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?

Desperately Seeking Butt Briefs

Aug 182001
 


I have been looking for a few weeks for a pair of men’s briefs (latex or other material) with an internal butt plug or dildo, but with a hole for the penis and balls to come out and be free to play. I can’t find one anywhere! Any ideas?

—Desperately Seeking Butt Briefs

Well, aren’t you an ambitious one! I must say that I have tried to track down such a pair of undies for you, but haven’t had any luck. Although I do have a few suggestions about how you might create the briefs of your dreams. Start with a butt plug harness (available at many leather, fetish, and sex toy stores and web sites) to hold your favorite butt plug securely in your ass. Or, of you’re into body and genital bondage, you may choose to have someone put a rope harness on you to keep the plug in. Then, add a tight pair of your favorite underwear that has such a flap in front for your woody to come out and play. Voila!

What’s In It For Her?

Aug 052001
 


I am in a relationship with woman, and we both want to try anal sex. But I have one concern. I know that it’s going to feel really good for me, because I am a guy, but what will it feel like for her? Do women get off on anal penetration, and if they do, then how exactly? Can my girlfriend come from it?

—What’s In It For Her?

Rest assured that there is plenty in it for her. First, let’s talk about the physical aspects of anal sex. Anorectal anatomy is nearly identical in men and women, and the entire area — the anus, anal canal, and rectum — is extremely rich in nerve endings and sensitive to stimulation of all kinds, including penetration. Because of this level of sensitivity, exploring our asses can bring us incredible sexual pleasure.

The one distinction in men and women’s anal anatomy is that men have a prostate gland, which can be reached and stimulated through the rectum. Although women don’t have a prostate, they do have a G-spot. The G-spot is reached through the front wall of the vagina, but it can also be indirectly stimulated through anal penetration. Since all that separates the rectum and the vagina is a thin membrane, if you angle a finger, toy, or penis toward the front wall of the vagina, women still may experience G-spot stimulation. Many women find that the G-spot stimulation they get from anal sex is one way they can have an orgasm. Another way for her to orgasm is to add clitoral stimulation as you penetrate her. Give her clit some rubbing action or let her jerk herself off with her hand or a vibrator while you do her in the ass, and see what happens.

In addition to the bundle of physical pleasure that anal stimulation brings, there are complex emotional and psychological issues that contribute to the erotic experience. For some people, the idea that anal sex is naughty, forbidden and taboo is very exciting, and adds to their enjoyment of it. For others, the great amount of trust one must have in a partner heightens the physical pleasure; allowing your partner to penetrate you in this special place says, “Here is a delicate part of my body, and I trust you not to hurt me but to make me feel very good.” That power exchange can be very intense for lovers. Anal sex is often represented in popular culture as violent and degrading; however, in reality, it can be extremely intimate, connecting, and even spiritual.

Scared of the Mess

Jul 232001
 


Anal sex has been an unfulfilled curiosity of mine for many years; as a young twentysomething, I was forever intrigued by it. My boyfriend and I have talked about it, and being experienced, he has suggested we try it. I feel extremely comfortable with him, and, aside from anal sex, we have an incredibly open and experimental sex life. I told him I am curious but also hesitant. The thing is, I’m embarrassed to tell him the real reason why because it’s seems petty to me. I’m so scared about things getting messy as I’ve heard some very unappealing stories about bad smells or fecal matter being present. I know that as humans, our bodies have natural functions, but I would be mortified if that happened while we were having anal sex. As it is, I really want this to be something special as it’s taken me a long time to find anyone I could trust, and I don’t want to be totally turned off if things go haywire.

—Scared of the Mes

Take a deep breath! Your concern is the most common one I hear about anal sex. The first thing you need is a brief anatomy lesson. During anal penetration with fingers, toys, and penises, the area of your body that we’re dealing with is the rectum. The rectum is not a storage facility, so no feces are stored there; it’s merely a passageway. Feces move from the colon to the rectum, then out of the body when you defecate. So, if you have a bowel movement before you have anal sex, there should only be trace amounts of fecal matter in the rectum. Now, this is provided that you are a relatively healthy person with a good diet, normal bowel habits, and no gastrointestinal problems. So, if you feel like you have to go, by all means go, because if you don’t listen to your body, then you may, in fact, have a mess on your hands simply because you needed to have a bowel movement and you didn’t.

