How To Prepare For Anal Sex: The Comprehensive Guide

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If you are curious about how to prepare for anal sex, you’ve come to the perfect place!

This easy-to-follow guide will show you exactly how to prepare for anal sex – emotionally and physically. If you haven’t ventured south before, anal sex can seem daunting but it definitely shouldn’t be! We’ll explain everything you need to know about preparing for anal sex and teach you how to make it fun, clean and orgasmic!

With the right preparation, anal sex can feel amazing, but not everyone knows what to do. There are dozens of myths and misconceptions about what you should and shouldn’t do prior to having anal sex. The goal of this guide is to help you cut through the confusion, separate fact from fiction, and prepare yourself for anal sex the right way!

This guide will teach you exactly how to:

  • Prepare your mind and body for anal sex
  • Make anal sex safe, hygienic and pain-free!
  • Experience stronger and harder orgasms than ever before!

If you’re ready to enter the world of bliss-based anal education, keep reading…

And remember to check out my new course – Squirting Triggers 2.0 – where we reveal, step by step, how to become incredible in bed. You’ll be a certified sex god. Check it out further down this article.

As anal sex carries inherent risks, please read our disclaimer:

This guide is strictly for information and entertainment purposes only. SchoolofSquirt.com does not endorse any of the activities or practices discussed herein. All opinions expressed are those of the writer and have not been written or reviewed by a physician or healthcare professional.

Sound fair?

Then let’s get started!

Learn about your body

The best way to begin to prepare for anal sex is to educate yourself about the realities of anal intercourse. Anal sex is a practice that’s surrounded by so much misinformation that you need to prepare yourself psychologically before you begin touching yourself physically. By learning how your body works, you’ll know what to expect when you start to explore and this will make the experience of preparing for anal sex FAR more enjoyable!

Regardless of gender or sexual orientation, everyone’s anal anatomy is roughly identical so that’s the most logical area to learn about first.

One of the reasons why anal sex feels so good is that the opening of the anal canal – the anus – is literally packed full of sensitive nerve endings. The anus and the first few inches of the anal canal are made from the same smooth tissue and are especially sensitive to vibration and touch.

A few inches along the anal canal lies the Dentate line and beyond that is the rectum. The rectum is around eight or nine inches long and contains far fewer nerve endings than the anus or anal canal.

If you want to prepare for anal sex, you should have a basic understanding of the two main muscles in the anal area – the internal sphincter and the external sphincter.

The inner surface of the anal canal is actually part of the internal sphincter. This muscle is controlled by the central nervous system and isn’t under voluntary control. In other words, you can’t make this muscle relax. If you rush into anal sex without warming up, you may injure your internal sphincter, sometimes permanently.

Your internal sphincter is surrounded by a layer of striated muscle called the external sphincter. This is a voluntary muscle so you can learn to relax it, but this takes time (and practice!) – don’t worry; we’ll show you exactly how to do this later on in this guide!

3 anal sex myths that you probably believe

As a taboo sexual practice, anal sex is shrouded in mystery and is the subject of a number of myths. We’ll address the three most common anal sex myths head-on and cut through the misconceptions to bring you the facts. If you want to prepare for anal sex, here’s what you need to know:

Myth 1. Anal sex is messy

If you’ve heard horror stories about anal sex being messy then rest assured that poop is stored in the upper bowels – not the anal canal. No finger, sex toy or penis is big enough to reach far enough inside to encounter stored poop. Although some couples report experiencing small amounts of fecal matter during anal intercourse, you can avoid this by cleaning the anal canal with a douche beforehand.  You’ll learn exactly how to do that later in this guide!

Myth 2. Anal sex is always painful

The second pervasive myth that puts many people off trying anal sex is the idea that anal sex is always painful. Some people even believe that anal sex causes permanent damage or leads to incontinence. It’s certainly true that rushing into anal sex without the proper preparation can make the experience painful.

However, if you follow the advice and techniques in this guide, we PROMISE that you’ll enjoy pain-free anal sex and will not experience any permanent damage to your body! We’ll show you specific techniques that you can use to prepare your internal and external sphincter muscles beforehand so that anal sex is ORGASMIC, not painful!

