Oct 102011


I have enjoyed anal sex with about 20 guys now. By using lots of lube and following my “3 finger” rule (no cocks enter before at least three fingers have opened the back door), I have not had any pain. If I did, the session would be over, pain is a signal after all. Now my current boyfriend has agreed to my suggestion that he fist me. I told him that I will be calling each step.

My plan is simple. You know those Russian dolls inside of dolls? I will do the reverse of that with dildos: start with a very small one, then work my way up, all the way to the tennis can size. I’d like my virgin fisting to happen at a party with a few other guys watching, that is part of my fantasy. They will probably be in the mood for sex, and I’ll be blissed out and certainly open enough for them. My question is: do some people with the stamina go for anal sex after fisting?

–Ready To Make The Leap

I love your idea of the “3 finger” rule, very smart! It sounds like you’ve got a good plan for your first fisting. I appreciate that you’ll be calling the shots and using toys that graduate in size to warm up. Make sure to use plenty of lube, and don’t be disappointed if it doesn’t happen the first time around; you’ve got to respect your ass and go at its pace.

As for your post-fisting romp, I applaud you sharing your fantasy of a little gang bang after the fist — a combination of two very intense activities. I hate to burst your bubble, but I’m not sure your desire is realistic. Most people I know who are fisted do feel blissed out, but they also feel tired and sore, not exactly ideal conditions for having a bunch of cocks in your ass one after the other. Fisting is a process that requires patience and lots of warm up, and it will most likely leave your ass ready for a few days vacation, especially your first time. I suggest you try to rework your fantasy and see if you can come up with some alternatives. Maybe they can all watch then fuck your pussy or get blow jobs from you; use your imagination which shouldn’t need much coaxing. I’m not saying your fantasy is impossible, but until you get a lot more experienced with fisting, take it one step at a time.

Oct 012011

My girlfriend and I have been dating for over three years. When we first started dating, she let me fuck her in the ass a couple of times; she never had an orgasm during anal sex, but I know she enjoyed it. We always used tons of lube (generally Astroglide), I always went very slowly, and my cock is a pretty average 6″ long and not too thick. Then, one day, I was forbidden to enter her ass. I have played with her ass and licked her ass while I’m going down on her. There is no doubt that she enjoys this and if I finger her ass at the moment of orgasm it almost always pushes her over the edge.

A month or so ago, she said we could try anal sex again, which we did several times, again using lots of lube and going very slowly. She never complained that it hurt, but she said at times it made her feel nauseous. She seemed to be more focused on getting through the act rather then trying to enjoy it. I tried to get her to play with her clit to enhance her pleasure, but she just wanted to get through it. Then she stopped the anal sex again.

I’ll be the first to admit this is my idea, I think I have a bit of an ass fetish. I really want anal sex to become part of our sex life, and not only for me, but because I know she enjoys it… if she lets herself. There is no doubt in my mind that her aversion to this is all mental; she’s a “good girl” and thinks anal sex is something that she shouldn’t enjoy. She isn’t totally adverse to anal play as she admits that sometimes she does like it when I finger her ass and she will sometimes finger my ass during a blow job or a hand job.

First, what can I do to put her mind at ease and let her know that it’s okay to enjoy anal sex and she’s not a freak for getting pleasure from her ass? Second, is there any way to ease the feeling of nausea?

–Help Me With Her Mind-Body Issue

I want to address the nausea first. It’s not unheard of for someone to feel nauseous during or after anal sex. Because anal sex stimulates the rectum, it can also stimulate the colon and intestines, giving someone a mild stomach ache. She should avoid eating a meal right before anal sex. Some positions, like doggie style with her ass up and head down, may exacerbate the problem, so you can experiment with different positions to see if some ease her discomfort.

