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The Anal Sex 101


Anal sex can be one of the most intense sexual pleasures you’ll experience.

For many people, especially women, anal sex still remains somewhat of a taboo subject. It’s one of those things that lots of us want to try, but are either afraid of what it entails (and if it’s going to hurt), or we just don’t know how to get started, and do it right.

Anal sex can be one of the most intense sexual pleasures you’ll experience, for both men and women. Communication is key – both of you have to feel comfortable with each other, and talk about what you both want from it, before you commence. If one of you is more experienced than the other, use your knowledge to allay any fears your partner has. If you’re both new to anal sex, go slow, and just enjoy exploring each others’ bodies incorporating anal play into your foreplay. Getting used to being probed back there is essential if your body is going to relax enough to allow full penetration. It’s a good idea to just spend a few sessions playing with each other, before you go the whole way. Your body needs to sync with your brain, when it comes to anal sex. If one is relaxed, the other will soon follow.

You don’t have to have a partner to enjoy anal sex. With so many great toys and aids out there you can indulge in some amazing solo play in a time and place to suit you. Solo anal play can also prove a vital tool in ‘training’ yourself in anal penetration. The more your body gets used to it, the more relaxed you’re going to be when it comes to enjoying the experience with someone else. Even if you’re in a relationship, don’t be afraid to enjoy some solo time so you can practice techniques that will improve your performance.

1. Get Warmed Up

Men have a tendency to think that a woman’s asshole is like her vagina – a hole they can just shove their cock into, and get pumping. But think about it, guys. When you have standard intercourse, do you really just stick it in, without you both getting prepared first? And, girls, you wouldn’t seriously let your lover just thrust up inside you with no foreplay, arousal, or any kind of warm-up, would you? Your vagina needs to be wet, either naturally through foreplay, or with lube, so that your vaginal canal can take his cock without your delicate cervix getting hurt. Unlike vaginas, assholes don’t have any way to self-lubricate, you have to do it yourself. Just as your lover would use his hands or tongue to get you warmed up between your legs, he needs to do the same with your ass.

One way to do this, is to have your lover give you a bum massage. You can use different oils or lubes as you massage her cheeks and asshole. There are plenty out there that smell (and taste) nice, which will add to the air of arousal. You just might need to use more of it, as water-based lubes absorb into the skin much quicker than oil-based ones. Erotic massages are the perfect way to get you and your lover warmed up for any kind of sex, so check out the special bum and anal techniques in these books, to ensure your foreplay gets off to the best start.

Guys, get your lover to lie down on her stomach, then start rubbing her ass cheeks in a small, circular motion, gradually increasing the circles every 30 seconds or so. Gently pinch an area of her buttock and push it up towards her coccyx, then pull it back down (use a warming cream for added sensation). As you massage her butt, use your thumbs to gently part her cheeks. Then, when she’s used to you pushing between her buttocks, let your thumb linger by her asshole. Don’t try and penetrate her, just push into the deep crack of her butt cheeks, almost brushing her asshole and feel how her body reacts, making sure to keep the rest of your fingers working the softness of her upper cheeks. The point of the massage, is to relax her, and get her butt used to intimate contact. Then, the idea of something penetrating her, won’t seem so strange.

You could also try giving your lover a rim job. ‘Rimming’ (correctly called ‘anilingus’) is when a person uses their mouth and tongue to lick and suck around the anus and perineum of their partner. It’s obviously a very intimate practice, but it can be such a powerful turn-on, and just perfect for warming up your asshole, getting it relaxed, so it’s more receptive to penetration later on. Have him spread your ass cheeks, so he can take his time licking and sucking around your asshole, then along your perineum, towards your pussy. It’s teasing, but it feels amazing. Girls, you can do the same to your guy. Most men will not have had a woman do this to them before, so they’ll be surprised at just how great it feels. If your guy has never thought about being anally penetrated before, this is a fantastic way of introducing the concept to him.

Once he’s rimmed you with his mouth, and you feel yourself relaxing, have him toy with your entrance, with the tip of his finger. His pinkie is the ideal size to go probing with, and all he has to do is touch your opening, to gauge your reaction. For your first time, you might find that your asshole wants to close automatically, but if he’s already done a great job with his mouth, you’ll probably feel relaxed enough to let his finger enter you slightly. Get him to keep his finger there, just on the edge of your hole, as you get used to the feeling, then maybe push your ass further onto it, when you feel comfortable doing so. Whoever’s fingering who, make sure your nails are short, as there’s less chance of passing on, or picking up, any infection.

The biggest hurdle for novices, is getting past that first penetration, however shallow it is. Once you’ve done that, the idea of full anal sex suddenly doesn’t seem so strange, or frightening. You could also try using an anal sex toy, to relax your asshole and get used to feeling penetration. Proper anal toys have wide bases, something to hold onto, so the toy doesn’t get sucked in.

