Nov 182001

The past few t imes my wife and I have had anal sex, with her doing the receiving anyway, the act itself went smoothly and pleasurably. However, not a minute after she went to sit on the toilet to clean herself up, she would be struck by a brutal headache. My wife does suffer from the occasional non-sex-related migraine, and her post-anal sex headaches are worse by far. I am convinced that the headaches and the anal sex are somehow related. The easiest fix is to just not have anal sex. My interest in doing it is far outweighed by my not wanting her to suffer. I was wondering what an expert thought, but I’ve been to shy to ask a doctor about it.

—Pain in the Ass?

I, too, suffer from migraines, so I empathize with your wife, because if she’s having a headache worse than a migraine, it must be extremely painful and debilitating. At first glance, the problem seems completely unrelated to anal sex; however, it’s too much of a coincidence since it’s happened several times. Stress and tension can often cause a severe headache, so I have a few theories.

First, while you’re fucking her ass, your wife may be in a position that’s putting undue strain on her neck. I know that sometimes I end up in weird positions — especially when I have my ass in the air and my head down –while buttfucking. Afterwards, I often feel pain in my neck, and that pain could lead to a headache. See how her body is positioned the next time you do it, and make sure her head and neck have plenty of support.

My second theory has to do with her breathing patterns during sex. Many people (me included!) often take very shallow breaths when we get aroused on our way to orgasm. It’s a natural instinct, and one that often gives us a brief “high.” Masturbation guru Dr. Betty Dodson scolded me once that if I am not taking deep breaths, then the blood cannot properly circulate throughout my body during sex. Shallow breaths may cause a quick high, but deep breaths ensure that the blood is flowing and the high people often feel during sex will last throughout the act. If your wife is taking quick breaths, or even holding her breath at some points, she could be depriving her brain of oxygen. This repeated deprivation could cause an intense headache, especially if she’s susceptible to headaches in the first place.

Finally, an answer lies in your question. You may feel shy, but it’s a good idea for her to talk to her doctor about the problem. There may be something else going on, and her body is trying to tell her something.

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.

Nov 052000

My boyfriend and I want to have a three-way experience—he and his best friend (a guy) and me. It has always been a fantasy of mine and he too wants to go through with it. We both swing, so we don’t mind seeing each other with another person. I have never really done this before. I have sucked another guy off while my boyfriend fucked me. However, I have never had two guys penetrate me at the same time, but I really want to do this. I think the idea of having two cocks in me—one in my pussy and one in my ass—would be an unbelievable feeling. However, this seems to be a hard thing to pull off. Do you have any tips on how to make this experience as pleasurable as possible?


Congrats for being able to voice your fantasy out loud and tell your boyfriend. Fantasies can be incredible forces in our lives. When you share a fantasy with your partner, it can bring you closer together — and you can have a hot time in the process!

My first piece of advice is that maybe the two of you should practice some double penetration before you invite your friend over. Use a flexible vibrator or dildo in one of your holes and your boyfriend fills the other. Use lots and lots of lube, go slow, and work your way up to it. Communication is extremely important: you’re testing the limits of your body, so make sure you give your man plenty of feedback about how it feels.

Also realize that some women can easily and comfortably accommodate something of size in their pussy and in their ass. Others will take some effort, with lots of warm-up. But some women may not be able to do it at all, since double penetration really depends on your internal map, and if there’s room for two. You are the one who will know best if it’s possible, so make sure you’re the one who’s in charge and calling the shots. Work out the kinks on your dildo before you plan your threesome.

When you are ready to tackle two flesh cocks at once, use plenty of lube and go really slow. Depending on the size and height of all three of you, some positions will work better than others. You may want to straddle one man and have the other nail you from behind. Try to take one cock about halfway inside your pussy, then angle your body to take the other one in your ass. Both men should start with shallow penetration, so you can get used to the feeling. Remember that porn stars make it look easy in adult movies, but they are seasoned professionals! You may be much more awkward your first time around. Practice makes perfect.

Oct 041999

I want to learn how to make anal love to my girlfriend in such a way that she doesn’t describe it as hurting. Should we try a different position? I want it to feel so good. You are the woman who can help me.

–P.J., Reading, PA

I wish I could hop on a plane and give a personal tutorial to each couple who seeks my advice and guidance. I would arrive with a fully stocked briefcase of lube, latex gloves, condoms, vibrators, and butt plugs. I would let you two get revved up with lots of foreplay, and when you were both ready, I would lead you through anal penetration step by step. Go slow and be gentle. Use lots of lube. Work your way up, beginning with a finger or slim butt plug or dildo. Ask her if she wants clitoral stimulation; some women like to have their clits played with while getting fucked in the ass, others like their partners to concentrate solely on the butt. If she wants your hand or tongue or vibrator on her clit, give it to her. Talk to her the whole time, see what turns her on and what doesn’t work.

