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.

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.

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.

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.

Sep 052005
 

My girlfriend has an insatiable appetite for sex. We often have it once a day, and, if not, she masturbates. We both enjoy anal stimulation and have a collection of varying size toys. However, my girl uses them daily. Can someone have too much anal sex or anal toy play? Is it okay to do it almost every day?

–Backdoor Fan

You’ve got one of those problems that lots of other readers wish for! It is absolutely safe to have anal penetration every day as long as you are doing it safely and responsibly. That means: plenty of warm-up, lots of lube, and stopping if you experience any pain. The key for your girlfriend is to listen to her body. As long as everything feels good, she doesn’t rush the process (which even experienced players can do), and she takes a break if she’s sore, she will be fine. Obviously, if she starts to experience anything significant, like cramping, bleeding, or discomfort, she needs to stop and see a doctor.

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.

Jun 302005
 

My fiancé and I have been exploring BDSM, which we enjoy fully. He wants to have anal sex with me, and although it would be the first for me, I’m willing to try it out at least once. He does have a really big penis — gloriously big — and I’m concerned about the process as I’m a small woman. Is there anything I can do to prepare myself for him and make this enjoyable for both of us?

–Tiny But Tempted

Your physical size does not necessarily correlate with your ability to take a “gloriously big” cock up your ass. I’ve seen women who are five feet tall and 98 pounds with very large things comfortably nestled in their behinds. It’s more about your internal than your external size. Like the pussy, the ass has the ability to expand when you’re aroused. Plus, the rectum is longer than the vagina and therefore can usually accommodate something bigger.

However, since your guy is larger than average, it means that you’re going to have to work your way up slowly. And since it’s your very first anal adventure, his cock should not go into your ass all in one evening. Instead, I recommend that you begin playing with a finger or a slim toy either alone or with him. Use plenty of lube, go slowly, and stimulate your clit. When you’ve practiced a few times with the one finger/small toy, and it feels great, you can move on to two fingers or a slightly bigger toy. Again, you can play together or you can add anal play to your masturbation. The important thing is not to rush the process. Find a dildo that’s “one step down” from your man’s cock. When you’ve worked up to taking that dildo, and it’s comfortable and pleasurable, then you can try his cock. Make sure he goes very slowly, and that you give him lots of feedback about how it feels. If you both take your time and let your ass set the pace, it will reward you in the end!

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.