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…

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.

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?

May 192001

Help! Though the internet and your column have proved immeasurably helpful in providing the basic foundation of necessary information needed to explore my outrageously kinky side, I am having a difficult time with one specific area of interest. What are the health risks of pissing in someone’s ass? I have read wonderfully exciting accounts (fictional I’m sure) of this activity and cannot wait to explore it myself. But, I am also aware of the problems that can arise from not being well informed. Please, any help, advice, or referrals you can offer would be greatly appreciated. I promise to share the information with as many people as I can find to ensure that your words of wisdom have maximum benefit amongst the ass master population.

—Ass Master Who Likes Golden Showers

Thanks for sharing a common fantasy I hear about a lot. The first issue you’ve got to tackle is this: can you actually accomplish the act of peeing in someone’s ass? Lots of men find that when they have a rock-solid erection (which makes anal penetration much easier), they can’t piss. They need to soften up a bit so they can release their golden nectar. But depending on your cock, letting your hard-on go down a little may prevent you from penetrating your partner’s ass.

Once you’ve addressed that dilemma, now I can answer your questions about the potential risks. Contrary to popular belief, urine isn’t sterile, but it is very clean as far as bodily fluids go, even cleaner than spit. Peeing on someone or in someone’s ass is pretty low risk for the pisser, unless he has any cuts or open wounds on his cock. For the pissee, being peed on or in can be safe, with a few very big exceptions. Hepatitis B, cytomegalovirus (CMV), the genital herpes virus, chlamydia, and gonorrhea may be present in the urine of a person infected with any of these diseases and can be transmitted through the mucous membrane of the rectum or through any microscopic tears in the anal canal or rectum. There is no research (unfortunately) on HIV being transmitted through urine; however, it is possible for the virus to be present in urine, especially if there is blood in the urine.

Remember that whatever you put in a rectum will be instantaneously absorbed into the bloodstream, so a diluted version may be your best bet. And even so, you may get an upset stomach.

If you aren’t sure about your partner’s sexual history or STD and HIV status or your partner isn’t comfortable with getting your urine in her ass, you may want to consider some alternatives. You could pull out and pee on the outside of her body; there are still risks, but they are relatively low if she has no unbroken skin in the area. Be safe and have fun!

Apr 252001

What STDs can I get from anal sex? Is it imperative that I wear a condom during anal sex to protect myself from disease? Is it dangerous for a woman to get fucked in her vagina after getting fucked in her ass?

—Condom Curious

The American Medical Women’s Association recommends that you and your partner should be tested for HIV 6 months after you or your partner has had sexual contact with a different partner. During that six-month period, you should practice safer sex. You can contract almost any STD, including herpes, gonorrhea, chlamydia, syphilis, and HIV, as well as hepatitis, through unprotected analingus and anal penetration with an infected partner.

To reduce your risk, you should use barriers for analingus (rimming) and condoms for anal penetration. Originally designed for use by dentists as the name indicates, dental dams are squares of latex which safer sex practitioners have coopted for use as oral sex barriers. Because they were not developed with sex in mind, dental dams can be too small and too thick to make them ideal. Glyde Dams are a larger, thinner version designed specifically for oral sex which do the job much better than traditional dental dams. They are available at better sex toy stores. To make your own latex dam, you can cut a non-lubricated condom up one side; these tend to be thinner like the Glydes, which allows both partners more feeling and greater sensitivity. You can also transform a latex glove into a dam: cut the wrist and the fingers off, leaving the thumb intact. Open it up, stick your tongue in the thumb slot, and voila — it’s like a condom for your tongue! This is my favorite kind of a dam because it affords both giver and receiver the highest sensitivity. For obvious reasons, it’s best to use a glove that isn’t powdered or to rinse the powder off before you put your mouth near it. Try putting a dab of lube on the inside and outside of the thumb for even more sensitivity.

Store-bought plastic wrap (like Saran Wrap) is not just for leftovers — it also makes a good barrier for rimming. Plastic wrap is less expensive and easier to find than latex dams, which makes it more convenient. Another advantage: trying wrapping your sweetie’s privates in plastic — think of it as a homemade thong. Then you can go to town without having to hold the dam in place. Safe, hands-free ass licking at last!

