Sherry's Test Ch. 33

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Her Highschool Rival.
5.8k words
4.55
23.1k
8

Part 35 of the 45 part series

Updated 06/07/2023
Created 08/26/2009
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This chapter contains light spanking and plenty of 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.

*****

Matt asked me to write this episode, so here goes.

The punishments in the teacher's lounge had become infrequent. They had clearly run out of ideas and for the most part I had to merely do my work in the nude while my colleagues occasionally ogled me. Harvey, more than others but that was to be expected.

So I entered the room and commenced working on my prep work for the next week's classes. The normal process is that I wait until the Principal comes into the rooms and tells me to strip. Sometimes, he does not even bother to do that and I am left mercifully alone to focus on my work.

Today, he entered with an attractive woman along with him. She seemed my age and looked vaguely familiar.

Slowly, realization dawned. OMG, it was Claire, my high school rival! Then a feeling of dread sunk in. Oh God, they were going to humiliate me in front of her!

I felt defiant. I had put myself through enough. I did not want to go through with this.

"Sherry, do you remember, Claire?" asked Roberts with a devious smile.

"Yes, I do. Claire, sweetheart, how have you been and what brings you here?" I asked her nonchalantly as I rose to shake her hand.

Claire was surprised at my cordiality more so because I was sure the Principal had told her about my impending humiliation.

She shook my hand as the Principal continued, "Claire is here to apply for the accounting position we have open. She spotted you walking across the grounds and mentioned that she would be reluctant to work here since the two of you were rivals in school."

I shrugged and could not help feeling superior because, I had bested her in everything at school - popularity contests, sports, homecoming queen and even grades.

"She told me that she has not forgiven you for stealing her boyfriend in school," continued the rascal.

"I did not!" I protested.

"Did too!" said Claire, and I felt we had regressed to being silly schoolgirls again.

"Well one day, Harry was going out with me and next day I spot him having dinner with you. Most would call that stealing," said Claire angrily.

I was bewildered. Did the Principal really want to hire someone as juvenile as this? But then again, he was pretty juvenile himself and that too a deeply perverted one at that.

I could sense the direction, this was going. Roberts was trying to inject some drama into the proceedings in order to make my capitulation that much more enjoyable. The audience was spellbound. Clearly, drama agreed with them.

"Claire, honestly, Harry told me had broken up with you. I had no idea!" I said. It was true.

"Yeah but you could have checked with me," said Claire admonishing,

I could not deny that. She was right. I should have. But then I was young. And the prospect of a good looking guy like Harry dumping Claire and asking me out had proved to be too heady. It didn't last long. He was boring and I dumped him after a couple of weeks. Did not even sleep with him. But Claire was right.

I should have apologized but my initial defiance of not wanting to go through with my punishment was wearing down. There was a part of me looking forward to being humiliated by my rival in front of my colleagues. OMG what had I become, that I was turned on by this? Perversely, if I had been determined to stand my ground and refuse to be punished in front of Claire, I would have merely apologized and then been steadfast in my refusal.

But I was turned on. I was crazed.

"Well in any case, he had better taste," I said deliberately, to rile her up.

Claire's eyes flashed in anger and if looks could have killed, I would have been burnt to ashes on the spot.

"I accept your deal," said Claire shaking the Principal's hand.

"What deal?" I wondered, but knew I would find out in due course.

"Sherry, you owe Claire an apology," said Roberts.

"I am sorry, Claire. I was out of line," I said, knowing fully that it would not suffice. Yet doubts of going through with this re-surfaced. I had been through all kinds of humiliations the past few months. But this was new. But then again, new was good. New was exciting.

I looked at Matt inquiringly and he nodded in excitement.

Roberts noticed the exchange of glances and intuited that I was game.

"Come now, Sherry. Make it more sincere," said Roberts and he gestured to the carpet with his eyes.

"Oh God. Here it starts," I thought and felt my pussy get moist.

I knelt before the wide-eyed Claire and said earnestly, "Claire, you were right. I should have checked with you. Please forgive me."

"I don't know Sherry. I was really fond of Harry and it broke my heart," said Claire, who seemed in no mood to forgive.

