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Sex with Dr. Jess


August 24, 2018

All About Anal

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If you’re curious about the butt and its potential for pleasure, tune in for lessons in anatomy, pleasure, technique and more!

For more anal sex tips, check this out!

This podcast is brought to you by Desire Resorts.

Podcast Transcript

Anal Play

What! what! In the butt!

Your bum is one of the most responsive erogenous zones on your body, so exploring its pleasure potential is a no-brainer. Not only is the anus rich in super-sensitive nerve endings, but it is actually anatomically configured for mind-blowing orgasms for both men and women: the male G-Spot, also known as the prostate, and the female cul-de-sac, that sexy region on the lower vaginal wall, can be stimulated through the back door.

Despite the climax-centered design of the bum, anal sex continues to retain its taboo status…at least in theory. In reality, however, anal sex is quite common. Research suggests that nearly half of men and women have engaged in anal intercourse and orgasm rates are actually higher for women who include anal play in their erotic repertoire. That’s right! Among women who had anal sex during their last encounter, 94 percent had an orgasm versus only 84 percent of those who received oral and 65 percent of those who had vaginal intercourse (National Survey of Sexual Health and Behavior conducted by the Center for Sexual Health Promotion, Indiana University)

Couple the powerful potential for orgasm with the thrill of defying one of the most intense and enduring sexual taboos and you have the perfect recipe for spicing up your sex life through the back door! But since the tissue and nerve endings of the anal area are so sensitive, it is essential to follow some basic guidelines to make sure your experience is as hot as possible:

Become acquainted with your bum.

Your butt is a thing of wonder, but since you probably don’t know this nether region like the back of our hand, you’ll want to do some exploring before you venture into the exciting land of anal play.

On the outside, you have a highly responsive pucker (AKA bum hole/anus) that is rich in nerve endings and responsive to light touch. For some people, this is where anal sex begins and ends. There is nothing in the rule book that says that you must include penetration in your anal sex practice. A good exercise for newbies is to enjoy anal play (licking, sucking, massaging, kissing, etc.) with the promise of no penetration to build trust and become familiar with new sensations.

If you do decide to venture inside, you’ll enter the anal canal which is less than a few inches long and rich in highly responsive nerve endings. Comprised of soft tissue folds, this area has a good capacity for expansion and is sensitive to touch, pressure and temperature.

Inside, you’ll find two sphincter muscles, which are ring-like oval structures that help to hold the canal in shape. The next time you’re in the shower and feeling relaxed, gently slide a lubed finger inside to get to know your sphincter muscles. You don’t have to reach great depths to find your sphincter muscles. You’ll feel the external sphincter, which you can contract and release at will (the way you might flex and relax your biceps) less than an inch beyond the opening. The internal sphincter is just a little deeper, but because this smooth muscle ring is controlled by the autonomic nervous system (which manages automatic bodily functions like heartbeat and perspiration), it remains in a state of contraction. You can’t exercise complete control over your internal sphincter, but just as you can slow your heart rate through breathing and mindfulness, so too can you help relax this sensitive muscle through relaxation and deep breaths.

Beyond the anal canal lies the rectum which comprises the lower section of the large intestine. This section curves laterally (from side-to-side) as well as from front-to-back several times and it is wider than the anal canal. Comprised of mucous membrane, this deeper zone may be less responsive to light touch, but more reactive to pressure.

1. DIY

As a general rule, the best way to venture into the uncharted sexual territory is to experiment on your own before bringing a partner into the equation. This is because solo sex helps to detract from performance pressure and when we’re along we often allow our natural bodily responses to flow more freely. So if you’re curious about butt play, but don’t know where to start, begin by playing with your own bum first to get an idea of how it might feel with a partner.

2. Don’t have a one-track mind

Don’t get hung up exclusively on the butt!

We all have a tendency to get fixated on a body part or sex act when we’re excited, nervous or trying something out for the first time. But there is no reason that you have to focus exclusively on the bum during anal play. Double your pleasure and use a spare hand to rub her clitoris or stroke his cock to produce arousal patterns with which your brain and body are already familiar.

