Anal sex

The Beginner’s Guide to Anal Stretching

Published: APRIL 6, 2023 | Updated: MAY 7, 2024
When done correctly, patiently, and safely, anal stretching will open you up to a whole new world of pleasurable possibilities. And that's what sex is all about!

If you're new to anal play, you might be staring at this article thinking, "What?! Why would I want to stretch my butthole?!" We hear you. But anal stretching is actually a key component of anal training -- 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) you couldn't comfortably take in the past. That means even absolute beginners, who've never tried anal before, can engage in anal stretching; working up from a single finger to multiple fingers counts!

However, in the world of kinky sex, the term "anal stretching" usually applies to stretching above and beyond the amount 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 inserting extremely large objects), but the anal stretching kink can also just be the enjoyment of the process of gently (and slowly!) training the butt.

With that said, here's the ultimate beginner's guide to anal stretching:


How to Anal Stretch

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

And, crucially, 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 well 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 limits. Anal play shouldn't be painful for most bodies. If it is, stop and figure out why!

READ: First-Time Anal Too Painful for Your Partner? Here's How to Help Them Enjoy It Next Time.

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. But even then, a cool washcloth is a safer bet than a chemical cream.


Now, ready to try anal training for yourself? Virtual high five! Here are the steps to follow:

1. Prepare for Anal Stretching

Preparing for anal stretching is a full, mind-body endeavour. Here's what you should gather:



  • A large chunk of interrupted time -- at least 45 minutes to an hour when you're first starting.
  • Forgiveness and patience for yourself. You can do serious damage if you try to go too fast. You may not even insert the toy fully -- and that's OK. If you're not ready to "fail" at inserting your toy today, you should probably wait for another day.


  • A disposable pad to lay on. (Puppy pads are cheap and work great for this -- a towel or sex blanket works great too)
  • A washcloth/paper towels.
  • Your toys.
  • A bottle of lube.
  • (Optional) Disposable gloves.
  • (Optional) Any porn/erotic content you like.
  • (Optional) Trimmed, filed and smooth fingernails.

2. Insert Your Toy(s)

Here are the steps to stretch your anus:

  1. Warm up in in whatever way is best for you. This might involve using slimmer toys to slowly prepare the area. This might involve using fingers. But whatever it involves, don't jump straight into inserting a three-inch-diameter beast of a toy; make sure your body is ready. (Some dilator kits, like this one, have hollow internal chambers you can use to slide extra lube inside your body to help with the "main event")
  2. Lubricate the stretching toy on which you want to focus today. Be sure you only use toys that are appropriate for anal play. It's very important that the toy has a flange/flared base or a handle to prevent it from escaping your grasp -- more about this shortly.
  3. Lube the toy 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 training.
  4. Lubricate your anus. 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 your finger and slide it into your body -- and lubricate around the entrance as well. If you're playing with a really thick, really long toy, you might take this time to use a lube shooter too.
  5. Press the tip of the toy against your anus. 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.
  6. Slip the very tip of the toy into the body. Pause. How does that feel? Reflect on the sensations and determine whether you want to continue or not.
  7. Take another few breaths. Seriously, there's no such thing as "too slow." Maybe this is where you stop today -- and that's fine!
  8. Slip the toy in a bit further. But only if you choose to continue. Take a few breaths to center yourself and really focus on the sensations your booty is feeling. If everything feels great, you can continue.
  9. Repeat Steps Seven and Eight until you've reached your physical or mental limit.

For most people, there is a point at which the sensations will stop feeling slippery and will start feeling more like pressure or a 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. Thus, our number one safety tip is this:


Don't go too quickly at first.

With enough anal stretching experience, you'll learn how your body processes the sensation and the aftermath. From there, you can start to push those limits. At first, however, you have to give yourself time to learn what those limits are.

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 pain means you've likely gone too far.

If you're brand-new to anal pleasure, the point at which you start to feel pain can be surprisingly early! For some people, anything bigger than a single finger will set off the pain receptors -- and that's totally normal! Just continue with the super-slender toys, continue your stretching sessions and, one day, you'll likely be able to play with larger items.

For other absolute beginners, three fingers will totally be a "go" on day one -- and they only move up from there. It's really an anatomy-dependent thing, and it will really vary based on your body. Isn't sex fun like that?

If you reach the base of your 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: The Ultimate Guide to Anal Masturbation

3. Focus and Readjust as Necessary

I really can't stress Step Seven in the list above enough.

