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The Beginner's Guide to Anal Stretching

by MISTRESS KAY
Published: AUGUST 31, 2018 | Updated: JULY 16, 2021
Presented by KINKLY SHOP
What, what? In the butt? Anal stretching is a key component of higher-level anal play - and it isn't as scary as it sounds.

If you're new to anal play, you might be thinking, "what?! Why would I want to stretch my butthole?!" We hear you. But anal stretching is actually a key component of most types of anal play - and it isn't nearly as scary as it sounds.

Technically, anal stretching is anything that gradually stretches the anus and allows you to insert toys (or a penis) that you couldn't comfortably take in the past. This means that it could technically apply to absolute beginners who've never tried anal experiences before; working up from a single finger to multiple fingers is a type of "anal stretching."

However, in the world of kinky sex, the term usually applies to stretching above and beyond the amount of stretching required for anal intercourse with an average penis, and training to take on large toys with diameters of over 2.5 inches. Anal stretching can go to extremes (including anal fisting and insertions of extremely large objects), but the anal stretching kink can also just be the enjoyment of the process of gently (and slowly!) training the butt.

Why Are People into Anal Stretching?

There are a couple of different reasons why people get into anal stretching. Of course, this isn't an exhaustive list, but it gives you a few ideas to familiarize yourself with the kink if you've never met someone who's into it:

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Body Modification

Some people initially get into anal stretching because of the opportunity to "modify" their bodies. As the butt is stretched out over time, the ring of the anus may start to look a bit different than an anus that's never explored anal sex. This isn't a bad thing - it's just a change in the body from repeated stretching and muscle training. People who enjoy body modification may be enjoying anal stretching with this "end goal" in mind. Expect people who love this aspect of anal stretching to show-off more photos of their bumhole - where the hole's outer ring may look puffier and thicker than the buttholes you might be familiar at looking at.

Fantastical Dildos

For others, it's the kinky idea of non-human dildos that gets them off. Maybe you've never even thought about it, but I bet a dragon would have a much larger penis than a human! Multiple manufacturers now provide some pretty wild, non-realistic dildo options, and people who want to play with fantasy creatures can now live the dream. Anal stretching can be used as a training tool, enabling people to take on their fantasy toy of choice.

(And hey, if you want to play with some fantasy sex toys without the thick diameter, the Cute Little Fuckers are a great option - especially the insertable Trinity!)

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Intense Sensations

As your body stretches out to accommodate something ever-so-slightly larger than your comfortable spot, it can feel physically intense. For some people, this intensity mentally translates into pleasure. For people on this side of the kink, the fun of anal stretching is all in the feeling of the stretching itself; it's all about that fullness and pushing oneself slightly beyond the point of complete comfort.

Anal Gaping

There's also a subset of people who absolutely love the look of anal gaping. In case you've never heard of it, "gaping" is exactly what it sounds like. After stretching, there may be a short period of time where the anus is wide open. Using large toys for extended periods of time can temporarily cause a gape after the user removes the toys. Don't worry - the gape usually goes away in less than a minute, and it's not a health concern! For those who love that little tiny experience of gaping, though, anal stretching can be one of the ways that they work themselves up to the toys that are large enough to allow them to gape.

An "End Goal" Penis

For some people, anal stretching is all about the end goal - which is a specific penis or dildo they want to use. Some people may not be into anal stretching for the kink aspects at all; they just want to use anal stretching as a process to help them take the larger insertable item that they're after. Especially for anyone who might be having intercourse with a partner with an extremely thick penis - or anyone who has a specific dildo that fits their fantasy that they really want to use - anal stretching can very well just be a means to an end.

So How Do I Stretch My Ass?

Anal stretching is surprisingly simple to get into. You just need toys, a serious amount of lubricant, and a good chunk of time and patience.

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Beware Anal Stretching Cream!

Whatever you do, do NOT pick up a tube of "Anal Ease" or any type of anal numbing cream. If you're stretching while everything is numb, you're missing out on the pleasure - and any potential warning signs, too. If things are so painful that you require numbing creams, you've gone much too far past your body's limits, and you need to dial it way back.

While I'd never recommend anal numbing cream for any type of sexual activity, it's especially dangerous with anal stretching: a kink where you're specifically trying to push your body's limitations. Anal play shouldn't be painful for most bodies. If it is, stop and figure out why!

The only time you should even think about a numbing cream is if you have an achy b-hole after an intense session and need some relief. A cool washcloth is a safer bet though then a chemical cream.

Read: Should We Talk About the Fact That Anal Sex Might Hurt?

Anal Stretching Toys

Anal stretching is one of those kinks where "one toy" likely won't be enough. (Good news if you love a good excuse for buying new body safe sex toys!) While there are definitely toys out there that would suffice as a "one and done" option for stretching, most people enjoy "sizing up" to a new toy once they've stretched themselves out to comfortably take their current toy. It's like a mini reward for themselves – and a physical reminder of their progress.

