12 Days of Chastity

Have you been a good boy this year?

Do you think you deserve a nice big orgasm for Christmas?

Well, of course, you don't. And you and I both know that. Because you're a slutty little chastity slave whose cock belongs to Mistress. You deserve nothing more than to stay locked up in your cage for the rest of your life.

But...it's Christmas, after all. So in the spirit of the holidays, I guess I can be kind. I'll give you one chance to have Mistress Santa put a chance to cum under your tree. But you don't get it for free - oh no, you've got to earn it. And the only way that you can earn it is by completing our extra special 12 Days of Christmas Chastity Challenge. (Yep, that's 12 whole days of tasks, so you'd better get started right away!)

So sing along with me, all you bad boys, as we count down to your only chance to earn your orgasm this Christmas.... by following along with Mistress's very favorite carol!

One Hour Tied Up Like a Tree

On the first day of Christmas, spend 1 hour tied up in bondage. Of course, the position, location, and materials used will be all up to Mistress - not you. She will make things as uncomfortable as possible, knowing that if you safeword out you'll have already lost your orgasm chance on the very first day of this challenge.

For an extra festive note, Mistresses, why not try tying your slave to the Christmas tree, or using festive "ropes" such as tinsel or Christmas lights?

Mistress's Santa List: The cock cage which pairs best with this torture is the Pleasurable Pain?, which adds a urethral plug to make your position even more uncomfortable

Two Blue Balls

On the second day of Christmas, it's time to give those neglected balls a little attention. Subject yourself to two sessions of ball torture at your Mistress's hands in order to pass this challenge. Of course, your cage stays on the entire time - no stimulation yet for your pathetic cock!

She might be kind and simply roll and stimulate them using her hands. Or she might be cruel and step on them with her favorite pair of pointy high-heeled shoes. You'd better watch out - and you'd better not cry if you want to move on to Day Three

Mistress's Santa List: Keep your testicles snugly trapped by a ring with a Good Things (Don't) Cum in Small Packages, which provides your Mistress with 24/7 access to those blue balls of yours.

Three French Maids

On the third day of Christmas, dress up in your sexiest maid outfit for your Mistress's pleasure. Don't forget the apron, frilly stockings and of course a nice pair of high heeled shoes! A red, green and gold trimmed outfit could help add a little festive flair for the holiday season.

Of course, simply dressing up as a maid would be far too simple to make up an entire day of this challenge. While you've got your sexy little outfit on, perform three household chores for your Mistress. Wash the dishes, do the laundry, prepare dinner or do anything else your Mistress desires!

Mistress's Santa List: A Sissy in Pink cock cage will pair perfectly with your sexy outfit and remind you constantly throughout the day just how much of a sissy slut you truly are.

Four Cums For Her

On the fourth day of Christmas, it's time to give your Mistress the attention which she truly deserves. You must give her no fewer than four orgasms throughout the day. Of course, your cock has to stay locked up the entire time - your hands, tongue and toy collection should be more than sufficient to make her cum.

Everything's up to Mistress - she gets to decide whether she wants all four orgasms all at once or if they are spread out throughout the day. While you are pleasuring her, you should receive no stimulation at all. It's all about her today!

Mistress's Santa List: Wear an Eyes On Her Prize stainless steel cock cage so that your Mistress can enjoy looking at your cock - but not touching!

Five Cock Rings

On the fifth day of Christmas, you must go through a challenge of pure will power. Have your Mistress remove your cock cage - or, if you truly feel like you can do it without accidentally touching or stroking, you can do it yourself. Then, replace it with a cock ring.

Spend 5 hours (total, not all in one session!) wearing the cock ring instead of your cage. You will need to use all of your mental strength to not have an orgasm in this time. To add a festive touch, tie a Christmas bow around your cock as well.

Mistress's Santa List: The Silicone Sissy comes with a full set of cock rings which can help you complete this day's challenge

Six Sexy Selfies

On the sixth day of Christmas, treat your Mistress to some sexy holiday selfies. After all, she deserves a Christmas treat, even if you don’t!

You must send her six pictures of your locked up cock throughout the day. At least one of them must be in a public or semi-public area such as the bathroom at a restaurant.

Put on a Santa hat, a pair of reindeer antlers or some elf gear to add a seasonal flavor to your selfies. You can even hang a candy cane off of your chastity cage! Make sure to make her Christmas Day as sexy and seasonal as possible to keep working towards your orgasm.

Mistress's Santa List: Choose an aesthetically pleasing cage such as the Caught In Her Web to catch your Mistress's eye.

Seven Cocks A-Dripping

On the seventh day of Christmas, it's time to kick things up a notch! From now on, the challenges will push you to the edge and force you to hold back your orgasm with all your strength.

