May 132005

Many years ago, I had anal sex with a man I was very much in love with. I am now getting involved in a new relationship. My new lover knows that I have had anal sex before, but he does not know how long it has been. My question is: since I have not had anal sex for a long time, will we have to start from the beginning?

–Going Back to the Backdoor

Besides saying “a long time,” you didn’t specify exactly how long it’s been since you’ve had a cock up your ass. A year? Five years? Ten years? If it’s been more than a few years, then you should start slowly. Begin with lots of foreplay and lube and work your way up to one finger or a slim toy, and don’t go any farther than that. Next time, you can experiment with two fingers. You want to re-introduce the pleasures of buttfucking to your ass in a gradual way.

Don’t think of it as a chore, but instead use it as an opportunity to re-experience the first time you ever had something in your ass. You and your guy can revel in the excitement, the slight resistance, the de-flowering of that tight little hole. Relish each new step when your ass is able to take a little more. The body does have memory, so I suspect that it may take less time to build from fingers to your new lover’s dick, but everyone is different. Listen to your body, honor its boundaries, and take it as slow as you need to.

Apr 172005

I have recently started dating a girl who, like me, really enjoys anal intercourse. Obviously we are at the start of the relationship and are having multiple encounters that include much anal play and some anal intercourse. We are both well versed in all of the basics of anal play i.e. lube, cleanliness, order of entry etc. If we engage in anal intercourse three or four times a week, should we be concerned about long-term damage to her ass due to such frequency?

–Backdoor Couple

As long as you’re following the general rules for safe and pleasurable anal play — go slow, relax, use plenty of lube, work your way up to intercourse — then you’re not in any danger of causing harm in the short or long term. The majority of people who develop health issues because of anal sex combine drugs and alcohol with their play or push their bodies too far too fast. Make sure your girlfriend listens to her body, and if her ass feels sore or tired, then give it a brief vacation; otherwise, have as much anal play as you like. In fact, anal sex can increase circulation to the anal area as well as tone and exercise the anal sphincter muscles. So, the more good butt sex you have, the healthier your butt can be!

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!

Feb 052005

I’m a 21 year old male anal sex lover. First off, I’d like to say that I respect your work a lot. It’s awesome that a woman like you does so much work to turn women on to accepting anal pleasure. With that said, here’s my dilemma. My girlfriend loves anal pleasure, but cannot handle it. When I finger her asshole, and or touch her pussy at all, she says it’s too much. She has to stop me because she says it feels too good, and that she can’t handle it. It is because of this we have never gotten past the two-finger mark. But she wants to have my cock in her ass, and, of course, so do I! I just recently ordered her some new toys, but my question is how can I get my girlfriend to relax? We think we have tried everything short of drugs, which we don’t want to try. How can I get my girlfriend to give in to the pleasure and loosen up? We both really want to get my cock into her ass without hurting her!

–Fellow Anal Lover

The ass is an incredibly sensitive erogenous zone, so it’s not surprising that some women can find anal stimulation or penetration too intense. Believe it or not, the more aroused your girlfriend gets, the more stimulation she’ll be able to take; blood will rush to her genitals and the entire area will get swollen and be more receptive to pleasure. Try to bring her close to orgasm before you play with her ass, and see if she responds any differently. If anal play still feels overwhelming to her, than you may want to investigate the situation further. Sometimes when a person is super-sensitive during sex, there may be an emotional component at work. One more tip: there are a few steps between the two-finger mark and your cock. One of the most common mistakes people make is that they rush penetration which leads to discomfort or pain. If you make it to a pleasurable two fingers, try adding a well-lubed third or try a small butt plug or dildo. When that feels great — and not before — you can consider your cock.

Nov 202004

I’m a guy, I like women, and I’ve never been attracted in any way to men. I want to try anal sex (with me on the receiving end) with dildos and even a strap-on. Does this action means I am gay? I have heard that men can have orgasms by prostate manipulation. How would my wife be able to do this to me? Is there a specific method or do I just hope that she does it right?

–Wanting But Wondering

The idea that men who like getting it up the butt are gay is absolutely a myth, one fueled by our society’s homophobia and misconceptions about anal pleasure. Plenty of heterosexual men enjoy receiving anal pleasure, whether with tongues, fingers, or toys. As I’ve said before, anal sex can be an incredibly powerful experience, but it’s not powerful enough to change your sexual orientation! I think that men who enjoy strap-on action especially have anxiety because of the implication that they are getting fucked by a cock, whether it’s silicone or not. The truth is that it feels good, and when you turn around, you want a woman on the other end of that cock.

Men can definitely have orgasms through anal penetration. The prostate gland is about an inch to an inch and a half inside the rectum on the front wall. So, if your wife slips her finger inside and heads toward the front of your body, she’ll find an area (about the size of a walnut) that feels differently textured than the rest of the rectal wall. She should gently rub the spot as you give her feedback about how it feels. Every guy is different, so your communication is critical to helping her stimulate you in exactly the way you want. As you get more aroused, the prostate will swell and become more sensitive. For prostate stimulation with a dildo (whether strapped on or in her hand), select a curved toy and make sure the curve is always toward the front of your body. Some guys like to have their cocks and balls played with, others want anal play alone — that’s something for the two of you to experiment with.

