Cherry's Diary
Copyright© 2025 by Mike McGifford
Chapter 5
Dear Diary, I got in trouble with Charles this evening. We were talking about my day and I happened to mention that I was still trying to catch up on the events of the auction with you.
At first Charles thought I was complaining and he stiffened under me. I ran my comment back through my head and immediately realized my mistake.
I had been sitting sideways on his lap in the living room and he was stroking my thigh where the fabric of my dress separated, baring my stockings, while we talked. He’d finished telling me about how the copier he uses at work had gone haywire and had started spitting out blank sheets like missiles. I giggled, imagining it raining copy paper.
Then he’d asked me if I’d gotten all the way through my task list and that’s when I’d honestly explained that laundry, dusting, exercises, grocery shopping, lunch, afternoon exercises, working on my herb garden, preparing dinner and putting together his evening cocktail didn’t leave a lot of time for me to finish catching up with you.
I quickly apologized and assured him I wasn’t back to complaining like the spoiled bitch I’d become when Randall had left for college nor was I going to have a repeat of one of my episodes.
You know, dear Diary, I’m talking about an episode such as the one where I went crazy and in a fit of frustration and self loathing among other things, had burned my last diary and all the gifts Charles had given me since he had first accepted the challenge of training me.
I assured Charles that it was simply the fact that I hadn’t spoken to you for such a long stretch - you know what I mean, dear Diary.
Usually I catch up with you three times a day when there’s not a lot going on and then suddenly, a major event happened that required so much telling yet I missed catching you up twice in a row.
I begged Charles’ forgiveness for making him tense up and suggested that maybe spanking me would relax him again.
Charles stood up, picking me up with him before setting me on my high heels. I thought he was going to order me over the arm of the sofa in my normal spanking position and I almost proactively moved to comply with his wishes but instead he ordered me to my knees.
Instead of a spanking I received a lecture as I looked up at him. Charles reminded me that my lifestyle was the result of a request I had made. That I had begged him to assume full control of everything that was Cherie and that is why I am now known as Cherry the cunt, not Cherie the pretentious bitch.
He admitted that he still sometimes felt guilty about the episode he knew I was referring to where I’d gone off the rails so spectacularly and he still wondered occasionally if it could have been avoided by him acting differently.
I started to assure him once again that he’d done nothing wrong but his lifted finger immediately shut me up. He told me he wasn’t looking for reassurances. He said that was what he was there to provide me with and that he wasn’t prone to self doubt.
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