Opening the Back Door: Anal Training 101

by Kristin T.

April 29, 2023


It’s the beginning of the (rear) end. You’ve finally decided to take the plug. . . er. . . plunge and give anal play a try. How exciting! You’ve thought about it, you’ve talked about it, and you’re ready to start anal training! A desire to properly prepare yourself for anal penetration is the first step of many on your way to sphincter-stretching success!

Sadly, anal sex is shrouded in a lot of shame and stigma, causing many folks to scoff at it or just pretend it’s not a thing…or at least, not a thing for them. Harboring a lifelong attitude of “nothing goes in the out door” may be hampering your full enjoyment of sex and all its glorious options. If you and/or your partner have not yet embraced the power of teasing the tushy, you’re missing out on unique sexual sensations that many, many people love! It may also mean things are a little tight back there. Not to fear…anal training is here!

OK, so what IS anal training?

Anal training, quite simply, is a process intended to gradually “stretch” the anus to get it used to penetration for anal sex. Anal sex and anal play comes in many different forms, including penile penetration, strap-on sex/pegging, analingus (anal/oral sex), prostate massage, and solo or partnered play with anal plugs & vibrators.

Keep an open mind. Anyone with a butthole can enjoy anal sex! Its enjoyment is not limited to gay men (or men, period), though penis owners do have the bonus feature of the prostate gland, which can make anal play feel extra good! Above all, the anus – everyone’s anus – is just another erogenous zone that can make you orgasm. Vagina owners can enjoy anal activities, too. Even small, simple butt plugs and anal vibes can provide an extra touch of pressure, feeling of fullness, and tons of fun to vaginal sex. That’s a great place to start to see if you might enjoy anal sex. Anal penetration with a penis is rarely something that “just happens”. It takes a lot of discussion, consent, and preparation. It is a goal to work up to, and anal training is the way to do that!

Now, without further ado, it’s time for a little Anal Training 101! Follow these ten tips to make the most of it, and you’ll be graduating to new anal adventures in no time!

1) Train Your Booty AND Your Brain

Anal training is as much a mental activity as it is a physical one. A big part of anal training is to get over the (somewhat natural) fear or anxiety about things entering your asshole. For most people, the automatic physiological response to anything penetrating back there is a big fat “NOPE”. The key is to, as this post from The Submissive Guide puts it, “turn hesitation into penetration”. Your thought patterns need to allow the entry before your muscles will.

A big part of anal training is simply being mindful, staying in the moment, and training your brain to participate as much as your body. That gray matter is, after all, does play a big part in how we experience sexual arousal and pleasure. Keep an open mind, breathe, and focus on relaxing your mind and those muscles. Don’t rush (more on that later), and try not to get disheartened when “you just can’t do it” or dwell on setbacks. Just take a deep breath and try again. If you can train your brain, it will allow your body to get through the fear and on to the fun!

2) Explore Your Anatomy

Just like the self-exploration you do when you’re learning to masturbate, it’s important to familiarize yourself with your butthole, too. Start small…like, fingertip small. Just explore the opening next time you’re in the shower. Gently insert the tip of your finger gently into just the first 1/2 inch or so of your anus. Run it in a circle around the inside and see how sensitive the nerve endings are there. Try thrusting it in and out and feel the differences as the inner and outer sphincter muscles contract. Feel for the natural angle your anus goes; this will help you when you’re beginning to insert plugs.

If it helps you to know more about the science behind everything, Cleveland Clinic offers a great definition page all about anal anatomy, as well as the image below. This may also help clear up some of your concerns about hygiene. While anal sex can of course get…well, shitty…it’s not that hard to keep it clean. Especially for how deep you’ll be entering for your earliest exploration, cleanliness shouldn’t take much more than a bowel movement the same day as the anal play (a few hours before is idea) and a shower or wipes to clean the outside.

3) Use Lube. I Repeat, USE LUBE!

For comparison’s sake, the vagina IS a self-lubricating orifice, and most of us know how important and beneficial lube still is for pleasurable vaginal sex. The anus is NOT self-lubricating. If you’re planning to penetrate it, it relies completely on outside help from a good lubricant. Friction is not your friend. If you attempt anal play – with toys or with body parts – you’re gonna have a bad time if you don’t use lube.

So what type of lube should you use? As a general rule, silicone lube is best for anal sex. Silicone lube has a slipperier consistency and is a tad thicker than water-based, helping it stay in place better. It is also less likely than water-based lubes to become sticky with friction.

That being said, especially for anal training where you’re likely using silicone butt plugs, you need a water-based lube. Silicone lube and silicone toys do not mix; it will break down the toy’s surface over time, allowing it to become porous and harbor bacteria. That’s not safe! Water-based lube is perfectly sufficient for the purpose of inserting plugs or fingers, since there won’t be a lot of thrusting action occurring. You just need something to help it slide in!

Apply lube directly inside your anus with a finger, AND apply plenty to the toy or body part that will be penetrating it. Once you’re an anal expert and being penetrated more deeply, you may want to use a lubricant applicator to shoot it right up into your rectum. These can help make things easier and less messy, but they aren’t a must.

4) Don’t Push It!

Not to the point of straining and pain, anyway. While you of course have to apply a decent amount of smooth, gentle pressure to get things in your butt, you should never have to force it, and it should never genuinely hurt. If you find yourself wincing and gritting your teeth in agony as you try to insert it, you’re not ready. As your rectum gradually gets used penetration being a regular thing that happens, it will become much easier and less painful. That’s when you know you’re ready to move to the next level, and not a moment before then.