Once your toy is, or your fingers are, in your anus and you're feeling that sensation of fullness, it's time to sit still and let your body adjust to the size.

Don't try to insert anything further; don't try to move your toy or fingers around too much. Sit and enjoy the sensations -- or, if you'd like to add something else, browse some porn, use some kinky restraints to add sensations, read erotica, or masturbate.

Once you've held that position for a while and you feel like your body has adjusted, you can try to slide your stretching implement 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. Just keep repeating this!

When you've reached the point at which 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 stretching for today, you can do a couple of other things with the depth you've achieved before you pull out the toy:

  1. Wiggle the toy around. This shouldn't be a particularly large or violent motion. But when your body is stretched to its limit, a bit of wiggling in the current spot can be enough to feel pleasurable. Think about the amount of effort it takes your finger to scroll on your 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.
  2. 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 an inch too far and feeling pain. But a lot of people enjoy the gentle stretching of the anal ring as they close up then stretch open again.
  3. 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!

There you have it: Rinse and repeat the steps above, and you've pretty much got anal training down. Now, if you're really interested in priming your booty for some penetrative action, there are some more things you should know:

Beginner Tips for Anal Stretching

Know What Feels Good to Your Body -- And What Doesn't

Anal stretching begins just like any type of anal activity. Before getting into this activity 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 completed long before you attempt any stretching.

Go Slow

The biggest thing that separates anal stretching from straight-up anal sex is the speed at which you're inserting the item. 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 out pretty easily. However, the point of stretching is for the toy to be ever-so-slightly larger than what you're used to taking, which means you need to take it slow. There won't be a whole lot of intense thrusting -- at least not when you begin. There may not even be any thrusting at all.

Don't Expect to Insert the Whole Toy

Before you begin, accept that you may not get the entire toy inserted. You may not even get half of it inserted. That's OK -- and that's part of anal stretching. Being "goal-oriented" is how you end up with injuries. Yes, injuries to your butthole. You want to avoid those.

The goal with anal stretching 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 Long Will Anal Stretching Take?

Anal stretching is not a fast kink. Don't expect to see "quick results in just two weeks"!

To give you a general timeframe, however:

  • If you're trying to do anal stretching to have anal intercourse with an average-sized biological penis, it can take two weeks to six months.
  • If you're trying to do anal stretching to take some of the larger fantasy dildos out there, you're looking at a timeframe of six months to multiple years.

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 timeframe and a goal in mind is more likely to cause injury or frustration -- and neither of those are 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 your toys' diameters.

Giving you an exact deadline isn't just counterproductive; it's dangerous. If you want to "be gaping by Valentine's Day," you're setting yourself up for injury.

Is Anal Stretching Safe?

Well, no...and yes.

Inserting anything into the anus comes with a risk. Microtears allow bacteria that can lead to an infection -- and not-so-micro tears can cause serious damage. Anal fissures and abscesses are very real.

That being said, like everything in the world of sex and kink, anal stretching is all about mitigating risk as much as possible. Large, firm poops can also cause microtears -- and almost all of us are presumably still doing that on a regular basis.

The biggest risk of responsible anal training is an anal fissure. This is a small tear in the thin skin that lines the entrance to your ass. It's relatively easy to tear (remember that thing about large poops?), but it's especially easy to tear if you're not using enough lube and inserting a sex toy that's too large.

To mitigate risk:

  • Don't use toys beyond your current level. This is about very, very, very slow stretching; if it's not taking you at least 10-15 minutes, you're going too fast.
  • Always warm up your butt. Start with smaller toys and slowly work your way towards the larger one(s) you plan to use for the bulk of your stretching session. Your body's ability to stretch can vary day-to-day; what was "easy" on Monday might be painful on Thursday.
  • Stop if anything feels "off." Sharp sensations, too much pressure, pinching, hyper-awareness of the entrance and pain are all signs you've gone too far or something is wrong. If you feel one of those, call off the stretching session entirely for the day.
  • Don't begin "stretching" in earnest until you're an avid anal player. If you haven't been enjoying anal for at least 6 months, you probably need more time in the "just have fun!" stages. Reducing your risk requires the ability to easily tell when something is off -- and if you're so new that everything feels unfamiliar, you're going to have a really hard time.
  • Have patience! Don't insert too quickly or apply so much pressure that your hole "gobbles up" a toy for which it wasn't ready.
  • Don't stretch if your butthole is sore or if you've seen blood in your stool within the last three weeks. It might have been too much anal sex, a stretching session too recently or simply a previous day where food didn't agree with you.
  • Use lots and lots of lube. Then use more lube. You can give yourself a bit of a lube enema, but that's about the biggest risk of over-using lube. The risks of under-using lube, however, are a lot more serious. Rule of thumb: If things aren't slipping and sliding like there's no tomorrow, you probably need more lube.

