Anal Training by Yourself
First published December 1, 2019
© Max Private – All rights reserved

Feature image by dholl

Motivations for anal training by yourself

Motivations for anal training start with the motivations for engaging in anal sex. They might stem from either a personal curiosity or drive to experience being penetrated anally or the more selfless act of ‘giving’ their ass to a partner. In either case, this can be the manifestation of a submissive streak, even if the recipient does not consider themselves a submissive in a BDSM context. Just because someone is submissive, even in the extreme, it does not mean they are into pain. So, people who are not into pain should train.

If you want to skip the introduction and background, here is a list key headings in this article you can. You can click on these links to take you directly to the point you are interested in;

The common reasons why people want to train by themselves are modesty, anxiety and fears (fear of pain or fear of failure) or some combination of those. All these reasons are the result of a lifetime of negative social programming. The ass and anal sex in particular, are the subjects of derision. Sins in the eyes of religious doctrine. It is considered by traditional societal values to be dirty and filthy as is the stuff that comes out of it. All this feeds into our modesty in a self loathing way. Anxiety arises from fear of persecution and rejection, fear of pain and fear of failure.

All too common port anal sex

The fear of painful anal sex is a legitimate fear

Fear of pain, or any fear, leads to anxiety. Anxiety leads to painful anal sex. The anticipation of pain is comes from multiple sources of negative social programming. Uneducated reports and derisive commentary on anal sex tell us it is going to be painful. The proliferation of Anal Sex in porn overwhelmingly depict it as a brutal act of domination. It is a common thread within the BDSM community. There are also many reports from ex-porn actors that many of the brutal anal sex acts are not an act.

The normalization of brutal anal sex set false expectations in many men. Many think that any woman who consents to anal sex must enjoy the pain. Others just figure it is an inevitable consequence of anal penetration and at some point pleasure takes over. Now aside from the fear of pain leading to pain, many have already had bad, painful anal experiences.

Benefits of anal sex training by yourself

Anal sex training by yourself removes performance anxieties and body negativity. You are not expecting to hurt yourself either. The removal of fear and anxiety is going to make the whole process of penetrating your ass easier. When you are anal training by yourself, you don’t have to worry about anyone else pleasure or disappointment.

You can surprise a partner with the special ‘gift’ of giving their ass and be assured that it will be easy and without a lot of negotiations, discussions or experimentation. You will not feel obliged to put up with pain and discomfort to avoid spoiling the sexual encounter for someone else.  People want it to be a natural part of their sexual exploits and not be awkward.

Dealing with Mental Blocks

To get past a mental block you will do a lot better playing/training on your own. Even if you have a partner that is caring and gentle enough, you just need to focus on reprogramming/desensitizing your own psychological/physiological response. You can use simple classical conditioning techniques. The following is a detailed program for reprogramming yourself.

The following advice assumes you know about the anatomy of your ass. If you have any doubt read Common Causes of Anal Sex Problems first. You are also going to need a good anal lube to keep everything nice and slippery. You can find out all about What Makes a Good Anal Lube by clicking on that link.

Be comfortable with your ass

If you want to enjoy anal sex you have to be comfortable with your ass and anal sex training by yourself will make you comfortable with your ass. If you are not comfortable then you will have problems. I think it is fair to say that all the problems that people have with anal sex are in their mind. You will find another article here the deals directly with Learning to Enjoy Anal Sex. If you have misgivings about your ass, you need to address those first.

Most people’s anxiety with their ass stems from the Dirty issue. For the most part, your ass is not that dirty. It is not commonly know that in one field study it was determined that humans walk around with an average of 1 gram of fecal matter in their knickers/undies on a daily basis. You may not be one of those, but how would you know?

People pick up trace amounts of fecal matter off all sorts of horizontal surfaces. Like desks, benches, the arms of chairs, railings, etc. Most any time of any day you can touch (or scratch) your anus and your fingers will not turn brown. Occasionally you might detect that slight musty smell. Still most people don’t wash this off which is why we pick up traces of fecal matter from all over the place. The same can be said for sticking you finger in your anus. It is very unlikely it would come out visibly dirty. The ass is not as dirty as you might be lead to believe.

