Are you curious about exploring anal sex but scared that it will hurt too much? The SECRET to making backdoor sex feel unbelievably great is a little-known practice called anal training!

If you want to learn how to enjoy anal training – either by yourself or with a partner – then you’ve come to the perfect place! In this illustrated guide, you’ll learn everything you need to know about training yourself or your partner to enjoy anal penetration.

After reading this guide, your sex life will never be the same again…

This guide has something for everyone – no matter your gender or sexual orientation. If you want to learn how to enjoy anal sex, without pain or discomfort, then keep reading…

Here, you’ll find a treasure trove of helpful suggestions and proven techniques that will help make your training safe, hygienic and, most importantly, fun! This guide is a MUST READ for anyone who wants to learn how to start anal play and unlock the pleasures of backdoor penetration!

As anal play and 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 practices discussed herein. All opinions expressed are those of the writer and have not been written or reviewed by a physician or healthcare professional. Always abide by the laws of your country.

Sound fair?

Then let’s get started!

What is anal training?

Anal training is the practice of training the anus and the muscles around the anal canal to relax during anal penetration or anal sex. Unlike the vagina, the anus is not designed to be penetrated and doesn’t self-lubricate, so training is an essential part of preparing for anal sex.

The goal is to help an individual become comfortable with being penetrated anally and to make anal sex feel more pleasurable. Anal training covers a wide range of practices, from anilingus (oral sex on the anus) to fingering, fisting, and using toys such as butt plugs, anal wands, anal beads, vibrators, dildos, and prostate massagers.

This can be a solo activity, where an individual explores their own body and stretches the limits of what their butt can accommodate. It can also be done with a partner, either during mutual masturbation, foreplay or within a power relationship where one partner actively ‘trains’ the other, or instructs them to train themselves.

The benefits of anal training

If you want to experience enjoyable anal sex, training is a MUST.

The main benefits are:

Enjoyable, pain-free anal sex

Pre-training makes anal sex far more enjoyable and greatly reduces the chances of it being painful for the receiving partner.

A higher chance of reaching orgasm during anal sex

Both men and women can orgasm during anal sex, but only if they are relaxed and comfortable. Training helps make the receiving partner more relaxed and therefore more likely to achieve an orgasm during butt play and anal sex.

Reduced risk of injuries

Engaging in anal sex without training first is incredibly risky and can lead to painful, and sometimes permanent, injuries, such as rectal prolapses and incontinence. By taking the proper precautions, training is the best way to reduce or eliminate the risks associated with anal penetration and anal sex.

Anal anatomy

Before we dive into the fun stuff like fingering and toys, we need to explore some important anatomical areas first. If this seems like a yawn, did we mention that this will help you and your partner achieve stronger, more powerful orgasms?

Listen. Whatever your gender or sexual orientation, some aspects of your anal canal anatomy will be exactly the same as everyone else, so let’s discuss those areas first!

The anus marks the opening of the anal canal and is made from soft tissue that is PACKED full of sensitive nerve endings! The anus is one of the body’s HOTTEST erogenous zones and feels toe-curlingly good if it’s touched in the right way…

However, touching the anus can also cause quite a lot of pain if you don’t know what you’re doing!

Venture a few inches inside the anal canal and you’ll find the Dentate line, beyond which is the rectum. The rectum is about eight or nine inches long and has far fewer nerve endings that the anal canal or anus.

Before trying any form of butt play, you should know that:

• The anus and anal canal are sensitive to touch and vibration, while the rectum is more sensitive to pressure. (This will come in handy later when we discuss anal fingering!)
• The rectum isn’t straight. Most rectums curves towards the navel, then back towards the spine and then towards the navel again, forming a letter ‘S’. Some rectums curve laterally. Everyone is different, so you must take things slow and gently while you explore your own or your partner’s anus and rectum.

Next, let’s look at 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 is made up of layers of circular muscle tissue. The layer of striated muscle that surrounds this is the external sphincter.

You need to know that:

• The internal sphincter is not under an individual’s voluntary control (it’s controlled by the central nervous system). It takes time to relax and can easily be damaged (sometimes permanently) if is rushed or forced.
• The external sphincter is a voluntary muscle that an individual can learn to relax, but this takes time (and training!).

While everyone’s anal anatomy is virtually identical, there are some crucial differences in the ways that men and women experience pleasure. If you or your partner is female, you’ll need to be familiar with female internal anal anatomy, which looks like this…

When most people think of the clitoris, they tend to think only of the visible head, known as the glans, at the top of the vulva where the inner labia meet. However, the clitoris is actually a spongy shaft that reaches almost five inches inside a woman’s body. In fact, the average clit is 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 the abdomen.

