Avoiding Anal Sex Pain
First published November 28, 2019
© Max Private – All rights reserved

Feature image by Jerzy Górecki

Avoiding anal sex pain is a hot topic even for people in the BDSM/Fetish communities. It is a common misconception that you cannot avoid pain from anal sex penetration and that anal sex inevitably hurts. The standard advice – Bad Advice – goes something like this;

“Use lube, lots of lube, relax and don’t worry about the initial pain. It will go away.”

The image you see here is such a common scene for newb’s and so wrong.

While the above advice is extremely insensitive, it is not entirely incorrect. If you do choose to just keep persevering with having someone fuck your ass your body, and mind, will get the hang of it, eventually. Anal sex will become easy. But it just doesn’t have to be that way.

You will also be told to communicate with your partner. “Tell them what you feel.” That might seem straight forward and obvious enough but this advice can be strangely unhelpful. Firstly, for some, vocalizing the process of being buggered and trying to break down the experience into instructions, as you would to assemble a piece of Ikea furniture, is something of a mood killer. Such advice can be particularly useless for the inexperienced. They often don’t have an understanding of what all these new sensations are or have the understanding to describe what is causing the discomfort or pain effectively.

The following is the list of topics covered in this article and are links to the relevant section.

Avoiding Anal Sex Pain requires proper communication

All advice on sexual exploration starts with “you must communicate”. But no one addresses the struggles people have communicating aspects of their sexuality. People, or couples, struggle to communicate openly about the details of ordinary sex. It is not surprising that people have even greater inhibitions when it comes to discussing the “ins and outs” of anal sex.

Whenever we feel pain from other parts of our body (other than our ass) we can go into great detail to identify it, describe it and, thereby, deal with it. The sting from a paper cut is very different from overstretching our skin. Burns are different from friction burns. Muscular bruising, ligament damage or a torn muscle come with there own unique descriptions. However, when it comes to pain during anal sex feed back to the partners is so often limit to “Ouch @!@#!”, “What the F’ are you doing.” “Bastard, f’ing stop that!” This is not good communication.

Describing anal sex pain comes with a whole list of additional complication. Most people are at a complete lost when it comes to describing the pain they are experiencing during anal sex. So, because communication is vitally important we start by identifying the different sources of anal sex pain.

You cannot possibly expect to avoid pain if you don’t know, or understand the source of your pain. Here you will learn how to describe it. in detail. This will also giving it some perspective without going in to too much detail. For a lot more detail on the issue you can have a read of Anal Sex Problems.

Let’s see if we can improve the how to communicate the source of any pain from anal sex by identifying the different souses of pain.

Anal pain caused by static friction

Skin stretching pain

If there is not enough lubrication, then any attempt to penetrate the ass hole will cause pulling on the delicate skin around the ass hole. This is a stinging pain which is exactly the same as when you over stretch any piece of your skin. Similar but different is the stinging pain from the skin being stretched open too far. It is actually very unlikely that a cock will do that but it is important to try and distinguish the difference. The stinging caused by static friction is fixed by using lube, more lube or a different lube.

Most people do understand the importance of using lube but equally do not use nearly enough. Everything is nice an slippery on the outer surface of the anus but anal canal remains dry. The penetrating cock or toy does not lubricate the path in front of it and it feels like the anus is being torn to pieces by the invading phallus.

Open your ass

Avoiding anal sex pain starts with opening you ass. You will quickly realize that most of this article is (and most of the graphics are) dedicated to getting you to open your ass. This is the point where most would-be bottoms fail. The idea of opening your ass without making a mess is the biggest stumbling block. This is why discussing enemas goes hand-in-hand with anal sex. If you are not comfortable with the idea of trying to take a shit while someone is trying to penetrate your ass, you have some more reading to do – Eating and Enemas for Clean Anal Sex. It is also advisable to take time to practice anal penetration by yourself. Until you are confident you can open your ass without worrying about making a mess – Anal Training by Yourself.

