You always thought you had problems with being insensitive down there, however, it would appear you just jerked off too much and lost sensitivity, 2 months in chastity fixed that.
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.
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.
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.
For two months now you have been locked and forced to ride a dildo any time your partner brought home a partner. As of last week though, you know have to write fanfiction about the events as they are happening.