10 Anal Training Steps for Beginners

Anal training is a process you and your Dom go through to prepare you for anal penetration.

If you are new to anal play or have perhaps tried it in the past and experienced pain, then fear not. I’ve written a guide to anal sex in the form of 10 easy to follow steps.

By practising these steps you’ll learn to mentally and physically relax the sphincter, engage in anal stretching without any pain, and discover just how good anal sex can feel.

In this anal sex training guide, I’ll be writing from the perspective of a male Dom training a female submissive, but all these tips can apply to a Domme training her submissive man.

What is anal training?

Anal training is a process you and your Dom go through in order to prepare you for anal play, in whatever guise that takes for you. Usually, the end goal is penetrative anal sex, but not always.

You begin at whatever level your sub is comfortable with right now, and slowly escalate through the ten steps below as she becomes comfortable with each activity. By gradually training up this way, you avoid experiences of pain while learning to love anal sex. You might even be rewarded with intense orgasms if done right.

Anal training is useful because it:

• Enhances the power-play dynamic in your D/s relationship
• Adds a reward system into anal play creating a positive feedback loop
• Adds another string to your bow of fun BDSM scenes to implement into your play
• Allows you to build up to full anal penetration if desired by you and your Dom

The anal training ladder

The anal training ladder is a sequence of steps you’ll go through over the course of your training, each step building on the success of the last. You should not advance to the next level until you are comfortable with the previous one.

Anal training is important as a process of desensitisation for your sub. Anal play can be extremely intimidating when starting out. No doubt she’s read or heard horror stories from friends of pain, humiliation, or comical disaster.

You can’t just expect your sub to enjoy full anal sex from the outset if she’s had no experience in anal play before. Neither her body nor mind will be ready.

Just as you build up your muscles and fitness in the gym, you do the same with anal sex.

Here’s a typical ladder I would use when training my sub:

1. Talk about experiences/explore if anal play is of interest to her
2. Learn about anatomy
3. Overcome hangups
4. Exterior touches
5. Finger penetration (no movement)
6. Introducing a small butt plug during play
7. Increasing plug size and building up endurance
8. Wearing plugs during play and service
9. Penetration training with dildos
10. Anal sex

10 step anal training process

Let’s go through each step in a little more detail. I’ve created a handy anal training progress tracker which you can download to keep track of progress and help remind you of the ten steps.

1. Talk about experiences

I’ve said it before, but completing a sex menu is the best way to figure out if your partner is open to anal play.

It’s important to understand if your partner has had bad experiences in the past so you can navigate with sensitivity any feelings that may arise.

I’m already assuming you have an open dialogue with your partner about sex and are comfortable discussing your fantasies, wants and desires.

If this isn’t the case, do not pass Go. Go back to basics and get the foundation of your D/s relationship in place first.

If you already have good communication in place, but your partner has a hard limit when it comes to anal play, then I’m sorry, but you are out of luck. You’re going to have to find another kink to explore together.

That said, it may be the case that your partner, like many people, simply has misconceptions surrounding anal play that make them uncomfortable but can be overcome with education and a healthy conversation about anal sex.

Perhaps try asking your partner what it is about anal that turns them off and if there are any issues you can address.

2. Learn about the anatomy

Knowledge is power and all that. The more you read about your anatomy, as well as the experience of others, the easier you’ll find it to relax when you start your training.

Google some diagrams of anatomy to provide the context of where you’ll be exploring.

I also suggest investing in a copy of The Ultimate Guide to Anal Sex for Women which is a great resource for educating yourself about anal anatomy prior to anal play.

The rectal cavity is pretty large, isn’t it? Bigger in fact than the vagina. So once you’re inside, there’s plenty of room.

The complications arise at the anal opening, guarded by the sphincter muscle which clamps down hard at the threat of any intrusions.

The trick to anal play is learning to mentally relax this muscle.

Once you are able to do this, anal sex won’t hurt, because the muscle isn’t being strained. But this does take practice and is why this training is designed to work up from small to large objects over the course of weeks, all the time practising breathing and mindfulness in order to mentally relax that muscle.

As a guy, I would encourage you to go through some anal training yourself.

WOAH. WHAT??

That’s right. Nothing will give you a sense of appreciation for what your sub is going through than trying some of these techniques on yourself. Not only that, but given the position or your prostate, anal play can be very pleasurable as a guy.

