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How To Have Pain-Free Anal Sex

12 Tips & Techniques For Beginners

 This guide on how to have anal sex is long, BUT it has everything you need to know. You’re going to learn the difference between having deeply satisfying anal sex that gives you full body orgasms and having anal sex that is painful and messy.

First, I’m going to talk about some of the fundamentals for having great anal sex, then we’re going to cover the actual anal sex techniques and positions you should be using during the act. I have also created a separate guide here on how to full prepare your body for anal sex (hygiene, etc.).

Now, on to the fundamentals…

1. What You Need To Know About Anal Sex – The Pros And Cons

There are a bunch of really awesome things you’ll discover as you start learning how to have anal sex, but there are also a number of drawbacks that you should be aware of too. Let’s start with the pros:

Anal Sex Pros 

  • A Different Type Of Orgasm – Many women have much more intense orgasms from anal sex. I can’t fully explain why this is. I do know that there are thousands or nerve endings in your anus, but there are even more in your vagina and clit. So if you currently struggle to orgasm from regular vaginal sex, then you may find anal sex to be way more pleasurable.
  • The Kinky Factor – Another very appealing aspect of anal sex is the “kinky factor” or the taboo of doing something that you “shouldn’t.” Breaking taboos can be a lot of fun and major turn on in itself. Many people don’t see it this way, but if you do, then it’s just one more reason to have anal sex with your man. 
  • The Replacement – Often, vaginal sex is out of the question. You may not want to have it if you are on your period. You may have a UTI that you don’t want to aggravate. You may even be sore from a previous session. This is when anal sex becomes the perfect back up plan. 
  • No risk of pregnancy – This one is obvious, but anal sex means that there is almost zero chance of pregnancy.

Anal Sex Cons 

  • Needs Planning – One of the biggest problems with having anal sex is that it requires some planning. You probably don’t want to try anal after a big vegan lunch. You are also going to want to do some preparation beforehand, especially if it’s your first time to make sure you’re clean and that it’s not painful. This guide will teach you everything you need to know about getting prepared for the act before you even try it with your man. 
  • His Obsession – Some guys seem to have an obsession with anal sex, especially inexperienced guys. For many guys like this, it’s a box for them to tick and something they can brag to their friends about. If you are not particularly keen, but your man is obsessed, then dealing with this pressure can be a real turn off. 
  • Some Love It, Some Don’t – Some women really adore anal sex. They find it incredibly pleasurable, while others don’t find it pleasurable at all. It comes down to personal preference, so if you try it and don’t enjoy it, that’s fine. There’s no need to stress about it if you don’t get much stimulation from it. Instead, try something else!

2. Do You Even Want Anal Sex? 

Many women aren’t interested in learning how to have anal sex. Instead, they’re just doing it to keep their man happy. In fact, they may be more than simply disinterested in the idea of anal sex, they may dislike and even hate the idea.

While I always recommend trying out new things at least once to see whether or not you like it, you should never feel forced to do anything you don’t want to do. The same goes for anal sex.

So, if you never want to try anal sex or if you’ve tried anal once and didn’t enjoy it, then don’t feel that you have to keep doing it with your man. If your sex life consists of you doing things that you don’t want to do, then it’s not going to be a particularly satisfying one. Like I mentioned previously, there are plenty more things you can do with your man. 

3. Communication, Seriously 

Learning how to have good anal sex requires great communication with your man. This is going to be mostly one way communication by the way.

You are going to be telling your man what to do AND what not to do. So you need to be comfortable with the idea of telling your man:
  • To slow down
  • To pull out slowly
  • To completely stop moving
Your man also needs to be someone who will actually follow your instructions too. If he thinks he is going to be in control and calling the shots, then you are going to have to bring him down to earth and let him know that this won’t be the case. Doing this isn’t so that you can “dominate” your man, it’s so that you get to experience the pleasures of anal sex AND NOT THE PAIN.

4. The Four Types Of Lube 

Using some kind of lube during anal sex is almost always necessary. However, not all lube is made equally, there are four types and choosing the right one plays a significant role in your pleasure. 
  • Water Based Lube – As you can probably guess, water-based lube is made of mostly water. This makes it safe for anal sex, but it’s not perfect. The problem with water based lube is that it dries out quickly and then needs to be reapplied. Stopping to reapply lube can obviously ruin the vibe. You CAN use water based lubes with latex condoms as it does not degrade them. It’s also easy to wash out. 
  • Silicone Based Lube – Silicone based lube is the lube I recommend you use when having anal sex. It’s compatible with latex condoms, so you won’t degrade them. It also lasts much longer than water-based lube, so you don’t have to worry about reapplying it either. It also feels super silky and smoother than many water-based lubricants. The only slight drawback is that it can sometimes be a little hard to wash out of your bedclothes. 
  • Oil Based Lube – Oil based lube feels a little smoother and silkier than water-based lube. It also lasts for ages, so it’s perfect for anal sex, but there are some significant drawbacks. It’s much harder to wash out of linens. More importantly, oil-based lube degrades latex condoms making them tear and rip. Bottom line, if you don’t want the condom to tear during the act, then don’t use an oil-based lube. 
  • Saliva – I decided to included saliva as often you may not have access to lube and need a backup, especially if you are having a quickie. It’s water based and so is compatible with latex condoms. It probably shouldn’t be your first choice because it will dry up and isn’t plentiful, but it works fine. 
Here’s how we rank the different types of lube beginning with the most enjoyable and useful lube:
  1. Silicone based
  2. Water-based
  3. Oil based (if not using condoms)
  4. Saliva

