Progressive Chastity Game Week One The slave wears a chastity device for an initial lock-up of one week, with supervised cleanings and checks. After seven days pass, the slave can roll a six-sided die to try for release from chastity and enjoy some pleasure. Alternatively, they may skip rolling and wait another week for better die options listed under Week Two results.
The Keyholder can add penalty days if the slave performs poorly while in chastity. These penalties must be summed up and resolved before any rolls happen. At this stage, the slave has two choices: accept a punishment chosen by the Keyholder to clear away all penalty days, or roll the die using Week One options after serving those days. Penalty days build up over time; if not cleared either by waiting them out while rolling for Week One results or accepting a specific punishment, they carry forward.
If the total reaches 7 penalty days at any point during the game, a mandatory punishment applies, and an extra week is added to allow access to higher-level options.
In Week One, die rolls correspond to these outcomes:
- Roll a 1: The slave is restrained but released from chastity, allowed to cum via a method decided by the Keyholder. If they cum, it must be eaten; if not, the device goes back on, and they wait two weeks for another roll with Week Two options.
(Note: Rolls of 2 follow identical rules as above regarding restraint, release, cuming/eating, or failure leading to a two-week wait).
- Roll a 3: No removal of the chastity device. The slave waits two weeks for another roll.
- Roll a 4: Same result; no removal, waiting two weeks.
(Note: Rolls of 5 and 6 are identical in outcome to each other below).
If rolling a 5 or 6: No release from the device. The slave is restrained and receives a penalty spanking, then waits two weeks for another roll with Week Two options listed later.
Week Two When the slave reaches Level Two while still wearing the device (with regular checks), either by passing their first roll or waiting out penalties after a bad one in Week One, they get to try rolling again. As before, they can wait an extra week for better odds under Week Three rules.
Penalty days work similarly here too: accumulate them based on performance; resolve totals before rolling. At Level Two, the slave may accept a Keyholder-chosen punishment to wipe away penalties or roll using Week Two results after serving time in the device.
If 7 penalty days are reached at any point during this phase, another mandatory punishment occurs, adding an extra week toward eligibility for higher tiers.
In Week Two:
- Roll a 1: The slave wears ankle cuffs and a collar, with one hand free to jerk off within one minute. If they cum, it is eaten; if not, the second hand gets restrained, the device returns, and they wait three weeks for another roll using Week Three options.
(Note: Rolls of 2 follow identical rules as above regarding cuffs/collar, timing, cuming/eating, or failure leading to a three-week wait).
- Roll a 3: The slave is restrained but released from chastity, teased by whatever method the Keyholder chooses. If they cum, it’s eaten; if not, device back on, waiting three weeks for another roll with Week Three options.
(Note: Rolls of 4 follow identical rules as above regarding teasing, cuming/eating, or failure leading to a three-week wait).
- Roll a 5: No removal of the chastity device. Wait three weeks for another roll using Week Three options.
- Roll a 6: Identical result; no removal, waiting three weeks.
