47 Tips for First Time Anal Sex — The Expert Guide for Beginners

47 Tips for First Time Anal Sex — The Expert Guide for Beginners

It’s no secret that when people think about anal sex, they often immediately think about pain. This doesn’t have to be the case. In fact, most people don’t even realize that there is such a thing as pleasurable anal intercourse. After all, we’ve become so used to thinking about the negative aspects of anal sex that we forget what’s possible. Here are some tips and techniques, for both the receiver and giver, guaranteed to help make your first-time more enjoyable.

Table of Contents

Don't Worry; It's Not Dirty

Many people are hesitant to try anal because they think it will be dirty or excruciatingly painful, and neither should be the case with adequate preparation. 

When you have anal sex for the first time, slip-ups might happen. However, you won’t be swimming in a brown lake. Anal is not a dirty sex act, as some people imagine, which is why countless couples regularly do it. 

Don't Worry; It Should Not Hurt

As a part of your mental preparation, remove the thought anal sex is painful. 

Anal play should never be painful once you relax, pour enough lube, and start at a slow and gentle pace. Thoughts of it being painful are the key reason why so many people that would actually enjoy it are hesitant to ever try. 

Your first-time anal experience might feel strange because of the new sensations. It might even be a little uncomfortable because most people aren’t used to the feeling of a large object entering, not exiting, their anal canal. Once you get used to the feeling, remember to breathe, and relax, the uneasiness will subside. You might even discover that it feels better than you imagined it would. 

Don't Believe That It's Wrong to Want Anal

The third most common hindrance to anal sex is thinking that it is too taboo or wrong to try it. For many heterosexual couples, the thought of trying anal sex doesn’t cross their mind too often. It’s easy to see why when you have plenty of other fun and pleasurable parts to explore. 

But wanting anal sex, as a heterosexual couple, is not wrong or even taboo! In fact, it’s something that both the receiving and giving partners can enjoy. If you’re a man, you can experiment with anal sex by asking your female partner to stimulate you with her finger or a toy. Not so deep inside is the prostate gland, and when stimulated, it gives a unique and highly pleasurable sensation. A female partner, likewise, can receive a lot of pleasure from having her partner penetrate or stimulate her anally. Although she does not have a prostate gland, she can feel the pressure against her vaginal canal or simply enjoy stimulating the thousands of nerve endings around the anal opening.

Try Going Solo First

If you’re a little apprehensive about trying anal sex with your partner, you might be better off doing it by yourself and seeing how you feel. You don’t need to go and purchase sex toys just yet, although that would help. Start by slowly and gently teasing your anus with your finger. Swirl your finger around the opening of your anus, covered with lube. 

Be patient and slow; insert just the tip inside. Move your finger a little to play with the different sensations, and put your finger a little deeper inside when you’re ready. The great thing about going solo first is that you don’t feel pressured to perform or go through with it if you aren’t comfortable. 

Finally, after playing with your fingers, get your new sex toys fresh from their boxes and see how they feel. We recommend a vibrating butt plug or anal training kit for first-time anal lovers. The anal training kit gives butt plugs various sizes to help you become more accustomed to fitting larger objects inside. Whereas the vibrating small butt plug, is purely for pleasure.

Focus on Communication

To enjoy your first anal sex experience, you should communicate with your partner about what you need to feel safe and relaxed. This includes making sure that they understand what you expect from them, as well as asking questions about their own expectations. If you’re nervous about anal sex, don’t worry; just ask! The more open communication you have about anal sex beforehand, the easier it will be to relax and enjoy yourself. And remember: no one ever said anal sex has to be painful!

Make Sure They Know Their Limits

Anal sex isn’t always easy, especially during the beginning stages. Make sure you let your partner know how much you can handle before trying anything new.

For your first time, don’t push yourself too far past your comfort zone.

Don't Think It Will Be Like Porn

Anal sex will not be like porn. Unlike porn, where you skip straight to the good, deep penetration, you don’t get to skip the preparation in real life. Attempting to shove a penis into the rectum without foreplay, lubricant, or slow and gentle stretching will just lead to pain, bleeding, and a sore ass the next day.

