Sherry's Test Ch. 15A

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.

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The annual fundraiser was held at BK Enterprises 24th floor downtown office executive lounge. The lounge was exquisitely decorated with Victorian furniture, French windows overlooking the city, beautiful chandeliers hanging from the ceiling. Needless to say, there was no shortage of mirrors on the walls, because Roberts had made sure of that.

When Sherry was asked to attend, she knew what to expect and feared the worst. Nancy and Lara were asked if they were interested in volunteering and they had jumped at the opportunity.

"But I want you to feign reluctance and act very bashful. That turns people on much more than wanton exhibitionism," chided the Principal and both Nancy and Lara feigned indignation at the Principal's insinuation and protested that they were volunteering in order to give their sister company and alleviate her mortification.

"Great. As you can imagine the more turned on the sponsors are, the more they will inclined to contribute. Last year's play staged by the students while not lacking in theatrical merit failed to inspire greater contributions from our patrons," rued the Principal.

So on the night of the fundraiser, Sherry, Nancy and Lara walked into the executive lounge accompanied by their boyfriends. The other teachers were denied admission much to their chagrin.

The sponsors were already moving around the lounge and as Sherry walked into the room, Roberts went over to her and whispered his instructions.

"No!" gasped Sherry audibly, causing those within hearing range to look at her with curiosity which only served to make Sherry blush even more.

The Principal again leaned forward and whispered something in her ear and Sherry looked at him pleadingly with her typical 'deer in the headlights' vulnerable look. Matt and the other teachers were puzzled as to what the principal was asking her to do which would cause her such acute embarrassment after all she had been put through over the last month.

Roberts gestured silently as if to say, "Just go and do it."

Sherry looked terrified and walked towards the restroom that Roberts had pointed.

Roberts asked Nancy and Lara to be seated on one side of the room and addressed the school's patrons.

"Ladies and Gentlemen, welcome to this year's fundraiser. We hope that tonight's entertainment will inspire you and move you to open our wallets further than last year and contribute generously. As you know, the government keeps cutting our funding every year and if it wasn't for the generosity of patrons like you, we would find it extremely difficult to uphold the high standards of education that Riverdale High has been associated with. Having said that, tonight we will be taking a welcome break from serious matters of education and creating an offering of pure escapist fare. Adult escapist fare if I may add. I have spoken to each one of you before tonight and each one of you has assured me that your sensibilities will not be outraged by anything we may have to offer. However, if at any point, you find yourselves objecting, please feel free to come and talk to me. Needless to say, you may leave at any point," said the Principal pausing before adding "After emptying your wallet of course," causing the audience to laugh.

They had all known the Principal personally and gone to strip clubs with him, and they were curious as to what he was making a big deal out of.

"Please help yourselves to the drinks and refreshments that Gavin has so generously provided as I will bring the lady teachers around one by one and introduce them to you," said the Principal.

Sherry tiptoed through the room, looking stunning in her gorgeous red dress and walked over to Roberts with her right hand balled up.

Roberts looked at her approvingly and led Sherry by her left hand over to Gavin, the sixty year old tycoon who obviously identified with Gordon Gekko and had a Michael Douglas like hairstyle.

"May I present to you, Sherry, one of our star performers," said Roberts looking completely outclassed by Gavin, but still devilish enough to hold his own.

"Delighted to meet you, Sherry," said Gavin as he extended his right hand. All of Gavin's exposure to kinkiness had not prepared him for what happened next as Sherry opened her balled fist to reveal her red lacy Victoria's Secret panties which she transferred to her left hand before shaking Gavin's hand. Gavin's eyes widened with excitement as he tried to imagine Sherry without her panties under that gorgeous dress and poor Sherry blushed from head to toe.

"Honored to meet you, Sir," she said bravely.

"You will be seeing more of her later," said Roberts and Gavin did not miss the obvious innuendo as his face displayed visible anticipation of things to come.

"Damn I am lucky, I haven't had to deal with this bastard in the corporate world, if he is capable of pulling surprises like this," mused Gavin.

He then took Sherry over to Boris and the polished Russian also did a double-take when Sherry's fist opened to reveal her panties before she switched it to her left hand. She had to briefly hold it up with her two fingers so that there would be no doubt as to what it was.