When picking a lube from the shelf, you’ll see that some of them contain spermicide. The point of this ingredient is to kill sperm and prevent pregnancy, which has little risk with anal activity. However, most lube that is spermicidal has ingredients that are harsh on your sensitive genital and anal cavities, and even lube without spermicide can damage cells. This damage makes it easier to contract STIs such as HIV. Avoid lube with spermicide for anal or any other sexual activity

Unfortunately, even lubes without spermicide can damage the tissues in your anus. This is due to osmolality, a rating of particulates dissolved in solution. Every orifice or tissue in your body has its own osmolality, and the rating differs between your anus and vagina, so you might want different lubes for each activity.

Good Clean Love is a healthier option, and Yes But and Sliquid Sassy are designed to be safe especially for anal sex. You can also try Aloe Cadabra as slow-osmolality lube for anal sex.

5. Pain-Free Pleasure 

This section is by far the most important part of the anal sex guide. Don’t skip it.

Many people report anal sex feeling painful and the reason for this is your anus. There is a ring of muscle in your anus called the sphincter that keeps it tightly closed. This muscle is NOT like your bicep or hamstring muscles that you can quickly relax and contract in a split second.

Instead, it takes quite a while for it to relax and allow things to pass through it. Think of it as a very strong, but very slow muscle.

If you try to pass something through it quickly (your man’s penis) when it’s closed, then it won’t have enough time to relax, and this will cause a lot of pain.

So, the key to having pain free anal sex is getting your sphincter muscle to relax and open up enough so that your man can enter you with ease. Here’s how:

Start With A Lubed Finger – If you read the Anal Sex Preparation Guide here, you’ll know that it’s best to try penetrating yourself ALONE first with a finger covered in lube so that you get to see how your sphincter reacts to it. If you’ve already done this a few times and have a good idea of how long it takes to relax around your finger, then you can get your man to do the honors this time. If you haven’t done it by yourself yet, then I recommend that you try it alone first.

He needs to apply a bit lube to the tip of his finger and some more to your ass. Next he needs to slowly slide his finger inside you, millimeter-by-millimeter, while you give him feedback, telling his to go deeper or to stop moving or to SLOWLY pull out (pulling out fast can cause some pain, he needs to do it slowly).

As he slowly penetrates you deeper and deeper with his finger, it should feel reasonably comfortable.

If it becomes slightly uncomfortable, then tell him to stop moving and to keep his finger still for a minute or two. This will allow your sphincter to relax around his finger and open up. When the pain subsides, he can push a little deeper.

If it becomes too uncomfortable and painful, then tell him to pull his finger out slowly. Rest for a minute or two and then get him to start over.

Thrusting – When he can’t penetrate you any deeper with his finger, he needs to slowly thrust in and out. Again you should control the pace here, so tell to him either speed up or slow down, depending on what you want.

Double Up – Once you are comfortable with your man thrusting in and out, he needs to try adding a second finger. Again, he should be very slow and cautious doing this, following your instructions and feedback to either continue, slow down, stop or slowly pull out.

Once he can easily thrust in and out with his two fingers, then either try three fingers or you can start having anal sex.

Don’t Numb – You might be tempted to reach for a product that numbs your anus for anal sex. However, these products aren’t lubricants and prevent you from knowing what is happening with your body. You could potentially be numb when a serious tear has occurred. Numbing ingredients may also be irritants.

6. He Should Start On His Back 

The most comfortable position to start having anal sex is with your man on his back so that you are in control. This means that it’s a lot harder for him to thrust into you and it’s much easier for you to control how deep you take him and how fast he thrusts.

So get him to lie down on his back and ask him NOT to thrust into you. Instead, he should remain still.

After applying some lube to your man and your backside, you can then straddle him on your knees like in the Cowgirl position or even the Asian Cowgirl position.

Grab hold of his penis and then slowly guide it inside your anus. Make sure to take your time. As I mentioned above, if you feel uncomfortable or experience any type of pain stop and allow your sphincter muscle to relax around his cock. Once it has, then you can try taking him a little deeper.

