Sherrys Magical Christmas Gift
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Sherry’s Test Ch. 20 free porn video
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 it’s own.
This chapter contains light spanking and humiliation in a family environment. It does not contain any 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 any real person.
Feedback, votes and comments greatly appreciated. I put a lot of effort in writing this, so please take a moment to vote and comment.
Acknowledgement: Thanks to Janne Fleischmann for her helpful suggestions and editing help.
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After an uneventful week, it was again Friday night at the Principal’s house. The Monday and Wednesday punishments at school were becoming less frequent but Friday night continued to be a tradition.
‘He wants you blindfolded before we go in,’ said Matt, as he pulled into the Principal’s driveway.
Sherry looked terrified and excited at the same time, wondering what Principal Roberts had in store for her as her sweetheart pulled a sleek black blindfold over her eyes.
Sherry was turned on at being led through a driveway blindfolded and wondered helplessly if any of the neighbors could see her.
‘Ahhh, welcome, Sherry dear,’ said Mary, giving her a nice hug.
‘Why the blindfold, Mary?’ whispered Sherry.
Mary whispered back, saying, ‘All will be revealed soon.’
‘She has been with that bastard for too long. His sense of humor is rubbing off on her,’ fumed Sherry, as Mary led her down the stairs to the basement.
‘Stand right there,’ instructed Roberts. Sherry stood, waiting for further instructions.
Matt surveyed the room and noted the usual guests – Harvey and Nancy, Tim and Lara and one surprise visitor. He started when he saw the surprise visitor but the Roberts gestured wordlessly asking him to be silent. Clearly, suspense was going to be a key ingredient in today’s session.
‘So Sherry, why are you here?’ asked Roberts.
‘I am here because you’re an unscrupulous rogue. And you’re blackmailing me,’ said Sherry hotly.
Roberts laughed and asked, ‘Be that as it may. But why are you here?’
‘I am here to be punished,’ said Sherry, now realizing that the bastard was making her say all this for the benefit of a new entrant to the party.
That explains the blindfold. Wonder who the new member is, she wondered with trepidation and a little excitement.
‘And why do you need to be punished? Refresh our memories,’ instructed Roberts.
‘Because I had a crush on a student and leaked the questions of a test to him. The imbecile leaked the questions to all his friends. The test was compromised because half the class was privy to the questions beforehand and half wasn’t,’ confessed Sherry. A blush spread to her cheeks as the events of that day resurfaced in her mind.
‘Do you agree that you deserve to be punished for your transgression?’ asked Roberts.
‘Yes, Sir. I deserve to be punished and shamed for my mistake,’ admitted Sherry, now playing her role of the helpless but repentant victim to the hilt.
‘Good, good. I am glad you realize that shame is an important part of your chastisement. Let’s get started then. Drop your skirt,’ said Roberts.
Sherry unzipped her skirt, and, letting it drop in a clean swoop, stepped out of it.
‘Now roll down your panties and show us your pussy,’ instructed Roberts.
Sherry stood silent for a moment caught by surprise, but complied wondering who the new spectator was and if he or she had seen her pussy before. She thought she heard a gasp in the room and knew that the new member of the party was shocked, which merely served to increase her shame.
‘Now lift your blouse a little and tie it on front so that your pussy is completely exposed,’ directed Roberts. She heard a distinct gasp again.
Oh my God. I wonder who it is! wondered poor Sherry haplessly, as she tied her blouse and exposed her unobstructed pussy to the room.
‘Do you deserve to be shamed like this?’ asked Roberts.
‘Yes, Sir! I deserve whatever shameful punishment you decide to give me,’ said Sherry demurely. Sherry felt the now familiar conflicting heady mix of shame, excitement and arousal. She found these sessions incredibly humiliating and yet there was a part of her that was thrilled by it. And yet she did not want to openly admit that she enjoyed these sessions at some level. Believing that she was compelled into these situations caused far less cognitive dissonance between her image of herself as a proper lady and her enjoyment of sexual submissiveness.
‘Good. Now remove your blindfold,’ instructed = Roberts.
Oh God! thought Sherry, as she contemplated the moment of truth. On one hand she would be relieved that the suspense was over, but then there was the terror of discovering who the latest addition to her audience was.
She removed her blindfold slowly, opened her eyes and looked the sofa in front of her.
‘Mom!’ she exclaimed, and quickly crouched, covering her privates.
‘Well, Sherry. Looks like you’ve been a very naughty girl,’ admonished her mom.
