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.
There are several misconceptions about anal sex, that can put people off trying it. So let’s begin by debunking some of those myths.
1. It’s for gay men only
Probably one of the most common reasons why some heterosexual men are reluctant to try anal sex – they think it makes them gay. Just because it’s the only way gay men can have actual penetrative sex, doesn’t make it ‘theirs’ to own. In reality, straight guys have been practicing anal sex for centuries, and it was actually a sign of great virility in ancient Rome and Greece, for men to ‘take’ their women this way. Although not totally foolproof, having anal sex was (and still is) used as a means of contraception. I would, however, advise anybody having anal sex, with a new partner, especially, to always use a condom and/or dental dam, or at least get tested. Unprotected anal sex is one of the easiest ways to pick up STDs.
2. It’s only men who get pleasure from it
Wrong again. While it’s true that men experience a totally different sensation on their cocks, when they penetrate their partner anally, women can get just as much pleasure and some women even prefer anal sex to vaginal sex. The feeling of fullness a woman experiences, can be very erotic. Add in some accompanying clit play, and women often report that their orgasms are far more intense during anal sex.
3. It’s always painful
Our anal areas are very tight, with a thousand more sensitive nerve endings and muscles that will resist any attempt at entry. This is just our body’s natural defense system. With careful coaxing, plenty of lubrication, and lots and lots of practice our assholes can be trained to let visitors inside. Many people who practice anal sex don’t experience any pain at all. Just like vaginal sex, it’s all about patience, technique, and communication.
4. It’s unnatural
Sex is the most natural thing in the world, and there isn’t one ‘right’ way to do it. We should feel comfortable about exploring our own bodies, and each others’, and if something feels right it usually is. Anal sex has been around as long as ‘normal’ intercourse. There might be raised health risks, if not practiced properly but, morally, anal sex is as natural as breathing. Don’t let social constraints or perceived disapproval dictate how you enjoy yourself sexually. It’s your body, you can do what you want with it.
So, you’ve got used to the idea in your head and it’s something you really want to try, but where do you start?
• How to get warmed up for anal
A lot of people don’t like anal when they first try it, because they’re simply not doing it right. It can be very daunting the first time you either penetrate an asshole or receive a cock in your asshole. My first anal experience wasn’t good, but it didn’t deter me from trying again. I knew it was probably just a case of getting the technique right and the only way to do this was to go back and do it again, and again, and again.
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. Your asshole is even more delicate, so it needs just as much preparation before anything penetrates it.
Unlike vaginas, assholes don’t have any way to self-lubricate. Even the most passionate foreplay around this area, won’t produce any juices to make penetration smoother. 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. Just remember that most massage oils aren’t compatible with condoms, so if your guy is covering up, use a water-based lubricant instead. 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 tailbone, then pull it back down (use a warming cream for added sensation). As you massage her bum, 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 bum 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 bum used to intimate contact. Then, the idea of something penetrating her won’t seem so strange.
Another great warm-up technique, is to have your lover give you 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, then take his time licking and sucking around your asshole. He could even go further and lick along your perineum, towards your pussy, then back again. It’s teasing, but it feels amazing and every time you feel him slide back towards your asshole, you’ll find yourself wanting to open up for him. I never get tired of how delicious it feels to have my lover’s hot tongue probing my asshole. And when he gently pushes it inside of me, it’s so soft and wet and warm, it immediately makes me want to feel his cock inside there, too. So let your lover take his time and get you used to the feeling. Girls, you can do the same to your guy. Use the technique as an extension of when you’re going down on him. When you’re sucking him off, reach underneath and run your tongue along his taint, then slide yourself around the back of him and get to work on his asshole. 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. Make sure his nails are groomed, so he doesn’t pinch or catch your skin. The shorter his nails, the less chance of passing on or picking up any infection. Girls, it’s the same for you – make sure your nails are clean (and preferably short) before fingering your guy’s asshole. You want to arouse him, not scratch him.
As your ass becomes more and more familiar with how his finger feels, you’ll find that you relax enough to let him push further into you. Stay with his pinkie, if that feels comfortable, but don’t be afraid to let him try his index or middle fingers. 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.
