Oct 112005

Recently, my husband and I have stopped drinking. In the past, while intoxicated, my husband’s cock was much easier to take in my ass and even pleasurable. Now, I have a difficult time relaxing. Even when I do relax, there is a burning sensation that I cannot seem to get past, which makes me tense up even more. We are using plenty of lube in addition to my husband starting off with oral and a finger. Please help!

–Sober and Sidelined

I am not going to deny that people combine alcohol and/or drugs with anal sex in order to relax, lower their inhibitions, and let go a little. However, the same drinks and drugs that can help you let your hair down can also affect your judgment and your ability to honor your own boundaries. When people write to me and say, “I can only have anal sex if I’ve had five drinks,” I shake my head. I think it’s really important for people to be present and very connected to their bodies in order to fully enjoy anal play.

I suspect that part of what may be going on is that you were used to having anal sex while you were drunk and you’re stuck on that being the only way you can enjoy it. Maybe you’ve never experienced great anal sex sober, and your anxiety about what it might feel like if you’re not tipsy makes you tense. That tension leads to pain, and it becomes a vicious cycle. Cut yourself some slack and take a step back. Maybe you’ve got to start back at square one, and not progress to a cock until you can fully enjoy fingers or small toys. I think you should embrace your new sobriety and the opportunity to have new kinds of sexual experiences, and, most importantly, take your time.

Sep 182005

My boyfriend and I have been together for a year now and have an extremely trusting relationship. We have tried anal sex a few times and always with the same result. It does feel good, kind of, but can be quite uncomfortable for me too. The best way to explain it is that it feels exactly like I’m having a bowel movement and bowel movements aren’t particularly pleasurable to me. I expected it to feel not only different but better. We have tried a couple of positions including doggy-style with my back straight and me on my back with legs on his shoulders and him leaning over me a bit. We always use a water-based lube. I really want to enjoy anal, so is there any advice you can give us to help make it more pleasurable?

–Anal Vixen Wannabe

Since it’s difficult to determine exactly what people mean sometimes, I want to acknowledge that you said your bowel movements aren’t “particularly pleasurable”; if you are having a lot of discomfort, you should see a doctor. If you meant that pooping doesn’t get you off, then here are my thoughts. Lots of anal novices say that the first few times they get fucked in the ass, it feels like they have to go to the bathroom. It makes sense, because all the nerve endings are being stimulated, and another activity where we experience that is a bowel movement. Usually, after the first few times, this sensation (or at least the urgent feeling to run to the toilet) subsides. You may prefer the stimulation of a butt plug, which goes in and stays in, to a lot of in-and-out fucking.

Though I think it could be your brain that’s tripping you up on this one, and you could be stuck on your association with butt sex and defecation. There are several elements of anal sex that are a lot different than going to the john, namely the addition of sexual sensations like vaginal and clitoral stimulation and a hot, horny guy you love and trust. Right now, it seems like you feel a sensation and automatically associate it with a non-sexual activity, and you cannot get past that. Some solo sessions where you experiment with different toys and different sensations may help you find the things that work best for you and get you reacquainted with your ass in a new way. If you can “retrain” your brain to eroticize your ass as the erogenous zone that it is, you may find yourself more open to feeling pleasure there.

Aug 152005

My wife and I are new to anal sex but we are both very interested and excited to try it. She enjoys penetration of small objects such as fingers and small plugs. But as we work up slowly to bigger things such as dildos and my cock, she complains of pain and sometimes burning. Also, I can’t get either of these things to go in her ass. She has no problem taking fingers or small plugs. She has one tight ass, let me tell you. We are using plenty of Astroglide, so I don’t think lube is the issue. She is ready and willing to try, but her body is not cooperating and it zaps the pleasure and fun out of it a lot of the time. Can you give us some advice on how to make things go easier without the pain?

–Backdoor Newbies

It sounds like you are taking many of the necessary steps for safe and pleasurable anal penetration, including going slowly, warming up with small things like fingers and toys, and using plenty of lube. As fans of Astroglide, I suggest you try Astroglide Gel, that brand’s thicker lube. Thick water-based lubes tend to stay wet longer and can act as a cushion inside the delicate rectum. The burning she experiences can be another form of pain (many people report the same feeling when they rush it or take something too big) or the body’s reaction to the lube. Try some different lubes to rule out the latter.

My suggestion is that you add some clitoral stimulation to the mix, which you did not mention in your letter. Whether you use your tongue, your hand, a vibrator, or she touches herself, clitoral stimulation can help transform anal penetration into a much more pleasurable experience. In fact, some women say they can’t have anything in their ass without clit stimulation. Remember, the more turned on she is, the more her body will relax, and she can let go. It’s also important for her to be one hundred percent into it. Ask her if she has lingering fears or doubts, since they can be getting in the way of her enjoyment. Her state of mind and body are both crucial to the experience, so make sure you take care of them both.

