7 Fun Sissy Chastity Games

7 Fun Sissy Chastity Games

sissy chastity games

There’s not too many things that a sissy can do to enhance her sissiness other than to refrain from having those nasty, male-type orgasms. Locking yourself up—or being locked up—in a chastity device is one sure way to enhance the whole sissification process.

Things get even more interesting if a sissy can add an accountability partner to the equation. That person would would come in the form of a chastity keyholder.

The situation becomes much more intriguing when that same keyholder turns out to be the sissy’s main partner—a Dominate person preferably.

A creative keyholder can make a sissy’s chastised existence even more stimulating by incorporating some chastity games into the scenario.

Life is more fun when you turn it into a game. This is especially true when it comes to sissy chastity.

Let’s take a look a 7 of these fun sissy chastity games that can be played.

#1 – Sissy Chastity Roulette or Spin the Wheel

chastity spin the wheel

Chastity Roulette, or spin the wheel, is a drop-dead simple chastity game to play and will allow your creative sissy juices to begin flowing.

The idea is to construct a wheel out of cardboard—or even wood if you want to go first-class. You will then need some sort of spinner made from again, cardboard or wood. You then attach the spinner to the wheel with a pin or small nail.

Now the fun part begins. You get to divide the wheel into pie-shaped areas with a pen or marker—then write in those triangular spaces what will happen, depending on where the spinner lands on the wheel.

As in the above image, feel free to make each segment on the wheel as wide or narrow as necessary.

For instance: the Full on Fuck area should be so damn narrow that there would be little (if any) chance of the spinner ever landing there. This has a way of making the game more fun and exciting for everyone involved.

You and/or your keyholder can choose appropriate consequences that are only limited by your collective kinky imaginations.

Here are a few ideas:

  • Game Over Immediately – 1 More Week of Chastity
  • Full on Fuck
  • Game Over Immediately – 1 More Month of Chastity
  • 45 Minute Tease and Denial Session With Ruined Orgasm
  • Game Over Immediately – 1 More Year of Chastity
  • Prostate Milking with Chastity Cage Left On
  • Permanent Chastity and Agree to Become a Cuckold
  • Masturbate on Keyholder’s Ass – Sissy Licks Up Her Mess
  • 1 Hour of Uninterrupted Oral Servitude – Chastity Device Left On
  • Keyholder’s Choice

As a prerequisite for playing, the chastised sissy might need to earn the right to spin each week. This, of course, is determined solely by the keyholder and what behavioral standards She or He has set for the sissy.

For example, the sissy must earn a certain number of points, based on appropriate conduct during the week in order to be deemed worthy enough to spin the wheel.

Having this requirement in place ensures that the sissy will always be on her best behavior. Alternately—and much more devious—the sissy would be allowed to spin only at her keyholder’s whim.

#2 –Sissy Chastity Dice

chastity dice

To play sissy chastity dice you will need a pair of dice—one white one and one black one (actually any two colors will do) and a sissy chastity device of your choice. An awesome place to get one is over at OXY.

The white die represents the number of days spent in chastity. The black die determines the number of weeks of being locked away.

Oxy Shop Chastity

Let’s say the sissy rolls the dice and up comes a 4 on the white die and a 3 on the black one. She would remain caged for a total of 25 days (3 weeks and 4 days).

With this version of sissy chastity dice, the shortest possible time of chastity would be 8 days and result by rolling snake eyes (1 week and 1 day).

The longest stretch of being in lock-down mode would be 48 days. That would happen if the sissy was unlucky enough to roll boxcars, or two sixes. The math is easy: 6 weeks and 6 days.

To make things even more challenging, they do make 20 sided dice. In case you were wondering; rolling two 20’s would mean a sentence of 160 days in chastity.

Certainly there are many other variants of sissy chastity dice. This particular version I found over on reddit.

#3 – Sissy Chastity Ice

chastity ice game

No doubt you’ve already heard of the sissy chastity ice game. This is where the keyholder freezes the key to the sissy’s chastity cage inside a block or cube of ice; the dimensions of which can be of the keyholder’s choosing.

When the Domme or Dom deems that the sissy should be allowed a short time out of her cage, she is given the block of ice and must melt it using a body part only, retrieve the key, unlock and remove her chastity device and then masturbate to climax in a predetermined and humiliating fashion.

The catch—and there’s always a catch to being a sissy—is that this must all be done within a certain time frame… like say five minutes.

If the keyholder has a cruel streak, then the sissy might be required to melt the ice cube by placing it on her nut sack.

This, of course, would make it even more challenging for her to become hard and orgasm within the allotted amount of time. If, and when, sissy fails to climax, the keyholder will be left with a fully frustrated and much-more-eager-to-please sissy.


#4 – Sissy Chastity Dildo Harness

chastity dildo harness

Many chastised sissies harbor delusional fantasies of fucking girls. That should NEVER happen in real life of course. The best that any sissy should hope for is a temporary and very-short-lived time out of her cage.

But there’s nothing wrong with playing some mind-fucking head games with a sissy. She wants to fuck… so let her!

bubbles bodywear

She will be allowed to while remaining locked in chastity and wearing a dildo harness attached to a dildo of her keyholder’s choosing.

Many women often complain that their husbands, boyfriends or lovers don’t have the stamina required to bring them to the multiple orgasms that they so deservedly desire. That’s never the case for a trans-lesbian sissy that is, more-or-less, permanently locked away in a chastity device.