3. Proceed gradually

Anal sex should not be painful, so proceeding gradually in terms of speed, depth and the size of an inserted object is of paramount importance. Take time to deepen your breathing and begin with a very small object like your pinky finger before increasing the size gradually. Sex is not a race to the finish line and incremental experimentation can lead to mind-blowing results.

4. Shelve penetration until you’re highly aroused

It is often a good idea to hold off on penetration until you’re decidedly excited, as arousal can help you to relax and have a palliative effect on your body. Get yourself all riled up using the techniques and body parts you normally play with before introducing new moves or exploring new regions of the body.

5. Use Lube!

Lube is essential to safer, pleasurable anal play. Many people prefer silicone-based lube for back-door exploits, as they last longer and don’t wash away in the shower or tub.

6. Bring yourself to orgasm before experimenting with anal penetration so that your pelvic floor slips into a state of relaxation. Your body is most responsive to pleasure and primed for arousal when your endorphin and oxytocin levels are elevated post-orgasm.

A more pleasurable and safer alternative to numbing creams involves more foreplay, lots of lube and high levels of relaxation prior to penetration.

7. Take control

If you’re an anal sex newbie who decides to have anal intercourse and you’re the receptive partner (AKA the one with an object up your butt), being in control is of paramount importance. Choose positions that allow you to control the depth of penetration and maintain constant communication with a trusted partner whose first concern is always your safety and comfort.

8. Eat lots of fibre!

Though your anus is not a storage compartment for feces, they do pass through there on the way to the porcelain pool, so your diet can impact your degree of comfort and pleasure during anal play. If you don’t have enough fiber in your diet and you have to push hard when going to the bathroom, irritation and muscle strain can occur and cause discomfort. Here’s to a healthy diet and a happy sex life!

FAQ: I’ve tried anal before, but it hurt, so I’m thinking of trying a numbing cream. Do they work and are they safe?

There are many numbing creams and lubes on the market designed to help “ease” penetration through the use of a topical anesthetic. Though these creams may not be dangerous in terms of content alone, their desensitizing effect can increase your risk of injury during anal play. Numbing involves impeding your nerve endings from sending pain messages to the brain. These messages and the ability to perceive pain are essential to all physical (and sexual) activity so that you know just how much you can handle. The anus is not only sensitive but also thin-skinned and prone to small tears which increase the risk of infection. By temporarily numbing your butt (and by extension, your partner’s penis during anal intercourse), you are not only less likely to stop if you experience a small tear and more likely to experience pain once the cream’s effects wear off.

Finger and Tongue Play

When most of us think of anal sex, we assume that it includes a penis sliding in and out of the butt. But the reality is that the hottest and most practiced anal techniques often preclude insertion or involve gentle, shallow penetration with smaller objects.

Since the bulk of your most responsive nerve endings are located near the entrance of the butt, your dexterous fingers and nimble tongue make the perfect pleasure tools. As you take these simple techniques for a back road test-drive, ask your lover for feedback to guide you in exploring new approaches to pleasure:

Breath It In

Use nothing but your heavy breath to prime your lover’s ass for a night of lovin’! Get as close as you can to their skin without touching them and breathe warm kisses on their lower back, between their butt cheeks, over their pucker, and around their perineum. Alternate between breath kisses and deep, pleasurable inhales as you tell them how much you love it.

A Lotta Hot Air

Lick your lips and open them wide as you breathe warm air over your lover’s pucker. Gently flatten your tongue against the opening and then purse your lips to breathe cooler air over the soft, wet spot you’ve created.

Dear Daisy

Use the soft pad of your thumb (slathered in lube) to trace petals around their pucker as you breathe gently over the wet spot.

Eat Your Heart Out

Use your hands to pry open your lover’s supple butt cheeks and dive in with your lips, nose, and tongue. Slurp, kiss, lick, twirl and suck away as though you’re diving face-first into a bowl of freshly whipped cream.