Putting a latex glove on your hand for finger fucking protects both you and your partner, especially if you have any cuts, scratches or even torn cuticles. Gloves come in several different sizes, and you should make sure that they are well-fitting. A glove that’s too small will cut off your circulation, and one that is too big will feel baggy and uncomfortable inside the receptive partner. You can also wear gloves for other purposes: if your nails are long, sharp or ragged, if you are squeamish about the cleanliness of anal penetration, or if you want to smooth out your fingers before they go inside your lover. If you find that wearing latex gloves irritates your skin, you may be sensitive to the powder that coats the inside, which is common; find an unpowdered glove instead.

As part of safer sex, you should use a condom every time you have either vaginal and anal penetration. In fact, because of the delicacy of anal and rectal tissue, bodily fluids infected with HIV and other viruses are transmitted and absorbed easier and more quickly into the bloodstream through the mucous membrane of the rectum. Thus, unprotected anal intercourse can be more risky for both partners than unprotected vaginal intercourse.

You should never, ever put anything in the vagina that has been in the anus without thoroughly washing and disinfecting it first. Transferring rectal bacteria into the vagina can lead to yeast infections, urinary tract infections, and other ailments which will put a halt to your sex life. Just don’t go there. If you’re likely to want to use the same hand or tool in both the vagina and the anus, or your anus and then your partner’s, that’s a lot of running to the bathroom to wash up each time you want to switch gears. Using a new glove and/or condom each time you switch orifices or activities means less time cleaning and more time fucking.

Nov 292000

What are your thoughts on what has become a new trend in adult films: the ass to mouth act? Have you indulged in this act, and how would you suggest one prepare for such a nasty maneuver? I would appreciate any advice you can give me.


Taking your dick out of a woman’s ass and directly shoving it into her mouth may make for exciting porn, but, in real life, it can be problematic. Bacteria lives in the butt that may not peacefully exist in the mouth, and could lead to an infection. No matter how squeaky clean her rectum may be, chances are there are at least trace amounts of fecal matter which may end up on your dick — do you really want to make her suck that off? Would you put it in your own mouth?

I have a better idea. Fuck her in the ass til she’s right on the edge of orgasm, or you are. Order her to get on her knees and close her eyes. Talk to her, tell her she better open up her mouth for your cock. Have an anti-bacterial baby wipe stashed nearby, and quietly grab it, slide it over your cock, then toss it. Now proceed with sticking your rod in her mouth, keeping the fantasy intact, but keeping it clean for everyone involved.

Jul 302000

I like my boyfriend to play with me and put his fingers in my ass as we enjoy intercourse. We use butter as a lubricant (remember
Last Tango in Paris?). My question is: is it advisable to use butter as a lubricant? Can it produce infections? Are there any health risks?

—Concerned Anal Player

Thank the anal sex gods you wrote to me! Put that butter back in the kitchen where it belongs! Vegetable or oil based lubricants of any kind — including butter, olive oil, baby oil, Crisco, Vaseline, baby oil, or lotion — are not a good idea, especially for women. First, this group of lubricants breaks down latex, rendering your condoms and gloves useless in protecting you. Second, they weren’t made for sex so they definitely don’t work as well as the many lubricants on the market which are formulated specifically for sex. Third, these kinds of common household products will wreak havoc is a woman’s pussy. Even when you’re headed for her ass, and you are being diligent about cross-contamination (nothing should ever go ass to pussy; change the condom, the glove, the toy or wash with hot water and antibacterial soap), sometimes a little lube finds its way into her front door. In this case, that lube is a perfect breeding ground for infection, will not rinse out, and will most likely cause an infection of some kind.

A much better choice for you is a nice, thick water-based lube. Thicker lubes are better because they tend to stay wet longer, and act as a little bit of a cushion inside that delicate rectum. Some examples are: Maximus (imported from England), ID, Slippery Stuff Gel (glycerin-free and a good bet for people allergic or sensitive to glycerin), or Foreplay Lube de Luxe (Gel or Cream). The “Cream” version is actually the texture of Vaseline, but it’s water-based. You may also want to try a silicone-based lube. I know people who swear by them because they stay wet forever, but they aren’t my favorite.

