May 072014
 

I have recently started a new relationship, and we have been getting to know each other including experimenting a little with different sexual things. The topic of anal sex came up and she is turned on by it, but so far her rule is “two fingers max.” She’s a very small person all around, and that includes her asshole. She wants to stretch her ass to accommodate my cock, so we want to know how to do it and how long it will take.

–Patient in Palo Alto

Her small stature does not necessarily have anything to do with how much cock she can take in her ass. Haven’t you seen those tiny porn starlets take huge dicks up their butts? It is absolutely possible. Her objective should not be to stretch her ass, but rather to learn to relax the sphincter muscles to make penetration comfortable and pleasurable. I suggest you begin slowly. Try one finger in her ass, your tongue or fingers or a vibrator on her clit, and a rousing orgasm. From there, let her set the pace as you work your way up from one finger to two, and so on. You can also work your way up with dildos or butt plugs in graduated sizes. You shouldn’t move on to the next step until everything feels great. How long it takes to get used to this new sensation, be comfortable with anal play, and work up to a cock in her ass will totally depend on her. Don’t be so focused on how long it will take, just enjoy all the fun you’ll have getting there!

Mar 192014
 

I have a fantastic fantasy that I would like to put into practice: having a urine enema. How safe is it to have a urine enema? Is there a difference between using my own urine or my husband’s? Are there ways to make this activity safer? Related to this, is it okay for my husband to urinate in my rectum when we are having anal sex? That’s another fantasy that gets me hot just writing about it!

–Piss Piggy

As a general rule, I recommend plain warm water enemas only, and I caution people against adding any ingredients to the ol’ enema bag. Whatever you introduce into your rectum will be absorbed into the bloodstream quickly, which is why substances like wine, liquor, and coffee are never a good idea. However, over the years, I’ve gotten dozens of letters about piss enemas, so I’ve done some research.

Urine is a realtively clean bodily fluid, although it’s not completely sterile, as some people say. Ingesting your own urine is relatively safe, although it contains chemicals and substances your body wants to eliminate, and you’re putting those waste products back into your body. Some alternative health practitioners believe that urine enemas have healing properties and can help with acne, gastrointestinal problems, and eczema (not surprisingly, there is no research on the subject).

The biggest concern with ingesting someone else’s urine is that 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 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. If you and your husband have tested negative for all STDs and are monogamous, then your piss or his should be fine.

I recommend you dilute the pee in plain warm water (or distilled water warmed up) in order to make it less concentrated. It still might make you a little nauseous. Make sure you drink lots of water to stay hydrated.

As for having him pee in your ass, the same rules apply, although there is no way to dilute the pee.

Feb 192014
 

My girlfriend likes both vaginal and anal penetration a lot and so do I. I’m looking to expand our repertoire with some toys. I notice that you often include sex toys in your writing, books, and films, but don’t talk about the psychology of them. My girlfriend just isn’t turned on by sex toys because she feels like it is not me pleasuring her, but the toy. Her disinterest has come to the point where she doesn’t even want to try them. She came close to trying a small vibrator one time, but when I went to buy it, she changed her mind and didn’t want it. My fantasy is to not only use toys on her, but for her to use them on me as well. Is there anything that could help her see that it would be me pleasuring her, not just some inanimate object?

–Dying to Have A Toy Box

You’re absolutely right about me — I love sex toys! In fact, I love them so much, I wrote a book all about them (it’s called The Big Book of Sex Toys). There are lots of myths about sex toys, and it sounds like your girlfriend’s lack of interest in them may have to do with some of these misconceptions. People mistakenly believe that if you bring a sex toy into the bedroom, it means that something’s wrong; others think that sex should not need anything extra besides just two bodies, that it should all come “naturally.” These are the same folks that think lube isn’t necessary, you just need to be turned on! I’m not discounting all that we can do with our fingers, hands, tongues, mouths, cocks, clits, and pussies, not to mention lots of other body parts. However, toys can bring your sex life to a whole new level! Plus, sex toys can help you be in two places at the same time (wink, wink), give you a helping hand, and do things that human beings just can’t do!

