Our July Theme: Bondage! Get 20% Off Selected Restraints! Use code: KINBAKU at the checkout
Offer Ends Midnight Sunday 04/08/24 - Exclusions Apply

Beginner's Guide To Anal Stretching

<div class= 

What comes to mind when you think of anal stretching? Does your mind wander to the first time you ever saw Goatse? If you've never even tried a butt plug, yet you're interested in having a seriously floppy rectum then look no further than our UberKinky beginner's guide to anal stretching.

There are many reasons why people choose to engage in this anal activity. Some people simply enjoy the stretching sensation, while others have HUGE anal gapingambitions.

Whatever your goal, stretching not only feels amazing, it enables you to expand your horizons to extreme dildos, fisting and other activities which take up more room in your bum. So, let's dive deep into our guide so you can explore something new and exciting.


About The Author

UberKinky has been dedicated to helping people explore new sensations and get to know their bodies at an intimate level for more than 30 years. Whether you are in a relationship or are looking to play solo, we have a wide variety of products and ideas to spice up your bedroom activities.

As multiple award-winners, we know a thing or two about sex, specifically how to get the most out of it.


What is anal stretching?

We know how exciting the prospect of exploring anal sex is, however, to get the most of this experience and, most importantly, stay safe, training is essential.

Training sounds like a lot of hard work, but it is actually a lot of fun.

Anal stretching is the process of training your anus to take a penis and toys of increasing size.

Where you begin your anal stretching training depends on your previous activity. For complete beginners, you may want to start with your fingers before moving onto toys.



Reasons to try anal stretching

Have you often found yourself intrigued by anal play? Do you wonder why it is an activity enjoyed by both same-sex and heterosexual couples?

There’s a reason why people opt for anal exploration. In fact, there are multiple! Here are just some of the UberKinky reasons why people decide to give it a try, and why they get hooked.

1) Enjoy a satisfying stretch unlike anything else

An anus is loaded with sensitive nerve endings and stimulating these results in tremendous pleasure. The fullness you feel when being penetrated is exceptionally satisfying. The fuller you feel, the better the experience.

2) Get a kick out of body modification

The muscle training that comes with repeated anal stretching will eventually leave your anus looking a little different to how it was before you began. Some people get a kick out of seeing this change and you might too.

3) Explore fantastical dildos

Stretching your anus opens opportunities that are literally out of this world. Ever wondered what it would be like to be penetrated by a dragon? An alien or unicorn? Maybe even a creature with tentacles. If so, you aren’t alone.

Stretching your anus makes being penetrated by larger, more unusual objects more enjoyable. You may be surprised at how creative dildos get. Perhaps you can try a few once you have succeeded in your anal stretching mission.


Anal sex myths

There are many myths out there that put even the most adventurous people off trying anal sex. We are here to dispel those myths and relieve some of the concerns that might be holding you back from exploration.

Myth one: Anal sex hurts

If anal sex were painful, it wouldn't be as popular as it is. Pain during any kind of sex is an indicator that something is wrong. If you have tried this type of sex in the past and found it painful, there could be a couple of reasons why including:

1) Not enough foreplay

2) Not enough lubricant

The anus is tighter than the vagina, so it requires more care when starting out. Start small and work up to prevent pain and increase pleasure.

The more aroused you become, the less likely you are to feel pain during play. While a lot of lubrication is recommended, we don't recommend using any desensitising or numbing lubricants. Numbing agents may help you get through an anal session, but if damage is caused during play, you will definitely feel it once the numbing lubricant has worn off. Not to mention that, when done correctly, you will want to feel as much as you can.

Myth two: Anal sex stretches your anus

A lot of people are worried that regular anal sex will result in a stretched-out anus and even cause trouble in the bathroom. While regular anal play can result in a more relaxed anus, it won’t be to the extent that there will be any functional change to digestion or defecation. Your anus will go back to its usual shape and size post-penetration.

Myth three: You don’t need to use a condom

Some of the allure of anal sex is that belief that you can't get pregnant. However, that is not 100% true. Depending on where your partner ejaculates and how you clean up afterwards, there is still a risk of getting pregnant. While the chances are a lot smaller than if you were to have vaginal sex without a condom, we recommend wearing one. Better safe than sorry!

Additionally, anal sex brings with it the risk of an STI or STD. While the risk of a sexually transmitted disease is about the same as having vaginal sex without a condom, you wouldn't want to take any chances.

The great news is that using a condom may make for a smoother ride. Don't forget always to change your condom if moving from anal sex to vaginal or vice versa.

Before you go down the anal sex route, you may want to explore anal stretching. Even after you can easily take a penis or dildo, you can continue pushing the boundaries with stretching for even larger toys.


How to stay safe

Ready to start toying with anal stretching? Not so fast! Here at UberKinky, we want you to stay as safe as possible. If you follow our advice, you'll be well on your way to outstanding anal accomplishments.

If done carefully, the process of anal stretching should be extremely pleasurable. Remember, if you experience excessive pain or bleeding, then you are getting a bit ahead of yourself.

