issues which contribute to the erotic experience. For some people, the idea that anal sex is naughty, forbidden and taboo is very exciting, and adds to their enjoyment of it. For me, the amount of trust I must have in my partner heightens my physical pleasure. Anal sex is my way of saying, “Here is a delicate part of my body, and I trust you not to hurt me but to make me feel very good.” That power exchange can be very intense. A world of orgasmic possibilities await you.

Apr 052000

I just wanted to know if a woman actually gets any pleasure out of anal sex or is it just the guy? I’ve buttfucked some women who like it but others think it’s absolutely disgusting.

–Alan, Dubai

I am always slightly surprised by this question when I get it, and my gut response is: do people think that I have devoted my life to anal sex just for my health? Of course it’s pleasurable for me, why would I do it, write about it, talk about it so much if it didn’t bring me mind-blowing orgasms? The myth that women don’t enjoy receiving anal sex and that they just do it to please their partners is particularly prevalent among heterosexuals. Often, when we do hear about women having anal sex, the story goes something like this: the long-term boyfriend begged and begged and finally his girlfriend gave in to his demands. Her boyfriend was pleased, but she didn’t enjoy herself one bit. We never hear stories about women who crave and enjoy anal play or women who initiate anal sex. Author Susan Crain Bakos said, “Buttfucking is seen as the ultimate male sexual fantasy. We, as a culture, don’t understand how much women can like taking it up the ass.” She’s right: there are plenty of women who love buttfucking.

From a purely physical standpoint, the anus, anal canal, and rectum are wonderfully erogenous zones, rich in nerve endings and super-sensitive to stimulation and penetration. At the right angle, many women find that you can indirectly stimulate the G-spot (the spongy tissue around the urethra located on the front wall of the vagina) through anal penetration. G-spot stimulation feels great and even makes some women orgasm.

As I say in the introduction to my book on anal sex:

The first time someone put their finger in my butt, I almost went crazy from the pleasure. The sensations I experienced were so intense, incredible, and heavenly, that it was nearly mind-blowing. I felt high from the experience, and I couldn’t wait to do it again. The first time I put my finger in someone else’s butt, the results were just as fabulous — I felt entrusted with my partner’s deepest vulnerabilities, in awe of the ecstatic pleasure I could give. Each time I could take a little more and give a little more, the more sexually alive and powerful I felt. As I incorporated anal eroticism into my sex life, my sex life became better and better. The sex got hotter, my partners extra adventurous, my orgasms fierce and explosive. The physical sensations were undeniably some of the best I’d ever felt in my life. I confess too that beyond the deep body gratification, the naughtiness of it all really turned me on.

When you add the emotional aspects of anal sex — trust, tasting the forbidden, surrender, submission — to the physical sensations, you’ve got a very powerful sexual experience.