30 Day Chastity Training Program

Welcome to my 30-day chastity training program, this is for those of you looking to challenge yourself with your cock cage. Looking for a new way to push your boundaries and make yourself feel amazing and accomplished.

Inside this training program, you will find 30 whole days of challenges for you to complete. Except these aren't any kind of challenges these are specifically to do with chastity and caged cocks. You can do this challenge solo or with a keyholder present, it's up to you, but whatever you choose have fun, be safe and good luck because this chastity challenge isn't easy.

What You Need:

list of things you need for the chastity training program

You are going to need a few things to start this chastity training program and I have left those below. Some are just recommended and others are definitely needed to complete this program.

  • Lubrication (Needed) – Lube is very important, I like this water-based lube as it's safe to use with any sex toy. Remember to avoid silicone lubes if your cock cage is made of silicone as it will damage it.

  • Cock Cage (Needed) - This is my favorite cock cage to use with my caged cocks. It fits most men, it's strong, durable and does the job of containing your mear very well.

  • Timer (Needed) - Use your phone or clock, anything that can keep time well and efficiently.

  • Butt plug Training Kit (Recommended) -It's not 100% necessary but I recommend a butt plug training kit to help you train your ass and get the most from anal play.

  • Accountability (Needed) – If you don't have a keyholder who can do this for you, feel free to use the comments below to hold yourself accountable and complete this chastity challenge.

  • Self-Timing Key Box (Recommended) - This isn't necessary and is more of a luxury but a self-timing key box holds your key for you up until the timer is up. This ensures you don't get access to it a moment too early.

  • A 6-inch dildo - (Needed) - My favorite size for male anal play, this dildo will bring you delicious prostate stimulation and lots of exciting erotic fun. I also use this dildo all of the time, it's such a great addition to my toy box.

  • An 8-inch dildo - (Recommended) - With my challenge, you will be using your ass at times, and if you want to put yourself to the test, enjoy an 8-inch dildo whenever prompted to use a dildo.

  • A mega 10-inch dildo – (Recommend for thrill-seekers) - If you want to push yourself to your limits, a 10-inch dildo will put your ass and mind to the ultimate test.

  • Butt plug – (Needed) - You're going to need a butt plug like this one that vibrates during this challenge and you're going to love it.

  • Panties – (Needed later on in the program if you decide to do the femdom challenges each day) - This is an optional item that you're going to need, if you're not into femdom, skip this one.

  • Bra – (Recommended) - A bra is recommended to complete this chastity challenge but not to worry if you don't have one to hand because you can improvise and use your imagination.

  • Nipple clamps (Recommended) - You are told to put on nipple clamps during your challenge if however, you don't want to have real ones, feel free to use clothes pegs.

  • Stockings - (Recommended) - I love my caged men in stockings and if you want a truly chastizing, all control gone kind of experience get some.

  • Nail polish – (Recommended) - This can be picked up for really cheap at virtually any store, it isn't essential to this challenge but it is a nice bonus to some of the more feminizing daily challenges.

  • Wand vibrator (Needed) - This vibrator is needed during a few of your chastity challenges. It's used to tease, make you cum and drive you insane.

  • Summer dress – (Recommended) - Not a must-have but a great addition to your arsenal for this chastity challenge. You will see why when you explore the challenges for yourself.

Rules Of Training

sign that says stop and text that says my chastity rules

There are some rules which must be adhered to:

  • If you don’t have the items try to improvise, if you can’t improvise, pick a punishment from this list of chastity punishments.
  • Days must be completed in order.
  • If you don't wish to participate in one of the days for a legitimate reason, this is the only time you may skip to the next punishment and you can only do this once, so pick wisely.
  • If you can't sleep in your cage, spend the whole next day locked up before continuing with the next day of the challenge.
  • If you accidentally cum during any of the challenges, ruin your orgasm, and have 3 days of cold showers (minimum of 30 seconds).

Safety Disclosure: This is a game, it’s for educational purposes only, don’t try anything, if you do, you do it at your own risk. Wearing a cock cage can be dangerous and cause life-changing issues. Be careful, do your own research, and anything you do, you do it at your own risk. Wearing a cage at night can be harmful, do your own research, if you can’t do it, just spend the following day locked up for the whole day.