Some women find it also helps for their lover to finger their vagina, at the same time as he’s fingering your ass. It’s a bit like asking a familiar friend to join the party. You already know how great his finger and cock feel in your pussy, so this is a way of getting your ass to feel the same. 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. Our anuses are very powerful vacuums, and some objects can get ‘lost’ up there, so always use toys designed specifically for anal play…
Solo Play – Male or female, if you’re on your own or just want to practice on yourself before experimenting with a lover, it’s just as important to be warmed up before penetrating yourself. Get your senses working by using an aromatic massage oil on yourself. Use a vibrating anal dildo to get your ass aroused and rub oil up your cheeks and legs. Prostate massagers for men are fantastic for using around your asshole, as they’re small enough to control and are just the right size for coaxing yourself into opening up.
Alternatively, while you’re in the shower, use your fingers to probe behind you and see how far you can push inside. Crouch down and use the water to help you push up inside yourself, or use a special shower dildo. You’ll get to know your own body, and discover what feels good, and which toys you’d be most suited to trying. Treat your body like you’d expect your lover to. Lie in different positions on your bed to find out the most comfortable way of reaching your asshole. Perhaps experiment with toys such as suction cup dildos, which you can attach to a wall or the floor. Using plenty of lube, gently push your asshole against the tip of the dildo until you get used to the sensation. Suction dildos are great self-trainers, the ideal anal play practicers.
• Once you’re both ready…
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. This way 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. The best vibrators for this position, that rest on your mons and clit area, are Nea or Lily handheld vibrators from Lelo.
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.
Once you’re in and she’s opened up fully you’re good to go. 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.
The above techniques apply similarly to gay men, and women and men who want to use strap-ons. Our asses are delicate pieces of apparatus and need to be treated with respect. The premise is the same – the receiver must be warmed up and relaxed, and the giver must go slow and listen, all the time, to their lover’s needs and reactions.
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. 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.
Solo play – it’s easy to get carried away when there’s no-one else to stop you, especially with anal play. Just try to remember to use anal-specific toys, like butt plugs, prostate massagers or dildos with a base (see below). Girls, you can buy anal dildos that also have clit stimulators. Once you’ve mastered the art of penetration, you’ll get double the pleasure once you get your rhythm right. For guys, you can combine anal massagers with masturbation sleeves for a very intense double orgasm. This is usually for the well-practiced, though, as it takes excellent timing and positioning to get off in both places at the same time.
For (straight) guys, it’s often a revelation to them just how incredibly sensitive their anal area is. So it makes sense for men to really spend some quality solo time on themselves, to discover what turns them on. Investing in a few anal toys, will not only get you more in tune with your body, but it will also remove any stigma attached to the idea of you as a straight guy, enjoying anal play. Once you’re comfortable with how anal play feels, you’ll be much more willing to let your lover share your enjoyment.
• How to mention anal to your partner
Whether you’re single, in a relationship, or just having fun, it can be tough to bring up the issue of anal sex, especially if you’re the man who wants his woman to fuck his ass. Many women might feel weird doing that to their partner and men may have problems saying they like it. But this awkwardness is entirely socially-constructed and nothing to do with the natural way of things.
But to be a successful lover we need to feel comfortable enough with our partners to be as open with them as possible about our sexual needs and desires. Sometimes, we do things for our lovers that we might not necessarily enjoy ourselves, like blow jobs or rimming, but we do it because we love them and want to please them. But often, we’re wrong to assume things about each other, and we need to communicate more.
Maybe you’re the one who wants to indulge in some anal play with your guy, but you have no idea how he’ll react to the suggestion. Most people assume that guys love anal sex, and any girl who suggests it, is a dream lover. But it’s not always the case. Some men see anal sex as ‘unnatural’, it’s just a question of perception and personal preference. But if we don’t talk to each other, then how will we know what each of us wants?
A good way to approach the subject is to say you’ve read an article or seen something on TV. This way it’s seen as you not having brought up the subject of anal sex, you’re just mentioning something you read about or saw on TV. Usually, a person’s first reaction to the words ‘anal sex’, will tell you a lot about their opinion on the matter. Or it might just be that the topic embarrasses them, because they’ve never done it or they feel ashamed that it’s something they do want to try, but don’t know how to go about it.
Get the conversation started and take it from there. Or, at the very least you can plant the idea in their head and let them go away and think about it. If your lover knows that anal sex is something you’ve obviously been thinking about, then they’ll start to think about it, too. You might even find some surprising common ground and you’ll both wonder why it took you so long to get around to discussing the subject. If you educate yourself on the topic, read as much as possible and maybe get other people’s opinions, it’ll show that you’re serious.
