Sherry's Test

Matt nodded understanding the situation and somewhat relieved that Roberts did seem to be intent on keeping his promises.

"I think you can use a hug before we start" said Matt and went and hugged Sherry fondly. Some rolled their eyes and some looked as if they were sickened by Matt's unabashed romanticism and some wished they had someone as devoted as Matt.

"Ok. We have about twenty minutes left so let's get started. Sherry, I want you to go to the corner, face us with your hands clasped on top of your head and tell us what happened. Why did you leak the questions?" said the Principal in a stern headmaster voice.

Sherry walked to the corner and put her hands on the head ashamed at having to face her colleagues in this fashion and burning with the knowledge that this was only the beginning. It was going to get progressively worse and carry on for three months!! Three months! Oh why had she agreed?

Coming back to the present, she looked at her audience and said "I really don't know what came over me and I am guilty of very bad judgment. There is this jock called Sam and he came to me before the test asking for some extra coaching. The more I tried to coach him, the more I realized how hopeless he was. I looked at his chiseled face and his blue eyes and I melted. The practice questions I started giving him started to resemble the actual questions more and more and I swear it happened at a sub-conscious level. I started giving him hints like 'this is important' or 'you may want to note this down'. How was I to know he would go and tell others about it?"

"Ok. That sounds like a satisfactory explanation but does not absolve you of your guilt in any way. Let's see if we get Sam involved in proceedings at some point" said Roberts and Sherry looked horrified at the prospect. Before she could plead, the Principal continued "What I would like you to do now is go and kneel before everyone in this room, one by one, hold their hand, look up at their face and invite them to participate in your punishment. Everyone, please stand in a line. Sherry, crawl to the start of the line. Matt I want you to be at the head of the line".

Everyone scrambled hurriedly. It felt bizarre to be crawling around the room in her formal suit dress but again Sherry couldn't help but detect a tinge of excitement. Everyone's eyes burned through her enjoying the sight of this sassy girl crawling through the room. The anticipation and suspense of what was to come was also driving everyone crazy and led to pin-drop silence.

Sherry crawled to Matt, straightened herself to a kneeling position, took his warm hand in her hand and said "Will you please participate in my punishment?"

"Good. I want you to refer to everyone by name though" said Roberts before Matt could say anything.

"Will you please participate in my punishment, Matt?" Sherry asked again.

"I hate to but I will" said Matt.

Sherry blushed and moved on to the next. Next was Harvey, a puny southern guy who had always felt threatened by Sherry's looks and persona and was always trying to show her up. Harvey could hardly contain his excitement at the prospect of humiliating Sherry not once, not twice, but for countless times for three whole months.

"Will you please participate in my punishment, Harvey?" Sherry asked with dread.

"Beg me again in a more pleading tone. Put some zip in it" said Harvey sadistically.

Sherry sniffed and pleaded "Will you pleeeeease participate in my punishment, asshole?" She hadn't meant to say asshole but it came out. Everyone guffawed. Harvey angrily said "You have one more chance to ask properly. Try it again this time hold your ear lobes like a naughty schoolgirl while you ask.

Sherry held her earlobes crossing her hand and looked so alluring in her naughty schoolgirl pose.

"Will you pleaaaase participate in my punishment, Harvey, kind sir" she asked making up for her asshole comment.

"I will be more than happy to" gloated Harvey.

Next she moved to Nancy, her close friend and repeated her request as instructed.

"Oh Sherry sweetheart, I am soooo sorry this is happening to you. Yes I will be here and along with Matt, try to keep things under control" said Nancy.

Sherry looked at her gratefully and moved on.

Next was George, the inscrutable silent kind. He never said too much. George looked at her impassively and mumbled he would. You might as well have asked him he would like a cup of coffee.

Next was Kathy who hated her guts. And Kathy said she would be delighted to.

And then there was Jeff, another creepy guy and Harvey's sidekick. He said he would be glad to assist.

And there was Dana the new kid on the block and she looked flustered unsure of how to act but unable to hide her excitement.

And then there was Mike the bore. And Ernie, the all conquering playboy who had tried to conquer Sherry but had failed. He was literally jumping up and down in juvenile excitement. And then Stan, a playboy wanna be and Ernie's competitor for the ladies' attention or more appropriately their panties.

And Wayne the fat slob who looked a bit like Pavarotti. And Dave, the quintessential curmudgeon.

