Aug 202003

My boyfriend and I decided to try anal sex for the first time. We did it for about 5 or 10 minutes. He loved it. I, however, found it very uncomfortable and painful, and I didn’t have very much fun. Although at one point it almost felt good in a way. I want to try it again (he loves the idea so much), but I want to have fun while doing it. I’ve heard such good things about it. Is there anything we can do to make it more enjoyable for me or get me used to it without the pain?

–Clueless and Curious

First, I want to commend you on remaining curious and open to anal sex even after you had a not-so-memorable first experience. Most women have a negative anal de-flowering and never try it again.

It sounds to me like your husband may have made the most common mistake that I hear about: he rushed the process. Unlike your pussy, the ass is not self-lubricating, so you absolutely need to use lube, and plenty of it. I prefer a thick water-based lube that’s similar in consistency to hair gel; thicker lubricants stay wet longer and have a cushioning effect inside the delicate rectum. And speaking of the delicate rectum, your ass is very sensitive and needs plenty of slow, patient warm up to get it ready for your husband’s cock. That means activities like oral pleasure, gentle penetration with his finger or playing with a small butt plug or dildo to start. He needs to err on the side of caution, especially in the beginning, to get your ass used to having something inside it.

Take your time, and make sure you let him know if you want him to slow down or stop. As you relax (lots of deep breaths help), your ass will, too, and penetration should feel pleasurable, not painful. During this foreplay, experiment with adding other sensations to the mix: many women like (even need) clitoral stimulation in order for anal to feel good. Some like to have vaginal penetration or direct G-spot stimulation at the same time. See what works best for you.

Aug 142003

My partner likes anal sex very much, she has had plenty of experience and we practice it regularly. But, despite extended warm up sessions, a lot of lube and communication, she cannot accommodate my penis every time. I am always very gentle and caring. I know that even with the same partner each day is unique and different even if the mood and environment is the same. The situation is even more frustrating for me (and probably for her too) as we have often to stop after the tip of my cock has gotten inside her. It’s almost like some sort of reflex in her body just “rejects” me. What is the best way to achieve full anal sphincter relaxation, allowing an easy and guaranteed penis insertion?

–Patient in Paris

There are no guarantees in life, especially with matters of the heart and ass. It sounds to me like your partner’s body still isn’t relaxed enough which is why her ass is rejecting you. A surefire solution is to increase the amount of foreplay. I suggest more warm up with fingers and toys, plus you should add clitoral stimulation to the mix. Using a vibrator, your hand, or hers to manually stimulate her clit while you play with her ass can increase her arousal and help her rectum expand for penetration.

Once you first get inside her, don’t make any sudden moves. Stay put and give her a chance to adjust to the feeling before you start moving in and out. When she feels relaxed, then start with gentle thrusting, and let her call the shots in terms of speed and depth. Take your time, listen to her body, and don’t put so much pressure on yourself and her to make it happen every time.

Aug 022003

My husband and I have been experimenting with anal sex for a number of months now. We’ve had good experiences with butt plugs, anal beads, and other toys, but when it comes to anal intercourse, there’s always a problem. The initial penetration itself usually goes really well, but for some reason I can’t manage to have sex for any length of time at all. I mean, seriously, three or four thrusts, and I have to stop. It feels almost like there’s a second ring of muscle, farther inside that my husband is hitting when we have sex. Once he gets all the way inside, it’s fine, but when we start moving, he slips out past that ring again, and it hurts when he comes back through it. Am I imagining things, or is that really there?

Most of the time, if I lay still and concentrate, I can manage to relax everything enough for him to get off, but the second I stop focusing and start enjoying myself, everything tightens up again. It feels so wonderful having him inside my ass, I don’t want this to be something we have to give up because we can’t make it work. What do I do?

–Frustrated in Germany

You are not imagining things. What you’re describing makes perfect sense, anatomically. There are two sets of sphincter muscles, the external sphincters and the internal sphincters. For some people, these two rings of muscles are quite close together, but for others, they are farther apart. Both sets of muscles need to relax completely in order for anal penetration to be comfortable and pleasurable. They are like the “gatekeepers” to the ass, and penetration can be painful if you are nervous or tense.

You are doing the right thing by concentrating on relaxing, it’s critical to your enjoyment. You and your husband should experiment first with different positions; as you try several different ones, you can change the angle of insertion, the depth of penetration, and when he’s hitting that inner ring. He also needs to try more shallow thrusts, so that he doesn’t consistently pull out too far, which is obviously painful for you. I think your problem can definitely be solved with some creativity in positions and taking it slower.

