How To Enjoy Anal Sex:
Make It Pleasurable Instead Of Painful

Hi Ladies! Let’s discover how to enjoy anal sex!... Anal sex should be a pleasurable sex experience not a painful one. If it hurts, something is being done wrong. (Guys click here)

Anal sex has a bad reputation as far as being taboo, dirty, and painful. The reality is that there’s nothing wrong with practicing this sexual activity, and it shouldn't be painful for you... If it’s done right.

There could be some normal discomfort at the beginning, especially the first few times while you learn how to relax your body, and while your anus gets used to the penetration, but other than that, anal sex shouldn't be painful... If it hurts, you guys are doing something wrong.

Either he’s not using enough of a good lubricant, you’re not relaxed enough, or he’s going to fast or too hard.

Most of the things to make anal sex pleasurable instead of painful for you will depend on your partner, but you still need to know them, so let’s check them:

7 Important Things On How To Enjoy Anal Sex

1. He must relax your mind

Relaxation plays a crucial role in anal sex for you to feel pleasure instead of pain. He needs first to relax your mind to be able to relax your body.

The first step for you to be relaxed is communication.

Yes! You guys need to talk about it in advance, and you both must have previously agreed on trying anal sex; so you’re mentally open about it and ready for it.

You won’t be relaxed if you’re not sure about having anal sex. For this kind of sexual activity, no matter how much he wants it or how much you want to please him, if you’re not convinced or if you’re scared, this will definitely be painful.

This is the kind of sex that requires for him to really take your time to make you feel comfortable enough to try. Make sure he assures you how gentle and careful he will be.

He must be willing to do only what you want and at the pace that you want it. Make him promise you that he will stop if you want to. Make sure he builds up trust, to make you feel comfortable enough to give it a try.

2. He must relax your body

After relaxing your mind, now he needs to relax your body for your anus to be able to accommodate his penis. If you’re tensed up, your anus will be tensed up as well, and the penetration will be very difficult and extremely painful.

Therefore, once you’ve agreed to try it, make sure he relaxes your body with lots of foreplay. He needs to take his time here, and do everything you like to arouse and relax you.

Enjoy all the kisses and caresses all over your body. Also, massages and oral sex work wonders here to get you warmed up.

3. Find a comfortable position

Finding a comfortable position is key for successful anal sex. Choose a position where you can be totally relaxed. You shouldn't be worried about holding the position.

Remember that the most relaxed you are, the more enjoyable and less painful it would be for you.

Also, make sure you guys chose a position that facilitates penetration. The easier the access, the less pain or discomfort you will feel.

Doggy style is a good option. It facilitates the access and is comfortable for you, especially when you put pillows under your belly, so you can just lie and relax.

4. Use lots and lots of lubricant

Have ready a good anal sex lubricant. Never attempt to have anal sex or any kind of anal play without using a lubricant.

Your anus is actually not designed for having sex; therefore, it doesn’t lubricate itself. If he doesn’t provide lots of good lubrication, it would be very painful for you, and he may even end up tearing something inside or outside your anus.

* A water-based lubricant is a good option because it will not break the condom.

* Oil-based lubricant is not the best option if he’s using a condom because oil will break the latex.

* Lotions and creams are way too thick and won’t do here.

* His spit is not enough lubrication for anal sex. You need the lubricant.

* The best option here will be a silicone-based lubricant. This one makes the penetration easier and won’t break the condom.

Make sure he pours lots of lube in your anus, as well as, in his penis, fingers, and toys (if you’re using them).

5. He must relax your “butt area” with his fingers

Now that your body is relaxed, and you’re in a comfortable position, he needs to relax your “butt area”. Let him caresses, kisses, and massages your butt, and slowly starts using his fingers.

Make sure he puts lots of lube on you and his fingers, and starts first using his pinky; then, let him go very slowly and gently, giving you time to get used to the sensation. Now, he may switch to his ring finger.... And then, his middle finger.

This kind of stimulation will gradually open and relax your anus to be able to handle something bigger... His penis.

When he starts fingering her, it is the moment for you to breathe deeply and relax all your muscles, especially the ones outside and inside your anus. 

Hopefully, he will do everything he can to get you relaxed, but in the end, it will depend on you, so breathe and relax!

The more you’re relaxed, the more these muscles will expand and be able to accept the penetration.

