Chastity Challenges For Male Subs: From Easy To Hard!

Chastity challenges are fun because they really push you physically and mentally. And it's super fun for your relationship as well.

There's nothing like finishing a long chastity lockup for a reward from your keyholder.

Plus, creating challenges for your sex life is a great way to spice things up the right way.

This blog post will share some super fun chastity challenge ideas from super easy to super hard (pun intended).

1. Wear A Chastity Cage For X Days/Weeks/Months

As I always say on Twitter, chastity is a marathon NOT a sprint!

If you are completely new to chastity, start out small before going big.

Just try chastity for a few hours. Your body will need to adjust to being constricted when you try to get hard.

But the body is an amazing micro-organism and it'll adapt with due time.

Once that happens, try wearing your chastity cage for one day (including an overnight wear).

Getting over the overnight wear can be troublesome for some people as it may be hard to sleep if you are a light sleeper.

After that, try one week in chastity.

Before long, you'll be able to wear the chastity cage longer and longer like a real beta!

And if you want a real chastity challenge try to wear it for one month (30 days).

Now, keep in mind that even for longer lockups, you don't want to wear your cage 24/7. It's normal to take it off to clean it for hygiene purposes.

2. Edging In Chastity

Edging in chastity is something you need to experience...

It's so frustrating knowing you're on the edge but can't go all the way to cum. And it's even more frustrating if you use a vibrator against your cage.

You'll feel every little vibration across the's hard to describe but it's basically pure heaven!

You can also have your keyholder tease and edge you as well!

I think that's more fun in many ways.

For example, she can tie you down and do all sorts of tormenting things from sucking your balls to using her nails on your cage, to actually fucking the cage itself!

If you're looking for some more edging ideas, check out this blog post!

3. The Most Humiliating Chastity Challenge?

Your next chastity challenge is to keep a picture of your chastity cage as the screensaver for your phone!

Imagine how nervous you'll get being around co-workers and family/friends.

Will they peep over and see accidentally see it on your phone screen? Would you be embarrassed if they found out?

If you have a thrill for public humiliation, this challenge is definitely for you...

Another super kinky idea is to put a Cuck In Chastity sticker on your phone case. Imagine catching a woman looking at your phone and asking what the symbol means!

Think you could stand doing that? Or would you be too embarrassed? :)

8 Chastity Challenges For Male Subs From Easy To Hard!

4. Humiliating Hump Session

One of the most frustrating things about being locked in chastity is being so close to pussy but not actually experiencing it...

That's why your keyholder should let you fuck a fake pussy.

I find that it's best to use a steel cage as it REALLY digs into your skin while you're humping it.

If you don't have a fake pussy, humping a pillow is just as funny (maybe even more-so).

The challenge is only humping when your keyholder gives you permission. Think about it as a "red light green light game".

When she says green light, you're allowed to hump and when she says red light, you must stop immediately.

10 minutes of this game and you'll be super frustrated like a good sub!

5. Wear A Micro Cage For The First Time

Wearing a micro chastity cage is another great chastity challenge.


Well, for one it's pretty cool knowing your keyholder can put you into an extra small cage if she wants to (i.e. as a punishment for bad behavior).

The other thing is it makes the chastity experience so much more frustrating, annoying, and intense.

A micro cage really makes you so much more submissive and weak for your keyholder. After all, isn't that what is most important?

In fact, I would say it's a pretty big sissy achievement to be able to wear one!

6. Get Pegged In Chastity!

Your next chastity challenge is to get pegged while in chastity!

It is quite the submissive experience - no doubt about it!

Not only are you locked up for your keyholder, but she's taking your ass as well :)

Nothing will make you feel as submissive in a power exchange situation like this.

This is something that ALL men should experience at least once...and maybe multiple times.

And it's even better if she takes your anal virginity. After all, you never forget your first, right?

7. The Chastity Cuckold...

This next chastity challenge is the ultimate cuckold experience!

As I have written in the past, cuckolding is already one of the hottest things you can experience in your marriage.

You'll feel a mix of emotions from excitement to jealousy to humiliation all wrapped into one.

BUT, when you combine cuckolding AND chastity, things go up another level.

There's something sexy about being locked up and knowing it is utterly hopeless as your wife fucks another man and cums on his dick...

You'll have to experience it to REALLY know what I'm talking about :)

8. Cum In The Cage

Your final challenge is to try to cum in your cage.

You have to be a true beta to be able to accomplish this. do you cum in chastity? Well, it helps if you have been locked for at least 4 or 5 days as you'll be super horny at this point.

Your balls will be full of cum and very sensitive as well. This makes it easier to cum and when you factor in anal stimulation as well, things can get pretty crazy!

The sensation is hard to describe but it's pretty much the worst ruined orgasm you'll ever get haha.

Chastity Challenges For Your FLR: Final Thoughts

Overall, having some challenges/games like this in your FLR is a great way to spice things up.

It's certainly better than leading a boring sex life.

Hopefully this list gave you some fun ideas to try with your partner.

So, which challenge do you want to try the most with your keyholder? Let me know in the comments!


  • I am edged to tears twice a week while being cleaned. I beg for a release ut she just laughs and puts it back on me. Eight years caged with nothing more than a ruined orgasm or prostate milking and never again will I experience the inside of a pussy.

  • OMG, I’m still shaking from my latest edging session at the delightfully cruel hands of my mistress.
    Having been locked up for close to a week with lots of teasing, reading your blog inspired her to edge me without removing my cage. With some ingenious inspiration she cupped my aching balls around the cage and wanked them in the same way she would wank my pathetic little clit, only much more satisfying for her as she could actually grip onto something worthwhile.
    The pain was exquisite, and combined with the frustration of no physical contact for my clitty drove me to the edge in no time!!
    Needless to say, no release was granted and I am remain locked up indefinitely…..

  • As a male masochist I submit to humiliation, pain and control. I need it!

  • i like to lie under my Goddess’s booted feet while locked in my steel chastity cage. It’s the ultimate pain/pleasure when she steps on my locked boy clitty, especially since my balls are exposed for Her to step on!

  • Yes very very good


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