Slow down. Safe and effective stretching takes time. The anus isn't self-lubricating, and the tissue is more sensitive and thinner; therefore, there is a risk of tearing that can result in infection and STIs.

Here are some dos and don't to be aware of before you start practising

Doc Johnson Butt Plug


  • Go to the toilet - before getting started
  • Douche/enema - 3-4 hours before stretching
  • Start with fingers or a small, smooth butt plug - and always make sure it has a flared base
  • Use plenty of lubricants - it will make a difference
  • Sanitise stretching plugs before use
  • Speak to your doctor first - if you are pregnant, have haemorrhoids or are suffering from another condition that has an impact of your anus or rectum
  • Trim your fingernails - if you are going to use your fingers to practice


  • Force your stretching device in - if you are experiencing any severe discomfort or pain
  • Get overly excited - there’s no need for thrusting!
  • Keep going if there is pain or blood - stop when you feel discomfort
  • Overdo it - give your body time to recover between stretching sessions We recommend 2-3 days
  • Use a plug with a circumference greater than 4.5ins - when starting out
  • Use numbing lube - Pain is a sign you have gone too far and need to stop
  • Practice for more than 20 minutes - to start with

After a good anal stretching session, it takes about three to six hours for the anus to return to normal, so make sure you take it easy afterwards and give your body some much needed R&R.


What to use

For absolute beginners, we recommend using your, or your partners, fingers. Start with one and work up for an intriguing stretch. Once you have mastered all five fingers, consider moving up to bigger, more exciting, toys.

Whatever toy you opt for, remember not to be over-eager. You don’t want to get too ambitious too quickly, as this will increase the chances of injury.


Which lube to use may be the most critical question you'll ask yourself. The anus doesn't self-lubricate, so you must choose a good quality lubricant.

UberKinky recommends a water-based lube, as a silicone formula may not be compatible with your chosen toy, which we will talk about next. Because water-based lubricants often dry out quickly, really go to town on the application.

We also recommend a lube shooter, to ensure the inside is as wet as your sphincter and toy.

Easy in anal dilators

The key is in the name. If you are graduating from your fingers, then an easy in anal dilator will be your new best friend. Not only will they slide in smoothly, but they are also a well-known tool for slowly training and stretching.

Opt for an anal dilator with a small hole in the tip, which will help reduce internal pressure thanks to the toy's hollow centre. Make sure you choose a pack that comes with multiple dilators of increasing size.

Butt plugs

A good butt plug has an exciting narrow tip that teasingly increases in size before tapering down at the bottom until finally reaching a flared base. The flare at the end of the toy is essential, as it is what stops the toy from being sucked in too far.

With the variety of butt plugs available, you may feel a little frazzled when trying to choose one for your anal training. While we want you to experiment with a variety of plugs to find the one that gets you going, when it comes to anal stretching, we recommend a beginner's anal training kit so you can start smaller and work your way up.

Once you’ve mastered your craft, you can always explore some of our quirkier butt plugs.

Anal stretching rings

These are specially designed to stay in place, perfect for this type of play. We've heard that customers have had some great success with anal stretching rings. One customer told us that he graduated from a medium ring to an extra-large in just two months.


Now we are moving on to the big kahuna. If you've worked your way up through the previous toys mentioned in this guide, then we would guess that you have discovered the delights of anal training.

Are you ready to kick things up another notch? Dildos come in a range of designs, from ‘real feel’ to fantastic, there is even a kit to clone your partner’s penis if you want to train your bum especially for him.

There are even models designed explicitly for depth training if you fancy killing two-birds with one stone and taking your anal training to a new height.

When you are comfortable taking a regular dildo, you can move on to more exotic models, like an alien or tentacle. You will be surprised at the world of options available.

A note on materials

The material of the toy you choose may be the last thing on your mind. But it shouldn’t be. Silicone-based toys are often the most popular choice because they are durable, realistic and bendy. However, they are often more pricey.

The critical thing to remember is to make sure the materials of your toy, your condom and your lube don't negatively interact with one another and that the chemical makeup of the toy isn't hazardous to the human body.


The anal stretch procedure

So, your bum is ready for the BIG time? Great! To prepare for any anal encounter, including stretching, there’s always some preparation involved. Firstly, have a satisfying poo to empty yourself out. Getting your daily recommended intake of fibre should make this easy to do.

After this, give yourself a deep clean with a good douche or enema. You must take your time with this. Make sure the water temperature is at a comfortable level and be prepared to do at least two or three big cycles. For more information about douching/enemas, check out our beginner's guide.

As with any training session, you must warm up first:

1) When you are nice and relaxed (we recommend foreplay), start by massaging your anus with a lubricated little finger

2) When ready, try inserting your little finger into your anus

3) Slowly move it in a circular motion

4) Is it comfortable so far? If so, try to stretch your anus with your finger gently

5) Gradually work your way up to five fingers with multiple sessions

OK, now you’re ready for action! Make sure you start with a small, tapered butt plug. Don’t forget to apply plenty of lubricant throughout this process.

