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All About Anal: How To Have Amazing Anal Sex

It’s 2021. We do butt stuff now. And that’s a great thing.

Anal pleasure is a big, beautiful and interesting topic that’s new to many, so we have a lot of territory to cover – for anyone, in any body, who’s interested in anal adventures – including positions, porn, prep, poop (and how to avoid it), and the best ways to help make anal sex truly fun and liberating for everyone.

Only if we want to, of course! For a long time, anal was deeply taboo – the last frontier for straight people (and especially straight penis-havers on the receiving end). Viewed as the exclusive province of gay men (even though plenty of gay men prefer to express their sexuality other ways), or a “poophole loophole” to avoid “losing one’s virginity” in a technical sense, anal sex lived on the fringes until fairly recently.

Now, it’s everywhere. This is largely due to its popularity in porn, and also because of a newfound cultural liberation surrounding sex and sexuality in general. More and more people, of all genders and orientations, are discarding the old taboos and saying “yes please” to anal sex.

If you want to try it – or even if you’re an anal veteran – there’s a learning curve. Managing expectations is important. Maintaining open communication and healthy boundaries is even more important. But if you’ve decided anal is for you, the taboo aspect may be a real turn-on. It can be deeply intimate – and when done correctly, anal can just feel fantastic. (Anal orgasms? Real. Nuff said.)

Whether you’re planning on pitching or catching, let’s get started!

A Note On Porn

We’re starting here because porn is many people’s entry point, so to speak, to the idea of anal. In porn, it can be really hot. There’s often an element of degradation, of dominance and submission, that’s a very common kink among otherwise vanilla people. It can look like tons of fun.

However, if you and your partner aren’t porn actors, good anal is likely to be very different from porn. Porn performers are professionals who do a great deal of prep for anal scenes. They often fast and douche ahead of time to keep everything clean. They apply lube between takes. They work up to the scene using toys and dilators (and sometimes each other), so they’re loose enough to handle the fast insertions and no-holds-barred pounding that look good on camera. Porno anal is hard work.

So attempting a porn-style anal session without experience, patience and preparation is kinda like watching a Steve McQueen car chase in a movie and trying to drive like Steve McQueen – a great way to hurt yourself and possibly others, and maybe make a huge mess. Leave the rough stuff to the pros to start, and if your partner is trying to talk you into reproducing their favorite scene, have a frank conversation about whether it’s realistic for you.

A Booty’s Best Friend: The Best Lube for Anal Sex

Lube is great for all kinds of sex, but absolutely mandatory for anal. Mandatory. Generously and frequently applied. (“But you never see lube in porn!” See above – it’s there, just off camera.)  

Unlike vaginas, anuses don’t self-lubricate – at all. The rectum produces a small amount of mucus, but not nearly enough to accommodate penetration. Also, anuses don’t stretch easily. For anal, you absolutely need lube to avoid pain and tearing. “Brokeback Mountain” notwithstanding, spit won’t cut it.

So what kind of lube to use? We are, of course, big fans of our Sex Oil – with broad-spectrum CBD to help soothe any discomfort, providing a botanical assist to the slickness of MCT coconut oil. When using an oil-based lubricant, always make sure your toys and condoms are oil-safe.

And if you’re not sure whether your toys and condoms are oil-safe, many anal enthusiasts swear by thick, durable silicone-based lube. It’s safe to use with regular condoms, but not with silicone toys. As with all things anal, planning is important!

How to Have Safe Anal Sex

When most of us say “safe sex”, we mean avoiding STDs like HIV/AIDS – as a blood-borne virus, HIV is especially communicable via anal owing to the possibility of microtears. But you can also get other STDs, like herpes and gonorrhea, via anal. You may also run the risk of exposure to hepatitis, which is transferred via fecal matter, and UTIs or bacterial vaginosis, if poop particles end up on or in someone’s vulva or vagina. Not fun.

However, all this is very avoidable. Use condoms, which also make cleanup much easier. Never ever switch from anal to vaginal penetration with the same penis or toy in the same bedroom romp (there’s a reason you rarely see this even in the most extreme porn). Be cautious and mindful and you should be just fine.

In addition to keeping your body healthy, there are other dimensions of safety to consider – including your feelings! If you’re not comfortable with the idea of anal, mentally or physically, you should absolutely feel OK turning it down. Communication, as with all sex, is key.