‘I am so sorry, mom!’ wailed poor Sherry, embarrassed beyond belief. Nothing over the past few months had prepared her for this. And yet she was turned on by adopting the embarrassed naked female pose in public in front of her mom.
Matt, to his discredit, had grown to enjoy theses sessions as much as Roberts, especially since he knew that Sherry too was insanely turned on by them despite protestations to the contrary. He was the quintessential voyeur and enjoyed watching his beautiful fiancée stripped and spanked. He loved to see her embarrassed and even humiliated as long as she did not really mind it. And Roberts to everyone’s delight kept devising new ways of humiliating Sherry. This time however, he wasn’t sure if Roberts had gone too far. This was her own mother after all!
He was on the verge of intervening and bringing the proceedings to a swift halt, but Nancy whispered to him, ‘Oh come on Matt. You know that she knows that if she dresses up and leaves, nobody will dare stop her. If she goes through with this, then at some level she wants this experience. You know that being the hapless victim turns her on to no end,’
‘Still, I think I ought to stop this,’ said Matt.
‘Hold on a second and see if she gives you a hint that she wants you to step in,’ counseled Nancy.
‘Oh come on, Sherry. You know the rules. No covering. Now stand up straight and get your hands on your head,’ instructed Roberts.
Sherry pondered for almost a minute and then said ‘Yes, Sir!’ and stood up straight, her hands clasped behind her head.
‘See. She didn’t have to do this. She could have told him to stuff it and run out of the room,’ said Nancy and Matt looked relieved that she had decided one way or the other. He would have supported her if she had decided to quit but she hadn’t, and he was delighted. His appetite for watching his sweetheart being humiliated seemed to be insatiable.
‘Yeah you were right,’ said Matt relieved that his sweetheart at some level was consenting to this.
‘Still you should have safe word between the two of you. If ever things get out of hand, you will know if she really wants it to stop or if she is just playing her helpless victim role,’ advised Nancy and Matt nodded.
Sherry on the other hand was deeply embarrassed by having her mom see her like this. Like a lot of women, Sherry had a difficult relationship with her mom. Her mom was just 19 years older while they were close there also was competition between them. Both vied for her father’s affections and clearly there were Freudian undertones to their relationship. In many ways, she was her adversary and now s
he was humiliated before her. And again that familiar rush that accompanied such surrender.
‘Oh Sherry. This is so shameful. Standing in front of the good Principal, your fiancée, and your colleagues, naked and all that,’ said Suzy, Sherry’s mom. ‘And didn’t you tell me you hated Harvey, Nancy’s boyfriend? You’re naked in front of him!’ exclaimed Suzy, rubbing it in.
Why is my mom saying this? wondering Sherry. Oh my God! Could she be enjoying it?
‘Yes, Suzy. Shame and humiliation are a big part of Sherry’s correction. I trust you won’t be offended?’ asked Roberts.
‘Well, if my being here increases her embarrassment, then I guess it serves a purpose. Please don’t hold back on my account,’ said Sherry’s mom.
‘Thank you, Suzy. Your participation serves admirably and I must thank Nancy for making it happen,’ said Roberts. Sherry turned and glared daggers at Nancy.
Nancy merely shrugged and smiled.
‘Sherry dear, hold out your hands,’ said Roberts, walking over with a ruler in his hand.
Sherry held out her hands and waited with trepidation.
‘Doesn’t she look more like a naughty schoolgirl than a teacher, Suzy?’ asked Roberts.
‘She sure does,’ admitted her mom.
Sherry winced and said, ‘One, thank you Sir. Sherry felt like a embarrassed chastised little girl and yet her nipples were hardening and her pussy was getting moist. She felt the eyes of her audience on her and that merely served to increase her mortification and her arousal.’
After his ten hand-spanks were over, Roberts invited Suzy to come and punish her daughter with the ruler.
‘Oh God!’ thought Sherry as her mom came over and the audience moved in front of her to watch the spectacle.
‘One, thank you mom,’ said Sherry, as the first ruler hit landed. The ridiculousness of being hand-spanked with a ruler in front of her colleagues felt weird and yet strangely erotic. Reflected on her mom’s face was a smirk that said, ‘Our relationship has been changed forever. I have the upper hand now.’
‘Do you deserve this, Sherry?’ asked her mom.
‘Yes. mom. I have been a bad girl. Please punish me,’ said Sherry, getting into the act of a girl who had no choice but to accept the punishments meted out to her. Giving in to her competitive mother felt strangely liberating.
She made eye contact with her audience and noted Roberts, Mary, Nancy, Harvey, Lara, Tim and Matt all drinking in the sight of her naked from the waist down, being punished like a naughty schoolgirl by her own mother. Her blouse bunched up and her uncovered ass made her seem more like a silly girl than a grown woman.