What Will Happen During And After This Self-Chastity Training

examples of before and after doing chastity training

This is a completely free chastity training system, this is the same training I use for anyone I keyhold for.

I could charge for this, but I want more of you to experience what it’s like to be under me and be my chastity slave.

In the next 30 days, you will be told exactly what to do, you will have to completely submit to me and you will probably do some things you really don’t want to do. I want to train you to be a sub, a good caged sub who follows rules and wears their cage when they are told to.

Before you start, I want you to write your own contract on a piece of paper exactly like this:

Chastity training program contract.

chastity contract

I will follow this challenge for the entire 30 days. I will listen to all rules and commands and understand my cock is no longer under my control under I complete this chastity challenge.


Printable image:

This is a novelty contract, but it is to make sure you take accountability, I’m not there so I can’t make sure you do as you’re told, however, you just signed it and so now you’re locked in, and ready to listen.

If you don't already read my blog, my name is Jess and I love to write about sex (as well as have it and watch it, duh!), I also love chastity, and creating this free chastity challenge was a big deal for me as I wanted more caged lovers to come forward and enjoy something that will make them seriously submit to me and may even turn them into a sissy, cuck, or a permanent chastity wearer. It may also make them only be able to cum when wearing a cage, it might make their cock shrink, who knows? All I know is that I love chastity and this challenge is going to blow your mind and give you 30 days of pure caged pleasure.

Chastity Training Program:

before and after chastity

The first 5 days are the warm-up, after that, it gets more advanced as it each day progresses.

Warning: This may turn you into a sissy, a cuck, and a chastity wearer for life. Good luck and let me know how you get on! ❤


Day 1.

It’s time to warm things up.

You need to have a full shower, trim your pubes and put your cage on.

I assume this is the first time you’ve worn your cage, you can use this guide to learn how to put your cage on.

Today you need to wear your cage for a minimum of 2 hours. No orgasm for today. Set a self-timer for 2 hours and only release it when it's up.

You can wear tight boxers, it makes the cage lighter to wear.

Take a before picture and an after picture, so we can see the shrinkage after the challenge, you can even do some cock measurements to be sure of any shrinkage.

You also need to add a daily shower and cage clean every day to your schedule. This must be done every day from this point on if not already specified.

Day 2.

Wake up nice and early, 7 AM is your wake-up time.

Put your cage on first thing in the morning, before you make your bed before you have a coffee, it’s got to be the first thing you do.

Now, once it’s on I have some chores for you to do. Remember, you have to say thank you miss, after every chore is complete, out loud:

  1. Make your bed.
  2. Brush your teeth.
  3. Have a glass of water.
  4. Have a tea or coffee.
  5. Wash every piece of cutlery you have.
  6. Put some clothes on.
  7. Wash all your plates, Bowls, and china (take your time, this is a deep clean).
  8. Clean all the floors in your house, every bit of flooring even under your bed.
  9. Eat some food, thank me before and after.
  10. Wear the cock cage for 2 hours once everything is done.

This is all about learning to follow the rules of a superior woman.

No orgasm today for you either.

Day 3.

It’s the third day of this challenge and I hope you’re feeling horny. Again, another early start, 6:50 AM, and putting your cage on must be the first thing you do.

It’s not time for you to cum yet. Enjoy a 3 hour lock-up time for you today, on top of the below time of 30 minutes.

Once your cage is on it’s time to write down what you’re grateful for about this challenge.

Write down everything that you love about being in chastity and why you wish it could last longer.

Now read out loud everything you have written.

This should take no less than 30 minutes, if it does, keep repeating what you wrote out loud.

Make sure to also watch 20 Minutes Of Porn while caged, no touching your caged cock at all.

Watch this type of porn: cum compilation, chastity, cuckold, sissy, dominatrix, pegging, or worship.

From this point on in the challenge, you will only pee sitting down, whether you have your cage on or not. Take this time to learn how to pee as a chastity slave. Take your time, tuck your caged cock in between your legs and get going.

Day 4.

Chore Day again.

-Wake up early (7 AM)

-Cage yourself

Today is a 3-hour timer for your cock cage excluding the time it takes you to do your chores and your 30 minutes of edging below.

