Anal Training Guide for Safe and Sexy Anal Stretching

Whether you are just starting your anal adventure, want to work your way up to anal sex, or you are seasoned pro looking for bigger and better things, anal training can help you get there in a safe, sexy, and pain-free way. And if you are going to train for anything, at least anal training is going to give you a whole lot of pleasure! Marathon training? No thanks, I’ll stick to anal training!

While anal training might sound rather serious, it can actually be a very sexy endeavour. You can embark on this adventure solo or with a partner and there is plenty of pleasure along the way!

What is Anal Training?

Anal training is the process of gradually working your way up to being able to enjoy penetrative play with bigger anal safe sex toys or a penis. While you might think this only involves stretching your anus and sphincters, it actually involves a large psychological component too! Successful anal training relies on your brain and butt working together to become more comfortable with penetrative anal play!

Getting your brain and booty working together really ‘opens up’ your anal play possibilities!

First up, we’ll look at anal training for beginners, followed by some recommendations for advanced anal stretching toys and tips. Oh and of course we’ll go over some essential anal play safety to keep your butt happy and healthy!

Let’s dive in…I mean ease ourselves in gradually and with plenty of lube!

Anal Training for Beginners

If you are just getting started with anal play, it’s totally normal to feel a little nervous, even if the thought also excites you. The majority of us have grown up with anal play being somewhat of a taboo, which can, of course, impact our feeling towards anal play. It can take a bit of time to work through these negative narratives, so be patient with yourself!

But I am here to reassure that when done properly, you can have pain-free anal sex that unlocks a whole new world of pleasure! Of course, like anything, it won’t be everybody’s cup of tea, so always listen to your body to find out what does and doesn’t feel good.

Anal Training Sets for Beginners

Before you get started, you are going to need some anal toys to help you on your training journey! I would recommend buying an anal training set that includes a set of tapered butt plugs in increasing sizes, as they are often cheaper than buying individual plugs or come with some handy extras! Here are some of my favorites:

b-Vibe Anal Training Set

This luxurious anal training kit from b-Vibe comes with three different plugs of increasing size, a douche, a lube applicator, and an anal play guide! The medium plug also has added vibrations for some extra stimulation!

Mood Naughty Set


The Mood Naughty set has three different size plugs to explore. The tapered tip makes them easy to insert and the t-bar base and thin neck mean they are very comfortable to wear while you enjoy whatever else takes your fancy!

Crystal Booty Kit


If you prefer a little more bling for your booty, the Crystal Booty Kit from Cal Exotics are topped sparkly gems to make your tushy shine like the start it is! The smallest plug in this set is a tiny 0.5 inches wide, making it the smallest out of the three sets here.

How to Start Anal Training

Our butt holes, specifically our sphincters are like guards that are programmed to relax when only it’s safe to go the toilet, and at all other times, they prevent anything from exiting or entering. Not to mention, you might not be used to touching your anus directly or having someone else touch it. Learning how to relax tight sphincter muscles takes some time as your brain needs to register that anal stimulation, both external and internal, is actually pleasurable and not a risk. Here are some tips to help your brain and butt relax:

  • Use deep breathing to help you mind and muscles relax.
  • Listen to your body and stop when you feel uncomfortable or feel any pain. Honoring your body’s cues also helps you to feel safe in the situation.
  • Lube is the unsung hero of anal play. Use it liberally! As well as lubing up your anus and whatever sex toy you are using, you can use a lube applicator to lubricate the inside of your anus.
  • Take it slowly to give yourself time to adjust, and enjoy the journey!

Anal Training Step by Step

Now, we’ll walk through how to work your way up to bigger toys or train for penetrative anal sex with a penis or dildo.

Right place, right time

To start your anal training journey, you want to make sure you are somewhere you feel comfortable — I would suggest your own home. You can prepare your space by with a couple of towels and maybe some wet wipes, your chosen sex toys, and some anal lube.

On top of that, choose a time when you don’t have any other commitments and you don’t need to rush off somewhere straight after.

Have a good clean

It’s best to void your bowels before anal play. Your body actually stores poop higher up in your colon, so unless you feel like you need to poop or you have digestive issues, the lower part of your colon and rectum should be relatively clean.

I would recommend taking a shower and cleaning your anus externally. Some people choose to douche first, but this isn’t necessary and doing this too often can actually be damaging.

Get relaxed

As well as being a great way to get clean, a warm bath or shower can help relax your mind and loosen up your muscles. You can also set some soft lighting or diffuse some relaxing scents — whatever helps you feel at ease!