Not clean enough

For most people, the normal state of the anus is just not clean enough and nothing I say is going to change that. But you don’t have to hose your ass out or resort to laxatives. It is not that hard to make sure your ass is clean and free of poo for anal play. There are two articles that should help you with your understanding and put your mind at ease – Eating and Enemas for Clean Anal Sex and Issues with Enemas – Good and Bad.

However, when you are just starting out the simplest solution to keeping things clean is to start off your training while you are in the shower. If you are in the shower and do manage to get something sticky on your finger, there is soap on hand and plenty of running water.

Begin anal training getting comfortable with your anus

Your anal sex training starts very simply. You start by just touching your anus. You want to do it regularly. Like every time you go to bed, before you go to sleep. For most people, that means you are going to be touching it first in the shower to make sure it is clean. Hopefully, you shower every day. Don’t just performing utilitarian cleaning of the area, clean it and then take time to actually touch it. Feel the smoothness of the skin around it. Where the buttocks meat the anus. The smoothness of the skin that runs from the anus over the coccyx. Is the perineum smooth or is there a ridge that runs from the vaginal opening to the anus? Take time to find the center of the anus. The precise point of the anal opening. The point where your finger tip will start to disappear inside.

If you started this in the shower, then you should be comfortable the your are not getting any germs or poo on your fingers when you start touching yourself in bed. At first you may want to keep some baby wipes next to you for your own peace of mind. But eventually, you will be comfortable with touching yourself in this way without concerns of being dirty. This is the first big step for most.

Getting your finger in your ass

Don’t forget to have some lubricant’s on hand. You can get away with using any number of various household products. Cooking oils, butter and margarine all work well. You will find much more information in the article – What makes a Good Anal Lube. Until you are familiar with your anus and preparing for anal, training in the shower means you don’t need to worry about cleaning up. You are there with the soap handy.

Warning: Don’t let regular bathroom soap get in your anus. It will sting like a bitch. Think of what it feels like to get soap in your eye and now imagine that feeling in your anus.

Fingers are best

It really is so much better if you start with your own fingers. It is the fastest way to dispel any demons you have and it is so much easier to figure out how your body works. The little variations that make your body unique. Most of the time you lower rectum is empty. If you go to the toilet, specifically to poo, then your lower rectum will definitely be empty for an hour or two. Now there are exceptions. Obviously an upset bowel is a problem. Too many oily foods can also make your poo sticky and/or gooey. But as long as you have health bowel movements that are properly formed, you have nothing to worry about. It is not going to be dirty but, if you have doubts, you are starting in the shower anyway.

(Click to enlarge image)

Diagram showing inflated colon

Sacrum highlighted in Red

(Click image to see 3D animation)

Structural details

Using your fingers will give you an understanding of what your anus or anal sphincters are doing. You are going to practice controlling them. At the same time, you’ll be training them to respond favorably to your wishes. Your fingers are better at giving you the feedback you need and ensuring you don’t do anything that could cause pain in the early stages.

It will also give you a much better understand of how your rectum connects to your anus and the path into your rectum. The very first time you insert a finger for enough to reach the top of the anal canal, you might be surprised to feel that the top of the anus is closed off. The cover at the top of the anus is the front wall of the rectum.

Medical diagrams of the human anatomy misrepresent the normal state and arrangement of your insides. When your rectum is empty, it is squashed flat. The open space in the rectum depicted in cross-sections of the abdomen can only occur if you inflate the rectum/colon like a balloon. The rectum is squashed flat over the top of the anal canal, the pelvic floor, coccyx and against the Sacrum.

Continue to insert your finger beyond the first knuckle, you will need to hook your finger towards your tailbone. As your finger enters the lower part of the rectum it will begin to feel like open space that you see in the diagram.

