Roses are red,
Violets are blue,
This Valentine’s Day I’ve got 14 chastity challenges for you.
Violets are blue,
This Valentine’s Day I’ve got 14 chastity challenges for you.
Because as if I’d let this little holiday that symbolizes adoration, dedication, and lust go unmarked. These are 3 of my favorite things. (Along with total submission, locked cocks, and a pair of boots that have been licked clean by a good chastity slave.)
I'd like to thank all of my adoring slaves who took part in our Valentine's Challenge. Each day, I emailed them something deviously cruel to test their limits, and their devotion. For those of you who missed out (tut tut), I've collected each challenge here for you so you can try them in your own time.
Can you make it to the end?
How to Play My Valentine’s Chastity Challenge
Complete one challenge per day, starting today and climaxing in two short weeks.
Should you successfully achieve Every. Single. Challenge, then you get a special reward at the end. But no skipping ahead!
Play them solo or with the assistance of a Keyholder. Just make sure you have fun doing them, okay sweetie
Let’s begin.
Day One
Look At Your True Love
An easy(ish) one to start. Take a photo of your key. Set it as the lock screen image for your phone or computer and leave it that way until Valentine’s Day. It’ll be an ongoing reminder of your predicament.
Keyholder variant: Have your Keyholder hold or wear your key if they don’t already. Perhaps you could request that they do something suggestive with it. Take a photo. Set it as directed.
Day Two
Tweak a Traditional Valentine’s Gift
Lingerie is such a sought-after Valentine’s gift. And I don’t want you to miss out this year. So your challenge is to treat yourself to some new underwear but (because there always has to be a but) you must choose a style you’ve never worn before.
For example, if you’re usually a boxers kinda guy, then it’s time you purchased some tight, sexy briefs to really show off that package (and cage). Or if you’ve only ever worn men’s underwear then it’s time for your delicates drawer to have a more feminine touch.
Go buy this underwear today and wear it immediately.
Day Three
Love the Buzz
Today I’ll be testing your stamina and self-control using a vibrating sex toy of your choice. (Or the vibrate setting on your phone if you don’t have one.)
Lock yourself in your cage (if you’re not already.) Hold the vibrator against the cage for 30 seconds. Press stop and pause for 15 seconds. Turn the vibe back on and put it back on your caged cock for another 30 seconds. Then pause for 10 seconds. Now go for another 30 seconds of stimulation. Rest for 5 seconds. Can you make it through the final 30 seconds? If you want to pass this challenge, you’d better hope so.
Day Four
Write a Romantic Chastity Poem
Write a poem declaring your love for male chastity and cock cages. It can be 1 or 2 verses long, a sonnet, or hell even a limerick if you must. I don’t care. What I want to hear in your poem is your dedication and adoration for the lifestyle.
Once you’ve written and spell-checked it (I won’t tolerate any sloppy spelling errors) please post it in the comments of one of our last 3 Instagram posts or DM it to me if you’re feeling shy.
Day Five
Find the Queen of Hearts
Get a standard deck of playing cards. Pull out all 4 of the Queens and one Joker. (Or use the ace of hearts if there’s no Joker.)
Shuffle the 5 cards. Lay them face down.
Now, you only have one shot at this. Pick a card. Which did you get?
Queen of Hearts – Well done, you won. You can spend the rest of the day out of your cage. (If that’s what you really want?)
Any other Queen – Uh-oh, nothing for you this time. Stay in your cage.
The Joker – You just got another 3 days added to your current lock up time. (Or 3 hours if that’s how you use your cage.) Boo-hoo for you.
Keyholder variant: They choose what reward the Queen of Hearts represents, as well as the Joker forfeit.
Day Six
Wear Your Heart on Your Sleeve
Make a public acknowledgement of your chastity life, in your vanilla life. If you’re not looking to out yourself, then this sign can be as subtle as you want or need it to be.
For example, you might:
- Use a spare cock ring as a keyring for the day.
- Wear your key on a chain or necklace.
- Accessorize with a mini padlock added to your belt buckle or your shoe/shoelaces.
Day Seven
Lust at Long Distance
We’re at the halfway mark. Celebrating this milestone makes me want to set a task that’ll frustrate you. So here it is.
Ask your Keyholder if they’ll strip you to just your cock cage, restrain your hands behind your back, and let you watch them climax.
Solo chastity variant: Watch 3 to 5 minutes of your favorite porn while remaining caged and without unlocking or touching any of your erogenous zones.
Day Eight
Melt My Heart
For this challenge you’ll need an ice cube tray (any size), your key, and a timer.
