How to Train Up Your Butt for Anal Sex of All Kinds

Anyone who's gone on an anal penetration journey knows you can’t just jump fist-first into a hole. Here's how to get started.

Apr 20 2021, 6:40pm
Advice on the finer points of having great sex.

Butts are wonderful. Not only do they look great, but they’re also full of nerve endings, meaning anal sex can result in some bomb orgasms. But, as pleasurable as penetration can be, butts need to be warmed up first—anyone who has started their anal journey knows you can’t just jump fist-first into a hole.

“Anal training” refers to the steps to getting you and your anus prepared and happy to receive butt sex by gradually stretching it with fingers and toys, little by little and over time. Training, luckily, is part of the fun of all things anal—and it can be done solo or with partners.

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Your anus consists of two sphincters: an inner one that you can’t control, and an outer sphincter that can be taught to relax, to open, to let pleasure in. As your body gets more accustomed to various sizes of toys, you can move on to bigger toys or body parts as you wish. Whether your anal dream is full-on penetrative butt sex or just getting more comfortable with using fingers or plugs, I’m here to explain how to gently romance your butt into opening wide. Anal training takes time, practice and patience (and a lot of lube), but the rewards are so worth it.

 What you’ll need

As you start your butt journey, keep in mind that every butt is different. What might be one person’s starting point might be another’s end goal. The amount of time it’ll take to move from a single finger or a smaller toy to a larger-sized toy or anal sex is going to be just as unique as your perfect tush. However, broadly speaking: The more you play and the more your body gets used to the sensations, the faster you’ll be able to train up your butt.  

What types of anal training toys might be right for my butt?

The best toys for anal training are specifically made for anal play. Remember those sphincters we talked about earlier? The outer sphincter pushes things out and the inner sphincter pulls in—literally, it’ll pull things inside once they enter. This is why anal toys NEED flared bases: The flared base prevents it from being sucked inside and stops you from needing to explain to an ER nurse what you were doing on a Saturday night. This is why I’ll only be recemmending specific sex toys, and not a bullet vibrator (or, like, a toothbrush). 

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Don’t be scared of your sphincters, though. Anal training is specifically about learning to relax these sphincters as you gradually and gently increase the size of what enters your anus. 

Anal plugs are not only a great starting point for anal training, but are also a superb addition to sex or masturbation even if you’re not trying to become an ass aficionado. Anal plugs get their name from being sex toys that essentially “plug” the ass, but, more than that, they focus on stimulating the opening and first few sensitive inches of your bumhole.  Plugs are designed to ease into your body and then sit there, which sounds boring, but they’re actually filling your body, rubbing against all your engorged sex organs from the inside. If you look at many plugs, there is a narrow tip that gets gradually larger and a base that tapers back down before the flare. This is great for keeping a plug to stay in place–sphincters squeeze down around the thinner base so it doesn’t move around unless you want it to. 

If anal sex is your endgame with anal training, keep in mind that anal plugs are just the beginning. Since plugs are mostly meant to sit still in your body, they’re the perfect starting point to introduce your body to the joys of anal penetration— but plan on using dildos to practice an in-and-out motion we’ll get into more below. 

There are also many anal training kits out on the market. These can save you bucks buying multiple size toys at once. However, they don’t always have the perfect size for every body, so pick carefully. Most kits come with three plugs, like this Mood Naughty kit, which is perfect for gradually moving from one size to the next. Other kits on the market focus just on girth, or length, or a variety of sizes as well as sensations like this vibrating kit from B-Vibe—douche included!  

What toy materials and sizes should I look for?

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When you’re shopping for a starting anal plug, look for one with a gradual taper like these Mood Naughty plugs that come in various sizes. Remember, anal play is NOT a race—don’t be scared to try something small just to get used to the sensation. That’s the point!

Anal toys come in all shapes, sizes and textures for a reason. Don’t be afraid to explore what else is out there beyond basic plugs as you get more accustomed to penetration. Any anal toy you put up your ass gives you a chance to practice relaxing your pelvic floor and anal sphincters (while getting off). Anal beads and textured plugs give you pops of pleasure. Weighted plugs are amazing to wear during other forms of sex because they offer a “full” feeling while they’re in place during other sexual movement. Prostate toys are specifically shaped to hit the P-spot and can give the wearer a totally different type of orgasm. 

