Feb 202002

My ex-husband was a registered nurse, and he once told me how there is a vein or nerve or something (my memory on this is vague) in the anal/rectal area that, if stimulated too much or incorrectly, can lead to near-instant heart attack. I still don’t know why he told me this, considering he wanted me to let him fuck me in the ass. I don’t know how true that is, because logic would have it there’d be gay men and other sexually adventurous people dropping dead left and right if it was even remotely easy to accidentally “do it wrong” so to speak, and there aren’t. Or maybe there are, and people are just too embarrassed to tell the EMS that their significant other dropped dead during anal sex. Can you tell me if it’s true or not?

—Is My Head or My Heart Up My Ass?

Perhaps you already know the answer to your own question, but I’ve got to go with your head on this one. It’s true that there are many, many nerve endings in the anal canal and rectum. These nerve endings are what make the area so sensitive and responsive to what I call the Holy Anal Trinity: stimulation, vibration, and penetration. If you stimulate someone’s ass incorrectly (for example, you don’t use enough lube or you don’t do enough warm up), you can cause discomfort, pain, and possibly tearing of the delicate rectal lining. As for over-stimulation, that might lead to feeling sore or just plain worn out. But neither will lead to an instant heart attack. Doing someone’s ass in just the right way can increase the heart rate and really get the blood pumping through someone’s veins, and it’s as safe as a low-impact aerobics class.

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.

Nov 072001

My girlfriend had recently asked me to have anal sex with her since we had never done it before. I complied, and after two tries (on separate occasions), we succeeded. We enjoyed it so much that we attempted it twice more with success. But we can’t do it anymore. We’ve tried, but we haven’t been able to do it for months. I am supportive as I can be. I give her control, soothe and relax her, question, encourage. But lately she says I have been hurting her. She says I get stuck just after my head goes in, and she can’t continue. The first time we went at it slowly, but near our climaxes, we started to really go at it, and she took all of it in. I have suggested some form of foreplay, but she refuses. She says it is all penis or nothing at all. Please help!

—Frustrated in Florida

You are absolutely doing the right thing by giving your girlfriend control and warming her up. Her insistence that it’s all or nothing just isn’t realistic, and you need to somehow make her see that. Remind her that the ass is not like the pussy: it requires a lot more delicate handling and more foreplay before she can relax it enough to make penetration comfortable and pleasurable. Licking her ass, penetrating with your fingers, or playing with a small butt plug, dildo, or vibrating toy are all good ways to get her ass ready for your cock; of course, remember to use plenty of lube! As for her theory that you are “getting stuck” after the head of your cock goes in, again, with a gradual progression to penetration, her ass will feel more relaxed and open. Because it is the head of your cock she complains about, it sounds like her sphincter muscles aren’t relaxed enough to accommodate your dick. With more warm up, she’ll be more aroused and it should feel much better.

Mar 222001

It’s wonderful that you are so pro-anally inclined. I am a connoisseur of fine posteriors (my wife’s being on top of the list — sorry, don’t feel bad!). We watched your video,
The Ultimate Guide to Anal Sex for Women, and enjoyed it very much. As I was trying to coax my wife into the act, somehow, she tightened up and it became a painful ordeal. We’ve had anal sex before, and she enjoys plugs in her butt when we are having vaginal sex. But she can’t take my turgid member as frequently as I would like.

—Help My Turgid Member

Glad to hear that you worship your wife’s ass. Now, you need to take a little extra care so that both of you can enjoy anal sex. First of all, if she’s experiencing pain during penetration, there may be several different causes. In general, you need to concentrate on giving her a lot of foreplay before you move on to putting your dick in her ass. Use your fingers, then a dildo smaller than your dick, and let her get used to that first. Go slow, and make sure everything feels good to her before graduating to more fingers or a bigger toy. If she experiences discomfort or pain, there may be too much friction. Add some more lube, and see if it feels better when you slide back in. Or you could stop the movement of your finger or the toy, but stay inside; see if the pain subsides. If she’s still hurting, stop penetration altogether and focus on more external stimulation — a hand job, oral sex, more foreplay.

Let her know that she’s the one in control of the situation, and if she needs to, stop the activity altogether. She needs to relax, take some deep breaths, listen to her body, and tell you when she’s ready. After she is warmed-up and ready for your cock, lubricate your turgid member and re-lube her ass. Place your cock at her anal opening and hold it with your hand to help you guide it. Now, you have a few options:

  1. Have her move her body toward your cock (forward or backward depending on your positions), while you guide it inside.
  2. Rub your cock against her opening. This external stimulation should relax the anus. As the sphincter muscles contract, the opening appears to “wink” at you. As it winks open, take the opportunity to slide in.
  3. Press your cock against her opening and gently push against it (she may want to either relax or bear down in order to let you inside).
  4. Penetrate her ass with your finger, withdraw it, and while her anus is open, gently insert your penis.