And if you’re going for it and it hurts, stop immediately. Sharp pain is your body’s way of telling you something is wrong. Go slower, use more lube, start with a small toy, or stop altogether and try another day. Be patient with yourself, and insist on patience from your partner.

Pleasure and Anal Anatomy

Now that we’ve got all that out of the way, on to the fun stuff! Anal pleasure can be out of this world, regardless of what kind of genitalia you have. Every body is different, and some lucky bodies can experience earthshattering orgasms from anal penetration. 

The reasons for this will be different, depending on whether you have a clitoris or a prostate. So it’s helpful to understand a little bit about the relevant anatomy before you dive in.

If you have a clitoris.

Your clit is so much more than the little nub at the top of your inner labia. It’s a surprisingly large, complex organ with sensitive tendrils woven throughout your pelvic bowl – and for some people, it’s in direct communication with the abundant nerves in the anus. Like G-spot orgasms, anal orgasms can be thought of as clitoral orgasms – accessed through the back door.

Also, depending on the angle of your vagina, anal penetration can actually hit your G-spot dead-on, through the wall of tissue separating your vagina and your rectum. Even if you can’t access G-spot orgasms via vaginal penetration, you might be able to via anal. Amazing!

If you have a prostate.

We’ll get right down to it. Your prostate gland, which is roughly walnut-sized and may be accessed by pressing towards your belly button a few inches inside your rectum, is a hidden jewel that can produce rocket-ride orgasms. People who’ve had P-spot orgasms describe them as a mindbending whole-body experience.

For heterosexual-identified people with prostates who may associate receptive anal sex with homosexuality, prostate play can represent a bit of a mental hurdle – but it’s a hurdle worth making, we think. If you’re curious, but self-conscious about trying it with a partner, grab a buttplug or prostate massager and try working some anal self-love into your masturbation routine – and enjoy the fireworks.

You also may have heard of pegging. You might be thinking, “what is pegging and should I try it?” Simply put, pegging is heterosexual anal sex with the woman as the “pitcher” and the man as the “catcher”. It’s also gaining in popularity for good reason. All the Anal Rules about lube, patience, trust, and wide-open communication – and especially respecting the “catcher”’s limits – apply to pegging as well, but if they’re followed scrupulously, femme-on-masc anal sex can be wildly intimate and great fun as well. 

How to Prepare For Anal Sex

When considering anal prep, you’re probably trying to avoid two things: poop, and pain. And we’ll be frank about this: both poop and pain can be a factor. But they needn’t be! This is what prep is for, and a good pre-butt-stuff prep routine can take a lot of the pressure off.

As for avoiding unwanted encounters with feces – well, you’re going where it lives. A little acceptance and flexibility on everyone’s part is necessary. However, if you’re on the receiving end, and if you’re in good digestive health and have had a solid BM recently, you’ll probably be fine without intervention.

However, if you don’t quite trust your colon, many anal enthusiasts insist on douching ahead of time. Unlike vaginal douching, which is always a terrible idea, anal douching can help make both parties to anal sex more comfortable. 

You can buy douche bulbs at sex stores, or saline-only Fleet enemas at drugstors or online. Follow the package instructions an hour or so in advance, and finish external cleanup in the shower. And if you’re a real anal devotee, you can buy douching attachments for your shower or toilet.

Now, on to the comfort part. Our Intimacy Suppositories with CBD, designed to help relax and soothe from the inside out, have helped many members of our community achieve fantastic anal orgasms. Insert up to half an hour ahead of time. 

And always always keep in mind that for most people, anal penetration takes a lot of patience. Start with stimulating the anus just on the outside, with tons of lube. Slowly insert a pinky finger or a small toy and make sure the receptive partner is comfortable and enjoying themselves before introducing more – or stop there! When adding a penis or a larger toy, go very very very slowly and pay attention to all the sensations. This will take a while. Enjoy it.

Best Positions for Anal Sex

They’re not all that different from the best positions for vaginal sex – the entry point is pretty close, anyway. But when considering different anal sex positions, you’ll want to keep two things in mind – depth and angle of penetration, and the amount of control the “catcher” has. Especially if you’re new at this, control is extremely important to ensure everyone has a good time. So here are some of our faves, in order from beginner to expert.

Cowgirl/reverse cowgirl.