As for easing her mind, well that’s a lot trickier. First, it sounds like the two of you need to have some better communication about sex. Her abrupt stops to anal sex seem to surprise and confuse you, and you need to ask her why she has put the kibosh on it several times now. It also seems like anal play is okay with her, but anal intercourse is not, and that needs to be addressed. It’s troubling that you believe she wants to get through it rather than enjoy it since it sounds like you’re doing all the right things to make it pleasurable for her. If, like you think, this is “all mental,” then communication can also help her talk through some of her issues. Many people have hang ups about their ass and anal pleasure which are based on myths and stereotypes. She needs to let go of her judgment of herself and of her feelings that some sexual things are normal and others aren’t. If she feels kinky or perverted for having anal sex, assure her that lots of people do it and it’s just another form of pleasure. The tricky part is that she needs to believe you, which you can’t make her do.

I would also encourage you to explore why she has trouble letting go or being vulnerable during sex, because that may be a component of what’s going on. Open up the dialogue and be as encouraging and non-judgmental as you can; help her to figure out what her issues are and how to work through them. If she’s open to it, you might want to also try couple’s counseling with a therapist who has experience with sexual issues.

Sep 292011

My boyfriend and I started trying out anal sex a few months ago and we both really love it. He always makes sure I’m ready to take him and that I orgasm really hard from it. But lately when he slips into my ass it feels as though someone has just thrown me into a tub of ice. I get covered in goose pimples and it’s really unpleasant. The freezing cold feeling is worse when I am kneeling on all fours and he fucks me from behind. Have you ever heard of this before? How can I stop it so I can get back to loving anal sex again?

–Shivering in the South

In all my years of answering questions about anal sex, I’ve never gotten this one. So, I did some research about the phenomenon you described, including talking to a doctor. She had three theories about the experience.

First, your core body temperature can increase during any kind of sexual activity, and that increase in temperature could cause mild chills, but would not necessarily give you the extreme cold feeling you describe. Second, have you experienced any sexual trauma or abuse? Sometimes, we can push traumatic things out of our consciousness, but they rear their heads as our body responds in bizarre, unexpected ways. You did not indicate anything about that in your letter, but it may be a possibility.

Third, and most likely if there is no history of trauma, is that your vagus nerve is the culprit. The vagus nerve begins in the brain stem and extends through organs in the neck, chest, and abdomen all the way to the upper part of the transverse colon. It affects many areas of the body, including the heart, lungs, stomach, ears, pharynx, larynx, trachea, and esophagus; it is involved in many body functions, like breathing, blood circulation, heart rate, gastrointestinal peristalsis, and the regulation of body temperature. Anal penetration stimulates the rectum, which in turn stimulates the colon, which, for some people, can stimulate the vagus nerve. Stimulation of the vagus nerve can cause a variety of effects in different people, and in your case, the vagus nerve is sending a message to your brain that something unusual is happening; yes, the vagus nerve can be that unspecific. The brain responds by telling your body it’s cold, and you get your ice bucket sensation.

The important thing to know is that you’re not in any danger, this is just how your particular body responds. If it’s worse in doggie-style position, I suspect that’s because he’s probably deeper inside you then, closer to the lower colon, and more likely to affect the vagus nerve. I recommend you experiment with different positions, to see if you can find one that feels better. You can also teach your body to react differently. For example, some people faint at the site of blood, but can learn to overcome it by deep breathing, rationalization, and learning how to cope with the fear it raises in them. You can also learn to override the reaction; think of it as “mind over vagus.”

Sep 272011

I’m a guy, and over the years, I have occasionally anally stimulated myself with my fingertip during masturbation. I recently convinced my wife to try a strap on with me. As I expected, I enjoyed both the physical stimulation and the psychological joy of giving myself up to her as the penetrator. But try as we may, the buttfucking could not get me to orgasm. I have heard that direct prostate stimulation can cause ejaculation and orgasm. Even though we reached a point where a 5-6″ dildo was all the way in and being generously worked, I could get just to the edge of orgasm but not quite there. It felt incredible, but it was also a little disappointing. Is it a matter of working up to a larger dildo?