Prepare for Anal Sex

If you’re going to try anal sex for the first time, you should definitely plan ahead.

This means getting ready in advance by purchasing ample lubricant. It also helps to take your time to prepare yourself, which can mean waiting for an appropriate moment (like after you’ve had a shower and your morning bowel movement) or planning ahead to avoid awkward moments later.

You may also want to consider wearing something sexy or decorating the room with candles and sensual music before you start. 

Eat Enough Fiber

Before having anal sex for the first time, focus on checking your diet and digestive health. It will put you on a regular bowel movement schedule and prevent accidental slip-ups while enjoying anal sex.

A diet rich in fiber will help your digestive health greatly by making your bowel movements regular and come out in large pieces, as opposed to tiny clumps.

Don't Do Anal, If You Have a Stomach Bug

 If you have had a bad stomach lately, it might be better to save anal for a better time. You are very likely to have an accident during sex if you have been experiencing diarrhea and runny stool for the past few days. Even if you think you cleared everything out, it’s recommended that you wait at least a day or two to see if, indeed, the stomach bug is gone and you are back to normal. 

Wash Before Anal Sex

Start with a clean behind before any anal stimulation. Plus, it gives you and your partner an excuse to have playtime in the shower. Wash your cheeks and anus with warm water and soap, and finish by drying with a towel. Contrary to popular belief, you don’t need to douche before anal play, and it actually could be more harmful than helpful.

Be Careful With Douches and Enemas

You don’t need to douche or have an enema before anal sex. Before you run out and purchase your first anal douching kit, consider whether or not it’s the right choice.

Most of the time, you will not need to douche or use an enema. If your diet is relatively healthy and you have regular bowel movements, all the fecal matter in your rectum should have exited your body in one piece earlier in the day. A douche or enema, in that case, would be a waste of time. 

Another scenario that could happen is that your fecal matter does not come out in one piece and is further up in the rectum. Spraying the fluid into the anal canal causes the higher-up feces to loosen or break apart into tiny pieces. You might get a few of those pieces out before sex, but there is a chance that you did not.

Put a Towel Down

Before getting to business, put a dark-colored towel on the bed where your partner will lie during sex. The towel serves multiple purposes. It will make clean-up easy if an accident occurs and saves you from doing a midnight run to the laundry mat, and it gives you something to wipe all the excess lube off on later. 

Don't Use a White Towel to Clean Up

If every towel you own is white, it would be best to purchase one high-quality dark towel as part of the preparation stage.

White towels clean just as well as dark ones, sure. But a white towel won’t save your partner from embarrassment like a dark one will! 

It’s not likely that (if you prepared well) an accidental slip-up will happen, but you can never be 100% sure. If something were to slip out, quickly dispose of it while concealing it in the dark towel. It might sound like a slight difference, but your partner might hesitate to try anal again if, on their first time, they’re humiliated beyond belief by having to look at a poop stain on a bright, white towel.

If Your Partner Gets Shit On You, Don't Mention It

As a gentleman, you shouldn’t aim to embarrass your partner during intercourse. When doing butt-stuff, things happen occasionally. If your partner does have an accident, dispose of it and clean up with a dark towel without mentioning it. Your partner should not know if a massive turd slipped out or if it was only a tiny brown dot. 

If possible, be discreet about it. For example, wait until after sex, say, “I’ll get us a fresh towel,” and remove it before they have time to notice why you’re in such a rush to get those fresh towels.

Don't Forget To Practice Safe Sex

Even though anal sex doesn’t usually transmit sexually transmitted infections, risks are still involved. Fortunately, there are steps you can take to minimize these risks. These include practicing safer anal sex by using condoms, even if you think you or your partner is clean.

Use Foreplay

Don’t jump into anal play; warm up your partner with foreplay beforehand. There are a lot of excellent foreplay techniques that you can utilize to make your partner soaking wet, aroused, and craving sex. Did we also mention that being more aroused makes your partner more likely to orgasm? 