able to reach the next level In week 3, the numbers on the die match up with these options. If the Chastity slave rolls a 1, they are fitted with ankle cuffs and a collar, given one free hand, and allowed to jerk off as many times as possible within 5 minutes. The Chastity slave must eat all their cum before restarting the game at week one. If the Chastity slave rolls a 2, they are fitted with ankle cuffs and a collar, given one free hand, and allowed to jerk off as many times as possible within 5 minutes. The Chastity slave must eat all their cum before restarting the game at week one. If the Chastity slave rolls a 3, they are fitted with ankle cuffs and a collar, given one free hand, and have 1 minute to jerk off. If the Chastity slave cums, that cum must be eaten and the game restarts at week one. If the Chastity slave fails to cum within that minute, their other hand is restrained, the chastity device goes back on, and they wait 4 weeks for another roll with the Week 4 options listed below. If the Chastity slave rolls a 4, they are fitted with ankle cuffs and a collar, given one free hand, and have 1 minute to jerk off. If the Chastity slave cums, that cum must be eaten and the game restarts at week one. If the Chastity slave fails to cum within that minute, their other hand is restrained, the chastity device goes back on, and they wait 4 weeks for another roll with the Week 4 options listed below. If the Chastity slave rolls a 5, they are restrained but released from chastity, then teased by whatever method the Keyholder chooses. If the Chastity slave cums, that cum must be eaten and the game restarts at week one. If the Chastity slave fails to cum, the device goes back on and they wait 4 weeks for another roll with the Week 4 options listed below. If the Chastity slave rolls a 6, they are restrained but released from chastity, then teased by whatever method the Keyholder chooses. If the Chastity slave cums, that cum must be eaten and the game restarts at week one. If the Chastity slave fails to cum, the device goes back on and they wait 4 weeks for another roll with the Week 4 options listed below. **Week 4 ** When a Chastity slave reaches level 4 while still in chastity (undergoing regular inspections and cleanings) after either passing through week 3 or serving the penalty of waiting out those 4 bad rolls, they get to roll a 6-sided die for a chance at release from chastity and some pleasure. The Chastity slave must accept one of the options below that matches their roll. The Keyholder may add Penalty days during the game in chastity if performance is poor. If penalty days accumulate, they must be dealt with first before any rolls can happen. At week 4, a Chastity slave can choose to take a punishment decided by the Keyholder to wipe away those penalty days or roll using the Week 4 options after serving them while still in chastity. Penalty days are cumulative if not wiped away either by waiting out the days and rolling for Week 4 options or by accepting a specific Punishment option. If a Chastity slave reaches a total of 7 Penalty days at any point during the game, a punishment becomes mandatory and an extra week is added before they can roll again for those Week 4 options listed below. A special rule applies in week 4: if a Chastity slave has already accrued 7 unaddressed penalty days when eligible for week 4, then Options 1 and 2 become identical to Options 5 and 6, because that many penalties mean the Chastity slave hasn’t earned enough merit for those higher-level prizes offered in options 1 and 2 at this stage. In Week 4, the numbers on the die match up with these options: If the Chastity slave rolls a 1, they are released from chastity and get to choose between intercourse or a blow job from the Keyholder. All cum must be eaten by the Chastity slave before restarting at week one. If the Chastity slave rolls a 2, they are released from chastity and get to choose between intercourse or a blow job from the Keyholder. All cum must be eaten by the Chastity slave before restarting at week one. If the Chastity slave rolls a 3, they are placed in ankle cuffs and collar with one free hand, allowed to jerk off as many times as possible within 5 minutes. All cum must be eaten by the Chastity slave before restarting at week one. If the Chastity slave rolls a 4, they are placed in ankle cuffs and collar with one free hand, allowed to jerk off as many times as possible within 5 minutes. All cum must be eaten by the Chastity slave before restarting at week one. If the Chastity slave rolls a 5, they are placed in ankle cuffs and collar with one free hand, given 1 minute to jerk off. If the Chastity slave cums, that cum is eaten and the game restarts at week one. If they fail to cum within the minute, their other hand is restrained, the chastity device goes back on, and the game starts over from Week 1. If the Chastity slave rolls a 6, they are placed in ankle cuffs and collar with one free hand, given 1 minute to jerk off. If the Chastity slave cums, that cum is eaten and the game restarts at week one. If they fail to cum within the minute, their other hand is restrained, the chastity device goes back on, and the game starts over from Week 1 Special Notes for the game. As you can see this game teaches a Chastity slave how staying in chastity while pleasing their Keyholder offers both reward and challenge. If a Chastity slave performs well, they get good options presented to them. If they perform poorly, there are consequences. Since it is partly chance-based, the Keyholder also uses penalties to steer the game toward correcting bad behavior or rewarding good actions. The ultimate prizes in Week 4 can only be achieved through obedience and pleasing the Keyholder. Also, since punishments aren’t strictly defined here, their scope relies on the Keyholders’ imagination and can suitably punish infractions depending on what fits best. Furthermore, if the Keyholder is hesitant to give up that final prize in week 4, she might use penalties to block those options too. As an added twist, the Keyholder may decide to restrain a Chastity slave and blindfold or hood them right before rolling for fate’s decision. From this viewpoint, the Keyholder can rig results however she sees fit based on how well the Chastity slave has been performing.