–On The Edge

You heard right: direct prostate stimulation can lead to a great deal of pleasure, orgasm, and ejaculation. The prostate is only a few inches inside the ass and toward the front of the body. With a 5-6″ dildo, you’re definitely going to hit it, and a longer toy is not the answer. You may want to try a curved dildo for more focused prostate stimulation (and aim the curved part toward the front of your body) and see if that makes a difference. If you have masturbated with anal penetration to orgasm, then the combination of the two may be what your body is most used to. Add penis stimulation as she fucks you to help you over that edge to orgasm.

Photo: Annie Cruz and Nomad in The Expert Guide to Anal Pleasure for Men

Sep 252011

I started doing anal play about 10 years ago. At first, it was somewhat uncomfortable, but I persisted, and my persistence paid off. I am now able to take a 10″ long dildo with a wide circumference. I thoroughly enjoy it, but I wonder: how deep can you go? Once, I tried a longer toy. After about five minutes of working it all the way in, I took it out, and there was some blood on the dildo. I went to the bathroom, but there was no more blood. It shook me up big time, so I didn’t insert anything for a week for fear of hurting myself. After my hiatus, I didn’t feel any pain and went back to playing, and it felt good. But that blood thing scares me — did I reach my limit?

–When Should I Say “When”?

If you’ve ever seen a porn video of someone taking a huge cock, a giant dildo, or even a fist (and beyond the fist!) up her or his ass, then you know that the butt is capable of a lot. The rectum has the ability to expand a great deal, but remember that it is still quite delicate. Even with plenty of lube and warm up, you can still have a minute cut in the lining of the anal canal or rectum. The longer and thicker the thing penetrating you is, the higher your chances of having one of these small tears. It’s only natural that when we see blood, it’s scary.

You did the right thing: you gave your ass a vacation from penetration. As long as there is only a small amount of blood, and it goes away within about a day, then your ass is on the road to healing itself. However, use common sense. If your ass is bleeding, you feel pain or serious discomfort, then you should see a doctor.

Sep 232011

I have had anal sex with many women. I always make sure my partner is relaxed, use my tongue and fingers, use lube, etc. I have turned many women who hated even the thought of anal sex into women who really enjoy it. If they don’t already know, I also make sure to educate them about how to clean the their asses. Here is the problem: it has been quite some time since I have had anal sex with a woman without it getting messy. It’s not that bad, and I always make sure the woman knows that it is okay — but I wouldn’t mind some cleaner encounters. I have an average size penis but above average stamina. I don’t know if either has anything to do with what has been going on, but I include it for completeness. Can you help me?

–Good Clean Fun

Well it sounds like you’ve been a model anal sex partner, and you deserve some good clean fun. Your cock size and stamina have nothing to do with your messy encounters. You did not specify what you tell your partners about cleaning their butts, and your advice in this area may be the problem. If someone buys a plastic bottle enema (like a Fleet brand enema), she should empty the contents of the bottle and rinse it thoroughly. Then she should fill it with plain warm water. A common mistake people make is to use this kind of enema right out of the box, but the bottle contains a laxative, and most people do not need a laxative. The bottle enema is like a douche and will clean the anal canal and lower rectum; for a deeper clean, she should opt for an enema bag, also with plain warm water only. Whichever she chooses, she should do her enema at least two hours before your anal sex date. This will give her body time to recover and to make sure that everything that was loosened up has flushed out of her butt.

Nov 302005

I am very into anal play: rimming, butt plugs, and especially anal beads. However, I have some apprehension about penetration with a cock. A friend of mine who indulges in anal sex had told me that it made her ass, well, looser. In other words, it didn’t leak, but she found that the initial penetration of various objects became easier after she started doing anal. I am concerned that if I start indulging in penetration with a penis, that it will become noticeably easier to insert other non-human objects.