But if you’ve talked to your partner and they’re absolutely not into it, then you need to respect their comfort zone and leave it at that. You never know, they may come around later but don’t hold it against them. We all have our own preferences in life, sexual and otherwise, it’s what makes us different. Trying to convince your partner into doing something they’re obviously not comfortable with, will only ever turn into disaster.
If they aren’t into it, then there’s nothing to stop you indulging in some solo play (as above). Then, once you’re comfortable with how your body feels during anal play, you could always try introducing it to your sex life with your lover, just as something for yourself. Just as women often masturbate with a vibrator while their partner is fucking them, you can give yourself an anal treat instead. Or there are anal toys that are designed to just sit in your ass while your partner has sex with you. Once your lover sees how anal play makes your own experience that much more intense and enjoyable, they might be more open to trying it themselves. As with most issues surrounding anal sex, it’s the fear and mystery of it that often accounts for people’s negative attitudes. Remove the fear, get it out in the open, show your lover how wonderful it can be, and watch them reconsider.
• 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.
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.
The warming and cooling lubes add great sensations to anal play. 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.
Great for both solo and couples play, 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. Our anuses are powerful vacuums that can suck in objects, so always ensure that if you’re using toys back there, that they’re specialist anal toys, which have a base on them to prevent them getting lost. For beginners, try a dildo that has graduated balls, so you can slowly build up your tolerance. The more you get used to it, the more you’ll be able to insert (by yourself, or by a lover), and then maybe graduate to the more standard dildos.
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. There are so many different ways to use one and it’s an ideal sex toy for both solo play, and couples play, whether you’re same sex or hetero. For women enjoying some ‘me time’, you can insert one end of the dong into your vagina and the other into your ass, and get rocking. 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 and/or vaginas. 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.
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 on your ass, there are some great specialist anal vibes on the market now, so it’s worth checking them out. Because 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. Beginners’ anal vibes are great for getting you used to the feeling of penetration, whilst exciting you at the same time, and make great solo sex toys to build your confidence before you start experimenting with your lover. For sheer indulgence, try a triple vibrator, which will get you off three different ways – vaginally, clitorally and anally. It’s the ultimate solo sex toy, but don’t be afraid to let your lover administer the pleasure, if you want them to get involved. Obviously, women will get the most benefit from a triple vibe, but guys can play around with it, too. By using the dildo part to insert into their ass, they can then use the other parts to simultaneously stimulate their taint and/or balls.
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, 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. Many women also feel quite empowered by using a strap-on, and it can help them empathize with men when it comes to understanding the traditional gender sex roles. In addition, strap-ons can help men with erection issues. There are hollow strap-on versions available, which fit over a man’s penis, thus providing an instant ‘erection’. Guys who don’t think they’re ‘big enough’, often use larger-size strap-ons to give themselves bigger cocks.
These 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.
One of the best ways for men to get used to having their asses penetrated is with a prostate massager. They are easy-to-use, low-impact stimulators that can be used alone, or with a partner. 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. If you’re a beginner, try a slim version, which is thin enough to slide in easily and hold onto. Once you’re familiar with how penetration feels, you can then move up to the more standard massagers and dildos.
As you get more accustomed to anal play, mix things up a bit by using a dual penetrator. Similar to triple vibrators, 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. For solo play, simply insert one end into your vagina, the other into your ass, and switch on the motor – you’ll be on your way to heaven in seconds. For couples play, let your lover take charge of it, so he can move it in and out of you while you lie back. 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.
Not everyone feels comfortable with feeling a bare finger pushing into their ass. With toys it’s different, but feeling someone’s finger inside you is just as intimate as feeling a cock, so you have to be comfortable. You could try getting your lover to wear a latex glove. This offers both protection from infection (from fingernails or infections passed from skin to skin), and added smoothness. Latex gloves also invite 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 can be used to tease and probe the outside of 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. But make sure your finger is secure in the finger holder and only insert it a little so that it doesn’t slip in your ass. 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.
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, the best way to become a master of anal play, is not just to practice lots, but to educate yourself. Invest in a few great anal sex books and learn about new techniques, get your anal sex questions answered, and just get educated about the natural wonders of anal play. There are still so many taboos surrounding anal sex, it’s something forbidden, something mysterious and something ‘dangerous’. But it really isn’t, on any count. 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® – The Single Girl®: Your Naughty Lifestyle Guide