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Story: Headmistress Gets Tickled (M/F)

white_man_super

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Feb 2, 2006
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The Detention (Fiction M/F)


It was approaching that time of the day when the Headmistriss of Brocklemead Secondary School realised that the weekend was about to begin. Friday afternoon at 2pm – with a little over an hour to go and she could hardly wait. It had been a difficult week due to a mountain of paperwork, internal disputes between teachers and of course disruptive pupils to which she was required to hand out punishments.

Although she was a single woman she relished the thought of a quiet night in nursing a stiff gin and tonic and curling up with a good book without a single noisy brat in sight.

As she leaned back in her leather chair and pondered on this pleasing thought for a moment, she failed to notice the sharp knock on her office door until a person emerged – Mrs Henderson, the deputy head. The headmistress assumed her professional pose and looked up. “Jill? What’s the problem?” asked the headmistress quizzically.

“I’m afraid I can’t make the detention slot tonight. My husband’s stuck at the airport and isn’t going to make it back until the morning. I don’t suppose…..” Jill looked hopefully at the headmistress who inwardly groaned. The detention slot was from 3.30 until 4.30 which was not in itself so bad but was indeed nonetheless a horrible infringement on her afternoon and evening plans. She knew she could hardly say no given the number of times Jill had covered for her at even shorter notice and so with a forced smile she nodded.

“No problem Jill. You get off and I’ll deal with it. Who is it anyway?”

“Bobby” replied Jill. “Nothing terrible. Just late with his homework for the umpteenth time. I’ve just given him the job of sorting out the book shelves in the library so if you can just sit with him?”

The headmistress nodded and smiled. “Thanks and have a good weekend!” replied Jill with a broad smile as she hurried out the door before the headmistress changed her mind.

At 3.25 and with a huge sigh the headmistress strolled briskly to the library where Bobby was already busy re-arranging books into alphabetical order.

“Bobby” the said mistress said sternly. “I’m surprised at you. If it had been any of the others in your gang then it would have been understandable but you’re a high achiever and should be above all this”.

“Yes miss.” Was Bobby’s flat reply.

“I don’t want to be here any longer than you do so lets just get this done then we can both go home. You carry on as you are and I’ll sort these out.”

The head mistress knelt down a few yards behind Bobby and started sorting out the opposite shelf of books, cursing to herself about the waste of time this was. Occasionally she would get down on all fours in order to place a book on the next shelf over or retrieve one if she noticed it was out of place.

Bobby would also turn around every so often and stare at her briefly while she was on all fours and then quickly turn back again before she knelt upright just in case she turned around and saw him. She was old enough to be his mother, well made but most importantly of all she was a woman of authority and that made her someone that Bobby desperately wanted to tickle. He had always harboured a tickle fantasy for older women and the headmistress fitted the bill perfectly. He stopped what he was doing for a moment to consider what it would be like to tickle her all over. Would she merely giggle, would she struggle, would she laugh uncontrollably, would she scream?

Bobby fought the feeling for a while but then came the reasoning: he was 16, leaving school in 3 weeks and tickling certainly was not a crime? What was the worst that could happen? The thought of actually doing it sent his heart racing. He tried to dismiss it but a voice told him there would never be an opportunity like this again. The school was virtually empty and it was just the two of them.

He chanced to look around again and this time he caught the headmistress still kneeling on the floor but stretching to place a book on the top shelf, causing her jumper to rise up and reveal her bare sides. That did it for Bobby. With his heart in his mouth he took a deep breath. He slowly and silently got to his feet and went over to the librarians desk and removed two school ties from the hook. Whenever students turned up with no tie for whatever reason they were always sent to the library to borrow a spare one in order to ‘look respectable’ as the headmistress would say.

Bobby stood silently staring at the headmistress who was still kneeling with her back to him and placing books on the middle and top shelves. With a final gulp of air Bobby rushed over and grabbled the headmistress by the waist and pulled her down to the floor where she was flat on her back. Before she could protest Bobby restrained each wrist with a tie and fixed them to the solid legs if the book shelf so that her arms were completely restrained and above her head.

Then came the inevitable reaction. “Bobby just what an earth do you think you are doing?” the headmistress barked. “Untie me immediately or this is going to cost you dearly young man”.

“I am going to untie you Miss I promise but I just want to ask you something first” said Bobby without so much of a flicker of a smile upon his face.

“Fine, fine just ask me and untie me” said the headmistress, voice sounding urgent and angry as she tugged on her restraints.