I think it’s worth it for the two of you to talk about toys. While different toys do different things, remind her that this is not an either/or choice or a contest. If you’re using toys together, then it’s about the connection and fun between you — not about whether it’s the toy that’s responsible for her pleasure and/or orgasm or you. Sex toys are meant to enhance your sex life, not be a substitute for anyone. I suggest you take your girlfriend shopping at a sex-positive store where she can see a variety of toys out of the packaging, pick them up, and turn them on. Let her choose a toy — one that she likes, appeals to her, or is intriguing in some way. If she’s not sure, ask the person working at the store for some advice. Empower her to take the lead on buying it, and give her time to get used to using it together.

Feb 052014
 

My girlfriend knows that anal sex has been a long time fantasy of mine, and recently she decided to try it. We were in the shower fooling around, then we had vaginal sex. She suggested I put it in her ass, and, of course, I gladly obliged. I gently placed my dick at the entrance of her sexy asshole, and she pulled her ass cheeks apart for me. I slowly tried to push my dick in her ass, but it was like pushing my dick against a wall. I was just not going anywhere. The funny thing is that I was fully lubed up and so was she. She was also very relaxed, so I don’t see why I couldn’t get my dick inside her. My dick is about eight inches long and three inches thick, could this be the reason?

–Stranded in the Shower

It sounds like your girlfriend has never had anal sex before, and a nice warm shower does not qualify as warming her up! I am not surprised it felt impossible to get inside; the sphincter muscles are a tight ring of muscles and they’ll keep you from going anywhere you’re not welcome. In this case, you weren’t welcome because you tried to go from 0 to 60 in five seconds. So let’s start over and introduce her to this wonderful activity properly, shall we?

Begin exploring your girlfriend’s ass with analingus, external stimulation, and one finger. As you lick her pussy or stimulate her clit, slip a well-lubed finger inside her ass gently and slowly. Build from this experience and make sure to let her set the pace. Don’t proceed to add another finger or try out a toy until she’s ready.

Once you’ve had many sessions of anal penetration with fingers and toys, only then are you ready to put your dick in her ass. It sounds like your dick is both longer and a lot thicker than average. Get a dildo that’s just slightly smaller than your erect cock, and begin playing with it. Once she can take that dildo comfortably and it feels really good, then you can give your dick another try. If you return to the shower for the big event, make sure to use a silicone-based lubricant, since water-based lubes will simply wash away.

Jan 162014
 

A few months ago I was watching a cable station late at night and they had a segment on porn stars. In this program, they dealt with one girl’s preparations for filming. She discussed her tattoos, piercings, and laser removal of her pubic hair. She had her hair touched up, nails done, legs waxed, and did a stretch in the tanning bed. While she was having her makeup applied, she mentioned that she had her rectum bleached. I had never heard of that.

One night while preparing for anal sex, I noticed a dark discoloration around my anus. I told my husband about the show I watched and explained how this performer had her rectum bleached. He told me that I was crazy. Was I? Is there something out there that can bleach this discoloration away? If so, I would like to know more about it. Can this be done at home? What products can be used and where can I buy them?  I have a lot of adult movies and I have noticed that most of the female actors look like they may have bleached their butts.

–Want a White Eye

You were not imagining things, there are products on the market to bleach the skin, and a few are marketed specifically as anal bleaching creams. I’ll bet you saw the segment on Dr. 90210 on E! where adult film star Tabitha Stevens went to Pink Cheeks salon in Southern California and had her asshole bleached. The salon sells its own cream, Pink Cheeks Amazing Anal Bleaching Cream (and you can order it over the phone, 818-906-8225). According to its label, the cream’s active ingredient is 4% hydroquinone, a substance used to lighten dark skin. It comes with instructions that recommend you have your anus waxed prior to application, and that you use it every night until you achieve the shade you want (which typically is in a week or two). There is a less expensive alternative, simply called Anal Bleaching Cream.

These products have not exactly registered on the Food and Drug Administration’s radar, so the safety of them has not been researched. The fact is everyone’s skin around their anus is a darker shade than their regular skin tone; in other words, it’s natural and I’m inclined not to fuck with it. Plus, your perception that “most of the female actors look like they may have bleached their butts” is not accurate; some have, but the majority of brown eyes you see on screen are as nature made them.

