Comprehensive Anal Stretching Guide – How to Size Up for

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If your bum is just a beginner, and anything larger than a finger makes you run away screaming, this guide might not be for you. But if the idea of playing with large anal toys is a turn-on, then learning about intermediate to advanced anal stretching (also called anal training) will be very helpful.

However, if you’re just curious (and still don’t want to experience it), this is a safe space for educational reading. Everyone is welcome here!

In this article, we’re going to cover why people love intense anal play, how to prepare yourself, what are some of the best anal lubes, safety tips, frequently asked questions, and other useful/vital info to help you achieve your sizing goals. So, let’s dive in!

Note: Nobody here is a doctor. So take all of this as general suggestions and not step-by-step dogma.

What is Anal Stretching & Why?

Advanced anal stretching or extreme anal training are exercises and techniques that help experienced players take on large or even huge anal toys, prepare for more intense pegging, use prostate massagers more effectively, and/or enjoy “gaping” (where after or during play they can see the anus stretched wide open. You will see plenty of examples of this in porn or through the hashtag HoleGoals.

As for why people like this? It’s no different than any other anal play. The area around your bum hole has lots of nerve endings – just like our other erogenous zones. The simple act of rimming (oral pleasure around the outside of an anus) can be quite thrilling. So we just take this idea and ramp it up to sizes that will sometimes boggle people’s minds.

Here’s a video from the famous Dr. Lindsey Doe to start us off.

How to Prepare for Expansion

As you can see from the video, advanced anal stretching is NOT something that can be done quickly. It takes time, patience, and the desire to experience the entire pleasurable journey.

When it comes to preparation, the first stage is about research. Because, by now, you should already be well past the basics. At this point, there are new obstacles or things to keep in mind.

• What is the estimated timeline of your stretching goal? Which is obviously adjustable.
• How much time in one day or throughout the week can you dedicate to practice?
• What new toys or devices do you want to start incorporating (and are they safe)?
• Do you want to do this solo or with another person(s)?
• What are your “sensory” goals“? Things like pure sexual excitement, power exchange, etc.
• If you are going to be douching or light enemas more often? Are there extra health concerns or steps you need to take to stay safe?
• Do you need to change your anal lube to a different brand that’s targeted to larger insertions?
• Are your supporters a healthy influence?
• Is your sex toy hygiene up to scratch?

NOTE: Preparation at this stage should involve lots of planning and self-awareness.

Why Sex Lube is Important!

Normally, with any anal play, you’ll be using a lot of lube. But with large toys or fisting etc., you’ll need MORE … like A LOT more – ocean’s worth. But which anal lubes are going to get the job done the right way – and there are a ton of them on the market to suit any preference. Here’s the conundrum…

• Water-based is the safest for most sex toys, but it absorbs into the body faster. This means you’ll have to take the toy out and reapply far more often.
• Silicone will go much further but it cannot, repeat CANNOT, be used with silicone toys. Even the ones that are meant specifically for anal play. The lube will degrade the toy. I experienced this firsthand when I accidentally used the wrong bottle. It was like trying to clean up the worst kind of sticker glue that just wouldn’t go away.
• Oil-based is the magic potion for advanced anal play. I’ve even seen sex shops sell Crisco lard as a lube.
• Powders that you add water that creates a sort of “slime“, which is also another ideal product for these sessions. But I haven’t used them so I don’t know how they affect toys.

With all these choices out there, which one is best? In my opinion, the best anal lubes are ones that are long-lasting, aren’t tacky/sticky in texture, and won’t hurt your rubber/TPE, silicone, or other soft-textured sex toys. Unless, of course, you’re using medical-grade steel, then you’ll have more choices.

Here are some well-known and customer-approved examples…

• Pjur Power Premium Cream
• Swiss Navy Grease
• SKYN All Night Long Silicone
• Sliquid Silver Silicone
• Master Series Invade Deep Fisting Cream
• J-Lube or J-Jelly
• Anything from Boy Butter

How to Anal Stretch Safely Using With Big Objects

If you have your eye on that traffic cone sitting on the top shelf of your local sex shop, remember … it’s going to take you a while to get there. In a sense, you’re sharing similar steps to beginner anal players, but without the freaked-out feelings that come with inexperience. You’ll be stretching gradually over months. It’s a marathon, not a race.

