[BR1985]

Ok, here’s a couple of longer ones for you both.

Chastity challenge 1:
Lock each other in chastity so your friend has the keys. The game ends when one of you begs the other to be unlocked. Whoever asks to be unlocked first is the loser. They will hand over the keys to the winner who can unlock and the loser must get them off however the winner wants. The loser will be stripped naked and unlocked where ever the winner wants - the more humiliating the better.

Chastity 2 sock challenge:
Start with a pair of socks each. Every day, swap socks. Don’t wear any others. The loser is the first one to give in and wear clean socks. They then get locked in chastity for as long as the winner is willing to wear only those two pairs of socks. The winner can demand the loser worship the socks whenever they want, and gets to decide how the loser gets to cum when unlocked. I suggest the loser is gagged with the dirty socks and given a foot job.