Myth 3. Anal sex is never enjoyable

If you don’t prepare properly for anal sex, it may not be enjoyable at all. Unlike the vagina, the anus and anal canal don’t self-lubricate so you need to use plenty of lubricant when you engage in any type of anal play or anal sex. This guide will teach you how to ensure that anal sex is extremely enjoyable EVERY TIME!

By educating yourself about the reality of anal sex and anal pleasure, you can prepare yourself psychologically for anal sex and get all of the physical and emotional benefits of anal sex with none of the drawbacks!

Anal pleasure: why anal sex feels so good

If you’ve heard that anal sex can be messy, painful and unhygienic, you could be forgiven for wondering, why does anyone want to try it?

The truth about anal sex is that it can be highly pleasurable for both men and women. A 2009 survey found that 94 percent of women who tried anal sex were able to achieve an orgasm!

So why does anal sex feel so good?

As it turns out, men and women experience anal pleasure differently. For starters, men have something that women don’t – a prostate! A man’s prostate gland is located at the base of their penis, under their bladder and behind the pubic bone.  Often referred to as the ‘male G-spot’ or the ‘P-spot’, the prostate gland is a powerhouse of male pleasure!

One way to stimulate a man’s P-spot is to press on his perineum (the area of skin between his penis and anus). However, the best way to give a guy a P-spot massage is from the inside, by using a thumb, a finger or a special sex toy called a prostate massager. This is known as ‘milking the prostate’ and can make a guy cum without any direct penis stimulation at all!

Women don’t have a prostate – but they do have an A-spot! The A-spot or Anterior Fornix Erogenous zone is a special place at the back of the vagina, near the cervix, where the vagina wall meets the internal structure of the clitoris. This can be stimulated during sex and anal sex!

You probably know the clitoris as the small ‘button’ where a woman’s inner labia meet. But this is just the glans, or head, of the clitoris. The clitoral complex is actually a spongy shaft that reaches almost five inches inside a woman’s body, making it about almost the same length as the average penis!

The clitoral shaft splits into two ‘legs’ that run underneath the labia and reach as far back as a woman’s abdomen. Every single orgasm that a woman ever has will be because of clitoral stimulation, and if anal sex feels good, it’s because it’s hitting her A-spot and pleasuring her clit!

The 2009 survey we mentioned earlier that found 94 percent of women achieved orgasm when they partook in anal sex was the National Survey of Sexual Health and Behavior. Of course, there were MANY FACTORS behind this surprising statistic: less than a third of the women surveyed actually tried anal sex and those that did were likely more experienced, more open to trying new things, and had the benefit of a long build-up with stronger clitoral stimulation, which is probably what made them achieve an orgasm!

How to discuss anal sex with your partner

If you plan to have anal sex with a partner of any gender identity – whether they have a penis, or plan to wear a strap-on for penetration, you need to have an open and frank discussion beforehand. As with ANY sexual experience, consent is key. Anal is definitely not something you just spring on your partner – EVER!

With something as taboo as anal sex, just bringing the subject up can be tricky enough, let alone discussing it!

Here are two effective ice-breakers to try…

  • Read erotic fiction or watch porn that features anal

If you want to discuss anal with your partner, you can suggest reading or watching porn and see how they react. If they show interest, this can be a good conversation starter. You can ask your partner, “What do you think about that?”, or “Is that something you might be interested in?”. Try gauging their reaction and seeing whether they might be open to discussing things further.

  • Volunteer to go first!

We highly recommend that you try to prepare for anal sex alone first before you try with a partner. We’ll show you exactly how to do just that in the next section! However, once you feel comfortable with the sensations of being penetrated anally and are ready to take things further, you can ask your partner to try something with you.

The best approach is to volunteer to go first. If you’ve been trying out a butt plug on your own and want to share it with your partner, trying saying something like, “I bought this new toy that feels amazing, do you want to try it with me?” Once your partner sees how wet and turned on it makes you, they may be more open to trying!