When your man is completely inside you and can’t go any deeper, you can slowly raise your body up and down.

The main thing here is to take things slowly. You don’t want to hurt yourself, so if you experience any discomfort at all, slow right down and even stop to allow yourself to relax. Meanwhile your man should stay lying down on his back, not thrusting.

Once you do feel comfortable moving up and down on your man, then he can start to get involved a little more by thrusting himself. Remember that you still need to be in control here. So if he gets too carried away, tell him to slow down or stop.

And that’s it!

This is the easiest and smoothest way to learn how to have pain free anal sex. But let’s not stop here…

It’s time to change gears and learn some advanced anal sex techniques so you can discover how to have deeply satisfying anal sex and enjoy body-shaking anal orgasms.

7. The Best Anal Sex Positions 

Having anal sex in the Cowgirl or Asian Cowgirl positions is fine, but if they are the only positions that you use, then you are missing out on a lot of fun.

  • Stay On Top – Here are ten more positions where you are sitting down in your man’s lap that you can try during anal sex. You might also enjoy these 13 positions where you are on top of your man
  • From Behind – Once you are comfortable with your man having more control and doing all the thrusting, then you may want to try out some doggy style type positions, where your man is fucking you from behind. I’ve put together an entirely separate guide on the 19 best anal sex positions here where you are in the doggy style position or a variation of it. 

8. Advanced Anal Sex Techniques 

Once you master the basics of anal sex, it’s time to switch gears and start experimenting with new and more pleasurable techniques to make your orgasms more intense and enjoyable. 
Your Clit – During anal sex, your clit is not going to be stimulated as it’s almost impossible for your man to maneuver his body into a position that stimulates it with each stroke. With this in mind, here are a few alternative ways to stroke it.
Your own hands – After all, you know what type of stimulation your clit responds to best!
His hands – If your man is using one of these 19 anal sex positions, then all he needs to do is reach around and start rubbing and massaging your clit and vagina.  
Vibrator – Using a vibrator is a super satisfying anal sex technique. You get to feel every inch of your man inside you while at the same time you get to feel the power of your vibrator on your clit. This can lead to some really intense orgasms. Here are 9 deeply satisfying ways to use your vibrator during sex.
Try Some Toys – Your man’s penis isn’t the only thing that can stimulate you anally. There are numerous toys you can use during vaginal sex that will give you incredible anal pleasure such as: 
  1. Butt Plugs – These are tapered toys with a flared base that you insert anally and stay in place. If you like the feeling of ‘fullness,’ then you will enjoy using a butt plug during sex. Most sex shops also sell vibrating butt plugs.
  2. Anal Beads – These consist of connected round beads, almost like a necklace that you insert into your anus and then pull out. Many people find that pulling the beads out during orgasm enhances it.
  3. Lube Launchers – These resemble syringes and are used to get lube inside your anus before anal sex so that your man’s penis or your toys slide in easier. 
Double Penetration – If straightforward anal sex isn’t enough for you, then you should try double penetration where you are being penetrated both anally and vaginally at the same time. If you don’t like the idea (and loss of control) that comes with having two men at the same time, then using a dildo in your vagina while your man penetrates you anally is the perfect substitute. 

When Alcohol Can Help – I don’t generally recommend mixing alcohol and anal sex, but if you are nervous or anxious beforehand, then drinking one glass of wine or one beer beforehand can do wonders at alleviating those nerves. 

Anal Training – Many women adore having anal sex and experience powerful orgasms from it while others find it too uncomfortable to orgasm and enjoy it. The reason for this pain and discomfort is simple. If you rarely have anal sex, your sphincter never gets used to relaxing for your man’s penis. This means that each time you have anal sex, it feels like the first time for your sphincter and it never learns to relax fully and open up. The only way to overcome this is to have anal sex regularly. This way your sphincter will get used to being full and relaxing around your man. If you don’t get a chance for regular anal sex, then my advice is to try using a dildo with a flared base (so that it doesn’t get sucked inside you) or use a butt plug when masturbating to train yourself anally. 

9. Anal Sex Sweet Spot 

Once you have tried anal sex with your man a few times, you’ll start to notice that your sphincter relaxes more rapidly and that having anal sex becomes more and more enjoyable for you.


When this starts happening, then you need to start doing some experimentation so that you learn how to get maximum pleasure from anal. The easiest way is to try new positions.

As well as trying new positions, you need to try some of the following things:
  • Experiment with short, shallow strokes as well as long, deep, penetrating strokes to see what you prefer. Most couples find that they actually love alternating between both.
  • Experiment with different angles. Does a particular angle feel better than the rest? Do a little experimentation to see what you prefer.
A great anal sex tip is adding in a little dominance and submission play. You may find that anal sex is way hotter when your man is dominating you or vice-versa.