And Lisa. Lisa was sympathetic but still seemed excited by the unfolding of events. And Tim, another guy who looked forward to the punishments with juvenile excitement. Tim wanted to know if he could invite his friends and Roberts said "No. At least not yet".

And then lastly there was Roberts who said "Yes I have been dreaming of this all weekend. So let's get started, Ten minutes to go before the bell".

"What I want you to do is, bend over the table, put your arms straight in front of you, keep your chin up and look in the mirror. I need you to be looking in the mirror at all times so that we can admire your expression while you get spanked" he continued.

Sherry braced herself for the inevitable and did as directed. Everyone lined up behind her so that look at her from behind as well as her expression in the mirror. It was slowly becoming clear that this was not first time Roberts had done this and he had the art of spanking down to a science. And Matt, bless his heart, managed to find a small cushion for Sherry to rest her chin on.

Roberts stepped behind Sherry, smoothed her skirt and laid the first gentle spank.

"What I want you to do, Sherry, is count each one. One, thank you, Sir. Two, thank you Sir and so on" he instructed.

"One thank you, Sir" said Sherry as the next spank landed.

"You forgot to keep the eye contact with the mirror. I want you to watching in the mirror so that we can see your expression as you are getting spanked and you can see our expressions as we are enjoying watching you get spanked. Let's start again".

"One thank you, Sir" said Sherry again, this time looking in the mirror at the point of impact. It was a gentle spank but Sherry couldn't help a small wince which made her look even more beautiful and vulnerable. Everyone looked on with rapt attention and Sherry blushed at having to look at her all her colleagues in the mirror and wondering how it must look to have her butt sticking up in the air in front of them.

When she got to 10, Roberts paused and asked "So how does it feel to be spanked in front of all your colleagues, your principal and your future boyfriend, Sherry?"

"Geez what are you now, a therapist? Of course it is humiliating, Sirrrrr" said Sherry visibly annoyed at the obvious question.

"Good we are making process. And in time, I assure you, you will lose all tendencies to make smart-ass comments like this and be much more coy and ladylike" said Roberts his old-fashioned and outdated views on women coming though.

Sherry ofcourse felt like kicking herself for provoking him but it wasn't easy transforming from a confident, spirited woman to the cowering, submissive girl that Roberts wanted her to be. But she had no doubt that in time, the transformation would be complete at least during these sessions. Her audience meanwhile were wondering when she would be made to lose some of her clothes but at the same time were enjoying the suspense and the anticipation.

"OK Sherry" continued the Principal. "Time to lose your skirt. Despite your acting like an uppity bitch, the fact that you plan on being Matt's girlfriend here makes me have a soft corner for you. So, rather than make you face the humiliation of taking off your skirt yourself, I want you to go to Matt and request him to take your skirt off you. Matt, my boy, I wish your first time undressing Sherry could have been in the privacy of your own bedroom but unfortunately Sherry never had the sense to go out with you earlier. Her current predicament would have been avoided if she had done that. Anyway, what I want you to do is go behind Sherry and take her skirt off slowly so that we can watch her long stockinged legs getting exposed in the mirror".

Sherry stepped back from the table and Matt walked behind her. Shery looked at Matt in the mirror and blushingly asked him "Matt, will you please take off my skirt?"

Matt nodded sadly and knelt behind her and slowly caressed her skirt to find the zipper and pulled it down slowly. Her blouse under her suit jacket was long enough to cover her butt it was still embarrassing to be in this position of undress before all the teachers. She looked at her colleagues expressions in the mirror and they ranged from drooling from the men to smug satisfaction from some of the women.

Sherry was made to resume her position again and Roberts spanked her again ten times while she retained eye contact with her colleagues in the mirror. This time the spanks were a wee bit harder and she did not have the protection of her skirt and her wince and her vulnerability increased a bit.

"Ok that is it for now. It is time for the classes to start. I would request the other teachers to cover Sherry's classes in the morning since there is some legal paperwork that I need Sherry to sign so that we don't get into any legal issues later on. We will meet here again at 3 PM to continue with the session. Which means you will have to complete grading your papers and preparing your test questions in your own time but I trust that is a small sacrifice for the pleasure of participating in these sessions. Sherry, please go and wait in my office for the lawyers to come. Nancy, I need you as the witness, so please go and wait with Sherry" said Roberts.

