Wants Her Ass Open

Aug 112002
 

My girlfriend and I love your book, love your movies and love anal sex. We’ve been fascinated by the ability of some porn stars to hold their anus open after having anal sex. My girlfriend would really like to be able to do that I would love for her to. Are there exercises she can do to achieve this? How can she learn to stay open after we have anal sex?

–Wants Her Ass Open

In the adult industry, the post-fucking state of openness of an ass which you refer to is called “the gape,” as in the popular vid series Planet of the Gapes. People write to me about seeing the gape in porn videos all the time, but usually it’s in fear. In other words, most folks see a nice, wide open ass and panic; they think that once they have anal sex, their ass will end up like a giant pink hole, they’ll lose control of their bowel movements, and the anal sphincter muscles will forever stay open. Of course, this isn’t the case. I often reassure people that what they are seeing is the ass “at play” — it’s just had something quite big pounding away at it, so it’s naturally very relaxed, aroused, and ajar. If you saw the same asshole “at rest,” it would be small, closed, and puckered as usual.

Your question is an interesting one because you and your girlfriend want to achieve the gape, whereas most folks are freaked out by it. In my experience, some women gape quite easily, others gape only after a prolonged intense assfucking, and others rarely if ever get a gape going. Some of it is pure chance; it has to do with how the body responds to penetration, and in particular how the ass behaves after prolonged stimulation. I don’t think there are any exercises your girlfriend can do to improve her chances of gaping. But she may want to try a few tricks to see if they help keep her ass open. After you pull out, she can reach around and spread her ass cheeks with both hands, which will give the illusion of an open ass. Have her bear down slightly; this may loosen the sphincter muscles and keep them from closing back to their puckered state. You may also want to try putting a butt plug with a wide neck in her ass; this helps relax and open the muscles. The best you can do is practice, and see what works best for both of you.

Anal Chicken

May 282002
 

My husband and I want to try out anal sex really bad, but my problem is the pain — I know it’s not supposed to hurt, but it does. I keep telling him that missionary position is not the best for our first try. Is there another position you recommend? I really want to give this to him, but I am still very nervous. I have tried to relax, but nothing seems to work. I’m thinking I need a lube that desensitizes the area. I know if I can find the right kind of numbing agent, then I will do just fine. Do you know of any?

–Anal Chicken

You admitted being nervous about getting fucked in the ass, which is very common, but my question is: do you really want to do it? I sense a lot of reservation in your letter, and I am concerned that your fear and anxiety aren’t the only things holding you back. Your desire for this must absolutely be there (not just your husband’s), otherwise it’s not going to work, and it will continue to hurt. You are right that it is not supposed to hurt, and pain can be the result of many things: hesitation on your part; not being relaxed; not enough foreplay and warm up; not enough lube. You need to take it slow, and have him open your ass with fingers or small toys before he even attempts to put his cock in there.

As for positions, if missionary isn’t working for you, trust your instincts. Maybe you should get on top, so you can control the depth of penetration, the speed, and you can move your body to get the best angle. Or you could try doggie style, but make sure he doesn’t thrust all the way inside on the first time around.

I cannot recommend any of the de-sensitizing lubricants that are available. Numbing your ass just isn’t a good idea. If you can’t feel anything, you cannot listen to your body’s warning signs that things are going too fast, and you’ll most likely end up with a sore butt the next day. Plus, if it’s numb, you can’t feel all the pleasurable sensations that anal sex can give you, and trust me, you want to feel those.

Mistress Mean

Apr 182002
 


I’m a professional dominatrix, and have several clients into forced feminization and anal play. Some of them have requested that I insert tampons into their (anal) “pussies.” Can this be done safely? I know that there is a risk of toxic shock syndrome when tampons are used vaginally, and I am wondering if it can happen in the ass as well.

–Mistress Mean

Toxic Shock Syndrome is a blood-borne bacterial infection caused by the bacteria Staphylococcus. We most commonly hear about it in relation to using tampons, and symptoms can include fever, chills, vomiting, sore throat, headache and more serious conditions. It is treated with intravenous antibiotics to prevent shock and kidney failure. TSS colonizes skin and mucous membranes, and the rectum is a mucous membrane; however, I had a difficult time locating any documented cases of TSS through the use of tampons anally. Since tampons are used to absorb moisture, it could be uncomfortable and dehydrating at the very least.

I have an easy solution for you. In fact, it’s for anyone who has a client lover who wants something in his or her ass which you know is either unsafe or potentially dangerous (other examples include glass bottles, candles, baseball bats, just to name a few). Find a sex toy with a similar size and feel to the desired (but unadvisable) object. Blindfold your bottom before inserting the toy in his or her ass, and make sure to talk about whatever the fantasized thing is in great detail. If you’re a good Top, you can convince a submissive of almost anything.

Is My Head or My Heart Up My Ass?

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.

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…

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.

Fisting Aficionado

Jun 122001
 


I really want to be able to fist myself! I need your advice on how I can do it. I can fit four fingers up, but cannot get past the knuckles at the end of the fingers, therefore I cannot place my thumb in my ass, and so I can’t fist myself. Please help this poor guy, I am desperate!

—Fisting Aficionado

Is it my imagination or are my readers getting wilder and more adventurous since I started this column two years ago? That just puts a big ol’ grin on my face.

Let’s talk about anal fisting. You definitely want to have an enema before your anal fisting adventure so you can be completely cleaned out. Make sure you have an enema at least several hours before the actual fisting to give your body a chance to recover.

As with any form of extreme penetration, there is no such thing as too much lube when it comes to anal fisting. In fact, one of the tools I recommend is what I fondly call “the lube gun.” You can use either a stainless steel syringe or a disposable plastic one. Fill it with water-based lube, insert it, and shoot lube up your ass. This will lubricate the anal runway ahead of your hand, so you don’t have to re-lube as often. Because pulling your hand all the way out and re-lubing often breaks your momentum, and can make the rectum sore.

Just like you cannot have enough lube, you can also not have enough warm up. Be patient, and let your ass take its time to open up for something bigger. Use butt plugs or dildos which gradually increase in size; put one in and let it stay in to get your ass relaxed and ready for more. Getting past the knuckles is always the trickiest part. You need to be patient, respect the limits of your body, and go as slow as you need to.

I must say, I don’t know many folks who can fist themselves, but more power to you for getting as far as you have already, and, of course, for wanting even more! It seems to me that fisting yourself is all about body position and flexibility. You are ahead of the game if you’ve already gotten four fingers inside. You didn’t mention the position that you’ve been in, but I think that being on all fours or even squatting would work best.

Now, if you find that you just can’t make it happen, remember that there are some cool dildos on the market which are made to look just like a curled fist. You can find them in gay leather shops and catalogs usually. Having an “extra fist” means you can experiment with lots of different positions, and you aren’t limited by the size of your own hand. Please write back to me, and let me know if you finally do go all the way.

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