Establish your comfort levels

If you feel that anal might be something your partner is interested in, you can discuss and establish your comfort levels. Do they feel comfortable exploring anilingus (oral sex on the anus)? Are they up for trying an anal massage? Would they like to experiment with anal fingering? Are they open to playing with anal toys?

Don’t pressure yourself

There’s no need to pressure yourself or your partner to try something you aren’t ready for. Try to find some common ground where you feel comfortable and ready for so that you both have the most enjoyable experience.

You can try addressing some of the anal myths that we highlighted above, such as the fear of poop or anxieties that anal sex will be painful. You can discuss ways to minimize or eliminate pain or discomfort by taking the right precautions.

Set a safe word

An extremely important step is setting a safe word. A safe word is a special word or phrase that you agree on with your partner. When used, it signals that sex must end immediately. Using a safe word helps build trust between you and your partner when trying new activities such as butt play and anal sex.

How to keep things hygienic

One the most common fears for people who haven’t tried anal sex is encountering poop. As we explained earlier, poop is stored in the upper bowels, not the anal canal, so this shouldn’t be an issue, especially if the receiving partner is having regular bowel movements. However, there are some special precautions you can take to keep things hygienic when preparing for anal sex.

The most essential hygiene precautions are:

  • Keeping fingernails clipped (to avoid cutting or tearing the sensitive anus during activities such as anal fingering and anal intercourse).
  • Having a bath or shower beforehand.
  • Using the bathroom one of two hours before having sex (if possible).

Contrary to popular belief, you don’t need to give yourself an enema to prepare for anal sex, but many people choose to! Using a small enema bulb with some saline solution or warm water can help get your extra clean and ready for action. It will flush out the anal canal and take with it any fecal residue that may be lurking inside.

Here’s how:

How to give yourself an enema

Fill an enema bulb with warm water or a saline solution and apply lubricant to the tip. Sit on the toilet and reach down to insert the tip of the enema bulb into your anus. Gently squeeze the water inside yourself and hold the water in for a few seconds. Release the water into the toilet. Repeat this a few times until the water runs clear.

However…

Before you start using enema bulbs, be aware that regular enemas can introduce an imbalance of electrolytes. There are also risks related to internal muscle function if you repeatedly use too much water, or at too high pressure.

Let’s talk about lube

As the anus and anal canal aren’t self-lubricating like the vagina, you need to use plenty of lubricant when preparing for anal sex. You must use lube whenever you use an enema bulb, finger yourself or use an anal toy – and of course, whenever you have anal sex!

While there are hundreds of different brands, styles, and flavors of lube available, there are three main types of lube that you should know when preparing for anal sex.

They are:

  • Water-based lube
  • Desensitizing lube
  • Silicone-based lube

Water-based lube

Most people use water-based lube when they prepare for anal sex because it’s compatible with every sex toy material. Although water-based lubes don’t last as long as silicone-based lubes, they are easy to apply, easy to clean off, and are non-staining. They are also fine to use with latex condoms, which is handy to know when you start having anal sex!

Desensitizing lube

You may have heard of special types of water-based lubes called desensitizing lubes. Desensitizing anal lubes contain added ingredients that numb the anus and anal canal, helping to ease some of the potential discomfort associated with anal sex.

While desensitizing lubes can seem appealing, they certainly aren’t necessary for preparing for anal sex. If you experience any type of pain when preparing for anal sex, you need to stop. Trying the ‘push through the pain’ can lead to serious injury. If something isn’t working, just stop and come back to it later!

Silicone-based lube

The third type of lube you should know about is silicone-based lube. This lasts much longer than water-based lube and is hypoallergenic making it ideal for individuals with sensitive skin. However, silicone lube will damage the surface of silicone sex toys, making them rough and unhygienic, a definite no-no!

One option is to use silicone-based lube whenever you are fingering yourself (or your partner is fingering you) and then switch to water-based lube any time that you use a silicone sex toy. Another option is to use sex toys made from materials such as glass or steel that aren’t damaged by silicone-based lube!

