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A Definitive Anal Stretching Guide for Absolute Beginners

anal stretching guide

A Definitive Anal Stretching Guide for Absolute Beginners

Here we go…anal sex. Does that jog up any “Oops! Wrong hole” experiences? See, when Mama Nature designed the female body, she gave it two things, a vagina that’s rough tough and durable, and, well…the rectum. She might have worked on a different set of blueprints with the human rectum, but don’t let that scare you.

The anus is full of nerve endings that, if anything, make anal sex just as (if not more) fun as vaginal sex. Sure, the rectum may not stretch and lubricate like its pleasurable counterpart, but with a little bit of practice on positions, tons of lube, toys and a few techniques, you’ll be shaking and ready to gobble up all the rest of the content on this site.


Getting the facts right

“But the rectum isn’t meant for that…”

Well… sure, the anal muscles are not adapted to having incoming objects. Nevertheless, when you think about it, it really fits objects larger than the average penis on an everyday basis. And along with the fact that the muscles can be trained to yield either way, learning the art of anal sex is almost purely psychological. This is more the reason why anal preparation should be a solo act, as we’ll discuss later.

Just to be clear before we delve further into this, in case you were wondering, you WON’T stretch out. And yes, regardless of size.

I don’t know about your personal porn tastes, but what I do know is that anal fisting is a whole category with thousands, if not millions of videos. This just goes to show you how much our buttholes can stretch.

But, chances are that you’re here as a newbie so I wouldn’t recommend this, at least not now. Long story short, our asses have muscles that bounce right back to their original states. After all, that’s their number one priority after your daily number two appointment.

anal stretching guide

The science behind your anal anatomy

The average human has two anal muscles, also known as sphincters that surround the anal opening. The external sphincter is voluntarily controllable, i.e. it can be tensed or relaxed at will. The internal sphincter, however, is controlled by the autonomic nervous system, the system that also controls functions like breathing and often reacts reflexively.

These two overlapping gatekeepers work together to make your bowel movements as easy as possible.

This article wouldn’t be complete without talking about the pubococcygeus muscles (let’s call them PC muscles for sanity purposes). They support the area between the anus and genitals and are also contribute to sexual sensation. 

“There’s a lot of muscles down there. How am I supposed to know which ones they are?”

It’s quite simple. Pretend as if you’re peeing and try to stop the flow of urine. See that muscle that just moved towards your vagina/penis? Not sure yet? You can also do it again and try to feel the muscle with your finger around the perineum (area between your anus and vagina/penis). Contraction and relaxation of these muscles will help you get control of your sphincters.

Here’s a quick Kegel exercise to guide you:

  • Take a deep breath and pretend you’re sucking in water inside your vagina and anus. Hold your breath for a few seconds.
  • Exhale and bear down, pushing out the imaginary water. Repeat again. For the best results, try this ten to thirty times each day.

This is just a simple exercise out of the many that will help you know how to control your PC muscles. Regardless of this exercise, moving your body while doing Kegel exercises is highly recommended. Kegel balls will also make the process much effective. 

Try combining them with walking, or running or while simulating a hula-hoop motion. I hope that now we’re all caught up on the biological aspect, can we please get straight to the fun part?

Warming up

It’s best if you get to warm up to butt play alone.

Why? you may ask.

Think about it this way. Exploration is key to discovering what works and what doesn’t work for you before you try it out with your partner. Moreover, you shoyuldn’t be under pressure to please your partner. Your speed, your rules, your orgasms. It’s all about you.

Here’s a quick checklist to consider before you start:

  • Take care of any bowel movements before you start. Stool stored in the rectum may hinder your progress because toys can only go so far before causing discomfort. It’s also a way of avoiding any messiness that might come with the experience
  • Hygiene is paramount. Take a shower or give yourself an enema beforehand. Showers help the body relax as well as making sure the butt is nice and clean for fun.
  • How long are your nails? Unlike the vagina, the rectal tissue is very soft and can tear easily. Trim your nails and make sure your hands are clean.
  • Get a handheld mirror, tons of lube, and a private place. Getting startled during anal play can be as painful as it is embarrassing. The internal sphincter we talked about earlier is quite sensitive. 
  • Relax and set the mood. You can play soothing music, light candles. Do what works for you. You can also try out PC muscle exercises to stimulate blood flow. This has been proven to increase sensitivity in the ass.

Stretching your anal opening

Lie on your back. Ensure you’re breathing comfortably. Massage and stroke your butt, inner thighs, and make your way to the area around your anus. How does it feel? How does your anal opening respond to the massage around it? Lube up your finger (pinkie recommended) but don’t immediately penetrate. It should feel good to stimulate the nerve endings in the area.

