The pain of the small cage and a plug that was 2 sizes bigger than you were used to was almost too much, but the pure pleasure you were feeling from the rush of arousal was enough to keep you going forward with your training.
It never occurred to you that the reason your anal plug kept changing patterns was because your girlfriend was live streaming you all gagged and locked, and the audience was controlling it.
Finding a friend who was also into chastity was amazing, her ability to be super cruel and leave you locked for days or weeks on end without anything except being teased the entire time, however, was slightly less awesome. You were almost regretting tell