Let him use his fingers to massage your anus, and always tell him how you feel. Give him directions and make sure he follows them. If you tell him to go slower...  He must do it!  If you say that it hurts... He must stop!

If you see that you can handle his finger, you may be able to handle his penis; but, if you can’t even handle his finger, you won’t be able to handle his penis, so it’s better for you guys to stop and try some other time.

Finger stimulation on your anus is a very important pre-anal sex, don’t let him skip this step! Never let him stick his penis in there right away.... Remember, this is not a vagina!... He needs to work it out gradually.

6. He must go in very very very slow.... And gentle!

After he has stimulated your anus with his finger for a while, you should be ready for his penis. If this is your first time for anal sex, using a small anal sex toy, instead of, or before his penis could be a great way to gradually get you used to the new sensation of having something going in there.

Either you guys choose to try a small anal sex toy first, or you choose to go directly with his penis, do it very, very, very slowly and gently. Ask him to stop if you need to, and tell him to go slower anytime you want.

This is a very delicate moment, he needs to be extremely careful to not hurt you. Make sure he uses lots of lube, take his time, give you lots of time too, and follow your guidance.

So, once you’re ready for him to insert his penis, and he has applied lots of lube in your anus and his penis... Relax by taking deep breaths, and try to open your anus by pushing your anal muscles outward to facilitate the penetration.

Now, he should press his penis against your anus, applying pressure. He must slowly start sliding only the tip of his penis and stay still to give you time to get used to the sensation of having something bigger going in there.

He will feel the ring of your muscles around the anus tighten and relax. At this moment, he should not move his penis just let the muscles work.

When the muscles relax, he has two options, he can either remove his penis and gradually insert it again going a little bit deeper this time, or if you can handle it, he can keep his penis inside, and just insert it a little bit further and further as far as you can handle it.

This choice will basically depend on what you feel is the best for you. You may want him to remove his penis and relax to try again, or you may want him to keep going.

Actually, the most uncomfortable part for you would be the initial penetration; so, once the tip of his penis is already in there, it would probably be better for you if he keeps going on, so you don’t have to feel the discomfort of the initial penetration again.

Therefore, if you can handle it, let him keep the penis inside, and just have him to stop to take a break, and then let him keep going in very slowly. Tell him to stop every time you need to. Let him know if you prefer him to take his penis out.

Once his penis is already inside, tell him which pace of thrusting feels comfortable for you. Tell him to go very slowly and gently, until you say you can handle a little bit more.

Anal sex can be very pleasurable or very painful; it all depends on how gentle he performs it. And depending on how gentle he is, you will like it or hate it.

Make sure he’s willing to have lots of patience and take his time!... No matter how much aroused he is, never let him thrust you too hard or too fast because he can hurt you.

7. Keep it clean and safe

Remember, never let him switch from your anus to your vagina because he could spread bacteria and give you a vaginal infection.

If he’s using a condom (which he should do) make sure he replaces it with a new one before going to your vagina, and if he’s not using a condom, he must wash his penis thoroughly with water and soap before entering your vagina. Same goes for the fingers, mouth and toys!


As you can see by these 7 things on how to enjoy anal sex, this sexual practice requires of certain precautions that he must take for you to feel pleasure instead of pain. However, you must be as well-informed as him, for you to know if what he’s doing is right or wrong.

For that reason, I recommend you and your partner to read Anal Pleasure For Her.

This is a very complete guide that will explain you guys exactly what to do to perform this sexual activity in the RIGHT way, so you can feel pleasure instead of pain. From precautions and recommendations, to tips and techniques to achieve anal orgasms, you'll find ALL the information you both need to explore anal pleasure.

Although the guide is directed to men, I highly recommend you to read it as well. Do not have anal sex with “blind eyes”. It is your body! You must make sure you're not getting hurt.

Then, after he reads the guide and when you feel you can trust your partner enough to know that he will be very gentle and careful, go ahead and enjoy the pleasurable world of anal sex.

Remember, it may be uncomfortable at the beginning, but if done properly, with time and practice, your body will get used to, and you will start feeling it pleasurable.

Just DO NOT tolerate pain! If it hurts, something it’s being done wrong!

Angie :)

Connecting you with the best love and sex advice for a healthy relationship!

Next: How To Achieve An Anal Sex Orgasm

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