Learn how to finger your anus

One of the best ways to prepare for anal sex is to learn how to finger your anus. This is known as anal fingering and is a great way to prepare for anal. We recommend trying it alone first so that you can explore your anus and anal canal and experiment with how your body responds to being touched.


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Think of anal fingering the same way you think about masturbation; touching yourself helps you understand how your body works and helps you become more comfortable with different sensations. Fingering is a really great way to prepare yourself for anal sex as you can start off at your own pace and explore the inner workings of your body in private.

Even if you started reading this guide because you wanted to learn how to help your partner prepare for anal sex, we still recommend practicing anal fingering on yourself first!

Why?

Exploring your own tush is the BEST WAY to learn how anal fingering feels. It helps you learn the best techniques to use and FORCES you to appreciate the importance of going slow and gentle when exploring your partner’s anus.

Most importantly, learning how to finger your own anus teaches you why you should never rush anal sex and why you must ALWAYS give your partner time to relax and feel comfortable when you penetrate them anally.

Choosing the best position

Before you start to explore your anus, you need to get as relaxed and comfortable as possible. Most people prefer lying on their sides with their upper leg propped up on a pillow or bolster pillow. This ‘spoon’ position gives you easy access to your anus while remaining relaxed.

When you’re ready to start fingering yourself, apply plenty of lube to your index or middle finger and reach around to touch your anus.

How to anally finger yourself

To prepare for anal sex, you need to let your body adjust to being touched in a whole new way! If you’ve never penetrated your anus with your finger before, we suggest using four specific techniques to make the process pain-free.

Step 1. Learn how to relax your external sphincter

As we discussed earlier, your external sphincter is a voluntary muscle, so you can learn to relax it. Start by gently pushing your lubricated fingertip into your anus and pushing in one direction for about five seconds. As you do this, try pushing as if trying to push something out of your butt.

Do you feel the muscles start to relax? These muscles are part of your external sphincter and, with practice, you can learn how to relax them.

(Redraw with one arrow going down and one going up)

After pushing with your fingertip in one direction for five seconds, push in the opposite direction for another five seconds.

If you’re patient, you’ll learn how to relax your external sphincter. This is one of the most important techniques for preparing for anal sex and you’ll need to know this any time you have anal sex to make the experience pain-free.

Step 2. Learn how to relax your internal sphincter

Once your external sphincter is nicely relaxed, you should be able to slide your finger inside your anal canal up to the first joint. At this point, you should be able to feel a ring of muscle contract around your finger.

Feel it?

This is your internal sphincter – it’s not a voluntary muscle so you can’t consciously control it. If you’ve heard that anal sex is painful, this is the most likely culprit. People that rush into anal sex without properly preparing can damage their internal sphincter and be put off trying anal sex ever again!

To encourage your internal sphincter to relax, you need to use a specific breathing technique. Inhale deeply through your mouth for two seconds, taking in as much air as possible. Then, slowly exhale through your nose, counting to five seconds as you do. Repeat this five times and you should feel the pressure lessening around your finger, a sign that your internal sphincter is starting to relax.

Step 3. Let your anal canal adjust

The third step is pressing up and down with your finger in slow, measured motions. This helps your anal canal adjust to the sensations of being penetrated and helps it relax.

Step 4. Insert a second finger

This is the most important stage of preparing for anal sex. If you rush this stage and try to insert two fingers before you are ready, you can damage your internal sphincter, so go SLOWLY!

To prepare for anal sex, you need to acclimatize your anus and anal canal to accept something roughly the same girth as an erect penis (11.66cm according to this study). For most people, two fingers are ideal!

To do this, simply slide out your first finger, apply more lube to both your index and middle finger and then follow the first, second and thirds steps again. Use the same pressing, pushing and breathing techniques until your anus can comfortably accept both fingers.

Experiment with anal toys

When you’re comfortable with anally fingering yourself, another great way to prepare for anal sex is to experiment with anal toys. Anal toys offer a variety of different sensations and sizes that can help you control how your anus and anal canal respond to being touched and penetrated. They are a great way to prepare yourself for anal sex on your own, and you can also use these toys with your partner as soon as you feel comfortable.