Apr 052003

My wife and I had our first anal intercourse on our 20th wedding anniversary. It was great! She enjoyed it and so did I. Three months later, we are still having anal sex and enjoying it. It still amazes me how easy this comes to her. She can relax very easy and has no problem with penetration. Sometimes, after anal sex, if we both do a lot of thrusting, when we are through, my wife says her ass feels numb or throbbing. She says it is not pain, just discomfort. She has no discomfort or pain at all during anal sex. If we just do a short session (like 5 minutes of pumping) she does not have this feeling. We both want to pump longer but without the side effects, if possible. We have tried more lube. Is this a common problem? Can it be worked through?

–Bobbing, Then Throbbing

You and your wife are an inspiration to married couples everywhere! Not only are you still having sex and enjoying it after twenty years of marriage, but you aren’t afraid to try new things, which I think is exemplary. As for your problem, it’s a unique one in terms of all the questions I get asked about anal sex. Feeling numb and throbbing are two very different sensations in my book, so I am going to address them separately.

When you engage in anal penetration, blood rushes to the anal area and it becomes engorged, just like your genitals do when you stimulate those. Because the ass is full of nerve endings and thus very sensitive, your wife should never have a numb feeling; indeed, most people say it’s quite the opposite: their nerves are electrified. If the numbing sensation continues, I would suggest she consult a doctor, because she may have a circulatory problem. As for the throbbing, once the area is engorged and it’s been vigorously stimulated through repeated thrusting, throbbing seems like a natural response. You’ve worked her ass over well, and it’s responding! As long as the throbbing subsides and she doesn’t feel any pain, then I’d say you’re doing a good job.

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.

Jan 142003

I have been an anal lover for years, and I recently met a new woman who has become my submissive. I would love to start her anal training as she has just begun to understand her submissive side, and it really comes out when I even mention doing her in the ass. Here’s the problem: she told me that she had surgery to remove hemorrhoids, so I am concerned. It has been a year and she has a clean bill of health from her doctor. Can we begin to have anal intercourse as well as other fun and games?

–Do-Right Dom

If your submissive had surgery to treat her hemorrhoids, then her problem was probably pretty serious. Many people with hemorrhoids are able to enjoy anal penetration as long as they pay close attention to their butts, and don’t engage in backdoor banging during a flare up. If she feels itching, burning or any discomfort, you should stop at once. But before you do anything, has she talked to her doctor about resuming anal play? I know it can be a difficult or embarrassing thing to bring up with a health care professional, but your submissive’s doctor knows her ass well by now, so he or she is the best person to ask about its health. If the doctor gives you the green light, then progress slowly, use plenty of lube, and err on the side of gentleness to begin. Instruct your submissive to give you post-scene reports about how her ass is feeling, which will give you information about how to proceed.

Nov 262002

My boyfriend and I have been going out for 5 years. My boyfriend wants to have anal sex, but he is very big and thick. He hurts me when we’re just having regular sex. I don’t know why, since I’m 100% wet when we have sex, and it still hurts. We tried anal once but I told him to take it out because it hurt even when he put the head in. I’m just afraid that if we have anal sex he’s gonna hurt me. He says he will go slow, but he never listens to himself. Just before he’s getting ready to cum he starts to do it harder, so I don’t know if I should do it with him or not.

–I Want A Pain-Free Poke

First, I recommend you really focus on extended foreplay before your boyfriend even attempts penetration with his dick. Have him go down on you, rub your clit, use a vibrator, and work your body before getting inside it. The more aroused you get, the better your circulation; blood rushes to the genitals, the body relaxes, the pussy lubricates, and penetration becomes much easier. You say you are 100% wet, but I still really recommend using lube. Lube makes everything nice and slick, and eases penetration whether he’s well endowed or not. You also need to warm up both your ass and pussy with something smaller than your husband’s dick, like his fingers or a smaller dildo or vibrator. Start small and slow, and work your way up. Add another finger or go farther in only when you feel completely relaxed and ready for more. Don’t rush it.

Once you start having intercourse, make sure you are in the driver’s seat. You call the shots about how hard, how deep, how fast. Talk to your boyfriend and make sure he knows when something feels really good and when it does not. Penetration, whether vaginal or anal, should never hurt you. Take the time to make sure your body is warmed up, you are ready, and make sure he’s connected to you so he knows when the time is right.

For some men, in order to orgasm they need to take some very quick hard thrusts, which sounds like it may be the case with your guy. If he simply can’t slow down or when he does slow down, he can’t come, then I suggest this: when he’s ready to shoot, have him pull out. Then you can give him a hand job, he can jerk himself off, or he can thrust against you but not inside you.