READ: The Best Kind of Lube for Every Sexual Scenario.

  • Develop healthy bowel movement habits. Both bowel movements and anal stretching stress the area. Reducing the stress you're placing on your butt for the non-kinky things can help reduce the likelihood of future problems. Follow standard "healthy bowel movement" recommendations, like a healthy diet (wherein you aim for Type 3 or Type 4 on the Bristol chart.) Drink lots of water, enjoy regular movement and talk to your healthcare provider if you have medical concerns that might make this difficult to achieve.
  • Don't stretch too often. Once or twice a week, especially when you're starting, is more than enough. You'll want to be able to recognize the signs and symptoms of too much anal play before you add in more sessions than that.
  • Ensure your toys are clean and free of any sharp edges. For the least transmission of bacteria possible, use a condom (if you can!) with your toys during play.
  • Don't participate in anal stretching if you don't have the ability or finances to seek medical care. If you end up with a serious issue, not seeking medical care can, quite literally, be fatal.
  • If you think you may have an anal fissure, stop all anal play and stretching! Try to orient your diet toward healthy bowel movements as much as possible. (If you're lactose-intolerant, for example, you might opt for dairy-free ice cream for a while.) Any expansion of the anus may re-tear the fissure and slow down healing, so remove all "optional" chances for that to happen.

If you're doing irresponsible anal stretching, your risks are even higher. Anal fissures can extend to the surrounding muscles in severe tears, and this may require surgery to fix. A larger anal fissure also requires longer healing time and offers more opportunity for infection. An anal infection can lead to a serious anal abscess, which will require a surgical incision and drainage and can lead to an anal fistula.

Really, and honestly: Fucking around with anal stretching and hurting yourself is no joke. You can do serious damage that will require medical intervention. Lucky for us, going super slow, being really patient and listening to your body can help reduce some of these risks. But anal play, in general, is not a zero-risk activity, and you should ensure you're doing everything you can to reduce the risk.

If you're uncomfortable with the risk entirely, remember: You don't have to do any anal stretching or anal play at all. This is not a requirement to enjoy yourself, and there are lots of other amazing sexual activities in which you can engage.

When Should I Size Up?

There are two main reasons you'll size up your anal toy:

  1. You can comfortably take the entire toy's size. If you're slipping your sex toy in within seconds, you're probably not "stretching" yourself all that much anymore. At this point, you might want to use a different, larger toy to continue stretching yourself out.
  2. You're just not into that toy anymore. Honestly, that's cool too! Sex is all about enjoying yourself, and if your current stretching toy is more "chore" than "pleasure," swap that shit! Find a new stretching toy that better fits your body and your goals. Identify what you didn't like about your current option before shopping for your new toy.

You might also choose to size down if your toy is too big. In that case, serious props to you for protecting your body and understanding yourself! Using a toy that's too big has a risk of hurting you -- and it honestly just isn't that productive to anal stretching! Swap down to a smaller toy to pick up your anal stretching journey right where you left off.

As you progress to larger and larger anal toys, you may need to switch out your toy not because it's too wide, but too long: Sometimes the width you want on your sex toy of choice is simply too far down on the shaft. Anal depth training and anal stretching are two different things.

But what if you just want to size up? That's OK too. Especially if you're using an anal stretching kit, there's likely some overlap between sizes. For example, the tip of your "medium" dildo might be about the same size as the base of your "small" dildo.

If you're at the point where you'd like to try to go up a size, have at it! Just make sure to use the same caution as you did when you first started anal stretching with a new toy: Use lots of lube, go very slowly and be willing and ready to abort at the first sign of sharpness, tightness or pain.

You might be ready for the next size. You might not. Making sure you're honest and realistic with yourself is the best way to avoid doing unintentional damage.

Is Anal Stretching Permanent?

Typically, no. Like most things about the body, there's a "set point" at which your body will gradually attempt to normalize. This means, if you take a break from 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 by doing regular kegel exercises.

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

Common Anal Stretching Struggles

What If I Can't Insert the Toy?

That's OK! Depending on the size of your anal training toy, you may not get it all the way in today, next week or the week after.

It's totally normal to only take a little bit of the toy at a time. You may only take the tip -- or maybe just the first third. There's a toy in my personal collection that's been in progress for the past year. We still haven't fully inserted the toy.

