Jun 302005

My fiancé and I have been exploring BDSM, which we enjoy fully. He wants to have anal sex with me, and although it would be the first for me, I’m willing to try it out at least once. He does have a really big penis — gloriously big — and I’m concerned about the process as I’m a small woman. Is there anything I can do to prepare myself for him and make this enjoyable for both of us?

–Tiny But Tempted

Your physical size does not necessarily correlate with your ability to take a “gloriously big” cock up your ass. I’ve seen women who are five feet tall and 98 pounds with very large things comfortably nestled in their behinds. It’s more about your internal than your external size. Like the pussy, the ass has the ability to expand when you’re aroused. Plus, the rectum is longer than the vagina and therefore can usually accommodate something bigger.

However, since your guy is larger than average, it means that you’re going to have to work your way up slowly. And since it’s your very first anal adventure, his cock should not go into your ass all in one evening. Instead, I recommend that you begin playing with a finger or a slim toy either alone or with him. Use plenty of lube, go slowly, and stimulate your clit. When you’ve practiced a few times with the one finger/small toy, and it feels great, you can move on to two fingers or a slightly bigger toy. Again, you can play together or you can add anal play to your masturbation. The important thing is not to rush the process. Find a dildo that’s “one step down” from your man’s cock. When you’ve worked up to taking that dildo, and it’s comfortable and pleasurable, then you can try his cock. Make sure he goes very slowly, and that you give him lots of feedback about how it feels. If you both take your time and let your ass set the pace, it will reward you in the end!

Feb 182005

Do you recommend using inflatable dildos to stretch the rectum?

–Ready to Blow Up

I don’t recommend anything to literally stretch the rectum. Toys are a great tool to teach the ass to relax and open up, to get it accustomed to being penetrated, and to warm up for more. It’s not stretching as much as it’s expanding, since the rectum has the ability expand when a person is turned on and relaxed. Inflatable dildos and butt plugs are a fun toy to play with, and they are also a great way to gradually increase the width of a toy you can take in your ass without investing in a new one. Make sure you inflate the toy before you put it in your ass to measure its limit, then you can gradually work your way up from one pump to several pumps!

Dec 152004

I started doing anal play about ten years ago. It was somewhat uncomfortable, but I persisted. Well, my persistence paid off. I am now able to take a dildo about 10 inches long and about 7.5 inches in circumference. I thoroughly enjoy it, but I have a question about how deep you can go. I tried inserting it to about 12 inches, and I got it worked in, but after about five minutes, I removed it, and there was blood. It shook me up big time. It stopped immediately, but I didn’t insert anything for week for fear of starting something I couldn’t stop. I felt no pain and it felt good. Is the blood a big deal?

–Size Queen

Since the rectum is quite delicate and covered by mucous membrane, even the gentlest of penetration with the smallest of toys can cause a small tear and a little bit of blood. It’s usually not cause for concern as long as the amount of blood is small and there’s no serious pain or discomfort. However, in your case, you’re using very long, thick toys for penetration that give you more of a chance of causing an abrasion or tear; you must realize that a twelve-inch dildo or one that is nearly eight inches thick is huge and not common. When you penetrate your ass with something longer than about ten inches, you move beyond the rectum into the sigmoid colon, which is made up of fragile tissues. Technically, anything bigger than 10 inches could perforate this, especially if it’s inflexible. Plus, an extremely thick dildo can stress the rectal lining. My advice is that at the first sign of blood, you should stop immediately and give your ass a few days to recover. If these big dildos continue to make you bleed, then I suggest you select smaller ones.

Apr 172004

I was hoping to get some of your good advice before purchasing a strap-on to fuck my girlfriend in the ass. I came across one called the “double whammy”, a two-headed dildo which has one long shaft to insert in the recipient and another shorter shaft to insert in the wearer of the strap-on harness. This enables the one doing the fucking (me) to feel some penetration herself and thus enjoy the whole thing a little more. Have you in your years of experience come across one of these things and if so are they any good for either partner? What does it feel like for the wearer? Can the wearer really get off while fucking the other person?

