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Archive for the ‘Video’ Category

Chastity Dice Game Now Online

Friday, April 4th, 2014

The chastity dice are now rolling at The Playground! Want Mistress Cassandra’s devilish bones to determine how long you should lockup? Want to roll with her for a chance to unlock? How about letting her wicked dice determine if you should cum? All of these games are now available and ready to torment you!

Customize? 1134 personalized dice games saved to date.

As an additional feature, you can create your own custom game with all the kink you (or your chastity partner) can handle! Simply click the custom game button, fill out the form and finish by saving to Mistress Cassandra’s server. You will be presented with a link you can forward on to your play partner. Each roll can have 3 possible outcomes:

Game Over: Your command is displayed and no more rolls are allowed

No Delay: Your command is display but the player can roll again immediately

Delay:  Your command is displayed but the player must wait for the specified time before rolling again (the minimum and maximum delays are in seconds)

Maybe if you’re good, Mistress will blow on your dice and wish you… luck!


Browser support: HTML5 Only. {IE 9+, Safari, Firefox, Chrome, Opera, iOS (iPad)}


Chastity Dice Are Coming!

Sunday, March 2nd, 2014

To those of you who voted in our recent features poll, Thank You! One of the top requests was additional random chance orgasm control games. You spoke, we listened. Here is a preview of our latest game: “Chastity Dice”.

We won’t give away all the details since we don’t want to ruin the surprise. However, expect some twists and turns as you roll and let Mistress Cassandra’s wicked control determine your fate!

Chastity Keyholder Mistress Cassandra Taunts You

Saturday, February 8th, 2014

It’s difficult to imagine…
… the power a woman has over a man when she holds… “The Key.”
The key to a release he so desperately wants.
The key to his fulfillment.
The key to his passion.
The key to the bliss that he craves with such intensity…
… he would do anything she asks.
With this key I can teach you to be so much more than you are now.
Imagine me, holding your key.
Sensuously teaching you.
Erotically training you.
Sexually molding you into a weak… obedient…  docile… PET!
A pet that serves woman in the manner they deserve.
Kneeling at their feet.
Hoping to see… praying to touch…
… ever anxious to serve the woman that holds the key.


Imagine your lock flesh, straining for release.
You beg me to relent.
You plead to me for mercy.
I smile knowing that now you are ready to learn.
Ready to learn the lessons of how to serve and service a woman.
Ready to ingrain the behaviors a woman deems appropriate for you.
Ready to offer a woman your unrequited desire… just for her amusement!

Watch full HD Video here.

Watch on YouTube here.

Question to our chastity game participants

Saturday, January 25th, 2014

Hello Valued Followers

Mistress Cassandra’s geek here. We (Mistress Cassandra & I) have a number of new features under development here at The Playground. In fact, we have so many ideas that we don’t know which to pursue next. So to best serve the community, we request you complete the following poll. By doing so you will not only help insure your desires are fulfilled, but also serve the community at large. Here is a brief description of the options we have in the works:

Interactive Chastity Adventure Games

In these games you, the owner of the cock, must search your way through the levels to achieve satisfaction. Standing in your way are various “obstacles” to prevent you from achieving your goal. A proof of concept of this game can be found here.


Additional random chance orgasm control games

More games like the chastity slot machines in which your fate is determined by chance.

Additional videos featuring Mistress Cassandra

Need we say more?

Submissive positions training

A number of submissive positions are presented along with their names and hand signals for assuming those positions. You will be required to learn these positions and pass a test to that effect.

Submissive positions detention with image verification

A submissive position is assigned for a specific time period. The slave under detention is required not to move from this position for the duration.

Random assignments with image / audio verification

Random assignments could potentially include domestic service activities, audio recitations, tease and denial instructions and seductive attire requirements. Verification of completing assignments insured by storing images / audios on this server accessible only to those whom you share the certificate.

Chastity lock verification

Using the latest technologies available, implement a chastity cage lock verification system. This could take the form of image recognition or possibly active lock sensing.

Thank you in advance for your participation,
Ms. Cassandra’s geek

What features would you like to see added next?

View Results

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Chastity Cage Video

Saturday, November 9th, 2013

For the amusement of all you boys out there, I’ve just added this chastity cage video. It highlights many different cocklocks both real and fantasy. Expect these images to be used in upcoming torments just to tease and tantalize you.

Best Wishes,
- Mistress Cassandra

Mistress Cassandra Answers the Question – “May I Cum?”

Thursday, October 10th, 2013

As I reported in my recent post, a new page has been added which assists me in answering your often asked question – “May I Cum?” You will get a different answer every day. How often will I say yes? That’s between me and the geek.

Ms Cassandra