Or boy. Receptive partner on top. We’d go so far as to say this is the best bet for anal virgins – the “catcher” has all the power, and perfect control over what they’re willing and able to take. It does take reliable core and quad strength, so if you have different physical needs, read on; however, “just lie still and let me do the work” can be extra-hot at the same time as you’re easing yourself in.

Also, reverse cowgirl isn’t always the most enjoyable position for the person on top – except when it comes to anal, which can make shallow penetration at an oblique angle feel fantastic.

Side-by-side/spooning.

A great one for receptive partners who may have difficulty supporting themselves upright, this position is also cozy and comforting and allows for easy, shallow penetration to start. (It’s also great if you’re worried about making weird faces.) The receptive partner can pull their knees up a bit for ease of entry.

The booty prone bone.

Receptive partner on their belly, perhaps with a pillow under their hips and one knee tucked up and to the side; active partner crouching behind them. The “catcher” sacrifices a little control here, but since the “pitcher”’s movement is more restricted than in regular doggy, they can grind in as slowly as needed.

Doggy.

A classic for obvious reasons, doggy is great if both partners are confident that they know how far to go, how hard and how deep. Note that the most pleasurable angle may be different than for vaginal sex; the receptive partner can arch their back up or down, and the active partner can (and should) experiment with their approach as well.

Legs-up missionary.

It’s hot; your face is right in their face. The active partner has allll the control. And if you want to go deep and hard – and feel safe and comfortable doing so – this is the one. If you love receiving anal, and you know you’re all the way ready, parking your knees by your ears and just going for it can be Goals.

More Anal Sex Tips

But wait, there’s more! Once you’ve got the basics down, there are plenty of ways to expand your anal repertoire and take the booty action to the next level.

Rimming.

Rimming is licking someone’s butthole. For many, it is a Bridge Too Far (and that is fine!) For many others, it’s ecstatically enjoyable and also a great way to warm up for anal penetration. Being scrupulously clean is important, obviously; many bacteria that are perfectly happy in the rectum will wreak havoc in the stomach. If the person being rimmed has a vulva, end your oral sex session with the rimming part – heading back up can bring those same bacteria to not-so-great places. And consider using a dental dam – anuses are so sensitive that a layer of latex or polyurethane shouldn’t get in the way too much.

Toys.

There’s a whole world of anal toys out there – and the most important thing to keep in mind is that anal toys, and ONLY anal toys, are for anal. Do not anally penetrate someone with anything that isn’t specifically designed for the purpose, because unlike vaginas, which end at the cervix, anuses may devour inappropriate objects and hide them so far out of reach that you risk becoming a funny emergency room story.

All toys for anal – plugs, dildos, whatever – MUST have flared bases. If you’re using a strap-on, it must lock securely into its harness. Do not use fruits, vegetables, bullet vibrators, bottles, other common household items, or any object not intended for anal penetration for anal penetration. Ever. Ever!

(There are small bullet vibes made to fit inside flared-base buttplugs. Those can be great. Just not by themselves.)

Give that penis or clitoris some action.

Anal sex can go from “eh, I’m not sure about this” to “please do not EVER stop” if you pay some focused attention to the receiver’s other erogenous zones – or have them do it! Anal penetration introduces a whole different dimension of sensation that, when combined with a familiar known quantity, can turn a tentative newcomer into an anal addict.

Try a vibrator, stroke them how they like, or have them stroke themselves – and don’t forget their nipples, neck, and other purr-spots. Whole-body arousal is key to a transcendent anal experience.

Relax, enjoy and be safe!

Before even attempting anal, it’s helpful to be as relaxed as possible in body and mind – breathwork can help, as can massage, or even a long, intimate conversation to start. And to be truly relaxed, we need to feel safe.

Safewords are a must if you’re into kink. Anal isn’t necessarily kinky, but it helps to have a butt-stuff safeword anyway – or more than one. “Green” for “go”, “yellow” for “slow down” and “red” for “stop” are simple classics that everyone understands – and the active partner must understand, and respect what those words mean.

The real key to a great time with anal is enough time – and patience, and trust, and wide-open communication. And we can’t say it often enough: those principles apply to all intimacy, whether the booty is involved or not. 

So if you don’t feel safe, don’t do it. And if you do feel safe, let loose with an enthusiastic “yes”. There’s a hole new world to explore. Enjoy!

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