In particular, I’m concerned that my husband will start to notice because I currently have a lover on the side to satisfy my other needs (primarily BDSM). I am worried that if I start to let my lover fuck my ass that my husband (who is way too big for anal penetration) will notice and suspect something is up. What advice would you give me to let me have the cock and not get in trouble?

–Want to Have My Cake and Eat It, Too

Your friend who regularly has anal sex and now finds penetration easier is a little confused. Penetration done right will not make your ass looser or result in you losing control of your bowels—that’s a myth. However, it will make subsequent penetration easier, but not because you’re all stretched out. The more experience you have, the more you get used to relaxing your anal sphincter muscles and the easier it is to accommodate bigger toys or penises.

I think what you’re asking is: if I have anal penetration with a cock, will my husband be able to tell that I am having an affair and getting regularly buttfucked? The answer is: it depends. Will he be able to tell that you’re getting fucked in the ass just by looking? No. Will he figure it out if he plays with your ass? Well, he will probably notice that your ass can relax and open up easier and in less time than before; whether that causes suspicion or not really depends on him and your relationship. While I support people having multiple partners to meet their different sexual needs, everyone needs to be on the same page. Your husband has not consented to this other relationship, which isn’t fair to him. Ultimately, I can’t really condone cheating, nor can I offer any tricks to help you not get caught.

Nov 142005

My wife seems to like the naughtiness of receiving my dick up her ass, but I don’t think she really likes it. We haven’t done it that much, but when I get it in there she does her sexy groan like when she’s going to come from a good licking. Part of it is we haven’t used much lube except her cunt juice. I don’t know if I really want to ask her if she wants to have it or not because she may say no, and I don’t want to go there. We’ve talked about it outside of the bedroom and she says she does it because she knows it turns me on and she likes to submit to my power over her. She’s very much in tune to her body and loves trying new things. Any advice on getting her more into it?

–Can’t Read Her Mind or Her Ass

Before you think about getting your wife “more into” anal sex, you need to figure out if she is into it at all. Although you’ve talked with her a little bit about the subject, you need to talk about it a lot more. She says she does it to please you, but does she enjoy any other aspect of it besides the pleasure it brings you? It troubles me that you have avoided asking her direct questions about it for fear that her answers might not be the ones you want to hear. You both need to be honest with one another about your desires and needs when it comes to anal sex.

As for the lack of lube, well, that’s not helping matters. You absolutely need lube for penetration to be comfortable for her; in this case, her cunt juice is not enough. But first and foremost, her desire must be there for it to work at all.

Oct 232005

I’m just starting to explore my butt with my partner and we’ve got hung up on the how and where of lube. Obviously, I know I need plenty inside for comfort, but how do I get it there? I mean, does it go on his penis? If so, doesn’t it all just rub off at the anal opening? How does it get where it needs to go?

–Lube Novice

The basic rule of thumb with lube is ‘on’ rather than ‘in.’ So, lube should coat whatever it is that’s going inside you (a finger, a toy, a cock), and you should reapply it as you need more or it dries up. Trying to pour lube into an orifice doesn’t really work very well. Although, you can dribble some lube at the anal opening, and “push” it inside with the tip of a finger, dildo, etc.

If you feel like you’re still not getting enough lube where you need it to be, I suggest a few tools. The Lube Shooter is a disposable hard plastic syringe with a flared base that you fill with your desired lube (a process that can be a little messy). Insert the body of the syringe in the ass, push the plunger, and voila, lube right where you want it! Also disposable and easy to use, the Astroglide Gel Shooter is a prefilled flexible rubber tube of lube with a long neck that can be inserted into the anal canal (after removing the tip, of course). Squeeze the tube, and lube goes into the ass. You can also fill up a plastic irrigation syringe (found at drugstores) or a stainless steel enema syringe (available at specialty stores) for the same purpose.

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.