2. Go slow

Now you’re completely warmed up, and heavily lubricated, and your asshole is ready for his cock, remember to go slow. He might be so excited by the sight of your wet asshole waiting to receive him, that he can’t wait to get in there, but remember, it’s your ass, and you are in control. Just because he’s spent the last half an hour with his head in there, doesn’t mean his cock gets to jump straight in, after.

Guys, gently place the head of your cock inside her asshole, very slowly. The art of perfect ass penetration, is to rock, not just push. Imagine her asshole has 5mm markers leading into it. All you have to think about, is reaching the next marker, by rocking into her delicately. Once you’re a bit further in, pull back a little, but never all the way out. Always stay in her ass, but rock a tiny bit further in each time, before pulling back again. This gets her ass used to the in-and-out motion of your cock, and will continue to relax her muscles and sphincter, as you reach further inside her.

With each ‘marker’ reached, you’ll see your head disappearing inside her, but try and stay focused. Once your head is all the way in, you’ll be tempted to think the difficult bit is over, and you can just get thrusting. Instead, you need to keep slowly rocking, in and out, inching further up each time. Once you’re inside, you need to stay inside, unless she’s more advanced, otherwise you’ll find yourself having to start all over again.

I can’t emphasize enough how crucial it is to go slow. She needs to get used to feeling something in her ass. Some women feel like they need to poop, the first time they do anal, but this feeling will pass. It’s a muscular reaction, nothing more. Contrary to popular belief, our asses are not storage containers, they are channels, so there’s nothing else up there you’re going to run into. For novices, it helps if the woman is lying on her stomach as you enter her ass. She can use a vibrator on her clit, as you penetrate her, which distracts her from any initial discomfort. The more practice you both get, the less she’ll need to do this.

So, once you’re inside her, pump your cock further in, slowly, centimeter by centimeter, and see if you can feel her relax underneath you. Once the initial penetration is done, and you don’t slip out of her, her ass will quickly learn to accept your cock and then start opening up further to receive you fully. There should be no rush, guys, because if you’re past the initial phase, you’ll get to the rest in good time. Just make sure to stay inside, because if you do slip out, it’s not always the case that you can just slip back inside, like you can in a vagina.

Her sphincter will close up tightly and you’ll often have to start the whole process over again (even though it should be easier, second time around). Remember, always communicate with your partner. Ask her how it feels, if she’s comfortable, and if she’s ready for you to start pumping her.

3. Enjoy the intensity

It’s now that you’ll both experience how intense anal sex can be. For guys, their cocks definitely benefit from the added tightness of your lover’s asshole, and your head will feel super-sensitive. For girls, that feeling of fullness is very satisfying, and you should also feel quite a bit of pressure inside your cervix and around your G-spot. If you’re on your stomach, your clit should be getting some automatic attention as he thrusts into you and presses your pussy to the bed/sofa/floor. Or have a bullet vibe handy, so you can play with yourself as he fucks you.

Things to try for anal sex

Whether you’re a beginner or a seasoned pro at anal play, using sex toys and other aids can greatly enhance your experience. Try the products listed below, and see which toys are best suited to you and your partner. You might discover different ways to play, or products that can add an extra dimension to your enjoyment.

1. Anal Lubes / Warming & Cooling

Lubricants are essential when engaging in anal play, and the more the better. Our assholes are tight and dry, and the body has no means of producing natural lubrication back there. So do make sure to stock up with lots of lubricant, the special sort made for anal play. Anal lubricant comes in many forms – sprays, gels, creams and even butter, as well as the standard lotions. Lubes can be scented and flavored, so oral anal play is a bit tastier for the giver. Some lubes also have desensitizing agents to slightly numb the asshole which, despite making insertion easier, can also mean the receiver isn’t totally aware of how their asshole is feeling, so beginners might want to avoid these, so they can stay in total control of their own comfort.

Warming lubes can make assholes extra-sensitive, and really get you both going. Feeling your ass heat up as your lover plays around with you, is just incredible and super-horny. It also helps relax you, to make your asshole more receptive to penetration. To make your playtime last even longer, try a cooling lube, which spreads a relaxing coolness all around your body as you both play. It can help keep your asshole stimulated and relaxed, and the more lube you use, in whatever form, the easier it will be to try different things.

2. Anal Dildos

Anal dildos are specifically designed for ass play. You should not use standard dildos when indulging in anal sex, because there is a danger you could lose the toy inside your lover. Glass dildos, in particular, feel sublime, so cool and smooth, and are definitely for those who like to add a touch of luxury to their anal play.

3. Double Dongs

Get double the pleasure by using a double dong. It’s a length of flexible jelly or plastic, usually either 12in or 16in long, with a helmet at either end. Couples of both sexes can get off on double dong-play, with one end in her vagina, the other in his ass, or both ends in your asses. It can be tricky to use double dongs together, but you just need to practice – a lot. Once you get the hang of it, then mutual pleasure is pretty much guaranteed.