Apply pressure and rub around until you want more. Slowly insert your finger and explore your butt. Circular motions are recommended. Think of your finger as a rectal rover that explores your anus. Work your way from your pinkie to larger fingers over a period of time. Don’t rush, you’ll get to have it for the rest of your life after the intro so take your time. Still don’t trust your fingers can handle the job well? Let’s talk about toys. 

Using sex toys to stretch

Toys come in dozens of shapes and sizes for each stage of the anal journey, each with its own unique feeling. Finger play is recommended before toys for various reasons.

First, you need proper warming up. Toys don’t really give you the luxury of taking things at your speed as much as you want them to because they kind of dive right into it instead of giving you the much-needed comfort that comes with buildup.

anal stretching guide

Two, because unlike fingers, there are a lot to toys that we can’t fully discuss. However, don’t worry. This anal stretching guide includes the important bits so you won’t feel left out at all.

Three, charity begins at home. Fingers are readily available to most of us and you don’t have to wait for 3+ business days to start.

With toys, we cannot stress about size enough. Try out starter packs and work your way up the toy hierarchy. The graduation can be done over a span of days or weeks. This again isn’t entirely fixed since you can be content with a specific size and stick to it. However, for your safety, all anal toys should have a flared base. The last thing we want is getting a toy stuck in there. Some of us may want to go viral… but certainly not in this way.

Toy materials

It’s really important to consider the material that these toys are made up of. The most commonly used materials are:

  • Stainless steel is mainly a favorite for those into “temperature play.” It is the one of, if not the safest material out there. Contrary to what most people think, it doesn’t drag the skin. However, it is heavy and completely non-flexible. It is also the most expensive out of the three.
  • Silicone is body safe, most affordable, easy to clean, and flexible. It is totally recommended for beginners.
  • Crystal/glass is a go to for those into beauty and the aesthetic value of a product. However, do your research on the manufacturer’s credibility because these are highly fragile around the neck area and we all know what happens when you lose the base of a butt plug mid-session.

Butt toys design vs. functionality

So what are you all about when it comes to anal goals? Vibration? The pressure of a “full” feeling? In and out motion? :

  • Butt plugs. Less is more with this one. The basic design of a butt plug is to slide in and stay put. They are usually narrow at the top, thickest in the middle and narrow just above the base, which is flared. Imagine a not-so-sharp arrowhead with shoulders.

These are commendable for “pressure” lovers that don’t mind vaginal stimulation as a plus.

  • Anal beads are the highlight of most anal porn films. They are made of latex or hard plastic beads attached to a nylon string with a ring at the end. The most common beads are about half an inch in diameter.

However, these strings are somewhat difficult to clean, especially if they come in cotton, but you can use condoms as a quick solution.

  • Anal probes. This is what we’d recommend for newbies. It’s a long slim toy made of flexible rubber that vibrates.
  • Dildos are the most common toys out there and come in all colors shapes and sizes to suit every need. This mainly owes to the fact that most people also use them for vaginal penetration. However, we would highly recommend that you have a different toy for anal and vaginal penetration. Anal bacteria in the vagina are not something you need in your life.

We haven’t put vibrators in this list since most of the toys have variants with vibrators in them.


This anal stretching guide wouldn’t be complete without mentioning lubes. Whether you fancy a lube run being a quick trip to the kitchen or a drive to the local sex store, lube is mandatory. And please don’t assume anal mucous secretions are sufficient for anal play because it simply isn’t. Stick to these and you’re good to go:

  • Water-based lubes are what most professionals would recommend. They don’t cause irritation, they are odorless, easy to wash off and are used for vaginal penetration too. The most common one is K-Y liquid/jelly.
  • Desensitizing lubes numb the anus for “painless penetration.” I’m really not one to buy into the hype mainly because pain is the body’s natural way of telling you to stop. Without that, you’re prone to a lot of injury without realizing it.
  • Oil/Vegetable based lube. This category includes the most common household items like baby oil, olive oil, Vaseline, etc. These will not work with condoms and break down latex. However, if you’re not into beads I can’t really hold you back. In addition, note that some of these lubes offer conducive breeding grounds for bacteria and can lead to serious infections if they find their way to the vagina.

anal stretching guide


“If it hurts… you’re probably doing it wrong” – Jack Morin (author, Anal Pleasure and Health.)

Anal sex might not be the easiest conversation to have, but we have to admit, necessity is the mother of invention, and invent we have. The fact that anal sex is considered so taboo is more the reason why it’s so fun, from mind-blowing orgasms to immense pleasure words cannot express.

The possibilities of trying anal sex have been tried, tested, and proven throughout the years that date as early as the Greek civilization era. So why exactly does anal sex need to be so hard? Quick answer: it’s really not, once you get used to it. And that’s what this anal stretching guide is all about.

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