It’s also a great comeback at dinner parties when the topic inevitably turns to anal sex and the women exclaim “I don’t understand why men want to stick it up there! I’d like to see them try”. You should see the look on their faces when you quietly explain you’ve already comfortably taken a nine-inch, thick dildo and it made you have the strongest orgasm of your life.

Cue open-mouthed silence.

3. Overcome your hangups

Easier said than done. Anal play is taboo. It can be messy. But that’s ok. You and your partner need to recognise that things may go wrong and it’s fine to laugh at yourselves.

And if it’s a mess that’s the main concern, why not be proactive and lay down a towel and have some baby wipes handy. Hey… shit happens.

If you are stressed or worried about an ‘accident’ then you’ll be stuck in your head, unable to relax your muscles, which will lead to pain.

4. Exterior touches

Now the fun begins. The first milestone is becoming comfortable with being touched externally. This can either be during sex or during a session explicitly designed for training.

If you are going to do it during regular sex, a bit of warning might be a good idea. Also, ensure your finger is well lubed up. Keep the stimulation brief, and check-in with your partner to make sure she is comfortable.

5. Finger penetration (no movement)

Once she’s comfortable with exterior touch, practise sliding your little finger inside her.

You MUST use lots of lube. That goes for all the steps from this point on. Lack of lubricant will cause pain and discomfort, the opposite of what you are trying to achieve during the process of anal stretching.

Once in, hold it still, with no sliding in or out.

This is to get used to the sensation of being full and learning to relax the sphincter muscle. Sliding in and out adds extra stimulation to the sphincter and can cause involuntary contractions which may lead to pain.

How and when you insert a finger is up to you, but I recommend you start when you are giving your sub oral sex. The clitoral stimulation ensures the anal stimulation is associated with the pleasurable sensations from the clit. Also, as you become more aroused, your body has a higher pain tolerance (which is a reason why your sub can be spanked harder when she is turned on).

If you are able to make her come whilst your finger remains inside her, even better.

After a few sessions, you can progress to using your index finger for a wider and deeper sensation. At this stage, do not slide it in or out (apart from initial insertion and removal).

6. Introduce a small butt plug

Invest in a set of butt plugs. You can purchase them in training packs which include several sizes.

Naturally, you want to start with the smallest, which is typically just wider than the width of your little finger (which she should now be used to feeling inside her).

I recommend purchasing ones with a flared base. This stops them from disappearing completely inside your ass. The toys pictured above are part of an anal training kit. I also like butt plugs that have a thin, t-shaped base.

The butt plug slides in and the sphincter closes around the narrow base. This will help her get used to the feeling of having a slightly girthier object stretching her rectum, whilst the sphincter isn’t stretched too wide or put under any more strain than it was when you used your finger.

Once again, it is recommended the plug be inserted when your sub is already aroused. Consider keeping it in whilst you perform oral sex. If she feels comfortable enough, you can leave it in during vaginal penetration too, which can increase her pleasure through the feeling of fullness.

At this stage, don’t leave it in for long periods of time. Aim for five to ten minutes.

7. Increasing plug size and building endurance

Your cock is most likely thicker than the narrow base of the smallest butt plug, hence why over the training sessions you’ll need to introduce the bigger plugs.

Once she is completely comfortable with the small plug, try the next size up. It will be thicker, so may be tricker to get in, but once in, the base is only slightly wider than the smallest one.

Increase the length of time the plug is kept in from 5 minutes to 20 minutes. At this stage, it should still be during sexual activity, when she is turned on. Only once you can comfortably take the size of the current plug should you advance to the next size up.

8. Wearing a butt plug during service

If you’ve got this far, congratulations. You’re able to keep a large butt plug in during sex for up to twenty minutes. By this point (which will have taken several weeks to get to) you shouldn’t need to even concentrate on relaxing, it should be unconscious. Having something in your ass should feel pleasurable and be associated with positive feelings, increasing your arousal levels.

This step is all about wearing a butt plug for longer periods of time, and during non-sexual activities, in order for it to become a completely natural feeling.

At first, go back to the smallest plug. Insert and wear it around the house whilst you do everyday tasks.

If you’re a sub reading this, then why don’t you put in your plug without telling your Dom. At some point during the day, whisper in his ear that you are wearing it, and see his eyes light up.

