A Beginner’s Guide to Anal Training

Anal isn’t inherently kinky, but anal training is something that comes up in plenty of power exchange dynamics. Partly to prepare for future anal sex and partly for the control and “training” aspect between a Dom and their submissive.

Anal training is a slow progression in anal play that allows the bottom (literal and figurative) to get used to penetration. Training helps prevent pain and (usually) makes anal play better over the long term.

If you’re new to the idea or you know you want to do it but don’t know where to start, here’s what you need to know.

What is Anal Training?

Simply put, anal training is the act of getting your anus used to and comfortable with penetration. Anal training often takes place in stages over time as a precursor to anal sex (with a dildo or a penis). Though it doesn’t have to end with sex. Anal training can be great simply for using bigger butt plugs, prostate massagers, or anal beads.

Not everyone considers anal kinky. For many it’s simply one way to engage in sex. But anal training often occurs in power exchange relationships, especially if anal is a shared desire of both partners. In this way it functions as both a sexual thing to do together and a form of submissive/bottom training.

Check out this video for a quick explanation of anal training.

How to Do Anal Training

In general, anal training follows a few basic steps, depending on your previous anal sex experience. For those who have never engaged in any form of anal play, it tends to look like this:

1. Touch your anus externally, using a finger or sex toy.
2. Slowly introduce a small, slender anal toy or your finger tip and penetrate yourself.
3. Once this size becomes comfortable, move up (slowly!) to larger sizes.
4. As you insert larger toys or body parts into your butt, increase the amount of time spent during penetration.
5. Reach whatever goal you’ve set for yourself — penetrative sex, specific size of toy, etc.

For those who have tried anal already, you can typically skip the first step of external play and go straight to the smallest size you know you enjoy without pain.

Why start with external play for newbies? For anyone who’s never had anything more than toilet paper (or soap and water) near their ass, the first touch can be overwhelming (in good and bad ways). There are a lot of nerve-endings in and around the anus. Sometimes the surprise of that first sensation causes everything to clench up — making penetration more difficult. Getting used to external sensations is a gentler beginning for many newbies.

Safety Tip: Anytime you engage in anal training or sex with a person who has a vulva, do not use a body part or sex toy in the vagina that’s been in the anus first. You can switch from vagina to anus BUT you can’t switch back without introducing (potentially) harmful bacteria from the booty into the vagina! Wash up before you switch from booty to pussy, y’all. The vulva in your life will thank you for that.

What to Use for Anal Training

Okay, so you know to start small, and progress until you’re happy with the size of the body part or toy in your ass. But what do you use, and how do you make that happen? Here’s what you need for anal training.

Lube

The one thing you never, ever want to skip is lube.

Lubricant is the one constant in any form of anal sex. You need it from start to finish, and you’ll likely add more while you play. From fingers to butt plugs, never, ever, EVER do anything anal without lube.

The kind of lube you use will depend on what else you’re playing with. If you’re using your hands and fingers (see below), any lube will do. When you use a sex toy, you need to choose a lube that’s compatible with the material of the toy.

In general, remember these lube rules:

• Water-based lubricant is universally safe and can be used with anything. (Check ingredients for known sensitivities and/or allergies).
• Silicone lube lasts a bit longer and is thicker, but it’s not safe to use with many (but not all) silicone toys and none of the jelly, rubber, or TPR/TPE toys.
• Oil-based lubes are GREAT for anal, but they’re best with metal or glass toys. Oil-based anything is a big no if you’re using condoms or other barriers to prevent STI transmission or pregnancy.

Check out all the lubes available at She-Vibe.

Fingers

As with anything sexy or kinky, you can always go wild with gear and sex toys. And if you’ve got the budget for it, have fun! But the cheapest, easiest way to get started is with your own hands (or your partner’s).

If the idea of touching your own butt squicks you out a bit, you can always wear gloves or take extra care to make sure your butt is clean. But, in general, you’re not going to get poop on your fingers — there are exceptions to that, usually based on timing of your bowel movements or if you feel like you’ve got to GO right now.

Since you’re going to need to lube up, especially if you explore anal training alone at any point, get used to putting your hands on your anus. It’s part of the experience.

But it’s also the cheapest way to explore anal sex without the need for a bunch of gear.

Anal training is all about slow progression from a little to a lot. Here’s what that can look like with your fingers:

1. Start with the tip of your smallest finger.
2. Work up to full penetration of your smallest finger.
3. Move to the next larger finger.
4. Once you’re good with single digit penetration, work on penetrating with two fingers, then three.

This also works if your partner does the penetration, too. They can start with their pinkie and ultimately move up to their thumb, though some people start with the thumb.

Sex Toys

Of course we’re going to mention sex toys. The important thing to remember about anal training is that you start small and work your way up. Your end goal might be your partner’s massive cock or a huge dildo, but that’s not where you’ll start.

The best sex toys to use in anal training are those that allow for a gradual increase in size. Meaning you start with a small one and work your way up through larger sizes. Here are a few suggestions.

Anal training kits: Training kits tend to include multiple anal toys of varying sizes or the same type of toy (like a butt plug) in multiple sizes. This allows you to make one purchase and have several toys to progress through. Check out these anal training kits from Stockroom.

