Cherry's Diary - Cover

Cherry's Diary

Copyright© 2025 by Mike McGifford

Chapter 6

Dear Diary, Charles has left for work and he allowed me to clean up our breakfast dishes and give the kitchen a quick once over before sitting down with you. Other than that I’m to focus on updating you and nothing else. I don’t even have a butt plug in this morning to ensure my attention is not divided.

Before I left you, I had described the auctioneer. She was dressed like a dominatrix rather than an auctioneer and the crowd seemed to love it. She just plain intimidated me, I admit, Diary!

I was standing alone in a pool of light, dressed in a ball gown and sky high heels. My hands were clearly cuffed before me. I wore a rhinestone choker that had a D-ring around the back, mostly hidden by my hair because even with an updo, there were intentional loose locks of blonde hair at my neck. A casual observer would have considered it simple jewelry but the auctioneer knew better.

She strode confidently up to me and I didnt even notice the announcer leaving. The auctioneer’s boots clacking on the wooden platform caught and held my attention even above the noise of the crowd. It was the loudest thing in my sterling silver hoop adorned ears.

I had acted confidently myself before the auctioneer’s appearance, standing tall and looking straight ahead while the announcer had detailed my sexual experience as if that was all there was to me.

When the auctioneer got close I automatically lowered my eyes, my confidence departing. To be honest, Diary, she just seemed too intimidating to even consider trying to stare down. She put off a masculine vibe despite her very feminine looks, shape and attire.

While not beautiful in a movie star way, she was attractive and much younger than me at maybe twenty five years of age. Yet she scared me. How is that, Diary? I’m confident, well trained and fifty years old and the appearance of a girl half my age caused my sphincter to pucker.

I could say it was the quirt, but I know it wasn’t. Well not only the quirt. It was everything about the situation Charles had put me in. I was to be stripped, fondled, publicly aroused and auctioned for charity.

I was the first one being auctioned and the purpose was to show what a “real” slave auction was like for the viewing pleasure of the audience before the more demure auctioning of the volunteer guests. It was all I could do to constrain the trembling in my knees.

The auctioneer had her back to the audience and brought her face close to mine. With her lips near my ear she reminded me to be a good girl and follow instructions fully and immediately if I knew what was good for me.

For some reason that was more intimidating than anything so far. It was insulting as I strive to be totally obedient to Charles and condescending too, as I was clearly the young woman’s elder.

I still have feelings and being insulted and spoken down to by a complete stranger grated on me while at the same time causing me to tense up further.

The auctioneer kept her face inches from me as if expecting an answer so I eventually said yes. What else was there to say, Diary? Well I quickly discovered what. Without moving her head, the quirt struck my left calf then she instructed me to call her Mistress Aurora. The quirt didn’t really hurt, but I almost peed myself right there.

I jerked, bit my lip instead of crying out in surprise then after a moment, repeated myself with the inclusion of her title while feeling myself blush. I should have known she would want to be called mistress while wearing the outfit she had on.

Aurora moved her face away from mine then half turned, put her arm around my shoulder to address the audience with her microphone, standing next to me as if we were a couple of friends. This stranger was well within my personal space.

“Grandma here thinks she’s a suitable candidate to be sold to the highest bidder tonight. We really need to see what is being offered, am I right?” She asked the audience to a huge round of applause and some more catcalling.

“Such a lovely dress, my pretty,” she said to me, but used the microphone to address the crowd. She was really talking to them.

“In the waistband of my skirt I have a pair of shears on one side and a handcuff key on the other. You get to choose whether this lovely dress is cut from your body or carefully removed. You’ll answer with a simple left or right. Do you understand?” She asked me, still really talking to the audience.

I think it was at that moment I realized the audience would have seen the shears she had hidden behind her back when she was facing away from them.

The audience seemed to love this game and shouts of, “Left!” and “Right!” broke out with accompanying jeers and cheers from the young audience.

I didn’t know what to choose. In hindsight I know I probably could have analyzed the audience’s suggestions but in the moment, I blurted out, “Left, Mistress Aurora,” knowing she had just told me not to hesitate.

“Left it is!” Aurora laughed and reached behind her back then paused to build suspense.

When her hand came back, she proudly held up a tiny key, to jeers from the audience.

For all I know, the shears were really what was tucked into her waistband on the left and she’d played the game simply to scare me more. It definitely worked, Diary! I was completely off balance and simply felt relieved that she wouldn’t be ruining a gown that had cost Charles over three hundred dollars.

Aurora knew how to work handcuffs and had me free of them in moments, leaving me wondering what to do with my hands. Aurora didn’t leave me wondering for long, telling me to undo the button at the top of my gown then leave my fingers interlocked behind my neck.