Get in the mood

You also want to set the right context for pleasure in your mind by getting yourself nice and aroused. When you are feeling safe and turned on, your brain is more likely to interpret anal play and anal training as safe and pleasurable.

  • Use your imagination and fantasize about some sexy scenes
  • Watch some ethical porn
  • Listen to some audio porn
  • Read some erotica
Start with some external stimulation

To get used to the sensation of anal stimulation, you can start by stimulating the anus and area around it. I would recommend pairing this with some clitoral or penis stimulation as well to help the brain register that is seriously sexy! Here are some ideas to try solo or with a partner:

  • Massage your butt cheeks to get the blood flowing and loosen up your muscles
  • Use a lubed up finger to stroke and massage the anus and perineum (a.k.a. taint)
  • Use an anal vibrator to stimulate your anus and perineum
  • Engage in some rimming (analingus)
Move onto penetrative anal play

When you feel completely comfortable and ready, you can start to explore penetration. It might take you a few sessions to work up to this and that is totally ok! It’s better to go slow, as going to fast can activate your fear response and make you tense up — the opposite of you actually want!

Take the smallest butt plug or anal toy you have and apply plenty of lube to the insertable part and directly to your anus. Lube really is your best friend here!

Breath deeply as you insert the tip first and allow your body to adjust to that feeling before inserting any more. If you feel comfortable to do so, keep going until you feel the plug or finger slide inside. Allow the plug or finger to just be inside you as you adjust to the sensations.

When you remove the toy, remember to breath. You can squat and bear down slightly to help it on the way out!

Allow your body to fully adjust

Don’t be tempted to try something bigger too soon. Instead enjoy the size you can take now. Depending on how often you practice, roughly one to two weeks is a good amount of time to adjust to one size before trying the next size up. However, everyone is different so there’s absolutely nothing wrong with staying at the same size for longer! You can incorporate it into other sexual activities and enjoy all the new sensations you are feeling!

Sizing up your anal training

When you are ready to move onto the next size, make sure to increase the size gradually. I would suggest increasing the diameter by no more than 1/4 of an inch each time.

It’s also a good idea to follow the same steps as before and even use the smaller plug or a finger to warm up each time.

Moving from anal training to anal sex

Keep gradually increasing the size of toy you are comfortable using until you reach a similar size to that of your partner’s penis or dildo. When you feel ready to try penetrative sex, warm up with your smaller toys first and be sure to go slowly, as having a dildo or penis inside you will feel more intense than a butt plug as they are the same width all the way down and they will be moving in and out.

Be sure to communicate with your partner to let them know when you are ready for more, when you need a break, and what does and doesn’t feel good.

Advanced Anal Training and Anal Stretching

If you are already adept at the anal arts, you might be looking for more of a challenge. There are plenty of reasons people feel that is better when it comes to anal play, including increased sensation, a satisfying feeling of fullness, and the psychological element of pushing your body and discovering what it can do!

As the anus isn’t a naturally stretchy part of the body, like the vagina, you do have to exercise some caution when you are using bigger sex toys. Going to too big too soon or not warming up properly can result in micro tears, which apart from being painful, can leave you open to infections.

The answer to going big with backdoor play? You guessed it! Anal training!

Anal Training Kits and Anal Toys for Advanced Anal Stretching

As you move onto bigger anal toys, there aren’t as many options for high quality training kits, but you buy plenty of large butt plugs separately! Larger toys are often made of porous materials as they tend to be cheaper, but they can harbour germs and mold over time, so be sure to look for something made from silicone, borosilicate glass, or stainless steel. As well as using butt plugs, anal dildos, big anal beads, or inflatable butt plugs are all great for more extreme anal stretching!

Here are some high-quality large anal toys to take you to the next level…

b-Vibe Glass Dilators

The thick neck and weightier glass construction of this dilator set from b-Vibe is perfect for advancing your anal play. The largest size measures a juicy 1.7 inches at the widest part, so this is best suited to intermediate levels.

Inflatable Butt Plug

Made from safe and strong silicone, this inflatable butt plug expands to fit your desires. The simple balloon pump inflates the the plug to give a sexy stretch and feeling of fullness. It also has a quick release valve for safety.

Tantus XL Anal Cone

Not for the faint hearted, the Tantus XL Cone is a beast of anal dilator! Two inches as the widest point, you can gradually increase how much of the cone you insert, from just the tip to the whole eye watering 8 inches!

How to Stretch Your Anus for Advanced Anal Play

Whatever anal safe sex toys you decide to use, there are some simple steps to follow for safe and sexy stretching!