Dec 142013
 

I feel like my current relationship will cause my entire existence to revolve around my asshole! I’m no anal virgin, mind you. I’ve got plenty of experience with enemas, plugs, fucking and exploration. I rather enjoy it all! But how much is too much? I am in a Dominant/submissive relationship, and my Master has recently requested that I remain plugged 24/7/365, only removing it to relieve myself or during extreme illness or injury. When I wear a plug for a long time, I get sore and unpleasantly distracted very quickly. I know this isn’t always a bad thing, but it’s starting to interfere with my work and overall life. He also expects me to do complete enemas with a shower hose every day. Right now, I’ve only got the resources to do that once or twice a week, but it plays hell with my whole system for days afterwards!

Does it get better with time and a more stringent routine? So much of it already throws off my entire being! I’ve run the predictable course of diarrhea, constipation, nausea, loss of appetite, cramping, soreness, irritation and have lost a considerable amount of weight (20 pounds) in just over a month. I can’t say that all of it is related to the new ass attentions, but I’m certain that the majority is.

How do I continue to want to do what my Master expects of me and not flatly refuse what I think will ultimately cause damage? I just don’t want to be hurting and sick all the time. Everything seems to revolve around my ass. It’s frustrating and doesn’t make me feel anywhere nearly as good as I want it to. Instead of feeling clean and “free” afterwards, or pleasantly full and reminded, I feel more drained and exhausted. Sure, my ass might smell like daisies and be stretched to “convenient” proportions, but it’s no fun anymore and goes way beyond that.

I sometimes even feel like without my ass, what would He want with me? I don’t want to take the fun out of it for my Master, but I feel like if I can’t get over this one hurdle. So much of His passion is about anal, so our whole compatibility might be in jeopardy. He cares about me and I don’t think He wants to intentionally hurt me, but I’m barely keeping up! What can I do?

–In Anal Agony

You are missing two critical elements in your Dominant/submissive relationship: consent and mutual satisfaction. It sounds to me like you are blindly following orders that are physically harming you and that you don’t enjoy on any level. D/s relationships can help us test our own boundaries, but the relationship you describe is way out of bounds. No one should have an enema every day. No one can wear a butt plug 24/7. It sounds like your Master has been reading too much fantasy fiction and hasn’t had enough real-world experience, because what he is asking of you is impractical, unsafe, and bizarre. I support fantasizing about wild, out there things and I support Dominants who threaten submissives with various kinds of torture, but this crosses the line. You must speak up for yourself and he must be willing to negotiate more realistic expectations, otherwise this is a one-way relationship you shouldn’t be in.

Dec 022013
 

I have a dildo that’s seven and a half inches long for anal penetration. In the two months that I have had it, I have already been able to take all of the insertable length in my booty, so I think I am ready to go up a size. I want something that is longer, but also has a lot of girth; can you recommend something that will make me scream in ecstasy? What are some of the best toys for self-stimulation? Should I get a blow up doll with a dick?

–Screamer

There are lots of large dildos on the market, but I’m a big fan of silicone toys and I always recommend them. Silicone is pliable and resilient; it conducts body heat and vibration; it’s very easy to clean since it’s not porous like rubber or PVC. If you’re looking for something thick, then Randy by Vixen Creations is awesome; it’s got the diameter of a soda can! Vixen also makes a dildo called Outlaw which is eight and a half inches long and over two inches in diameter. Tantus has a new giant in their line up called Hoss which is 11″ long and should keep you busy for a while. If you like metal toys, then the Eleven by NJoy simply must be on your wish list; it’s expensive, but it’s a size queen’s dream come true!

As for good anal toys for masturbation, I always find that longer toys are easier to hold and maneuver, as are baton-style toys with a handle. You may also want to investigate dildos with a suction cup on the end of them. You can stick them to the shower wall for example and ride til your heart’s content. Blow up dolls make for a good punchline, but when it comes to penetration, I am not sure how they work, really. There is a John Holmes Fantasy Doll, but I haven’t been able to find anyone who’s actually used it. Just as there are replicas of female porn stars’ pussies and asses, there are replicas of male porn stars’ penises, and they are some of the biggest dildos I’ve seen. They are mostly gay porn stars, but a cock is a cock, so who cares?

Sep 112013
 

My girlfriend and I have just discovered anal sex and enjoy it a lot; I really enjoy having my cock in her tight asshole. But there’s one thing I want to ask about: the next day after anal sex, I have a painful backache. We do the ‘spoon’ position, and while it is happening, I don’t have any pain at all. Do you know anyone else with this problem and do you have any advice for me?

