Mr. Softie

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.

A Kick in The Ass

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…

Brown Eyed Susan

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.

Willing Anal Volunteer

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.

Curious Canadian

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.

Pain in the Ass?

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.

Frustrated in Florida

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.

Martha Stewart Up My Ass

Oct 102001
 


I am interested to know: is it safe to squirt milk up your ass using an ejaculating dildo and then shoot it out your ass again? Is it safe to stick candles up your ass? If so, how many?
—Martha Stewart Up My Ass

It sounds like you’ve been spending a little too much time at the crafts center. Lots of people enjoy using ejaculating dildos in their asses, and I know that some of these squirting dongs have a “recipe” for homemade ejaculate right on the box (which usually consists of condensed milk). Keep in mind that whatever you shoot up your ass can be directly absorbed by your bloodstream, and can potentially make you sick, which is why I never recommend exotic enemas that contain anything beyond plain warm water. So, I say, use plain warm water to be safe; it doesn’t offer the same kind of spooging visual, but it does feel the same.

As for your question about candles up the ass, it reminds me of a series of pictures by fetish photographer Richard Kern of women with lit candles in their bums. While the shots were clever, they were ultimately done for art’s sake, and not really something I can give the thumbs up to for the average person. Candles do not have a flared base, and there is a danger of having one get lost in your ass, unless it’s extremely long. But more importantly, they are hard and waxy, and who wants that in your ass when you can have a flexible, smooth butt plug or dildo that will feel much better and won’t have you shitting out wax shavings afterward?

Short and Thick in Iowa

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.

Pleased As Piss

Sep 082001
 


I recently read one of your Anal Advisor columns where a reader had a question about urine enemas. A few years ago, I met this young woman in her late twenties who was totally uninhibited about sex. Before she met me, she wanted to do many things but her former husband wasn’t as adventurous. Before you knew it, there wasn’t anything that we wouldn’t try at least once.

One evening, we were sitting around drinking beer, and after a while, she wanted to know if I would suck her pussy while she peed. Immediately I was aroused and agreed. She sat back on the recliner, spread her legs, and I covered her pussy with my mouth. After a couple minutes, she started to pee. I thought she would never stop, but I vowed not to spill a drop. When she finished, she then wanted me to urinate in her ass. I had an erection, and after a little lubrication, I was in. She was on her hands and knees with her face down, and after part of my erection subsided, I began to pour inside her. She must have received more than she gave me, but she was moaning with pleasure and wanted me to climax insider her rear. After I peed, the erection came back and we both climaxed. We both thought it was the wildest best sex we ever had. There were not any problems afterwards.

—Pleased As Piss

Thank you so much for sharing that erotic treat with me and all your fellow readers. I love it when I hear such successful true-life anal tales! Several words of caution to all of you out there who are thinking of re-creating Pleased As Piss’s scenario. Remember that any substance you introduce into the rectum will be immediately absorbed into the bloodstream, and that includes anything contained in the urine, like medications, illegal drugs, or alcohol. Also: urine is a bodily fluid which can transmit STDs, Hepatitis, and HIV (if there is any blood in the urine), so please be tested, make sure your partner has been tested, and play safe, okay?

 Older Entries  Newer Entries