Sep 222004

I have discussed with my wife the possibility of having anal sex. After a little discussion, she said she would try it. We agreed that if it hurt her too much, I would stop. My problem is I have my penis pierced with an ampallang piercing; that’s a horizontal piercing through the head of my penis. I would probably get stuck in her if I did not pull out before ejaculation, and then I’d lose my erection. Any suggestions?

–Pierced in Pennsylvania

Your question raises many more questions. How old is your ampallang piercing? Most piercers recommend an initial healing time of 8-10 weeks, and say it will be fully healed at 6-12 months. In the first couple weeks, erection or orgasm can cause the piercing to bleed. If yours is fully healed, my next question is, how big is the jewelry? You make it sound huge by saying you’re going to get stuck, and, if it is in fact bigger than about 10 gauge, that would be cause for concern. I have not heard of people with average-sized ampallang piercings getting stuck.

Although I do think you should be concerned that your piercing may tear the delicate tissue that lines the rectum or cause your partner pain. I recommend you wear a condom to prevent possible injury or discomfort. Again, all penis piercings with average-sized jewelry should not interfere with the safe use of condoms. Use a condom with a receptacle end to fit comfortably over the jewelry, and lubricate the inside of the condom as well as the jewelry itself to reduce friction.

Aug 052004

I am a heterosexual married man, and I have been occasionally stimulated myself with a finger during masturbation for years. I recently convinced my wife to try a strap on a dildo and fuck 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 prostrate stimulation can cause orgasm and ejaculation. But for me, even though we reached a point where a modest, 5-6″ dildo was all the way in and being generously worked, I could get just at the edge of orgasm but not quite there.

Not that I’m complaining, because the whole encounter was great. If I was at the same point of arousal and pleasure as I was fucking my wife, I couldn’t have held back. But anally, to put it bluntly, I was able to be buttfucked at that same pinacle of near orgasm delight for as long as my wife could go and I could take NOT coming. The whole time it felt like “just a little faster, or harder, or deeper and I’ll come.” It was incredible, but also disappointing. Am I going to have to have my penis stimulated to get an orgasm, or is it a matter of working up to a larger dildo to hit the prostate?

–Waiting to Come

Before I answer your question, thanks for your testimonial about the joys of being buttfucked by your wife; I hope it serves as an inspiration to all your hetero-male bretheren! This is not a problem of size, I can assure you, because the prostate is just a few inches inside the rectum, so something bigger or longer is not going to solve this quandary. First, I want to encourage you to add cock stimulation to the mix since guys like to be stimulated in both places at once; try working your dick as she fucks you and see if the result is different. Second, you may experience a different kind of orgasm from prostate stimulation than you do from having your penis stimulated manually, orally or via penetration. Many men report that they have all the sensations of an orgasm without ejaculation. So, it may be simply a matter of re-orienting your mind around a different expectation of an orgasm. Third, you may still be able to come and shoot from a good assfucking, and in that case, practice makes perfect!

Jun 302004

I am a thirty year old woman in a D/s relationship. My Master really enjoyed something that I unknowingly did last night. I was in “doggie style” position, and he was playing with my ass from behind. I was very, very aroused and without knowing or trying, I experienced what I have seen you refer to as “the gape.” It turned him on a great deal. I was able to continue this for quite while, even while alternating contracting and relaxing my sphincter muscles. Then, suddenly, I just couldn’t reproduce the gape again no matter how I tried. If you have any information on how I might cultivate or encourage this skill, I would be most grateful.

–Going for the Gape

It sounds to me like you stumbled upon something that other people work pretty hard to achieve! Usually in order to get the gape, you need to be very turned on (as you said you were) and have an extended anal penetration scene to get your sphincter muscles to relax and open up. For some women, having something sizable in their ass for a while is enough to bring on the gape. From the description of your experience, you have a good awareness of and control over those muscles, which can also help you go for the gape. In addition to trying to contract and relax the sphincters, you may also want to try to bear down slightly, and see what effect that produces. Continuous penetration of some kind may be the key to extending the gape for you, since it sounds like, at some point, the banging stopped, and you were just flexing your muscles. If your Master continues to play with your ass, thus stimulating the area, I bet you’ll be able to extend the gape.

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.

Mar 202004

I just started having anal sex with my girlfriend. We did it the first time with lots of lube and I was able to get the entire shaft inside her with little to no pain. She told me that she could feel the fullness but she got no pleasure or pain from it. She said that if I wanted to do it again later it would be no problem since it does not hurt her; however, I would like for her to get some pleasure out of it. I cannot touch her vagina with my fingers because she is very ticklish there. If you have any suggestions, I would appreciate it them.

–Pleasure With My Probe

Bravo to you for realizing that anal sex should be pleasurable for both people involved. My suggestion is that you add some clitoral stimulation to the mix. While you are doing her ass, rub her clit, or, if it’s easier, have her do it herself. You could also use a vibrator for more intense, focused sensation. Many women (me included!) love the combination of clitoral and anal stimulation, and lots of girls say that they don’t experience pleasure from anal penetration without something on their clit.

I’m not sure what to make of your girlfriend’s ticklish pussy. That sounds more psychological than physical to me. Perhaps it’s a reaction to her feeling shy about receiving pleasure; if that’s the case, then you should encourage her to relax and give herself permission to experience being touched and pleasured. Or, it could be that when she’s turned on, her genitals become super-sensitive, and stimulation of any kind feels overwhelming. Then, try softer, more indirect kinds of stimulation, like rubbing her clit from one side, rather than directly on top.