Do these chores in this order:

  • Clean your bathroom (toilet, washer, shower/bath, clean it spotless.
  • Clean your kitchen, every part of it.
  • Wash your clothes.
  • Change your bedding
  • Scrub the bottom of your main shoes clean, use a toothbrush for extra points.

Say thank you miss, before and after each task.

Remember to only pee sitting down.

It’s time for you to learn to edge.

Go to this site, enter these settings, and for the next half an hour you’re going to edge yourself with your cage on:

Game duration: Min/Max 30 mins

Probability of an orgasm: 0%

Probability of a denied orgasm: 100%

Ruined orgasm: 100%

Edging: 100

Cooldown: 5 seconds

You’re not allowed to orgasm if you do, you must punish yourself by spanking yourself with your paddle.

This is about learning restraint.

After the half-hour is up, say thank you miss and be happy that I let you have this moment.

Day 5.

It’s about to get a lot harder, you’re going to earn your minutes, hours, and days in chastity in the next few weeks.

To mark this momentous occasion today is your first release day in 5 days.

You don’t need to wear your cage today, make the most of it.

Clean your cage, re-trim your pubes, exfoliate your body in the shower.

Today is also a day for taking a progress picture of your caged cock. Go ahead.

You can have your first orgasm in five days, the only rule is you have to edge for 1 hour before your orgasm. Set a timer and make sure you edge for the entire 60 minutes.

Cum before the hour is up and it’s cold showers for the next 3 days, every day.

Day 6.

You must cage yourself up from the moment you get up.

You must be in chastity for at least 8 hours today.

Pick a random number below 100, got it? Now go to these chastity challenges, you have to do the challenge you picked, too extreme? You get to pick a different one at the cost of adding another 5 hours of chastity time on top of today's 8.

If it lands on one that uses an item you don’t have to move on to the next.

You should be nice and relaxed from your orgasm yesterday, lets change that with 20 minutes of femdom porn at some point during your 8 hours of lock-up today.

Say, thank you miss keyholder, thank you omgkinky, thank you, Jess, 100 times in a row, lose count? start again.

Day 7.

Mmm one of my favorite days of this challenge!

It's butt plug training day!

Your butt should not have been penetrated one bit so far, it’s time to change that with some dildo training. If you need any expertise on taking an anal sex toy read this guide.

Get your small butt plug from the kit, you have to wear it for at least one hour today while in your cage.

8 hours total cage time. I’m being really kind, everything in me wants to give you 9 hours, but I’ll hold back for today.

Day 8.

Dildo training day starts today.

Caged for 9 hours, I added the extra hour for the 20 minutes of fun you're going to have with your ass.

You did so well with the butt plug yesterday, it’s time to try a real dildo in your ass.

I want you to practice taking a 6-inch dildo up your ass for 20 minutes. I want it all of the way in.

You have to be caged the entire time.

You can’t have an orgasm or else you must spank your balls 10x.

Remember to thank me properly, before and after the dildo enters you.

Day 9.

First full day in chastity along with a brisk walk, it's time to go out in public wearing your cage.

Nothing more, nothing less.

You must secure your cock into your cage the moment you wake up, all day, during your walk, and up until the time you go to bed.

You may clean your cage and have a shower before bed.

Day 10.

Welcome to day 10, this is butt plug training day.

Insert the medium size from your kit and keep it in your ass for one hour while caged.

You can have a release twice today, BUT you must ruin both orgasms. The second you cum, let go of your cock. Say out loud once you ruin your orgasm, thank you for letting me cum, mistress.

You only have to do 5 hours in locked-in chastity today.

I also need you to take some before and after pictures of your cock in and out of the cage on day 10.

Day 11.

Today you are banned from wearing underwear and you will be caged for an entire 10 hours. You must also complete these chores whilst naked and wearing just your cock cage:

  • 100 Jumping Jacks.

  • Use a spanking paddle on your ass 25x.

  • Wash every plate in your house.

  • Write 'I love my cock locked up' 500 times.

You’ll probably start shrinking in that cage with all the time you’re spending locked away.

Day 12.

Early start for you! Get up at 6 AM and start the day right by cleaning your cage and cock, thoroughly.