Despite all the humiliations, Sherry had gone through, she still found having to go around an exquisite lounge full of immaculately dressed gentlemen with herself being immaculately dressed but with panties in her hand infinitely embarrassing and she blushed beautifully at every introduction.

Next was Nigel, the British industrialist and his stiff upper lip training proved unequal to the provocation of a beautiful lady dressed elegantly opening her fisted right hand to reveal her lacy panties and blushing so prettily. Needless to say, his jaw dropped and he drooled at the thought of Sherry's naked pussy under the dress.

Next was Simon, another Brit who was not in the same class as Nigel, though equally wealthy.

"Delighted to meet you Sherry dear and pray what might you have in your pretty little hand," he asked increasing her mortification ten-fold.

"My panties, Sir," said Sherry reluctantly and shyly.

"And why do you have your panties in your hand?" asked Simon.

Sherry looked at Roberts who appreciated her deferring to him and patted Simon and said, "All will be revealed to you shortly, old chap," laying an emphasis on the word "revealed."

Sherry blushed again at the sight of Simon drooling as he undressed her with his eyes.

The last was Gertrude, a woman in her early fifties who was the CEO of a mid-size company.

As had happened with the school board, Sherry found the presence of a woman at once reassuring and mortifying. Reassuring because she felt she would garner some sympathy from her and mortifying because a woman would be much better able to understand the mix of feelings that Sherry would go through and also be able to sense her arousal much earlier than the men. And with a woman, there was also the risk of censure that would only serve to increase her humiliation at her moment of capitulation, at the moment that the excitement of the humiliation would exceed her reluctance and modesty and she would start enjoying her arousal openly without regard to who was watching.

Gertrude smiled knowingly when she saw her panties and whispered in Sherry's ear, "You liked to be forced to do these things, don't you?"

Sherry blushed prettily but remained silent which more or less confirmed what Gertrude has suspected.

The Principal then introduced Nancy and Lara without pulling any stunts which only served to heighten the suspense as to what their role would be in the proceedings.

"And lastly, here is my wife, Mary. Lest you get any ideas, she will not be part of the proceedings as such, but she has graciously agreed to be our hostess and make sure we are amply supplied with food and drink. She will also be helping manage your pledges to the school. She has game room style tokens that you can buy and use tonight.

Each token is worth $1,000," said the Principal.

The donors bought 50 tokens each and settled down with a glass of red wine, waiting for the proceedings to begin.

"Ok. For the first part of the show," said the Principal with emphasis on the word show, "Sherry here was caught leaking a test to a student she had a crush on and has agreed to atone for her indiscretion and help raise money for the school by auctioning her clothes. She has also agreed to be spanked for her sins," he continued, as everyone eyed Sherry causing her to turn hot with embarrassment.

Roberts then arranged a chair in front of the mirror and Sherry, without waiting for her cue, went over and knelt demurely on the chair. The Principal adjusted her slightly so that her butt stuck out invitingly and proceeded to instruct everyone on the gentle art of spanking.

Sherry blushed as he demonstrated and she readied herself for the ignominy of being humiliated before a fresh group of people.

"Ok here is a box for dropping your tokens. Ten spanks for one token. Who would like to go first?" asked Roberts.

Nigel stood up and walked over and dropped his token and proceeded to spank the beautiful Sherry as the group watched the mix of embarrassment and excitement on her face.

"Ok now who would like to relieve her of her dress?" Roberts asked.

Gavin stood up and walked over in confident, measured strides and said, "The pleasure is entirely mine."

He raised Sherry from her chair and stood her in front of the mirror and slowly peeled the strapless red dress off her to leave her blushing in her pink slip.

She knelt on the chair again and this time Gavin proceeded to spank her. Roberts reminded her to count and Sherry shot daggers at him but complied meekly with "One thank you, Sir" and so on until the ten spanks were done.

"OK. Now who would like to take her slip off?" asked Roberts and as Boris came over, Sherry and the group realized that since she was not wearing her panties, her pussy would be on show.