Ideally, foreplay would start before you take your clothes off and get ready for sex. It’s the moments when you allow your fingers to linger on your partner’s body, kiss them passionately, massage their body, or whisper how badly you crave them into their ear. 

When you get their clothes off, start with giving them a rim job, playing with their anus by tracing your finger around it, or massaging their body before anal sex.

Use Lube

Using plenty of lube will allow you to move around easily without worrying about hurting your partner. The anal canal does not naturally lubricate itself, so using lubrication is not optional. A water-based lube is a safe and reliable all-around option.

Avoid Numbing Agents

Numbing lubrications reduce the pain associated with first-time anal sex or anal play, in general, when the person is not fully relaxed and prepared. Although numbing agents sound like a great idea, in theory, they might actually be more harmful than good.

Pain is a natural response when something is wrong with the body. For example, when you stick your hand on a hot stove, you don’t let it burn to a crisp before taking it off. Likewise, pain during sex can signal that something is very wrong, and you should either slow down or stop completely until you figure out what the cause is.

Numbing agents take away the pain and prevent you from realizing you need to slow down or stop what you are doing.

Get In the Right Headspace

Anal sex requires a certain mindset. You need to be relaxed, comfortable, and willing to try new things. You may feel nervous or scared, but this is normal. The best way to relax is to focus on what you want to do, communicate with your partner, and then utilize relaxation techniques. 

Don’t worry about disappointing your partner if you want to pass on anal tonight and try it a different day, week, or even month. If they’re a good partner, they will understand and be willing to wait for you to be ready for this experience. 

Position Yourself Correctly

There are many different ways to do this, but the best way to find out what works for you is to experiment.

Many people suggest starting with missionary because it provides a lot of direct stimulation to the prostate gland (in men) and is an easy position for first-time female partners.

You might want to try spooning, doggy style, or triceratops once you become more comfortable with anal sex. Sex wedge cushions are also great options. Try to vary your positions as much as possible to avoid getting bored and get the most out of anal sex.

Don't Forget Your Partner's Needs

Anal sex is one of those things where both parties need to feel satisfied. You should never forget to pay attention to your partner’s needs. This includes making sure they’re comfortable, have enough space, and that they’re able to enjoy themselves.

If you’re worried about hurting your partner, ask them if they’re okay and check in regularly. If you’re having trouble finding a position that feels right, talk to your partner about it. Ask them if there’s anything they’d like you to try.

Remember to Relax

The most common reason people don’t enjoy anal sex is that they’re too tense. Try relaxing your muscles and breathing deeply. This helps you relax and allows you to focus on receiving pleasure from your partner. If you feel like you need some extra help, consider trying a few relaxation exercises and massages.

Remember to Breathe

When you find yourself tensing up, take a deep breath. Breathe in through your nose and out of your mouth. Throughout anal sex, as your partner is going deeper inside your rectum, remember to keep breathing and avoid accidentally holding your breath.

Start Slow

Attempting to go in fast and hard will do nothing but cause pain to the receiving partner. When it’s the first time, it is always better to start slower than usual and slowly work your way up to a faster pace. Going slower also benefits both the receiver and giver as it gives both more time to listen to their body and pause when they note something is wrong. 

Take Your Time

Those who have been performing anal intercourse for years have more relaxed sphincter muscles, making anal penetration easier and less painful for them. But for beginners, it takes practice to learn how to fully relax your muscles and body. Take your time and enjoy the process.

Start With Rimming

Rimming is when your partner licks, sucks, and/or nibbles his or her tongue along the rim of your anus. It’s also called “rimming” or “tongue-fucking.” While it may seem like something only kinky people would enjoy doing, rimming actually has some benefits. Stimulating the nerve endings on the surface of your skin can help loosen up your muscles so you can have more pleasure during sex.

Start With a Booty Massage

A booty massage gets your partner aroused and relaxed before anal sex. Massages are great for getting those sphicter muscles and muscles throughout the body to relax and calm down. 