The second it’s done, it’s time to put it on for the whole day, that's another 10 hours of complete lock-up.

Watch 30 minutes of one of these porn categories:

  • Cuckolding

  • Femdom

  • Dominatrix

  • Edging

Absolutely no touching your cock whilst watching your 30 minutes of porn and pay attention to it, no looking away.

If any precum leaves your cock, make sure you try it, see what it tastes like.


Go on a nice long walk with your cage on and this time you’re not allowed to wear any underwear.

Day 13.

Today feels like another 10 hours in your cage

However, uncage your cock, put porn on for 20 minutes, and remember you must not get an erection.

If you get an erection, put your cage back on for 5 minutes, and then try again. Do this until the 20 minutes is up. It’s good to learn not to get aroused all the time, silly boy.

After the first 20 minutes, it’s time for a reward, you can edge for 30 minutes with no release before putting your cage back on for the remaining hours you have left.

Day 14.

Start the day by writing 'I have a small cock' 500 times on a piece of paper.

You can take your cage off for 10 minutes and in this time I want you to try and make yourself cum without using your hands, you can rub against items, just be sure to when you orgasm (if you can) you ruin it, you stop all movements, everything and you just let the cum pour out of your poor cock.

Once the 10 minutes are up, get your large butt plug. I want you to work on using the large butt plug today, if it doesn’t fit yet, go back down to the medium size we used before. Wear it for one hour.

After that get your anal dildo out and it’s time to do deep, full thrusts, every thrust you do say 'thank you miss', during which you must be caged up and you must do at least 10 minutes of thrusting.

Enjoy this, because we will be going up to a bigger dildo size soon.

Day 15.

You get to spend only 4 hours of the day in chastity, but it’s time to spend your first night locked up in your cock cage.

You can have one orgasm today, but you have to clean it up after. You have to cum into your hand or onto your body, you can even give yourself a facial, but you must clean everything up after so that you're spotless.

Don’t want to clean up so thoroughly? don’t cum.

Make sure to also measure your cock, take before and after pictures and see how little you’re getting.

Day 16.

Take the cage off in the morning for 1 hour when you wake up and then get yourself back in it for the rest of the day.

Today I’m ignoring you, don’t mention the cage to yourself or anyone, just ignore that it’s on, don’t even think about it. We’re going to just forget about you for day 16.

Do not sleep in the cage, tonight you get the night off.

Day 17.

5 hours of chastity during the day and then tonight you sleep with your cage on.

I am going to need you to write a comment down below or send me a message about your experience so far and title it: Day 17.

That's not it, today is time for another anal training day and you have a BIG challenge:

Start with 30 minutes in your pick of butt plugs. Then it’s time to try out your 8-inch dildo.

Remember go slow, say 'thank you mistress' when it enters you, and thank you with every deep thrust you take.

How much can you fit? Hopefully, after 30 minutes you can fit every inch.

Feminization also starts today.

This isn’t really about if you want to or if you’re into it, it’s more about doing as a dom tells you. I’m your dom and I’m telling you to do this.

Femdom challenge:  You must only wear thongs from this part on. Don’t have any? go to the store and buy some, can’t do that, use the internet, and just make sure that you have a pretty thong to wear ready for tomorrow.

Day 18.

Take an hour's morning break without your cage when you first wake up.

The first thing to do is go straight to the shower, wash yourself and your cage, and follow the feminization tasks that are about to ensue today:

  • Brush your teeth, say thank you mistress, and go downstairs.
  • Today you’re eating on the floor. No questions, all meals must be eaten with you sitting on the floor.
  • At the end and beginning of each meal, say thank you, mistress.
  • Once your morning food is done, you should be at the time to put your cage on.

It’s time for a naked day, every moment you spend in your house you have to be completely naked aside from your cage.

You can wear a towel around your waist if you have people coming around.

If you have to go to work, you can dress, but all clothes must be off when you enter your house/apartment/room.

After all of that, I think you earned a nice edging day.

No cumming go to edge me please and do these settings:

Duration: long (extra points for very long)

Difficulty: hard

Do you want to cum? No, I will cum later

Caged for whole day and night apart from for hygiene maintenance, edging, and a morning break.

Femdom challenge:  Shave everything, your ass, your cock, your gouch I want it hairless after today.