When you are ready to fuck her with your cock, find the best position. People always ask me: “What’s the best position for anal sex?” My answer: the one that works for both of you. Missionary position can be great, unless keeping her legs in the air or over your shoulders isn’t comfortable for her. Spooning works if your bodies line up naturally, and the man can get a good angle. If you choose doggie-style (my personal favorite), you can do traditional on-all-fours or do head-down-ass-in-the-air. With doggie-style, you can get a great angle to hit her G-spot, just remember not to go too deep at first. When you first enter her, just put your head inside, stop, and stay where you are. Let her sphincter muscles and anus get used to the feeling. Sometimes, she will actually suck you inside — when we are aroused, our anal canals and rectums start to contract and we can often pull a dick or a toy right in. If she doesn’t suck you in, slide into her very slowly. Many men make the mistake of trying to just shove it in there, and even with the most experienced woman, that just won’t work!

You sound like a very sensitive, caring, anal-sex-loving partner. Have you communicated your desires and concerns to your girlfriend? If she knows that you are caring and promise to be gentle, it will definitely set her mind (and her sphincter muscles!) at ease. You need to emphasize that, as the receptive partner, she’s the one in control of the action: it’s her call on how fast or slow, how deep or not-so-deep, and how much. That’s how I’d handle the situation in person. But, alas, my schedule just doesn’t permit it! Listen to her body and her verbal cues, go slow, and pretend I am there guiding you through it!

Mar 081999

I have just started working as a professional dominatrix, and some of my clients (men) want me to fuck them in the ass with a strap-on. Any advice for a novice in that area?

–Mistress Scarlett, Minneapolis, MN

I am so glad you brought this subject up! I just went to a play party at a small dungeon, and watched an amazing anal scene. A tall, gorgeous dom with fiery red hair and thigh-high PVC boots had her sub on his knees sucking her strap-on cock with his hands tied behind his back. He was a little wisp of a thing, but boy could he fit that big cock in his mouth. After he serviced her, she put him on a bondage table on his back, and basically tied his knees to his chest with some beautiful rope work (red, of course). When she snapped on a latex glove, you could see his eyes get big and glassy. She started working her fingers in his ass, and he squirmed and moaned, but couldn’t go anywhere. She came to the edge of the table and started teasing him with her greased-up cock. He went nuts. Finally, she gave it to him, all eight inches, and he was in heaven.

Now for my advice:

There are so many men out there who enjoy having their assholes stimulated, played with, licked, and penetrated. And, according to lots of men I’ve talked to who are into power play, they especially love to be anally penetrated as part of being dominated, disciplined, even punished or humiliated. In addition to all the nerve endings in the anal area, men have a pleasure spot that’s just too good to overlook — the prostate gland. You can stimulate the prostate with your finger or a dildo.

First, you want to choose a harness that fits you well — the snugger and more secure the better; there are many different kinds (usually made of nylon or leather), and you should definitely try them on in a sex toy store if possible to see which works best for you. For beginning anal players, I would recommend a smaller dildo to start out, but of course, you should find what works best for you and your clients.

As the one doing the penetration, you should also experiment with different positions. I know that the first few times I fucked someone in the ass with a strap-on, I had the person in traditional doggie-style position for several reasons: 1) doggie style gives you a clear view of the butthole, so you can see what the hell you’re doing 2) the position allows for a good angle of penetration, towards the prostate in men (and towards the G-spot in women); and 3) it’s an easy angle to get your balance, establish a rhythm, and get some good thrusting going. So, you may want to start out that way, but you can also try missionary (usually with legs over the shoulders) or man-on-top. Although, as a dominant, I would say that putting him in a position with his ass in the air and head down is probably the best way to go, both practically and for its obvious submissive possibilities.

Anal penetration requires patience, practice and lube, lots of lube. Make sure your bottom is warmed up with lots of teasing. When you start out, you want to go slow and let the butt get used to having something inside it. Always work your way up, adding more lube as you go. When he’s finally read for that big silicone dick, be gentle at first; the more you go easy in the beginning, the more his ass will open up and trust you later on when you really want to ram the guy!

For more on this subject, definitely check out the fabulous video series: Bend Over Boyfriend (Fatale Video) and Bend Over Boyfriend 2: Less Talkin’, More Rockin’ (S.I.R. Productions). There is also a good book called The Strap On Book (Greenery Press) and another called The Ultimate Guide to Dildo and Harness Sex (Cleis Press).