Mar 272002
 


I am a straight male who loves to give and receive anal sex. I used to be pretty repressed about it but not anymore. You’ve helped change my attitudes about my sexuality. Are today’s porn starlets being incredibly irresponsible with the amount of ass-to-mouth scenes they perform these days? Are women’s bodies capable of accepting a longer penis inserted into them than men? I see porn stars taking a full eight inches, sometimes more. Is there a difference in our anatomy?

—Anal Porn Watcher

I think that adult film stars need to assess the various health risks of their profession for themselves, and make decisions about what they will and will not do for themselves. Remember that many porn stars are routinely tested for HIV as well as other STDs, so they know their status (in fact, they are tested much more frequently than non-porn stars).

As for the issue of “ass to mouth” which is prevalent is lots of anal porn, it does have some risks. There is bacteria which lives happily in someone’s ass which may not be so content in her mouth, where it could cause an infection. Even if a porn star has a nearly spotless, clean ass, there still can be trace amounts of fecal matter (or blood if there has been any rectal tearing during penetration) which can be transferred from cock to mouth, which could also cause an infection. In general, I don’t recommend folks do it with partners whose sexual history and STD status they do not know. Even for couples who regularly swap bodily fluids, there is still some risk.

In response to your question about length of toys and rectums: there is no difference in the length of a man’s rectum and a woman’s rectum. That part of our anal anatomy is nearly identical. Of course you need to keep in mind that porn stars are professionals: they easily accommodate with toys and cocks in their asses that some of us can only fantasize about!

Mar 132002
 


My girlfriend has just turned 18 years old and loves anal sex, bondage, and water sports. How far can I go in her ass with a dildo and be safe? Once you pass the sphincter muscle, it seems like there is a lot of room. What dangers are there if I piss in her ass while fucking her? I have already pissed in her pussy while fucking her with no problems. How long does it take for chain marks to come off her ass?

—Kinky in NJ

Well, it sounds like you are one busy guy. You’re right that once you get inside the rectum, there is a lot of room; in fact, the rectum is longer than the vagina. You’ve got about 9 1/2-11 inches before you reach the colon, and most dildos aren’t any longer than that. Keep in mind that you should always use a dildo with a flared base to be safe; one without a base could potentially get lost in your girlfriend’s ass—please, no trips to the emergency room which could have been prevented!

As for pissing in her ass, there are a few issues to consider. You need a dependable erection in order to penetrate her ass, and once you’re super hard, you may not be able to pee; some men can’t stay that hard and let it flow. If your dick can stand up and piss, then you’ve got to consider the safe sex issues. As far as bodily fluids go, urine is nearly, but not completely, sterile. Peeing in your sweetheart’s butt is mostly safe for you unless you have any cuts or open sores on your cock. She may want to know that she can get chlamydia, gonorrhea Hepatitis B, cytomegalovirus (CMV), or genital herpes, if these viruses are present in your piss. Unfortunately, there is no research on the transmission of HIV through urine; however, we know that HIV can be present in urine or in urine that contains an amount of blood. If the two of you have been tested for all these diseases and are monogamous, then you should be all right. Remember that whatever you put in a rectum will be instantaneously absorbed into the bloodstream, so she may end up with an upset stomach. You might also consider peeing outside of her ass, which is even safer and still plenty of fun!

Oh, and those chain marks on her ass? Well, it depends on how hard you hit her, how heavy the chain is, how easily her skin bruises, and how quickly her skin heals from marks. I assume you mean metal chains, and if you are hitting her ass with them, be very careful not to hit the base of the spine or her sit bones. You want to concentrate on the fleshy areas only.

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.

Feb 122002
 


My girlfriend has hinted that she wants to try anal sex, but she is too shy to talk about it. She likes me to finger her ass, and she goes crazy when I lick it as well. The problem is that every time I try to penetrate her ass, I lose my erection! I think I must be too nervous or something, but I don’t have this problem when we have vaginal sex. Because of my problem, we have never been successful in anal penetration. I think it takes me such a long time to try and position my dick that I just lose my excitement. Anal sex is one of the most arousing fantasies for me—please help me so I can do it!