‘Ten, thank you mom!’ exclaimed Sherry, as the tenth blow with the ruler landed.
‘Now, undress your naughty daughter completely and present her to the audience,’ instructed Roberts.
Oh my God! My own mom is going to strip me, she thought, as Suzy proceeded to slip Sherry’s blouse off. Suzy then proceeded to unclasp her daughter’s bra and remove it, leaving Sherry clad just in shame.
‘You are a beautiful woman, Sherry. But you’re still a very naughty young lady,’ her mom admonished. Sherry blushed.
‘Ladies and gentleman, I present you with my naughty, naked daughter for punishment,’ said Suzy. The audience clapped wildly. Sherry closed her eyes in extreme embarrassment.
Roberts walked over and led her by her ear to her punishment chair, which was set in front of the mirror.
‘Suzy, we are all going to take turns spanking your naughty daughter. It would be the perfect touch if you were to stand in front of her, hold her face and look into her eyes as she’s getting spanked,’ said Roberts.
Suzy thought it was weird, but shrugged and went over. She cradled and caressed Suzy’s face as directed.
Sherry blushed uncontrollably as Principal Roberts started to spank her.
‘One, thank you, Sir,’ said Sherry, blushing and looking into her mother’s eyes.
Oh my God! Mom is turned on by this and enjoying it, she thought as she said, ‘Two, thank you, Sir,’ with a slight wince.
‘Three, thank you, Sir.’ She was now getting increasingly turned on as her ass rushed out to greet the next spank and blushed, wondering if her mom realized that.
Soon his ten spanks were over. Mary gave her another ten spanks. Sherry was close to the kind, older Mary and of all her spankers, minded Mary the least. But yet, her mom caressing her face was a constant reminder that she was getting punished in front of her own mother and her shame and her arousal continued to increase.
Next was Nancy, and she rubbed it in mercilessly.
‘Sherry, how does it feel to get spanked by your best friend in front of your mother?’ she asked.
‘It feels great, Nancy. I always dreamed of this day,’ Sherry said sarcastically. The fact that Sherry relished her humiliation was an open secret, but Sherry was not going to give Nancy the satisfaction of making her whimper.
‘Ahh, your sassiness hasn’t been spanked out of you yet. What do you say we fix that, Suzy?’ Nancy asked. Suzy smiled.
‘Wait till Harvey spanks you in front of your mother. Imagine how humiliating that will be,’ warned Nancy as she teased Sherry relentlessly. But Nancy couldn’t break her even though Sherry was now squirming helplessly and even moaning a little as the images that Nancy conjured up kept floating in her head.
Next was Tim. It didn’t help that Suzy kept asking Tim inane things, like, ‘So Timothy, you’re one of Sherry’s colleagues?’
‘Yes ma’am, I am!’ said Tim, as he gave her the first spank.
‘Oh dear. How dreadfully embarrassing that must be for you, Sherry,’ said her mom, stroking her hair and again preventing Sherry from tuning everything out.
‘Yes, mom. It is dreadfully embarrassing,’ said Sherry, deliberately using her mother’s choice of words as a signal of her capitulation.
‘And he’s also your step-sister Lara’s boyfriend! Oh dear. How humiliating,’ said her mom, still stroking her hair.
‘Yes mother. It is very humiliating,’ said Sherry. But this time, there was defiant quality to her voice as a reaction to her earlier surrender.
Suzy caressed her daughter’s face ostensibly in a caring way, but it was clearly evident to everyone in the room that Suzy was turned on by her daughter’s punishment.
After Tim was done, it was Lara’s turn, and Lara also teased her.
‘So did you enjoy my boyfriend spanking you?’ asked Lara.
‘You know I did. I lie awake at night dreaming of it,’ said Sherry hotly, and the room laughed.
‘And having me spank you in front of your own mother doesn’t embarrass you?’ inquired Lara as she looked at Suzy and exchanged smiles.
‘You know it does!’ replied Sherry hotly, her mind in the grip of conflicting emotions again. She felt angry that her step-sister was spanking her in front of her mom, yet felt helpless to do anything about it and there was that inexplicable rush from her surrender and the worshipping eyes of her audience.
‘If only Daddy were here to see this,’ sighed Lara, and Sherry looked mortified at the thought of her Dad seeing her spanked like that. And yet there was a distinct tingling in her pussy and her nipples hardened even more as her cheeks reddened.
‘What would he think of his darling daughter?’ teased Lara as she laid her last spank.