Start by applying massage oil or coconut oil to your partner’s backside while they lie on their stomach on the bed. Start at their mid-back and work downwards. Rub their middle and lower back in a circular motion, then proceed down to the butt. Rub each cheek in a circular or up-and-down motion. Periodically give each cheek a small squeeze too. Watch your partner’s body language and listen for moaning. Do they sound and look like they’re enjoying it? Good! Keep it up for a while before asking them to lie on their back, and spread their legs for anal sex.

Use Your Fingers

If you are new to anal sex, you should start out with your fingers first. Start small, so you don’t hurt yourself or cause any damage to your partner’s anus. 

Don’t forget that your goal isn’t just to get it over with as fast as possible. It takes some practice to learn what works best for you. Start slowly with a finger, then move up to two fingers, then three, etc.

Use A Dildo

A dildo is a realistic toy explicitly designed for pleasure. Because they’re shaped like real penises, they offer a closer approximation of actual human anatomy than other toys. They come in many shapes, sizes, colors, and textures, which will provide you with plenty of options if you’d prefer something else.

First, Try an Anal Training Kit

An anal training kit is a perfect starter for newbies to anal sex who might want to start with something a little more gentle and easy. The kit contains butt plugs of various sizes, so you can work your way up from finger-sized to 6-inch-penis-size if you want. 

Use Toys

Aside from anal training kits, great starter toys include vibrating butt plugs, inflatable butt plugs, and anal beads. There are many reasons why you might want to start with anal toys before anal sex. The toys come in much smaller sizes and can be easily adjusted. There’s no pressure to finish to give your partner pleasure, and you can easily remove the toy and grab a bigger one once you’re comfortable.

Try Clitoral Stimulation

Anal penetration feels excellent, but don’t forget about the pleasure epicenter — the clitoris. While using a toy, finger, or penis for anal play, you or your partner should reach down and stimulate their clit at the same time. Be sure to get it wet with your partner’s natural lubricant or water-based lube, and slowly stroke the clit. Keep the same rhythm and pace once you find something your partner enjoys.

Don't Put It All In At First

When trying anal sex for the first time, it’s tempting to want to get the entire length of your penis inside your partner. Congratulations, if on your first time, you can make that happen. But don’t feel defeated if it doesn’t. 

The goal of your first time having anal sex should not be to get it all in or go very fast. You are more likely to get hurt when rushing than actually enjoying the experience. Start slowly, and go as deep as you can the first time. Next round, see if you can go a little deeper.

Stick It In, Hold

When you first get the tip inside the anal canal, hold for a few seconds. There are two powerful sphincter muscles you must get past if you want to enjoy anal sex. Slowly go inside and wait for a few seconds for your partner’s body to continue to relax and for you to get pulled slightly deeper inside. As long as your partner doesn’t feel pain, continue at a slow and gentle pace until the full length of your penis is inside.

Don't Panic or Tense Up

You might accidentally clench your butt cheeks close together the first time and tense your muscles. There are two very powerful sphincter muscles inside the rectum, and both have to relax if you want pleasurable anal penetration. 

Once you find yourself tensing up and starting to panic from all the strange sensations, tell your partner to pause and wait. Breathe deeply and relax your mind. Continue to breathe in through your nose and out through your mouth. When you feel relaxed and ready, tell your partner to start again.

It Might Feel Strange at First

The first time you have anal sex, it might feel strange. The sensation is different from vaginal and oral sex. The anal canal is typically an exit, not an entrance, so the first time you experiment with anal play, you will feel your sphincter muscles relax and your anus stretch. 

If the sensation feels too weird, pause for a moment without going any deeper inside the rectum. Whereas, if you feel pain, it’s probably best to stop, apply more lubrication, go slower, and try again.

Anal Queefs Are Real

While thrusting in and out of the rectum, air can get trapped inside. Most people have heard of queefs. They sometimes occur during vaginal sex when one partner is thrusting, and it causes a unique sound to come from the vagina. It’s just air! Nothing terrible is happening, but it can be slightly embarrassing the first time you hear the sound. You might also be a little confused if you did not know that queefs can happen inside the anus too. Don’t worry. The queef will pass, and you can continue enjoying anal. 

