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Beginning Butt Play Made Easy
by Tristan Taormino

Tristan Taormino is the author of several sensationally sexy and informative books including Down and Dirty Sex Secrets, Pucker Up: A Hands-on Guide to Ecstatic Sex, The Ultimate Guide to Anal Sex for Women. From college campuses to sex toy boutiques she tours the country touting the wonders of anal sex and the overall goodness of sex in all its frisky forms. In the Anal Advisor columns, first published in the Village Voice, Tristan addresses the ifs, ands, and butts of anal sex.

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Dear Anal Advisor:

My boyfriend and I have tried anal sex a couple of times, and each time it was very uncomfortable. I know anal sex isn’t supposed to hurt (and when we try, it usually doesn’t), but I don’t like the way my ass feels—like having to go to the bathroom really bad. Do all people feel this during anal sex, and is there a way to do it without the discomfort? Although I am not opposed to anal sex, I do not find it nearly as stimulating as vaginal sex. Is it possible that my state of mind affects the whole anal sex experience?

Signed,
S.N. (via email)

Dear S.N.:

I am so glad you wrote to me because your questions and concerns are some of the most popular I receive via mail, on my web site, and at my anal sex workshops. You are absolutely right that anal sex is not supposed to hurt, and if it does, that’s your body’s way of telling you, “This isn’t working right now!” If you feel pain, you should always listen to your body and stop. Your overall arousal, plenty of warm up and foreplay, lots of lube, deep breathing, and relaxation can all help counter pain and turn it into pleasure (which, of course, is what we all want out of anal sex!). I realize that there is a fine line sometimes between pain and discomfort, and each person is different. You need to judge for yourself where that line is.

Your letter indicates that it’s not pain you are feeling, but discomfort. Let me say right off the bat that discomfort is common, especially to anal sex beginners. One of the reasons you, and many first-timer anal receivers, may experience discomfort is simply because your body is experiencing something new. Many people tell me they have the urge to have a bowel movement during anal sex; well, I recommend you stop and go to the bathroom. You may, in fact, have to go. But it’s more likely that your body is just a little confused. Our rectums are used to expelling things, so when the rectum feels something inside, it sends a signal to the brain to shit it out, which is what it normally does. The next time you feel like you have to have a bowel movement, I recommend you take several deep breaths, relax, and let your ass get used to whatever is inside it. Make sure that the finger, sex toy, or penis inside you stays put and doesn’t make any sudden movements. Chances are after you relax, that initial feeling will subside, and you can progress onto anal pleasure. Remember too that the more you practice anal penetration—with lube and warm up—the more your ass will get used to having things inside it, and will respond with less confusion and more pleasure.

In the end of your letter, you raised another important issue which is how your ambivalent feelings about anal sex may be affecting your experience of it. Your point is a good one: if you aren’t wholeheartedly gung ho to get your ass fucked, those emotional and psychological feelings will absolutely have an impact on your physical experience. Desire is a key ingredient to hot, satisfying anal sex, and if it’s missing, you can experience tension, discomfort, and pain. You may be harboring some unresolved issues about anal sex. Most of us have grown up with myths and misinformation about this taboo subject: it’s dirty; it’s not normal; it will cause irreparable damage. Sometimes simply getting correct information (like in my book The Ultimate Guide to Anal Sex for Women and Jack Morin’s Anal Pleasure and Health) can counteract any negative feelings. Now, there is also the possibility that you aren’t a backdoor girl, anal sex just isn’t for you, and you should respect your own desires. It would make this backdoor girl sad, but to each her own!

Dear Anal Advisor:

My boyfriend would like to insert a butt plug and have me wear it overnight. Is it safe to do so?

Denise, New York, NY

Dear Denise:

I assume that you and your boyfriend are experienced anal players if he’s cooked up this little plan for you. I’d like to address your question and also talk about wearing butt plugs in general for readers who may be less experienced. For many people, the feeling of fullness one gets from having a butt plug inserted is highly pleasurable, and some like to extend that pleasure for various lengths of time. My friend Susan wears a butt plug on long traveling excursions by car and train; she says it makes the time go faster. I know another woman who likes to wear a butt plug out on a date, in order to begin foreplay over dinner at a restaurant. Through each course of the meal, she is reminded of her ass, and with every shift in her seat, she prepares her ass for bigger things to come. I’ve also heard of plug lovers who like to wear a butt plug out in public just for the hell of it. These folks carry on everyday activities with a big smile on their faces. They like the feeling that they know something the rest of the world doesn’t. They are having a naughty sexual experience in public that no one else knows about but them!

Wearing a butt plug out in public or for an extended period of time can be hot, fun, and sexy, and here are a few tips to make it even better. First, you should work your way up slowly. Begin by wearing a butt plug for a half hour, see how it feels, how you like it, what works and what doesn’t. If your thirty minute excursion goes well, try an hour next time. Continue building up the amount of time (in reasonable increments) that you wear the plug. Like anything else you put in your ass, the butt plug should be well lubricated. You may want to consider taking it out every hour, re-lubing it and re-inserting it. Some of you purists may consider this cheating, but keep in mind that the lube will be absorbed by your body eventually, and the plug may get uncomfortable. You have a number of options when it comes to making sure the plug stays securely in your ass and won’t fall out. You can purchase a butt plug harness which looks very similar to a dildo harness and does the job quite nicely. Sometimes a very tight pair of underwear, briefs, or a thong will keep it in, depending on the size of the plug and how strong those sphincter muscles are. My girlfriend loves to make a rope harness for me that runs between my legs. When I move, the rope rubs against both the plug in my ass and my pussy giving me a double sensation I just love. If you do use rope, make sure it’s not too tight and that it’s soft rope that doesn’t chafe or burn. Don’t make complicated knots that are not easy to remove in case you have to do it in a hurry.

Wearing a butt plug for a long time won’t block anything unless you need to have a bowel movement, and then (common sense) take it out, go to the bathroom, and you can put it back in. Finally, on to your question about wearing a butt plug overnight. If you are very experienced with wearing butt plugs for long periods of time, I say, go for it. Make sure to use lots of lube, and you should probably take it out first thing in the morning when you wake up!