"Please punish me as you see fit, but forgive me at the end. Please?" I asked sincerely, now slipping into my role.

"Claire is a novice at this so let me help her out. Sherry, ask her to strip you naked," said Roberts.

Claire looked stunned. As did I. I had expected the proceedings to be more gradual.

"Claire, please strip me naked," I said still kneeling, but rose after making my request.

"Oh Sherry, I am so going to enjoy this!" said Claire as she turned me around and unzipped my skirt.

Interested members of the audience, pun intended, re-positioned themselves to get a better view.

"What is it with men?" I wondered. "They have seen me naked so many times and yet are wildly excited at the prospect of me being slowly stripped by someone different in a new situation."

But truth be told, I was excited by the newness of this situation too.

"Face her in front of the mirror. Let her see her colleagues enjoying her denuding," said Roberts.

Claire looked around and led me to stand in front of the dreaded mirror and slowly caressed the side of my face establishing her power over me.

"I am so going to enjoy this," she gloated.

I was going to enjoy it too, but yet I was embarrassed and blushed.

The audience as usual loved it. They and especially Matt, loved to see me embarrassed and blushing.

My white blouse still covered my panties but not for too long, as Claire stood my side and slowly started unbuttoning my blouse and caressing my body as she did that. The caressing was meant to indicate her power over me and perversely, giving in to such power excited me.

Soon I was standing in front of the mirror in my cream colored bra and panties.

Claire caressed my bra clad boobs and asked, "Are you sorry you stole my boyfriend?"

"I can't help it if he dumped you," I heard myself saying. I knew my sub-conscious had tripped me up .My sub-conscious clearly wanted to rile her up further to make my capitulation that much more humiliating and perversely erotic.

"In that case, I am so going to enjoy stripping and spanking you in front of your colleagues," she gloated.

As she proceeded to unhook my bra, I noticed Matt smiling and shaking his head. He knew of my predilection for riling up rivals in order to make the inevitable capitulation that much more intense.

Soon I was standing in only my panties in front of the mirror and the audience looked mesmerized. Even some of the women were looking on with rapt attention, Some, like Nancy and Lara were clearly wishing they were in my place.

Claire pinched my nipples and said, "This is what happens to shameless sluts who steal boyfriends."

It fell flat on the audience because it just did not have that zing.

Roberts intuited that and said, "Get her to beg you to take off her panties."

Claire looked excited and repeated the command.

"Claire, my high-school rival, please take off my panties and expose me to my colleagues," I asked earnestly, twisting the knife into my own humiliation by adding in the rival part.

Claire clapped her hands, swatted me on my butt, knelt behind me and slowly proceeded to peel down my panties.

She smiled at seeing my shaved pussy and said, "So the sweet, innocent looking homecoming queen is a shameless slut after all" and I looked angrily at her.

"Leave it resting in the middle of her thighs," said the Principal and Claire did so. I had to spread my legs a little to keep the panties in place and it offered the audience a view of my insides from behind. I blushed at the thought of how slutty that must look.

I deliberately made eye contact with Harvey and noted his sneering look. God I wanted to smack it out of him but my helpless rage merely served to increase my arousal.

"What is it that I find alluring about being humiliated in front of my rivals," I wondered again. "Was it that it dissipated the pressure of competition?"

Matt looked completely besotted with me and I was happy about that. It did wonders for our love making and turned it from very good to absolutely mind blowing. Tonight, I could expect multiple orgasms well into the night.

"Now stand in front of her and give her some hand spanks," said Roberts as he proceeded to demonstrate a couple before handing her the ruler and adding, "Remember, the idea is humiliation and not pain. So, be gentle and take your time to let her feel the embarrassment fully."

Claire stood in front of me to the side so as not to block the view in the mirror and proceeded to spank my hand.

She was a quick study for she spanked with just the right amount of force to get me to wince a little but not so much that it hurt. She waited and looked me in the eye and let the humiliation sink in.

After about ten on each hand, the Principal nodded to indicate that it was enough.

"Now let's have you turn around and jog in place," he continued.

He was making me feel like a schoolgirl in front of my high school rival, the realization dawned. I couldn't help but marvel at his acumen, demented though it was.

