Jul 052002
 

Me and my partner have always enjoyed anal sex. We have been together for a while and are expecting our first baby in three months. I know people are supposed to have “cravings” when they are pregnant, but my craving is that I want to be fucked in the ass even more than I did before! It feels great, and I experience no discomfort, but we want to make sure that we aren’t doing any harm to the baby (and I don’t exactly feel I can discuss it with my doctor!). I find the most comfortable position is on my knees with my butt sticking up so I can support my belly properly, and this way I can get the most cock in my ass. Will it be alright to continue up to the time you would normally stop having vaginal sex?

–Preggo Anal-Addict

Many women say that their libido, sexual tastes, and orgasms can change drastically during pregnancy, so know that your new craving is perfectly natural. According to most physicians, throughout your pregnancy, penetration (both vaginal and anal) with fingers is safe and with a cock is safe in low-risk pregnancies. One of the challenges of sex during pregnancy is finding comfortable positions, and it sounds like you’ve found a good one, at least for now — it may change when you get bigger. Your mate should definitely avoid deep thrusting and really hard slamming of any kind. Use a water-based lubricant, but be extra careful in preventing bacteria from the ass transferring to the vagina. Make sure his fingers and cock are super clean, or you may get an infection, which is often harder to treat during pregnancy. If you feel any discomfort during any sexual activity, stop at once. You said you don’t feel comfortable talking to your doctor about this, but for the sake of your health, and the health of your baby, it’s probably a good idea.

Jun 142002
 

I recently started dating, well, fucking, somebody I’ve known for close to a year. She has been without a sexual partner for a long time, but she’s a serious hypochondriac about STDs; she was tested for everything twice in April, and once last month. She gets depo shots, so we fuck without condoms (don’t worry, we do use lube). So, how come I get a strange rash on my glans and foreskin, usually lasting for a day or two, when I fuck her in the ass? It doesn’t hurt and it basically just makes the regular bumps and pores looks bigger and red. There’s no funky smell or discharge either. I’ve studied the symptoms of about every friggin’ STD more than this girl has, plus I’ve been tested more than she has. It doesn’t look like any STD I’ve heard of.

–Rash From Her Ass

I know you think your lover is a hypochondriac, but I applaud both of you for getting tested often because most people do not. And it also sounds like you know a lot about STDs, which makes you more educated than the average fella on that subject. I have a few theories about the rash on your cock. My first one is that you may be having an allergic reaction to the lube you are using. Most lubes, whether water-based or silicone-based have similar ingredients, but they are not all the same. Personally, I got a red, itchy pussy from one particular brand of lube that I was trying out for the first time. I never used it again, and I haven’t had the symptoms again. So, try using a different brand of lube and see if that changes anything. You could also go to your doctor when you’re having symptoms to get a full examination and see what he or she has to say. It sounds like you know a lot about STDs, but it’s always better to be safe than sorry.

Jun 072002
 

My girlfriend and I have been having anal sex for about four or five months. In fact, the first time I penetrated her was anally. After that, it’s been a once-in-a-while ritual where I get to have the pleasure of making love to her sexy ass. I enjoy it very much and she doesn’t mind letting me have my way, even though she says she receives little to no pleasure from it. We use plenty of lube and always warm up with shallow and slow penetration, deep breathing and lots of communication. We now do it now once every three weeks to a month, which is kind of my problem. I’d like to do it more often, but not too much.

I have two questions for you: How much anal sex do you think is healthy for a couple that wants to have a nice balance between the three major forms of sex (oral, vaginal and anal)? What kind of ways can I pleasure her when I do her in the ass? How can I make her come from anal sex?

–Booty Lover

There is no mathematical equation to determine “a nice balance,” nor is there any common recommendation about how much of one kind of sex a healthy couple should have. Sexuality and our particular practices are extremely unique to the individuals involved, and therefore so are our preferences and how often or little we indulge in them. I say if both you and your wife are content with how much sex you’re having, and the kinds of sex you’re having, then why mess with a good thing?

But it does sound like you’d like to add more anal sex to the menu, and your second question is the key to getting there. Because if you start to give her tremendous pleasure while you’re fucking her in the ass, then chances are she’ll want to do it more often. There are a number of ways to get a woman off while you’re fucking her ass. You can play with her clit while you penetrate her, or if the position you’re in makes that too difficult, encourage her to jerk herself off or even use a small vibrator. Clitoral stimulation combined with anal penetration is one of the ways some women can orgasm. If she likes double penetration, try putting a few fingers in her pussy or a slim dildo while you’re in her ass; this often increases the sensations in both places. Experiment with different positions in order to find her G-spot. Many women experience indirect G-spot stimulation through anal sex. You want to angle fingers, toys, or your cock toward the front of her body to find and stimulate the spot. Also, ask her what she’d like to do to make it feel not just better, but fantastic. Together, you can discover what will turn you both on.

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.