If you or your partner is female and you’re interested in getting the maximum pleasure from anal, the most important area to know about is the A-spot or Anterior Fornix Erogenous zone. This is a small area at the back of the vagina near the cervix. The A-spot is actually part of the clitoris and can be stimulated during anal play and anal sex!

Now for the guys:

Men don’t have an A-spot, but they do have something that women don’t – a prostate! Located under the bladder, behind the pubic bone at the base of the penis, the prostate gland is sometimes referred to as a ‘P-spot’ or the ‘male G-spot’. It surrounds part of the urethra is a veritable powerhouse of pleasure!

It is possible to stimulate the P-spot externally by pressing on the perineum (the area of skin between the penis and anus).

However…

The BEST WAY to stimulate the P-spot in through internal stimulation using a thumb, a finger, or a special sex toy called a prostate massager.

One of the main benefits of training for guys is the chance to experience an ejaculation through prostate stimulation alone! This is known as ‘milking the prostate’ and can lead to explosive ejaculations without stimulating the penis at all!

How to prepare for anal training

You’re probably itching to jump into all the fun stuff like fingering, butt plugs, and anal beads, but wait: There are THREE CRUCIAL STEPS that you need to take before you start training.

These are:

1. Getting into the right head space
2. Choosing the right lube
3. Hygiene

Don’t stress; these steps are quick and fun, so keep reading…

1. Getting into the right head space

The biggest barriers that prevent people from trying anal are often psychological. Anal is taboo because they are commonly thought of as messy, unnatural and even painful. The mass of stereotypes and misinformation out there sows the seeds of confusion and fear.

It’s no wonder that anal can seem scary! And when that happens, you’ll likely find yourself tensing up, a huge no-no if you’re about to put anything in your tush!

To get into the right head space, you need to get well read-up on the truth about anal penetration. If you’ve heard horror stories about anal being messy, rest assured that poop is actually stored in your upper bowels, not in the anal canal. This is far enough in that no finger, sex toy or penis will be big enough to reach it!

If you’re worried about training being unnatural or painful, well yes, as we discussed earlier the anus isn’t designed for penetration and doesn’t self-lubricate, so using a lubricant is mandatory!

Cutting through the myths will help you (and your partner) address and some of the hang-ups and anxieties you may have about training. This lets you start training in a good head space where you are better prepared for what to expect!

2. Choosing the right lube

As we mentioned, using plenty of lube is absolutely essential for any form of anal! Lube quickly and effortlessly helps your anus and anal canal prepare for penetration. But the type of lube you choose is equally important.

There are four main types of lube:

• Water-based lube
• Silicone-based lube
• Oil-based lube
• Desensitizing lubes

Here’s a quick run-down of their pros and cons that will help you choose the right type for your needs.

Water-Based Lube

Water-based lube is ideal for ANY type of anal. It’s compatible with every sex toy material and is safe to use with any type of condom.

The main drawback of water-based lube is that is doesn’t last as long as other types. This means you have to frequently reapply more as needed. However, water-based lube is ridiculously easy to clean, helping to make cleaning up after training an absolute breeze!

Silicone-Based Lube

Silicone-based lube lasts longer than water-based lubes meaning that you don’t have to re-apply it as often. Whatsmore, it’s hypoallergenic making it ideal for individuals with sensitive skin.

However, there is one caveat:

If you use silicone-based lube with a silicone sex toy, the surface of the sex toy will become damaged over time. This not only makes the surface rougher (and more uncomfortable), it also makes it unhygienic.

Oil-Based Lube

Your third option is oil-based lube. Oil-based lubes are the longest-lasting lubes you can buy and they are perfectly safe to use with sex toys.

On the downside, they are difficult to wash off and have been associated with higher rates of sexually transmitted infections (STIs) compared with water-based and silicone-based lubes. Oil-based lubes may also stain clothing and bedsheets, making them no fun to wash off!

Desensitizing lubes

Desensitizing lubes contain special ingredients that can help ease some of the potential discomfort associated with anal. These water-based products help eliminate friction while offering a numbing effect to the anus and anal canal.

While it can be tempting to want to keep things as comfortable as possible during training, we don’t recommend desensitizing lubes for beginners!

If training is painful, you need to stop. Pain is your body’s way of telling you that something is wrong, so you don’t want to ‘push through the pain’ and put yourself at the risk of being seriously injured!