May 222000

My boyfriend seems to like my finger up his butt when I suck his cock. I’d like to finger him, and maybe fuck him with my fingers. I am worried, however, that I might hurt or scratch him because I have nice long fingernails, and I hate to cut them. Any advice?


Congratulations on finding your man’s ass! And kudos to him for not freaking out when you reach back there during a blow job! So much pleasure awaits both of you, but you’re smart to be concerned about your nails. The tissue of the anus and rectum is very delicate and requires gentle handling. Don’t despair — you can keep your talons and still give him a good ass fucking.

First, you need to invest in some disposable latex gloves; you can get them at drug stores and sex toy stores. They come in different sizes, and make sure you get the correct size with a good fit; you’ll have better sensitivity so you can feel what you’re doing and he won’t feel a wrinkled baggy glove inside his ass. If you are allergic or sensitive to latex, you should get vinyl gloves; they are harder to find and a little more expensive.

Many women with long nails like to stuff cotton balls in the fingertips of the gloves in order to protect their manicure and their partner’s delicate asshole. Others wrap their nails in gauze before slipping on a glove. One woman recently told me she’s found a finger bandage which she puts on underneath a latex glove. Whichever option you choose, make sure you use plenty of lube on your glove.

Feb 252000

Are urine enemas the things of fiction writers or are they safe?

–Kevin in Australia

First, let’s talk about just what a urine enema is — or can be. You could fill a bag with your own urine (full strength or diluted with water) and give yourself an enema, or you could share your special golden potion with a friend. Remember that whatever you put in a rectum will be instantaneously absorbed into the bloodstream, so a diluted version may be your best bet. And even so, you may get an upset stomach. You could also penetrate someone with your dick, and pee inside their rectum, producing a brief, but less complicated piss douche. Some men cannot urinate when they have an erection, so then one would have to come, go soft, then pee. Other men I talked to claim they can pee while they are hard.

So how safe are all these water sports? Splash Alan, a contributing writer to Waterboys Magazine, says,

Piss is sterile. As long as you don’t have any urinary tract infections your urine is safe. Hell, back when I was a Navy corpsman we were instructed to always try and keep open battle wounds to the abdomen moist. If water wasn’t available the instructions were ‘piss on the battle dressings before application to the wound.’ What more can I say?

According to San Francisco Sex Information, urine isn’t necessarily sterile, but it is very clean as far as bodily fluids go, even cleaner than spit. Peeing on someone or in someone is relatively safe; being peed on or in can be safe, with a few exceptions. Hepatitis B, cytomegalovirus (CMV), the genital herpes virus, chlamydia, and gonorrhea may be present in the urine of a person infected with any of these diseases, says Dr. Beth Brown, a physician and advice columnist. Therefore, if infected urine comes into contact with broken skin or a mucous membrane (like the rectum), transmission and infection can occur. There is no evidence of HIV being transmitted through urine, however most sex educators will not say it is 100% safe.

I don’t know anyone who has actually given or received a urine enema, but I will keep asking for you, Kevin!

Feb 162000

I have some interest in enemas and want to know about using coffee or beer in an enema. Do porn stars have an enema before an anal scene? Do they eat a special diet to keep from getting gassy?

–L.C. Jr.

Enemas are a great way to cleanse your anal canal and rectum, and many people like to have an enema before anal penetration to make sure their butts are squeaky clean. When giving yourself an enema, you should always, always use plain warm water. You should never add coffee, beer, wine, or any other additives to an enema — this will make you very sick very quickly. Anything you put in your rectum will be directly absorbed into your bloodstream, just like if you shot it into your veins with a hypodermic needle. Plain water is all you need to flush yourself out.

In general, porn stars do give themselves enemas before anal sex scenes, although not right before a scene. It’s a good idea to give yourself an enema several hours before you plan on having anal sex in order to give your body a chance to recover and relax. Some porn stars I know actually clean out the night before and report that it’s the best way to ensure that their bowels have returned to normal and there won’t be any unexpected mess.

As for their diets, well, it depends. Some people find that before a round of heavy anal play, they like to eat mild foods which are easy to digest and won’t upset their gastrointestinal tract. Many of the gay male anal fisters I know recommend avoiding foods with seeds like strawberries. I’d say that avoiding the five alarm chili is a great idea!