Sherry's Test Ch. 17a

Author's Note:

This story is completely fictional and the characters bear no resemblance to any persons living or dead. It is a pure fantasy and highly improbable in real life.

Please read this story in sequence if possible.

Comments, feedback and votes greatly appreciated. Appreciate the few comments I have received in the past and I apologize for the delay in continuing this series.

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Matt and Sherry were driving over to another of the Principal's Friday punishment sessions at his home.

"Wonder what he has in store for you today," said Matt, unable to hide his excitement.

"God, despite all the sessions we have had, the bastard has a way to keep surprising me and finding new ways to humiliate me," sighed Sherry with trepidation and like Matt, unable to keep excitement out of her voice.

"But nobody knows you enjoy these sessions so much," said Sherry putting her arm over her sweetheart.

"Yeah and same goes for you, despite your protestations to the contrary" said Matt knowingly and Sherry blushed.

Soon they were at the Principal's house and walked in without bothering to ring the bell.

Mary greeted them with a warm hug and said excitedly, "They are waiting for you in the basement!"

Mary led them down the stairs to the basement and Roberts greeted them with an exaggerated bow, "Ahhh Sherry at last. Welcome to my humble dungeon."

Sherry looked around to see an assortment of whips and paddles neatly hanging from the walls. There was a wooden frame in the center with leather cuffs at the top as well as bottom. And of course, there were no shortage of mirrors. And to top it all, there was a sophisticated projector system with a screen.

She looked around the room to see who her audience was and was not surprised to see Harvey and Nancy.

The only other person in the room was Omar, the appliance salesman and ex-student she had gotten fired.

"Oh no! Why him?" wondered poor Sherry helplessly.

"We decided to have a small audience today. Your punishment will be meted out by Harvey and Omar, two men you despise strongly," said Roberts.

"Of course Omar saw you stripped and spanked on Alumni day, but there is anonymity in a huge gathering. Tonight's smaller audience will allow your punishment to be, shall we say much more intimate?" said Roberts.

Sherry looked at him with her eyes flashing in anger and the audience loved it that the diabolical Principal always found ways to make Sherry defiantly angry only to have her resistance broken down as the session progressed and turn her finally into a cowering submissive, ostensibly despite her will.

"You are a sadistic bastard," said Sherry angrily.

"That I am. That I am," admitted the Principal.

"Well this is your first session in my newly finished dungeon. Mary has spent quite a few evenings here already," confided Roberts and Mary blushed as everyone looked at her and visualized her naked in the frame, being whipped and paddled.

"In fact both Nancy and Mary volunteered to be part of the proceedings today but I felt it would be unfair to rob you of a chance to be the star of the show," said Roberts emphasizing the word 'show' as he was prone to do.

Sherry again shot him another angry look with her rapidly flashing eyelids making her look incredibly sexy, standing in her cool white shirt that had a tie in front and faded blue jeans that hugged her shapely ass.

"So Sherry, how do you feel about the prospect of being punished by two men you despise strongly?" asked Roberts, pretending to be a TV reporter.

"Furious, Sir. Furious," said Sherry, her eyelids flashing rapidly.

"And how do you feel about being punished in front of your fiancée and your best friend?"

"Humiliated, Sir, but helpless" whimpered Sherry, bowing her head demurely.

"But you are hopelessly turned on by all this?" inquired Roberts.

"No Sir! Absolutely not!" exclaimed Sherry feigning indignation.

"We shall see. We shall see," said Roberts knowingly and everyone smiled increasing Sherry discomfiture.

"Ok Harvey, you shall be the Master of Ceremonies today and Omar is to be the main beneficiary," said Roberts.

"More like the bastard of ceremonies," said Sherry before she could help it.

"You will pay for that," said Harvey sneeringly as he walked up to her and held her by the lobe of her ear.

"Now, apologize to Omar," said Harvey leading her by her ear to the sofa where Omar was sitting.

"I am sorry I got you fired," said Sherry, in a flat tone keeping a passive face.

"You can do better than that," said Harvey plainly.

Sherry knelt before Omar and said, "Omar, I am really sorry I got you fired. Please forgive me?"

This time she sounded much more contrite or at least pretended to.

"And do you deserve to be punished for that?" asked Omar.

"No Sir. But the bastard Principal thinks so," said Sherry honestly and the audience laughed.