Fingernails in the ass

There is a lot of fuss made about trimming and filing down fingernails. It is not a bad idea when you are sticking your fingers in someone else’s anus for the first time. But here is the reality, your ass just isn’t that fragile. A sharp edge on a nail will scratch, but you are not going to keep scratching away at your anus. If it feels scratchy, then file it. It is no different than any other soft tissue in your body. Try sticking one of your fingers inside your cheek (in your mouth) of under your tongue. Sure you can feel the end & edges of your finger nails. Sure you can make it hurt. You could do some damage to the soft tissue, but you have to be serious about it, clumsy or stupid. It doesn’t just happen. So don’t worry about spoiling a good manicure just for a bit of anal finger poking. Just make sure they are not torn with really sharp edges or pointy bits.

Sphincter training

Training the anus

Once you are comfortable inserting your own fingers (or at least one finger) it is time to move on. You need to start build the stretch in your anal sphincters and supporting structures. Any amount on a regular basis and up to three minutes a day.

With your finger in your ass and start gently stretching. Gently pull back on your anus, stretching the anus towards your coccyx. Then gently pull your anus from side to side then front and back again. Just get used to manipulating your anus without causing yourself any pain.

The inner sphincter

The stretching will start the release process of the inner anal sphincter. You cannot control the inner anal sphincter consciously. Pressure on and stretching of the rectal walls cause the inner anal sphincter to relax. As you feel the inner sphincter relax, you can release the outer anal sphincter by literally trying to poo.

At this point, you may be wondering about having an accident. Another good reason to start all this in the shower, but for real peace of mind, you need to review the article Eating and Enemas for Clean Anal Sex. You must practicing ‘bearing down’. Pushing your ass out like you are trying to poo. You will help your anus to relax by hook your finger into the open space of your rectum and around the back of your anus and pulling out gently.

Most people don’t know about the Puborectalis Muscle. Another muscle and set of ligaments connected to the anal canal. It only responds to stretching and pressure on the inside of the rectum. It is attached to the Pubic bone at the front of the pelvis and forms a sling around the back of the Anorectal junction. Adopting a squatting position will release tension on the Puborectalis muscle. By inserting a finger far enough to hook it over the top of the anal canal and into the rectum, you can pull down gently. At the same time, pulling back to stretch the Puborectalis will further release and stretch the anal sphincters.

Move on to two fingers

As you feel the sphincter muscles relax and soften (not necessarily on the first or on any given attempt) start working a second finger into your anus from your other hand. Sliding it carefully along the first. Be gentle. Be comfortable. Remember to breath. Your breath should be calm and rhythmic. Pause as you breath in. Push out with your ass and push in with your fingers as you exhale.

Gently stretch your anus side to side and front to back with your fingers. Just get used to manipulating your anus without causing yourself any pain. Over time (probably not a lot of time) you will find you can work your way up to two fingers from each hand. It may take you a week. Some days will be easier and some days will be harder. Listen to your body and only go as far as you are comfortable on any give day.

These are the most important anal exercises for making anal penetration easy and painless. For the most part, there is no need to stretch the skin or flesh around the anus. You just need to train the muscles to build flexibility and responsiveness.

Training with toys and more

When you are comfortable to move on, it is time to start probing deeper then you can with fingers. If you haven’t already, you should have the confidence to move your training out of the shower. Confident that your play is clean and accidents free.

Your first toy


Vibrators will further help relax your muscles. Here at we have vibrators specially select to help with anal training, as well as sexual stimulation in general. The best of these vibrators are highlighted here. They are water proof (for the shower), powerful (truly) and compatible with all lubes and cleaning products. You can read about their various benefits in the descriptions on the product pages. Having said that, you can start with a cheap, battery powered vibrator. Smooth plastic vibrators do actually work well, but are not as functional or pleasurable. Start with your fingers to relax your anus and then slowly replace your fingers with the tip of the vibrator.

