Sherry's Test

Author's Note:

This story is completely fictional and the characters bear no resemblance to any persons living or dead.

Please read this story in sequence if possible.

Thanks to Kirk2004 for editing this chapter.

Feedback and votes greatly appreciated.

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"The board would like to see you," said a handwritten message, and Sherry squirmed as she wondered what it was about as she followed Penny to the board room.

She knocked and entered, looking anxious. She met the board members a few times. There was Mr. Cremer, a fifty something banker. There was Mr. Morrison, a retired Principal in his late sixties. Finally there was Mrs. Griffith, a fifty something economist.

The Principal welcomed her and asked her to sit.

"The board learned about your punishment sessions and would like to see one. Apparently, one of the parents plays golf with Mr. Morrison and spilled the beans," said the Principal not looking too comfortable that his heinous activities had been discovered by the board.

Sherry looked at the board members pleadingly and said, "Please? I have been punished enough?"

"Well, we would like to be the judge of that," said the retired Principal.

Mrs. Griffith looked at the others and said, "Let me have a word with her in private."

The others nodded and Mrs. Griffith gently led Sherry outside.

"I can't believe what you have been put through, Sherry. You could have put a stop to these sessions a long time ago. Surely you know that?" said Mrs. Griffith.

Sherry remained silent and bowed her head, but the fact that she didn't express surprise told Mrs. Griffith all she wanted to know.

"So you enjoy this at some level, don't you?" asked Mrs. Griffith.

Sherry turned red in embarrassment and again bowed her head submissively.

"You know we can stop it right here and fire the Principal and most of the staff. So it is up to you if you want to continue," said Mrs. Griffith.

Sherry pondered for a minute, looked confused, and answered honestly. "I am confused. I don't know what to do."

"So you would rather be told what to do and feign reluctance so that you don't have to admit that you are actually turned on by public humiliation?" said Mrs. Griffith bluntly but in a kind and sympathetic voice.

Sherry looked at her and decided to just hug the older woman.

"It's Ok, Sherry. Your secret is safe. Plus a lot of men seem to get turned on more when they think there is some degree of reluctance or embarrassment," continued Mrs. Griffith in a gentle tone again.

"But the embarrassment is real," assured Sherry.

"Yes, I know, sweetheart. I am in a submissive relationship myself," revealed Mrs. Griffith.

"Although I was never made to submit so brazenly in public settings," she continued.

Mrs. Griffith almost envied Sherry for her experiences.

Sherry's face lit up at meeting a woman who understood and again hugged her for support.

"You won't think I am just a cheap submissive slut?" she asked.

"No, I won't, sweetheart. In fact, I look forward to experiencing this vicariously, so thank you for this. One of these days, I might return the favor and have you come over and witness my punishment at home," said the kindred spirit.

"Let's get the show on the road then," said Mrs. Griffith, and Sherry blushed at the pun.

Mrs. Griffith led Sherry into the room and said, "Ok. I have managed to convince Sherry that she has not indeed been punished enough, and she has agreed to let us participate in her chastisement."

Mr. Morrison and Mr. Cremer almost rubbed their hands in glee and now openly stared at Sherry, undressing her with their eyes.

"Sir, can you call Matt, please?" asked Sherry.

"Do we really need him here?" inquired Roberts.

"We had a deal," reminded Sherry.

Roberts nodded but didn't look too pleased at having to delay the session. On the other hand, it served to increase the tension by keeping the board members waiting.

Penny was asked to summon Matt as Mrs. Griffith looked at Sherry and wondered if Sherry wanted Matt there because she felt safer with him there or whether it just heightened her humiliation.

"Oh, Matt, you won't believe this but the board wants to punish me! Any respectable board would have put an end to these humiliating sessions, but these guys just want to join in the fun and humiliate me further," said Sherry as Matt entered the room puzzled about what was occurring.

Morrison and Cremer squirmed as they didn't know where this was going. Matt, despite his meek and mild demeanor, was tall and muscular and quite capable of giving three older men a thrashing if needed.

"But I have agreed," said Sherry. "For this one time and one time only."

She was making it clear that she wasn't going to let these punishment orgies spin out of control.

Roberts nodded, not too displeased because he felt uncomfortable having his superiors involved on a routine basis. One session was fine. It would make them complicit and ensure their silence, but having them involved more than that would undermine his authority, and he clearly enjoyed being in charge.