10. Anal Sex Safety 

Anal sex can be a huge amount of fun, but there are a few safety considerations to take into account. I know this may sound like one of my less interesting anal sex tips, but safe sex is no joke.

Condoms – Unprotected anal sex is considered a high-risk activity for spreading sexually-transmitted infections (STIs) and disease, more so than vaginal sex, because the anus is more delicate that the vagina. In fact, the CDC considers anal sex the riskiest sexual activity for transmitting HIV, especially as the receiver who is 13 times more likely to contract HIV.

Other STIs that you can get from anal sex include:
  • Chlamydia 
  • Genital herpes
  • Genital warts
  • Gonorrhoea
  • Syphilis
  • Hepatitis B
  • HPV, which can present as anal warts

Not only can pass infections to you, but you can pass them to him (HIV can be transmitted through rectal fluid), so I strongly advise that you wear condoms during anal sex. Some people go as far as to say you can never have 100% safe anal sex without one.

Your partners might be hesitant to use condoms during anal sex because there isn’t a pregnancy risk (and people use condoms more often for vaginal than anal sex when asked about their last intercourse experience). But safety should be a priority when it comes to sex.

You can use female condoms during anal sex, but some of them are more likely to slip or cause bleeding.

As I mentioned earlier, you should NEVER use oil-based lube with latex condoms. Doing so will degrade the material leading to tears and breakage. Stick to silicone and water based lubes.

If you prefer marathon sex sessions, you may want to use new condoms more frequently than with vaginal sex. Anal sex may be more likely to rupture a condom.

Don’t Double Dip – Switching from anal sex to vaginal sex without changing condoms and thoroughly cleaning his penis is going to lead to an infection known as bacterial vaginosis. It’s also important to not that anal intercourse among women who have sex with women is associate with a higher likelihood of them having bacterial vaginosis. I think it goes without saying that fecal matter in your vagina is a bad idea. The same applies to oral sex. If you want to switch from anal to giving him a blow job, you need to thoroughly clean his penis first otherwise you risk infection.

Toys – The above advice also applies to using sex toys anally. Using a dildo/vibrator/butt plug anally and then switching to some vaginal penetration is going to require a thorough clean first. A quick way to do this is to cover the toy with a condom completely and tie the end to create a seal around the toy. Then when you are finished using it anally, carefully take the condom off and replace it with a fresh condom. Then you can safely use it vaginally. Although fecal incontinence is one and anal cancer is another risk of anal sex, following safety precautions minimizes risks for side effects of anal sex.

11. Communication & Feedback 

I am always surprised at how couples often don’t talk about their sex life with each other.

A lot of guys don’t understand the potential for pain or that you need to allow a few minutes for your sphincter to relax. Many couples talk about these kinds of things indirectly and never fully express their wants and needs.

Being indirect is not a huge problem, but often giving each other more specific feedback would be much more helpful.

If there are certain aspects of having anal sex that you don’t enjoy, make sure your man knows. Instead of saying, “It was ok” be more specific.

“I need more time to relax around your penis” or “Your penis was a bit too big for my first time, so it felt quite painful” or “Next time, I’d appreciate if you don’t thrust at all and let me control the rhythm”

Make sure to ask for his feedback too. As you both figure out what went wrong AND what went right, you can both change things up so that it becomes more and more pleasurable over time. I’m talking about positions, who’s in control, how fast or deep your man thrusts and what other techniques he uses.

This advice isn’t just for anal sex by the way. You should apply it to your every aspect of your sex life. This way you can both discover how to keep satisfying each other.

On the subject of better communication and giving each other feedback, you may realize that you absolutely hate anal sex. Keeping quiet about it is not a splendid idea. Instead, you should let your man know in a straightforward, non-judgmental, non-confrontational way how you feel about it. The same goes if you adore it, make sure to let him know!

12. Anal Sex For Guys 

Women aren’t the only ones who can orgasm from anal sex, many guys can too. Men have a gland inside their butt called the prostate gland that is highly sensitive and many guys find it incredibly pleasurable to have stimulated. Girls don’t have a prostate gland.

So, if you and your man are open minded, then you may be interested in penetrating him with a strap-on. Penetrating your man anally with a strap on is called pegging and it’s very much like anal sex for you, some guys love it, while others aren’t so interested. It also means that all of the advice above applies to pegging your man with a strap-on. 

Of course, if you want to give your man some anal stimulation, you don’t have to go straight to pegging him. There are other ways to do it. He can try inserting a butt plug. Or if you like, you can insert a lubed finger in his ass during sex or during a hand job or a blow job.

13. Now What? 

That’s pretty much everything you need to know about how to have anal sex with your man that is both satisfying and fun. If you want to learn some more helpful techniques and tips to prepare for anal sex, then make sure to read this guide here.

And if you want to learn some fun and pleasurable anal sex positions, then this picture guide will teach you everything you need to know. 

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