"Well then you need to be punished until you are truly repentant," said Omar.

Sherry merely stuck out her tongue defiantly and Omar could not help but admire her spirit. He had seen her naked and spanked a few weeks ago and was about to do the same again and her she was kneeling in front of him and still defiant.

"Ok stand up and request Omar to take down your jeans," said Harvey.

"Here we go again," thought Sherry ruefully as she stood in front of Omar and said, "Omar Sir, will you please take off my jeans?"

Omar was thrilled that he would get to undress this beautiful creature he had a score to settle with.

Omar proceeded to unzip her jeans and slowly peel them down her hips as Sherry stood helplessly with her hands clasped behind her head.

Omar enjoyed the view of her white panties the jeans made their journey downwards and it took him all his self-control not to kiss the gusset of her panties or stroke her prominent mound through her panties.

"Now turn around," he commanded and Sherry turned around to show him her panty clad ass and face the rest of her audience. The white shirt that was tied in front gave them an unobstructed view of her lacy white panties.

"Now let's have a traditional OTK spanking," said Harvey.

Sherry turned around and draped herself over Omar's lap feeling his erection as she did so.

"Turn your head so that we can see the embarrassment on your face as you are spanked by the man you got fired," said Harvey.

"And also make eye contact with yourself in the mirror," continued Harvey.

Sherry used one elbow to support herself as she turned her head and looked at her eager audience and herself in the mirror. Omar looked like he was going to pop.

She could see Matt's boner through his trousers.

Nancy decided to rub it in by saying, "Oh poor Sherry!"

"Now give her ten spanks," instructed Harvey.

Omar rubbed her panty clad bottom and gave her the first spank.

"One, thank you, Sir" said Sherry demurely.

"Two, thank you, Sir!" yelped Sherry as the second spank was a lot harder.

Roberts promptly proceeded to instruct Omar on the need to spank gently.

"The intent is to embarrass and humiliate her, not to hurt her," said Robert.

"Ten, thank you, Sir," said Sherry, as Omar finished his tenth spank.

"Now stand up and ask him to take off your panties," said Harvey.

Omar was delighted that he would soon see his adversary's naked pussy and ass. He had expected to be asked to remove her top first, but Harvey knew that and went in for the surprise.

Sherry gasped and steeled herself for the humiliation.

"Oh poor Sherry. It must be sooo shameful to have Omar take own your panties," said Nancy cattily.

"With friends like this, who needs enemies," pondered Sherry, as she stood up in front of the salesman she had fired.

"Omar Sir, please take off my panties?" asked Sherry contritely yet defiantly with her eyes flashing in anger. She looked at Roberts angrily in the mirror and the audience loved it.

Harvey motioned Omar to wait, deciding to rub in the humiliation.

"So Sherry, contemplate this situation. You complained about this guy and got him fired from his job. And you are now standing in front of him in your panties asking him to take them down and expose your pussy and your ass," said Harvey.

"Yes, Harvey. I am well aware of the situation. Thank you for pointing it out," said Sherry defiantly again.

"Hmmm, I don't think you realize how humiliating this situation is yet. You are asking a person you despise to denude in front of your fiancée and your best friend. I think you need to acknowledge that. Crawl over to Matt and beg him to allow Omar to take down your panties," instructed Harvey.

"Oh no. Why did I have to provoke the beast?" thought Sherry ruefully but the audience was delighted.

Sherry crawled over the carpeted basement floor to where her fiancée was perched and knelt in front of him and asked, "Matt, Sweetheart will you please let Omar take down my panties and expose my naked pussy and ass to the room?"

Matt said, "Hmmm let me think about that."

Sherry shot him an angry look.

"Matt, please? I want this ordeal to be over?" begged Sherry.

"You know how I hate it when you create a scene in a store and complain about customer service. So I am glad you are getting your comeuppance," said Matt.

The audience looked stunned. They had not expected this. Matt had always seemed like a helpless cuckold but now it looked like he was in on the action.

"So I would like you to apologize to me first," said Matt.

Sherry looked at him angrily but decided that it was time Matt became a willing participant rather than a helpless bystander.

"I will not complain about customer service," said Sherry contritely, holding her ears like a penitent schoolgirl.

"Actually, I am going to hold out for a more satisfying apology when you are naked. So now, I give you back to Harvey and Omar," said Matt.