–Want to Get Laid, Not Laid Up

Welcome to the wonderful world of anal sex! It sounds like you would be off to a pleasurable start except for the painful aftermath. My first impression is that this is probably muscular pain. When you start a new sexual activity, you use a bunch of muscles you’re not used to exercising on a regular basis; just like if you started a new work out regime at the gym, your body needs some to adjust. It may simply be a matter of awakening those muscles and getting them back in shape.

It could also be the position you’re in is putting strain on your lower back. The next time you do it, try to concentrate on your body movements and see if the position is uncomfortable for you; perhaps you only need to make a slight angle adjustment and it will feel better. You can also do regular stretching and simple exercises to avoid muscle strains. Find a personal trainer, physical therapist, or someone knowledgeable about working out and ask them to recommend some exercises for strengthening your lower back. Once you get your back in better shape, there will be no stopping you.

Aug 282013
 

My partner and I are relatively new to anal fisting after almost 30 years of marriage. We bought your book about five years ago, and we also have all three of your anal sex guide videos. She tells me that her hand hurts, then goes numb while she is fisting me. She thinks that there is a lot of pressure on her hand, and she’s scared and nervous about going too deep and thrusting. Do you have any suggestions to help us achieve more depth with less pain for her?

–Fisting in the Golden Years

Anal fisting is possible because the sphincter muscles can be trained to relax enough to make penetration comfortable and the rectum can expand to accommodate something as sizable as a hand. However, the anal opening and the anal canal (the first few inches inside) still tend to feel quite tight once you’re inside, and that’s because of the sphincter muscles. I’ve certainly felt like my hand was in a vice grip a time or two during an anal fisting! That said, the vice grip sensation was fleeting and subsided as the person’s ass relaxed. Plus, while it has felt really snug inside someone’s ass, I’ve never felt pain or a loss of circulation, and it sounds like your partner has experienced both.

She is correct — there is a lot of pressure on her hand, but that pressure should not be so intense that it causes pain. Beyond the pain, the numb feeling she experiences means she’s losing circulation to her hand, which is actually quite dangerous. I suspect that your ass may not be relaxed enough once she gets inside, so perhaps more warm up is necessary before she proceeds from five fingers to the whole hand. Because you mentioned being in “your golden years,” I also wonder whether she has arthritis or another condition which is causing the pain in her hand. The safest solution to this problem is to switch over to some large plugs or dildos instead: they will give you the feeling of fullness and deep penetration without giving her discomfort.

Aug 132013
 

I really like licking my wife’s ass a lot. We just got into it because I was going down on her and decided to venture to her backdoor and see what happened. It turns her on immensely, even more than licking her pussy, it seems. I just want to make sure what we’re doing is safe. After licking her bare anus and probing with my tongue, should I rinse with a certain mouthwash to kill possibly harmful bacteria?

–Tongue Tied

Welcome to the wonderful world of rimming! Tonguing someone’s butthole is lots of fun, but it does have some risks. You said you’re married, but I don’t know how long you’ve been married and I don’t want to automatically assume that you and your wife are monogamous, since many couples have open relationships. There may be readers out there who are not married or monogamous, so I want to address all the angles in response to your question. It’s important for people to be tested for sexually transmitted infections, since asslicking can put one at risk for gonorrhea, chlamydia, herpes, syphillis, HPV, and hepatitis A; there are no recorded cases of HIV transmission through rimming. In general, the giver is more at risk than the receiver, but if the giver has a cold sore, bleeding gums, or cut on their mouth, that puts the receiver at greater risk.

If you’ve tested negative for all STIs and are monogamous, then the only other concern you have is that bacteria live in the rectum and anal canal. Not all of it is harmful, but some of it could be, especially intestinal parasites or EColi. If you are both in generally good health, then the risks are pretty minimal. Make sure your wife bathes before your asslicking sessions; a warm shower with a mild soap can lessen the amount of bacteria around her anus and just inside the anal canal. She can also have an enema, which will flush out a lot of the bacteria inside her lower rectum. There is no research about using mouthwash after rimming, but it certainly won’t do any harm and it does kill some germs.