—Mr. Softie

If you have a less than solid erection, you can often “stuff it” into her vagina, and, once you’re in, you achieve a full hard on. It’s a little trick which plenty of men do. However, that same shortcut simply does not work with anal penetration. The bottom line is that you need to have a rock hard cock to get it into someone’s ass.

Well, since you have no erectile issues during vaginal sex, then your problem is probably not physical but psychological. My initial question for you is do you have any fears about fucking your girlfriend in the ass? Some men are anxious about hurting their partners. Somewhere in the back of your mind, you may be afraid you’ll cause her pain or perhaps a past lover has told you that you hurt her. If you think you might have this fear, reassure yourself and your girlfriend that you’re going to warm her up, use lots of lube, and go slow, so that it won’t hurt.

Speaking of going slow, it sounds like that may also be part of your problem. You wrote about how much time it takes to get in position, and you may be losing the momentum of the moment. If that is the case, perhaps your girlfriend can stroke your cock as you’re maneuvering it or talk dirty to you to keep the fantasy and the anticipation going while y ou get ready. I’m concerned that you say she’s too shy to talk about anal sex. You may have poor communication both in and out of bed, and that could be contributing to your anxiety or ambivalence about anal sex. Talk to her in a safe, non-threatening aware, share your desires and fears, and agree to work on this issue together.

Jan 172002
 


I’m 36 years old and quite sexually experienced. A few months ago, I met a woman I really like. She is quite inexperienced, but has a hell of an imagination, so it’s working out quite fine. Once, she got really hot for a pair of my shoes. I have lots of shoes, and cannot help buying more. I think she has a shoe fetish because she found a pair of very pointed stilettos of mine, and asked me if I would kick her in the butt with them. I didn’t mind at all, it was great fun actually. How often have you had the urge to give someone a kick in the ass?

But in the heat of the moment, I ended up doing more than kicking her. With some liberal helpings of KY Jelly, she ended up with the best part of my right shoe very deep in her ass. The shoe we used is very long, slim, and pointed, and I am only a size 5 1/2. I was pumping the toe in and out of her in all kinds of positions. By the end, she was riding my shoe, squatting down over my upturned toe. Humping up and down, it went in pretty deep, and she enjoyed it tremendously. She will for sure talk me into fucking her again in the butt with my shoes again, I just know it. She is not interested in being penetrated by the stiletto heel, and I wouldn’t do that anyway because it’s way too sharp. Is there any danger in this kind of anal play? Should I use a condom on the toe of the shoe next time?

—A Kick in The Ass

Usually, I advise people not to use ordinary objects (such as candles, kitchen utensils, wine bottles, or other household items) as sex toys. Because they were designed for other purposes, they can be less than ideal or downright dangerous to put in your own or someone else’s ass. That said, your description of shoe sex was so entertaining and hot that I don’t want to tell you to stop! You’re smart not to try the other end of the shoe, the sharp, pointy heel, because that could definitely cause some damage.

As far as safety goes, you have two options: you can designate one pair of shoes as your butt sex shoes; don’t wear them out, use them only on your girlfriend, and wash them in hot water and antibacterial soap; or if you want to wear the shoes outside the house or use them on different people, then you definitely need to use an extra large condom on the shoe each and every time. As long as the toe of the shoe is smooth (please no bows or buckles!), it should be fine; plus, it definitely can’t get lost in her as long as it’s on my foot. As they say, if the shoe fits…

Jan 062002
 


Is there any way of making my anus more pink or lighter in color? Mine is dark and I hate it—any suggestions?

—Brown Eyed Susan

Believe it or not, your question is a common one. Several people have written to me asking me about skin bleaching in the anal area. First, let me assure you that the way your ass looks now is perfectly normal; in most people, the puckered flesh of the anus is naturally a few shades darker—or a slightly different color—than the rest of their skin. For some people, the contrast is more extreme than others. Remember that everyone’s ass is as unique as a fingerprint.