Think of it in a positive way: That toy is going to last you a long time, and you won't need to spend money as quickly on new toys!

READ: Yes, You Can Find Body-Safe, Affordable Sex Toys.

If the "features" you want to enjoy about the toy can only be accessed when it's fully inserted, consider buying a smaller version of a similar toy. That way you can still train safely, but you can also use the functionality for which you were excited.

What Do I Do After I Insert the Anal Stretching Toy?

Anal stretching is not always glamorous or exciting. Sometimes, you slide in a dildo, lay there for a half an hour while your body slowly acclimates to its size, and then go about your day. Honestly, it can be pretty darn boring sometimes.

However, it doesn't have to be. You can mix your anal training with anything you'd like. You could watch some of your favorite pornos while you stretch. You could use a butt plug for stretching and masturbate at the same time. You could turn the vibrations, or other functions, of your stretching toy on to pleasure yourself while anal stretching. You could, quite honestly, watch educational, non-sexual videos on YouTube or catch up on the latest episodes of your favorite TV show. It doesn't have to be a sexual, arousing time!

If you're going for arousal and orgasm while anal stretching, I only ask that you remember to be patient. When we're all horned up, it can be easy to go, "Fuck yeah, I'm getting this all the way in!" and you may not realize the damage you've done until you're cleaning up. If you keep your patience -- and your wits! -- about you while anal training, there's a whole world of things you can do while you stretch.

It's easiest to think about anal stretching the way you think about non-sexual stretching: Often, people who are trying to get their splits will simply hang out in their stretch while watching TV. You might end up treating anal training the same way too.

What If I See Blood After Anal Stretching?

If you see blood during play or while wiping up afterwards, it means you probably went too far. That's OK; It happens to newbies and it happens to practiced stretchers. Your toy might be too large; it might have caught a corner of your fingernail on the entrance; you may have been too rough.

READ: Bleeding During Sex? Here's What to Know.

If that's the case, stop your anal play for the day. Bleeding may happen, but it is always a sign that the body needs more support. So, go into "protect the butt" mode, which means no anal play and a healthier diet (to reduce the strain of bowel movements!). You'll likely find bleeding only occurs after bowel movements (if that) for the first couple of days, and you may not see blood at all within the week.

See your doctor if you're seeing blood after a few days or seeing large amounts of blood. ("Large amounts" are anything more than a speck or two after defecating.)

And in any case, wait at least two or three weeks before going back into anal play, if not more. Remember, patience is the name of the game here!

On this note, though, we should get into:

Anal Stretching Danger Signs

Like anything that pushes your body to new limits (like weight training, yoga, or any physical activity), you can go too far with anal stretching.

The biggest risk here is the same risk with heading into anal sex too quickly: Microtears. Microtears are tiny (micro) tears on the skin of your anus and can expose your body to the possibility of infection. Even if you thoroughly clean your toys and your butt, bacteria can still 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 the anal muscle beyond its limits -- whether that's during regular anal sex, using your smallest toy or using the largest one you own. Because the kink around "anal stretching" is the "stretching" part, it can be easy for people to accidentally push into dangerous territory.

So what should you be looking for to avoid problems?

Sharp Pain

If you feel sharp pain at any point during your playtime, 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.

Make sure you differentiate between feelings of stretching and internal fullness and pain. Fullness = OK; sharp pain = stop.

READ: Tips for Having Awesome - and Pain-Free - Hand Sex.

Long-Lasting Soreness

While a bit of residual soreness in the anal area is normal for a day or two after play, anything past that means you've likely gone a bit too far with your body. In this case, 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!

Anal Stretching After-Effects

Depending on how long your session was and how stretched you are, be aware of the following after-effects:


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 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 a while, you'll learn what toys tend to induce what "after-effects" for you so you can better plan around your schedule.

Lube Leakage

Your bum will 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 you won't leak lube onto it.

It's possible your body might have a bit of lube leakage for a few hours afterwards -- but it really depends on how "big" you were stretching that day.

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 tangible reminder of their progress.