If you're in the market for toys, what should you look for?

The "All-in-One" Option

If you're on a limited budget or only want that "one and done" option, look for a toy that has an extremely tapered design - much like a "cone"-type design. The tip of your "one and done" toy will be extremely small while the base of the toy will be bigger than the tip many times over. You'll be able to insert this toy a little further each session, which will gradually stretch the body.

Keep in mind that this "one and done" option can make it easier to accidentally go a bit too far, and it also can be difficult to vigorously thrust without accidentally going that fourth-of-an-inch too far into painful territory. "One and done" toys are best for very calm, very relaxed sessions with very little movement.

The Odile Anal Dilator sits in its own category in between the All in One option and the Anal Stretching Kit. The unique device starts at a fairly manageable-for-beginners 1" diameter and gently twists open to widen in teeny-tiny increments to a respectable 1.5" diameter. The manufacturers say it is like 13 toys in one as it gives you so many options for girth.

Go for an Anal Stretching Kit

Especially if you're brand-new to anal (and using anal stretching to get to a point where you can comfortably use most sex toys), manufacturers have been providing everything you need - in a single kit! - for years now.

Anal stretching kits can vary in price - and in the toys included - depending on what you're looking to achieve. When considering an anal training kit, think about how (or if!) you can use those toys again in the future if you "progress" past them. Dildos in an anal stretching kit can be fantastic toys for strap-on sex - or they may be able to be sterilized and gifted to a close friend. Vibrating butt plugs may make great, casual, around-the-house toys for foreplay to help you "stretch out" for thicker toys as the main event. Get creative about how you think about anal stretching toy kits!

Think about how well that anal stretching kit fits in with your current stretching levels; ideally, you want the smallest toy in the kit to be exactly where you're at - while the largest toy will be near the "end goal" you have in mind.

Some anal stretching kits might include some fun extras too - like anal cleansing items or other anal accessories.

Read: How To Use an Anal Training Kit

DIY Anal Stretching Dildo Kits

If you're into the idea of multiple toys to assist you along your stretching journey, you'll find that your options, well, open up. As with any anal toy, you'll want your toy to have a great, big flared base. Because you want to train your body to take larger and larger toys, you might want to ensure the base is noticeably larger than the widest diameter of the toy - just to ensure the toy doesn't accidentally slide inside. Remember: Inserting toys without a wide enough base is how many people end up in the ER.

Once you've narrowed down your dildo options to those that include a flared base, your next step is to understand what size you can currently take. Measure the width of your current favorite dildo that you can use comfortably. If you don't have a dildo, measure the width of your current comfortable finger limit. From there, you'll likely want to find a toy that's one quarter inch (at the widest point) larger than your comfortable size.

Look for dildos that have a tapered tip - that is, the tip of the toy is smaller than the widest point of the toy. This will give you a comfortable way to penetrate yourself with the toy while going extremely slowly, over multiple sessions, to work yourself up to the largest point.

As always, please make sure to take sex toy materials into consideration as well. Silicone sex toys are the "gold standard" of stretchers, but if you're unable to afford the silicone toy you'd like, make sure your alternative is phthalate-free - and preferably cover it with a condom. (Go with the large-sized condoms if you need to!)

Outside of that, the rest of the dildo's features don't matter. Texture, color, design, vibrating features, and more are all up to you. Just keep in mind that certain materials and certain textures may require using a bit more lubricant than other textures and materials.

Read: 8 Ways to Figure Out Which Anal Toy is For You

What About Butt Plugs?

Butt plugs also have a place in an anal stretching repertoire. Any type of anal penetration can be helpful to anal stretching. However, not every type of anal toy is your best tool. That's where butt plugs lie.

While butt plugs are amazing for pleasure in general, most butt plugs are designed with a very small retention area - that area where your anal ring "rests" when the plug is inserted fully into the body. The point of stretching is to help the anal muscles gently relax and "stretch" during gradual penetration. Because most plugs only stretch while they are being inserted, they aren't the best toy for active stretching sessions - because the "set it and forget it" design of anal butt plugs don't continually stretch the butt.

However, all is not lost! If you're hoping to use an anal plug for stretching purposes, choose your plug with care. The "retention area" (the part of the toy that sits just inside the body after it has been inserted) should be similar in size to the body of the plug itself. As narrow retention areas are what allow plugs to stay in more securely, expect your stretching butt plug to slide out more easily than most butt plugs. (This will not usually be a great public play butt plug.)

