The Massive List of Butt Plug Challenges

If you’re looking for butt plug challenges, you’re in the right place. Maybe you just got your first butt plug and you’re looking for ways to incorporate it in your sex life. Or maybe you’ve been playing with butt plugs for years, and you’re looking for ways to spice things up a bit.

Whatever your reason, you’re in luck. I had a ton of fun brainstorming ways you can use your butt plug—you’ll find over 10 in this list, and I’m sure that you’ll come up with more once you start thinking about it. Butt plugs really are awesome, versatile, devious toys.

You can complete most of the challenges in this list by yourself, but some of them will require a partner. (All of them can be done with a partner—some of these’ll work exceptionally well as part of a BDSM dynamic.)

I’ll be adding challenges and training ideas to this list over time—so it’ll grow and get better. If you think of a challenge that should be added to the list, or you try one of these out, share it in the comments or send us a message! We’d love to hear from you.

Creative butt plug challenges

Complete these challenges as written, or use this list to launch your own brainstorming session. No matter how you go about it, I hope they bring you plenty of enjoyment!

These challenges aren’t in any particular order, and some are definitely more advanced than others. Just be aware that you might have to work up to some, or modify them to suit your experience and comfort level.

Challenge 1: When in doubt, add a butt plug

Difficulty: Easy

Your butt plug doesn’t have to be the focal point of your play session. No matter what you’re doing, you can probably find a way to incorporate your plug.

Compared to some of the other challenges on the list, this is a pretty tame one—one that you’ve probably already tried. But that doesn’t mean it’s not good.

This challenge is simple: make a list of five sex acts you enjoy, then try them again, this time with a butt plug.

It really doesn’t matter what’s on your list. Here are a few ideas:

• Plain ol’ missionary sex: whether you love it, or whether it’s getting a bit boring—next time try it while wearing a plug.
• Into impact play / love to be spanked? Someone on all fours with their butt up is inviting. Now imagine that, but add a plug. Flog away!
• Oral really do it for you? The next time you’re getting some, try it while wearing a butt plug.
• Masturbation (however you do it!)
• Have your partner give you a sexy, relaxing massage, and work the butt plug in as part of it.
• Like the feeling of hot wax? Imagine how intense the sensations might get when you feel the wax at one part of your body while simultaneously feeling the plug.

. . . you get the point. The idea is that you can find some ways to add another layer of sensations to something you already enjoy. Who knows? That thing you love could get even better.

This is a great way to get to know yourself, especially if you’re a beginner. Not everyone loves butt plugs in every scenario, and unless you try them out you’ll never know what works for you. Butt stuff can feel a bit strange at first, so pairing it with another sensation you love can help you enjoy it while getting used to the new sensation.

But this is a healthy exercise for more experienced people too. Lots of times we can learn a thing that feels good, then lean on that. Making the list and working through it intentionally can help you be present in the moment and enjoy the experience anew, even if it’s one you’ve done it before.

Challenge 2: Walk around the block

Difficulty: Easy

This challenge is simple: insert a butt plug—the bigger the better (I’ve actually done this with the Tantus Tex)—then go for a walk around the block.

Public play and fear of getting caught are huge turn-ons for a lot of people, but it can be hard to find ways to dive into those interests without running into safety/legal/consent/moral issues. This challenge can help you some of those experiences without the issues. No one has to know you have a huge butt plug in as you walk past them. But you will, and that’s enough.

Of course, you don’t have to be into public play to enjoy this challenge. The sensation of walking while wearing a plug is intense on its own.

As an aside: if you have a partner, they might enjoy getting in on this. Personally, I think it’d be incredibly hot to go on a walk with my partner while I knew they were plugged. Every slight squirm and bit of eye contact would add to the sexiness of the situation, not to mention play into a power dynamic if that’s your thing.

Once you’ve completed this challenge, step it up a notch with challenge 3.

Challenge 3: Go out for dinner while wearing a butt plug

Difficulty: Moderate

Dinner just got a whole lot more interesting.

If you’ve successfully completed challenge #2, try taking it a step further and going out for dinner while plugged.

You can easily change this one up to your level of comfort. Maybe instead of dinner, you run an errand or grab a coffee. The point is to move past a quick walk and into a longer, more involved activity. The largest plug I’ve used for something like this is the Split Peaches Grenade (Large).

Challenge 4: 24 hours plugged

Difficulty: Advanced

How many people can say they’ve worn a plug for a whole day? Not too many. But this challenge is your chance to be one of those few awesome, liberated people.

Wearing a butt plug for 24 hours will probably keep you in a state of slight arousal all day long. But it’s a long time, and it presents another interesting problem: can you make it through the night?

Some people just love wearing plugs long-term, and this is a super sexy way to try it out.

Here are some tips to help you pull it off:

• Make sure you use a plug you’re comfortable wearing—choose a small one you’re really familiar with.
• The base of your plug should not pinch or be uncomfortable between your cheeks.
• Use a long-lasting, thick lube, and reapply as necessary.
• Choose a day where you won’t have to partake in too much physical activity.
• If it starts to get sore or hurt, stop! It’s not worth hurting yourself for a challenge. You can’t expect to do everything on the first try, so listen to your body and be patient with yourself if you have to stop.

Of course, this challenge can also be modified in lots of fun ways. An easier version of this challenge would limit it to 12 hours. If you’re playing with a partner, you might consider adding in random check-ins throughout the day. If the plugged party doesn’t send back “proof” within 10 minutes, maybe an hour gets added to the total time they’re left plugged.

