Jan 5, 2019

The Ultimate Guide To Anal Play

Butt Stuff. Tushy titillation. Rousing the rump. Fanny shenanigans. Whatever you want to call it… anal play is a hugely misunderstood treasure trove of sexual pleasure.

Like many people, you might feel a bit of hesitation around trying it, whether you’re worried it’s “dirty”, have had a bad experience, or simply don’t know what to do back there. 

This guide will demystify anal play and give you a steadier footing on which to confidently delight the derriere (okay, last one).

Anal pleasure is very real, and very significant.

In terms of pleasure and sensation, the anus is the only spot that comes close to having the same amount of nerves as the clitoris. So if you can work through any hang-ups around anal play, it might mean breakthroughs to new heights of sexual pleasure, as well as deepening your bond with your partner. 

That said, anal play won’t be for everyone. If you find it physically uncomfortable, or even painful, that doesn’t necessarily mean you have a “sexual block” of some kind.

Different strokes for different folks!

At the very least, try it first (or try it again, in a different way than your last experience). Because what stops people from experimenting with anal play is rarely a real physical issue. It’s either a mental block, or having rushed into it before without being educated on best practices.

And remember, anal play doesn’t equal penetration. There’s a lot of sexual pleasure to be had in the realm of anal play with zero penetration.

So whether you’ve never explored it, or you’ve had a bad first experience, this will help you have the best chance of enjoying anal play. 

First off…

Forget pretty much everything you’ve ever learned about anal play from porn.

In real life, safe, clean anal play rarely looks anything like it does in porn. Yes, there are some scenes that showcase subtle, artful anal play. But, like most things in porn, it’s usually sensationalized and taken to the extreme that is simply not realistic or helpful for 99% of people.

Guys are ramming themselves into the recipients anus at full throttle without warning. They pop back-and-forth between the vagina, ass, and mouth every 3 seconds. The actor receiving it (who has, off-screen, spent countless hours training themselves to be able to take penetration with relative ease) is being paid to stomach any discomfort and make everything seem orgasmic.

Any porn actor will tell you that anal scenes require a lot of preparation – including enemas, pre-stretching, eating restrictive diets, fasting, and more.

What you see is highly unrealistic. For the average person (porn actors are average people, but you know what I mean… average people who are non-porn actors), this version of sexual play would equate to anal abuse, not anal play. And it’s unsanitary and even straight up dangerous to replicate.

Because anal play is so loaded, misunderstood, and easy to do wrong, we need to talk about some higher level stuff before we get into the “how-to” part. Just like anal play itself, this isn’t a process that should ever be rushed into.

The Surprising Benefits of Anal Play

Having entirely new kinds of orgasms and upgrading the intimacy with your partner are already huge upsides. But there are a couple other big ones you wouldn’t necessarily expect.

anal play

Less stress, more happiness, and increased cash flow.

Let me explain. There is a reason why we use the phrase “tight-ass” to describe someone who is stuck up and controlling. It comes from the term anal retentive, which is an idea Sigmund Freud developed through his work in psychoanalysis.

Key anal-retentive traits are stubbornness, obsessive orderliness, and urges to control. According to Freud’s theory, one way people can develop these traits is during their toilet training years. If they were heavily scolded or oppressed, they would develop anxiety and shame around controlling their bowels. Hence, “anal” retentive. This creates an overall fixation on self-control and restricting libido energy. 

We create so much stress in our lives by holding on and trying to control everything – both physically and mentally. This internal grip restricts energy – including money – and your whole life from flowing naturally.

Now, I’m fully aware of the concept of recency bias, but I once had a mentor of mine tell me to engage in anal play during masturbation several times per week for three months, and those three months also happened to be one of the single greatest upticks in my income in my entire life. Coincidence? Maybe. But maybe not.

Exploring anal play has effects that ripple out into your general attitude and how you carry yourself. Don’t underestimate the mind-body connection and the healing that can take place through sex.

Equanimity, abundance, and wellbeing come from being open and expanded, not closed and contracted.

If someone’s going to put something up your ass, you’ll definitely have to work on trusting and letting go. You have to relax your muscles, anxiety, and the urge to control another person’s perceptions of you, and surrender completely to the experience. This can be insanely liberating, and might just change how you think and operate in your life.

Breaking The Societal Taboo

Our culture is the product of many centuries of heavy religious programming. Sexuality, not just butt stuff, still has tons of repression and shame around it.

Anal play, specifically, was a ticket to eternal damnation in the fires of hell (and still is, according to some sad, sad people) since it was primarily associated with homosexuality. Because the act didn’t lead to making babies, it was considered sinful and the church generated tons of fear around it.

In most Western countries, religious influence has faded more into the background, rather than being front-and-centre. But still, there is at least common obsession with cleanliness, orderliness, and keeping yourself “together”. People are afraid to get a little dirty (in life, and in the bedroom) and risk doing something unsexy.

