You never thought you would find a girlfriend, so when the first girl took an interest in you came along you agreed to do anything for her. Now you are seeing what she really meant by anything.
Chastity was never really your thing, but neither was latex, however, now you find yourself at the mercy of a sadistic but sexy woman who only wants to torture you and keep you on the edge of horny insanity.
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.
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
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.