Cherry's Diary - Cover

Cherry's Diary

Copyright© 2025 by Mike McGifford

Chapter 2

Dear Diary, as promised, Charles has allowed me time to update you and I was right! His smile when he laid eyes on me was worth the torture I’ve been through today.

Part of me is so relieved, yet I’m still on pins and needles at the same time - just not the sort that Charles might use to pierce my flesh. I’m going to be stripped naked before an audience of men and women attending a charity auction!

I’ve never in all my years been naked before anyone other than Charles. Even Charles’ friend, my gynecologist, has only seen parts of me naked - never the whole package.

I wonder, Diary, if the doctor will be there tonight? He’s wanted to put his cock where only his fist has ever been before and if he were to buy me, he could fuck me to his heart’s content instead of pretending it’s his cock he’s pounding into me during an exam.

I have frequently wondered if his cock is as big as his hands. There is an old saying about the size of a man’s cock having a direct comparison to the size of his hands and it was all I could do to not scream the first time he dilated me with his fist.

I learned long ago to relax and accept his hand up to his wrist inside me, but seriously, Diary, how would it feel if it was an actual cock? I’ve only ever had Charles in any of my holes. Will I enjoy it or have to pretend it’s Charles’ cock, as I do in my monthly gynecological examinations?

I’m getting sidetracked, Diary, and I know why. I’m scared about tonight even though I have no need to be. It hasn’t helped that Charles refused to fuck me when he got home. I don’t know why it surprised me that he arrived with his arm around a girl who could not have been more than eighteen, yet it did.

I secretly hoped he would afford me his undivided attention tonight but of course it makes sense that he has a piece of fluff on his arm and not be sitting alone while his own wife is auctioned.

Still, it hurt a little that even after seeing that I’d done all my chores, my full regime of exercises, including a full two miles on the treadmill in my heels, had his tux laid out, had put fresh pads down in my cage and prepared his evening drink, he took his whore into the bedroom for a quickie.

He didn’t even order me to watch from the corner like usual. He closed and locked the door after telling me to kneel next to my bowl in the kitchen.

I thought I’d disappointed him somehow, Diary! You know he only ever forbids me from watching him have sex when he’s angry with me but I was so relieved when less than twenty minutes later the girl and he came into the kitchen laughing together and he explained his actions.

He looked down on me and told me I should be as fresh as possible for my buyer and that if it was him who won me at auction tonight and he discovered semen leaking from one of my lower holes before he fucked me, he’d feel like he was getting sloppy seconds and not the premium pussy that had been advertised.

He hadn’t allowed me in his bedroom as the young girl didn’t want an audience. My first thought was that the stupid little bitch has a lot of growing up to do, Diary. Although, to be fair, at her age, I was still a virgin and the thought of fucking in front of my partner’s wife would have been inconceivable to me as well.

I also understand Charles’ point, Diary, but I really needed to feel his cock and I had been looking forward to it ever since this afternoon’s enema.

A good fucking calms me so very much and the denial was as hard to cope with tonight as when he’d first introduced me to that form of play. I don’t think I’m ever going to truly love not being certain Charles has had good sex, even if it isn’t with me and to be denied his cock on top of that while I’m feeling so needy, is so hard for me.

Charles gave me a straw to use with a protein drink in my bowl for dinner, explaining that he didn’t want to feed me solids after I’d gone to the trouble of having an enema. He said it would be poor form if I ended up being fucked in the ass after the auction and got poop on my buyers’s cock.

Charles and the girl, who I was not introduced to, would be eating at the banquet before the auction.

After my protein shake, Charles did a final inspection of my hair, makeup and attire, pleased my lipstick was not smudged from the straw and generally gushing about how great I looked, which of course made me blush from his praise.

I’m as ready as I’ll ever be, dear Diary. Charles has said he will be cuffing my hands in front of me and draping a shawl over them to hide the cuffs from casual observation.

I do not know if that is a requirement of the auction or merely a subtle reminder to me that Charles owns my body, but I choose to think it’s Charles’ way of wordlessly showing his love for me. I think the handcuffs may help calm me. Here’s hoping, anyway.

For now and always yours, Diary, Cherry.

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