And what indeed would he think of her, she wondered with trepidation but not without a strange excitement coursing through her body as she shuddered at the prospect.
Next was Harvey.
‘So Sherry, here we are again. How does it feel to be humiliated by your hated rival?’ asked Harvey. Sherry had always hated the smug Harvey even before the eventful day of the leaked test and of all the humiliations she had encountered, being stripped and shamed in front of and by Harvey was among the worst and yet it was also accompanied by intense arousal. Still, she was determined to not hand
him victory in a platter.
‘Annoying,’ said Sherry dismissively, determined not to be broken by the despicable Harvey.
‘Oh Sherry. It must be more than just annoying. I remember you going on and on about how you hated him and how you wished Nancy would throw him out on his ass,’ said Suzy, much to Harvey’s delight and Sherry’s embarrassment.
Sherry fumed and squirmed at her mom’s unwanted interjection and yet bowed her head in submission.
‘Yes, Sherry. It must be more than just ‘oh so annoying.’ Your ass is the one getting it now,’ mocked Harvey as he landed his third spank and Sherry wished the roles were reversed and she was the one spanking his smirk off his face.
‘Three, thank you, Sir, may I please have another,’ said Sherry angrily.
‘Ouch, four, thank you, Sir,’ said Sherry, as Harvey couldn’t help but spank her a little harder.
But no matter what Harvey tried, he couldn’t break her. Even though Sherry was in a constant state of embarrassment at having to suffer the ignominy of being spanked in the nude by her hated rival while her own mother dearest held her face and goaded him on, she held strong.
Why is she so mean to me? wondered poor Sherry, gazing into her mother’s eyes. And then it hit her, Oh my God! She’s turned on by this. Maybe she’d like to be on the receiving side herself!
Finally it was Matt’s turn.
Oh my God! My fiancé is going to spank me while my mom cradles my face. This is so surreal. This cannot be happening! she thought.
Matt decided to just get on with the spanks without much fanfare, but Sherry’s mom wouldn’t give her a break. She was relentless in her teasing. Clearly Suzy was enjoying her new found superiority and wanted to cement it to change their relationship irrevocably. And while Sherry hated giving in to her mother, there was a sense of relief that she would not have to compete so much with her and also the strange arousal resulting from her subjugation.
‘Oh my God! Your sweetheart has been watching you be humiliated by your colleagues all along. How dreadful,’ she said at the first spank.
‘You do need a man to take you in hand. I am glad you found one,’ said her mom, stroking her hair at the second spank and gazing at Sherry’s face. She took in every nuance of Sherry’s expressions – embarrassment, shame, defiance, and, most amazingly, arousal.
‘Three, thank you, sweetheart,’ said Sherry as the third spank landed. She had chosen to say sweetheart instead of Sir to underscore the fact that it was her sweetheart who was spanking her and increase her own humiliation. Her ass swayed in between spanks and rushed out to meet each spank. The spanks were soft and didn’t hurt but she could still feel a little sting and winced.
‘I can imagine your wedding. Everyone will be waiting for the bride to walk down the aisle, but the bride will be busy getting her butt tanned by the Principal,’ teased Suzy.
‘Seven, thank you, Sweetheart. It feels so good to have you spank me in front of my mother,’ said Sherry.
Sherry’s signs of arousal were now clear as she squirmed, moaned and wiggled her ass. The sensory overload of having everyone spank her naked butt while her dear mother watched had taken its toll. Plus, her mother’s constant commentary had prevented her from blanking out her predicament and compelled her to continuously acknowledge it.
Matt smiled as he realized what was happening, and Suzy caught on and teased, ‘My dear daughter! Don’t tell me that being punished so humiliatingly has turned you on?’
‘Of course not!’ Sherry denied hotly, not wanting to admit it openly. It was a game she had played before and it served to maintain the lie that she was just a helpless damsel in distress.
‘We’ll see about that shortly,’ Nancy warned, and Sherry shuddered at the thought of being naked and hopelessly aroused in front of her mother.
‘Ten, thank you, sweetheart,’ said Sherry with relief, as Matt finished his spanking.
‘Now it’s time for the mother to do the honors,’ pronounced the Principal. Her mom came over behind her and stood ominously.
Sherry knew this moment was inevitable and yet she shuddered at the prospect. She was ashamed and yet there was this feeling of relief. She had always competed with her mom ever since she was fifteen and it was tiresome. Now she was a little child again waiting for her punishment from her mother. Her mom held the upper hand and Sherry did not mind that. She was strangely turned on.
Haven
- 01.06.2022
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