Alas, anal play isn’t like cornhole. It takes more training—an ongoing rehearsal dinner of fingers, toys, more fingers, and conversations with both yourself and your partner(s) about what feels good—and what can feel even better. “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,” explains Archie Bongiovanni in VICE’s “How to Train Up Your Butt for Anal Sex of All Kinds.” Every sphincter is a star. Every pursed bumhole, a possibility. “Not only do they look great,” says Bongiovanni, “but they’re also full of nerve endings, meaning anal sex can result in some bomb orgasms.” With a a lot of self-love, lube, and some anal education, you, too, can get there.
As Bongiovanni explains, you actually have two sphincters in your butt: “an inner one that you can’t control, and an outer sphincter that can be taught to relax, to open, to let pleasure in." It takes time to show that outer one how to have a good time, and to help it grow accustomed to accommodating big stuff. PLEASE: Don’t stick just anything up there. Your inner sphincter is a powerful, wonderful part of your body that can suck up whatever goes in like a sandworm in Dune. That means having a “flare” or wider handle/end to the part of your butt plug that doesn’t go inside of you is essential. No one wants to be the guy who butt-births a bottle of Garnier Fructis at the ER.
It’s so important to go into anal feeling relaxed, cared for, and with an open mind. Start slow, by lightly tapping or licking your partner’s primped rear. Remember: Lube is your friend. If your partner has a penis, try lightly knuckling the perineum (that spot between the penis and balls), and sliding a finger in there. “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,” advises Bongiovanni. The right breathing exercises, changing of positions, and time is key. You can’t cram in the training, and become an anal aficionado overnight. It takes time, patience and often the right set of graduated, glass butt plugs to get there. But once you are there? WELL. There’s a whole new world of backdoor pleasure that awaits, from the weighted sensation of being filled with a metal or glass plug, to the vibrational pleasures of a remote-controlled, anal toy. Anal isn’t for everyone. But until you’ve lowered the drawbridge… how do you know?
Consider the following sex toys, anal beads, butt plugs, and accessories like a road map. Start off with the essentials, and explore your options in texture, size, and sensation. Find an anal plug—or three—that fits your particular, 2021 edition of being a vaccinated, horny cicada. Bottoms up!
Lube the tube
Get to know your lubes. If you’re just fingering down there, you don’t have to worry about lube-toy compatibility. But, as Bongiovanni says, understand that while “silicone lube lasts the longest and has the most glide, [it] isn’t compatible with silicone toys,” and while “water-based lubes are compatible with all toys and barrier methods, [they] absorb the fastest and need to be re-applied often.” Oil-based lubes are some of the slipperiest out there and most-hydrating, he says, but can break down latex. If you’re dizzy from those deets, try testing the waters with an ~aesthetic~ lube duo (one is organic, the other is silicone) for the nightstand by Maude, which is like the Aesop of lube-makers.
Shine Duo, $20 at Maude
Baby’s first butt plug
… Should be a small, tapered toy made out of glass, which is one of the easier materials on the bum. It's as smooth as it gets, and also great for temperature play, perhaps a little bulbous for a first plug, but we know you’re here to train that anus. That also means getting a toy you have chemistry with—and perhaps, in the immortal words of 311, “Amber is the color of your energy?” This glass anal plug looks nice enough to leave out on the nightstand or bathroom shelf, leaving your lover to wonder if it was spun from tree sap. (Or was it stolen from that old dude’s amber cane in Jurassic Park?) The mystery of it all...
Glas Over Easy Butt Plug,
$38.99 $25.29 at Ella Paradis
You’re more of a metalhead
The “stainless” aspect of stainless steel has never held more weight, in our hearts and our bums, than now. This metal beginner’s plug comes with either a purple or “diamond” bejeweled tip, in true pirate beauty fashion, and is also great for temperature play.
Iconic Brands The Silver Starter Bejeweled Plug,
$14.99 $9.79 at Ella Paradis
You came here with a long-haul strategy
God, we love people like you. You came here with a plan, and with just enough tapered, beginners anal plugs to Goldilocks your way into finding out which size works best for you. This glass set will train your bum, and help you discover if you’re craving more texture, weight, or length up there. They’re a butt boudoir staple, and no matter what plugs or sex toys you may move on to tomorrow, they’ll always be there for you whenever you want to step in or out of anal play. They’ll also definitely have you at full tentacle-plug play by the holidays (so here’s an idea: use them to make a nativity!).
Adam & Eve Booty Boot Camp Training Kit, $29.95 at Adam & Eve
The gateway plug to anal vibrations
See how narrow this plug is? Different bums have different needs, but this is generally what a beginner should be looking for. First time users, consider lubing this tapered toy up and playing with it vibrationless. Then, you can explore its six remote-controlled vibration levels and [MTV airhorn] 15 patterns. Once more, for the horny bros in the back: This toy is remote-controlled, so you can amp up your lover’s vibe whilst checking in on your other duck à l'orange.
B-Vibe Novice Plug,
$223.99 $152.89 at Ella Paradis
You’re ready for a thicker vibrator
Same as above, but a tad thicker and with 10 functions for folks who need fewer bells and whistles (and more girth).