Day 19.

Don’t unlock yourself today, spend the whole day and night locked up again.

No cumming, no sexually touching your tiny dick, and no unlocking, unless it’s to clean or readjust (or prevent injury).

Femdom challenge:  Start wearing pink socks.

Day 20.

Get up at 5:30.

You made it to day 20! congratulations.

You deserve a reward.

Do this in the morning as the first thing you do:

  • Before and after pictures of your cock.
  • Measure and see how small your cock is getting.
  • You’re caged for the whole day and night part from the challenges below.
  • Go and pick a random number, it’s time to go to the chastity punishment list and see what you got.
  • Do the punishment, if it’s time-based do it for no more than 40 minutes unless it’s a chore. If it’s keyholder-based and I’m your keyholder go to the nearest solo punishment. If it involves you cumming, move on to the next challenge.
  • From this point on every day is a punishment to teach you obedience and that you do whatever your keyholder/dom says.

After you have done the above, today you need to edge for two hours and I am feeling generous so this can be broken into two one-hour intervals.

Go slow, remember if you cum it’s 6 days of nothing but cold showers.

Now, wait at least 3 hours after edging for this next part of today's challenge...

You have 15 seconds to cum, unlock yourself, have your cock in one hand, not hard, and in your other hand, a timer, and once it's on you have 15 seconds to cum. If you do cum, clean it up. If you don’t manage to do it? lock yourself back up, no orgasm for you today.

Femdom challenge: Add a hair clip to your hair every day from this point on.

Day 21.

Day 21.

Take a two-hour break from being caged, wash, and put yourself right back in the cage for the entire day and night.

Punishment: Apply nipple clamps to yourself for 30 minutes (use clothespegs if you don’t have some), while doing this stand in the corner and don’t speak a word.

Femdom challenge:  Time to try on stockings.

Punishment: Footrest for 20 minutes for your keyholder, if no one is there, just go in the footrest position for 20 minutes.

Day 22.

Awww a two-hour break cage break? I don’t think so. You can have a 30-minute break in the morning and a 30-minute break at night. No more and no less.

Vibrator fun! I want you to watch pegging porn for the next 20 minutes, while you place a vibrator on your cock cage. You can’t cum. If you cum then you have to go back 3 days today 19. This is to teach you self-control.

Grooming day is day 22: I want you to cut/file your nails, wash your hair, do a face mask, and maybe take some time to work out your future skincare routine, I like to keep my chastity slaves looking good for me. Clean your cage, give it a good deep clean, you’re going to need it as you’re going to be wearing it a lot over the coming days.

Punishment: Record yourself saying 'thank you mistress' for thirty minutes.

Femdom challenge: Paint your nails for me.

Day 23.

I forgot about you for this day.

Just keep your cage on till tomorrow.

Don’t say a word, I don’t want to know about you being caged.

This is a day for me to forget you, you should know you’re forgotten about. I don't even know where your key is!

Punishment: Stand in the corner, silently, in your cage, don’t say a word, no phone, do this for an hour, in this time think about why you think I gave you this forget day and what you could do better to please me or your keyholder.

Day 24.

Take off your cage? Nope, locked up again, day and night.

I hope you’re horny, no release today.

I just want you to feed into your horniness, but don’t cum or touch yourself. That’s not what this is about. This is about enjoying the frustration of wanting to cum.

Punishment: Self Spanking, I feel like you need to give yourself 20 firm spankings while in your cage.

Femdom Challenge: Pick your slave name, at this point you’re 24 days in, it’s time for you to have your own slave name, take a pick, I think it should be a feminine-sounding name. Let me know in the comments below or send me a message with the name you picked for yourself.

Day 25.

You made it to day 25, well-done slave.

Today is a very special day, you only have to wear your cage for 2 hours.

Enjoy this time, because you won’t be out of your cage much this next week.

Before and after pictures please where you measure your cock. I want you to comment on the results of your measurement with an update of how your feel about your caged cock.

Usually at this point the cock starts to be as submissive as you are and starts losing size.

How today is going to look: Take your measurements as soon as you wake up, brush your teeth, have a coffee/tea, remember to say 'thank you mistress', write down 10 reasons why you’re happy to be caged up, then do the femdom challenge below and you can now have a ruined orgasm following the rules below.