Morrison, Cremer and Griffith nodded in assent, albeit a bit reluctantly.

"Matt?" inquired the Principal, and Matt positioned the chair in front of the mirror and led his sweetheart to the chair.

Sherry knelt on the chair with her pretty brown floral dress and looked at her eager audience and blushed. Her audience was spellbound at the sight of this beautiful teacher kneeling in her formal dress, blushing prettily waiting for her ordeal to begin.

Without waiting for further instructions, Matt gave her ten gentle spanks, and her new audience witnessed the slight wince and blush and lowering of eyes every time a spank landed.

"Cremer, sir?" asked Roberts.

Cremer jumped up and stood behind Sherry and started spanking her.

"Ouch!" said Sherry as the first spank was a bit hard.

"Sorry, I am new to this," apologized Cremer, remembering the Principal's instructions on gentle spanking. He continued spanking her gently, taking the time to look into Sherry's beautiful eyes after every spank.

Soon his ten spanks were over and Roberts invited Morrison to have a go.

Mrs. Griffith decided to pass, preferring to just watch.

"Ok that was the warm-up. Sherry, face the board and take off your dress," said Roberts.

Sherry blushed and got up from her seat and faced the board and took off her pretty brown dress, now standing before them in her cream colored slip.

"Let's have the slip off too," said Roberts to her audience's delight.

Sherry blushed again at the thought of disrobing in front of a new audience. Despite having done this more than a few times over the past couple of months, she wasn't used to it.

"I will never get used to this," she pondered as she took off her slip and stood in front of her stunned audience in her delectable lacy cream colored bra and panties.

Morrison and Cremer looked like their eyes were going to pop out. Mrs. Griffith looked enviously at Sherry, thinking that even when she was younger she was never as beautiful as the woman standing in front of her looking embarrassed and demure with her head bowed slightly.

Roberts let her stand there for a couple of minutes as the audience admired her unabashedly and then led her back to the punishment chair.

Sherry knelt preparing for the next round of spanks, and Roberts surprised her by slowly pulling her panties down and letting it rest in the middle of her thighs. Having it rest there rather than taking it off altogether somehow made her look more alluring, and her audience stared spellbound while Sherry blushed, watching them stare at her naked butt.

The Principal always varied her disrobing so that she never knew what to expect. She had expected to be spanked over her panties first, but the bastard had surprised her taking her panties down and not letting her get used to the idea that her ass would be revealed to the board. Sherry nervously tapped the top of the chair with her hands as she knelt, waiting for her spanking to begin.

"Remember to count," admonished Roberts, and Sherry nodded and rolled her eyes.

Morrison went first this time and took his time to stare at her luscious cleavage in the mirror and her round, firm butt.

"One, thank you, Sir," said Sherry as Morrison looked in turn astonished and then pleased and then incredibly turned on.

He prolonged his ten spanks as long as he could and hurried only when Mrs. Griffith said, "Sometime today, Morrison!"

Next Cremer finished his ten spanks again taking his time, and Mrs. Griffith did not pass her turn this time.

"You are terribly turned on, aren't you?" she whispered sensuously in Sherry's ear, and Sherry blushed averting her eyes.

"One, thank you, ma'am," said Sherry as the first spank landed.

"Are you looking forward to being forced to expose your pretty pussy to Morrison and Cremer?" Mrs. Griffith whispered again.

Sherry squirmed and remained silent.

"Two, thank you, ma'am," she said as the next spank landed.

Mrs. Griffith again leaned over and whispered, "You are a naughty girl, aren't you?"

Sherry nodded and said, "Three, thank you, ma'am," as the next spank landed.

"Would you like to show your firm boobs to the board?" whispered Mrs. Griffith as Sherry squirmed again and stayed silent as Mrs. Griffith gave her the next spank.

"Would you like to be made to kneel naked in front of the board and have us look at your submissive boobs and pussy?" whispered Mrs. Griffith as Morrison and Cremer wondered what was going on. Roberts and Matt of course had a clue and smiled.

"Five, thank you, ma'am," said Sherry.

"You find this intoxicating, don't you?" asked Mrs. Griffith.