Jul 262005

I have always enjoyed the feeling of anal penetration while making love to my husband. He enjoys finger fucking me or using a butt plug or other toy. It all feels great and we both enjoy it very much. Here’s the problem: about four days after anal sex and continuing for another week or so, I experience something akin to irritable bowel syndrome. It gets progressively worse, until about the eighth day after sex, and it slowly goes away. The feeling is very discomforting, yet we don’t want to give up anal sex. Any thoughts as to why this happens, and what I can do to eliminate it?

–Angry Butt Wants Relief

Anal sex alone does not cause irritable bowel syndrome (also known as IBS), or symptoms associated with it. Those symptoms can include chronic diarrhea and/or constipation, cramping, bloating, frequent bathroom trips, and abdominal discomfort. When you use plenty of lubrication — which you always should — sometimes you can have loose or runny stools for up to 24 hours after sex; also, if you engage in heavy anal play (for example, using big toys or fisting), you can have some cramping afterward. However, neither of these things should go on for as long as you describe.

It’s also odd that the symptoms don’t appear right away, but several days later which could mean they are not related to the anal sex at all. I suspect that you have an existing gastrointestinal problem and that your anal play is aggravating that condition and causing it to flare up. I recommend you see a gastroenterologist promptly to get to the bottom of your problem. When you do, make sure to be honest about your anal play with your doctor, as it’s important to give health care providers “the whole picture” so they can treat you more effectively.

Feb 272005

I love anal sex — much more than vaginal. I love the pressure just before the head pops in and that little ache as it does. What I am having problems with is that everything that goes in my ass seems too long. It feels almost like the dick or the toy is hitting something inside of me, and it hurts. I have a friend I play with and we do a lot of BDSM scenes, especially rape scenes and punishment-type scenes. He would like to see just how much my butt can take, and I do love the width of everything, especially the next day. Can you help me with the length problem?

–Woodstock Girl

Unlike the vagina, the rectum is not a straight tube. It has a gentle curve, first tipping forward toward the front of the body, then away, then forward again. Everyone’s curves are different, and some are more pronounced than others. As a result, if you stick anything straight inside the rectum, you can wind up hitting the rectal wall, which is not a good feeling for anyone. It sounds like that may be the sensation you described. Have your partner experiment with different positions and angles when he fucks you in the ass, and see if there’s one that allows for penetration without the pain. Toys made of flexible materials are more comfortable and bend easier with your curves; if a toy itself is curved, the curve should be aimed toward the front of the body. All that said, you can also have a short rectum. Since you get pleasure from wide toys, I say invest is some short but wide dildos or butt plugs — go with what works!

Jul 142004

I bought a simple Fleet enema at the drugstore, and I have a few questions. Can I use it as is, or should I replace what’s in the bottle with water? Here’s why I am asking: I like to experience some good hard erotic cramping during enema play. My girlfriend and I often do enemas together, and we like to see which one of us can hold it the longest and who can handle the cramps without showing much discomfort. Is that safe? Because it’s awfully fun.

–Enema Edge Player

When I teach a basic class on enemas, I instruct people on two important points: the ingredients of an enema and the temperature. A Fleet enema (or most other brands you buy at the local drugstore) contains a laxative, and you do not need a laxative. You just need plain, warm water, which is why you should empty the contents of the store-bought enema bottle, rinse it out and refill it with warm water. If you’ve heard of more exotic enemas, with ingredients like champagne, espresso, wine, or other things, beware: these can make you very, very sick. So stick to plain water only.

I recommend that the water be warm so it’s as close to body temperature as possible; usually, the warmer the water, the more comfortable the enema. Most people will have little or no cramping when the temperature is right. Cold water causes discomfort and cramps that most people won’t like. I say most people because I do know enema fetishists who like to deliberately inflict discomfort and cramping on themselves or their partners.

Let me first say that this is considered “edge play” among enema fans, and inexperienced enema givers and receivers should not try this at home. I can tell that you’re a much more seasoned enema player, so I won’t admonish you for your sadomasochistic twist on this intimate form of play. One word of caution: don’t overdo the cold-water, cramp-inducing sessions. You can stress your gastrointestinal tract and disturb the delicate balance of your insides, which is never a good idea. As for you and your partner’s little game, it sounds like a great endurance contest for the BDSM Olympics! Again, a good rule of thumb for all this kind of play: everything in moderation.

Jun 032004

As long as we do lots of foreplay and my body is prepared, I don’t have a problem with pain during anal penetration. However, after about four inches of cock in my ass, I get abdominal pain that I can’t get past, no matter how relaxed or aroused I am. We’ve tried changing positions, but no matter what, it’s as if there is a road block. This is frustrating for me, and I know that for my husband, who wants his balls to slap my pussy on the downswing, it has to be downright maddening. I asked a girlfriend who’s into anal if she had ever experienced this, and she says that around the seven inch mark, her guy seems to hit a wall. Is it possible that there is a sharp bend that is preventing full penetration? Is there a technique to get around the discomfort I am experiencing? Swing to the left? Swing to the right?

