Sherry's Test

This is a continuation of the Sherry's Test Series. It will make more sense if it is read in order but each chapter stands on its own.

This chapter contains light BDSM and humiliation.. It does NOT contain any hardcore sex. It is mainly about submissive females and dominant males.

This story is meant as a completely fictional, unrealistic fantasy and the characters bear no resemblance to any real person.

Feedback, votes and comments greatly appreciated.

All copyrights for the series reserved.

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The Friday festivities at the Principal's house returned after a week's respite and Sherry was ushered in by Mary to her guest bedroom.

"Ed wants you to wear this," she said pointing at the school girl uniform.

"Oh God! Ed is here," thought Sherry with mixed feelings as she contemplated another evening of humiliation in front of her mentor.

She disrobed without a fuss and put on the school girl uniform with white blouse, grey skirt and tie. The uniform was a couple of sizes too small for her and it served to accentuate her curves and boobs.

"Very cute, Sherry," said Mary as she walked behind her and tied her hair in a ponytail.

"Kneel in the corner until you are called," said Mary leaving the room.

After about fifteen minutes of kneeling, Ed came in to escort her to the basement.

"Is the naughty girl ready to be punished?" inquired Ed taking in her ravishing form shown to advantage in the schoolgirl uniform.

"Yes Sir," said Sherry and turned and knelt in front of Ed.

"You know, Sherry, much as I have enjoyed the previous two sessions, I was a bit restrained about it. But I am moving to Australia in a month to be with my son and daughter. So today, I am going to indulge myself without inhibition," said Ed.

"Ed, I am still shy in front of you but please don't hold back," said Sherry, strangely pleased to be able to make her mentor happy despite the impending humiliation.

"Are you sure? If so, I will indulge myself to my heart's content to have a night I will not forget," said Ed, stroking her head.

Sherry blushed prettily and said, "Please do, Sir."

Ed asked her to stand and led her by her ear down the stairs to the basement. The audience clapped as they took in her delectable form.

She noticed the usual suspects in the audience - Roberts, Mary, Matt, Harvey and Nancy but she was mortified to see Tammy.

"Oh God!" she thought as Tammy stared at her mentor dressed in a schoolgirl uniform that was too tight for her.

Ed gave his camcorder to the despicable Harvey and Harvey gleefully started recording the proceedings.

Ed made her stand in the center of the room in front of the mirror and raised her skirt and bunched it up in her waistband from the front as well as the back.

"Take your panties down," he commanded and Sherry was surprised at the lack of build up and took her panties down to her knees blushing furiously as her shaved pussy appeared in view.

Ed stared at her bare pussy, framed by the grey skirt and white blouse with grey tie, longingly and proceeded to stick his finger in her pussy and ask, "Have you been a naughty girl?"

Sherry had never seen Ed like this and was shocked but reveled in the humiliation of having Ed stand in front of her with his finger in her pussy with Harvey standing beside him and filming it.

"Yes Sir. I have been a bad girl," said Sherry.

The Principal handed Ed a ruler and he proceeded to hand spank her with the ruler and her audience again noticed how pretty Sherry looked when she winced.

"Ten thank you, Sir," said Sherry as the tenth hand spank landed.

"Now let's have you jogging on the spot. But keep turning slowly as you do so," said Ed.

Sherry stepped out of her panties and started her slow jog blushing continuously. The most difficult part of the demeaning act was making eye contact with Tammy who looked incredulously at her mentor. And yet she maintained eye contact with her audience and felt the humiliation make her pussy moist.

After about three minutes of on the spot jogging, Ed asked her to do some jumping jacks.

And then the usual apology squats.

He then led her by her ear to the punishment chair and gave her ten spanks.

Just when she thought she was going to be spanked by everyone, Ed said, "Now stand up, turn around and take off all your clothes except for the tie."

Sherry was surprised that her denuding was not going to be gradual, but stood up and turned around to face her audience.

"Actually, let's have Harvey, your hated rival, strip you," said Ed changing his mind and Harvey handed the camcorder to Ed and happily moved over to Sherry.

"Ed, can I see you for a second?" asked Sherry.

Ed nodded and took her by her hand to a corner.

"Why are you letting that creep debase me like me this?" whispered Sherry indignantly.

"Oh sweetheart. You have no idea how stunningly beautiful you look when Harvey puts you through your paces. You have no idea how much your expressions of helpless indignation combined with reluctant surrender and uncontrollable arousal turn us on. No man would ever need Viagra if he could see that. And surely, it turns you on despite protestations to the contrary?" said Ed kindly.

Sherry looked into his kind yet excited eyes and merely said, "Let's continue then."

She went back to her previous spot and Harvey was waiting for her.

He let the humiliation of the situation sink in and waited mutely staring at her.

Sherry bristled helplessly and as usual it only served to make the situation more erotic. And yet as in the past, being humiliated by her rival in front of everyone got her insanely turned on.