Is it possible to lighten the skin of the anal opening? Skin bleaching products are used to suppress pigmentation in order to lighten the skin; the most common products contain either hydroquinone, kojic acid or mandelic acid and are available by prescription only; those sold without a prescription tend to be weaker or less effective. Recent studies have shown that azelaic acid, bearberry extract, and licorice extract may also have lightening agents. However, most of these products are not used on genital skin, since it is much more sensitive than other skin. Consult a dermatologist or a cosmetic surgeon about your options, and never attempt to use over-the-counter products on yourself.

As for making it more pink, well that’s a little trickier. The pinkest holes I’ve ever seen are those that have been stroked, licked, and/or fucked til they couldn’t help but blush with contentment (lots of blood rushing to the area helps, too). I support people modifying their bodies in whatever ways they wish in order to feel better about themselves, and so I offer you the information you requested; however, I would also like you to consider why you “hate” your ass so much, and what might be at the root of that particular body issue for you. Coming to terms with your negative feelings about your butt and learning to accept and love your body as it is will be a lot less expensive, less painful and, in the end, seems like the “rosier” option.

Dec 162001
 


Do you do actual demonstrations at your anal sex workshops? Do you take volunteers from the audience? How does it work?

—Willing Anal Volunteer

Most of my workshops are lecture-style only, and do not include live sex acts. However, sometimes I have the opportunity to do a demo, especially when I am presenting to a private members-only group. I don’t travel with a demoee, so I usually ask my hosts to find a suitable bottom for me to play with during my workshop. Lots of people volunteer, and most proclaim that they are wild exhibitionists and experienced anal sex lovers. But, a lot of people don’t take into account what it’s like to be demonstrated on. You have your ass in the air in front of a room full of people which can inhibit even the best exhibitionist. Plus, a demo is not like sex. I am talking, answering questions, and cannot focus 100% of my attention on the bottom, as I would if we were having a one-on-one encounter. So, while I am warming them up, it’s really up to the person to get themselves turned on. I have gotten inside some people’s asses, and realized quickly that nerves and excitement were working against getting something of size in their ass.

Recently at a workshop, the demoee was a cute, curly haired girl who I connected with right off the bat. I ended up fitting most of my hand in her ass, and it was a truly amazing experience. That was the best demo I have ever done, but, more often, I just try to make the best of the situation, and let the bottom take the lead in taking whatever he or she wants in their ass.

Dec 052001
 


After seven years together, my husband and I are just starting out with anal sex and wow is it ever exciting. What a great way to rev up our sex life! I have a question about vaginal infections. Can switching from anal to vaginal penetration during lovemaking lead to vaginal infections? Or are the natural defenses of the vagina generally enough to fight them off? Are there precautionary steps we should start using to reduce or prevent possible infections?

—Curious Canadian

Yes, switching directly from the ass to the vagina is an almost surefire way to get a vaginal infection. Bacteria that lives naturally in the rectum (possibly along with some fecal matter) will be transferred to your pussy which will cause the infection. Since the pussy doesn’t naturally flush itself out, bacteria can set up shop, multiply, and live there until you treat it. Some women get yeast infections, others get bacterial infections like gardinerella.

So, in order to prevent this form of “cross contamination,” you want to take a few precautions. You can use a condom on cocks and sex toys, and put on a new condom when you move from ass to pussy. Or your husband can wash his penis or the sex toy with warm water and an antibacterial soap before switching orifices.

In addition, you should be aware that lube that goes into your ass and drips out of it can make its way to your pussy, which could also cause an infection. I do things to prevent what I call “the drip down effect.” I always have a box of baby wipes handy to make a clean swipe of the area (always swipe front to back). Baby wipes are made for the genital area and much less harsh than other wipes, like Wet Ones. I like the baby wipes that are unscented and alcohol-free; the “baby” smell isn’t erotic for me, and the alcohol-free wipes tend to be gentler on my delicate parts. After sex, I like to pee and wash my pussy with a gentle soap (I like Castille soap) to rinse out any remaining bacteria and prevent a urinary tract infection.

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.