Ideas
Chastity Games: 16 Keyholder Games With Real Rules
Sixteen chastity games with real rules: dice, cards, a wheel, coin flips, streaks, task ladders, long distance versions, and how to keep the keyholder happy.

Chastity games are how a keyholder dynamic survives past week two, when the novelty of the lock has worn off and the wearer has started asking "when" in a voice that makes the keyholder want to drop the key in a drawer. A game answers "when" with a rule you both agreed to before anyone was horny or sulking. The die decides and the keyholder gets to watch. Sixteen chastity games with rules follow, luck first, then effort, then long distance versions and how to keep the keyholder from resenting the job. The same games run with an AI keyholder, which is how many people on KinkSim play a first term.
Ground rules before any chastity game
A game controls permission. It has no say in whether the cage comes off, because that is a medical question and dice don't get a vote. Write these into the chastity contract before the first roll:
- The wearer keeps a spare key, sealed in an envelope so using it is visible rather than impossible.
- Full removal to wash and inspect every two to three days, whatever the score says. Beginners come out daily and have no business in multi-day games during week one.
- Numbness or tingling that doesn't clear within ten to fifteen minutes of adjusting, any color change behind the ring, swelling that keeps growing, broken skin, trouble peeing. The cage comes off, no permission asked and no penalty applied, because a wearer who believes a stop costs a week hides the symptom.
- Every game that adds time has a ceiling. Rolls past the ceiling are wasted, never banked.
If the cage is new, read how to put on a chastity cage first, since no game fixes a wrong ring.
Chastity games of pure chance
These let the keyholder shrug and say "not my decision," a lovely sentence to have available.
The Sunday die
Roll one six-sided die on Sunday night. The number is the days locked that week, and the rest of the week belongs to the wearer. Swap in a d8 or a d10 from a board-game box once a six stops scaring anyone.
Double or halve
The keyholder announces, before touching the dice, whether they'll roll twice. The first roll sets the days. If they roll again, an even number doubles the first roll and an odd number divides it by the number shown, rounding down. Then the wearer rolls once, times ten, for the minutes of unlocked time at the end of the term. The announcement is the cruelty.
The duel
Both roll. If the keyholder's die is higher, the gap between the dice goes onto the wearer's term in days; if the wearer's is higher, it comes off; a tie changes nothing. Chaster's dice extension (checked September 2026) is this exact game against a bot, with the gap multiplied by a time value the keyholder sets.
The daily coin
Flip one coin a day. Tails means nothing today, try again tomorrow. Heads means a ruined orgasm today, or the wearer can bank it, and two heads in a row upgrade the bank to a full one. Ask the wearer on day four whether they'd still gamble on a second heads.
Nine black, one white
Put ten marbles in a bag, nine black and one white, and draw one a week. Black means locked and that marble leaves the bag, so the odds improve every draw. White means release. A keyholder in a mood adds a blue marble that puts every black one back. Worst case is ten weeks, hence the ceiling clause.
Card lock
Shuffle a deck and draw one card a day. Red number cards add that many hours, black number cards remove them. A jack freezes the timer for a day, a queen means a task of the keyholder's choosing, a king means the keyholder picks the outcome, and an ace ends the term. ChastiSafe runs card locks online, free, if you'd rather not trust a wearer alone with a deck.
The wheel
Cut eight segments on cardboard with a paperclip pointer, or use any wheel-spinner site. One wearer's published Locktober 2025 Chaster wheel read: freeze, add two hours, thirty minutes in the pillory, plus or minus forty-five minutes, a custom task, add one hour, plus or minus one hour, fifteen minutes in the pillory. Hours keep a wheel spinnable every day. An "add one month" segment gets spun once and then the wheel lives in a cupboard.
The random event
Release happens the next time something outside anyone's control happens. The first snow, or the next away win for the local team. The wearer now has a relationship with the weather forecast.
Chastity games the wearer can influence
Effort games suit a keyholder who enjoys obedience and a wearer who wants to earn it.
The streak
Put a paper calendar on the fridge. Every clean day, no touching, no whining, check-in sent, gets a tick. Miss one and the streak resets to zero. At a number agreed in advance, and seven is a good start, the wearer earns whatever is on the reward list. A calendar the keyholder ticks in pen beats any app.
The task ladder
Draw a ladder with ten rungs. Each completed task from the list, and the submissive tasks guide has plenty, climbs one rung; a failed or half-done task drops two. The top rung is an unlocked night, the bottom rung adds a week. The ladder turns a vague "be good" into a decision the keyholder made once instead of forty times.
Chore roulette
Roll a d6 against a list of six chores, with six as the keyholder's special request. The best keyholder advice I've read says the job is to control when and how the wearer comes, and nothing more. Chores the wearer already does and wants to gamify are fine. Trading release for the dishes turns the dynamic into a chore chart with a padlock, and the game is over the first time the keyholder reaches for the key because the bathroom needs cleaning.
The tease timer
Unlock, set a timer for thirty minutes, and the keyholder edges the wearer with hands or a toy while the clock runs. At the buzzer the keyholder picks one of three outcomes: full, ruined, or back in the cage. Say nothing until the buzzer. For a keyholder who's elsewhere, the AI edging format runs the same countdown over a call with the wearer's own hands and a stop command.
The key hunt
Hide the key and give the wearer thirty minutes to find it. Whatever they find they can use before the timer ends. The keyholder can keep the key on their person the whole time and watch the search, which is either cheating or the entire game depending on who you ask.
Chastity poker
Play any card game you both know. The wearer bets days added, foot rubs and errands; the keyholder bets days off, a ruined orgasm, or permission. Stakes go on scraps of paper in the pot, so what's at risk is visible before anyone folds.