Here are my recs for toy categories to explore if you're out to try anal stretching:

The "All-in-One" Option

The Odile Anal Dilator sits in its own category as an all-in-one anal stretching option. The unique device starts at a fairly-manageable-for-beginners one-inch diameter and gently twists open to widen in teeny, tiny increments to a respectable one-and-a-half-inch diameter. Essentially, this all-in-one toy lets you gradually stretch yourself at your own pace. You can do this in two ways:

  1. The twisting method. Odile's unique design lets you actively stretch while the toy is inserted. Slide it in at a comfortable girth and gently twist the key at the base to open it up a little bit. See how that feels and let your body acclimate. If it feels right, you can give the key another twist and expand yourself a little bit more. Keep going until you're done stretching.
  2. The dildo method. Pick the diameter that's right for your body and slide the Odile in. Not the right width? No problem; you can easily slide the toy out and readjust the diameter before reinserting it. You can also customize the Odile's diameter in one-millimeter increments anywhere between one inch and one and a half inches. That gives you a whole lot of options!

odile anal dilator

Odile Anal Dilator.

The Odile is just about the only toy on this list that allows you to explore both these stretching options -- so if you're after something that can do the job all on its own, it's probably your best bet.

Alternatively, if you need something thicker than the Odile can go, you might look for a toy with a tapered design -- much like a cone. This type of toy features an extremely small tip and an extremely wide base. You'll be able to insert this toy a little further each session, which will gradually stretch the body.

The b-Vibe mASSter's Degree Anal Set hollow cone up against a white background. It is made from a black, slightly see-through plastic. There are measurements along the entire length of the cone. | Kinkly ShopCone from the b-Vibe mASSter's degree kit for ultra-thick anal stretching.

Keep in mind that the cone-type "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.

Anal Stretching Kits

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 types of 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 also be fantastic toys for strap-on sex, like the Sportsheets Anal Explorer Kit, which comes with its own harness.

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 with how you think about the toys within your anal kits!

Also think about how well your 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 include fun extras like anal cleansing items or other anal accessories. The b-Vibe Anal Training Kit, for example, comes with an enema you can use to douche beforehand.

b-Vibe anal training kit.b-Vibe Anal Training Kit.

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, as mentioned earlier. 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, look for a toy that's one quarter inch (at the widest point) larger than your comfortable size.

Also look for options that have a tapered tip -- that is, wherein 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. An example of a tapered-tip toy is the XR Brands Thump-It -- notice how the tip of the toy is very slender compared to the base, allowing anyone inserting it to slowly work up to the thickest point.

XR Thump-It! Thumping Plug - Kinkly Shop XR Brands Thump-It.

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

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 most efficient tool.

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" throughout your play. Because the base of most plugs is one of the smallest points throughout the entire toy, most butt plugs only stretch while they are actively being inserted.

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.)

What to Consider When Choosing Anal Toys

Choosing toys for anal stretching is honestly pretty fun! Who doesn't like choosing new toys!?

There are some specific things you'll want to consider when choosing toys for anal stretching, though. Things like:


We're here to help slowly stretch the butt to accept larger and larger toys, so we need a toy that will be comfortable -- but a challenge -- in its thickness.

The exact diameter you need will vary based on where you are in your anal stretching journey and your goals. If a finger is already a challenge, something about finger-sized -- or slightly thicker -- might be in order. If you're taking fists, it's an entirely different conversation.

While selecting a toy for anal stretching, keep the design of the toy in mind as well. Ideally, you want to be able to "pause" at the thickest point of the toy.

For example, let's talk about a toy like the Blush Temptasia Bling:

Blush Temptasia Bling - Kinkly ShopBlush Temptasia Bling.

It's cheap; it's small; it's available in multiple colors. Seems like a good fit, right?

Not quite! If your end goal was efficient anal stretching, you'll want to pay attention to the physical size of the toy. The tapered tip is good. We want that! But right as the toy hits the widest part, it quickly shrinks down to almost nothing for the retention-area base.

This design makes sense for a butt plug. That super-duper-slim retention area is what rests in the entrance and keeps the butt plug nicely secured when you're walking around your house.

However, when you're doing anal stretching, it means that your butt isn't going to be all that stretched for long periods of time. You'll insert the plug, get a semi-good stretch as it slides in and, as soon as you hit the thickest point, the toy will slide all the way in to its very slender base. That base is so slim, it isn't really doing much "stretching" at the entrance! Anal beads have the same problem.

That's not to say you can't do anal stretching with plugs, anal beads or other toys like these. If these types of toys are what turn you on and make you enjoy anal stretching, do it. Remember: Everything about this is about your pleasure!

However, if you're looking for the most efficient and effective sex toy for anal stretching, plugs ain't it. Instead, pay attention to the diameter of the toy that hangs out at the entrance where our stretching is focused.

This means cone-like toys (like those found in the mASSter's Degree kit!) or dildos (like the Odile!) will be some of your most effective toys for anal stretching. Since those toys don't come down to a slender diameter, your entrance stays nicely stretched out.