Challenge 5: The time-bomb

Difficulty: Varies

If you’re not careful, this challenge could get rough for you: real rough.

Your plug is a time bomb, and to keep it from going off you have to defuse it by thrusting it in and out five times every 30 minutes before putting it back in.

• If you want easy mode, you have to defuse it four times. (After 30, 60, 90, and 120 minutes.)
• Moderate: 8x (4 hrs)
• Hard: 20x (10 hours)

You can modify this challenge is so many ways.

What if you forget to defuse the bomb? There should be a consequence. Maybe it means tacking on another hour or incurring a penalty of 100 thrusts for each missed defuse, that pile up at the end.

Or maybe you modify this challenge by swapping out the time bomb—maybe you have to change the plug you’re using every 30 minutes. This could play out in a couple of ways: If you get to pick the order you go in, do you start with that big one, or leave it for last? Or maybe you don’t get to choose, and instead you have to gradually work through a series of  butt plugs that increase in size. After defusing each plug, you move up to a larger one.

Be devious and use your imagination. There’s so much room to take this in different directions depending on what you enjoy.

Challenge 5: More than just a plug

Difficulty: Varies based on butt plug size

If you’re really interested in stretching and getting to a more advanced level, you’re probably going to want to do this challenge at some point.

The shape of butt plugs keeps them in, but it can do much more than that.

In this challenge, you’re going to feel all of that shape—100 times.

First, choose a butt plug that you’re comfortable with. One you’ve played with before—ideally one that provides a stretch, but can still be inserted without too much fuss. Cover it (and your hole) with lots of lube—you’re going to need it.

The game is simple: relax, then push in the plug. After it’s fully inserted, pull it out as quickly as you can comfortably. Once it’s all the way out, send it back in.

Repeat 100 times, counting each thrust out loud. You just turned your plug into a dildo.

Of course, the experience is vastly different than what you’d get with a cock or a dildo. You’ll feel your hole expand and relax to accommodate the unique shape of a butt plug with each thrust.

If the idea of being relaxed, gaping, looser, and ready to go turns you on, this is the challenge for you. Over the course of the 100 full thrusts—make sure you’re going all the way out and all the way in—you’ll get more and more relaxed until the plug slides in with little resistance. Oof.

Challenge 7: Getting cold

Difficulty: Easy

Do you have a glass butt plug?

In this challenge, you’ll use the material to your advantage (or disadvantage . . . depends on how you like it.) Either way, it’s worth trying out one of the benefits of your plug’s material; you have a chance to experience a new sensation.

Put your glass plug in the freezer for 20 minutes, until it gets nice and cold. Coat it throughly with lube, then ease it in.

It’s not for everyone, but playing with temperature is something you have to experience. A cold butt plug is . . . well, there’s nothing quite like it.

Challenge 8: The stair-stepper

Difficulty: Easy

What’s a motion that will put extra focus on the fact that you’re wearing a butt plug? Climbing a set of stairs.

For this challenge, you have to climb 200 stairs while wearing a butt plug. For maximum effect, choose the largest plug you can handle. You’ll be fighting the sensation that the plug might fall out in an intense battle against a set of stairs.

Make the challenge harder by increasing the number of steps, requiring a thrust in and out after every # of stairs, doing it naked (within your own home, of course), requiring the steps to be done via crawling instead of walking, or making any number of other devious adjustments.

Challenge 9: Jumping jacks (what is this, gym class?) 

Difficulty: Moderate/difficult

Find the biggest plug that you can handle. I know I always say use a ton of lube, but I really mean it this time. Fill your hole with lube, then thoroughly coat your toy. Then do it again. You want to be drenched. You’ll learn why in just a moment.

OK—once the plug is in, strip naked if you’re not already, stand up and do a little stretch. Then it’s time to exercise.

Do 50 jumping jacks. You’re not allowed to touch the plug. If it falls out or you touch it, you have to add 10 jumping jacks to the remainder.

Don’t skimp on your jumping jack form. If your partner is interested, they might have fun critiquing your form and making sure you don’t cheat.

This is a brutal challenge. If you have a sufficiently large/heavy plug, you’ll feel it start to slowly slip out on its own during the jumping jacks. And there’s nothing you can do about it. When I tested this challenge, I used the Tantus Ringo—that plug is prone to slipping anyway, so I was jumping for a long time.

Challenge 10: Addicted to your cell phone

Difficulty: Easy/moderate

This is a devious challenge, because its out of your control. Start with 2 hours: every time you get a text, you have to add 10 minutes to the time left wearing your butt plug.

Will you respond, and risk getting into a conversation that leaves you plugged for hours?

Other challenge ideas

• Complete a yoga session, plug inserted. I recommend doing this one at home.
• When you’re modifying a challenge or creating a new one, think about incorporating dice. Each roll can mean something, and each number produce a varied effect. That way, it’s not up to you. It’s the dice that decide what happens.
• Wear a plug while cleaning your house. This can take a boring chore and turn it into something fun and sexy. Just don’t think about it too much, or you won’t get any cleaning done.
• Spend too much time on social media? At 8:00 pm each day, look at the breakdown of websites you’ve been on. There are apps and browser extensions that track can this for you. Add all the time you spent on social media together to get the amount of time you have to wear your butt plug that day. Be careful—too much time, and you’ll be wearing it all night!

Sex should be fun. And butt plugs can definitely make it even more fun—especially if you use them in the right way. These challenges are just a way for you to start thinking about other ways you can get even more out of your sex life and discover new things to love and enjoy.

What are your favorite butt plug training ideas and challenges? Share them in the comments below for others to try!