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All silicone toys have a drag to them, and the butt doesn’t naturally lubricate itself, so don’t be scared to add more lube than you usually would. Glass anal toys have less drag and can be easier to pop in and out of your body.

Did I mention lube? We need to talk about lube. Silicone lube lasts the longest and has the most glide, but isn’t compatible with silicone toys. Water-based lubes are compatible with all toys and barrier methods, but absorb the fastest and need to be re-applied often. Oil-based lube is both slippery and hydrating, but breaks down latex and polyisoprene barriers (like condoms). Avoid any numbing lube—pain is an indication that something isn’t working, and anal shouldn’t hurt. 

When should I expect to “graduate” from a smaller toy to a bigger one? Basically… how long will this take?

There isn’t going to be a prescribed timetable for this, as again, every butt is an individual. If you’re up for it, try anal training four or five times a week, keeping the toy (a plug or movement with a dildo) in for 10 to 15 minutes. I would suggest waiting a week or two before graduating to the next size, just to make sure you really are comfortable with the toy you have. The butt is sensitive, so don’t jump from too far when sizing up. Think ¼ an inch at a time. Once a toy feels comfortable entering and exiting your body, you’re ready to size up. Don’t move up a size if there’s any pain or if it’s uncomfortable. 

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Anal training is not a race, and there’s not really an end point. Since your butt is a muscle, it has muscle memory. If, at one point, you’re able to take an eight-inch dildo, and the next time you try it, you’re unable to accommodate those inches, it just means your butt is out of practice. Basically, any time you want to put large things inside your butt, training up to that point first is a good idea.

How to do it

Mentally, you’re ready. You’ve purchased your toy, or you’re starting with fingers, and you’re ready to take your first foray into your bumhole. But where to start? Now that we’ve gotten the basics of beginner anal toys out of the way, what will follow is a step-by-step guide to exploring this particular nether region comfortably and safely. 

1. Clean your hole—and make peace with its other functions.

For many people, taking a shower and cleaning with body-friendly soap is all that’s needed for prep. (If you’d like to take things a step further, ask your doctor if it’s safe for you to do an at-home enema.) Feeling comfortable and at peace with your ass, in all its functions, is a non-negotiable part of any anal play that’s actually intended to be fun and feel good: While poop might scare us, it is a signal that our bodies are working the way they’re intended to. Release your fears about shit, since holding onto that anxiety can keep you from being able to relax, which is a key part of this process. It’s not a sure thing that poop will be involved whatsoever! Also, it’s going to be OK if it is. 

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2. Warm up your hole by getting turned on through touch without penetration.

A crucial part of anal training is getting your ass used to touch and pleasure. The best way for this is to start with massaging the outside of the anus. Lube and fingers (use nitrile gloves if you want the extra barrier, or for easy clean-up to go from anal stimulation to vaginal stimulation) are a perfect warmup. If you’re with a partner, analingus is a one-way stop to pleasuretown. If the idea of a mouth on a butthole squicks you or your partner out, try using a dental dam as a barrier.  

3. Ease into your asshole with your fingers or a small toy and see how you feel.

All right, you’re warmed up, turned on, and feeling good. Time to go in. You can do this with your lubed fingers if that’s where you want to start, but for training purposes I’ll be explaining it using a plug as an example.

Get into a comfortable position. If you’re solo, laying on your side with bent knees might allow you more access than laying on your back. Even though you’ve already warmed up your butt with some foreplay and lube, add more lube. Lube should be on your toy as well as the outside of your anus. Use a lubed finger (if you feel comfortable) to put some lube inside your body—you can also use a lube shooter for this. 

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Take a relaxing breath and start to push the toy inside, slooooowly. Since this is new, don’t be discouraged if it takes five minutes to insert the plug. If it feels like it's stuck or hard to push forward take it out and add more lube. 