If you’re a Dom reading this, then use this opportunity to command your sub to go and put in her plug for you. You can do this by issuing a remote command via text, or just telling her directly.

For bonus points, set a timer that dictates when she can remove it. Aim for 1 to 2 hours at first.

As this becomes easy, increase the size of the plug.

You might also want to experience the thrill of wearing a plug out and about. Whilst doing the shopping, visiting friends, at a restaurant, at work…

It can be you and your partner’s kinky little secret.

I recommend investing in a set of soft silicone butt plugs with a T-shaped base, rather than those made of metal or with a round base. The silicone plugs are lighter, and easier to clean, and the T base is more comfortable than the round base butt plugs when worn for long periods of time.

9. Anal penetration training using dildos

There’s a difference between wearing a butt plug for sustained periods of time and having a real-life cock pounding your ass.

If anal penetration is your ultimate goal then you need to get used to the feeling of something continuously moving in and out of your ass. Up to this point, the game has been about learning to relax, associating anal play with positive feelings of arousal, and learning what being full feels like.

To simulate anal penetration now is the time to introduce a dildo or two (Not at the same time. That’s pro-level). Not only is a dildo thicker than a plug at the base, but it is longer.

You can use a sex toy you already have in your arsenal, or buy a toy specifically for anal stretching.

As with the plug, I recommend purchasing a couple of different dildos. One should be small and thin (to start with), and another similar to the size of your own cock.

Warm your sub up with anal play, a finger, or plug, and then carefully insert the thinner dildo. Slide it in around 3-4 inches, and leave it there for a few minutes as she gets used to the sensation.

Then begin SLOWLY sliding it just a few inches back and forth. Continually monitor her body language for feedback and ask that she vocalises if it feels good or bad.

If there is any pain, stop the movement and end the session.

If she says it feels good, then try sliding it in a bit further.

Over the course of several sessions with the thin dildo, work up to her being able to take the full length of the dildo, and it is slid in and out more rapidly.

Once this is easy, move up to the larger dildo. The extra thickness will take getting used to, so take things easy and keep communicating. I recommend practising with dildos multiple times before you move on.

If any discomfort is felt, drop back down a rung on the ladder and work your way back up again.

10. Anal sex

You’ve done it!

You’ve reached the final step in the anal training process. You and your sub should be very proud of what you’ve accomplished over the last few months.

The final step is full anal sex with your very own human penis. With any luck, this should be relatively straightforward given all the dildo practice.

But, there are a few things to take note of.

Firstly, you won’t have as much control as when you were using a dildo. You may accidentally slide in too fast, or not be aligned with her hole when you try and penetrate her due to an awkward viewing angle.

As the Dominant, you need to be sensitive to her requests and ensure she is the one in charge.

Once you penetrate her, only enter a couple of inches, then hold still. Allow her to get used to the angle and feeling, which will be different to the dildo. It may be hard to keep still as you wobble on the bed supporting your weight but try your best.

Only once she gives the go-ahead should you move further into her. Again, pause and check she isn’t experiencing any pain and is enjoying the process. If not, then stop.

Finally, once she is comfortable with your length, you can slowly move in and out of her a few inches.

Do not try and replicate porn at this stage. Pounding her ass mercilessly is the fastest way to undo all the good work and patience you’ve shown over the previous weeks. Accept that you probably won’t be able to thrust as you want for many more weeks of practice still.

It will happen, but you need to build up.

It also goes without saying that at all times you should practise good hygiene. Never put anything into her pussy (toy or your cock) after it has been in her ass, without giving it a thorough washing with soap and warm water.

Wrapping up this anal training guide

If you want to get started with training your sub to be your anal plaything, whilst she also thoroughly enjoys herself, then I hope the information in this guide has proven helpful.

In summary:

• Anal sex doesn’t need to hurt and is in fact highly erotic, arousing and pleasurable when training is done well.
• The process of training is about slowly working your way up the anal play ladder, communicating well with your partner at each stage, and only moving on to the next rung once she is comfortable.
• Training takes many weeks and months, and should not be attempted in one go.
• You’ll need to invest in a good set of T-based training butt plugs as well as a couple of sizes of dildo.

I’ve put together a PDF summarising the process along with an anal progress tracker, which you can download for free.

And that’s a wrap.