While there are thousands of different anal toys available, most of them fit into one of the following three categories:

  • Anal beads
  • Butt plugs
  • Anal dildos

Here are our picks for the best anal toys to prepare for anal sex!

Anal beads

Anal beads are a super-fun way to prepare for anal sex as their tiny tips just slip right in without ANY pain! If you choose a set of quality beads made from 100% medical-grade silicone, you’ll find that water-based lube makes the surface silky smooth!

Technique:
Choose a comfortable sitting, standing or lying position and apply water-based lube to your anus and the anal beads. Begin by sliding the smallest bead past your anus and let yourself adjust to the sensations. Use the pushing and breathing techniques we outlined in the fingering section to help your internal and external sphincter muscles relax. Experiment with sliding the beads in and out of your anus at different angles until your internal sphincter is relaxed and you are able to begin to enjoy the sensations.

Advantages:

  • At their tip, anal beads are smaller than any fingertip, making them perfect for even the tightest of butts!
  • Anal beads come in a wide variety of sizes so you can begin small and work your way up as you gain confidence.
  • Anal beads are streamlined and curvy, all but eliminating pain!

Disadvantages:

  • Although you can buy anal beads that are uniform diameter, most anal beads are tapered with the smallest beads at the tip. If preparing for anal sex if your goal, this won’t help you prepare your anus to accept a penis-shaped object. You may want to transition from tapered beads to larger beads as you become more experienced.

Butt plugs

Butt plugs are a great way to prepare for anal sex as they let you experience the girth and length of a penis-sized object before transitioning to the real thing! Available in a phenomenal range of shapes, sizes, and colours to suit every taste, butt plugs are one of the best anal sex preparation toys to use alone or with a partner.

Technique:
Adopt a comfortable position and apply plenty of water-based lube to your anus and the butt plug. Follow our four-step anal fingering guide except using the butt plug instead of your finger. Begin by pushing the tip of the butt plug into your anus and then pushing out to relax your external sphincter muscle. Use the deep breathing technique we outlined earlier to help your internal sphincter relax until your anal canal can accommodate the entire plug. Start with the smallest, slimmest butt plug and then work your way to a penis-sized plug as you gain experience.

Advantages:

  • There are hundreds of sizes of butt plugs to suit every experience level so you can be sure of finding a plug that feels good!
  • Vibrating butt plugs (using a corded remote or a wireless remote) can make the experience even more pleasurable and can help your anal canal relax and accommodate the butt plug even more readily. Who you give the remote to is up to you!

Disadvantages:

  • Butt plugs can be painful if you don’t warm yourself up first! You may want to try anally fingering yourself or using anal beads before trying to slip a butt plug into your anus!
  • Remember: anal training is a marathon, not a race! Always go super-slow and become comfortable with slimmer butt plugs before working your way up to larger plugs!

Anal dildos

Dildos are a great way to prepare for anal sex, but what if your favourite dildo is too large for anal action? That’s where anal dildos come in handy! Anal dildos are generally smaller and slimmer than regular dildos and are made especially for backdoor fun! Most anal dildos are either glass, steel or silicone and each of these materials has their own pros and cons.

Technique:
Adopt a comfortable position and apply plenty of lubricant to your anus and your chosen anal dildo. If you’re using a silicone anal dildo, remember to use a water-based lubricant, but if you’re using a glass or steel dildo you can use a silicone-based lubricant. Follow our four-step anal fingering guide except use the anal dildo instead of your finger! Begin by pushing the tip of the dildo into your anus and then pushing out to relax your external sphincter muscle. Use the deep breathing technique we outlined earlier to help your internal sphincter relax until your anal canal can accommodate the entire dildo.

Advantages

  • Anal dildos come in a wide range of shapes and sizes including ultra-realistic penis-shaped models. Out of all anal toys, this type of anal dildos is best for preparing for anal sex as you can train your anus to accept a penis-shaped object.
  • Anal dildos that are at least five or six inches can reach far enough inside to stimulate your P-spot (if you’re a guy) or A-spot (if you’re a girl). This makes anal dildos one of the most exciting and satisfying anal toys you can try!