  • Never skip the warm up! As you get more experienced, you might be tempted to dive straight in with a go big or go home attitude. However, just like at the gym, you still need to warm up! Take the time to savour some anal foreplay, and enjoy a smaller toy or two before going for a bigger size.
  • Don’t be tempted to jump up too big in size. Your anus feels every millimeter so as always, take it slow and listen your body!

How Far Can You Put Something up Your Bum?

So far, we’ve focussed on stretching the sphincters and anus to be able to enjoy girthier penetrative play, but another type of anal training is depth training. As the rectum doesn’t have an end point — it connects to the colon, you can insert longer sex toys into the anus or engage in activities like fisting, which stretches you in both directions.

Again, it’s super important to work your way gradually to using longer anal toys. You need to familiarise yourself with the sensations and ease your body into the experience. Deep penetration also comes with more risks, as you are essentially inserting something into your colon. On top of that, the lining of your colon is easy to damage and there aren’t the same kinds of sensory receptors there, so your experience of pain will be different.

If you do want to practice anal depth training, familiarise yourself with the risks involved first, tune in very carefully to the sensations in your body, always use plenty of lubrication, and only use anal safe sex toys made of 100% silicone.

Anal Snakes

Anal snakes and extra long anal toys can help you explore depth training and work your way up to deeper penetration. Some, like the 18-inch Anal Snake from Hosed, have measurements along the length, so you can see exactly how deep you can go! It also has a handy suction cup base.

What to Expect After Anal Training

Aside from the desired effects of stretching your anus and being better prepared to enjoy anal play, there are some other effects of anal stretching. No matter your level, there are few things to expect after stretching your anus and sphincters. Here are some normal things that might happen.

The Three G’s of Post Anal Stretching

  • Gaping — After stretching your anus, it can stay open for a little time before it shrinks back down to it’s regular size, especially if you have been using larger toys. Not only is this totally normal, but also some people find it incredibly arousing and engage in anal play purely for it!
  • Gas — Yes, you might experienced increased gas after anal stretching, as it’s possible for air to get trapped inside you as you play. This is nothing to worry about and shouldn’t last too long.
  • Going to the toilet — You might also find that your bowel movements are a little irregular after anal sex. Again, this is to be expected after entering an exit route!

It’s normal to feel a little sore or uncomfortable after anal stretching as your butt isn’t used to this new sensation. You might also notice a small amount of blood when you wipe after going to the toilet. This is most likely from a micro tear, which will usually heal up by itself. If you notice anything other than minor pain or a very small amount of blood, you should seek medical advice.

Taking a shower or having soothing a bath with some Epsom salts can be a great way to get clean and take care of your butt after anal stretching. Some people also like to use a moisturiser, externally around the anus to help protect the skin.

Anal Stretching Safety

Anal stretching is all about pleasure but there are some risks involved. Here are some tips to minimise the risk of injury during anal training. You can read more in our post about butt plug safety!

  • Always use anal safe sex toys that have a flared base to prevent the toy from slipping inside your body.
  • Listen to your body. If you feel any pain or discomfort, stop and take assess the situation.
  • If you have a lot of pain or anything more than a small amount of bleeding, seek medical advice.
  • Never use anal numbing lube. If you can’t feel pain, you might not realise you are about to or already have injured yourself.
  • Take things slowly. Patience is really a virtue when it comes to anal play!
  • Use a LOT of lubrication! If you are using silicone sex toys, stick to using a thick water-based lube. However, if you are using glass or metal, I would recommend silicone lube as it’s longer lasting.
  • Reapply lube whenever you feel any friction.
  • Practice good hygiene. Wash your hands and sex toys before and after anal training to keep everything clean.

Are there any risks to anal training?

As with any sexual activity, there is some level of risk involved in anal training. You are essentially putting something inside a hole that is meant to be an exit point. Following all of the correct safety guidelines will minimize the risk considerably. That being said, it’s important to know the risks involved. If you are in any doubt, always talk to medical professional.

Anal Fissures

These are tears in lining of your anus that can happen as a result of anal sex, especially if you don’t warm up properly and use adequate lubrication. While most will heal without any issues, they can be painful and leave you more susceptible to some STIs and other infections. If you feel like your anal fissure isn’t healing or you notice any signs of infection, be sure to see a doctor.

Aggrevation of Existing Problems

If you have any existing anal or rectal health issues, such as hemorrhoids, anal stretching can exacerbate the problem. In this case, it’s best to wait until the issue has resolved.


The risk of perforating your colon is minimal when using smaller sex toys or having sex with a penis. However, there is more risk if you are engaging in deeper anal play with long anal sex toys, fisting, or if a sex toy is fully inserted into the anus, as it can travel up into your colon. This always requires immediate medical attention.