Today, tease your cock until exactly seven drops of precum are released from the tip. Count out every drop while your Mistress watches and teases you about how pathetic your dripping shaft is!

Mistress's Santa List: Your Mistress can keep a Watchful Eye on you to make sure that you complete this challenge properly and don't cheat.

Eight Prostate Milkings

On the eighth day of Christmas, step into the role of the "maids-a-milking" from the more traditional version of the carol. You must stimulate your prostate via your asshole no fewer than eight times throughout the day. Whether or not you can "milk" your prostate by letting a little semen dribble out is up to your Mistress.

To make things more exciting, try stimulating your prostate using a variety of methods. Your fingers, your partner's fingers, and toys ranging from dildos to butt plugs can all do the job.

Mistress's Santa List: The Sad Pink Excuse covers your cock completely and forces you to focus on your ass and prostate instead.

Nine Teasing Edges

On the ninth day of Christmas, let's live life on the edge. Using the stimulation method of your Mistress's choice - NOT yours! - bring yourself to the edge of orgasm 9 times. Your Mistress also gets to decide how much time you get to rest between each edging session.

By the time you go to bed at the end of the day, you should be absolutely trembling and dripping from held-back orgasms. But don't rest just yet - you've still got three days of the Chastity Challenge to go!

Mistress's Santa List:Putting on an Undelivered Package will allow you to touch your cock through the cage's holes, but will still keep your orgasm nice and blocked.

Ten Sluts A-Serving

On the tenth day of Christmas, turn off the Hallmark movies in favor of something a bit more fun. Have your Mistress select ten porn videos which you must watch in their entirety before the end of the day. For an extra challenge, she may allow you to do so with a plug in your ass or a pair of clamps on your nipples.

Mistresses, mix up the videos so your slave will never be quite sure what's coming next. Include your favorites, his favorites, and those brand new ones you've always wanted to watch together. Feel free to masturbate while watching - unlike him, you can cum as many times as you desire!

Mistress's Santa List:You'll have an extra-"hard" time keeping your hands off your cock, so make it off limits with a Mistress's Little Prisoner.

Eleven Butts A-Throbbing

On the eleventh day of Christmas, you will have to battle both pleasure and pain. Your Mistress will deliver eight solid spanks to your ass, leaving it red, throbbing and covered with gorgeous marks and bruises.

Mistresses can decide whether to use their hands, paddles, crops or whips to deliver the strikes. Of course, you can always mix it up with a little bit of everything!

Mistress's Santa List: A bright red cage to match with your bright red ass. How about a Train Your Man in Devilish Red color?

Twelve Hidden Puzzles

On the twelfth day of Christmas, you've still got one last challenge to complete before earning your orgasm. Solve twelve clues or puzzles in order to earn your key so that you can be unlocked by your Mistress. Only once you have properly unlocked your cage will you finally be allowed to cum.

Your Mistress, of course, gets to decide the nature of the puzzles. Perhaps you will have to solve riddles or complete a jigsaw puzzle. Alternatively, you will have to search through the house for clues to locate your key. They can even be sexual challenges such as servicing your Mistress's pussy or letting her step on you.

If you successfully complete all twelve challenges, it's time for your Christmas wish to be fulfilled: you get to cum! A big, fully unlocked, non-ruined orgasm by your Mistress. But if you fail even one of them, it's right back into your cage until your Mistress decides to get into the holiday spirit once again.

Mistress's Santa List: If you successfully complete all twelve challenges, it's time for your Christmas wish to be fulfilled: you get to cum! A big, fully unlocked, non-ruined orgasm by your Mistress. But if you fail even one of them, it's right back into your cage until your Mistress decides to get into the holiday spirit once again.

A Little Extra....

This is our toughest Chastity Challenge yet - but here are some ways to make it even tougher!

Prove your ultimate devotion to your Mistress with these "tweaks" to our Twelve Days:

  • In addition to each new challenge, complete all previous challenges every single day. Yes, that's right - on the very last day, you'll be completing all twelve challenges in a row to earn your orgasm.
  • Spend your third day with your cock unlocked while you complete your chores - but you are still forbidden from touching it at all!
  • On the eighth day, spend the time in between prostate stimulation sessions with your ass stretched out by a nice big butt plug.
  • Replace the eleventh day's spanking with an even harsher form of punishment. Choose between whipping, caning, or having your penis shocked via our electricity-delivering Shock the Cock cage.

And, of course, share your results - whether success or failure - with your friends here at Lock the Cock. We always love to hear how people are attempting and struggling with our devilishly difficult Chastity Challenges. Who knows, your story might even get shared in a future Chastity Challenge story.


Merry Christmas to all - and to all chastity slaves completing this challenge, good luck!

Happy Holidays from your chastity-loving friends at Lock the Cock!