Have her stimulate her clit as you penetrate her. This will relax and arouse her, making penetration easier. Deep breathing will help her relax and concentrate on opening her ass to you as well as circulating blood to her genitals. (Taking shallow breaths tightens the muscles and inhibits the engorgement process.) If you’re having trouble hitting your intended target (hey, those two holes are close together and it’s slippery with all that lube), have her wrap her fingers around the head of your cock and help to guide you inside her ass.

When you first get inside her ass, don’t go too deep. Again, you want to give her ass an opportunity to get used to your penis. Keep your movements slow, gentle, and subtle at first. When she’s ready, you can venture farther inside and start some slow thrusting. She should tell you if she wants you to go deeper or faster or both. Then, it’s simply a matter of exploring what feels good for both of you.

Feb 232001

My boyfriend and I have been exploring anal sex together, and it’s been really great. We have come together, and it is totally awesome. A couple of times, I have come before him, and my insides feel as though he is doing damage. If I come before my husband does during anal, why is it that it hurts for him to continue thrusting to his climax? It is really a mood breaker for us both, especially if he hasn’t come yet. It’s like I want his cock out of me right that very minute. What can I do (besides not coming) to maintain the comfort and pleasure waiting for him to shoot his load?

—Early Cummer

I get so many letters about people being shy or scared about anal sex or having trouble making it work. Every woman should be so lucky to have your problem!

One explanation for this feeling is that your ass, like your pussy, has contractions during orgasm. After you climax, all the blood that rushed to your genital area disperses, and your ass returns to its non-aroused state (which doesn’t want a cock inside it).

Well, I’ve have first-hand experience with your particular dilemma; I too sometimes come first and find it difficult to go on. So, what can you do about it? Well, you already identified one option, which is to delay your orgasm until after his climax. That way, you extend your pleasure for even longer, and don’t have any discomfort. But, you indicated that you want another strategy. Well, one thing to consider is, after you come, have him slow down his movement or even stop thrusting, but still stay in your ass. Take a few minutes to recover from your mind-blowing orgasm, then concentrate on relaxing your ass and taking lots of deep breaths. Keep your mind on the pleasure and not on the fear that he might be “doing damage,” which will definitely help you relax. To extend your arousal, play with your pussy and clit, and have him slowly resume his in-and-out. Continue to breath deeply, work your clit, and relax your ass. As he pumps your ass, talk to him and let him know how it feels. Hopefully, you can have a second orgasm in the process!

Jun 252000

Yesterday, my lover and I settled down to watch your video (loved it!). We played during the video, and the idea was that I would take her strap on anally. But a strange thing happened. When she inserted a lubed, gloved finger into my butt, I felt an intense burning sensation. After a few minutes, I had to ask that we change the scene. (I wound up giving her a blow job, instead. [Happy dance!])

That’s never happened before, that burning sensation. I can still feel it a little bit now, twelve hours later. I’ve taken things before, like my own fingers, and a medium sized butt plug. Once, a guy even inserted a finger completely into me without lube, and that didn’t hurt. But for some reason, yesterday I got a really intense burning sensation.

The lube we used was Eros lube, and it was a latex glove. I know I don’t have a latex allergy, at least not a system wide one, because I work as an EMT and use latex gloves every day. I also used to cover one of my toys with a latex condom before inserting it (that goes back to when I was fourteen, though). I don’t know what happened. We were so in the mood, too!

Have you ever encountered a similar situation? If so, what was the problem, and how did it get fixed?


Hmmm. It sucks that you were so inspired by my video, but your anal play was a bust! I have a few theories about what might be going on. First, you probably do not have a latex allergy since, as you say, you’re an EMT and you’d know it by now. But have you considered that you may have had an allergic reaction to the lube? Different people have different sensitivities to lubricants; you may want to try a water based lubricant (since Eros, the one you tried, is silicone-based) to see if it makes a difference.

If it’s not the lube, it may be some kind of anal ailment. Hemorrhoids, anal fissures, even a minute tear in the delicate lining of the rectum can cause itching, irritation, burning, or pain. In that case, give your ass a vacation from butt play for about a week, then try it again. If your burning persists, you should see a doctor, because it may be a symptom which requires more extensive treatment (besides just giving your ass a break).

