BUTT SCHOOL Lesson No. 2. Anal Stretching

Gather round, students, for your education and entertainment. We’ve created an anal stretching guide, to you guessed it, help you learn how to stretch your anus. 

Before starting the anal stretching protocol, our good friend (not really) Dr. Goldstein recommends getting yourself an anal dilator or two. You can also purchase an anal dilation trainer kit (fancy), which usually comes with 3-4 sizes that increase in both length and girth. There’s some more product recommendations found later in the article.

Mid-year resolution, anyone? Here’s what to do.


Time and place is everything. Make it convenient and comfortable e.g. before or during a shower.


Use the smallest dilator first, with a significant amount of water or toy-approved lubrication. Our pal Euphemia Russell recommends
Sliquid Sassy, as it is water-based (so compatible with toys) but very thick. Ideal for toy focused butt play. Alternatively there are great local brands like Drip and Figr.

Just be sure to drown your hole and butt plug!


HOT TIP from Euphemia Russell pleasure coach guru:

Ensure your toys have a flared base of at least 5cm otherwise there’s the possibility of the toy disappearing into the rectum and then colon! This can lead to serious complications!


Over the course of 3-5 minutes, insert the dilator about 4-5cm into the anus, right beyond where the muscle lies.You’ll know when you get there. 


Set your expectations. It may take 4-6 times to insert the dilator, before the muscles feel fully relaxed.

Be gentle. If you experience resistance, pull the dilator out, re-lubricate, and do it again. Practice makes perfect. And practice takes patience. 

Slow and steady wins the race. Even if you’re feeling ambitious, start with the smallest dilator and use it consistently for a week or two, before graduating to the next size up. Repeat the same process over the subsequent weeks.

Remember, discomfort during the rectal dilation process is completely normal. What’s not normal is abnormal pain. Give yourself time and understand that mindfulness can help to contract or relax, just like any other muscle we have. It’s a learning process. If you’ve ever been with someone who can completely open their anus, it’s not necessarily due to looseness, but rather more about anal control. 

We spoke to our friend Caroline Moreau-Hammond from Becuming, the founder of a contemporary e-commerce sex store and brains behind the brilliant podcast The Philosophy of Sex.

“It’s important to note you have two sets of sphincters; internal and external. You have voluntary control over your external sphincters (which are around your asshole). However, the internal sphincters (which sit about 1-1.5 inches inside your rectum) can’t be voluntarily controlled. As a result, how your body responds to anal insertion may vary quite a bit from day to day. This means being patient and tripling the lube. 

When it comes to anal plugs, girth is an important consideration. For example, if you’re using a butt plug for anal training, pay attention to the width of the plug’s arm. This is as important as the size of the head of the plug. The wider arm, the more it will hold you open once it’s inserted. So if you’re starting out, look for something narrower. 


When it comes to anal dildos, materiality makes a big difference. The more rigid the material, like glass or steel, the less forgiving it will be. Hard materials are great once you’re familiar with stretching, but I usually don’t recommend them as a starting point. Super soft silicones from brands like Tantus and Fun Factory offer a lot of give and are great for beginners." 

Extra small: Snug Plug 1, Perfect Plug

Small: Bootie S, Limba S

Mediumish: Bootie M, Limba M, Bump

Medium: Amor, Swirl 

Large: Boss Stub, Bouncer, Twist 

Still sore?

Ok then. If your butt is still in a rut, feeling sore or tight, and you’ve tried all of the above, go and see a doctor. It’s always best to clear your mind of any doubt. Your butt is magical and you need to respect it and nurture it gently.