A sissy can fuck her Mistress for hours on end while wearing a dildo harness. She will obviously stay perpetually hard throughout the sexual encounter. If she happens to otherwise physically tire before her Domme is satisfied, then the demanding keyholder will simply go to the whip so to speak.

Much like a jockey encouraging their mount to the finish line with a few (okay, sometimes more than a few) well-placed strokes of the riding crop, a mischievous Mistress can do precisely the same—her finish line being an earth-shattering orgasm.

Sounds like a superbly fun game for the keyholder and a fabulously frustrating one for the sissy. Perhaps she should have considered the consequences more carefully before introducing her wife or girlfriend to sissy chastity.

#5 – Sissy Chastity Hide the Key

sissy chastity hide the key

The sissy chastity hide the key game seems oh-so simple on the surface. The keyholder hides the key somewhere in the house and the sissy must find it within the allotted amount of time in order to free herself and experience that deliciously denied climax.

The catch—remember, there’s always a catch when it involves a sissy—is that the keyholder can hide more than one key. There is only one real key however. The others are fake keys. The real key is hidden in a much more obscure place than the fake ones.

There is a very good possibility that the sissy will fail to find the real key fast enough to free herself as she will be spending a precious amount of time fiddling around with the more easily found fake keys.

Since the keyholder makes-up the rules of the game, there is nothing that says that the game must be played fairly. For instance, the real key doesn’t necessarily need to be one of the keys that is hidden.

Setting the sissy up beforehand to fail at this game has several benefits… at least for the keyholder. Everyone knows that a sexually frustrated and denied sissy makes for a more docile and easy-to-manipulate girl.

Let the sissy chastity games continue.

#6 – KH to Sissy Orgasm Ratio Game

100:1 orgasm ratio

It’s common knowledge that sissies should be allowed to cum rarely (if at all). It also goes without saying that keyholders can orgasm as often as they desire. Obviously, that makes for a fairly wide discrepancy between the two unequal parties involved.

To play the KH to sissy orgasm ratio game a ratio must be established between the amount of orgasms that a keyholder has to the number of climaxes allowed the sissy. For example, if the keyholder desires one orgasm per day, and a ratio of 100:1 is established—then the sissy would be unlocked from her chastity device and allowed to cum once every 100 days.

That works out to about 3.7 climaxes per year for her; which is an easily doable number for a well-trained sissy.

But maybe the sissy’s keyholder only desires three orgasms per week. That’s 156 climaxes per year. Maintaining a 100:1 KH/sissy ratio would mean that the poor sissy would be unlocked only once every 2.3 per annum.


Although that may appear to be an extremely low number, it is still very achievable—and highly recommended—for a properly-conditioned sissy.

Obviously, the KH to sissy ratio can be set to any proportion, depending on the sissy’s state of development and the whimsical wishes of her Dominate. But a 100:1 ratio is a good benchmark to aspire to.

There are several benefits to playing this KH to sissy orgasm ratio game.

The sissy will be conditioned to live predominately chaste existence. This will serve to transform her into the best sissy she can possibly be.

She will be more motivated to always look her sexiest and to hone her oral skills to perfection. This will make her more desirable to her keyholder which will ultimately result in more sex for the KH and possibly… more orgasms for the sissy.

Finally, being sexually denied for extended periods of time will help the sissy achieve that elusive sissygasm that she most desperately desires.

#7 – Sissy Chastity Beat the Clock

chastity beat the clock

I haven’t had the opportunity to play this sissy chastity beat the clock game before but it’s one of my all-time favorite sissy chastity fantasies. The game begins with a sissy in chastity—preferably for an extended period of time. Her hands are then handcuffed behind her.

Her keyholder removes her chastity cage and then sets a timer for 1 minute. The sissy is then instructed to cum in any way that she can, within the 1 minute window of time. There are two stipulation: that if she does manage to achieve orgasm within 1 minute, she must lick up her mess. The other is that she is not allowed to dry hump another person’s leg—like a dog would.

What typically transpires is that the sissy, desperate for relief, winds up on her belly humping the floor (remember, her hands are handcuffed behind her back).

Depending on how long she’s been kept in chastity, it’s usually a 50/50 chance that she is able to get herself off within one minute. Whatever the outcome, she is immediately locked back up in her cage; with the help of an ice pack if she wasn’t successful and her clitty/cock is still hard.

This game works very well at a party. Everyone is dressed up except for the sissy, who is wearing only make up, wig, bra, heels; and the handcuffs of course.

It’s quite an amusing—but at the same time highly erotic—sight for the guests to watch a handcuffed sissy desperately humping the floor as they stand around cheering her on. Most of them are hoping for her to succeed as they want to witness her humiliating act of licking up her sissy mess, while they contemptuously applaud.

A Sexy, Chastised Sissy

To me, there’s not too many things more erotic (or sexier) than a chastised sissy. Sexually denying a sissy pushes her down to exactly where she needs to be; on her knees. She’s simply a docile plaything, waiting to submit, serve and obey.

Adding sissy chastity games to the above situation creates a sexually stimulated scenario on steroids, one that’s hard to beat.

But before you can play any these sissy chastity games, you gotta have a chastity device. There are a few things you should be aware of before you buy one however. I’ve answered some questions you might have over on my Sissy Chastity Devices page