Disadvantages

  • If you choose a realistic anal dildo with a penis-shaped tip, you’ll need to warm yourself up fully before trying to insert it. Try anally fingering yourself or using anal beads or a butt plug before you try inserting this type of anal dildo!

How to prepare for anal sex with your partner

Once you feel confident with anal fingering and using anal toys on yourself, one of the best ways to take your anal preparations to the next level is to involve your partner! You can show your other half EXACTLY what feels good and teach them precisely how to stimulate you to make your orgasm. Once you start having anal sex, this is all but guaranteed to make the whole experience much more enjoyable, pain-free and ORGASMIC for you BOTH!

Here is our complete step-by-step guide to preparing for anal sex with your partner!

Ask your partner to give you an anal massage

One of the most important parts of preparing for anal sex with a partner is becoming completely relaxed and comfortable. And what better way to do that than by giving an erotic anal massage? Choose your favorite massage oil and ask your partner to massage your body while you lie down. Let them caress your hottest erogenous zones such as the nape of your neck, your ear lobes, your breasts, your inner thighs, and your butt.

As they move towards your butt, encourage them to swirl their fingers around your anus. This will help improve blood circulation which maximizes pleasure and helps your external sphincter muscles relax. When you feel ready, you can guide your partner through the four-step anal fingering process that you mastered on your own. Guide and direct your partner so that their fingers move into exactly the right places!

Ask your partner for anilingus

Anilingus (oral sex on the anus) is an AWESOME way to prepare for anal sex with a partner! It’s the perfect way to compliment an erotic anal massage and is sure to help you relax and prepare for anal sex!

Tell your partner to kiss, lick and tongue your anus in just the way you like it! Let them know what feels good and be specific: tell them how hard, how fast and which places feel BEST! If your partner’s tongue is long enough, you can ask them to tongue your anus to give you a completely unique sensation that is sure to make your squirm with pleasure!

Use anal toys during foreplay

Once you’re comfortable using anal toys on your own, you can share them with your partner and incorporate them as part of your regular foreplay routine. For example, as your partner goes down on you and gives you cunnilingus, you can ask them to slip some anal beads or a butt plug into your ass for some exquisite sensations!

If you have a remote-controlled vibrating butt plug, why not give the remote to your partner and let them tease and excite you while they eat you out? There are COUNTLESS ways to make foreplay orgasmic when you use anal toys and they are GUARANTEED to help make preparing for anal sex much more fun!

Ask your partner to anally finger you

Anal fingering on your own is great but with a partner it’s even BETTER!

One of the best positions for asking your partner to anally finger you is in the Spoon. Here’s how it’s done.

Technique
To prepare for anal sex with your partner, lie on your side with your uppermost leg bent at the knee. Your partner lies behind you and rests their uppermost leg between yours if they wish. This position helps you relax and gives your partner easy access to your more sensitive erogenous zones! As they kiss the back of your neck, they can slide one of their lubricated fingers into your anus with ease. You can verbally guide them through the four stages of anal fingering that we described above while you practice the pushing and deep breathing techniques. This is a sure-fire way to help prepare yourself for anal sex!

Conclusion

If you wanted to know how to prepare for anal sex, hopefully, this guide has answered all your questions! We’ve shown you how to prepare yourself mentally and physically for anal intercourse and how to make it fun, clean and orgasmic!

The key to preparing for anal sex is to take things slow and give yourself time to relax and adjust to the sensations. We HIGHLY RECOMMEND trying out anal fingering and anal toys alone first, before trying them with a partner! Once you learn how your body works and how it responds to being touched, you’ll be far more likely to enjoy anal sex!

Hopefully, this entertaining guide has covered the ins and outs of preparing for anal sex.

If you have any questions, comments, or concerns about preparing for anal sex, sound off below and I’ll get back to you as soon as possible!

Have fun!

 

1 thought on “How To Prepare For Anal Sex: The Comprehensive Guide”

  1. I’ve actually never done anal with my girilfriend, she thinks it’ll be quite painful. But after reading this article I’ll try to convince her it’ll be quite a good time.

    Reply

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