Nov 152002

I have had some discomfort since I allowed my girlfriend to insert her fingers inside my ass. I am afraid she might have scratched me. Is this situation dangerous? What treatment can I use to heal if I am scratched?

–Ass Scratch

Since you didn’t specify if the suspected scratch is external or internal, I will give you advice about both. If the scratch is on the outside, you should take extra care to make sure it stays clean in the next week; look at the local drugstore for personal hygeine cloths which contain soothing ingredients like witch hazel. If you believe there is a scratch or minor cut inside your rectum, your body should heal itself, and you should be free of all discomfort within about a week. If you continue to experience pain or if you are bleeding after a few days, then go see a physician.

Let me give you some tips for the future about how to protect yourself without sacrificing your sex life. Whether she has real or fake nails, no matter what the length, your girlfriend should definitely wear gloves when she fucks you in the ass. Latex or non-latex gloves alone are fine for short nails or even when you are just not so sure about rough edges, torn cuticles, or other things which could cause a tear. But for anything longer than very short nails, she can stuff half a cotton ball in each of the finger tips of the glove or wrap her nails in gauze before she slips into a glove. This will protect her nails and, very importantly, your ass from any future mishaps.

Oct 122002

Receiving anal penetration and being sexually submissive has always been the focus of my sexual fantasies. More specifically, I like the anal penetration to be painful. I always imagined it that way and was disappointed when my partner was too gentle at first. He knows me better now, and I have been able to fulfill my anal fantasies with him for the past six months. We usually start with fingers, dildos or plugs, but unlike everything else I’ve read, we use these to make me sore, not to warm me up, and we use as little lubrication as possible. I can only feel totally aroused when it begins to burn, sting, or ache and I feel I want my partner to stop. This particular pain, coupled with some light to medium flogging, is the one thing that makes me really orgasm. I also love the feeling of soreness the next day.

I always recover after a day or so of restraint, but I am now worried after reading more about the dos and don’t of anal sex that over time I could cause permanent damage to myself. I love it so much, and it is so sexually satisfying to me that it would be a problem for me to lessen this behavior. I would like to know if anyone else has enjoyed such rough anal penetration over a long period of time, and if they have or haven’t had any problems.

–Rough Anal Player

Thank you for writing to me. I think it is incredibly brave of you to be so honest about your sexual desires and practices, especially when many people might see them as sick, twisted, and politically incorrect, even fellow BDSM players. I appreciate your candor, and I think that yours is an important letter to print, because I am sure you are not the only one out there. As kinky people who practice all kinds of BDSM, we know that there is a fine line between pleasure and pain, and that line is different for everyone. People who enjoy flogging, spanking, piercing, and other forms of intense sensation play know the high from the rush of endorphins we get, the thrill of pushing the limits of our bodies, and the orgasmic potential of these activities which non-kinky people would see as cruel and painful.

As a community, BDSM players often reiterate ad nauseum that our activities are “safe, sane, and consensual” and we frown upon “unsafe” players. With most forms of sensation play, you can paddle, whip, beat, pierce and cut fleshy, well-padded areas of the body. You should never strike joints, boney areas, areas around internal organs, the neck, head, or face. I think the ass would fall into the latter category as an area we shouldn’t deliberately hurt simply because unlike fleshly parts of our body which may redden, bruise, or bleed but eventually recover completely, the ass is not so resilient. The rectum is quite delicate, which is why sex educators like myself encourage people to go slow, warm the body up, and use plenty of lube. It’s a matter of comfort — I assume that the majority of people do not want to experience pain through anal penetration. Anal sex has long been mythologized as violent and painful for women, and I am attempting to counteract that stereotype by teaching people to have pain-free anal penetration.

Your desire for pain puts you in the minority but that doesn’t mean it is not valid. However, you need to know the risks of your practices. Through repeated penetration with little warm up, no lube, or deliberate roughness, you can scrape or abrade the rectum, develop anal fissures and other ailments, and cause permanent damage to your ass. Permanent damage could mean no more anal play at all, which doesn’t sound like what you want. Yours is a difficult dilemma. I want you to do what turns you on and makes you come, but I don’t want you to hurt yourself or damage your body in the process.

I think you should explore other kinds of play which may produce similar sensations for you, but happen on a less fragile part of the body. But even as I write that recommendation, I realize that part of the turn on for you may be that you don’t want to feel pain in the “safe” places on your body, but in the very places we’re told are too delicate and off limits. You and your partner should explore new ways to approximate the pain sensations while still taking good care of your ass. Adding warm up and lube to the equation will protect your body and won’t prevent you from feeling the burn or the ache, especially with especially large toys. You need to find that unique line for yourself where the sensation is intense enough to satisfy you, but you are mindful of not hurting yourself.

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.