"Six, thank you, ma'am," said Sherry as another spank landed, and she winced and looked in the mirror at her admiring audience soaking in the sights.

"And would you like to crawl naked in front of all of us to show how submissive you really are?" whispered Mrs. Griffith.

"Please no!" Sherry pleaded.

"And if we stick our fingers in your pussy, are we going to find it sopping wet?" asked Mrs. Griffith, and Sherry blushed furiously, averting her eyes.

"Eight, thank you, ma'am," she said as the eighth spank landed.

"Would you like to lean back on the couch and spread your legs wide so that we can all see inside your pretty pussy?" teased Mrs. Griffith.

Sherry shook her head terrified.

"Would you like to then pull your legs up and play with yourself in front of the board?" tormented Mrs. Griffith before she gave her the tenth spank.

Sherry was squirming at the excitement of that exquisite teasing and, even though she had experienced everything that Mrs. Griffith had teased her with, the thought of doing it in front of the board disgusted her. She hoped it wouldn't come to that.

Roberts pulled up her panties and got her to stand up and face the board.

"Take off your bra," he said in a matter of fact tone.

Sherry looked at her eager audience and bowed her head as she reached back and unhooked her bra, taking it off to let her ample firm breasts come into view.

"Wow," said Morrison.

"Those are beautiful breasts, Sherry!" said Cremer.

Sherry blushed at the compliments and bowed her head. Roberts thought of reminding her to make eye contact, but she looked so bashful and appealing with her head bowed standing bare breasted in her panties that he decided to let it go.

"Panties," he said casually causing Sherry to give a startled jump.

She again hoped for a gradual disrobing, and the Principal again surprised her. She looked at Matt who shrugged as if to say, "It's going to happen sooner or later anyway."

She started inching her panties down slowly pausing to look at her audience as the top of her trimmed bush came into view. The respectable board members looked on like excited teenagers. Sherry almost smiled at their juvenile enthusiasm as she peeled the panties the rest of the way.

"Leave it around your thighs," instructed Roberts as the panties descended to just above her knees.

Sherry knew the bastard enjoyed watching her hobble with the panties at half mast.

"Now go over to each of the board members and ask them to look at your naughty pussy," said the Principal.

"Please take a good look at my naughty pussy," said Sherry as she hobbled over to Mr. Morrison.

Morrison gazed at her beautiful trimmed bush and her swollen mound which was visible through the scant pubic hair as he nodded in appreciation.

Sherry then hobbled over to Cremer who stared at it as if he had never seen a pussy before.

Mrs. Griffith looked at her and said, "Beautiful, just beautiful. I think you are turning me into a lesbian, Sherry."

Sherry blushed and wondered what it would be like to have her pussy licked by a woman.

Roberts then led her back to the chair and proceeded to give her ten spanks while cupping her breasts. Morrison and Cremer looked as if they were going to shoot their load, and, if they were alone, they might have even jacked off while watching the mind-blowing sensuous scene of the gorgeous Sherry being spanked with the Principal's hands on one of her breasts and the other one free for them to admire. As usual Sherry looked infinitely submissive and demure and blushed throughout the ordeal.

Morrison was next, and he was delighted at the feel of Sherry's left breast in his left hand and her ass on his right hand as he stroked both with glee. Sherry tried looking at the ceiling, but the Principal reminded her to make eye contact in the mirror. When she did, she saw Matt looking at her terribly turned on and yet angry that Morrison was taking such liberties with her.

"This is a spanking session, not a groping session, Sir. Please get on with it," admonished Matt.

It was Morrison now who looked humiliated at being ticked off by a junior teacher but had the decency to blush to apologize to Matt.

"I am sorry, Matt. It won't happen again," he said contritely.

Morrison finished his ten spanks followed by Cremer. Both took infinite delight at seeing Sherry count out each one.

Mrs. Griffith decided to pass again.

Roberts walked over and made Sherry stand again and asked her to step out of her panties completely and face her audience who just could not get enough of her.

Sherry stood before the board naked but for her stockings and high heel shoes that served only to accentuate her nudity.

"Sherry, put your hands on your head and apologize to the board for compromising the high standards of education in the school," said Roberts.

Sherry could not believe the hypocrisy of the Principal and thought of coming back with a retort but knew that it would only prolong her session. She decided to just go along with it.