Boris turned her around, unhooked the straps of her slip and knelt before her and peeled it off her with agonizing slowness, first to reveal her red lacy bra and then her flat stomach and then slowly her landing strip with her luscious mound visible through her sparse hair came into view.

Her firm round ass was visible in the mirror and her audience patiently waited for Boris to step away so that they could have an unobstructed view of her pussy. Boris after taking a full minute to admire the Goddess standing before him demurely in just a red lacy bra stepped aside to let the group feast on her nakedness.

"Anyone for her bra?" asked Roberts and Nigel raised his hand and came over.

He turned her around to face the mirror, unhooked the bra and slowly slid the straps down leaving the cups hugging her breasts until he peeled it off sensuously and Sherry blushed at her naked reflection in the mirror and her enthralled audience staring unabashedly at her. Gertrude was clearly a bi if not a lesbian because she seemed as turned on as anyone else.

She knelt on the chair again and the Principal asked Matt to demonstrate Sherry's naked spanking. Matt blushed and walked over to his beautiful fiancee and proceeded to cup her left breast while spanking her on alternate cheeks and the group stared wide-eyed and excited at the prospect of getting to paw her naked breast while spanking her naked ass.

"Ok. Five tokens for this privilege," said Roberts and there were no objections as one by one all of them proceeded to spank Sherry.

Sherry expectedly was incredibly humiliated and insanely turned on at the same time. Having to make eye contact with her audience, feeling their hands grope her breast, having their hands caress her ass before slapping it, having the audience watch her wince so prettily and then demurely count out her strokes while everyone else was completely dressed in formal attire was too much sensory overload and poor Sherry was dripping wet.

And then there were the inevitable questions to rub in her humiliation.

"How does it feel to stick your naked butt out to be spanked by a stranger in front of your fiancée?"

"Do you enjoy being spanked in public, Sherry dear?"

"Please let me not leak on this chair for everyone to see," she prayed fervently.

Roberts walked over to Sherry and whispered, "Sherry sweetheart, are you turned on?"

"Yes sir," moaned Sherry.

"Ok you have a choice to make. For the rest of your punishment, you can either have your kind fiancée be your master or you can have your hated nemesis Harvey really humiliate you. If you choose Matt, you will not be allowed to cum. If you choose Harvey, you will be rewarded by being permitted to have the mind-blowing orgasm you deserve. Your choice," whispered Roberts.

The audience looked at the two wondering what was happening but sure that they would be in for a treat no matter what.

Poor Sherry looked at Matt and then at Harvey and pondered her decision. The prospect of having to go through the whole evening without being allowed to cum seemed be an unbearable torture, but to be publicly humiliated by Harvey?

"Oh god, that would be terrible. But my pussy seems to be throbbing with that prospect. I am turned on at the thought of Harvey making me crawl through the room and kiss everyone's feet," she realized to her horror.

"Harvey, Sir," said Sherry bowing her head.

"Are you sure?" asked Roberts.

"Yes, Sir," said Sherry shyly.

"Final answer?" asked the Principal rubbing it in.

"Yessss," hissed Sherry.

"Very well then," said Roberts turning to the sponsors.

"You are in for a treat. For the next hour, Sherry will be a slave to her chosen master who punish and humiliate her in front of you. The price is 30 tokens from each of you. At the end of it, if you are not satisfied, you may have your tokens back," said Roberts.

Mary collected the tokens as the audience looked wide-eyed in anticipation.

"The interesting thing is that Sherry has chosen as her master, her hated rival Harvey thereby choosing to make her humiliation that much more abject," said Roberts conveniently omitting the reason Sherry made that choice.

Matt looked at Sherry surprised and poor Sherry shrugged and looked at the ceiling.

"But Harvey has to first accept the slave, so Sherry, you will crawl to Harvey and kneel before him and beg him to be your master for the evening," instructed the Principal.

Sherry got down from her chair and before the audience could soak in the sights of the naked form, she got on all fours and crawled towards the leering Harvey.

"Harvey, Sir. Will you please accept me as your slave for the evening?" she asked flushing with humiliation.

"Beg," said Harvey.

"Harvey, Sir. I beg you to accept me as your slave for the evening," pleaded Sherry.

"Beg like a dog," said Harvey.