Beginner Tips for Anal Stretching

  • Anal stretching begins just like any type of anal activity. Before getting into this activity especially named for "stretching" your limits, it's important to know the basics of your body - and how it reacts to anal play. Learn how to comfortably insert toys, and learn how your body feels about all of the various anal pleasure sensations. For some, experiencing anal sensations in a sexual manner is an entirely different, new thing to learn, and you want to have that aspect already completed long before you attempt any stretching. Know what feels good to your body - and what doesn't.
  • The biggest thing that separates "anal stretching" from straight-up "anal sex" is the speed you're inserting the item at. With regular anal sex, your body (and hole) are likely used to the size of the object you're taking, so you can slide in (and back out!) pretty easily. However, the point of stretching is for the toy to be ever-so-slightly-larger than you're used to taking, which means you need to take it slow. There's not going to be a whole lot of intense thrusting - at least when you begin. There may not even be any thrusting at all
  • Before you begin, I also want you to accept the fact that you may not get the entire toy inserted. You may not even get half of it inserted. That's okay - and that's part of anal stretching. You really need to accept this before you begin.

The "goal" isn't the base of the toy; the "goal" is feeling the pleasurable stretching sensations within your body - wherever that may be. (Sounds kinda yoga-y, doesn't it?)

Read: How to Use an Anal Dilator

How to Stretch Anally

Once you're familiar with your own body, it's time to get ready for your stretching session. Just like any type of solo sex play, you'll want to have everything as ready as possible before you begin. Gather a disposable pad to lay on (puppy pads are cheap and work great for this - a towel works great too), a washcloth or paper towels, the toys, and a bottle of lube. If you need any erotic content, get that set up too.

Now that you know the basics - and have everything prepped, let's go over how to stretch anally:

  1. Lubricant the toy.

  2. Then lube it again. Really. It's pretty hard to use too much lube. Lube is important for all types of anal play, but consider it the diamond necessity of anal stretching.

  3. Depending on how you like to do things, you might want to take this time to lubricate your butt as well. Get a bit of lube onto a finger and slide it into the body - and lubricate around the entrance as well.

  4. Press the tip of the toy against the butt. Take a few deep breaths here. Take a few more breaths. For the best "success", being fully relaxed and comfortable can make a huge difference.

  5. Slip the very tip of the toy into the body and pause. How does that feel? Reflect on how it all feels - and determine whether you want to continue or not.

  6. If you choose to continue, after another few breaths, slip the toy in a bit further. Take a few breaths to center yourself and really focus on the sensations your booty is feeling. If everything feels great, you can continue.

  7. Rinse and repeat.

For most people, there is a point where the sensations will stop feeling easily slidable - and will start feeling more like a pressure or sense of fullness. If you continue to insert past that point, the pressure and fullness will escalate until you likely hit the point where you start getting pain.

The "ideal" stopping point is when you start to feel that stretching and fullness sensation - but before you get anywhere near pain. You want your body to feel comfortably full and stretched, but any sign of gentle pain or sharp pain means you've likely gone too far.

If you're brand new to anal pleasure, where you start to feel pain can be surprisingly small! For some people, anything bigger than a single finger is going to start to set off the pain sensations - and that's totally normal! Just continue with the super-slender toys, continue stretching, and very, very gradually, you'll likely be able to play with larger items. For other absolute beginners, three fingers was totally a "go" on day 1 - and they only went up from there. It's really an anatomy-dependent thing, and it will really vary based on your own body. Isn't sex fun like that?

If you reach the base of the toy without ever feeling any sensation of fullness or stretching, the toy you're playing with might be too small to accomplish the "stretching" you're looking for.

Read: 3 Porn Stars Give Their Best Advice for Anal Sex

What To Do Once Your Anal Toy is Inserted

Feeling that sensation of fullness means that it's time to sit still - and let your body really adjust to the size. Don't try to insert it any further, and don't try to move it around too much. Sit and enjoy the sensations - or if you'd like to add something else, this can also be a great time to browse porn, use some kinky restraints to add sensations, read an adult book, masturbate, or watch something.

Once you've held that position for awhile and you feel like your body has adjusted, you can try to slide it in a little bit more. If you feel any pain, back right off and go back to where you were. But if your body feels that internal pressure again, go ahead and rest there. You'll just keep repeating this. Once your body doesn't seem to want to stretch anymore (as in, every one of your attempts to go a little deeper results in an "ouch!") or you want to be done with trying to stretch, you can do a couple of other things with the depth you've achieved before you pull out the toy.

One thing to do is wiggle the toy. It's not a particularly large or violent motion, but when your body is stretched to the limit, just a little bit of wiggling at the current spot is enough to feel pleasurable. Think about the amount of effort it takes your finger to scroll on your cell phone; we're talking that level of "wiggle". It's not much, but when your body is already stretched, it doesn't take much to add sensation.

Another option is to pull the toy out, and very slowly insert it back to the same depth where you had been. You'll want to go with very, very slow, gentle thrusts to avoid accidentally going that centimeter too far into pain, but a lot of people enjoy the gentle stretching of the anal ring as the toy lets them gently close up then stretches them open again.