As for which methods you want to try – like adjustable anal rings, medical-looking tools, larger anal trainers or butt plugs, or dildos – it doesn’t matter. Dealer’s choice. But there are anal sex toy considerations you need to keep in mind (which we will cover later in this article).

Prepare Your Materials

Gather all your toys, lubes, cleaning supplies, materials, and the protective layer you’ll sit or lay on. Have them close at hand (or in whatever spot you need). You don’t want to have to stop and go get something in the middle of your session. By now, it will probably be quick for you to make a checklist for those forgetful days.

Some suggestions for what you can use to protect your bedding, furniture, or carpet:

• Latex or rubber sex sheets
• XL doggie bathroom pads
• A couple of towels
• An old, but clean, bedsheet
• Even a shower curtain

Prepare Your Body & Mind

At this stage in your journey, you’ve probably mastered your relaxation and breathing techniques. But it’s still a good reminder that any anal basics are always used during anal play. We will go slowly, take relaxing breaths, etc.

You can have a warm bath or shower, prepare any visual/audio stimulations you might need, have your room temperature and environment the way you prefer, and make sure you won’t be interrupted. Or, if there’s the off chance an Amazon package will arrive early/late, have a bathrobe close at hand.

Lube Like Hell

Again, this isn’t a surprise, but on this blog, we love to beat the poor “safety horse” to death. Sizing up needs a ridiculous amount of anal lube. Apply it to the toy, hands, orifice, etc.

Also, there are sex lube injectors or lube dispensers to make things easier. Keep in mind that the dispensers can only handle normal silicone or water-based lube. Oils, certain gels, or creams might gunk up the lines. If you want to buy one, do extensive research to make sure they’re compatible.

Assume the Position

Everyone has a few positions they prefer during anal sex. But anal stretching might have different ones. And, as you go up in size, you might need to alter your position. Whatever you choose, it should be something comfortable that you can maintain comfortably for your entire session. And yes, changing in the middle is 100% okay. Do what you need to do.

It’s Training, Not Thrusting

Remember, whatever items you’re using, the intent is to gently stretch the area to train it. Even if you’re using a dildo, the idea is NOT to use any deep thrusting techniques. Granted, yes you’ll have to move and adjust your toy to get it in and find a comfortable spot. However, this isn’t the same as anal sex with large sex toys.

Use The Sphincter Trick

If you didn’t know this, actually pushing your sphincter during toy insertion (as opposed to puckering or tensing) can help things go smoother.

Stepping Up In Size

Differences in circumference (even length) should be incremental. Once the toy you’re playing with is mastered and becomes very easy to insert, then you can choose the next size up. Don’t be size greedy though. As for how long it takes, that’s totally different for each person. So never compare what other people use – especially porn stars.

Play the Waiting Game

Your sizing should be more about relaxing with the toy inside you for the allotted time. Just let it sit there and let your anal muscles get used to things. And, if you become uncomfortable, it’s okay to stop sooner than expected.

How To Clean Up

The order you do this is up to you, but generally, I find this is the best way. Mostly because you want to clean up your body so you don’t make tiny messes as you’re going about the rest of your cleaning process.

Wash Yourself

Wash your hands properly with antibacterial soap, have a shower (or just wipe if that’s all you need). Pay particular attention to under your fingernails, and if you have a vagina, make sure there has been no accidental leaks or cross-pollination that could cause an infection don’t the line. A thorough cleaning will also help refresh you and give you a moment to mentally transition out of your bum-related headspace.

It’s also worth noting that aftercare is a valid addition if you need it.

Clean Up Any Accidents

Let’s be realistic. No matter how careful you are, the more anal stuff you do, there’s always the chance that some of your bowels will come out to say hello. It’s just our bodies and nothing to be ashamed of.

Now, even if you’re hands have been cleaned well, you might need or want to put on latex or washing gloves to clean up, deal with your protective sheet layer, and clean your surrounding area (like where you had all your materials waiting on stand by. Use whatever cleaning aids you feel are best in that situation. It could be quick. You might have to deal with some spot stains. Or you could feel more clean by using a disinfecting cleaning spray.