The wilder world of adventurous sex, such as BDSM, has always been at odds with the mainstream. It’s seen as something for deranged, dysfunctional freaks. In reality, it just scares the shit out of people because they have yet to integrate those parts of themselves, they have no clue how to handle themselves in that realm, or are afraid of losing control in general.

And if people actually do end up exploring kinky sex, or anal play, it tends to be something they hide from the rest of the world and wouldn’t readily admit to it. They feel the natural desire to experiment, but feel like they have to hide it because of perceived societal pressures.

So if you have any limiting thoughts around anal play, this is a call to examine what they are and where they came from.

“Okay, but isn’t anal play unsanitary?”

No, not if you follow some basic practices of hygiene.

Since our longest standing relationship with our butts is around pooping, it’s understandable why many people are skeptical about the sanitation and pleasure potentials of anal play. But here’s the honest truth:

Licking a clean asshole is no dirtier than licking a scrotum, penis, or vagina. 

The key word here is “clean”, and we’ll get to the step-by-step soon. But first…

The Anatomy of Anal Pleasure

The anus itself is the actual anal opening, which is surrounded by the sphincter muscles. There is an exterior and interior sphincter. The external one you can control and flex, whereas the internal one is automatic and very slow to relax. 

This ring of sphincter muscles is very sensitive because it has so many nerves, which are touched so rarely. This sensitivity is a delicate edge, as it could easily mean either pleasure or pain. This is really important to be mindful of.

Another source of pleasure is the pudendal nerve, which carries sensation from the genitals through the perineum and around the anus to the lower spinal cord. Anal play indirectly stimulates this nerve, compounding on whatever other stimulation it’s picking up from the genitals. 

In men, there’s the P-spot. This is the male equivalent to the female G-spot. The “P” comes from prostate, which is the gland you’ll be stimulating in the exact same way you do the G-spot. It’s about two-knuckles deep on the upper inside wall of the rectum. You insert a finger (or two, if it’s open enough, or a toy) and make the “come hither” motion. 

You really only want to focus on the anus and the first few inches of the rectum. Rectal wall tissues are very fragile and can tear easily. The canal also takes a hard 90 degree turn about 4-6 inches in, unlike the vagina, so deep penetration puts a lot of stress on that spot. There’s no need to go too far.

The Best Sex Toys For Anal Play

There are a lot of well-designed toys to accessorize your anal play. These are also much safer to use than anything you already have because they’re specifically designed not only for pleasure, but to prevent getting lost up there (which, according to a friend of mine who works as an emergency room nurse, happens all the time).

Because the rectum can act like a vacuum, anal toys have cords, rings, or flared ends for easy retrieval. For starters, try a standard butt plug or a small set of anal beads.

Anal beads are sturdy strings of multi-sized balls which provide pleasure when inserting/removing from the anus and rectum. They’re also nice to leave in while engaging in other play. Tip: as she gets closer to climax, or during it, insert/remove anal beads to shoot stimulation through the roof for a super intense orgasm.

Butt plugs come in various shapes, but be sure to start small. Get one that is made of silicon, steel, or pyrex glass, rather than cheap plastics. These are the easiest to clean properly and will prevent the accumulation of unwanted bacteria. Glass and steel are even better as they will be resistant to breaking down by oils and lubricants.

Besides enhancing other play, like anal beads, butt plugs are a great way to pre-stretch the anus for full penetration. If you’re a Dom, have your sub wear it out in public on a date before you play together. Ask them how it feels, remind them why they have it in and tell them what you’re going to do to them later.

Another one well worth mentioning is the prostate (P-spot) massager. Believe it or not, these are one of the best selling sex toys of all time. Some are shaped like honey dippers. But the new ones look more like sleek L-shaped vibrators. These can be extra handy if the giver doesn’t want to use their fingers.

How To Practice Anal Play Safely

anal play

1. Hygiene

With the proper preparation, anal play is quite sanitary. Review these basic precautions and decide what measures will make you feel at ease. 

  • Wash. If you’re receiving anal stimulation, wash thoroughly in the shower beforehand. After emptying your bowels, use a natural, scent-free soap to wash the anal opening thoroughly to cleanse any stray fecal particles that may be lingering.
  • Grooming. If you’re a hairy guy and you’re looking to engage in anal play with a partner, trimming the area with an electric groomer will help with sanitation, while making it look a little more appetizing. Waxing is also an option. And a lot less painful than you might imagine (speaking from experience).
  • Enemas. A full-on enema is totally optional, especially if you’re really into full penetration. This is where you flush out your bowels with lukewarm water. There are plenty of good guides online, so I’ll let you look up that process yourself. Again, not really necessary if you’re doing basic occasional play. But if you’re extra concerned, it could work for you.
  • Gloves. Black nitrile gloves are a sexy option to keep things extra clean. They’re synthetic rubber and hypoallergenic, which minimizes any potential reactions someone might have to latex. This way, you can also pop the glove off and use your fingers on her pussy/his cock without worrying about transferring anything.  
  • Condoms. These are good for general sanitation. But the fact also is, anal penetration is one of the easiest ways to contract STI’s. Always get tested first before sexually engaging with a new partner, and ask them to do the same. Unless you’re 100% confident in each other’s status, using rubbers is always a smart choice.
  • No switcheroo’s. If you put your cock/finger/toy in her butt, don’t switch back and forth to the vagina. This will upset the delicate vaginal environment and cause bacterial vaginosis. Unless you’re using gloves/condoms, anal play will likely be at the end of your session.