"I am sorry for compromising the high standards of education of this respectable school," said Sherry not without a hint of sarcasm.

The board member smiled at the sarcasm and admired the view of the contrite, naked school teacher with her hands on her head and her pussy now glistening.

"Sherry, are you turned on by your humiliation?" asked Roberts politely.

"No!" exclaimed Sherry instinctively, despite realizing that evidence of her arousal must be there for everyone to see.

"All right then. We will ascertain that for ourselves. If we find out your pussy is wet, then we will take it as indication that you want these punishment sessions to continue. If it is dry, then we will immediately bring these sessions to a halt and issue you a formal apology," said Roberts.

"Oh no!" thought Sherry, kicking herself for lying about it.

"Sir, I am fine with my punishment sessions continuing," said Sherry hurriedly.

"Well, our high standards of education dictate that we must verify for ourselves," said Roberts, causing the board members to snicker at the sadistic Principal's shameless ploys.

"So continue to keep your hands on your head and go and stand before each of the board members. Have them verify if you are wet or not," said Roberts.

"Sir, please don't! I was mistaken. I am wet. Let these sessions continue," pleaded poor Sherry.

"As I said, you have lied before. So we have to ascertain for ourselves," said Roberts.

Sherry braced herself for a new humiliation and stepped over and stood in front of the seated Mr. Morrison.

Morrison gazed admiringly into her pussy and gingerly stuck a finger in her pussy and found it to be deliciously wet. He sniffed his finger to smell her arousal as Sherry blushed uncontrollably and then held it up to her nose.

"It is indeed wet," he pronounced.

"Ok, so we have determined that. No need to go any further," reasoned Sherry.

"Nope, I want all the board members to inspect you. We would be derelict in our duties if we merely took each other's word in the running of the school," explained Roberts.

Sherry went and stood in front of Mr. Cremer who again took his time admiring the pussy so close to his face and then gently stuck his finger in.

"Yup, it is wet," he pronounced as he stuck his finger in Sherry's mouth and made her taste her own juices.

She then walked over to Mrs. Griffith who stuck her finger in and decided to taste it herself.

"Deliciously wet," she pronounced.

"Ok. You are going to get one final punishment for lying to us, and then we are done for the day. Wait here," said Roberts as he stepped out of the boardroom to go to his office.

He returned holding a play whip and a play strap that he had bought from Spencer's.

He gave it to Matt and said, "Matt, I would like you to gently whip your girlfriend all over her body as a punishment for lying."

"Oh God," thought Sherry as Matt seemed unexpectedly enthusiastic in grabbing the implement from the Principal and walking over to her.

"Sherry, sweetheart, I am insanely turned on as are you. DO you mind if I get into the act a little and enjoy myself?" he whispered in her ear.

Sherry blushed at the thought of her boyfriend putting her through her paces in front of the board, but they had a great relationship. Matt had been a sweet, caring partner in everything.

"Go ahead, sweetheart. Have at it," she whispered back.

Matt loosened her ponytail and moved her long flowing hair in front of her in between her breasts. A few strands brushed each of her breasts, but most of them flowed in between and settled exactly in between her breasts making her look so much more alluring.

He then knelt in front of her and gently slid the play whip over her fleshy mound with a little of it going between her pussy lips. Sherry squirmed in arousal almost thrusting her hips to increase contact with the whip.

She looked at her audience, staring at her in awe and hung her head in shame, thinking of her uninhibited display of pleasure just a second ago.

Matt then stood up and gently whipped her breasts as she squirmed and came close to a climax.

He then went behind her and whipped her curvy back, the top of her shoulders, her ass, and then her thighs and calves as her audience gawked at Sherry squirming under the humiliation and arousal.

He then took the strap and strapped her breasts and then her flat stomach. He held up her left leg to strap the inside of her thigh and this caused her pussy to be revealed even more to her captivated audience. She looked incredibly vulnerable standing naked with her left leg raised up with her glistening pussy on display.

Matt moved over to the other side and raised her right leg to strap the inside of her right thigh. He then strapped her pussy lips gently, causing her to spiral out of control and come close to an orgasm. Matt recognized the signs and kept gently slapping her pussy with the strap, while kneading her left breast as she arched her back and raised her face and climaxed and then hung her head in shame that the board members had witnessed this very private act.