Sherry stood up and proceeded towards her skirt. Roberts stopped her and said "That won't be necessary, Sherry. Leave the skirt here. I want you to feel the additional humiliation of being in this partial state of undress in front the lawyers".

"Bastard" muttered Sherry as she walked into the Principal's office with Nancy gently leading her by her arm.

The lawyers came over and unabashedly enjoyed the view Sherry offered. She was made to kneel in front of them and stand and twirl for their pleasure. All under the pretext of demonstrating that she was doing it on her own volition and there was no coercion. And the session as being videotaped for proof.

After all the papers were finalized and all her statements were recorded on video and her signature recorded with Nancy as the witness, the lawyers, Mark and Brad left reluctantly.

"Are you sure you do not want us present at these sessions as legal counsel?" Mark asked hopefully before leaving.

"Maybe later. Maybe later" consoled Roberts a he walked them out of the room.

"Well, Sherry" Roberts said. "I can understand if you are not in a frame of mind to teach your classes today. I can have someone fill in for you if you would like to continue to stay here and prepare yourself mentally for the rest of your session".

Sherry was surprised at his being considerate and realized that he was not the monster she would like to believe he was. He was just another male who could not help but take advantage of her situation.

She gratefully accepted his offer and went and sat at the corner table. Roberts went and brought her some reading materials which turned out to be spanking stories of different sorts. Sherry began to read. If nothing else, it would give her an insight into Roberts' mind and give her clues of things to come. His secretary came in a few times and made fun of the naughty girl.

At 2:45, Roberts asked Sherry to go back to the conference room and kneel in the corner facing the door. As people would come in they would be greeted by the sight of her kneeling demurely in the corner. "Greet them as they come in" instructed Roberts.

"Welcome back, Harvey" she hated to hear herself saying. "Welcome back, Jeff" she told the sidekick closely following Harvey as was to be expected. "Nice to see you again, Lisa" and so on until the group had assembled again.

"Ok. Sherry, assume the position again" said Roberts using an oft-repeated stereotype.

Sherry went back to the table. Before Roberts could say anything she said, anticipating Roberts' next command, "Matt, will you please come over and remove my jacket".

Both Matt and Roberts looked surprised, but Roberts was looking a little pleased.

Matt went over and stood behind Sherry again, slowly unbuttoning her jacket and peeling it off her. Her white blouse showed traces of her lacy bra underneath and her perky breasts seemed to be at full attention. 'Surely she is not getting turned on by all this' wondered Matt.

Sherry assumed the position again and Roberts proceeded to administer the next ten spanks with Sherry going through the embarrassment of counting while looking in the mirror at the gloating faces of her colleagues.

"Ok Sherry. You seem to be catching on. I am getting a little predictable for now but suffice to say there will be plenty of other opportunities for variation. For now, I will stick with the 'unveiling by Matt' routine" said the principal.

Matt came over and stood behind her again as she straightened from the table and stepped back a few paces to provide her colleagues with an unobstructed view in the mirror. 'Oh my God! I am going to be standing in front of all my colleagues in just my bra and panties' she pondered remorsefully.

"Will you please take off my blouse, Matt?" she asked. Matt put his hands on her blouse from behind her and bent down slightly to gently kiss the nape of her neck and whisper in her ear "I love you and you are beautiful". Sherry brightened at this and wished she could have turned around and kissed him passionately but did not want to do so in front of all her colleague. At least some things should be done in private she pondered at the incongruity of being naked in front of him before getting a chance to kiss him. 'Oh what the hell she thought' and turned around and kissed him on his lips. Nancy clapped at this and the rest of them waited patiently for it to end so that they could carry on with their fun.

"Will you please take of my blouse and expose me to the world" said Sherry now beginning to revel a little in her humiliation.

Matt again slowly unbuttoned her blouse enjoying the feel of his hand on her breast. He separated the blouse in the middle and paused to admire the view of her bra and her cleavage before slowly peeling the blouse off her arms. Her 36 D breasts would prove to be a good mouthful he thought as his gaze wandered over her flat stomach and her panties with the outline of her puffy lips showing through them.

'Oh my God' thought Sherry as she looked at the sight of her standing in her white lacy bra and panties in front of all her colleagues who stared unabashedly at her. This was far better than any strip joint they had ever been to.

At this point, Penny the secretary walked in and looked at her and smiled. "Is there a reason I should not be a part of this, Sir?" she asked Roberts.

