To earn his freedom, I’m going to have Bill do something extreme.
He got himself locked up because he’d complained about being bored. So, if he wants to be free, he needs to prove to me that he’s not bored anymore. I think he should also show me exactly how creative and grateful he really is. I’ve put a lot of time and effort into alleviating his boredom, after all. I need to know that he appreciates me.
I’m going to have Bill prove that he’s worthy of being unlocked.
First, he’s going to have to show me some skill and creative thinking. I’ll have him perform for me, with my lover. I want to see Bill make my lover cum. He can use anything he can think of to get my lover off. His hands, his mouth… his tight little hole. The key here is that there needs to be cum, and Bill needs to cause it.
Next, I’ll have Bill write me an essay about masturbation. I want to know what he’s learned about masturbation during his period of denied chastity. What did he learn about the nature of desire, about the privilege of stroking his cock, about the joy and ecstasy of orgasm? I want to know. In detail. Again, grammar, spelling and the sheer poetry of words together count.
Finally, to earn his freedom, I think I’ll have Bill jerk off for me. While still locked. Oh, yes, you can cum while in chastity. I don’t think I’ll tell Bill how to do it, but for you I’ll share a hint: creative imagery, prostate massage and a lot of built up sexual frustration. Delicious!
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