I was tasked by my keyholder to find ideas, games, tasks, etc for two chastity subs to play against each other. One is with the keyholder, one is distant. She wants things that will determine their fate for how long they will be in chastity. let me know if you have any ideas!
perhaps something like the writeforme.org site. Subs could compare task writing results in a competition.
Both slaves have to make a commitment to stay chaste for an undefined period. He who is the last to beg for relief has the chance to earn a full orgasm at the keyholders discretion while the one who folds first will only get a ruined one/a punishment/nothing but a prolonged lock-up. No contact between the slaves or knowledge of the competitors decision.
Could be started over again for each slave separately, setting the counter to zero. So the one with the most stamina might earn one orgasm after the other leaving his opponent the pain and frustration. You could also establish points for every day in chastity which might be traded for a milking to soothe the itching need to come or to gain information about the competitors behaviour and so on...
Have them each roll five dice (on video) and count them up to determine the number of days that the other sub will be locked up!
You could have them play the prisoners dilemma. They can choose to help or forsake the other sub with a different outcome for each of them depending on if they both try to help eachother, both try to forsake eachother, or each choose an opposing option. You would need four possible outcomes on a sliding scale depending on what they chose. You want to tempt them into turning on eachother for the best reward but also hold out the possibility of a slightly less good reward if they both cooperate. The worst outcome is for whoever tries to help the other when that person forsakes them. It’s pretty devious as most people want to help another person but the possibility of a greater incentive for turning on them (and not knowing what the other is thinking/doing) will make people reconsider.
This depends on whether the remote one has access to an emergency key or your keyholder can unlock then remotely. Via a video link your keyholder gets both of you to unlock and then masturbate together: with her using a metronome to decide the rate. Whoever comes first loses . . . and you both go straight back in, on camera, until the next time.
They both have to watch and play a cock hero stroking game, like the one attached, in front of you or in front of you and your guest. The first one to cum loses and gets locked in chastity and has to suck the other Cuck's cock and swallow his load in front of you and your guest. He will stay locked in chastity and wearing sissy panties until he sucks the other cuck X number of times in front of you and any new guests over the next 2 weeks. If the winner fails to cum when being sucked off the roles are reversed. https://xhamster.desi/videos/bisexual-cock-hero-xhH3LFr
if they were both together I would play this game with them they are both locked, the first one who calls to be released must give the other player a blowjob while handcuffed and ring gagged