You Might Need More Lube

While having sex, you might need to pause, grab the bottle of lube, and apply more. This is something you never see in porn, so a lot of people forget their first time until they learn differently. Save yourself the trouble and keep the bottle of lubrication nearby, preferably somewhere you can grab it without having to readjust your positioning too much as much control yourself.

For Something Thicker, Try Silicone or Oil-Based Lube

Be aware every lubrication has its pros and cons. For example, water-based lubricant tends to dry out easier than the other types but is condom and vagina safe. Silicone is a bit more heavy-duty and won’t dry out as easily, but it doesn’t mix well with silicone sex toys or vaginal penetration. Lastly, the oil-based lube tends to stain the sheets and is not suitable for vaginal or sex toy using, and has been shown to degrade condoms.

It's Okay If You Shit Yourself

A healthy diet and good timing will prevent most accidents, but not 100% of them. If something slips out, it’s not the end of the world. Hopefully, you read the previous anal sex tip where we recommend putting a towel down before anal play. Use the towel to quickly get rid of whatever might have slipped out, grab a fresh one, and, as long as it wasn’t a mood-killer, get back to having sex. 

You Might Bleed a Little

Small amounts of blood are not necessarily an alarm bell. You might bleed from minor anal tears inside the rectum, especially when it’s your first time. If you happen to see small red dots of blood, don’t panic. It’s probably okay. Large amounts of blood, on the other hand, is a red flag, and so is pain.

Stop If It Hurts

There’s no reason why you have to have anal sex. When something is going wrong, and it’s painful, just stop. You can wait a few moments, talk about it, apply more lube, change position, and try again. Having anal sex for the first time is a slow process that might take a lot of trial and error to find what specifically works for you.

Respect How You Feel

Don’t ignore your body because you feel you have to have anal sex. If you feel like things are moving too fast, tell your partner to slow down. If you’re experiencing pain, stop, apply more lube, and try again. Respect the messages that your body is sending you. Doing so will avoid accidental tears and pain later on.

Give It Three Attempts Before You Give Up

This is going to take some practice. Don’t expect to master anal sex in just one session. Take your time and make sure you’re doing everything safely.

It’s also important to remember that everyone has different preferences. Some people love anal sex, while others hate it. So, if you’re new to anal sex, you might want to try it a few times before deciding whether or not you like it.

You might not like anal sex your first time. In fact, most women don’t. It does not mean that anal sex is bad or that it’s just not for you. The reason why a lot of people don’t enjoy their first-time having anal sex is that it’s rushed, there was not enough lubricant, or the sphincter muscle was not fully relaxed. 

A shitty first time doesn’t mean you won’t love it on the second or third try. Before tossing in the towel forever, give it a good three tries with proper anal penetration techniques. If you don’t love it or it’s just so-so by the third try, then perhaps anal sex isn’t for you.

Never Go Ass to Vagina.

Be mindful of what you are doing and where you are putting your fingers and penis. The anal canal has a unique bacterial environment that you do not want to introduce to the vagina. Doing so could lead to bad, itchy, smelly vaginal infections. 

The proper way to go from anal to vaginal sex is to take off your condom and replace it with another one, then have vaginal sex. Never use the same condom!

If you did not use a condom, wash off in the shower or in the sink (if it was just your fingers) and then move on to vaginal sex.

Watch Where Your Cum Goes

You can’t get pregnant from anal sex as no magical passageway leads from the rectum to the fallopian tubes, where the egg is awaiting a sperm to fertilize it. However, anal sex can lead to accidental pregnancies when semen slips out of the anus and runs down into the vagina. 

If your partner is ovulating, even a tiny bit of semen can lead to an accidental pregnancy. Protect yourself by having a plan for where your semen will go and quickly catch it if some does slip out and start running towards her vagina.


Your first anal sex experience does not have to be painful, awkward, or any other negative emotion that you conjured in your mind. Most people who go at a snail’s pace, starting with fingers or sex toys, are able to receive a lot of sexual pleasure from anal.

If you felt mild discomfort your first time, use better techniques and give it at least two more attempts to determine if anal is for you are not.

With these 40+ techniques, you should have a better experience inside the bedroom.

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