We’ve all heard the rumours that anal sex is painful, which sounds downright scary!

But what if I told you that exploring this new territory does not have to involve any discomfort?

Today, I’m going to give you the information you need to ensure a pleasurable, pain-free anal experience.

Like anything else, there’s a right way and a wrong way to have anal sex.

The wrong way can cause some discomfort, while the right way feels amazing.

So let me show you the path to pleasure not pain.

Why Try Anal?

Before we get into how to make it amazing, let’s look into some benefits of trying anal sex:

As an alternative: There are a number of reasons why vaginal sex may be unavailable, from being on your period to having a yeast infection. Anal still allows you to have sex without any vaginal penetration during these times.

For the adventure: Anal sex is an adventurous step for many couples and can be a great way to bond with your partner. You’ll get to explore new sensations and territory together, and the kinkiness of the act is a big turn-on!

Low pregnancy risk: Although it’s not completely impossible to get pregnant from anal, odds are extremely low. If you want to have some intimate fun without worrying about pregnancy, you can stick to butt stuff with your partner.

Does Anal Sex Hurt?

The commonly accepted idea is that anal sex hurts at first and then eventually becomes enjoyable.

But that isn’t true for everyone:

To put it bluntly, it will only hurt if you don’t do it right.

Here’s the deal:

While anal sex is not always comfortable, neither is regular sex.

Like ordinary intercourse, pleasurable anal requires foreplay.

But in this case, you’ll want to take it much slower.

Think about how much time you put into regular foreplay and multiply that by 10.

That should give you a clearer idea of how slowly to take anal exploration, at first.

I can’t drive this point home enough:

Successful butt sex depends almost entirely on proper preparation.

Preparation includes getting into a relaxed state of mind. Since the anus is a sphincter, being calm is a must for smooth penetration.

Some people can have a hard time relaxing before their first anal penetration experience. This can be from having a painful experience in the past, or simply fearing the worst.

As long as you and your partner are both paying attention, communicating, and taking your time, you shouldn’t experience pain.

You can also review my full anal hygiene preparation guide here.

How to Have a Pain-Free Anal Experience

Now that you know it’s up to you and your partner to make your experience a good one, and that pain isn’t inevitable, you’re ready to learn how to make anal great.

Now:

The first step to having a pain-free anal experience is patience. You’re doing something new and taking it slow is the best way to avoid mishaps.

You wouldn’t jump right into learning a new sport without warming up your muscles or teaching yourself the proper movements to prevent injury, right?

Well, this is kind of like that.

Here are some guidelines to help you have a great time with your first butt sex experience:

Listen to Your Body

People enjoy anal sex all the time without pain and discomfort, and they achieve this by listening to their body.

They only do what feels right and stop if something feels off or causes discomfort.

And as long as you follow the rest of the guidelines I’m about to give you, it really is as simple as that.

Use Enough Lube

You can’t have a successful anal experience without lube.

Skipping this step is just asking for trouble.

The anus isn’t self-lubricating like the vagina, which means that adding lubrication is up to you. You’ll want to add plenty to the anus and your partner will need to apply a lot to his penis, as well.

Below, I’ll cover a couple of different indications that you should use more lubricant:

Too much friction: If you ever notice a rough or stinging sensation while attempting anal penetration (with a penis, finger, or toy), pause and add more lube.

This type of feeling is a key indication that there’s too much friction going on in the backdoor area. So if you feel it, make sure you speak up!

Sex is never something you should “endure.” It’s supposed to feel good, so don’t hesitate to let your partner know if there’s not enough lubrication and you need more.

Trying to push through the discomfort is only risking further discomfort and potentially even damage.

Muscle tightness: Another signal that you need to slow down and add more lube is a tight feeling in your muscles, like your anus doesn’t want to relax.

You might even be adding more lube and still experiencing more pressure than is comfortable. This could mean you need more foreplay, or more time to get mentally relaxed.

Again, if you feel this, the best course of action is to pause what you’re doing and backtrack. Use a smaller toy or have your partner switch to anal fingering to warm you up more.

Again, never tolerate any discomfort or pain.

Doing so will only add to increase your discomfort and potentially even ruin your perception of anal sex.

Choose the Right Lubricant

You’ll find sources that claim that silicone or oil-based lubricant is the only way to go with anal.