Freeze your key in the ice cube tray. Once it’s frozen, remove the block with your key in it and place it either:
- In a bowl next to a heater.
- In a pan on the hob on a low heat.
Start the timer running. You’ve got until the block melts and the key is released to give yourself a hands-free orgasm. Stop the timer when you cum.
Did the ice cube melt before you finished? Oh dear. Sweetie, I’ve got news for you. The time it took you to climax is how many days or hours you have to add to your current locked period.
For example:
- 4 minutes = 4 days or 4 hours.
- 10 minutes = 10 days or 10 hours.
- 15 minutes and 32 seconds = 15 hours and…? Well, who cares? Don’t be so damn pedantic. Just round it up or down to the nearest minute.
Day Nine
Display Some Public Affection
Let’s test your subservience and manners.
Your challenge today is to be out-of-your-way polite and helpful to anyone you come into contact with. Be it an extra smile and a thank you to the barista that makes your coffee, holding every single door open for people to go in front of you, or picking up some extra chores around the house to help a partner or neighbour. It’s on you to do it. There’s a good chastity slave.
Day Ten
Play Mr and Mrs Chastity
This game is designed to test how well you know your Keyholder. Get them to write their answers to the following.
- What is your preferred title during sessions and playtime?
- Finish this sentence, ‘When I’m locked, you like it when I…’
- What do you love most about chastity?
- Your favorite punishment for me is…
- And finally, you prefer the cock locked or unlocked?
Now, it’s your turn to answer the questions. Write your responses or say them out loud.
If your answer matches your Keyholder’s, you get a point. You need to get at least 3 correct to avoid a punishment of their choosing. (Which will probably be whatever the answer to number 4 is.)
Solo chastity variant: Answer the following questions for me, Mistress Tracy. You should be able to dig up the answers on our Instagram or throughout the Lock the Cock blog if you dig hard enough.
- What’s my hair color?
- I preside over dungeons and play spaces, where?
- Small cage or flat cage?
- Short-term chastity or long-term chastity?
- Where do I like to keep my slave’s keys?
Click here to see the answers.
1 - Red, 2 - New York, 3 - Flat cage, 4 - Long term, 5 - On a chain around my neck.
If you got 3 or more right, you avoid punishment. Good puppy.
If you mean to tell me you got less than that then bad dog. Your punishment for your lack of attention is to eat your goddamn dinner off the floor tonight.
Day Eleven
Cherish Your Cum Covered Cage
This Valentine’s we’re going to show your cage some affection. After all, it works hard to keep your cock subdued.
Now, you have a choice. You can either cum in your cage or remove it and cum over it. Whichever you find easiest. But if you take your cage off, you must replace it as soon as you’re done. Because the final part of your challenge is to stay in your cum soaked cage until it’s time for your routine clean.
Day Twelve
Love From Another
This simulated cuckolding challenge requires the help of your Keyholder. Ask them to enjoy some time with their favorite dildo while recounting the best fuck they had with an ex or another partner. While they’re doing that, you’re to sit helplessly in the corner of the room or edge of the bed, not touching your cage or cock.
Solo chastity variant: Practice the ghost penis technique. I realize you won’t achieve this in the space of a day, so I’m giving you until the end of the month to work on it.
Day Thirteen
Edge into Valentine’s eve
We’re only a day away from finishing the chastity challenge and games. So here’s something especially fun for you and your Keyholder.
Indulge in an edging session. Locked or unlocked. It’s your choice but strictly no cumming.
Solo chastity variant: You’re not going to escape this challenge. Unlock and use edgemeplease.com to tease and torture yourself. Relock as soon as you’re done.
Day Fourteen
I Love You for Your Mind
Let’s round this challenge out with a playful mindfuck to make you think on your feet.
You’ll need a timer or stopwatch. Set it for 15 seconds.
Below is a topic. Name at least 10 things related to that topic in 15 seconds.
Ready?
Click here to see the topic.
Name 10 fetishes or kinks.
Success? Take 1 hour or 1 day off your lock time.
Failed? Then you must hand write ‘My caged cock wants to cum’ 100 times. When you’re done, take a photo and post it on X, explaining why you had to write these lines. Don’t forget to tag us in your post.
Let’s Give This Valentine’s Challenge a Happy Ending
This was a lot of fun. If you managed to complete every challenge—or at least had a good go at it—then good boy. You can take Valentine’s evening off from your chastity pledge. Unlock your cage, enjoy a glass of your favorite poison, and treat yourself to some chocolates.
But remember, tomorrow is just a regular day. So you better be back in that cage as soon as you wake up.
Want More Chastity Challenges Like This?
Then go right ahead and choose another chastity game and challenge.