Anal beads: Anal beads do what a kit does but in a single sex toy. Beads are a great way to play even if you’ve been doing anal for a while, but to train, you insert the beads up to the largest size you can handle without pain. Your training progresses through larger and larger beads until you can handle the entire thing OR until you’re happy with a specific size. Check out these anal beads from Stockroom.

Butt plugs: Plugs are fun for showing off for your partner, wearing in public without anyone knowing, and yes, they’re great for anal training. Start with the smallest, most slender butt plug you can find if this is your first one. If you think it’s too small, and you’ll “barely feel it,” it’s probably just right, and it might feel huge. When you’re ready, go up a size. You might try a different design completely or you may stick with the same style just in a bigger size. Check out these butt plugs from Stockroom.

How to Prevent Pain During Anal Training

Other than the squicky poop factor, the thing that keeps a lot of people from exploring anal is the idea that anal always hurts. While pain during anal sex is common, it’s not required. You don’t have to brave the pain as part of your booty fun. In fact, pain is a sign that something has gone wrong and that you should probably stop. Also, the anus is really delicate so pain may indicate an injury. And yes, butt injuries are a thing.

How do you prevent pain?

Lube, lube, lubity, lube. When you’re new to anal, there’s no such thing as too much lube. If you feel pain with penetration, try adding more lube first.

Start small. For newbies, you’ll probably be shocked at how large your fingertip feels if its the first thing you’ve ever put up your butt. Don’t get overly confident and buy the “medium” butt plug instead of an extra small. The smaller you start, the better.

Give your body time to adjust and relax. If the first bit of penetration feels good, stick with that size as your body adjusts. For a little bit of pain (not the bring-tears-to-your-eyes kind), sit still, breathe deep, and let your body adjust to the sensation.

Don’t create arbitrary goals. Pushing yourself too hard for a deadline means you’ll likely rush through your “training.” Take your time and let your body guide how quickly you move from one size to the next.

Take breaks. If you feel frustrated or you’re struggling with a bigger size, don’t force yourself to continue. This is meant to be fun and pleasurable. Take a break or stop completely if that’s not happening.

Add extra stimulation and sensation. This won’t work for everyone, but some people find that if they can become aroused in other parts of their body – often to the point of orgasm – they can help their body relax for anal penetration. Stroke your cock. Use a vibrator on your clit. Play with your nipples. Use a vibrating anal toy. Whatever makes you feel good may help you relax and reduce the pain.

Don’t ignore pain. Pain is a signal that something isn’t quite right. When you feel it, slow down, go back to a previous size, or stop completely. Don’t move forward in your anal training until the step you’re on is pain-free.

We do not recommend using “desensitizing” lubes for anal. When you use those lubes, you’re bowing to the “inevitably” of pain during training or sex. It doesn’t have to be painful, and you don’t have to numb yourself to it. Plus, without the pain, you’re not listening to your body and what’s working for it (or not).

Use pain as the information it is: Slow down or stop. Ultimately, what prevents pain during anal sex the most is patience.

Power Exchange and Anal Training

We’re all about kink and power exchange around here, so that’s how many of us think about anal training.

• A D/s couple wants to incorporate anal sex into their play, and anal training helps their submissive partner get ready for it.
• The Dominant wants control over their submissive’s body and they mutually agree to try anal training.
• Wearing butt plugs in public turns both kinky partners on, but the bottom or sub is new to it so anal training helps them.

But anal sex isn’t automatically about power exchange (just like it’s not inherently kinky). If you have an asshole (and we don’t mean your ex), you can explore anal training and play. Some Doms want to be penetrated anally. It doesn’t make them any less in control. Some subs want to be the penetrator instead of the penetratee. They’re still submissive in their relationship.

In fact, topping your Dom in that way could be seen as an act of service or submission.  It’s all about how you approach it.

Whoever is going to have something shoved in their ass needs some level of anal training. Long-time players may be just fine without it, but we recommend training for anyone who hasn’t had anal sex in a long time.

Ultimately, remember these things:

• Not everyone considers anal sex “kinky.”
• You can not want anal sex and still be kinky.
• Anal isn’t required in power exchange.
• You don’t have to be submissive to want anal or experience anal training.

How to Add Anal Training to Your Power Exchange

Like anything else, you’re going to need to talk about it, make a plan, and get the consent of both partners. Here are a few ideas to help you do that.

• Set aside time to talk about it. In that conversation, discuss why you’re interested, how you’d like to see this progress, and what you’d like to do.
• Listen to your partner. Once you’ve shared, sit back and listen to them. If they ask for time to think about it, give it to them.
• Don’t pressure your partner to do anything, including anal training. This needs to be their decision with informed, enthusiastic consent.
• Check in with each other frequently. Make sure your anal training plan still works for both partners after it starts. Give each other space to talk about what’s not working.
• Adjust your plan as needed. This may mean stopping at a smaller size than originally planned. It might mean slowing down a little more. Hell, you might even adjust to make training last longer or work up to a larger size.

Bottom Line…

If you want to explore anal play or penetration, anal training is a great way to make sure you have a pain-free experience. Give yourself time and be patient with yourself. You’re turning an exit into an entrance, and it may not be a quick or easy process. Above all, make lube your best friend.

And for you kinky folks, if you want anal training to be part of your dynamic, make sure you talk it through with your partner and that both of you consent. Anal is definitely something you can do on your own, even if your partner’s not into it. But you can’t force a partner to go through anal training if they don’t want.