My girlfriend and I really like anal sex. We do not use condoms out of personal preference and we use KY Jelly for lube. I usually come in her ass, and it always used to be fine. She would get “the runs” for a day, maybe two, but would be fine after that. It worked perfectly for two years, but recently it’s taking longer before she’s back to normal again. Plus, the outer part of her ass becomes sore afterwards. Is there anything we can do?

–Runny in Reseda

When it comes to your ass, what goes in must come out. When you introduce lubrication (which is a must) into her butt, only some of it will be absorbed by the tissue of the rectum. The rest of the lube is likely to mix with her stool; add your ejaculate to the mix, and the next bowel movement she has will be loose or runny. KY Jelly, like many water-based lubes, contains glycerin, which may be exacerbating the situation. Glycerin can draw water into the stool to stimulate evacuation (that’s why some constipation suppositories contain glycerin).

So, you may want to experiment with a glycerin-free lube like Maximus Lube, which is water-based, or any silicone-based lube. If her anus is irritated after anal sex, I suspect it’s because of the diarrhea she’s having; I recommend witch hazel wipes, which you can buy at any drugstore (they are marketed as Hemorrhoidal Wipes, but they’re not just for hemorrhoids), and some Vitamin A & D ointment — both soothe a sore ass.

 

I have a very free relationship with my girlfriend. She will let me fuck her ass about once every two months, and that is enough for me. She will let me eat her ass whenever I want to. I love to do it, and she loves to have it done even more — she starts to drip because she gets so wet. I love it when she shoves a finger or two into my asshole. She would never consider eating my ass, as I have asked her many times, but I am okay with that. Lately, I have enjoyed eating her ass more and more; it is all I think about.

Yesterday, she came over to my apartment and we laid in bed and had dinner. We got naked and she rolled over to turn off the TV. I saw her ass and pushed her over completely and I got my face to her ass, which was clean, but had an odor, not a bad one, but faint. It turned me on so much that I told her to stay like that and I licked her slightly smelly ass for thirty minutes, while she fingered herself. It was such a turn-on. I told her how much it turned me on and how I wanted to do it again and she said, “No, you are really fucked up.” All I know is that I have never been more turned on in my life. What should I do?

–Want My Nose Buried in Her Ass Forever

Some people like the smell of asses (and other body parts or body odors) — they like reveling in the scent, fetishizing it, and/or talking about it — and it seems like you are one of those people. Scent is an incredibly powerful sense and one that can be closely linked with our desires and turn-ons. It sounds like while you were rimming her ass, she was enjoying herself, since it went on for some time and you wrote that she was pleasuring herself.

I assume that once you revealed that her ass smelled a little, it freaked her out, which caused her abrupt response. One of the most common hang-ups people have about their butts is cleanliness and hygiene, so it’s not surprising that she reacted to your comment. My guess is that she felt self-conscious and instead of admitting that, she lashed out at you. Now that you are past the heat of the moment, it’s time to talk about this openly. You need to stress to your girlfriend that, as you said, her ass didn’t smell awful; explain to her why you liked the smell and how much it turned you on. See if she can get past her own issues and “go there” with you, so you can be open about your desire, and you can both enjoy yourselves.

 

The first time I tried anal sex was almost six years ago but it was EXTREMELY PAINFUL. I want to try anal again with my current partner. It gets me hot thinking about it with him, but when it comes to doing the actual deed, my butthole it closes up and nothing will get through. Seriously, it locks up tight — not even a finger will fit. I’m at a loss because I don’t know what to do to loosen up.

–Want to Get Loose

You and your ass were traumatized during that first negative experience, and you need to realize that it takes time to heal from any trauma. It sounds like you have a partner you trust and you’re enthusiastic and open about giving anal sex another shot, but your body hasn’t quite caught up to your mind.

I recommend that you very slowly begin to introduce anal play into your solo masturbation routine. Start with external rubbing or a vibrator on the outside only. When you are ready, really take it slowly. Try one finger or the slimmest toy you can find. Give yourself the time and space to explore anal play on your own, so it will take the pressure off doing it with your partner. When you feel comfortable, you can try it with your partner, but you need to take it just as slowly as you did on your own. Make an agreement with your partner that you’ll be the one to call the shots (or call it off if need be). Focus on your desire and trust to help you move past the fear and anxiety and toward pleasure.

 

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.

 

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.

 

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.”

 

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

 

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.

 

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.

 

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.

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