You’ll also find people swearing by water-based lube products.

So which is it?

Here’s the bottom line:

Using lube that’s specifically designed for anal is more important than whether you use water, silicone, or oil-based product.

Why?

Because anal sex lubricant tends to have a thicker consistency, which helps it last longer. Again, the anus doesn’t self-lubricate.

That means that you’ll have to pause a reapply lube a lot if you the type you’re using has a thin consistency.

Look for lube specifically for anal, ideally with a gel consistency, which will usually mean a water-based product.

Water-based lubes have the benefit of being compatible with most sex toys, so that’s worth remembering. Silicone or oil-based lubricants may be incompatible with condoms or adult toys.

Always check compatibility before using lube.

You may come across numbing lubricants in your search for the perfect product. While some claim that these products can reduce discomfort, remember that discomfort is a sign to slow down.

Numbing the area means you won’t notice these signals and may keep going even when it’s a better idea to slow down.

I personally don’t recommend numbing products, but they’re popular in many online sex product stores. Use the at your own discretion and, if you have any doubts, do further research before deciding.

Take Your Time Getting Relaxed

Relaxation is just as important as lubrication and, without it, anal sex won’t work right.

The rumours you’ve heard about anal sex hurting come from over-eager people who skipped this key step.

Your anus has a ring of muscle inside it (the sphincter) that keeps the opening closed when it’s not “in use.” Unlike other muscles, this one doesn’t release immediately and works much more slowly.

As a result, you can’t jump right into putting anything up the anus because the sphincter must loosen up enough to allow entry.

Trying to force the sphincter to open before it’s good and ready will result in discomfort and potentially even pain.

4 Ways to Relax the Sphincter Muscle for Pleasurable Anal

As mentioned, a key component to successful butt play is relaxing your sphincter muscle enough penetration.

So how do you do that?

1. Practice Relaxation Techniques

If you’re constantly tense or stressed from day-to-day life, you might find it helpful to practice some relaxation techniques.

Meditation, yoga, or even taking more deep breaths can all help you learn to control your muscles and relax at will.

Practice lying in bed and completely loosening all of your muscles as you breathe deeply. Get familiar with that sensation in your own time, and you’ll be on your way to pleasurable, mind-blowing anal sex.

Once you’ve done this, you’ll be ready to…

2. Experiment by Yourself

If you want to try anal penetration with a partner but you’ve never had anything up your butt before, it’s best to experiment alone, first.

That way, you can get used to the sensation before you share it with another person.

You’ll also have an idea of how long it takes your sphincter to warm up and allow things to pass through it.

A beginner butt plug can be a fun way to experiment with this during masturbation.

Anal beads are another fun way to test the waters of backdoor penetration before moving onto full-on butt sex.

While toys are always an option, perhaps you’ll be more comfortable using your finger. That’s totally fine.

Whatever the case, don’t forget the lube and if you do use toys, check to make sure your lubricant is compatible with it. Doing so will prevent you from causing damage to your toy.

3. Progress to Your Partner’s Finger

So you’ve played around with your anus a few times on your own and you’re familiar with what feels good and how to relax the muscles.

That’s great news!

Now it’s time to let your partner try penetrating you with their finger. Have them apply plenty of lube to your anus as well as their finger before you begin.

Next, relax as much as you can as your partner slides their finger into you very gradually. Communicate constantly and, most importantly, ask them to take their time.

Here’s the deal:

Rushing this step will do neither of you any favors and may even result in a frustrating situation where your sphincter refuses to relax.

Even if your anal play session doesn’t go exactly as you hoped, taking it slowly is more important than fulfilling your original expectations.

Remember to listen to your body, and pause as often as possible to get comfortable and relax deeper.

As your partner gets deeper with their finger, it should begin to loosen up and feel more comfortable.

If it doesn’t, they can pause what they’re doing while keeping their finger inside. This can give you a chance to relax more deeply.

Then you can try having them push their finger further into you at a comfortable pace.

Also remember:

Your partner pulling their finger out too fast can cause some pain or discomfort, so this must be done slowly, as well.

4. Adding a Second Finger

Once you’re comfortable with your partner’s full finger inside you, have them try moving it slowly in and out.

For pain-free anal play, the one receiving penetration should always decide the pace, at first.