"Great. Now go and ask Nancy to witness Omar taking down your panties," said Harvey.

Sherry again looked incredibly alluring as she crawled over to Nancy slowly swaying her butt as she crawled.

"Nancy, my bff, will you come with me and witness Omar taking down my panties?"

"Oh Sherry sweetheart! You want me to witness your humiliation as Omar, your hated salesman, pulls down your panties and stares unabashedly at your naked pussy?" asked Nancy pretending to be shocked at the suggestion.

"Yes, Nancy. It will only serve to increase my humiliation to have my bff see me like this," confessed Sherry.

"And looks like the humiliation is turning you on," said Nancy pointing to the damp spot in her panties.

Sherry turned ten shades of red and whimpered, "I can't help that!"

"Ok sweetheart. Let's see if we can make this as humiliating as possible," said Nancy as she got up and accepted the leash that Roberts produced. She tied the collar around her bff's neck and made her crawl over to Omar.

"Omar, remember how humiliated you felt when she complained about you in front of the whole store to your manager and how your manager fired you on the spot in front of all your peers. Well here's your chance to have your revenge," said Nancy.

Sherry stood with her hands clasped behind her head with her deer-in-the-headlights look. If events in the past months had made her somewhat immune to public nudity, Harvey, Nancy and worst-of-all, her own fiancée had rubbed in her predicament sufficiently to make her feel as if she was going to be stripped in front of them for the first time.

She stood like a beautiful statue, helpless and yet trembling with erotic excitement.

Omar placed both his hands on her hips and gradually started inching her panties down. Sherry was instructed to make eye contact with Omar and the audience in the mirror alternately and this served to keep her in a constant state of embarrassment as she was not able to tune the whole thing out.

Nancy stood next to her and kept stroking her hair and patting her head and saying, "Oh poor Sherry!" which only served to accentuate her embarrassment.

Slowly, the top of her landing strip came into view and Omar was relishing every second of it as he slowly inched her panties down, pausing to admire the view and rubbing her bottom in between.

He paused and stared at her hypnotized as her panties were down to the middle of her butt with half her pussy with its sparse landing strip showing.

The Principal was right. He had seen her naked before but being able to unveil her for himself slowly in front if a smaller audience was so much more intimate and enjoyable for him and humiliating for Sherry.

"Looks like you have an eager student," remarked Harvey.

"He was never MY student," countered Sherry hotly as if that would reduce her embarrassment.

"Well he is certainly studying you now," said Harvey setting her up beautifully and the audience guffawed as Sherry bit her lip again regretting not holding her tongue.

Omar continued his discovery and finally Sherry's panties came to be resting mid-thigh.

"Spread your legs," instructed Harvey as Sherry sniffed and spread her legs three feet apart giving Omar an unobstructed view of her spread pussy lips.

"Now give us a slow twirl so we can admire you from all angles," said Harvey.

"You mean gawk, don't you?" said Sherry, letting them know that her spirit was intact.

"Well a naked girl is hardly in a position to be debating semantics," pointed out Harvey and Sherry fumed helplessly as she began her slow twirl.

"Keep going," he commanded as she finished her first round.

The audience stared at her wide-eyed and spellbound as she kept doing her slow twirls with her hands clasped on her head, her breasts thrusts forward, legs spread and her panties at mid-thigh only serving to accentuate her naked pussy.

More than the nudity, the fact that they had a gorgeous woman like Sherry at their mercy being compelled to carry out their every command was what turned them on. And secretly, it turned Sherry on too.

"Now keep your panties around your thighs and get over his lap again," instructed Harvey.

Sherry hobbled over and draped herself again over Omar's lap, this time feeling his erection without the protection of her panties.

She turned her head to face her tormentors as well as herself in the mirror and blushed at the sigh of her naked ass resting in the rugged middle-eastern hunk's lap.

"One, thank you, Sir," said Sherry as the first spank landed on her left cheek.

"Two, thank you, Sir," said Sherry as the second spank landed on her right cheek.

"Three, thank you, Sir," said Sherry as she made eye contact with the hated Harvey.

"Four, thank you, Sir," said Sherry as she made eye contact with her bff Nancy who was looking enviously at her, wishing she was in her place.

