Sherry's Test Ch. 08

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Sherry is punished by her mentor, Ed.
2k words
4.48
54.8k
12

Part 8 of the 45 part series

Updated 06/07/2023
Created 08/26/2009
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Author's Note:

Please read this story in sequence. Comments/Feedback welcomed.

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Monday 3 PM drew near again and Sherry again walked in to the teacher's lounge. The group was waiting for her as usual, the previous Friday's session seemed to have increased their appetite for naked sherry rather than diminish it.

As Sherry stood in the middle of the room, Nancy offered to volunteer.

"Not today, Nancy dear," said Roberts. "I have something special planned for Sherry today. Sherry looked at Roberts and then Matt with trepidation.

Matt placed a hand on his heart and blew her a silent kiss as if to assure her of his love and that he would be at her side.

Roberts knocked on the adjoining Principal's office and the door opened and in walked in Ed. Ed had recently retired and he had been responsible for hiring Sherry and mentoring her through the early days. He was a benign old man, kind but was as Sherry was to discover, there is no such thing.

Sherry gasped when she saw Ed and blushed as the realization hit her that she would be humiliated and punished in front of her mentor.

"Since Ed was your mentor, he feels particularly let down by your test paper incident, Sherry. I suggested he participate in your punishment and he reluctantly agreed," said Roberts.

Sherry looked at Ed who didn't seem all that reluctant at all. 'Men!' she thought and fumed.

"Yes Sherry, since I took you under my wing and mentored you all these years, it is only fair that I participate in your punishment," said Ed smiling in an embarrassed manner. In his heart, he knew he shouldn't be part of poor Sherry's humiliation. But all her colleagues had gotten to witness her punishment. Why should he let go of an opportunity to see a beautiful girl stripped and spanked, he reasoned.

"Ed, please? I am really sorry for what I have done and already been punished quite a bit. Please don't participate in this. I will be really humiliated," said poor Sherry.

Before Ed could reply, Roberts piped in with, "Humiliation is mainly what your punishment is about, Sherry. So, Ed stays."

Sherry resigned herself to her fate.

"I am sorry, Sherry. I am an old man. I won't have too many of such pleasures. Don't deny me this?" said Ed.

Even though Ed had always played a fatherly role with Sherry, he always had secretly, guiltily and helplessly wondered what she would look like naked. And at some level Sherry also knew that Ed's interest in her wasn't purely altruistic and his attempts to guide her and mentor her were in order to enjoy her company a little more.

'I have been shamed before so many. What is one more,' she thought.

'But this is Ed! Someone I looked up to, someone who was like a father to me and now I am going to be humiliated in front of him. And what is more, looks like he is relishing the prospect,' she continued thinking ruefully.

"Ok, Sherry. I want you to slowly remove each piece of your clothing, give it to Ed and request him for your spanking after every piece is removed. Ed, I have already filled you in on the details as far as the mirror and gentle spanking is concerned," said the principal.

Sherry was wearing a dark blue suit dress with a white blouse and looked very smart and professional.

She removed her jacket and went and handed it to Ed.

"Ed, I am sorry I let you down. Will you please give me a spanking," asked Sherry, standing before Ed with her head bowed.

Ed got up and led Sherry to her punishment chair in front of the mirror. Sherry knelt on the chair and looked at Ed's face in the mirror and blushed.

"Hold up your skirt," said Ed.

Sherry held up her skirt and exposed her white panties to Ed.

Ed was about to start the spanks when he had another idea.

"Harvey, can you come over and hold Sherry's skirt up?" asked Ed.

'Oh no. Ed knows I detest Harvey and even he is going to humiliate me by making Harvey participate more than necessary,' thought poor Sherry.

Harvey came over eagerly and stood on the other side of Ed and held her skirt up.

"Now take down your panties," said Ed.

Sherry blushed when she heard that. She had hoped for a gradual disrobing allowing her to get used to her state of nudity, but Ed had other ideas.

Sherry rolled down her panties slowly as her gorgeous ass came into view. Ed had stepped back a few feet in order to admire the view.

Sherry looked at his face in the mirror and again blushed. She was exposing her ass to her mentor and soon she would be exposing much more. Her life had changed so much in three weeks.

Ed happily took in the sights of Sherry's ass. He had admired her clothed ass many times and now he was looking at her naked ass. And not only that, he would get to rub his hands on her ass and spank her.

She was made to hold up her skirt again and the fact that she was holding up her own skirt and exposing her ass to Ed as well as all her colleagues added to her embarrassment.

Like others, Ed noted with satisfaction how beautiful and vulnerable Sherry looked when she blushed.

"One, thank you, Mr. Ed," said Sherry as he started spanking her.

Sherry had always jokingly called him Mr. Ed and instinctively realized that calling him that while being spanked would be more humiliating for her.

'Damn. I am getting off on my own humiliation,' thought Sherry as the second spank landed.

"Are you enjoying being spanked by Ed, Sherry?" asked the cruel Roberts.

"No Sir. It is humiliating Sir," said Sherry.

"And you are not the slightest bit aroused?" asked Roberts.

Sherry blushed at this and knew it would be too dangerous to say, 'No.'

Ed stared at Sherry's embarrassed face and intuited her silence implied assent and raised his eyebrow in surprise.