“Are you ticklish?” asked Bobby casually. Suddenly the headmistress’s mind was racing. Struggling not to betray her thoughts she kept a stern look about her as she replied “No I am not now untie me now before this gets any worse for you.”

“Miss I just want to check ok. If you’re not ticklish then I’ll untie you and take whatever punishment you give me but if it turns out you are then I’m going to tickle you to death”.

The headmistress was shocked by what she was hearing and her heartbeat went out of control. She knew she was going to be tickled and yet had to maintain defiant. The only thought that kept coming to her mind was “I hope he doesn’t tickle me there”.

“Now wait Bobby…” said the headmistress as Bobby knelt down next to her. “Don’t do this. You’re in enough trouble….”

Too late. Bobby’s fingers were gently wriggling and massaging her ribs, causing the headmistress to tighten her lips and close her eyes. She could feel the ticklish sensations but they were not strong enough to cause any serious reaction as long as she tensed herself.

“Bobby stop this!” she said through gritted teeth and fast enough to avoid letting out a giggle. Bobby continued to massage her ribs and tummy causing the headmistress to squirm and screw her face up. The tickle sensations were beginning to take hold and she knew that a giggle would escape at any moment but all of a sudden it stopped. Bobby removed his fingers but remained kneeling beside her.

“Are you happy now!” scowled the headmistress. “You’ve found out what you wanted to and now its time for this to end RIGHT NOW!”

Bobby was very far from giving up. “Wait Miss, I see what the problem is”. He gently lifted the bottom of her thick jumper up all the way over her head so that her wrists and hands remained in the sleeves but exposing her armpits and all of her tummy and ribs. Bobby’s heart raced beyond reason when he saw her black bra and deep cleavage.

“Bobby!! What the hell are you doing! I said enough and I meant enough!” Despite the firmness in her voice the headmistress knew that she was going to be tickled and that this time there would be no protective layer preventing the tickle sensations from rippling through her. That was the least of her worries though. “As long as he doesn’t tickle there” came the panicky thought again.

Meanwhile Bobby’s fingers were inches away from her bare ribs. “Bobby don’t do…” her sentence was cut short has Bobby’s fingers began to dance around her ribs, sides and all over her tummy. The headmistress gasped and just about managed to mouth “Bobby!” through gritted teeth as she fought the tickle sensations and the giggles that were now flowing out. HehehehehehehahahahahahahahahahaSTOheheheheSTOPhehehehehehehePLEEESEEEEhehehehehe.

Encouraged by her helpless state Bobby’ taunted her “But Miss I thought you said you weren’t ticklish” he teased as he now worked his fingers deep into her sides and tummy and manoeuvred himself to sit on top of her.
“Bobby! Nooooohhhhhhhhhahahahahahahahahahahahahahahahahahhahahahahahahahahahahahahaha” the laughter was now gushing out as Bobby’s fingers wriggled furiously between her ribs, getting ever higher toward her armpits. All the while Bobby’s stared in delight as the normally stern headmistress laughed herself silly and as her breasts heaved up and down ready to burst out of the overstretched bra.

The headmistress suddenly shrieked as Bobby unexpectedely blew a raspberry on her belly button before suddenly placing all of his fingers in her hollow armpits and using a combination of wriggles and circle motions that caused the headmistress to scream. AAAAAhhhhahahahahahahahahahahahahahahahahahahahastophahahahahahahBobbyeeeeehehehehehehehehehehehehehehepleeeeeseeeehehehehehehehehehe.
The headmistress pulled hard on her restraints and amid her laughter and screaming managed to think to herself “please don’t let him tickle me there”.

Bobby focused on her armpits as he realised that there was one spot that was especially sensitive and so he wriggled and scratched it madly causing the headmistress to fall into silent laughter, managing only the occasional scream between breaths. Bobby smiled in glee as she just sunk into a laughing fit and her breasts shook from side to side barely being held together by the ill fitting bra.

Eventually the armpit torture ceased and Bobby’s gently worked his fingers back down toward her sides, easing off slowly so that the exhausted headmistress was merely giggling. HehehehehehenoheheheheheNOheheheMOREhehehehehee.

Bobby seemed to hear her for he suddenly stopped. Neither of them spoke although inwardly the headmistress breathed a sigh of relief as she thought to herself “well at least he didn’t tickle me there!”

