Anal Massage: A Touchy Subject

This article was originally published in Exotic Magazine in May, 2015

Anal play is a touchy subject. In a society with a strong love/hate relationship with sexuality in general, anal sex pushes real buttons. With all this ass tension, how do we move from scared, to curious, to relaxed and gaping?

The scariest part of anal play may very well be talking to your lover about it. In my practice, the most relevant and revealing question about a person's problem is usually, "Have you tried talking to your partner?"

But if you're eager to try it and you haven't had the conversation, don't ask for it out of the blue. Just like asking, "Hey baby, wanna suck my cock?" will go over much better if you've been making out for ten minutes than if you approach a stranger at a bar, you are more likely to be rejected if you ask a person to open up the most fragile part of themselves when they're cleaning up your literal shit in the bathroom. Start by taking a sexy shower together and exploring their body. If they jump when you brush through their ass crack, talk about it. Starting with, "I want to pleasure you," is usually a good idea.

Now, in my experience, and according to research, (Read the book A Billion Wicked Thoughts), more people want to be anally penetrated than are looking to anally penetrate. Here's why: it feels awesome (which you know because pooping is practically the most pleasurable part of your day) and it's super relaxing. Anal penetration stimulates the Vagus nerve, which turns off adrenaline production and turns on sleepiness. (Expect to fall asleep after an anal massage.) Furthermore, the prostate is most easily reached through the anus (for penis-people; for vagina-people, the prostate (aka G-spot) can be reached through anal or vaginal stimulation). The prostate creates cum-juice. Push it and you'll leak, but in a fun way.

So I'm going to assume that when you read any "How To Anal" article, you're reading it with the hope that somebody's going to touch your ass gently, maybe even lick it, and can you imagine, if the stars align, maybe even put something long and hard inside you. So here's my tip for receiving anal play: Give Some First. And here's how to do it right:

1) Set the mood. Clean your house so there will be no distractions. Make sure it's warm enough to relax naked. Light some scented candles; nothing interrupts anal play like the wafting smell of cat shit in the litter box.

2) Don't go straight for the butt, start with a full-body massage and move progressively closer. The asshole does not exist in a vacuum! Use coconut oil, that shit's good for everything. Just make sure if you're going to put some in somebody's ass, you don't put that jar back in the kitchen.

3) Get consent, give consent. Consent is often misunderstood to mean you have to ask "Can I {blank} you?" every step of the way. Not only is this redundant, it can wreck the mood and make people nervous. There are other ways to show your partner you care about what they want. "Do you like this as much as I do right now?" or "Is there anything I can do to make you more comfortable?" Are sexy ways to make sure your partner is engaged.

4) Listen to their body. With connected movements, make your way closer to their ass. If their body relaxes, or if they moan with pleasure, keep going. If they tense up or stay completely silent, they aren't having a good time. The only real goal is to have fun touching each other, and as long as it's fun, explore anal. If a person isn't ready in mind or body, anal sex won't be fun, and you're unlikely to be invited back.

5) Wear nitrile gloves. They'll make your fingers smoother and it's less likely to spread infection. And this way you can pretend you're a doctor, doing something naughty.

6) If you think you're moving too slow, move even slower. Graze their hole, push on it with a wide touch so there's no risk of entry and then move away. Keep massaging their ass. Make their hole hungry for your touch; pleasure your partner until their body begs you for more.

7) Switch things up. Try different strokes: a hypnotists' swirl, a mischievous villain's finger roll, a dismissive hand flip. Vary your intensity: ticklishly light or physical therapy firm. Use different speeds: slow and slower. All the while, ask your partner for sexy consent, "Which is better? Does this make you want more?"

8) Wait until their asshole tells you it's time to penetrate. When done right, anal massage transitions from external to internal when an asshole opens up and swallows your finger. Unless it's grasping at your fingers like an alien barnacle monster, or your partner is begging for it, hold off on penetration. You'll see what I mean. If you have to push or pull to get inside, you're doing it wrong; slow down.

9) Stretch the sphincters slowly and gently. By now you've spent the approximate length of one Marvin Gaye album in anal massage, and your partner's baby-barnacle-alien-monster is sucking on your finger. Once inside, cautiously feel around the ass and notice there are two rings of muscles sucking on you. Some people won't feel inner play as well as outer play, so be sure to check in, as always. You can stimulate both inside and outside at once, it's called multitasking and frankly I think more people need to realize this during all types of sex. With plenty more coconut oil along the way, gently press and stretch outward in a circular motion.

10) Continue as long as it feels good. If your partner falls asleep, consent is revoked.

DO NOT ask for an anal massage immediately after giving one. Instead, soak up the praise and admiration of your partner who is impressed with your new skill. Let them relax. Later, when they're not expecting it, clean the house first and then hand them this article.

Dr. Helen Shepard is a clinical sexologist with a practice in Eugene. She'd be happy to talk more about the medical benefits of anal penetration and can be reached at EugeneSexology@gmail.com