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Derek –
I enjoyed listening to this. I have listened to it about a half dozen times. I envy Barclay. He is getting exactly what he wanted. Permanent Chastity and his only hope for release an anal orgasm.
The only think I would have done differently was pushed each day he is kept in chastity he love grows deeper and each time he is denied his love grows even more and whenever he is in his goddesses presence his clit would throb inside its prison.
I hope you make on for her to have her love grow for his sacrifice and devotion and to give her the desire to take him further and at the same time discipline him to show him she loves him whenever he does not meet her standards.