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.

May 162002
 


I recently read that someone made a dildo for anal penetration using pureed mashed potatoes stuffed into a condom which was tied at the end. I would like the instructions for such a device.

–Slick for Starch

Not only is this self-made dildo dangerous for anal play—since there is no flared base or string attached, and a condom isn’t very long, it can easily get lost in your ass—it doesn’t even sound like that much fun. Between the mess it will make putting it together (unless you’ve got some serious kitchen utensils) and the mushy texture it will have when it’s done, I am not very intrigued. Please splurge and buy yourself a dildo or butt plug at a sex toy store. Trust me, you’re worth it.

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.

Apr 042002
 


My partner and I are in a permanent Dominant/submissive relationship, and have been experimenting with anal sex for over two years now. We both get a lot of pleasure out of it. He likes to have me wear a locking harness to keep a butt plug in place while we go out to dinner and a movie. The trouble is, after about an hour, I need to use the restroom and must remove it. What can I do prior to ‘harnessing up’ that will allow me to be able to wear the harness for a longer time? Should I change my diet prior to the excursion?

—Anal Slut in Texas

The amount of time you can wear a butt plug depends upon your personal bathroom schedule, and everyone’s particular time table varies greatly. It sounds like you’re an evening bathroom goer, and that you’ve got a pretty fast metabolism (because shortly after eating, you have to go to the bathroom). In order to prolong your butt plug wearing, I suggest that dinner time be moved. You could eat dinner, wait to have a bowel movement, then get locked in your harness for several hours. Or perhaps you can have an outing with the butt plug in your ass that doesn’t involve food, then, after the scene is over, treat yourself to a meal. If the outing must include dinner, than perhaps your Top should insist that you watch him eat, while you’re limited to water only (sorry to give him tips from my sadistic Top self, but you did ask). If you’re a good girl, maybe he’ll feed you after you’ve held that butt plug in long enough!

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.