Anal pain from muscle strain

The real issue for most and it takes some dealing with, is muscular stretching and straining. The is why you will always here the advice that you must relax. But that is a gross over simplification. Sexual tension and anticipation is good and not what we associate with relaxation. So what is the relaxation advice really trying to tell you?

You do need to be comfortable with the idea of having your ass penetrated. Relaxed in the head or rather free of certain anxieties is definitely good. But in reality the receiver must take an active role.

Once you have the lube sorted, the pain of initial penetration comes from one or both of the anal sphincters being pried open when they are not ready. Remember, the default state for both the inner and outer sphincter is shut tight. Then there is third muscle that nobody talks about, the Puborectalis muscle. The puborectalis crimps the bottom of the rectum and maintains the sharp Anorectal Angle. This is the normal state for these muscles. They are by no means relaxed when you are. No matter how relaxed we are mentally or physically, our ass remains shut tight for good reason.

Now if you force any muscle when it is clenched you will hurt it or damage it. But that doesn’t mean that you are going to need surgery or any sort of medical attention. You wouldn’t run off to the hospital pulled a muscle in your arm or leg. If you are smart, you might put a cold pack on it.

In that sense, the sphincters and puborectalis are just like any other muscle. Normally they only open/relax to let something out (that is when you are pooing). This is an active, pushing action not a state of relaxation. You can manually open the outer anal sphincter by pushing as you would to release a fart or go to the toilet. You need to actively push out to open things up and make it easier for things to get in.

Use plenty of good lube!

Put down a towel if it makes you feel more comfortable or to make it is easier to clean up, because lube should be all over the place. Selecting a good lube and using it properly is not as simple as you might think. For details on good anal lube you should read the article What is a Good Anal Lube.

You don’t just want lots of lube on your ass, anus and the cock (or dildo) you want lots of it inside you. You can buy cheap Lube shooters from any Adult Toy shop or if you want something that will last, works better and will help with your cleaning routine, look at the Max Injector.

Push out to let it in!

In this animation the woman is not in an idea position for pain free anal sex (see squatting below), but if you look closely you can see she is pushing her asshole out. As the cock pushes in, her anal sphincter(s) open and push down over the cock instead of them being push inward by the cock. She is pooping while being penetrated. As a side point, you can also see there is very little lube being used, if any, which is not where you want to start.

No matter what position you are in you must learn to push like when you are pooping. It helps greatly if you or your partner rub or prod your anus gently to help get the muscles moving and help you maintain the push when they start penetration. This can be a tough ask for someone inexperienced (Practicing this will be the subject of another article).

Because of this, the only stuff you want in your rectum is lots of lube, unless you are into the brown stuff. Because anxiety about being dirty will make your ass shut tighter than a fish’s bum you should read Eating and Enemas for Clean Anal Sex. Also, you are very likely to feel a desperate urge to have take a shit the first time you are penetrated, so you need to know there is nothing there (other than what you intended to put in there). Then when you feel the urge go with it and start pushing out.

Positions to Avoid Anal Sex Pain

Be on top and squat

You can see how this will naturally stretch the whole (or hole) area but it also sends a familiar message to the sphincter and puborectalis which will make them relax and causes the the anus to distend.

The images here shows the Squatting Cowgirl sex position. This is an ideal position with feet flat on the floor/bed and the knees raised. The beginner has full control of their position and pace of the penetration, good balance and can easily reach the cock to control the penetration. The second image show how leaning forward opens the ass further, but if your balance is compromised you will tense up, and that is counter productive.

In this next picture we have the standard Cowgirl Position. The knees down on either side of the partner. In this position you can see how the anus is naturally drawn in between the buttocks and the buttocks are drawn together. When you try to take your weight or lift yourself up over the cock, your buttocks (and asshole) tense and close. This is no substitute for the squatting position. It is just on where near as good for starting out.

Squatting Reverse Cowgirl has all the same benefits. Whether facing your partner or facing away squatting is the better option. The decision to go for one position over the other depending on the stiffness and curvature of the cock .