I turned around and jogged in place, keeping my legs apart just a little in order to prevent the panties from falling down.

Claire and the audience looked delighted as I continued for a couple of minutes.

"Rotate as you do this," said the Principal and I did so. After a few rounds, the Principal had me do jumping jacks and other gymnastics.

Claire clapped through it all like an excited schoolgirl and the audience enjoyed watching me do these demeaning exercises in front of her.

"Now take your panties all the way off and give it to Claire," said Roberts.

I did so and knelt in front of Claire and handed her my panties. I was not told to kneel, but thought it was appropriate.

"Now the apology squats," commanded the Principal.

I remembered the first time I had to do it in front of Harvey, my current rival. Would it be as humiliating to do it in front of Claire? It would be, I realized as I felt myself turn wetter.

I looked as contrite as I could and commenced my squats saying, "I am sorry I stole your boyfriend."

The angle, Roberts had positioned us, ensured that all my frontal charms were visible in the mirror while they had a direct view of my ass.

I blushed profusely as I had to perform this demeaning task in front of the gloating Claire. And as usual, my I felt myself getting wetter.

"I blushed and my pussy gushed," I thought incongruously and almost giggled. I guess it was just nervous excitement but I couldn't help imagining standing in front of my class and teaching, "The degree of gushing of the pussy is directly proportional to the degree of blushing in the face. Or to take it further, the degree of the gushing of the pussy is proportional to the degree of blushing times the members in the audience."

I suppressed my giggles at my wildly incongruent thoughts, continued to look contrite and repentant as I continued my squats. I did them slowly and deliberately, pausing while squatting with my legs spread, letting the humiliation sink in.

I ended up kneeling in front of Claire until I was asked to stand.

"Now feel her pussy to see how wet she is," said Roberts.

Claire looked wide-eyed and I looked petrified.

I blushed uncontrollably as Claire looked me in the eye and slowly inserted her index finger in my sopping pussy.

"It is soaking wet," she pronounced before adding, "You are such a shameless slut!"

I blushed furiously and Robert must have gestured to her, for Claire pried open my mouth with her other hand and stuck her drenched finger in my mouth. Without being told, I licked my juices off her finger as Claire looked delighted. The audience stared in rapt attention. There's something absolutely delectable in a girl getting her comeuppance and my pussy gushed in agreement as my nipples hardened further.

"Now it's time for fetch. Throw her panties around the room for her to fetch," said Roberts and Claire looked gobsmacked. My arousal, I am ashamed to say, only increased further at this humiliating prospect.

"Will this also be part of the deal, Sir?" asked Claire and the Principal nodded.

"What deal?" I wondered as Claire opened her handbag and extricated my panties from it.

She bit her lip and contemplated and then shrugged and tossed the panties after balling it up.

I crawled on all fours, slowly and sensuously, swaying my hips, letting my audience soak in the sights of my bobbing breasts and swaying ass. I kept my face level so as to make eye contact with whoever I passed.

"If I was in for the humiliation, I might as well get the max out of it," was my twisted thought process.

I passed a sneering Harvey and an admonishing Nancy as I crawled over to my soiled panties lying on the carpet and picked it up with my teeth and proceeded to crawl back to Claire with the panties dangling in my mouth.

Claire clapped through it all like a silly, excited schoolgirl as I crawled back to her, knelt before her and raised my face demurely to hand her the panties. Claire instinctively patted my head and said, "Good doggie" and balled it up to throw it again.

I writhed helplessly under the intense erotic humiliation as I crawled again, this time passing Tim and Lara.

"Oh wish, Dad could see you now, sister dear," teased Lara and I shot daggers at her. Yet, I knew deep down that it would not be entirely unwelcome.

"What is wrong with me and why do these situations turn me on so much" I pondered as I continued with my humiliating crawl petrified that I would be dripping all over the carpet.

"Someday, I need to talk to a therapist about my childhood spanking. But for now, I am enjoying this way too much," I mused as I crawled back with my panties in my mouth, now wildly excited and writhing and swaying uncontrollably.

