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The Complete Guide to Pain-Free Anal Sex

The Complete Guide to Pain-Free Anal Sex

Grab your lube and your notebook, you booty-curious lovers, this one is for you. 

Do you know the number one excuse for not engaging in booty play and anal sex is because of fear that it will hurt? Ok, maybe not the number one excuse, but it’s definitely up there, and honestly, it doesn’t have to be. 

Don’t take it from us, though, take it from Alex Hall, founder and host of The Bottom Digest, who is going to use all the space in this lil blog to explain exactly how to make booty play pleasurable and not painful. 

Why Does Anal Sex Get a Bad Reputation?

Let’s call it like it is: porn is the trickster of all tricksters. 

Thanks to movie magic, porn doesn’t show the prep that goes into sex - especially anal sex. It doesn’t show the stretching, the lube application, the deep breathing, and it definitely doesn’t show that porn stars spend more time preparing than an average person would for sex. It does, however, show someone taking a huge peen or toy in their booty, raw-dogging in doggy like it’s no biggie.

Since we didn’t get taught a whole lot about booty play at school, naturally, we turn to porn to educate ourselves and upon seeing a couple of vids, assume we can do the same as the porn stars. It's a huge problem because if you try booty play without warming up or lube, you’ll probably end up with anal fissures (tiny tears from friction and over-stretching), and that, queen, is your body screaming absolutely not.

Why Does Anal Sex Hurt? What Are the Most Common Causes?

If anal hurts, it’s usually one of these:

1. You didn’t stretch enough

This is the most common cause of pain and is because your anus needs a lot of warm-up time. Thankfully, we've got all the best ways to get ready over on our prep blog. The long and short of it, though, is that if you trained with small dilators (we’re talking finger size), and then, with no warning, tried to take someone with a final-dilator girth? You’ve got a one-way ticket to pain city.

2. You jumped sizes too fast

Patience, young horny grasshopper, going from dilator 3 to dilator 5 isn’t going to speed things up; it’s going to be more like skipping straight from “walk” to “double backflip.” No matter how much experience you’ve had, the booty does not approve.

The Fix: Always start with the smallest toy, check in, and move up slowly until the biggest size feels comfortable.

How Do Emotions and Stress Affect My Booty?

Ahhh, the old emotion and stress question. Firstly, great ask, this is a big question, with a big answer. 

Before you even think of getting into your bubble of relaxation, it’s important to hydrate. This is because your booty is a muscle, and like all muscles, it is much more flexible when hydrated. 

Speaking of relaxing, this is an important one because your anus has muscle memory, meaning it remembers the good and the “oh no” experiences. If you have experienced any anxiety surrounding booty play, chances are, you’re dealing with a very tightly closed door, so here are some strategies that can help:

  • Box breathing (your booty’s bestie)

  • Put on a sexy playlist and add some low lighting

  • Take a warm bath before play

  • Taking your time solo before introducing a partner

What Are the Best Positions for Comfortable Anal Sex?

Alex tells us he lives by a few rules when it comes to booty play. Firstly, breathing is the Beyoncé of anal sex. Your pelvic floor and diaphragm are best friends, so the more you can breathe, the more your pelvic floor will relax.

Second, always start on top.

That way, you control the depth of your partner, you control the speed, and you avoid accidental deep-thrust surprises (aka mood killers and booty hurters).

That’s why he suggests avoiding doggy until you’re really warmed up and familiar with your limits. Doggy is a move that can be really deep, fast and mostly just unforgiving. Remember what he said about your anus having muscle memory? Yeah, you’ll really upset that muscle memory if you don’t start on top. Seriously. 

So what positions should you choose? It all comes down to the curve of your partner’s penis or toy.

The curve determines whether you’re hitting:

  • A-zone (for folks with vaginas)

  • P-zone (for prostate owners)

Alex has this handy-dandy video to really help understand the nitty-gritty of it all! 

How Do I Make Anal Actually Pleasurable?

Before we get to the exciting lil moment of figuring out how to make anal sex feel pleasurable, let’s first talk about what anal sex actually is meant to feel like, and we’re going to bullet point it to keep it extra short n’ sweet: 

  • Full

  • Euphoric

  • Entire-body-shivering good

Now that that is out of the way, how do we make it feel like that? 

First of all, you’re going to need a lot of silicone lube (assuming you’re not allergic). You can use water-based lube, but honestly, steer clear as much as you can when it comes to backdoor play because it just gets soaked up by your booty and you need to reapply, reapply and reapply again. If you don’t, that’s when things get sore. If you do, you’ll go through a whole tube before you know it. 

Once you’ve got your silicone lube on hand, get some more. You can never have enough!

Along with the lube, you’ll need a pack of condoms. This is important; you always want to be safe, especially when it comes to booty play. If you are swapping between the anus and vagina, you need to change condoms; otherwise, you’re sending bacteria where it does not belong, and that’s a recipe for a UTI. Ouch.

What Are the Porn Myths We Need to Retire Immediately?

By now, you know Alex's (and GGO's) stance on porn: it’s entertainment, not education, and because of this, there are a few myths to bust that have been picked up throughout the years. 

They include: 

“Only gay men have anal.”

Absolutely not! This could be the biggest myth of all, and actually, any human with a butthole can enjoy anal. Period.

“It’s supposed to hurt the first few times.”

Nope. Pain simply means you didn’t warm up enough. Those anal sphincters need more stretching, baby. 

“Doggy is best.”

That’s a hard no. You might see it on porn all the time, but what you don’t see is the lube shooters that squirt lube into every nook and cranny so that sex looks effortless on camera. 

The reality is you’re not a porn star, and you need to start with positions that work for your body….and you need to apply lube as if your ass depends on it. 

“Spit works as lube.”

Please, do not, under any circumstances, supplement lube with split.

What Does My Man Need to Know Before We Have Anal Sex?

The number one rule before any sexual activity with a partner is communication. Encourage them to ask loads of questions along the way. 

Ask questions like:

  • “Need more lube?”

  • “Want me to go slower?”

  • “Do you want fingers first?”

  • “Are you ready for more?”

It’s also important to know that you need to be patient with each other. Booty play and anal sex is a process; it’s about warming up and getting comfortable with your body and each other. That’s the only way you’re going to have a good time. 

So, always avoid:

  • Skipping warm-up

  • Jamming anything in

  • Using spit

  • Assume you’re ready just because he is

What Are the Most Underrated Positions That Hit Really Good?

This all depends on:

  • How tight someone naturally is

  • The curve of the penis or toy

  • Angle of entry

So, here’s a video that will help you figure out what works best for you

Now What?

Repeat after us, anal sex doesn’t have to be painful, ever. With proper prep, lube, technique, breathing, and communication, anal can become a genuinely pleasurable, empowering part of your sex life. So take your time, listen to your body, and don’t let porn set your expectations. Your booty deserves better!

 

Lillie Rohan - Lifestyle and Entertainment Journalist

Lillie Rohan - Lifestyle and Entertainment Journalist

Hiiii queens!! I’m Lillie Rohan, your go-to sex and relationship expert. I have years of journalist experience, working with NZ Herald, Metro.co.uk, The Mirror & at one point, I even had a dating column… and podcast! Now I’m bringing you bi-weekly, well-researched yaps about everything you queens want to know about. Relationships, sex, dating, self-pleasure, all the questions you want to know but maybe don’t want to ask. It’s a vibe! x

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