You can’t undo an injury once it occurs, but you can stop and try something smaller if anal play causes you pain. Just take a break: you can always work up to larger sizes on another occasion!

3. Hygiene

There are some basic hygiene practices you should observe before starting anal play.

These are:

• Having a shower or bath
• Trimming your fingernails
• Using an antibacterial hand soap

Contrary to popular belief, you don’t need to use an anal douche or have an enema before anal, although many people do! If you’re having regular bowel movements, then you should be in the clear before starting training. If you can use the bathroom one or two hours before you start, then all the better.

That being said, most people are worried about encountering fecal residue during training and anal sex, so enemas are a popular option. If you want to get yourself really clean prior to anal, you may like to use a small enema bulb:

To use an enema bulb, simply fill the bulb with water (or saline solution) and put plenty of lube on the tip. Sit on the toilet and insert the tip of the bulb into your anus. Squeeze the water inside yourself and hold the water in for a few seconds before releasing it. Repeat this a few times until the water runs clear.

That’s it – you should be good to go!

Before you rush out and buy an enema kit (or ask Alexa to order you one), you should know that regular enemas can introduce an imbalance of electrolytes and there are risks related to muscle function if you repeatedly use too much water, or at too high pressure.

Remember:

The same hygiene precautions apply after training too – make sure you shower and use plenty of antibacterial soap after your backdoor fun comes to an end!

Solo anal training

If you want to:

• Explore your anus and anal canal
• Prepare yourself for anal sex
• Train yourself to take larger toys, or
• Explore prostate massage (for guys)

Then this is the section for you! Even if you want to anally train your partner, we still recommend practicing on yourself first!

Why?

Tending to your own tush will make you far more knowledgeable about how your fingers and toys feel and how to use them to give your partner maximum pleasure! You’ll also appreciate the importance of going slow and gentle when exploring your partner’s anal area!

Solo anal play will show you what you should NEVER rush anal and why you must ALWAYS give your partner time to relax and feel comfortable when you penetrate them.

How to finger your own backdoor

The KEY to enjoyable solo butt play is to be as comfortable and relaxed as possible. One of the best positions is lying on your side and using a pillow to raise up your top leg. Put plenty of lube on your index or middle finger and reach round to touch your anus with your fingertip.

We’re going to introduce you to our unique FOUR STAGE training method that will get you ready for anal sex with minimal pain!

Stage One

First, you should gently push your lubricated fingertip into the opening of your anus and hold down for five seconds.

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

Then, push upwards with your fingernail and hold for another five seconds. Repeat these steps a couple of times until you start to feel your anus relaxing.

Stage Two

Next, slide your finger inside your anal canal up to the first joint. You should be able to feel a ring of muscle contract around your finger. This is your external sphincter muscle and this is exactly what you’re going to be training first.

With your finger inside your anal canal, try pushing as if trying to push something out of your butt.

Do you feel the muscles start to relax? This is a sign that your external sphincter is beginning to relax.

However, you’ll still be able to feel layers of circular muscle tissue – your internal sphincter muscles – gripping your finger as you explore the inner surface of your anal canal.

On to stage three!

Stage Three

For the third stage, slowly insert more of your finger inside your anal canal.

While you can’t force your internal sphincter to relax, it will do so if you use a special 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 muscles are starting to relax.

Remember:

Your internal sphincter muscles aren’t under voluntary control and take time to relax, so GO SLOW! This is the most important stage of training: if you rush this stage or try to insert something too large before you are ready, you can do yourself serious, sometimes irreversible, damage.

Stage Four

The fourth stage of training is incorporating a second finger. As the main goal of training is to prepare your body for anal sex, two fingers are ideal as they roughly approximate the girth of an average-sized erect penis of (11.66cm according to this study).

Simply slide your first finger out, apply more lube and follow stages one, two and three again, only this time with both your index and middle fingers together. Once you reach stage three and are able to slide both fingers inside your anal canal, you can curl your fingertips and move your fingers back and forth to help the internal sphincter muscles relax and stretch.

If you need to prepare for a larger penis or want to train yourself to accept a larger toy, you can expand this stage (and your butt!) by repeating this process with three or even four fingers!

Check out our complete guide to anal training to learn how to experience the ultimate in anal pleasure!

Anal training with a partner

Anal training on your own is great in so many ways, but with a partner? It’s even BETTER!

There are SO MANY fun, sexy ways to start training, such as:

• Using a massage oil to give your partner a sexy anal massage before you move to penetrative anal play.
• Performing anilingus (oral sex on the anus) by kissing and licking your partner’s anus.