–Wanting More

The first two inches inside the anus is called the anal canal, and the rectum is the area from the anal canal to the colon, which is another five to seven inches. Unlike the vagina, where you’ve got a pretty straight shot from end to end, the rectum is curved. That’s especially important to know when penetrating someone’s ass with anything longer than a finger, and especially with a dildo or vibrator that is firm and inflexible (like one made of hard plastic, clear acrylic, or glass). If you jam something (especially something rock hard) straight inside you can absolutely hit the rectal wall, which does not feel good. As you get more turned on, the rectum expands, and the curves are less pronounced, but they are still present.

So, the “four inch” stopping point you describe could correspond with the first curve of the rectum, when it curves toward the front of the body. Everyone’s internal geography is unique, and it’s possible that your rectum is more curvy than others. I’ve heard people report similar feelings of facing a roadblock inside their asses.

You’ve already tried changing positions, which would be my first suggestion. I suggest that you pick a long, very flexible toy, and, while masturbating, begin exploring your ass with it. Take note of the curve of the rectum, what feels good and what doesn’t, and if you can find your roadblock, or if you develop discomfort. Experiment with moving the toy forward or back inside of you to see if that changes anything. If you can find the trouble spot, see if you can move past it or around it, again, by moving it toward the front of the body or toward the back. If you are still experiencing problems, I suggest you talk to your doctor about it and have a rectal exam.

Jan 162004

My Master wants to give me anal training so that I can take a lot of use that way. I am not a virgin, but it has been some time since I have had any anal contact. What would be the best way to do this? He thought that putting a butt plug in me for five minutes twice a day would do it. I have tried this, but have only had problems with it. Perhaps it’s the plug. I am not sure what the plug is made of — it’s a hard-but-flexible plastic on the outside with a different type of plastic on the inside. It hurts when I stick it in, and that’s not helping my ass get properly trained. What should I do?

–Slave Butt in Training

Your Master has the right idea: anal training is a great way to mentally reinforce the Dominant/submissive dynamic as well as physically prepare your ass for extended anal play. I, too, use butt plugs as part of my anal training regimen.

The method I think that works best is to set up a plan for a bottom, where he or she gradually increases a number of elements. First, start with a very small plug and wear it for fifteen minutes. Continue to wear the small plug each day, adding fifteen minutes to the ritual. After a week, switch to a butt plug that’s slightly bigger, and start back at the fifteen minute mark, working your way up for another week. With each week, increase the size of the plug and the duration that you are wearing it. When you reach a large plug, with each new week, instead of changing the size, just up the amount of time you wear it. Use plenty of lube, and, if your Master allows it, play with your clit to make the experience more pleasurable (this will also relax your entire genital region and help you take more for longer). If it still hurts, honor your body’s response and go back down to the smaller sized plug, staying with it until you feel ready for more.

As for the type of plug, toys made partially or entirely of hard plastic aren’t a good idea for anal novices or the beginning of training. I recommend something soft and flexible made of either latex, vinyl, or silicone. Once you’re a pro, then you can move on to bigger, harder, heavier toys.

Nov 082003

My girlfriend and I have tried anal sex multiple times, but she doesn’t like it unless I rub her clit. As soon as I stop rubbing it, she says it’s very painful and wants to stop. She is also afraid to try doing certain anal positions. We only do it lying on our sides, facing the same direction. She claims that doggy style hurts too much from our one time of trying it. I am desperate for help!

–Anal Addict Denied

It fascinates me that you consider yourself an “anal addict denied,” because you are, in fact, having anal sex — just not necessarily in the exact way you want to be. If your wife doesn’t like it doggy style, that’s most likely because that position offers the deepest penetration, and it obviously doesn’t work for her; fucking her in “spooning position” — which you say works for you — may mean less deep thrusting for you, but a lot more comfort for her. If you’re simply dying to do it to her doggy style, then I suggest taking more shallow strokes, and seeing if that feels better.

As for your problem that she doesn’t like anal unless you rub her clit, well, what exactly is the problem? Rub her clit! The majority of women need clitoral stimulation in order to orgasm, and most would say it enhances all kinds of penetration. I know lots of women who can’t take anything in their ass without something working their clit; it helps them relax, get aroused, and it just feels great. If rubbing her clit is difficult because of your body position, then let your wife work her own clit while you concentrate on her ass; that way, it’s a win-win situation.

Oct 232003

After a long night (or weekend) of intense anal play, usually culminating in anal fisting, my ass feels worn out, sore, and sometimes it even stings a little. Do you have any advice for caring for it after such a workout?

–Ass Needs TLC

We’ve all been there: your ass has taken such a good reaming, you feel that you might never sit down again. First, a few days of rest are in order to give your butt a chance to reflect on all the festivities. Next, I recommend a fabulous product that I never leave home without: Preparation H or Tucks brand Hemorrhoidal Wipes, pre-moistened wipes with witch hazel and aloe. I like the Preparation H wipes better because they are about twice the size. Many drugstores also carry the generic or in-store brand which contain the exact same ingredients but is a lot cheaper. They are cool, soothing, and almost immediately calm an itchy, sore, or irritated butthole. They are also great on a well-used pussy!