"Ask," said Harvey plainly.

She wished she could wipe the smirk of his face with her soiled panties and instead she had to degradingly beg him to strip her naked.

"Oh God! How can I continue to be so turned on by this," pondered Sherry.

"Harvey, my hated rival, will you please remove my skirt?" asked Sherry, deliberately putting on a sweet smile to hide her discomfiture.

Harvey proceeded to do so and left her naked from the waist down.

"Harvey, my nemesis, please remove my blouse," said Sherry, now wallowing in the fact that the despicable Harvey was humiliating her.

The audience loved the range of emotions her face betrayed and that was one of the many things that made these occasions so special.

Harvey had her swivel giving her audience a 360 degree view of her bra clad form.

"Harvey, you pathetic creep, please remove my bra and expose me to my perverted audience," said Sherry defiantly provoking him and as usual, her repartee was greeted with appreciative laughter.

"You will pay for that," said Harvey as he removed her bra in an agonizingly slow fashion and left her naked except for the tie hanging between her firm breasts, which only served to accentuate her nudity.

"Now I want you to apologize to me for insulting me," said Harvey.

Sherry looked at Ed and he nodded.

Sherry's eyes flashed rapidly in helpless anger and yet she felt her excitement rising.

"I am sorry I insulted you," said Sherry as she commenced her naked squats in front of the leering Harvey and again noticing that her pussy was enjoying the exquisite humiliation of her capitulation before her nemesis with her mentor filming the proceedings for posterity.

"I am sorry I spoke the truth about you," said Sherry with the second squat and the audience laughed.

"I am sorry you are such a creep," she continued as Harvey looked on helplessly as the audience enjoyed her improvisation and her uncanny ability to make Harvey look like a complete buffoon despite her being nude and helpless before him.

Her ten squats were completed with Sherry prolonging it enough to heighten her own humiliation.

"Now go to Tammy and let her see how wet you are," said Harvey and again Sherry was both mortified as well as turned on by this demeaning command.

"Tammy, my protégé, will you please stick your finger in my pussy and see how wet I am?" said Sherry as Tammy looked shocked and yet undeniably turned on.

"Oh my God, Sherry you are pretty wet!" exclaimed Tammy with her finger in her mentor's pussy and Sherry blushed and shrugged.

"Ok. Now let's have you do some jumping jacks again," said Ed and Sherry stood in front of the mirror and performed some jumping jacks and noticed her spellbound audience enjoy the sight of her bouncing boobs.

Ed handed the camcorder back to Harvey and positioned her on the punishment chair and proceeded to spank her.

Ed took the liberty of caressing her boobs while he spanked her and Sherry was shocked at the monster the kind Ed was turning into but yet strangely gratified at her mentor's enjoyment of her naked beauty. She noted that he was fondling her delicately and lovingly and not just groping her aggressively like Harvey would.

He then led her to the punishment frame and proceeded to tie her wrists as well as ankles to cuffs on the frame.

Ed as well as the rest of her audience appreciated how ravishing the vulnerable, naked Sherry looked.

Roberts handed him the customary set of toy whips which were designed not to sting or leave a mark.

Ed chose one and walked over to the helplessly bound Sherry and said, "choose where you want to be whipped."

Sherry squirmed in her bonds, her arousal going up a notch on by the fact that she would have to be an active participant in her debasement.

"Ed, my kind mentor, please whip my tits," said Sherry deliberately choosing the demeaning phrase for her breasts.

Ed proceeded to whip her breasts and then sensuously caressed the whip all over her stomach, her mound and her erect clitoris.

"Ed, my respected mentor please whip my pussy," said Sherry and Ed stepped back and gently whipped her naked mound with Sherry swaying alluringly.

"Ed, please whip my ass," said Sherry and Ed stepped behind her and whipped her ass for a couple of minutes admiring her naked front and blushing yet excited face in the mirror.

"Ed, please whip my back," said Sherry next and Ed proceeded to do so.

And then she asked him to whip her stomach and her thighs and later about ten minutes of fun, Ed asked Tammy to come and do the same.

"I don't want to," said Tammy.

"Yes but she wants to. Your adulation has been too much for her to bear and she wants you to see her and accept her for who she really is," said Ed as Sherry squirmed under the prospect of being whipped by her own protégé, someone who looked up to her as a model of propriety. Her pussy felt otherwise and welcomed the prospect of this new debasement by gushing.

"Yes Tammy sweetheart. Please come and whip your fallen mentor," said Sherry dramatically.

Tammy walked over hesitantly but it was clear from her body language that she was turned on.

"Wondering how it would feel to be in her shoes?" asked Roberts.

"Well she is not wearing any shoes," said Tammy in a sassy voice and the audience was delighted by her humor.

Yes she had learnt well from her mentor and it would be just as delightful to have her be the star of the show.

"Yeah she is not wearing anything except a tie. Which is what you will be wearing when you come here next," said Roberts.