You can cum today, but you can only cum in your cage, it must be ruined and you can’t use your hands, I think this is fair, you need to learn to be more creative with your release.

Femdom challenge of the day: Cock worship! worship one of your cock-shaped dildos for 30 minutes, suck it, give it a handjob, kiss it, do this without stopping, talk, and say how big it is and how happy you are to suck it.

This isn’t because you want it, it’s because I said so.

I hope the punishment obedience training is going well and you’re remembering while you’re locked up you are a plaything for a keyholder and that you must obey every order.

Punishment: Say thank you miss Jess 500 times (or name of your keyholder), do this while wearing your cage, your thong, and with your butt plug firmly inside of your ass.

Day 26.

You are staying locked up.

Day and night.

Unfortunately for your slave, it's a chore day:

You need to do all your home chores.

  • Change the sheets
  • Wash the dishes
  • Mop the floors
  • Vacuum the rugs
  • Clean behind your couch
  • Wash your windows
  • Clean your toilet

You must wear a thong, your cage, and just a little t-shirt while doing the chores.

After you are done with your chores, get on your hands and knees and say thank you 26x out loud.

Then I want you to take a moment and think what you would do to my tight pussy or your keyholders pussy if you weren’t locked up, meditate on that thought for 10 minutes, and then remember that you’re caged and none of that can ever happen.

Watch 1 hour of cuckold porn, it’s good for you to start getting ready to share all your future partners.

No orgasm or ruined caged orgasm with no contact on your cock, you decide.

Femdom task of the day: Its feet worship day! find some feet porn and watch it for at least 10 minutes, complement the feet out loud for the whole experience.

Punishment: Eat something really spicy, I recommend a chili or some chili powder.

Day 27.

Spend your whole day and night in your cage. You can take a 2-minute break from your cage today, after that, it’s a full day and night locked up.

Wear your vibrating butt plug for at least 2 hours, extra points if it vibrates and you keep the vibrations on.

You must also try waxing your ass today, if you can’t wax then you must shave your whole body from the neck down.

Write 'chastity slave' somewhere on your body with a body-safe pen (here are some more ideas of things you can write on yourself).

I bet you’re feeling so unbearably horny.

Well, it’s time to get even hornier, I want you to head to these pages below and look at them for 1 and a half hours, you have to obviously be in your cage, but you can touch your caged cock, you just CANNOT cum.

After those 90 minutes, you're going to be fit to burst but don't worry, I may still give you the chance to cum yet...

The only catch is that it has to be a facial. I am being kind, as it’s also your femdom task.

Don’t want to give yourself a facial? then after those wonderful 90 minutes, you will get no release. Sorry, not sorry.

Punishment: Cold shower, make sure you say thank you before and after, the shower must last for no less than 30 seconds.

Femdom task of the day: Give yourself a facial, don’t know how? lookup self cum facial. If you can’t do a facial then worship a dildo cock with a 10-minute non-stop blowjob.

Day 28.

Spend the full day and night in your chastity cage.

It’s also time to level up your ass again.

You’re allowed to cum anally, but no cum can leave your cock, if it does go 3 days back.

You are only allowed to use an 8-inch and above dildo, if you own a 10 inch, then get it inside you right now.

Take your time taking every inch and remember, with every thrust you take, say 'thank you, mistress'. Extra points if you use the suction cup base and go hands-free.

You should be so horny you’ll take anything up your ass.

Watch one hour of sissy porn either as you use your dildo or straight after. I want you to become a sissy, a cuck, and a chastity slave, it’s just part of the motion, you’ll learn it.

Write down why you like sissy porn while you’re watching it, and write down the videos you enjoyed, this is important in finding your true self.

Punishment: Be on your hands and knees naked with your cage on for 30 minutes.

Femdom challenge: Try on or get your first summer dress.

Day 29.

You are only allowed to cum if you are doing so like this.

Can’t cum? then no orgasm for you 🤣

You’re not allowed out of your cage for the entire day or night.

Make sure you have a deep clean of your body ready for tomorrow, I want you to be shaved or waxed (extra points) and I want you to make sure you’re spotless and so is your cage.

