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.
Its been 3 weeks since you got locked, you are not allowed any stimulation of your little clitty at all. This is what you have to resort to for orgasms now.
Hypnotism never worked for you, but listening to it and fantasizing while doing it was hot, that is until you listened to the chastity swimsuit stories. Next thing you remember is being locked in a chastity cage and having new bikinis, you didn't rememb
The hard plastic cage covering your privates didn't let any sense of feeling through, but for some reason you tried to still tug on it even if you knew it was a hopeless endeavor.
She said she had never cum from oral before. You thought you could prove her wrong so she bet you that you couldn't do it, and would be locked in chastity until you made it happen. Perhaps you were too confidant in your abilities. You thought you would