Slip N’ Slide

Slather your hand in lube and slide it a very gentle karate chop-style motion between your honey’s butt cheeks starting at the very top. Once she is fully relaxed, slither your tongue up and down from the tip of her upper cheeks down to her bum hole.

The Reach Around

While you’re performing oral sex on your lover, reach around with a wet hand and circle your fingers around his butt hole. Press gently against the opening and gradually slide the tip of your finger inside as you continue to suck away.

The Reverse Reach

Twirl your tongue around her pucker and gently slide the tip in and out while you reach your flat hand around to stroke her entire vulva. Double the pleasure!

Sit On My Face

Lie on your back and have your lover kneel over your face as she sits atop your face and guides your tongue’s direction, pressure and depth.

Butt Plug Bonus

Slide a butt plug in their ass and twirl it around as you slide a soft tongue all around their genitals.

Tawdry Trace

Trace a slow, sensuous line from the centre of your lover’s spine right down to their pucker and then point your tongue tightly to slide it inside.

Butt Screw

Cross your ring and middle finger, slather them in lube and slide them into your lover’s already primed pucker with your palm facing down. As you pull out, rotate your palm upwards and repeat.

Lip Smacker

Use two fingers to gently tap their pucker gradually increasing the intensity and alternating between “smacks” and slurpy wet lip kisses.

Tongue Twister

Hold their ass cheeks open with your hands and slide your tongue inside. Once you’re as deep as you can reach, twirl your tongue in a circular fashion to titillate the sensitive nerve endings inside the canal.


Press your lips around their bumhole in a wide-open open oval and thrust your tongue flat against it. Slurp away as though you’re sucking on a bottle allowing your natural sounds to emanate freely.

FAQ: I’m totally straight, but my wife wants to try putting something in my ass. I know it doesn’t make me gay, but I can’t seem to get over the idea that straight guys don’t do it. Help!

The exclusive association between butt play and gay men is long-established, but erroneous and highly limiting. Many people enjoy anal penetration including straight men and women and the range of sexual activities that include the butt is vast. If you want to let her experiment with butt play, rest assured that in no way will it impact your self-determined sexual orientation. And if you enjoy it, this is not an indication that you’re gay. Period. No sex act or combination of acts determines whether you’re straight or gay. Your sexual orientation is personal and likely a core part of your identity that will not shift due to engagement in or enjoyment of anal play.

Prostate Play

The prostate, which can be stimulated through the perineum or the inside of his butt is a remarkable source of pleasure. On its own or in conjunction with vaginal intercourse, anal intercourse, oral sex and manual play, many men who have experienced prostate pleasure will tell you that they blow penile orgasms out of the water. But don’t expect a rock-hard erection every time. Sometimes prostate play results in a hard-on and other times the penis is flaccid or only partially erect despite the mind-numbing pleasure he experiences during prostate play. This is yet another reminder that there exists no universal indicator with which to gauge arousal.

Charlie Glickman (PhD), Sex Coach and author of The Ultimate Guide to Prostate Pleasure explains:

Erections can be unpredictable during a prostate massage. Some men say that prostate play gives them a really firm erection, but others report exactly the opposite. It’s not clear why it happens. One possible explanation is that relaxing the pelvic muscles enough to allow penetration means that less blood is trapped in the penis. Another is that some guys need direct stimulation to stay erect. And if he’s feeling any concerns or worries about anal penetration, such as whether it will be uncomfortable, the stress can short-circuit the erection process. Fortunately, adding a little cock stimulation will usually change that.

Prostate massage can be amazing, whether someone has an erection or not. So don’t let assume anything. If his toes are curling and he’s having a great time, there’s no reason to get worked up over whether he has an erection.

It’s also pretty common for guys to ejaculate more semen from a prostate massage since you’re squeezing more fluid out of the gland. That’s especially true if you like long massage sessions, and in fact, you might end up with more precum along the way. But when he ejaculates, he might not shoot as far since the rhythm of your massage might not be in sync with the muscular contractions of ejaculation. One way you can get around that is to have him on his hands and knees for a gravity assist. Just make sure you put a towel under him or the wet spot will be huge!