4. Anal Vibrators

Fantastic for really cranking up the sexual teasing and tension, vibrators are an essential component of any sex toy box. While standard vibes will usually do the trick, our assholes have a shape and feel all their own, it makes sense to use a vibe that’s designed to get right in there and stimulate you to the max.

5. Strap-ons

Just brilliant for role play and advanced experimentation, strap-ons can be used by couples of any orientation, to enhance anal play. They’re a favorite with gay girls, who like to indulge in both vaginal and anal sex with their lovers. But there are plenty of straight guys out there who love a bit of anal play, too, so a strap-on is the ideal way for his lover to satisfy his urges. It might feel strange for a girl to put on a cock to ass-fuck their guy, but if you’re open-minded and keen to see just how much pleasure he gets from it, you’ll soon be more than a willing participant, and they’re great for making you feel in control. Vibrating strap-ons are a must-have for experienced anal lovers. Once you’re used to being penetrated, the added vibe will really give your ass a good workout. But for the ultimate strap-on climax, go dual, and use a double dong strap-on. The woman straps it around her waist, with one end inserted into her vagina, then uses the other end on her lover’s ass. Both of you get fucked at the same time, with multi-speeds to control your excitement levels. With a bit of practice and control, you’ll get to achieve what most couples dream of – simultaneous orgasms.

6. Prostate massagers

One of the best ways for both men and women to get used to having their asses penetrated, prostate massagers are easy-to-use, low-impact stimulators. Prostate arousal is usually associated with men, because their prostates (just inside their assholes) are considered their G-spots (sometimes called P-spots). You can buy massagers with small, smooth heads, which slot easily into your asshole, or larger, thicker versions, similar to dildos, but which are shaped to specifically target the prostate once inside. Some come with vibes attached, and also have perineum stimulators, for dual pleasure. Women, too, can use prostate massagers to get their asses used to penetration.

7. Dual Penetrator

Mix things up a bit by using a dual penetrator. Similar to double dongs, these are two-pronged vibrating dildos, primarily designed to give a woman dual penetration climaxes. They come in jelly or PVC/plastic material, so they’re really pliable and flexible. Let your lover take charge of it, so he can move it in and out of you while you lie, or stand back, at ease. Step things up a bit, and maybe use it on your guy’s ass while you suck him off. The vibrating motor that sits between the two penetrators will also work his taint to the edge of distraction. Acrobatic couples could master how to use it on both of you, one inside her vagina, the other in his ass. Difficult, but definitely possible.

8. Fingers!

Feeling someone’s finger inside you, is just as intimate as feeling a cock, so give it a try. Wear a latex glove to protect against infection, and ensure smoothness of entry, and maybe indulge in some sexy anal role play – the sexy doctor or nurse examining a patient. Incorporate this into your foreplay, and you’ll find it a lot easier to relax. Alternatively, try some finger vibes, to get your lover used to how fingers feel inside them. They’re finger-shaped vibrators, soft and malleable, that slip easily into your lover’s asshole and will quickly get them worked up. You can also use them on yourself, to practice what feels comfortable. Because they’re small and light, they’re the perfect toy to experiment with, if you’re new to anal play. Just play around with the outside of your asshole and, as the vibe gets to work stimulating your opening, try pushing a little further inside each time. You should still use plenty of lube, but the vibrator should really help to relax your body and make further insertion a lot easier. Great practice toys.

9. Dental Dams

Your tongue is one of the most sensuous organs in the body, and it’s just fabulous for giving amazing oral anal sex to your lover. It might feel off-putting at first, placing your tongue in your lover’s asshole, and there are obviously health issues, too. So it makes sense to use a dental dam, to both play safe, and make yourself more familiar with pleasuring your lover’s ass, orally. Dental dams are very thin sheets of plastic (usually latex) that you place over your lover’s asshole or pussy. It protects your mouth from coming into contact with any secretions, just as a condom protects a cock. Many people think that using a dental dam, lessens the sensations to the receiver, or that they’re just unsexy, but that doesn’t have to be the case. The dental dam is so thin, that your tongue will be able to give as much pleasure to your lover, as it would if it was just tongue on skin. And many dental dams come flavored, which makes the experience much more pleasurable for the givers, and are great for beginners, as they get used to giving oral sex.

As a final piece of advice, invest in a few great anal sex books to learn about new techniques. You’re on a mission to deliver presents this December, so if you want to make sure your generosity is wrapped up in the biggest, sexiest bow possible, get educated! Anal sex is safe, amazing, erotic, and suitable for lovers of any gender and any persuasion. Take away the mysteries of anal play, and open up a new world full of light, sexiness and erotic intensity. As I like to say often, knowledge is power, so the more you know, the more pleasures await you.

Sienna Sinclaire ~ Naughty Los Angeles Sex & Dating Coach

This article was originally published at Naughty Lifestyle Guide. Reprinted with permission from the author.


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