Now, there’s one other possible explanation: your ass just didn’t want to be fucked that night and the “burning” was a form of pain. In other words, sometimes we register pain in different ways: as soreness, as tightness, and, in some cases, as burning. Remember that our butts can be sort of finicky, and we need to respect them. I am glad that you stopped the scene and moved on to something else — listening to your body is so important! There are times when no matter how much you’ve prepared, no matter how much warm up, no matter how much you want it, your ass just won’t cooperate. Sometimes, there are issues or anxieties your haven’t resolved and those psychological issues are manifesting themselves on a physical level. Or you could have been particularly stressed out about something entirely different, but the stress affected your ass. Or, your ass just didn’t want to go there, for no explainable reason.

I hope I have given you some options to explore — good luck next time!

Mar 312000

My boyfriend and I have tried anal sex a couple of times, and each time it was very uncomfortable. I know anal sex isn’t supposed to hurt (and when we try, it usually doesn’t), but I don’t like the way my ass feels — like having to go to the bathroom really bad. Do all people feel this during anal sex, and is there a way to do it without the discomfort? Although I am not opposed to anal sex, I do not find it nearly as stimulating as vaginal sex. Is it possible that my state of mind affects the whole anal sex experience?


I am so glad you wrote to me because your questions and concerns are some of the most popular I receive via mail, on my web site, and at my anal sex workshops. You are absolutely right that anal sex is not supposed to hurt, and if it does, that’s your body’s way of telling you, “This isn’t working right now!” If you feel pain, you should always listen to your body and stop. Your overall arousal, plenty of warm up and foreplay, lots of lube, deep breathing, and relaxation can all help counter pain and turn it into pleasure (which, of course, is what we all want out of anal sex!). I realize that there is a fine line sometimes between pain and discomfort, and each person is different. You need to judge for yourself where that line is.

Your letter indicates that it’s not pain you are feeling, but discomfort. Let me say right off the bat that discomfort is common, especially to anal sex beginners. One of the reasons you, and many first-timer anal receivers, may experience discomfort is simply because your body is experiencing something new. Many people tell me they have the urge to have a bowel movement during anal sex; well, I recommend you stop and go to the bathroom. You may, in fact, have to go. But it’s more likely that your body is just a little confused. Our rectums are used to expelling things, so when the rectum feels something inside, it sends a signal to the brain to shit it out, which is what it normally does.

The next time you feel like you have to have a bowel movement, I recommend you take several deep breaths, relax, and let your ass get used to whatever is inside it. Make sure that the finger, sex toy, or penis inside you stays put and doesn’t make any sudden movements. Chances are after you relax, that initial feeling will subside, and you can progress onto anal pleasure. Remember too that the more you practice anal penetration — with lube and warm up — the more your ass will get used to having things inside it, and will respond with less confusion and more pleasure.

In the end of your letter, you raised another important issue which is how your ambivalent feelings about anal sex may be affecting your experience of it. Your point is a good one: if you aren’t whole heartedly gung ho to get your ass fucked, those emotional and psychological feelings will absolutely have an impact on your physical experience. Desire is a key ingredient to hot, satisfying anal sex, and if it’s missing, you can experience tension, discomfort, and pain. You may be harboring some unresolved issues about anal sex. Most of us have grown up with myths and misinformation about this taboo subject: it’s dirty; it’s not normal; it will cause irreparable damage. Sometimes simply getting correct information (like in my book The Ultimate Guide to Anal Sex for Women and Jack Morin’s Anal Pleasure and Health) can counteract any negative feelings.

Now, there is also the possibility that you aren’t a backdoor girl, anal sex just isn’t for you, and you should respect your own desires. It would make this backdoor girl sad, but to each her own!

Mar 122000

This is a comment about advice written in one of your columns. Kimberly of Spokane, Washington described unbearable pain in spite of her interest and best efforts. Your advice gave the impression that it was her attitude that caused her pain and lack of success. Nowhere was it suggested that she seek proper medical attention from a doctor of proctologist to examine her for organic problems such as an anal fissure or hemorrhoids. Either could render the best intentions, exercise, and lubrication useless in avoiding excruciating pain.

–Steven Wells, San Jose, CA

Thank you for your letter, and your point is well taken. Kimberly’s question about pain during anal sex is representative of so many letters I receive which is why I chose to answer it. When people experience pain during anal sex, it can be attributed to so many different sources: stress and tension of the sphincter muscles, anus, and rectum; a lack of sufficient lubrication and/or warm up; fear, anxiety, or other unresolved emotional or psychological issues around anal sex; or a lack of desire to be doing it in the first place. Those were the issues I focused on in my response to Kimberly.