Hollow Cone toy, as found in the b-Vibe mASSter's Degree Anal Set.

In a perfect world, you want a toy that has a tapered tip to help your body slowly take the increasing size that leads into a shaft that maintains a thicker diameter for constant pressure on the entrance.


As always, take sex toy materials into consideration as well.

While rubber, plastic, vinyl, and jelly toys will be cheaper, I recommend getting a silicone toy for anal stretching. That's because it can be near impossible to get the scent out of porous materials like rubber, vinyl or jelly. However, if you have a waterproof silicone toy, boiling or bleaching can help remove the scent. I'm not sure about you, but when my anal toy smells like poop, I really don't want to play with it all that much.

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 your toy'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.

One last thing re: toy shopping: The standard advice for buying anal toys still applies even though you're stretching. These articles make some fantastic points:

Anal Stretching Sex Positions

Patience is the name of the game when it comes to anal stretching. As such, any position you choose for anal stretching should be comfortable AF. You should be happy to lay there for at least an hour without muscles cramping or limbs going numb.

That means super easy sex positions win the "best anal stretching positions" race.

I'd recommend:

The From the Back Position

From the Back sex posiiton. A person is laying on the side with their knees pulled up towards their shoulders. They are reaching around behind them, from the back, to slide an anal toy into their butt. It looks like they're laying in the fetal position. | Kinkly

If your body and arms feel comfortable this way, the From the Back position has the added benefit of making it easier to hit the prostate (if you have one!).

The Hole Lot of Love Position

Hole Lot of Love sex position. A person straddles the sex furniture piece with a dildo held upright in the piece of furniture. They can now use the toy hands-free.

The "Hole Lot of Love" position uses the magic of sex furniture to make anal stretching hands-free. Simply slide your toy of choice into the sex furniture mount and then crouch on top of it (The Liberator Bon Bon or Tula is shown in the illustration.) This lets your hands wander for other activities and holds your sex toy more securely than a suction cup. The sex furniture's high-density foam also helps support your body, reducing the strain on the thighs.

With all of your body weight behind your movements, make sure to go slowly and pay attention to your knees to ensure you don't accidentally go too long.

The Synchronous Friction Position

If your partner has taken an interest in your anal stretching, the Synchronous Friction position is pretty much the perfect fit.

This angle is slightly awkward, making it difficult for your partner to get a little too enthusiastic and over-insert the toy. At the same time, if you're at a point in your anal stretching where the smallest centimeter is the difference between pain and pleasure, this mutual masturbation position lets your partner get a front-seat show without feeling pressured to participate.

READ: The Ultimate Guide to Mutual Masturbation.

The Legs in the Air Position

Depending on your proportions, this might be a bit of a stretch to use toys between your cheeks, but for people who can easily make the reach, this can be a preferred way to stretch.

Why Are People into Anal Stretching?

There are many 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:

READ: The Joy of Finding Your Fetish.

Body Modification

Some people initially get into anal stretching 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 asshole in which the hole's outer ring may look puffier and thicker than buttholes you might be used to seeing.

Fantastical Dildos

For others, it's the kinky idea of non-human dildos that gets them off. 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!)

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. Think about how nice it can feel when you take a non-sexual stretch into that "deliciously uncomfortable" zone.

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 they're after. Especially for anyone having intercourse with a partner with an extremely thick penis, or anyone who has a specific dildo they really want to use, anal stretching can be a means to an end.

What Other Training Kinks Are Out There?

Not into anal stretching? Tried it already and want something new? 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, which focuses on inserting longer objects instead of thicker ones.

In addition, if you have a vagina, the same type of stretching can be done vaginally for vaginal stretching! You can follow the same steps outlined for anal stretching to stretch the vaginal walls and allow you to take larger toys and fists. However, make sure any toy used for anal stretching has been sterilized before inserting it into a vagina.


Anal stretching is a journey. It's a very, very individual journey.

The body takes as long as the body takes, and we have to respect that. It sucks to be patient, but it sucks even more to tear your asshole. (Yes, you can tear it. Please, please don't. Not only does that leave you open for infection and make it easier to tear in the future, but it entirely derails your anal stretching routine.)

Luckily, though, bodies are incredible things! When done correctly, patiently, and safely, anal stretching will open you up to a whole new world of pleasurable possibilities. And isn't that what it's all about?

READ: A Step-By-Step Guide to Giving Your First Pegging.

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.

Latest Sex Positions