6) Insert the lubricated butt plug by pushing it against your anus with minimal pressure

7) Try inserting the device until it starts to feel uncomfortable or for around 3-4 minutes. There may naturally be some resistance. When this happens, remove the plug gently and then try again

8) Repeat until you’ve gobbled the butt plug up whole

9) Once you are comfortable with taking a butt plug of this size, level up and repeat until you have that gaping hole you’re after

Tip: When practising, insert your toy to the point where you feel internal pressure. Leave it there to rest while you do other things to stay relaxed.

After a little time, you can try and go a little deeper, so long as you don't feel any pain. If there is, simply return to the original position and gently wiggle the toy for additional pleasure.



The most obvious thing to do after an anal training session is to sterilise any toys you have used. The toy should come with care information, but if it doesn't, clean your toy with warm soapy water. Good toy hygiene is essential to prevent bacteria growth and transfer.

After a quick shower to wash off any faecal matter, bacteria and excess lube, it's time for some R&R, just like you would after any other hardcore training session.

We recommend a warm, luxurious bath and a good soak. If you are feeling any soreness following your session, try adding some Epsom salt to your bath. If you find that you're sore for more than a day or two, back off the training for a while to give your bum time to recover. You can dive right back in a few days after the soreness has receded but always remember to go slow.

You may experience a bout of gassiness after a good session, as well as the need to use the bathroom more than usual. Don't worry, though; this will soon go away. As you get deeper into your training, you'll get to know your body better and will be able to read the signs of when may or may not be a good day to train.


Potential risks

While we want to get you excited about training your rectum, UberKinky always strives towards safe play, and there are a few things you need to be aware of to ensure your private fun stays fun.

Throughout your training sessions, keep an eye out for the following:

Anal fissure - this translates to the lining of your anus or anal canal tearing. You will be able to see this if it occurs and may also experience pain, constipation, bleeding and smelly discharge

Perforation - this is essentially a hole where it shouldn’t be. It is extremely rare but can still happen

Haemorrhoid - which is a swollen vein either in your lower rectum or your anus. It can result in swelling, bleeding, itching, difficulty defecating and pain

So long as you take things slowly, aren’t too aggressive in your mission and pay close attention to what your body is telling you, the risks should be minimal.

So, what are you waiting for? Go forth and stretch!



Our Best Selling
Butt Plugs

Well, now you’re in the know! But how do you choose the perfect plug to assist you in your mission? Relax, UberKinky friends; we come bearing answers!

We’re not ones for anal abstinence here at UberKinky, so we were happy to engage in a little experiment to find the best stretching devices for your back door pleasure. We want you to go out there and grab your anal aspirations by the cheeks. So, we recommend opening yourself up to a new world of possibilities with one of the following three products;

Doc Johnson Classic Butt Plug

1. Doc Johnson Classic Butt Plug

“Feels really horny, especially when walking or bending. I kept it in for hours until it decided to come out on its own. Now need the large size!!!” Doc Johnson Classic Butt Plug

MEO 24/7 Anal Stretching Ring

2. MEO 24/7 Anal Stretching Ring

“Amazing. These are the best butt plugs I've ever bought. These plugs really do what the name suggests and will stretch you out quite quickly. In two months I've gone from medium to the XL and now when I pull the XL out my hole gapes like Goatse. It's also amazing how quickly my hole opens up on its own now because of these stretching rings.” MEO 24/7 Anal Stretching Ring

Easy In Anal Dilators

3. Easy In Anal Dilators

“Easy to insert and brilliant for slowly training and stretching. The dilators are made from hard, smooth plastic and are hollow. The tiny little hole on the tip is a clever innovation that helps reduce internal pressures.” Easy In Anal Dilators

Shop Our Entire Range of Plugs/Rings

Which Lube To Use?

This may be the most important question you ever ask yourself! Lubricant is an essential accompaniment to any anal play, but it is particularly important for this sort of endeavour.

Don’t forget, the rectum does not self lubricate so it’s imperative that you choose a good quality lubricant from our collection. Use a lube shooter to insert some lube into your rectum and then lube up your sphincter and toy.

UberKinky recommends a water based lube, as a silicone formula may not be compatible with your chosen toy. Make sure you reapply as necessary; water lube often dries out quite quickly. We recommend drenching yourself in one of the following;

  1. Uberkinky Smooth Move Waterbased Lubricant 250ml
    Uberkinky Smooth Move Waterbased Lubricant 250ml 14 4.4 5 1
  2. MEO Very Deep Urethral Lubricant 30ml
    MEO Very Deep Urethral Lubricant 30ml 56 4.8 5 1
  3. Uberkinky Cum Together Cum Lubricant 250ml
    Uberkinky Cum Together Cum Lubricant 250ml 21 4.5 5 1
  4. Smooth Move Lubricant 100ml
    Smooth Move Lubricant 100ml 12 4.5 5 1

So there you have it, the UberKinky Guide to Anal Stretching. Before long you'll be a butt plug size queen with a big floppy anus! Just remember the cardinal rules for safety: lubricate, go slow and stop if you see blood.

Doc Johnson Butt Plug