Of course, the pain some people experience (including Kimberly) could be the result of untreated anal fissures or hemorrhoids which can be aggravated and irritated by anal penetration. Everyone should listen to their bodies, use common sense when it comes to their health, and see a doctor regularly.

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!

Jun 121999

Help! Buttfucking hurts unbearably! It didn’t hurt so bad the first couple of years, but now, 5 years later, it does. It has never been my favorite thing, but it is my partner’s. He feels deprived and almost desperate. We’ve tried Anal-Ease and Anal Easy, but no luck! There must be something a girl can try. Could I use OraGel? Could I stretch my anus by using butt plugs daily? Would stretching exercises work? Please help!

–Kimberly, Spokane, WA

There are so many elements which you need to have a pleasurable, pain-free anal sex experience: lots of foreplay and warm-up, plenty of lubrication, and communication and trust between you and your partner. Anal sex should never, ever be painful. If it hurts, stop. Pain is your body’s way of telling you that whatever you’re doing isn’t working. You should always listen to your body. Your butthole knows what is best for you. At the first sign of pain, you may want to stop all activity or simply slow it down: maybe use one finger only, change to a smaller butt plug, decrease the depth of penetration, or switch to external anal stimulation only. Work your way back up, but never force anything. Go as slow as you need to, continue to add more lube, and talk to your partner so he knows exactly what does and doesn’t feel good.

I’d also like to address your mention of using products like “Anal Ease” or even OraGel. Anal Ease is the brand name of a lubricant (of which there are several) marketed for anal sex which contains a numbing agent. I absolutely do not recommend using products like Anal Ease ever. Because they have the effect of numbing your anal area, you cannot feel your ass literally and you are in danger of hurting yourself. Using products like these often lead people to go farther than they normally would, take something bigger in their ass than they should and the result is a sore ass, possible tearing and damage to the delicate lining of the anal canal and rectum, and pain after the fact that isn’t exactly going to want to make you rush right out and try anal sex again. There are plenty of great water-based lubricants that are thick and work well for anal sex (like I-D, Maximus, and ForPlay Lube de Luxe Cream), so use one of those. As for the OraGel, common sense and warnings on the label should let you know the answer: no. Just don’t go there.

Using butt plugs on a daily basis is a good way to get your butt used to having something inside it. Butt plugs don’t actually “stretch” your butt; they simply help you learn to relax your pelvic and sphincter muscles. In terms of exercises, many women find that Kegel exercises (which exercise your PC muscles) are very helpful. In order to locate your PC muscles, pretend that you are trying to stop peeing (or while you are peeing, you can actually stop the flow of urine). The muscles you contract to stop the flow are your PC muscles. If you put your finger on your perineum — the area between your vagina and your anus — while you do this exercise, you can feel the contractions.

Kegel exercises (named for the scientist who studied PC muscles and popularized the theory of exercising them) can help you to become more aware of your sphincter and PC muscles and learn to control and strengthen them. They will help you get in tune with the feelings in your pelvic area, increasing your sensitivity and responsiveness. The exercises will also tone the pelvic muscles, making them more flexible and more receptive to pleasurable sensations; when you exercise the PC muscles, other muscles in the area also are exercised and strengthened.

Women who regularly exercise their PC and pelvic muscles report some very positive benefits: heightened pelvic sensations and greater anal sensitivity; increased pleasure during clitoral stimulation, vaginal and anal penetration; more control over orgasms; and better, more intense orgasms. For more information on Kegel exercises, check out Anal Pleasure and Health by Jack Morin and The Complete Guide to Safer Sex from the Institute for Advanced Study of Human Sexuality. There is also a masturbation tool called the Kegelcisor, designed like a barbell for your pussy, which works wonders on those muscles!

But there is another crucial ingredient to great anal sex, the most important one — which may be missing for you, according to your letter: desire. You really have to want to be fucked in the ass.

First, you may want to think about why you don’t enjoy anal sex. Many people have fears and anxieties which, when kept to themselves, can result in tension and a butthole that just won’t let anything inside. Meditate on your feelings about and associations with anal sex, your past experiences with buttfucking, what you liked and disliked about it. Share your thoughts with your partner — sometimes talking about things can help you assuage your fears and relax. If you come to the conclusion that you don’t want to do it, then don’t do it. All the exercises, butt plugs, and lube in the world won’t do a damn thing if your heart’s not in it.