How to Explore Anal Masturbation

Dr Megan Fleming

It’s Masturbation May, a great time to up your game and exploration of pleasure. For most people, the word anal isn’t neutral and they have a pretty strong reaction to hearing it. Many may have an immediate response of “No” or “Not for me” around the idea of anal play, without ever having touched their anus to explore gentle massage and pressure. I’m a firm believer that true knowing is experiential knowing. We have so many conditioned ideas about what’s pleasurable and what’s not, what’s allowed or forbidden.

All I can say is, if you haven’t ever tried anal play, there’s no time like the present. It may or may not be for you, but you won’t know if you don’t try! Another reason to try is knowing that the pudendal nerve is the same nerve involved in the pleasure you experience from stimulation of the clitoris, vulva, penis and perineum.

The great thing about solo anal play is that you get to explore the sensations and experience of being both the giver and the receiver.

Start with hygiene. It’s important to empty your bowels and take a shower cleaning externally with an antibiotic soap. Short nails are best or you might want to consider a finger cot (it’s like a condom for the finger).

Know that you can never have too much lube. While there’s debate over whether water based or silicone is better, remember the anus isn’t self-lubricating and many experienced with anal play prefer silicone because it lasts longer. That said, silicone lube isn’t compatible with silicone sex toys.

Get into position. A good one to start is with knees pulled up to your chest and often a pillow or wedge under your pelvis to give you better access.

I can’t highlight enough the importance of only introducing massage or any anal play when you are already highly aroused. So enjoy getting yourself all hot and bothered with your usual masturbation play.

Start with your index or middle finger, rubbing/massaging your anal opening and inner rim. It can be helpful if you tighten/contract your PC muscles (Kegels) and tighten your buttocks, on the release; insert your well-lubricated finger about ¼ inch. Relax, hold 3-4 seconds and repeat, contracting muscles, relaxing the anus and sliding your finger further in as you go, taking all of the time you need.

Some people find it really enjoyable to be stroking their clitoris or penis at the same time with their other hand. For vulva owners, it’s important to know that you never use a finger or toy from anal play for stimulation of the clitoris or the vulva as this can cause infections.

Anal sex toys are also a great way to explore pleasure, as we don’t always have the flexibility or dexterity of our fingers to hit the internal places that feel best. Make sure that anything you stick in your butt is flared or flanged because if not, when you orgasm, and the muscles contract it can have a vacuum effect where it can slip and can get lost in the rectum. I assure you a trip to the ER isn’t what you have in mind.

Make sure to clean your toys after every use and that they are completely dry before putting away. If they are non-porous, such as silicone or stainless steel metal and don’t vibrate or are waterproof, you can use water and mild unscented hand or dish soap. For ease I also highly recommend Lovehoney’s Fresh Toy Cleaner, which is safe to use on all sex toy materials.

As you explore g-spot and p-spot stimulation through anal play, remember the mantra of Try, Try, Again. Assuming your experience wasn’t painful (a red light and you stopped) and you only felt so/so about the sensation and experience (yellow light), I recommend trying several times to see if as you relax into the experience the yellow light goes green and you now have a new go to pleasure practice to add to your sexual menu/repertoire.

Follow the pleasure and see where it leads you.

My recommendations:

Beginner Butt Plug: Lovehoney Jeweled Metal Beginner’s Butt Plug

Beginner Prostate Massager: We-Vibe Vector App & Remote Controlled Prostate Massager

Advanced Prostate Massager: Fun Factor Duke Rechargeable Vibrating Prostate Massager

Best Rimming Stimulator: B-vibe Remote Control Rechargeable Vibrating Butt Plug

Dr Justin Lehmiller

Think for a moment about what brings you sexual pleasure. Now think about how you came to discover this about yourself. Odds are, you probably learned quite a bit through direct experience. I mean, it can be hard to know what you like until you actually give it a try. And, sometimes, things you never expected to enjoy turn out to be amazing.

Masturbation May is a perfect excuse to engage in a bit of self-exploration and discover new sources of pleasure. If you’re looking for ideas, something most people haven’t yet explored is anal stimulation during masturbation—and even if this is something you have explored, chances are that there are some new ways to give it a go.

Incorporating anal play into masturbation is something that persons of any gender or sexual orientation can potentially enjoy. It can offer pleasure in and of itself because there are many nerves that run through this area that connect to the genitals. However, many people also report that it intensifies orgasm. Anal stimulation can put you in a state of heightened awareness that makes everything feel more intense.

In this post, we’ll explore a few different ideas for anal masturbation, from beginner to advanced. However, a few safety tips and best practices first:

1. Relax, breathe, and go slow. Take your time and don’t force anything. And if you experience pain, stop.
2. Use lube. Lots of lube. The anus does not naturally lubricate in response to sexual stimulation, so use of an artificial lube is essential. However, make sure to use a lube that is compatible with whatever toy(s) you are using.
3. Start small. Don’t go for a big toy the first time around—and even if you are experienced, use a smaller toy to dilate first.
4. Make sure that whatever you put in can come out. In other words, don’t go past the base of the toy to avoid anything getting stuck.
5. Make sure your toys are clean before and after use.

Beginner ideas

The Beginner’s Butt Plug is often a great place to start. It’s a small but versatile toy that can help you explore anal sensation for the first time.

Silicone Anal Beads offer another possible entry point. This toy is a little more flexible in the sense that you can explore shallower or deeper penetration. It also adapts to the shape of your body, which can increase comfort.

Intermediate ideas

Once you’ve had a bit of practice, consider an anal toy bundle. This will allow you to experiment with a few different kinds of toys (butt plugs, beads) some of which have motorized functions. This can really help you to hone in on what you enjoy and what works best for your body.

Or, if you have a prostate, consider a prostate massager that is optimized to help you experience a P-Spot orgasm.

Advanced ideas

If desired, you can potentially go for something larger. Anal beads, butt plugs, and dildos come in a wide variety of shapes and sizes (the options are endless!), so that’s one easy way to mix up the sensations and continue exploring.

However, another approach is to look at toys that offer genital and anal stimulation simultaneously. For example, the Double Penetration Vibrator can provide both vaginal and anal stimulation at the same time. Likewise, some butt plugs have an attached cock ring that can provide simultaneous penile and anal stimulation.

Or, go a step further and bring a partner into the mix with a remote-controlled butt plug and let your partner control the sensations.

We’re Team Masturbation all year round, but when better to shout about it than Masturbation May? Solo play is not only great for mental wellbeing, but understanding what turns you on will help you enjoy better sex with a partner, too. So get your hands, lube, and toys at the ready, and Go Love Yourself.

Click here to go to the Lovehoney Masturbation Hub.