Sherry turned another shade of red at Ed knowing that these punishments excited her at some level despite her efforts to the contrary.

"Ten, thank you, Mr. Ed," she said as her first round of spanking concluded.

"Ok. Now take off your blouse and your bra," said Ed.

Sherry again was taken by surprise. She slowly peeled off her blouse as Ed looked admiringly at her bra clad boobs. She unhooked the bra and rolled it down exposing her beautiful, firm boobs to Ed for the first time.

Ed sighed looking at his delectable protégé. Though he had fantasized about seeing her naked, never in his wildest dreams had he thought he would actually get to see it.

Roberts had described these spanking sessions in detail to him and he made Sherry hold up her skirt again, held and stroked her naked breasts with his left hand and rubbed her naked ass with his right.

Sherry maintained eye contact in the mirror and noticed Nancy looking sympathetically.

Sympathetically or wistfully, she wondered.

Harvey and Jeff looked gloatingly and Sherry blushed again at having to suffer the indignity of being punished in front of her hated colleagues.

Soon Ed finished his ten spanks and lovingly rolled up her panties. He went and sat on the couch and said, "Sherry, stand before me and take off your skirt and panties. And do it slowly and seductively."

Sherry squirmed. Was this the Ed she knew, the kind old man who was always there for her, guiding her through the school politics, cautioning her time and time again to keep her impetuousness under control? And now he wanted her to stand in front of him, topless like a cheap stripper and seductively take off her clothes.

But Ed had tasted blood and his crazed brain had taken over. Sherry was no longer hos protégé but just another sex object to be enjoyed and ogled at.

'Damn she must be awesome in bed,' thought Ed as the humiliated Sherry had to suffer the indignity of slowly stripping in front of her mentor.

Sherry swayed seductively as she took off her skirt and stood before Ed naked except for her white panties.

Ed was spellbound by her big, firm boobs, her flat stomach and long well toned legs.

Sherry inched down her panties again swaying seductively to some imaginary music and Ed wore an expression of absolute bliss as Sherry's neatly trimmed bush came into view.

She handed him her panties and Ed pocketed it.

"Hands on your head," instructed Ed. Roberts had apparently not missed any details when he had recounted these sessions to Ed.

Sherry blushed as she clasped her hands over her head and thrust her boobs out.

"I like a 360 degree view. Why don't you do slow turns?" suggested Mr. Ed.

Sherry did a few slow turns exposing her body from all angles to Ed as well as all her colleagues.

"For the next part, I would like Harvey and Jeff to come and sit on either side of me," said Ed.

Harvey and Jeff came over eagerly and sat on either side of Ed on the couch.

"Now, lay on our laps, with your butt in my lap, breast in Harvey's and legs in Jeff's," said Ed.

Sherry blushed again at this new humiliating task. Lying in their laps was at once more intimate and by the same token that much more humiliating. And Ed had to choose Harvey and Jeff for this humiliating task. Harvey stroked her naked breasts, Ed stroked her butt and Jeff pawed her long legs.

Ed asked her to lift her face up and look in the mirror. Sherry looked to see all her colleagues staring intently at his new punishment position.

'Is this really happening?' wondered poor Sherry. The whole scene seemed like a bad dream. Like a lot of people, she had had dreams of walking around in school and suddenly noticing she was naked and this seemed like a continuation of that nightmare.

Harvey and Jeff continued stroking her breasts and legs as poor Matt looked on helplessly.

Ed started spanking Sherry as she counted out the strokes while maintaining eye contact in the mirror.

When his ten spanks were over, Ed made her lie the other way around so that her boobs were now in Jeff's lap and her legs in Harvey's. Now it was Jeff's turn to grope her breasts while Harvey slid his hands up and down her long legs.

Ed completed his ten spanks and for the finale, made her stand naked in front of the white board and write "I will not leak test papers" ten times. He then made her face everyone and hold her ears and do ten sit ups apologizing with every sit up, "I will not leak test papers."

Sherry to her chagrin noticed that she was soaking wet with arousal and despite her intense humiliation, she felt intense excitement as well. She prayed that none of her colleagues noticed.

But Ed sure did, as he made her stand in front of him and beg for each piece of clothing and put it on in front of her. An embarrassed and chastened Sherry knelt before Ed and begged for each piece of clothing and put it on in front of him.

Ed kept the panties as a memento but that did not bother Sherry. All she could think of was rushing home and tearing off her clothes and being ravished by Matt.

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2 Comments
Eric_ShiftEric_Shiftabout 14 years ago
Can't belive I missed this instalment.

Very brief, would have like d a whole lot more description of things, but overall very Hot.

AnonymousAnonymousabout 14 years ago
Terrific

This whole series is wonderful. I'm going back to vote on the previous segments so I won't repeat this comment but the quality is uniformly great. The author really, truly has captured the ability to create a scenario and wring the maximum erotic impact out of the tension, the relationships, the details ... the humiliation. Of course there are plenty of leaps from reality in the story, but it presents a world that starts out looking like the real world and slowly distorts that reality until these amazing fantasy-inducing things happen, as if they were just under the surface of our interactions with teachers, students, bosses, mentors, friends, rivals. The story promotes the idea that very close to our daily lives is this possibility that everyday situations can spin into erotic dreams/nightmares. To me, that's the best an artist in this genre can do.

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