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Part 3 of Anal 101: Beginner’s Guide to Anal Training - How you’ll learn to love anal sex

If you're anxious about anal play, there is an easy way to make it more pleasurable. Anal training allows you to get familiar with the feeling of having something in your backside. It also can help stretch things out, so you're better prepared for penetration.

You can do anal training in just a few simple steps. (1) Get yourself sexually aroused. (2) Use your finger to explore your anus. (3) Generously lubricate and insert a butt plug. (4) Wear your plug around for a little while. (5) Move up in plug size as you get comfortable. It can take a few days, weeks, or months to build up to full penetration. Anal training will make that first time and every time after much more enjoyable 

Anal training can be an integral part of making anal sex enjoyable. Taking the time to relax your mind and body can make the whole anal experience much more pleasurable. 

Not everyone needs training. If you're reading this blog, then you're probably a bit apprehensive about anal play and penetration. Take the time and go through the training steps to make the most out of your anal experience. 

Part 1: Anal Anatomy 

Part 2: Anal Cleanliness

Part 3: Anal Training

Part 4: Anal Penetration


All products recommended are personally selected by me, Elaine S. Turner. I choose them and genuinely believe in them. However, this article may contain affiliate links. That means if you use that link to buy a product, I may earn a small affiliate commission, or tip, as I like to see it. You can learn more here if you have any questions about my affiliate policy.


Three types of anal play personalities

Anal sex isn't the same adventure for everyone. You'll come across people who love it and some that tried it and didn't enjoy themselves.

Both of those are okay!

So is everyone else in between. 

When it comes to anal penetration and play, there are three archetypes that everyone seems to fit into: 

Type 1: Born ready 

You're naturally receptive to being anally penetrated and do not require any training. You are a relatively rare type of person! If you're skipping training, then still use plenty of lubricants and take your time with penetration. 

Type 2: Gentle coaxing

You're interested in the idea of anal play, and it isn't something you're too worried about. If this is you, a few hours of anal stretching and play may be enough to get you ready for anal penetration.

Type 3: Cautiously concerned

If this is you, you're in the majority. You want time to prepare for anal play and penetration. Training is ideal for you. You're concerned about any number of things when it comes to anal. Take all the time you need to get comfortable! You may need a few days, weeks, or months of training. If done correctly, the process can bring you untold amounts of pleasure and fun!


Anal training supplies

If you're ready to get into anal play and training, you're going to need a few things. So grab your shopping list.

  • Lubricant - Either a thick water-based lubricant or a silicone-based lubricant. The type will depend on what your anal toys are made out of. If they contain silicone, you can only use water-based lubes. If your toy is metal or glass, then you can use silicone-based lubricant.

  • Butt plugs - Characterized by having a flared base and a rounded, bulbous tip or a slender one. These can be purchased online or in an adult store. You'll need at least 3 of varying sizes as time goes on. Many adult sex toy stores have training kits with small, medium, and large-sized butt plugs. Be cautious and choose a safe anal toy by reading our previous article on sex toy safety

  • Cleaning supplies - In case of an accident, keep a towel,  hand wipes, and similar items on hand. 

  • Arousing toys and materials - One of the critical parts of training is teaching your brain how to relax and enjoy the experience. Whatever you usually do during solo sex, do it during training too. 


Step-by-step anal training

Anal training is best done by yourself in a masturbatory style. Save the partner play for once you're more comfortable with your anal pleasure.


Step 1: Get your engines going

You need to get yourself aroused. As I said before, you're training your brain as much as you're training your anus. 

Pleasure yourself as you would during solo sex using whatever you please. 

Remember that arousal for penis-owners tends only to take a few minutes. In contrast, vulva owners can take as much as 45 minutes to get aroused. Take your time and play with yourself. 

Simultaneous familiar pleasure is the most critical part of the process for a Cautiously Concerned person. 

If your brain anticipates discomfort, your internal sphincter will close off. An anxious sphincter may mean you have to wait on anal training. 


Step 2:Get comfortable

Generously lubricate your finger. While still practicing solo sex, massage your rim and slowly slide your finger into the anal opening. Take the time to massage your sphincters before going all in. 

Feel around and get familiar with your insides. If you experience resistance about an inch inside, you've found your internal sphincter. Gently push your finger through it.

If you experience pain or resistance, pause and breathe through it. If you're uncomfortable and want to stop here, then wait until the discomfort has subsided. Then slowly pull your finger out. 

It may take a while to get used to this and to get through your internal sphincter. Don't rush it. Take all the time you need. 

If you find that you can pass through, play around with your anal anatomy. You may find that anal fingering brings you a substantial amount of pleasure.

Once you're comfortable with this, move on to step three. 


Step 3: Plug away

After mastering the art of anal fingering, you're ready for the next step. 

Grab your smallest butt plug and smother it in more lube than you think you could need. 

While still pleasuring yourself, place the lubricated plug on the outside of your sphincter. Slowly push the plug inside. Or, push yourself onto the plug. Take as much time as you need.

If you experience pain or resistance, breathe through it first. Then slowly remove the plug. 

Once you get it past the sphincter gate-keepers, you'll notice that the plug is quickly sucked up inside of you. The flared base should rest comfortably outside.


Step 4: Relax

Once the small plug is comfortably inside of you, you can continue to masturbate to orgasm. What you're doing is training your brain to find anal sensations not only acceptable but pleasurable. You're linking the two together cognitively. 

Wear the plug for 15 minutes to an hour. Whatever you have time for. You may find that you're comfortable enough to get up and walk around while wearing it. 

Repeat this process as many times as you'd like with the small plug. When you're thoroughly comfortable and finding pleasure in it, you can move to the next size. 

Again, this can take days, weeks, or even months. Don't rush yourself.


Step 5: Level up

Repeat steps 1-4 with the small plug until you're entirely comfortable. Then move up to the medium size repeating the same steps and similar wear patterns.

Before you know it, you'll be onto your large plug and ready for more anal play! 

We strongly recommend using a penis-shaped vibrator before moving on to full anal penetration.

This way, you know that you can insert something phallic before doing it with a person.

Plus, the vibrations may make the experience world-rocking by itself!


Anal training is personal and shouldn't be rushed. If you find that you aren't experiencing pleasure from anal play, that's okay! It isn't for everyone.

If your partner is pressuring you for full anal sex, calmly remind them that it is just everyone's cup of tea. Maybe you only enjoy anal-oral contact or anal fingering. That's totally normal. 

Do whatever you're comfortable with and whatever pleases you. 

It's your anus, your rules, after all! 

If you're experiencing anxiety around anal play or want to know how to talk to your partner about it, inquire with me today.



“There are no shortcuts to any place worth going.”

— Beverly Sills


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