She then moved around behind me and drew the zipper all the way down to my butt, commenting for the benefit of the audience that she was not seeing a bra strap.

As you know, Diary, I had thought long and hard about what to wear. I could have worn a strapless bra under the off-the-shoulder gown but I’d known I would be getting stripped and I’d decided that since the gown didn’t really require a bra, being so strongly reinforced, that I’d skip it. It was simply one less item of clothing to risk having cut away.

With the zipper down, I felt the support for my heavy funbags disappear. I had not been bared to the audience’s view simply because Aurora had kept a hand on the top of the gown from the back.

I was still very embarrassed although I could feel my nipples reacting to the situation as if they had a mind of their own, swelling and hardening under the loosened fabric. Once Aurora let go, the gown would slip to my waist. There was nothing else holding it in place.

“Do you want to see some granny tits?” Aurora loudly asked the audience, to which mostly male voices hooted and hollered their agreement. I also heard a few “Eww” noises but they sounded like they were being yelled in fun.

Aurora removed her hand and gravity did its job. The top of the gown fell away from my funbags and settled at my waist, baring half of me to the audience. My large, full yet saggy, pierced grandma boobs were on display for the world to see.

I felt mortified yet excited by the surprised reaction of the audience. If my fingers hadn’t been interlaced behind my neck I know I would have covered them.

Despite my training I almost did. I heard shouts of, “she’s pierced!” and, “what a whore!” and “I didn’t know old people did that!”. I even heard one female voice shout, “put them away!” but a quick reply of, “fuck you, Mallory, you’re just jealous!” made others laugh.

Aurora slipped her hands around me from behind and, still with quirt and microphone in hand, and bounced my funbags from below, much to the audience’s delight. The microphone transferred the sounds of her hands on my jigglers to the audience.

I was a little surprised she didn’t play with my nips but she did assure the audience they looked like they’d be fun. She then asked the audience if they were bothered to see the rest of me and she was immediately assaulted with cries of “take it off! Take it off!” The chant changed to cheers when Aurora agreed.

The gown had been designed to cinch at the waist with a bow at the back. That’s why it hadn’t simply slipped to the floor in the first place. Aurora quickly released the bow, but still had to tug the gown over my hips.

I don’t think I’ve ever mentioned, Diary, that I have large hips. Charles has often complimented me on them, assuring me they make great handles to control me while he rides one of my nether holes from behind.

Anyway, the gown finally pooled at my feet, leaving me in just my thong.

I was so very embarrassed, dear Diary! I wanted to tell myself that at least my cunt was covered but realistically I knew without doing an inspection that it wasn’t.

A ribbon of material bisecting my labia isn’t a covering. My shaved mons and my clit piercing was probably covered by the tiny triangle of white satin material, but that’s all. Aurora made fun of the color of my panties for the amusement of the audience, telling them that I must think myself pure to be wearing white before verbally chiding me for my choice.

She told me that a whore like me shouldn’t have bothered wearing panties or I should at least have worn crotchless lace ones so they wouldn’t get in the way of someone fucking me. I don’t own crotchless panties, Diary. Charles has never expressed an interest in them.

Aurora was either truly angry at seeing them or she faked anger because she tore them off me, not even pulling them down. The audience loved it.

I was left nude before an audience of mostly young people I couldn’t see but could hear, including Charles, sitting in the dark with his date, watching me trying to remain calm and appear unconcerned that I was being displayed for these people to critique my body.

I know I’m fit, dear Diary. I know I look good. I exercise at least an hour every day, but I also know I have my faults. My funbags are different sizes. The left one is slightly bigger than the right and my nipples don’t face forward but instead, the left points more left and the right points more right. In fact, each milk sack does, giving me a wider than desirable cleavage when I’m naked. I have a too-wide gap between my legs and my inner labia peeks out quite a bit past my outer labia.

Charles acknowledges that my cunt has drooped with age and doesn’t look as pretty as the young women whose cunts he prefers to explore. He says he knows mine as if it was his own.

Well, really, Diary, it is without a doubt, his, isn’t it? I’ve reminded him of that many times over the years even before it became literally true.

I certainly can’t fault him for seeking new sources of entertainment as is his right, nor can I complain that he’s finally decided to share me.

Charles sharing my body with others is one such right I chose to give up when I gifted my whole being to him. I reminded myself as I stood there naked under a spotlight with crowd noise roaring in my ears and Aurora pointing out features of my trim yet mature body that the evening was all about Charles finally showcasing his property and allowing one lucky person to control me for a night.

I took comfort in the fact that this is what Charles wanted for me. I stood straighter. I pushed out my chest and clenched my cheeks. I tried to bask in the glow of being the center of attention despite my humiliation.

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