2. Setup

  • Wash up and perform any other prep procedures you want to include from the list above.
  • Have LOTS of lube on hand (water/silicon-based, or coconut oil) since this area of the body doesn’t self-lubricate. 
  • Lay a towel down to protect your sheets from all the oil/lube, but also in the unlikely event of a spontaneous bowel evacuation if you’re doing deeper penetration.
  • Stage your toys close at hand, after being washed thoroughly.

3. Communication

Talking is always crucial to better sex. Because we’re dealing with such a vulnerable spot (both psychologically/emotionally and physically) it’s extra important to constantly check in and get feedback around what’s feeling good and what’s not.

Maybe the person needs more time before moving on to the next step. Maybe something doesn’t feel good for them, and they’d prefer something else.

Begin your communication long before you get around to actually playing. Build trust around taking this step together.

You might have to broach the subject of anal play with your partner in the first place, and bring up the fact that it’s something you want to try. They may have to do some research and education to create more comfort and openness, and relax their own hang-ups. Feel free to review this article with them and stop to chat about certain sections along the way.

Uncover any fears and hesitations either of you might have behind trying anal play. For many people, a big one is that they’re ultimately afraid of their partner finding them unattractive and not loving them anymore. They’re afraid if their lover smells, sees or tastes the wrong thing, they’re going to find them gross and repulsive.

This is exactly the kind of thing I’m talking about when I say vulnerability and trust are super important. Communicate until both people can relax any fears of judgment and feel totally accepted and supported by each other.

Make sure your partner feels a sense of full permission to call things off in the moment if they don’t feel comfortable. Sensitive lovers can have a hard time saying “no” or “stop” if they’re worried about hurting their partner’s feelings, or leaving their fantasy unfulfilled. With the risks involved, anal play is not the time to put discomfort aside. You should both have your yes’s and no’s readily at hand, at all times, during anal play. You have full permission. Communication is key!

When you wrap up, reflect and talk more specifically about the sensations, timing, and overall experience. Is it something you want to try again? What would you do differently? What felt awesome and what felt weird?

4. Stimulation

It’s always a good idea to warm up with ample foreplay before moving into anal play. This will get circulation going and relax all orifices.

If the woman is receiving, you may even want to wait until after she’s had an orgasm or two. This not only relaxes the pelvic floor and helps increase physical openness, but some also feel way more mentally open to anal play once they’re aroused in the moment.

Whenever you’re ready, have the receiver lay on their back. It’s the easiest position to fully relax in. Start slow with external stimulation on the outside of the anus using gentle pressure.

Use your tongue if it turns you on. If not, a well-lubed finger, or several fingers side by side, is still very tantalizing. Wait until the receiver is totally comfortable at each stage before continuing, and then tease them by waiting just a little bit longer.

Remember: use LOTS of lube. When you’re ready to insert, go slowly and gently. The sphincter muscles take time to relax, so be patient. Start with a small finger, one knuckle deep. Make small circles and massage the opening. Then work your way up to two knuckles.

On guys, when you’re ready to hit the P-spot, switch to the index or middle finger (because of their length) and slowly stroke with the “come hither” motion (or use your P-spot toy). Pair this with a blowjob and you’ll blow his mind.

On women, pairing anal play with oral sex or clitoral stimulation also really intensifies orgasms. Introduce toys into the process as you see fit.

If you’re going to use your cock, go just as slow as you did with your pinky finger, if not slower. This is a huge upgrade in size from your finger. You’re also not likely going to go as deep as you would in a vagina. Just a few inches is all you need. But go as far as feels good for them.

Note that without tons of warm-up and experience, many women find this simply straight up painful. Make sure she’s into it first, lube up, and take it slow!

Keep communicating and enjoy the ride. When you’re done relishing in the post-orgasm glow, wash everything well and debrief the experience.

Anal Play, Made Simple

There’s your deep dive guide to anal play. Some love it, some don’t. But since anal play is such a delicate and vulnerable act, it will likely bring an added layer of intimacy to your relationship.

No matter what your preferences are, everyone can benefit from going through the process of trying it out. Plus, the potential upsides are so big that it’s totally worth the effort.

Remember to talk thoroughly before, during and after. Stay clean and play safe. Use more lube than you think you need to. And take it very, very slow!

May your sex and orgasms be ever evolving.

Dedicated to your success,


Ps. If you enjoyed reading this article on anal play, you will most likely also love checking out any or all of the following:

Supercharge Your Sex Life (video series for men)

How To Master Dark Sexual Energy As A Man

The Ultimate BDSM Guide For Beginners

5 Questions To Ask Your Partner For Better Sex

How To Last Longer In Bed (9 Simple Exercises)



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