It’s time to look back over the last 29 days, and write out a little diary of your experience, have you enjoyed being caged?

  • Write ten things you love and ten things you hated about your lock-up.
  • Write why you think you should remain locked up and why you think you should be let out.

This is important, sometimes you might have to explain why you deserve to get out of your cage to your keyholder, make it good, and don’t cut corners, you can post what you wrote down in the comments or send it privately to me.

Punishment: say 'thank you mistress', every time you go to the toilet, every time you eat, every time you clean/wash something, when you get changed, when you make your bed when you use your phone, every time. This is a light punishment, I just want you to learn how to speak at all times.

Femdom challenge: Sleep in lingerie, must be a bra and panties.

Day 30.

Release day is tomorrow.

Start by going on fap instructor with these settings:

Min time: 1 hr 36 minutes

Max time: 1 hr and 40 minutes, you must complete this time to move on to the next challenge.

You have to cum first by vibrations via a vibrating wand with your cage on, as it's a special day you can jerk off without your cage on for 3 minutes and then put your cage back on to cum with the vibrations.

You must clean up any mess and you must create make at least 5 loads of cum today.

Once you have come through vibrations it's time for another release, you can jerk off to any chastity porn you wish. Extra points if you use a fleshlight, cum, and then use it again with your cum still inside of it. This will show you what it’s like to fuck your keyholders' cum filled pussy (only the cum in her will be from someone else).

If you fail to cum 5 times today, then you must repeat the last 5 days of this challenge.

Anytime you’re not jerking off you must, be in your cage, it's a good incentive to make me that cum.

Punishment: I think the above is enough for you today.

Femdom Task: Wear a cute pair of bra and panties today.

Cool Off From The Challenge

illustration of my three step cool off from being locked up in chastity

I've been thinking and it's not a good idea to completely release you from this challenge just yet.

Enjoy one day off out of the cage but no orgasming.

I don’t think you should orgasm for the next 7 days and have at least 5 hours per day locked up.

After that, you’re only allowed to ruin your orgasms for the following 3 days.

Then you’re allowed to orgasm like normal but only while watching femdom, chastity, or cuck porn.

How Far Did You Make It?

Let me know what day you tapped out or if you completed my extreme chastity challenge! Thanks for playing.

Jess ❤

4 thoughts on “30 Day Chastity Training Program”

  1. When you say “clean up” after you cum, do you mean eat/consume?

  2. Wow. Great article. I read your entire blog and I am really very satisfied with your way of explaining. I hope it will help me to play my bdsm with my partner.

  3. 1. firstly, it was my fantansy to be in chastity cage.
    2. i like to be in control of my wife(gunjan)
    3. i like to femdomization while in cage
    4. i want to see my cock shrinking
    5. i want myself as a sissy while caged
    6. i am in love with my chastity cage
    7. chastity cage helps me in control my emotions
    8. chastity cage makes me a perfect slave for my wife(gunjan)
    9. chastity cage helps me in learning good behaviour for my wife(gunjan)
    10. i like wear thongs over the chastity cage
    11. i like to be dressed as maid in chastiy cage
    12. i love to have make up as girl in chastity cage
    13. i love to wear lingrie while in chastity cage
    14. i love to wear red colour stockings while in cage
    15. i would clean my wife(gunjan)’s body with my tongue while in chastity
    16. i want this chastity on my cock for the whole life and should out for once a month for sex with my wife(gunjan)
    17. i can be in chastity as long as keys are with my wife(gunjan)

  4. I would like to try this challenge using KT (Kinesiology Tape). The “Pro” Tape is available at CVS in pre-cut strips and lasts up to 4 – 7 days when applied well.

    This means I would be “Tucking” instead of wearing a chastity “device”. The websites state that if tucking and taping is done well, erection is entirely prevented.

    This ought to be more comfortable and long lasting – even after showering.

    Yes, it is less secure. But, following your instructions should remain easy enough while remaining chaste.

    As for security, this is about obeying YOU in the first place. If all goes well, who knows. Perhaps something more permanent can be arranged. *eg!*

    In any case, I am most curious what can be achieved by submitting to you. More specifically, how far down the rabbit hole can I go and where does it lead?

    In any case, does this sound plausible?

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