Butt Tingler 10 Function Vibrating Butt Plug 3.5 Inch,
$24.99 $24.99 at Lovehoney
You’re ready for a thicker, textured vibrator
That’s where the Firefox browser fox went! This plug is on the thicker side, but its swirly texture makes it a solid transitional plug for slowly twisting up into your bum, much like you’d open a fine bottle of wine. Search, explore, and browse through six different vibrational patterns, on land or in the tub (it’s also “splashproof”). Plus, it’s $50 off right now.
B-Vibe Swirl Textured Butt Plug (Medium),
$170.99 $114.09 at Ella Paradis
The Cadillac of remote controlled prostate massagers
LELO is the maker of some the best luxury sex toys on the market (have you seen the brand’s latest G-spot-clitoral vibe? it’s pretty sick), and beloved by people who enjoy quiet, high-design sex toys that will look great sitting casually on their copy of Robb Report. Naturally, LELO’s remote-control prostate massager—sorry, Hugo—is a testament to that quality-driven engineering. There is not one, but two powerful motors, “one vibrating deep inside and the other offering external perineum stimulation,” and the remote works up to about 40 feet (12 meters) away. Of course it’s waterproof, so bring it on the Sea-Doo.
LELO Hugo Prostate Massager, $219 at Babeland
The prostate massager made of Cool Whip
Finally! We love all the sporty, bike-seat-looking prostate toys. But we were also waiting for one that looked like it was carved from the errant, free-falling cum of a god on Mt. Olympus. The trident shape of this prostate massager is flexible, ample, and easy to hold, yet it wrangles three inches of curved girth for hittin’ that prostate just right. Zeus would never. (But also, he would.) .
Aneros Helix Trident Prostate Massager, $54.99 at Lovehoney
The vibrating strap-on
Once you’re ready for full penal and/or wand penetration, opt for a smooth dildo like the Siren. It comes with an optional, insertable bullet vibrator (when you’re ready), but its even, smooth texture lets you glide into deeper anal penetration. Note: also great as a strap-on.
$119.99 $89.99 at Babeland
You own a cloak, don’t you?
A bulbous or textured surface is going to be a little next-level when it comes to dildos. This curved one is just so enchanting, and (when properly cleaned and sanitized) can go right up a partner’s vagina—or front butt, as a Midwestern mom once said—as well.
Beaded Sensual Glass Dildo 7 Inch, $39.99 at Lovehoney
Forget the pearl necklace
It’s all about the bread crumb trail. Anal beads are a pretty straightforward, bendy little string of graduated, insertable pleasure that can add a little zhuzh to your climax when sloooowly pulled out at the right time. This is indeed a long, tall Texan of a set—but just look at how small the first bead is. This is a string to explore over time, and grow old with.
Lovehoney Classic Silicone Anal Beads 10 Inch, $16.99 at Lovehoney
Find your kink
So, this is cursed. But we love cursed sex toys (no kink-shaming here)! And now we can know what Ariana Grande feels like when she rocks that pony tail through performance antics. Rest assured: This 24-inch, beflamed faux-hair ponytail is also easily washable. Just “hold by the plug end and brush from plug to end, just like you would your own hair.” As one reviewer wrote, “Ein schönes langes Pony Tail. Sehr schön.” A long, beautiful ponytail. So beautiful. See you at the trough.
Vegan Flame Ombre Pony Tail Butt Plug, $52.99 at Etsy
The whole smorgasbord
Look around, you seasoned butt player. All of this [gestures to ~chocolate~ factory] is yours with a kit like this one, which comes with all you need to stay primped, prepped, and pleased. There’s a static butt plug, vibrating butt plug, graduated anal beads, and a douche for porsterity.
Fifty Shades of Grey Pleasure Overload Starter Anal Kit (4 Piece Kit),
$87.99 $58.79 at Ella Paradis
Protect ya bed
The scope of sex furniture is so rich, and there’s truly a pillow, couch, or wedge for every form of sexy time out there (see: the Nugget After Dark community). We know you already have a blanket to lay down for anal play, but wouldn’t you rather have a smaller throw that is stain-proof, moisture-proof, and can be easily tossed into the laundry machine at warp speed? Think of it like a soft, velvety butt bib.
Liberator Fascinator Throw,
$191.99 $126.99 at Ella Paradis
Have the wipes on hand
Think about it: Adults use wipes for our faces, stainless steel appliances, tile floors, electronics—so why did we suddenly decide to stop keeping our rears extra clean? Seems like a weird transgression from babydom, IMO. Keep these on hand, and love yourself more. “We made sure they’re pH-balanced,” explained the makers at Cake, “and added honeysuckle for skin softness.” As if that wasn’t thoughtful enough, they also come in on-the-go packets for when you want to do anal stuff in the PT Cruiser.
Bottoms Sexual Play Cleansing Wipes, $12 at Cake
Now that we’ve set the scene, let’s roll up those sleeves!
The Rec Room staff independently selected all of the stuff featured in this story. VICE may receive a small commission if you buy through the links on our site.