"Part as in, you want to be spanked too?" Roberts asked jokingly.

"No!" said Penny shocked though the thought obviously excited her. "No, Sir. I meant as part of the audience".

"Sure. I don't see why not" said the Principal.

"Would you like to invite the mailman too?" seethed Sherry.

"Temper, temper" said Roberts. "And I thought we were making good progress in improving your disposition. We will get there eventually though. I promise. For now, I want you to crawl over to Penny and kneel before her and beg her to stay and witness your punishment".

Matt was shaking his head at Sherry's propensity to run off her mouth and get herself into trouble. Sherry hesitated and when she saw Roberts was serious, crawled on all fours to Penny, knelt before the black secretary and begged her to stay and participate in her punishment. She then crawled back to the table and resumed her position.

"Hold on" said the Principal. "We need to be able to watch your bra clad breasts while you are getting spanked".

He pulled up a high back chair and turned it with its back towards the mirror so that Sherry could kneel on it and lean over the back and have her bra clad breasts show in the mirror. She looked very alluring kneeling on the chair with her fake pearl necklace accentuating her bra. And her perfect round pantied bottom sticking out slightly seemed to be inviting something other than a spanking. All said and done and irresistibly vulnerable, demure look and who would have every thought looking at Sherry in her suit and sassy demeanour, that she would be reduced to this. This, was comeuppance at its best and richest.

The Principal gleefully went about the task of administering ten more spanks. "Jut out your breasts a little more, sweetheart" he instructed her like a director instructing an actress and Sherry reluctantly and poutily complied, not realizing that her pouting was adding to the charm of her spanking and making her infinitely more spankable.

At the end of it, he stepped back and called Matt over."It's your turn Matt. I dare say you will need to keep up with these sessions in your private life to keep her in line and this is as good a chance as any to practice".

Sherry blushed at this and so did Matt. "Thank you, Sir. But I would rather not" he said righteously.

"Matt, my son, you don't understand. Either you spank her or she faces the ignominy of being spanked her arch enemy, Harvey. Harvey, my son, you will get your chance before the summer is over but I am trying to break her in gently" explained the kind Mr. Roberts.

Matt walked over reluctantly behind Sherry and affectionately stroked her blonde hair."I am sorry sweetheart" he said as he gently began spanking. Sherry blushed at the ignominy of being spanked by her new boyfriend but was grateful it wasn't Harvey, at least for now she seemed safe from him.

"One thank you, Sir" she said looking into Matt's kind eyes in the mirror. If it was just kindness she would have been disappointed. But she did noticed signs of pure lust in his gaze. Glad to know he is capable of being horny mused Sherry and not just a boring nice guy.

"Matt, let me give you some lessons in intimate spanking that will stand you in good stead later" said Roberts. "You want to stand slightly to her side and cup her breasts in one hand. With your other hand, you caress her ass gently and then raise your hand and spank her while maintaining eye contact with her in the mirror. You may kiss her neck in between. Variation is the key though. Don't do the same things over and over mechanically and predictably. Vary the speed, intensity and location of the spanking. Ask her to wiggle her ass occasionally. At times, you can ask her to hold her ear-lobes with her arms crossed in front of her. That will make her look alluringly like a naughty schoolgirl. Anyway, you don't have to do all this at once. We will have plenty of other occasions to try out plenty of humiliating variations."

Matt did implement some of Roberts' suggestions. The thought of cupping her bra clad breast in one hand was irresistible. Sherry blushed when he did that. She was pleased at his doing that but blushed at the fact that it was a public setting and all her men colleagues were gawking at her perhaps wondering if they would have a chance at this too. Matt was making some body contact with her and his arousal was obvious. She noticed that she was getting aroused too and was terrified that her arousal would sow through. But if the events kept unfolding the way they were, then it would be a matter of time before it would become evident to everyone and that would be soooo humiliating, she thought with considerable dread. And Matt was finding the act of stroking her breast while spanking her and watching her face grow ever so vulnerable as she winced and surrendered, that he wished he could just whisk her away and screw her brains out. He also wished that this would continue to be part of their relationship, albeit in private. And Sherry too got into the providing variety act and on her own accord started adding "May I please have another" after the count and 'Thank You, Sir'. Roberts smiled and realized that giving her all the stripping and spanking stories to read in preparation had not been a waste and she had probably picked up some ideas from those stories.