The contest
The keyholder names the game, Mario Kart or a plank, and the stakes. Win and the keyholder decides how long the freedom lasts. Lose and time goes on. Letting the keyholder choose means they pick the game they're good at.
The orgasm ratio
The keyholder rolls two dice. The total is how many orgasms they receive before the wearer's release is even discussed. An eleven is a busy fortnight for the wearer and a very good one for the keyholder. Every list of keyholder games needs one the keyholder wins, and this is where I'd start.
Long distance chastity games
The wearer keeps the physical key sealed and the game runs on trust and photos. The daily coin and the wheel work over a video call, with the wearer flipping or spinning on camera. For anything longer than a week, use an app.
Chaster (free tier of one lock with three extensions, checked September 2026) has the wheel, the duel dice, tasks and penalties as extensions, plus a verification-picture extension for a daily photo and a hygiene opening that defaults to fifteen minutes every two days. ChastiSafe is free and runs card locks plus a community pillory where other users vote on punishments, which I wouldn't hand to a new couple. Neither can see your skin.
How to keep chastity games fun and not resentful
When a chastity arrangement stalls, it's usually the keyholder who's done with it, and the games above make that worse if they turn the keyholder into an unpaid croupier. What keeps them in the game:
- Give them something to win. The orgasm ratio, poker stakes they want, a task ladder where the rungs are things done for them.
- Put the game on a day. The Sunday die buys six days of not being asked. A wearer who asks on Wednesday has broken the game, and that goes on the streak.
- The wearer does the admin. They build the wheel, print the calendar, set up the Chaster lock and hand over the dice.
- Keep numbers small and rotate. Hours, not months. Swap the game every month or two, because the same wheel for a year is a spreadsheet.
- One out-of-role talk a week, ten minutes, where either person can say a game has stopped being fun. When the keyholder says it, the game ends without an argument.
Denied people get strange around day ten. Aftercare applies to chastity as much as to a flogging scene, so a keyholder who has just spun "add two days" should expect to spend the evening being kind about it. If orgasm denial is the draw for one of you and a chore for the other, no game fixes that.
Chastity games with an AI keyholder
Paste your rules and your chosen game into the first session with a chastity AI keyholder on KinkSim and it holds them across sessions, streak count included, along with which segment the wheel hit last Tuesday. That's the bookkeeping half of keyholding, the half human keyholders tire of first. It can't hold a key, see a photo of your skin, or help in an emergency, so the spare key and the medical rules stay with the wearer. Characters on the orgasm denial tag are built for this, and the chastity and denial roleplay guide covers setting terms before the first roll.
Pick one game, not five. The Sunday die and a ten-minute talk is a complete dynamic. Add a wheel when the die stops scaring anyone.
Questions, answered
- What are chastity games?
- Games that settle something inside a chastity dynamic by luck or by effort. How many days the cage stays on, whether tonight's release is full, ruined or refused, which task the wearer owes, or who gets attended to first. Dice, cards, a spinning wheel and a coin are the usual props, and apps like Chaster run digital versions for couples who live apart. The game replaces nagging with a rule both people agreed to before anyone was sulking.
- How does a chastity dice game work?
- The simplest version is one six-sided die rolled on Sunday night, and the number is the days locked that week. The duel version has both people roll. If the keyholder rolls higher, the gap between the dice goes onto the wearer's time; if the wearer rolls higher, it comes off; a tie changes nothing. Chaster's dice extension is that duel played against a bot, with the gap multiplied by a time value the keyholder sets.
- What is a good chastity game for a long distance relationship?
- A coin flip on a video call, a wheel the wearer spins on camera, or a Chaster lock where the keyholder configures the wheel, dice and tasks and the wearer sends a daily verification photo. Keep the physical key with the wearer in a sealed envelope, since a keyholder in another city cannot help at 3 a.m. The game governs permission, never whether the cage can come off in an emergency.
- How do I keep chastity games fun instead of resentful?
- Give the keyholder something to win in every game, put the game on a fixed day so the wearer stops asking, let the wearer do all the admin, and never trade release for household chores. Rotate games every month or two because the same wheel gets stale. Hold a short out-of-role talk once a week where either person can say a game has stopped being fun, and drop it without an argument when they do.
- How long should a chastity game keep someone locked?
- Cap it before the first roll. A first term of a couple of weeks is plenty, and wear inside it should build from hours to overnight rather than starting at twenty-four hours. Every game that adds time needs a written ceiling, because a wheel with an 'add one month' segment is fantasy material that wrecks a real dynamic. No roll overrides the hygiene removal every two to three days or a medical stop.
- Can you play chastity games without a cage?
- Yes, and plenty of couples should start that way. The rules work the same on an honor-system lockup. The die still decides the days, the coin still decides the ruined orgasm, and the streak still resets when the wearer touches. A month of honor chastity before spending money on a device tells you whether the dynamic is fun, and a keyholder who cannot see the cage is trusting the report either way.
- Are there keyholder games where the keyholder wins something?
- The orgasm ratio game is the classic. The keyholder rolls two dice and the total is how many orgasms they receive before the wearer's release is even discussed. Chastity poker lets the keyholder bet days off and permissions against the wearer's foot rubs and extra days. A game the keyholder can lose without losing anything is a game they stop wanting to play, so build one of these into every rotation.
- Can an AI keyholder run chastity games?
- It can run the bookkeeping side. It holds the streak count, rolls for you, and remembers what the wheel landed on last Tuesday and the penalty still owed. A chastity AI on KinkSim keeps that across sessions. It cannot see your skin, cannot hold a physical key and cannot help in an emergency, so the wearer keeps every key, and the hygiene and medical rules stay yours to enforce.