–Double Dildo Dilemma

Most double ended dildos are just like one long dildo with two heads, and, while they can be fun for partners to share, they can’t be used with a strap-on harness. The toy that you described sounds to me like the Nexus, a silicone double-headed dildo from Vixen Creations that was designed specifically for use with a harness. One end sticks out of the harness for fucking your girl, and the other slips inside you. As you thrust with your hips to push the dildo inside your partner, the other end penetrates you. The Nexus is a totally unique toy, and one that lots of people rave about; I’ve used it myself and really like it. It comes in two sizes, and is ideal if the size of each dildo works for each partner.

As to your question, “Can the wearer really get off while fucking the other person?” Well, that all depends on how the wearer gets off! For some women, wearing a standard (not two headed) dildo in a harness is very arousing since as you start thrusting, the base of the dildo can rub up against your clit. Also, there are vibrating dildos that can be used in a harness, to give the wearer (and her partner) plenty of buzz where it counts. If penetration is what gets you off, and the Nexus hits the right spot, then it can add a whole new level to your strap-on pleasure.

Feb 132003

I’m a lesbian in a relationship with a great girl. I’d visited your website before and the idea of anal sex interested both of us, but we’d never gone beyond a little hesitant touching. Your book was an eye-opening experience! I thought that my sex life was fun before, but you helped us to safely discover a whole new level of pleasure, and I really want to thank you for that. My girlfriend and I have different views on the subject: she likes it when I penetrate her with a strap-on dildo; I prefer when she puts a butt plug in my ass, and I wear it for a while — I like the “full feeling” better. We use condoms on our toys, we’re careful to take our time, and we use plenty of lubricant.

After an anal session, whether it’s with a butt plug or dildo, however, my girlfriend gets abdominal cramps. She has absolutely no pain during sex itself (quite the opposite), only afterwards! We have tried different positions, enemas, breathing techniques, and having several orgasms before anal penetration. The dildo I am using is only about 1.5″ in diameter, and she has no problem taking it. The only time she doesn’t suffer these symptoms is when we just do gentle fingering (one or two fingers). This would be fine except she is very into the strap-on. Can you help us?

–Strap-on Slut

When people write to me about pain and discomfort from anal penetration, it’s usually about burning and other painful feelings in their rectum. However, cramping after anal sex is not unusual. In fact, lots of people ask me, “After you did your final scene in The Ultimate Guide to Anal Sex for Women video, wasn’t your ass sore?” I tell them the truth: I had so much warm up with fingers and toys, and I was so turned on that my ass was relaxed and open. Even lots of anal penetration over several hours of taping didn’t make me sore, but I did feel some cramps in my abdomen afterwards. Of course, making my video was like the Anal Olympics for me, and I don’t want your girlfriend to have discomfort just from what is, comparatively, a run around the track.

I have a few suggestions. First, don’t fuck on a full stomach. If her body is trying to digest a big meal, then stimulation in the rectum could confuse the natural bowel processes. Similarly, just like you shouldn’t drink gallons of water before you work out your abdominal muscles at the gym, the same holds true for getting plowed. Second, consider using a shorter dildo. The longer the cock, the closer it gets to the lower colon, which for some people may disrupt colonic activity and cause cramps. Finally, as you thrust in and out of her with your cock, air can be pushed inside her rectum and travel upward in the body, giving her cramps, so no more doing her in wind tunnels. Seriously, if her cramping persists, I suggest she consult a physician to see if she is suffering from a gastrointestinal problem.

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.

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?

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!

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.

May 092001

I like to have objects in my ass while I masturbate, but I don’t have a dildo. What kinds of household objects can I use to simulate a penis?

—Fill My Ass

There is a reason that household objects are household objects; they each have a purpose, and it’s not sexual. I am thrilled that you’ve discovered anal penetration as part of your masturbation ritual, but I really don’t want to encourage you to grab the hairbrush, the shampoo bottle, the cucumber, or anything else lying around. Has it been done? Of course, but I don’t condone it usually.

I really recommend that you buy a dildo. You need something with a flared base for anal penetration; it’s an absolute necessity, so the object doesn’t get sucked into your ass or lost somewhere in your rectum. Sex toys were manufactured with sex in mind, they are designed for penetration, and therefore much more ideal for it than a makeshift dong. There are relatively inexpensive dildos on the market, especially the rubber or jelly variety (silicone dicks are much more expensive). But yourself a $15 or $20 dildo, and I promise it is well worth the investment.