For those people who are squeamish about “being clean,” I recommend an enema. Go to the drug store, buy a Fleet enema, then empty the contents of the bottle and fill it with plain warm water. Fleet enemas contain a laxative which isn’t necessary; all you need is warm water. Follow the instructions on the box, and repeat until all that comes out of your ass is clear water. Make sure you have an enema several hours before you plan to have anal sex, since your body needs time to recover.

Now, after telling you all about cleaning yourself out, I must quote a fellow anal queen, adult film star Chloe, who says, “Get over your fear of shit!” I am not saying you need to love or even like shit, but you need to let go of your anxieties. The truth is that the more anal play you engage in, the more likely you are to run into it once and awhile, so you might as well just smile, grab a baby wipe, clean up, and move on.

Smooth Ass

Jul 132001
 


This is in response to Bryan’s question about hair removal in the anal area. I have had two sessions of laser treatment on my asshole and can say that laser treatment does work. There are some drawbacks, however. Laser treatment can be expensive (about $150 per session) and it takes several (3 or more) sessions to remove most of the hair. Also, if the hair is light-colored, laser treatment is probably not going to have much effect, and you’ll just be wasting your money.

As to the question of pain, there really isn’t that much. It feels like a pin prick. A little ice on the area right before the treatment goes a long way. I would suggest going into your local laser treatment clinic for a consultation. I found out that hair removal on the asshole is fairly common for these folks, and they don’t have any problem doing the procedure.

—Smooth Ass

Thanks for writing in response to one of my previous columns, where Brian asked about hair removal for the butthole. I just love it when readers give each other helpful tips and techniques, so thanks for sharing your experience! For those of you considering the different methods for achieving your own smooth ass, remember that there are several types besides laser treatment. Shaving and waxing are also options, and much less expensive, although not permanent. Plus, shaving can be an erotic scene in addition to fulfilling the practical matter of making one’s little pucker hole hairless. I personally love to shave my ass, and find it very sexy when I let someone else take a sharp razor to my tender hole — it totally turns me on! Whichever method you choose, be careful, use common sense, and enjoy that smooth opening with abandon!

Buff Girls Rock My World

Jun 202001
 


Since I have been old enough to jerk off, I have been attracted to exceptionally buff and athletic women. The first time I ejaculated, I was fourteen and I was watching women’s gymnastics in the summer Olympics on television. Since then, I have desired a non-stereotypically-feminine woman. As my sexual development progressed, I discovered that I wanted such a woman to sodomize me—to fuck me in the ass with a strap-on. I have thought long and hard about this. Buff, athletic women are the most amazing, sexy creatures on the planet.

The desire has remained totally unsatisfied throughout my life. Recently, though, I was able, through some miracle, to go on a couple of dates with this girl who is on the diving team of my university. She is my ideal woman, and I really like her, but I’m afraid if I ask her for anal sex, I will lose a relationship with the sexiest, coolest, sweetest girl I have ever had the chance to be involved with. Help! How do I find out if she would be into anal sex with me? And, if not, how in the world will I ever find another as buff and beautiful as she is that might just be into anal sex with me? This girl is amazing, and I don’t want to lose her, even if that means sticking my thumb up my ass while thinking about her, and settling for strictly vanilla sex with the girl of my dreams.

—Buff Girls Rock My World

Well, it sounds like you really like athletic, assertive, maybe even butch, heterosexual women. I commend you for figuring out the unique type of person that floats your boat (and obviously gets your dick hard). As for seeing if she’s into fucking you in the ass, well, I think you need to take the plunge and ask her. I understand that you don’t want to lose her, but you also want to have your anal desires fulfilled, and those anal desires seem pretty fucking strong to me. So, approach her honestly and in a non-confrontational way, and tell her what you want. Hopefully, she will make all your dreams come true, and strap it on.

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.

Ass Master Who Likes Golden Showers

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!

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