Sherry sniffed and held her hands in front of her like a kneeling dog begging for food and said,

"Harvey, Sir. I beg you to accept this worthless doggie as your slave for the evening. I beg you to humiliate me in front of all the guests," she said not believing the words that came out of her mouth.

"Sherry!" exclaimed a surprised Nancy followed by an equally surprised Lara.

"Go ask your best friend Nancy if she is OK with allowing her boyfriend to be your master," said Harvey.

Sherry crawled over to Nancy and begged her, "Nancy, my best friend, will you please allow your boyfriend Harvey to be my master for the evening?"

"Sure dear. Whatever turns you on," said Nancy patting her head lovingly.

"Now go and ask your fiancée's permission," said Harvey.

"Oh god, this will be so humiliating. Why did I agree to this," wondered poor Sherry as she crawled over to her gentle fiancée and made her demeaning request.

"Yes. And I still love you very much," said Matt understandingly.

Sherry fell in love with him all over again at that unconditional acceptance of her and almost changed her mind to go through with it. But she was too far gone to be able to withstand the torture of not being allowed to orgasm all evening.

She gave Matt one last adoring look and whispered, "I love you very much too," and crawled over to Harvey.

She was surprised to see Harvey holding a leash. Obviously, Roberts had come well prepared with the required paraphernalia for the evening.

She had been made to crawl in front of her colleagues and guests but to be actually led by a leash by no less than her hated rival was abject humiliation and she squirmed with the heady mix of humiliation and excitement.

She held neck demurely for the collar as her disbelieving audience looked on.

"Now let the sponsors have a good look at you," said Harvey as he led her to Nigel.

She was asked to stand in front of Nigel so that he could get a good look at her full frontal nudity and then she was asked to give a slow twirl so that he could admire her gorgeous naked form from all angles.

And then Boris who took his time staring at her nicely trimmed landing strip and the pussy lips visible through the scant hair as Sherry stood blushing uncontrollably with Harvey holding the leash around her neck.

"God I would love to whip her," said Boris.

"All in good time, Sir," assured Harvey as Sherry pondered the prospect of being whipped in front of her posh audience.

Gertrude looked at her the way a dominatrix would, causing Sherry to squirm.

"Thank, God, she is not in charge of my punishment", thought Sherry.

"Kiss my feet," commanded Gertrude, as Sherry sniffed, held back a tear and knelt before the formally dressed Gertrude and kissed her black stocking clad feet.

Nancy squirmed in her seat and wondered what that must feel like and was sure that she would find out when it was her turn later that evening.

"Now kiss your best friend's feet," said Harvey as he led her by her leash to Nancy.

Nancy looked on wide-eyed in excitement as her naked best friend got on all fours in front of her and kissed her feet lovingly.

"Oh Sherry," moaned Nancy and poor Sherry looked at her and blushed with shame.

Harvey then led her to an empty couch and took off her leash.

"Ok. Here is what we are going to do. Each of the sponsors will get to experience the joys of an OTK spanking. They are going to sit on the couch with Sherry draped over their knees. Matt is going to sit next to them so that Sherry's head is in her loving fiancée's lap. Her head is going to be turned and facing the audience so that we can admire her blushing face," instructed Harvey as Roberts looked at him admiringly.

"Boris, will you care to be first?" asked Harvey and Boris found himself more than willing. He came and positioned himself in the center of the full length couch and gawked at Sherry as she stood before him momentarily before draping herself in his lap. Matt came and sat at the edge if the couch and Sherry's breasts and head lay in his lap. She turned her head to see all her colleagues and the guest standing in front of her staring at her unabashedly. Her naked rump rested alluringly in Boris's lap, with Matt's left hand on her breasts and right hand stroking her head lovingly and her enthralled audience looking at her beautiful vulnerable face.

"One, thank you, Sir," said Sherry as the first spank landed on her butt. It felt incredibly surreal to have her head in her fiancée's lap while a stranger in a thousand dollar suit spanked her naked ass in front of an audience.

"Two, thank You, Sir" said Sherry as Boris continued after rubbing his hands over her gorgeous ass.

Soon the ten spanks were over and Sherry stood up and waited for Nigel to come over.