"Five, thank you, Sir," she said as she made eye contact with her sweetheart who was now unabashedly taking in the sights. He no longer had to pretend that he was a helpless bystander.

"Six, thank you, Sir," she said as she looked into Mary's wistful eyes.

"Seven, thank you, Sir," she said as she made eye contact with the hated Principal, her tormentor in chief.

Perversely and yet strangely defiantly, she chose to hold eye contact with Harvey, her hated rival, for the remaining three spanks.

"Now stand up and beg Omar to strip you completely nude," said Harvey.

Again she was a bit surprised because she had expected to lose the shirt first and the bra later.

She stood up and knelt before Omar so that she could be eye level with him and clasped her hands behind her head and begged demurely, "Omar, Sir, just as I stripped you of your dignity that day in the store, please strip me of my dignity and expose me to everyone."

"Well maybe we should go to the store and strip you in front of everyone there?" inquired and Sherry jumped up, worried that the Principal might devise a way to do that.

"No we can't do that. Make the most of what you can today, son," admonished the Principal.

Omar proceeded to slowly unbutton Sherry's white cotton shirt slowly exposing her white lacy bra. He pondered for a minute taking in the sights before proceeding to untie the knot in the shirt and leave it hanging from the sides.

"Beg me to take off your bra" said Omar.

"Omar, Sir. I have just one shred of clothing left. Please divest me off it so that I may be humiliated for complaining about you," said Sherry, now completely slipping into the role.

"Why do I keep reminding him of my complaint and why do I keep emphasizing that I am getting humiliated in return?" pondered poor Sherry.

"Oh how I wish I could have done this to you in the store that day," said Omar, riled up again by Sherry's reminder.

He took a minute to paw her bra clad boobs before untying the clasp in the back.

He peeled down the straps on both sides off her arms leaving the bra just hanging by her firm breasts.

"Now stand up and jump up and down until the bra falls up," said Omar.

Harvey and Roberts were both delighted that now Omar was coming up with new ways to humiliate their heroine.

Sherry said "Please don't make me do that. That will be so humiliating!"

"Well that is the idea," pointed Omar as Sherry blushed contemplating the ridiculous sight she would present everyone by having to jump up and down until her bra fell off.

But she had no choice and proceeded to stand up and slowly jump up and down again making eye contact with Omar as well as her enthralled audience.

The bra clung to her breasts stubbornly maybe dampened by her sweat and poor Sherry kept jumping until the bra fell off her ample breasts as did her panties and the nubile Goddess stood before Omar in all her naked glory. She blushed again as she saw herself in the mirror and saw her audience staring at her in rapt attention.

Wordlessly, she draped herself over Omar's lap again and begged him to spank her.

She continued to alternate eye contact with her audience as well as herself and sometimes with Omar in the mirror.

"Now let's have you get an intimate OTK spanking from the rest of us," said Harvey after the ten spanks was over and Sherry remained in Omar's lap, waiting obediently for her next instruction.

"Since there is only one sofa, let's have Omar slip over to the end of the sofa and have the spankers come over one by one and take Omar's spot," continued Harvey.

Sherry stood up and Omar slid over to the end of the sofa and Harvey asked Matt to come over.

"Now as you are draped over the spanker's lap, I want you positioned so that your breasts are in Omar's lap. You will still turn slightly so that you can make eye contact with the rest of us as well as yourself in the mirror," said Harvey.

"And also feel free to massage her boobs while she is getting spanked. She enjoys that," Harvey instructed Omar and poor Sherry bristled in indignation.

It felt surreal to her that her fiancée was going to spank her while one of the men she hated fondled her naked breasts.

She used her left elbow to support herself as she turned a little so that she was facing her audience and Omar had access to her breasts.

"One, thank you, Sir," said Sherry as Matt's first spank landed and Omar fondled her breasts gleefully. This night had exceeded his wildest expectations and it wasn't over yet.

"Two, thank you, Sir," said Sherry as she looked humiliated and made eye contact with her nemesis, Harvey.

"Three, thank you, Sir," said Sherry and blushed as she made eye contact with Matt in the mirror.

"This can't be happening. This can't be happening," she repeated to herself but to no avail. The instruction to make eye contact with herself or a member of her audience ensured that she would experience every bit of her chastisement and would not be able to tune it out.

Finally, Matt's ten spanks were over and she stood up to make room for the next spanker who happened to be Nancy.