Once the toy is inside, congrats!! Take another breath! Masturbate! Have sex! Take a selfie if you’re wearing a plug with some bling on it! Have fun! Try and enjoy the sensation and experiment to see what feels good. 

To remove the toy, take STILL ANOTHER deep breath and don’t rush while you’re pulling the plug out. Add more lube to the outside of your anus. Focus on those sphincters and try to unclench them: taking a plug out can feel just as intense as a toy entering as the end taper isn’t usually as gradual as the taper at the tip. If it feels hard, don’t stress—try again with more lube. 

Do this as often as you want, keeping in mind the more you practice, the easier it’ll become. You could even do anal training daily! Once a toy feels comfortable entering and exiting your body you’re ready to move up a size, keeping in mind, again, it’s a gradual increase. 

General tips

When should I stop if something doesn’t feel right?

Anal sex can feel slightly uncomfortable as your bum gets used to something entering it. Adding lube, experimenting with different positions, being turned on and relaxed can help or alleviate the problem. A sharp or throbbing pain is an indication to pause: Anal sex shouldn’t be painful, and nothing should be forced inside. 

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While the inner sphincter cannot be consciously controlled—it’s an involuntary muscle—with practice, it’s possible to consciously loosen up the outer sphincter. That’s really important throughout your training: Without a relaxed sphincter, anal sex can feel really uncomfortable, and pushing through any pain can cause muscle memory in your body which will make it tougher to relax later on. If you feel pain, take the toy out and give yourself a day or so before trying again. Remember, we’re NOT “working through” any pain. 

No stretching you do will be permanent. Your tissues and sphincters are meant to stretch, as well as bounce back to their original shape. Anal sex is also a mental game: That’s what we’re also working on getting control over, not physically changing our body forever. 

All sex comes with risks. Along with pain, stop play if you see blood. A little bit of blood may not mean you need to rush to a hospital, though: Anal fissures can happen if the delicate tissues around your anus tear. Anal sex can also irritate hemorrhoids, so adding extra lube can help prevent irritation. Still, colon perforation, while super uncommon, is possible. Using ample amounts of lube and listening to you (or your partner’s) body is key. If you bleed—even a little—every time you try anal, talk to your doctor. 

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After any sort of anal play, treat your butt to some aftercare! Besides washing your body and hands, linens, and toys, it’s a good idea to gently wipe around your anus with gentle baby wipes. The area around your anus is sensitive, add a little Backdoor Balm to your delicate tush tissues to help sooth and hydrate your skin. 

Nice. I trained with a butt plug a few times—I even started using a slightly bigger plug! What’s next? 

Now, you’ll get your sphincters used to not only staying open, but the in-and-out motion of anal sex. 

Using plugs where the bases get gradually larger along the length of the toy is a great method for achieving this goal. Once a plug with a larger base enters your body, focus on your breathing and consciously relaxing—this helps you practice relaxing the sphincter while being open. 

OK, I’m feeling like it’s time for butt sex! Anything else I should know?

So now you’re ready to take a dick and/or dildo! If you’re using the latter: Look for smooth dildos that have a girth and length you're comfortable with. Just like with plugs, you are going to want to practice by going up in size. Glass toys are great for sliding in and out of a body. Squishier silicone dildos conform to your body's shape while silicone with a harder density is great for hitting G or P-spots. 

Remember with plugs, how the sphincter closes down around the end of the toy? It’s a different feeling for your anus to stay open around a phallus-shaped toy or penis, especially if there’s a thrusting motion happening at the same time. If you’ve scaled up faithfully and feel good about the progress you’ve made, you and your partner have talked about the need to go slowly and carefully, and you’ve got plenty of lube on hand, it might be time for a fuller guide to anal sex. Go put your anal training to incredible use. You’ve prepared so well for this moment. 

Follow Archie Bongiovanni on Twitter.

Tagged:

sex toys, Butts, Butt Plugs, dildos, Anuses, butt stuff, Lube, Anal, anal sex, Butt-sex, Best You've Ever Had, anal training

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