However, before you explore training with a partner by taking either a dominant or submissive role, you need to lay a few ground rules first.

If you are actively penetrating your partner with your fingers or a sex toy, you need to set a safe word or phrase that they can use if they feel pain. This word is a sign that play needs to stop immediately and must always be respected. This is an essential part of building trust and you should NEVER attempt anal play without a safe word.

The BEST POSITION for anal play your partner is The Spoon.

Technique

Your partner lies on their side with their upper leg bent at the knee. You lie comfortably behind them and rest your legs on theirs if you wish. This position will help your partner relax while giving you easy access to their tush. You can also kiss their favourite erogenous zones such as the nape of their neck, or reach around to masturbate them during the training – something that’s SURE to help them relax and start to enjoy themselves!

The four stages of training with a partner are exactly the same as solo training:

• Stage One: Use plenty of lube on your index finger and press it onto your partner’s anus for five seconds, then repeat by pushing upwards in the opposite direction.
• Stage Two: Insert your finger into your partner’s anal canal up to the first joint and have your partner practice the pushing technique to relax their external sphincter muscles.
• Stage Three: Push your finger further inside your partner while they use the deep breathing technique to encourage their internal sphincter muscles to relax.
• Stage Four: Incorporate a second (or third, or fourth) finger.

However…

Whereas solo anal play relies on what you feel, training with a partner relies on trust and good communication between you BOTH. You need to pay attention to verbal and physical cues and get your partner to tell you when they are ready or when things are painful. ALWAYS abide by the safe word and stop as soon as your partner indicates discomfort.

A guide to anal training toys

Most people begin with fingering before moving to anal toys. But you can just jump in and experiment with some backdoor toy action right away if you wish!

The four main types of butt play toys are:

• Anal plug beads
• Butt plugs
• Inflatable butt plugs
• Rectal speculums

Anal plug beads

If you want to ease yourself or your partner into training then a set of streamlined, curvy anal plug beads is just what you need! Made from 100% medical-grade silicone, beads are completely safe and hygienic and won’t cause any discomfort.

Beginner anal plugs are tapered and feature the smallest diameter beads at their tip. With enough lube, these tiny beads are sure to slip right into even the tightest of butts with ease!

With practice, you can train your anus to accommodate the larger beads and experiment sliding the plug in and out at different angles until your internal sphincter relaxes and you begin to enjoy the sensations. Once you are comfortable with the small beads on the beginner plugs, you can buy larger plugs with wider, thicker beads for added pleasure!

If plugs with a solid core aren’t doing it for you, anal beads with a fabric string are another option.

Butt plugs

Butt plugs are available in a phenomenal range of shapes, sizes, and colours to suit every experience level. You should start with the softest, smallest and thinnest models and work your way up!

To unlock your love of anal play, be sure to use plenty of water-based lube and experiment with a variety of in and out motions.

Remember:

Anal training is a marathon, not a race! Go super-slow and steady and take time to work your way up to larger models.

Once you work your way up and want to try something larger, you can try a vibrating butt plug like the b-Vibe Trio Plug. Vibrating butt plugs not only feel AMAZING but they also help your muscles relax and accommodate anal toys of even larger girths!

An EXTRA benefit of models like the Trio Plug is that they come with remote controls, giving you (or your partner) complete control over the vibrations and sensations. This can add a whole other layer to the power dynamic between you and your partner; especially if they are in another room with their fingers on the remote!

Inflatable butt plugs

If you’re SERIOUS about anal play, the inflatable butt plugs are one of the BEST toys you can buy! Simply lube them up and slip them in, then use the hand pump to give you or your partner a nice sense of fullness!

Rectal Speculum

Not for the faint of heart, rectal speculums are UNBEATABLE tools for advanced training! They help you train your partner’s anus and anal canal to accommodate the LARGEST girth sizes!

Rectal speculums open the anal cavity wide and lock in place, giving your sphincter muscles time to relax and adapt. Awesome for fetish and medical play, these stainless steel devices will help you prepare for anal sex without causing cuts or abrasive injuries.

While speculums are designed to be pushed into the anus without any warmup, we HIGHLY recommend following our unique FOUR STAGE ANAL FINGERING strategy before trying one of these out! Always ensure that your partner’s anus and anal canal are nicely lubed up and relaxed before letting experimenting with a speculum.

Tips for making anal training enjoyable

With the right approach and techniques, training can feel incredible! You may even experience one, or multiple, anal orgasms!