"I will if Sherry asks me to," said Tammy, her eyes wide with excitement, and the audience was thrilled to hear that.

As with Ed, Sherry had to name the part of the body she wanted whipped and she swayed and squirmed helplessly as her protégé proceeded to whip her all over.

"I can't wait for the roles to be reversed," mused Sherry as Tammy whipped her wet pussy.

After her whipping was done, Tammy inserted her finger in Sherry's pussy and gazed into her eyes and whispered, "God Sherry you are soaking wet. You must really enjoy this."

Sherry looked at her mutely, her eyes silently acknowledging the fact.

After the Principal, Matt, Mary and Nancy had their turns, it was Harvey's turn.

"Harvey, my hated rival, please humiliate me by flogging my tits," said Sherry demurely as the delighted Harvey proceeded to whip both her breasts enjoying her helpless turned on expression and the slight wince.

"Harvey, my sworn enemy, please show me my place by whipping my naked pussy in front of everyone.

Harvey stepped by her side, held her face by her chin and gazed into her blushing eyes as he caressed her pussy with the thongs of the whip, letting the strands dart in and out of her sex.

Sherry swayed and squirmed being driven insane by this abject humiliation and even though she had been in similar predicaments quite a few times over the past couple of months, she was still not inured to it. And clearly neither was her audience because they could not get enough of seeing her in such situations.

Harvey whipped her pussy for a couple of minutes and paused.

"Harvey, my nemesis, I beg you to whip my ass," said Sherry.

"Tammy, hand me your panties" said Harvey and Tammy looked shocked but complied by reaching under her skirt and removing her white panties.

Harvey then had Sherry hold her panties between her teeth and stood behind to admire the sight of this naked goddess with Tammy's white panties in her mouth, with her tie hanging between her breasts. The panties were soaking wet and Sherry writhed under the ignominy of having to taste and smell her protégé's arousal.

The audience stared wide-eyed in enjoyment as Harvey proceeded to whip her butt while caressing her boobs.

Sherry, as was her wont, went through a wide range of conflicting emotions with her expressive face betraying every emotion she felt. For the most part she looked helplessly furious as well as hopelessly turned on.

"Please whip my back," muttered Sherry through her clenched teeth and Harvey obliged.

And next it was her shoulders. And then the stomach and her thighs and then she asked to be whipped all over and Harvey made sure that there was not a single spot left unwhipped.

Ed then came over and release Sherry from her frame and made her crawl to the punishment chair.

He made her sit back on it and drape her legs over the sides of the chair leaving her pussy splayed open.

She always found this position excruciatingly humiliating but was now desperate for release.

Ed chose a strap which was again designed not to hurt.

"Please strap my pussy," asked Sherry gazing into her mentor's eyes. Eyes that had always been kind but now looked delirious.

Ed strapped her naked, exposed pussy gently, sensuously rubbing it over her sex in between strikes and Sherry desperate for contact in that area begged for more.

Ed then instructed Harvey to come over and take a turn and Sherry as usual had to maintain eye contact with her nemesis. And yet being splayed open in front of him and having to ask him to strap her pussy and her ass got her close to an orgasm and she was writhing and moaning helplessly despite wanting to kick the gloating Harvey in the balls.

Sherry pleaded, "Ed, please let me have some relief."

"Yes sweetheart, you have earned that," said Ed and came over and knelt in front of her, gazed into her eyes and began stimulating her clitoris lovingly with his fingers, while stroking her breasts gently with his left hand. Sherry was past the point of caring that her mentor was frigging her in front of everyone and writhed and moaned loudly and uncontrollably.

Ed paused every now and when Sherry looked in his eyes, she realized that Ed was not prolonging it to torment her but rather increase his own enjoyment. His eyes betrayed how much he had always adored her and how much he would miss her and how we wanted to savor this night and not want it to end. He had always fantasized having sex with his beautiful protégé but never let on. This was as close to his fantasy that he would ever get.

Much as she wanted to provide her mentor endless joy, perverted as it may be, her needs were now urgent and her moans were punctuated with "Please Ed don't stop", "God almighty please me come" and "Please, please let me come."

Ed paused briefly one last time to record the moment in his mind and proceeded to stimulate her expertly with his fingers with his hands stoking her breasts until Sherry convulsed wildly, screamed and had her richly deserved mind blowing orgasm, while Ed stared at her transfixed.

He left his finger in her pussy, while she recovered from the aftershock of the tremors, until Tammy came over and handed her some tissues. Sherry wiped herself off and stood up.

"You are still my mentor. Nothing will change that," said Tammy hugging her and the group clapped in appreciation and Sherry looked pleased and said, "Awww Tammy. That is so sweet."

Ed then knelt in front of the naked goddess and kissed her hand and said, "Now this is a night I will remember forever. You have made an old man incredibly happy," and Sherry beamed radiantly at being able to give her mentor an unforgettable gift.

*****