Pain is the message the body sends the brain to let you know that something is wrong. If you feel (or hear) anything indicating too much pressure, or that something is overstretching/tearing, stop immediately! For this reason, it’s also best to avoid any kind of numbing agents around your rectum when you’re doing anal training…you don’t want to quiet that very important alarm system. A naturally relaxing but non-numbing anal serum, such as Daring for Men or Adventure for Women by Intimate Earth, is fine to try if you see you need a little help. A CBD lube may also safely help relax everything down there as you begin to push your new limits.

5) Start Small, Soft, and Safe

One of the most common sex toys used in anal training is the good ole’ classic butt plug. Butt plugs come in many shapes, sizes, and materials. If you’re a brand new beginner, the most important features to look for are a small size and a soft material. Harder plugs made from glass or stainless steel are a thing, and many people love them. They’re great for providing firm feelings of fullness and lots of sensation play options. These will be great down the road a little farther, but when you’re just starting out, a skinny & short plug in a soft silicone is your best bet.

Remember that the other MOST important feature of any anal toy is that it has a flared base or a retrieval loop. If anything without those features goes too far up into your butt, it’s not coming out without a trip to the ER. That’s traumatizing for anyone, and you definitely don’t want it to be part of your anal training journey! It’s also important to make sure your toys are made from body-safe materials. Part of the fun of training often involves wearing your plugs for an extended period of time. Whatever you choose, it’s just important that the plugs you use for anal training seem just right for YOU!

6) Work Your Way Up

Conveniently enough, tons of companies have made buying plugs for anal training easy by selling them in sets! Lots of sets are available to help take the guess work out of choosing how to go up a step in size. Plugs can increase gradually in length and/or diameter, but often they do both. Your first few times with the next largest size may be challenging, but eventually your bum will come to accept the size and pressure of insertion as normal.

The Fun in the Bun set (pictured below) is a great non-vibrating option for many; the narrow stems and curved flared base makes it perfectly wearable for those with a vagina! The Booty Call booty trainer kit might be even more of a “just right” fit for you if wider plugs seem terrifying. Bringing a little more girth but also the motivation of vibration (the largest plug vibrates), our exclusive Love Essentials Anal Plug Set may be just the ticket. If you’re ready for more of a challenge, you can even get a graduated set in gorgeous glass!

Butt plugs in graduated sizes for anal training.

If you’re really ready to commit, B-Vibe makes a great Anal Training Set that comes with everything you need! The largest size may seem a bit large and intimidating, but if you follow the guidance in their educational “Complete Guide to Anal Play”, you’ll be ready for it safely and sooner than you think! B-Vibe is actually the master of all things anal education, so if you want to learn more, check out their Anal Academy pages. You’ll find more great information on anal training, and almost anything else you may be curious about when it comes to your bum.

7) Enjoy the Sensations

Anal training can be a great mindful activity! Remember that the point of all this work is to be able to enjoy and appreciate anal pleasure. With this in mind, focus on how things feel when you are exploring with a finger or playing with a plug. Explore many different types of plugs and toys, too, and the variety of sensations they can offer.

Experiment with stationary (non-vibrating) plugs in different and unique sizes and shapes. Penis owners can try vibes focused on their prostate; some even have unusual stimulation options such as tapping or deep rumbling vibrations. Try a plug you wear for awhile that arouses and excites with weight or a self-vibrating bearing inside. Longer glass wands or heavy stainless steel wands are great for partnered play and temperature exploration. Whatever you try, focus on the different sensations it creates and how they make you feel. You’ll learn in time what kinds of sensations you love, and which ones you can do without.

8) Take Your Time

While the ability to have mind-blowing anal sex may be the finish line, anal training is never a race. Go at the pace your body allows you to. Remember, you’re working on gradually being able to truly enjoy anal penetration…not just being able to shove something in there. If you force things or make your body accommodate something when it still hurts, you’re not going to be able to derive sexual pleasure from that, and you may set back the progress you’ve made. Your mind is a major player in this. If you start doing things to your body that your brain tells you are painful, you’re going to have a hard time getting to the point of sexual ecstasy…ever. Enjoy the journey as much as the destination, and don’t rush.

9) Get Your Partner On Board

If you’re doing anal training for any reason other than opening a new avenue for self-pleasure, hopefully your partner is already invested. Remember to let them assist! Maybe it’s just being there for aftercare and to talk you through your insecurities or any hang-ups along the way. Or, maybe it’s more of a physical support you need. Have them begin to explore with their fingers, tongue, or a toy once you’re ready, this moral support goes a long way. Plus, they’ll probably notice any little progress you’ve made along the way, and their new options for touch will be very motivating feedback! Any little doses of pleasure they can offer you through the backdoor route will also be a fun reminder of why you’re doing this in the first place…to achieve the ability to have pleasurable, earth-shattering anal sex.

10) Be a Lifelong Learner

Even if you don’t feel the need to train long and hard enough to stretch your bumhole to pornstar proportions, anal training isn’t a once n’ done kind of thing. Muscle memory is a real thing, and your sphincter muscles, once you stop having anal sex consistently, will remember to go back to their main goal, which is keeping things out rather than letting things in. You have to keep occasionally having anal sex, wearing plugs, or doing other anal training activities. This “reminds” your body and brain that entry is okay, and keeps your muscles accustomed to that penetration. Otherwise, you risk experiencing a level of hesitation and discomfort similar to when you first started your anal training adventure!

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