But going to town on your tush can be painful and may even lead to injury if you don’t take the right precautions.

So here are FIVE great tips for making training fun and pain-free!

1. Use more lube

A common reason why some people find anal uncomfortable is that they either aren’t using enough lube, or they are letting it dry out and aren’t reapplying more! This is especially common when people are using water-based lube with silicone sex toys.

NEVER let your toys dry out; keep applying more lube at regular intervals.

2. Switch lubes

The second reason why anal may not be fun is the type of lube you are using. If you aren’t getting good results with water-based lube, feel free to move onto a more durable, slippery lube like an oil-based lube. If you’re worried about damaging your sex toys, try putting a condom over them to protect them from the lube.

While we don’t recommend desensitizing lubes for beginners, you can experiment with numbing lubes as you get more advanced and learn how to explore your tush without hurting yourself.

3. Give yourself time to adjust

You can’t move from finger to penis overnight! Not a good idea!

Instead of being goal-orientated – ie. “I want to fit that size” – try focusing on pleasure. You can always try anal in the future if you aren’t ready for a particular size.

Get into the right headspace and always give yourself adequate time to adjust. This will make a huge difference to your enjoyment of anal play!

4. Try Kegels

Kegels aren’t just for vaginas – they work great for anal sex too!

Kegels are special exercises that build up the entire pelvic floor muscle region. This includes the muscles around your anal sphincter.

If you’re experiencing discomfort during anal, Kegels can be great for your backdoor health and give you greater control over your butt muscles.

To find your pelvic floor muscles, squeeze your butt as if holding in poop. Feel those muscles contract? Now, hold those muscles for five seconds and release for five seconds. Repeat this five times.

With practice, you should be able to hold the contraction for 10 seconds. Over time, Kegels will improve your ability to enjoy anal by giving you better control over relaxing and controlling your backdoor muscles.

5. Use tapered toys

If your anus is struggling to acclimatize, a fantastic option is to use tapered toys. You’ll find every type of tapered toy imaginable from tapered anal plug beads, to tapered butt plugs and more!

Tapered toys feature their smallest part at the tip, allowing you to start slow, and then gradually work up in size towards the medium and largest beads. You’ll find a whole range of sizes on offer, from ultra-tiny to fairly sizable!

If you want to ULTIMATE tapered toy, try a vibrating tapered toy like the Triplet Anal Beads; you’ll feel the sensations throughout your ENTIRE BODY! The vibrations will feel exquisite and will help your muscles relax and accommodate larger sizes more easily!

Moving from anal training to anal sex

If you’ve made it this far, congratulations! You’ve officially completed anal sex training and are ready to progress to, well, bigger things! Hopefully, you’ve discovered a love for backdoor pleasure and are wondering – what should I do to move to anal sex?

Once you have trained your butt to the point where you can comfortably enjoy a penis-sized object such as two fingers, a large butt plug or some wide beads, you’re probably ready to take a penis in your backdoor!

Here are THREE TIPS for transitioning from training to anal sex.

1. Try butt play during foreplay

When you’re ready to try anal sex, you and your partner should make butt play a part of your regular foreplay routine. There’s NOTHING sexier than an anal massage to help your muscles relax, and a spot of anilingus doesn’t hurt either! Analingus is a great time to introduce lube, fingering and butt toys like butt plugs, too.

You should still use the basic four-stage training strategy you’ve learned before moving to anal sex.

2. Practice regularly

Just like any muscle group, your sphincter muscles need regular workouts to keep them flexible, limber and ready for action! If you let more than a few weeks pass between having any type of anal play, you’ll probably notice some resistance when you try to play again.

You don’t need to be having continuous anal sex or anal play, but you should have a biweekly or bimonthly ritual where you treat yourself to a little backdoor exploration – maybe during shower time, perhaps?

3. If you do take a break, always start small (again)!

Just because you’ve completed training doesn’t mean you’re set for life! If you take a break, say, longer than a few months, always start with the smallest sized butt plug again and work your way up to larger sizes before trying anal sex.

Conclusion

If you were curious about anal training and wanted to know how to make it part of your sex life, that’s about it! Hopefully, you’ve learned that by taking the right precautions, you can reduce or even eliminate pain and discomfort during anal.

By following the strategies and advice in this guide, we’re confident that you’ll be able to help your body (or your partner’s body) get ready to have some amazing anal sex in no time!

Whether training is a one-off experiment or becomes a regular part of your sex life, either way, we hope you have fun!

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