Child’s Pose

Child’s pose is a Yoga recovery position. You kneel and sit your buttocks on your heals and then lean all the way forward curving your torso over your thighs. The images below are perfect examples of Child’s pose. With your knees spread comfortably like the first image depicts, your belly (if you have one) and chest will have more space dropping between your knees/legs. This is usually the more comfortable of the variations and with your arms outstretched, you are better placed to transition to Doggy position with easy.

If you adopt the position with your arms outstretched, then you can use them to push yourself back while your penetrator remains still so you control the pace and depth of penetration. With your arms down your side there is no particular need to keep your knees together (most find it more comfortable to open their knees and let their belly and chest drop between the thighs) and your hands can grab your buttocks to hold them apart or you can reach right back and use your hands to guide the angle and pace of penetration.

This is another pose that will stretch the anus naturally and help it open up.

Happy Baby

Happy Baby is another Yoga recovery position. If you are on on your back, lift your legs and pull your knees down to your chest similar to this example or have your partner push your feet over your head. This is also excellent position for stretching the anus area. If your partner wants to go deep in this position they have to change the angle of attack once they are inside, but if they don’t this is a good position to stimulate the G spot (not really a beginners thing).

Warm up!

Good foreplay combined with anal stimulation helps get the mind and the muscles ready. But for women specifically, start with vaginal penetration. The thrusting and internal massage of vaginal sex stretches the anal sphincters and the puborectalis. This is a no brainer and will definitely loosen up all the muscles between her legs (the pelvic floor). The positive effects of stimulating the anus during “regular” sex are multiplied. As well, you are building the positive association between anal stimulation and sexual stimulation.

Use a vibrator

Another trick is to put a vibrator on (not in) the anus. This will loosen the muscles in a second or so. Using a vibrator on any muscle will loosen it. Keep resting the vibrator just above or below the anus while you are penetrated.


There is a significant disconnect between the sensitivity of the penis and a guy’s ability to perceive any pain his cock is causing. While the head of a guys cock is extremely sensitive it is astonishingly difficult for a guy to determine if his actions are causing any pain. Don’t get angry if your partner starts getting it wrong. Stay calm and tell your partner exactly what’s going wrong.

If you have no problem opening your ass, the single most important factor in avoiding pain from anal penetration is to communicate. Start with the assumption that your partner is not deliberately trying to hurt you. When you feel any discomfort, you need to stay calm, think about whatever discomfort or pain you are feeling and try to express that.

If you need them to stop for a moment use terms like “Hold it”, “Hold on”, “Wait”, etc. Sometimes you just need to relax or adjust and settle down. Take a moment for any discomfort to pass. Only us the word “Stop” when you actually want to stop. A complete Stop!

Having said all of this, there is only so much your can do to be accommodating. Your partner needs to take their far share of responsibility for your comfort and pleasure. For them, I strongly recommend another post of mine:- Starting with an Anal Sex virgin (nee:Anal Newbies for tops).


  1. Friesbaconnekkid November 30, -0001 at 00:00

    I was fucked by a man for the first time when I was 50. No pain whatsoever, just pleasure. The only discomfort I have ever had was when we were getting the proper angle for penetration, and one time when a guy fucked me dry. Bastard.

    • Max Private April 12, 2020 at 10:40

      Thanks J for your kind words. I always appreciate good feedback.

      I did have to go on a search myself but the answer was simple. I changed the name of the article. It is now called Starting with an Anal Sex Virgin. I will update this article with the new link also.

      Play safe.

  2. Jess Schmidt April 12, 2020 at 02:26

    Hello there,
    First of all: thank you for the work you put into your articles. It’s detailed, explicit and most of all a really good and reliable source for research.
    My partner and I are debating to try this step. We read alot on how the receiver should act and now I saw you mentioning an article about “Anal newbies for tops” but we couldn’t find it. Could you possible post or relink it again?
    Thank you very much

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