Opening windows, lighting a scented candle, or spraying room deodorizers are also helpful if you don’t like the after-scent of your session.

Clean Your Toys

Properly cleaning any sex toy means you first give it a proper rinse or whip-down to get the excess off (including lube). Then (based on the manufacturer’s suggestions) use whatever cleaning solutions to sterilize your toy.

It could include antibacterial soap, washing a it couple of times, spraying with disinfectant (useful for metal toys), putting them in the dishwasher or hot water (if you can), or using a 10% bleach solution. How well you can do it depends on the toy material. Oh, and don’t forget any nooks and crannies!

After that, rinse them, and dry them thoroughly. On a clean towel sitting in sunlight is a great way to dry and disinfect. Finally, store your items properly. Your anal training toys should have their own baggies, boxes, containers, etc.

And, when you’re about to use the toys again, give them a light clean before use as well.

Warnings Vs. Side-Effects

PAIN or DISCOMFORT – Aggressive stretching and/or penetrations will result in pain and could possibly cause something larger than a micro tear – it could puncture through the membrane into other parts of the body (depending on the design of the toy, etc.) Being “sore” the next day isn’t always lumped in with “pain”, just FYI.

IRRITATIONS & ALLERGIES – This comes from using unsafe materials and/or not putting condoms over your toys when you play. Or, you could be allergic to the toy or even the condom you might have put over it.

INCONTINENCE – Yep, while your gape is going back down to normal size, there could be new messes. Give your body time.

ANAL FISSURES – An anal fissure is a small tear or crack in the lining of the anus. It can come from not only anal play, but constipation, or medial issues. The key to avoiding this is to not upsize too fast or big and use lots of lube. Also, cutting and filing your fingernails is a very good idea.

RECTAL PROLAPSE – A rectal prolapse is a condition where the rectum (the last part of the large intestine) slips or protrudes out of the anus. It can occur due to weakened pelvic muscles, chronic constipation, or physical strain.

When this happens, it can be a bit uncomfortable and may cause symptoms like pain, difficulty with bowel movements, or even some leakage. If you think you have one, go to the hospital! Better safe than shy.

SEXUAL INFECTIONS – If you partake in unprotected sex while pushing your anal boundaries, those tears increase the risk of infection through the roof.

Which Anal Sex Toys Are Safe for Stretching

• Dildos of any kind as long as they have a flared base and or narrow base neck to stop them from getting lots up your bum. There are some fantasy dildos out there for those who don’t want penis-looking ones.
• Vibrators are just buzzy dildos, so they’re good too if you want extra stimulation.
• Large anal trainer sets (also called anal dilators) are great and specifically designed for this stuff.
• Butt plugs are similar to trainers but come with more bells and whistles – like app control, vibrations, etc.
• Anal beads come in all shapes and measurements – even for size queens.
• Inflatable anal toys are useful as long as you’re careful.
• Anal speculums come in either medical styles or BDSM styles. Research best practices before using these.

Body-safe materials include silicone, proper glass, ABS plastic, sealed wood, and medical-grade stainless steel. Anything else will be porous and will hold on to bacteria no matter how hard you try to clean them. This comes with a downside – many of those materials are not flexible or squishy, which some people prefer or even need during large toy play. Silicone will give you the most flexibility. You’ll also need to make sure the texture isn’t rough.

There is TPE/TPR rubber. The upside? It’s softer. The downside? It’s quite porous. If you REALLY are determined to play with this material, put a condom over it!

Anything other than that, avoid it. The rest run the risk of having unsafe ingredients that could cause rashes, allergic reactions, or worse. The most prominent example is Jelly – stay the hell away from it.

FAQs About Getting a Bigger Bum Hole

Anal Stretching for Large Sex Toys – End Thoughts

What works for one person, might not work for another. That’s why advanced anal stretching or training should always involve careful experimentation and plenty of research. Some people report feeling a bit of an ache the next day. Some say it’s normal. Some don’t. But it really depends on the person. If an anal stretching master says their soreness is normal, that doesn’t mean the ach you feel is okay for you.

Be mindful of your body and visit a healthcare professional if you’re not sure.

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