From Painful to Pleasurable: How to Maximize Enjoyment and Safety During Anal Play

Today, as our social capacity to discuss sex and pleasure is expanding beyond what it used to be. After all, this is not your grandma’s generation. While we still have a long way to go, important discussions on sex are evolving to include maximized pleasure in ways once seen as taboo. At the forefront of the sexual revolution circa 2008 is the discovery of the anus; that erotic pleasure center filled with sensitive nerve endings so easily forgotten amongst negative myths and stereotypes. Anal play can be an immensely stimulating activity which can maximize orgasm, compliment other types of play, or even provide for new and exciting possibilities experienced individuals never knew existed. Unfortunately, however, if done incorrectly and without the proper precautions, it can become a painful and physically harmful activity. Below, I’ve included some of the best tips and tricks for everyone, beginner or advanced player, male or female, top or bottom, to allow for anal stimulation and sex to become the next greatest thing which ever happened in your bedroom (or bathroom stall, or kitchen, or stairwell, or cubicle?). Looking for more? A selection from Tulip’s fabulous bookshelf is included at the end of this post.
So without further adieu, here is the skinny on pleasurable anal play a la Tulip’s very own sexual health educator, Holden C.

#1: Clean yourself!
The #1 deterrent to anal sex remains the fear of it being messy, smelly, and awkward. After all, we do expel waste out of our anus! While most fecal matter is not stored in the rectum itself (except before expulsion), small amounts of residue may still be present. While it’s simply a fact that in anal play “shit” sometimes hits the fan, there are steps to decrease the inevitable. Regular and relatively noninvasive cleaning during a shower or bath should be sufficient (a little water should do the trick). Additionally, regular bowel movements should keep you clean and empty. When washing, be careful of soaps and other cleaners, as they could potentially induce a nasty infection. For those who want a deeper clean, consult a reference on douching. If done correctly, it can be a safe and even pleasurable way to leave you feeling minty fresh, but if done wrong, can lead to massive and uncomfortable trauma to the anal lining. Lastly, don’t stress too much about your degree of cleanliness, most experienced players simply recognize it as part of the process.

#2: Slow Down Baby, It’s Not a Race
The anus has the remarkable ability to stretch and expand to accommodate just about anything (after all, experienced fisters can take a whole forearm). But that’s not to discount the fact that in their natural state, the anal muscles (in particular the inner and outer sphincter) will be tight. Too often in anal play, particularly with anal sex or toy play, people try to “ram it in” too fast and too hard. Remember, taking it slow will help facilitate the stretching and relaxation of the muscles needed to accommodate any object, from a finger to a penis. Slowing down will also maximize the amount of friction the nerve endings around the anal opening receive, increasing pleasure. The more they’re stimulated, the more fun. Most importantly however, taking it slowly reduces the chances of the ripping of the anal walls, and even the collapsing of the anal cavity. This, therein, reduces the chances of HIV and STD infection, and decreases the risk of damage if a condom is used.

As mentioned in tips one and two, the anal muscles are naturally tight and rigid. In order to accommodate large objects like a penis or finger they must be relaxed completely, and given an opportunity to expand at their own pace. There are a variety of ways to relax the muscles, but the most important remains comfort levels. Experienced players will learn how to cognitively control them, but it comes with much practice. Beginners should try some basic steps, most importantly, having a level of physical and emotional comfort during play. This extends to position (on your back, on your stomach, squatting etc.), environment (in your bedroom, shower, kitchen to name a few), partner (alone or with someone you feel comfortable with who will be patient as you as you adjust), and your life circumstances (if your mind is busy with outside stressors maybe its not the right time). Beyond the basic tips above, it’s also important to remember a bit about patience. Anal intercourse is a process, and is a bit more complicated than bending over and sticking it in. It takes concentration and communication between partners to make sure both are maximizing their pleasure. A note to tops: it’s important that you be conscious of your partner throughout anal play. Ask if they hurt, or if there is any pain. Look and listen for visual and audible clues that could warn you of any discomfort they are not informing you of. Remember that not relaxing the anus will increase the chances of rectal bleeding, which therein increase the chances of disease transfer, thus it’s in your best interest to be careful!

#4: Get Slippery
Lubricant remains the most important and integral piece to any anal play. Using enough lube will decrease pain and increase pleasure by allowing for more fluid and consistent movement for everything from a finger to a penis or toy. A “spit shine” (i.e. using saliva instead of a manufactured lubricant) is not recommended, as it will not reduce enough friction to be pleasurable or safe. Because the anus does not lubricate itself as the vagina would, it’s important to use plenty, and reapply as soon as you feel it drying. Not sure if it’s enough? USE MORE! There’s no harm in using a bit too much lube, but there are definite and serious implications in using too little. Try using thicker, more long lasting lubes, although thinner ones like Pjur will work as well. For anal play, Tulip highly recommends Liquid Silk and Maximus (both water-based), and Pjur and Gun Oil (both silicone-based). Remember, if toy use is going to be a factor, use water-based lube, as silicone-on-silicone contact will degrade the product.

#5: Experiment and Go Exploring
There is much more to the anus than simple insertion of a penis or dildo. First and foremost, the anal opening is a virtual pleasure center with a high concentration of nerve endings. A simple massage will yield fantastic results. Try giving just light pressure to the opening for a sexy teasing sensation. Rim jobs (a.k.a. analingus, or oral-anal contact) can also provide for amazing pleasure, even orgasm (those wary of coming in contact with the anus can use either a dental dam, or a condom carefully cut open lengthwise). Men can stimulate their prostate with either a finger or a prostate massager (check out Tulip’s collection here: Feeling even a bit more wild and crazy? Experiment with a vibrator both in and around your anus. You may not have known what you’re missing.

Anal play can be stimulating, erotic, fantastic, and orgasmic if done with proper care and precaution. Unfortunately, mature and important discussions are truly lacking on what the realities are. Feel like you still need more information? Stop by a Tulip Toy Gallery near you (located in both Lakeview and Andersonville in Chicago) and chat with one of our fabulous employees. In addition, below is a list of some of Tulip’s favorite and most informative literature on anal play.

Best of luck,
Holden C.

A note on desensitizers: use them wisely, or not at all! One important reason that our bodies give us pain responses is to inform us of potential harm. Yes, some pain can also be pleasurable, but when engaging in anal intercourse it’s particularly important to be conscious of the responses your body is giving. If you choose to use a desensitizer, do so wisely, and use as little as possible. When desensitized, be extra careful of what your body is telling you, it may no longer be using pain as a method, but it will still be responding.

Get Literate: Book Recommendations
-Anal Pleasure & Health: A Guide for Men and Women by Jack Morin (probably the best book I?ve seen yet on anal play)
-The Ultimate Guide to Strap-On Sex: A Complete Resource for Women and Men by Karlyn Lotney a.k.a Fairy Butch (fantastic for adventurous heterosexual couples, as well as lesbian couples beginning their adventures)
-The Multi-Orgasmic Man: How Any Man Can Experience Multiple Orgasms and Dramatically Enhance His Sexual Relationships by Mantak Chia and Douglas Abrams (great book regardless of type of play, but some fantastic tips and tricks for anal intercourse and exploration)
-The Ultimate Guide to Anal Sex for Women by Tristan Taormino
-The Ultimate Guide to Anal Sex For Men by Bill Brent

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