Your practice with the vibe is to gently push in past the Puborectalis muscle. Gently gyrate the vibe as you try pushing it in. Squat or bring your knees to your chest is the best position. Concentrate on your breathing. Pause as you breath in. Push as you breath out. You should feel the resistance of this muscle fade fairly quickly (maybe a number of attempts) and when you do it is time to start sliding the vibe in and out gently and rhythmically.

Moving into the rectum

As you go deeper you will need more and more lube. You will be able to get the vibe in about 4 inches (10 cm) before you hit a potential roadblock. This is because of the Anorectal Angle. To proceed deeper (same with a cock) you have to navigate through the sharp corner into the main part of your rectum. To do this you have to tilt the head of the vibe (inside you) back towards your spine. You will be pulling the base of the vibe forward, towards your clit. This will put a whole new strain on your sphincters and Puborectalis muscle, so take it slow and gentle.

Just start by rocking the vibe back and forth. Concentrate on your breathing. This time start tilting the vibe toward you spine while you breath in and stop tilting when you feel the strain. Maintain the strain as you finish breathing in and as you breath out just angle the vibe a little more. Breath in holding the strain and tilt a little more as you breath out. When you are comfortable (you decide) start pushing the vibe further in as you breath out. More lube!

Getting to the top of the rectum

When the vibe is aligned with your rectum you can slide a vibe in easily until it hits the half way mark. At about 5 to 6 inches or 12 to 15 cm deep, the tip of the vibrator is going to hit the underside of the Sacrum. This exceeds the depth that a regular cock can get to. Even an over sized partner will never get the entire measured length of the erect cock into your ass.  There are bones and flesh that will stop a partner getting “balls” deep. Once you get to this point it is time to just practice sliding the vibe all the way in and all the way out, rhythmically, over and over again. Apply more lube.

But you might like to go further. There are plenty of toys longer then 5 or 6 inches. But the Sacrum is bone. It is a hard limit unless you change the angle of the vibe or you have a toy that will bend with the curvature of the rectum. The top of the rectum is at least eight inches or 20 cm up your ass. That is going to be deeper than the length of most vibrators.

Remember to start with your fingers for every training session. Warm yourself up to where you were before. But now it is time to imagine the vibe is a real cock. Think about your partner penetrating ass while you are doing it. As you are sliding the vibrator in and out. This is a standard brain training trick. Ideally now you should be masturbating yourself to orgasm. This is actually very important in Classical Conditioning, to associate anal sex with all the sensations of sexual gratification.

Moving to a real Cock

When you introduce a real cock it is a really good idea to let your partner see how you warm up your ass. This will allow you to consider yourself first. This can be an excellent form of foreplay. Especially, if you are feeling nervous at all, start warming yourself up with your own fingers (not your partner’s). Focus on yourself and even consider starting your warm up on your own. If necessary, go through the exercise steps with your vibe. Be touching each other. Looking at each other. Imagine it is his cock when you are warming up with your vibe.

When all seems good and you feel ready, and you are together with your partner, start by imagined his cock penetrating your ass during foreplay. This is again an important technique used in classical conditioning. Imagine the position your will be in with your partner. Image your are actually doing it with your partner while using your fingers and toys.  Then it is time to use the real thing. At this point it all the warm up might come very easily, But even for an anal veteran, warm-up is still important.

Ready for Anal Sex

As you ready yourself to take his cock it is time to inject a good dose of lube up your ass (see: Good anal lube). Make sure he is lying on his back with his cock standing up to start with and when you feel ready, position yourself over his cock, still with the vibe burred in your ass. Slide the vibe in and out a couple more times and when you are ready, slide the vibe out and gently guide his cock into your ass as a replacement. Remember your training. You have to get passed the sphincters first, then the Puborectalis muscle, then the angle into the rectum. You control the speed of penetration and the angle. Remember your breathing. Sit/push down on the cock as you exhale. Pause as you inhale. Take your time and concentrate on your breathing until you are sitting right down on his cock. Start gyrating, maybe bouncing a little yourself before you let him start to take control.

I figure you can sort it from there.

Play safe.

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