It is always fun when I get to the point where my arousal exceeds my self consciousness. I then start enjoying the session with increased abandonment and the reduction in self consciousness is simply exhilarating. If I had started the session with such abandon, neither I nor my audience would enjoy it to the extent we did and nor would it lead to mind-blowing sex with Matt afterwards. My initial shyness, reluctance and progression through stages of blushing to the point of abandon and capitulation was what entranced the audience and got my pussy to sing its praises to high heavens. The fact that my blushing and embarrassment continued beyond this point merely served to increase the erotic tension of the situation and make it that much more enjoyable. Uncontrollably so, I thought. Some day I would need to deal with this addiction, but that would have to wait.

Now, let me assure you that I wasn't thinking all this while I was crawling back to Claire. I am adding this while writing about it, sitting on my bed naked as Matt is fondling my breasts and kissing the nape of my neck relentlessly while peering at what I am writing. I can feel his erect, wet dick rubbing my back and I am glad to have that prolonged effect on him, pun intended. We already had one round of mind-blowing sex after coming home and will most likely have one more round after I am done writing.

No, dear readers, while crawling around naked, all I could feel was intense feelings of humiliation and the accompanying uncontrollable arousal with my face burning with shame as I made my way back to my hated rival in school. A rival I had bested at everything, at every occasion. Until now.

Claire clearly enjoyed having me crawl for she balled it up again and this time threw it so that it landed in Harvey's lap. I learnt later that Roberts had told her that Matt was my fiancee, Harvey was my current rival and Lara was my step-sister and suggested she throw my panties over to them so that I would have to suffer the ignominy of picking up my panties from their laps.

So I crawled over to the despicable Harvey, writhing in shame and looked pleadingly into his hateful eyes as he dangled my panties. I had to grab hold of it with my mouth and the bastard predictably kept pulling it out of my reach. There are few things as demeaning as to be made to jump like this naked in front of your enemy and that too in public and I felt like a silly dog. Harvey smirked and sneered and gloated as I made my futile attempts. I bristled with helpless rage.

"Beg like a dog," commanded the bastard.

I sniffed, held back a tear, knelt before the cruel bastard, leaned forward, curled up my hands and said, "Harvey, my hated enemy, will you please take mercy on me and hand me my panties?"

Harvey looked pleased but did not relent and said, "Dogs don't speak. Bark out your request."

Oh this was so demeaning and my traitor of a pussy gushed even more at this new debasement.

"Woof" I said pleadingly.

"One for every word in the previous sentence," said the rotten bastard.

Yet, I felt defiantly proud, spread my legs a little so that he could see my pussy, held my wrists down as before, looked him straight in his eyes and said, "Woof, woof woof woof, woof woof woof woof woof woof woof woof woof woof woof woof."

I even varied the tones of the woofs and the audience was delighted. They clapped and cheered loudly and a large part of that was an appreciation for my being such a good sport, I suspect. Moreover, in doing so, I had robbed Harvey of his superiority.

Harvey, knew he was beaten and put the panties in his lap, so that he could feel what my mouth close to his dick. It was always a sore point with him that no matter what, he would never get to have me. I took great satisfaction in rubbing that in.

"That is as close as you are going to have my mouth near your dick, you pathetic loser," I said as I picked up my panties and the audience was stunned at my intrepid rebuke.

Matt clapped and the rest joined in except Nancy and Claire. It was bizarre to see Harvey look humiliated despite me being naked and on all fours in front of him.

Claire again patted my head and stroked my face as I knelt in front of her with my panties in my mouth. Again, she did this not to display affection but rather to demonstrate her control over me.

She then balled up my panties and threw it over to Matt. I crawled over to my fiancee and looked at his face with a mix of arousal and deep embarrassment. Despite all the different situations I had been in, it was always embarrassing to come to terms with the fact that he was watching and enjoying my public spectacle and more embarrassingly, I was enjoying it too. But Matt, despite his deeply perverted sexuality, was nothing if not gallant.

"Sherry, I love you so much!" he said as he stood up, raised me up and kissed me passionately for two whole minutes.

The audience loved it and clapped and cheered wildly as I glowed happily and yet blushing.

12