Be communicative and let them know if you need them to go slower, add more lube, or take a break.

As soon as you can comfortably handle the thrusting motion with one finger, you can progress to adding a second, then third finger.

After that, as long as everything feels okay, you’re ready to move onto the main event:

Anal sex.

The Best Anal Sex Position for a Pleasurable Experience

Having a pleasurable anal sex experience depends entirely on you, as the one receiving penetration, setting a comfortable pace.

That means that the most successful anal sex positions will put the receiver in full control of the speed and the penetration itself.

Whether the one being penetrated is on top or bottom is simply a matter of preference.

Either position can put the receiver in control, so you have some freedom of choice here. I’ll give you a rundown of both options below.

Receiver on Top

One option for a comfortable beginner anal sex position is starting out with the man on his back. This allows you to control how deep inside you want him to be.

Instruct your partner to lie back and stay still. Add some lube to his penis and to your anal area, then get in the cowgirl position facing him with your knees on either side of his body.

Gently guide him to the entry of your anus and relax your muscles as much as possible. You may find it helpful to “push” a bit as you would when you’re having a bowel movement.

This can encourage your muscles to relax enough to allow entry. Once again, if you experience any discomfort or hesitation whatsoever, pause to take a break.

As soon as your sphincter has relaxed enough to take the tip of your partner’s penis, it’s time to lower yourself onto him slowly.

Take it millimeter by millimeter (rather than inch by inch). As soon as he’s completely inside you, you can begin moving up and down.

Your partner should remain still and patient throughout this experience. It’s very important that you set the pace yourself to ensure full relaxation.

As soon as you’re comfortable with it, your man can begin adding gentle thrusting motions.

Receiver on Bottom

Alternatively, you can start out receiving anal penetration on bottom. I recommend lying on your stomach to start.

In this position, you don’t have to tense any of your muscles to support your body, which encourages fuller relaxation.

Have your partner position himself behind you with the tip of his penis against the entry to your anus.

Place your hands flat down on the bed on both sides of your body to give yourself some leverage. Then you can begin pushing your butt back to receive the tip of his penis.

As soon as it feels comfortable to you, use your hands to move your body back and forth.

Don’t forget to add more lube or take breaks as necessary!

Aftercare

As soon as you’re finished with your first butt sex experience, you may want to lie back, relax, or cuddle with your partner a bit.

Depending on how intense the thrusting motions were during your penetration experience, your anal muscles might need a break.

After resting a bit, you can take a shower to rinse off the lube. If you feel any irritation around the anal area, you can apply some coconut oil to it. Avoid products with harsh chemicals for this.

Irritation is a key indication that you should’ve used more lube, so keep that in mind for next time.

Don’t Forget to Communicate!

Whether anal sex is new to you, your partner, or both of you, communication is essential.

Now:

Your partner may have been a bit over-zealous with thrusting and caused some discomfort. Or perhaps you got carried away and didn’t use enough lube.

Maybe you could’ve used some more foreplay, or you had an ideal anal experience.

Whatever the case, you need to express these realities to your partner. Some men don’t understand the importance of relaxation in receiving anal.

And your partner won’t know, unless you speak up!

You may even want to have him read this article so he understands how to make the experience comfortable and pleasurable for you.

While you can indirectly communicate your wants and needs, direction communication is best. That way, you don’t have to guess what each other is thinking.

Make sure you also ask your partner for his take on what went well and what could be improved next time. This advice applies not only to anal but all types of sex.

After trying it, you may learn that you don’t enjoy anal very much. That’s totally okay!

People are different and there’s no reason to feel apologetic about not being into a certain sexual activity.

Anal Sex Does Not Have to Hurt

As you can see, there’s no reason why anal sex has to hurt or feel uncomfortable.

As long as you use plenty of lube, practice on your own first, and take it very slowly, you’ll be fine.

Anal requires more warm-up and planning than vaginal sex. But following the guidelines for proper preparation in this article will ensure that you both have a smooth experience.

Before you know it, anal may become a regular part of your pleasure repertoire.


Jessica Winter
Jessica Winter

Hey I'm Jessica! Thanks so much for reading my work. I've been studying the Sex Therapy industry for years, and my absolute passion is helping men and women improve their sex lives! I really hope my work here is helpful, and I will continue to do my best at providing value for you!