And feel free to orgasm - or don't. It's up to you! You can move on to another sexual activity and orgasm, or you can just save up your sexual arousal for another time. Again, it's your sexuality, and you can play with it how you want!

After Anal Stretching

Depending on how long your session was and how stretched you are, be aware that there are a few after-affects of anal stretching.

Your body likely has a lot of lubricant and air in it, so expect some gassiness and a possible bowel movement when you're done. Depending on your body and how it reacts to stretching, you may also find that your body expresses the need for more bowel movements for the rest of the day - or maybe even a bit into the next day.

This is all temporary, and after doing stretching for awhile, you'll learn what toys tend to induce what "after effects" for you - so you can better plan around your schedule.

Your bum will also go back to its "normal" resting state after a bit, but since the muscles might be a bit more tired than usual, this is not the time to put on your glaringly white underwear and hope that a bit of used lube won't get onto it. It's possible your body might have a slight bit of lube leakage for a few hours afterwards - but it really depends on how "big" you were stretching that day.

Stretching Danger Signs

Like a lot of kinks - and especially with anything that pushes your body to new limits (such as weight training, yoga, or anything else), you can go too far with anal stretching.

The biggest risk is the same risk with heading into anal sex too quickly: the risk of microtears. Tears of the skin of the anus open your body up to the possibility of infection. Even if you thoroughly clean your toys and your own butt, bacteria can still easily slip into the body when there are open wounds in the skin.

The other large concern with anal stretching is the formation of hemorrhoids. Science agrees that anal sex itself isn't likely to cause hemorrhoids. What does cause hemorrhoids, however, is stretching of the anal muscle beyond its limitations - whether that's during regular anal sex, using your smallest toy, or the largest one you own. As the kink around "anal stretching" is the "stretching" part, it can be really easy for a lot of people to accidentally push into dangerous territory.

So what should you be looking for to avoid problems? The biggest one is sharp pain. Anytime during your playtime, if you feel sharp pain, you need to back off - NOW. If you back off and your body feels fine, you can continue - but be careful. If things still feel weird, you likely should call it the end of your session. Sharp pain is an important sign because it's your body's way of telling you something is wrong - and you definitely need to listen when it comes up. Stretching will definitely give you intense feelings of, well, stretching and internal fullness, but as soon as it hits sharp pain, you've gone too far.

The second-largest warning sign is long-lasting soreness. While a bit of residual soreness in the anal area is normal for a day or two after your play, anything past that means you've likely gone a bit too far with your body. Just back off for a couple weeks, give your body a bit of time to relax and, once the soreness is gone for a sustained period, you can start back into your stretching routine - but take it easy this time!

The last safety tip is this: don't go too quickly at first. With enough anal stretching, you'll learn how your body processes the sensation and the aftermath. From there, you can start to push near those limits. At first however, you have to give yourself time to learn what those limits are.

How Long Does It Take?

Anal stretching is not a fast kink. Don't expect to "see quick results in just two weeks!" Because many people enjoy the stretching itself in addition to the progress they're making, this doesn't bother a lot of people who love taking huge toys. However, if you're very goal-oriented, you're going to have to start putting things into a different perspective. Having a time frame and a goal in mind is more-likely to cause injury or frustration - and neither of those sound fun for sex!

Instead, accept that anal stretching is going to take a while to achieve. With practice sessions multiple times a week, you could potentially be switching to larger toys every month or so, but again, it really depends on your body, what toys you have, and what the various diameters of those toys are.

Is Stretching Permanent?

Typically, no. Like most things about the body, the body has a "set point" where it will gradually attempt to normalize itself. This means that if you take a break from your stretching, your body's ability to stretch will gradually decrease. Some people report seeing a noticeable loss of flexibility within as little as a week, but almost all stretchers will say they've noticed a difference within two or three.

This also means that, in case you were worried, you won't be "stretched out" for life. Your body's musculature will gradually tighten up again - especially if you help it out with doing regular kegel exercises.

Read: 10 Things to Know Before You Even Think About Fisting

What other training kinks are out there?

You're in luck! There are a few other similar kinks you might enjoy. In addition to anal stretching, a lot of anal aficionados enjoy anal depth training. While anal stretching is focused on inserting thicker objects, depth training focuses on inserting longer objects.

In addition, if you're someone who has a vagina, the same type of stretching can be done vaginally for vaginal stretching! Make sure any toy used for anal stretching has been sterilized before being used for vaginal stretching, but a similar process can be used with the vagina to stretch the vaginal walls, allowing you to take larger toys.

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Mistress Kay

Mistress Kay has a fondness for all things sexual. With a house that's quickly running out of room for all of her reading and vibrating pleasures, she spends her free time reading, writing, and learning about the sexual universe with her partners. She can be reached at Kinky World.

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