As she lay there panting she became aware that Bobby was no longer sitting on her. “Bobby! What are you doing!” she said faintly has she felt his hands reach up her skirt and brush over her inner thighs. It then became clear that Bobby was reaching for her tights. As his hands tugged at the black stockings he felt the lacy material of her knickers and the bareness of her thighs and legs as he pulled the tights all the way downwards. Bewilderment turned to fear as the headmistress realised what was happening. Her eyes widened in terror as her shoes were yanked off her feet and the tights used to tie her ankles. The thought that had kept coming to her throughout her ordeal was now being manifested verbally as she pleaded with Bobby.

“Bobby, listen, you’ve tickled me half to death ok now I won’t tell anyone but please I beg you…don’t tickle me there! Not my feet!”

Bobby merely smiled as he locked her left foot in one arm and with the free hand began slowly counting each toe. This caused and instant reaction as the headmistress clenched her eyes shut in anticipation for the worst that was to come.

As she squirmed with each toe that was wiggled suddenly she heard her own loud scream bellow out. Araaahhhhaaaaaaaaaaaaaaaaaaaaaah! As Bobby began raking his fingers up and down her bare sole, switching to spidery scribbles and then back again.

ArrraaaaahahhhhahahahahahahahahahahahahahaNOOOOhahahahahahahahPleeeeesHHHHAAAssseeeIhahahahahBEG YOUhahahahahahahaaahahahahaARRRAaaaaaahhhahahahahahahahahahahahhahhahhhhhhSTOOOOPPAHAHAHAHAHAHAHAHAHAHAHHAHAHBOBBYEEEHAHAHAHAHAHAHAHAHAPLEeeeeeshahaha.

The headmistress was hysterical as she thrashed her whole body from side to side in ferocious laughter that was accompanied by ear piercing screams. Meanwhile Bobby continued in his frantic finger scribbling only ever stopping to use his tongue on her bare sole which in turn brought more screams and pleas for mercy.

After a while Bobby allowed the headmistress time to regain her breath but no words were spoken until she finally said “Bobby, please let me go now. You’ve seen I am ticklish and you have tickled my feet so please no more.”

She was still panting and looking dishevelled although inwardly she had partly enjoyed it but would not dare admit this to the young pupil.

“I’m almost finished Miss.” Said Bobby.

“What!! You’ve just tickled me to death Bobby now come on, please let me go.”

“But Miss I only tickled one foot, there is still one more to do.”

“No! Bobby please no. I’ll do anything. Just tell me what you want me to. You can tickle me anywhere else. Please, anything, just tell me but not my feet again ok”.

“Really? Anything? What if I said take your bra off? Would you do that”?

The headmistress was stunned for a moment but considered the torture of having her feet tickled again.

“Alright Bobby. We’ll make a deal now ok. If you absolutely promise not to tickle my feet then I’ll remove my bra.”

“Can I still tickle you some more?” asked Bobby now full of confidence.

“Only if you promise to not tickle my feet and let me go very soon. You will let me go soon won’t you?”

“OK Miss”. Bobby sat on top of her and began from where he started, wriggling his fingers around her ribs and all around her armpits causing lots of laughter, giggles and the occasional scream. As Bobby observed her struggling and squirming he noticed her breasts bouncing up and down and remembered that she had agreed her bra could be removed so whilst he kept one hand squeezing her ribs which caused little more than helpless giggles he used his free hand to rip off the bra and watch her breasts spill out. He then continued the tickle frenzy, using his lips and sucking on her ribs to magnify the tickle sensation whilst at the same time tickling her tummy and armpits.

Although laughing and half heartedly pleading with him to stop, the headmistress started to enjoy herself and between laughter said “my feeeeeheeeeeeeeethahhahaha”.

Bobby understood and grabbed a foot and began furiously tickling the soles to which the headmistress screamed in hysterics. Then whilst tickling a sole gently with one hand he used the other to reach up her skirt and tickle the backs of her knees and then her inner thighs which brought squeals of laughter.

Bobby could not work out if it was the tickling of her sole that was causing the most laughter or if it was his other hand exploring her thighs. No matter, he used his spare hand to continually squeeze her thighs, noticing in the process that she was in fact wearing a thong as his hand went further and unnoticed.

As Bobby’s fingers began to tire he paused to rest.

“I think I’m done now Miss”. He undid her restraints and helped her track down her bra which had previously been tossed aside.

“So I suppose I’m in big trouble now” asked Bobby with a half smile.

“Maybe, maybe not” replied the headmistress.

“Miss?” said a puzzled looking Bobby.

“If you agree to tickle me again the way you did today on a regular basis then I promise no one will ever know”.

Bobby grinned. “Deal!”

The End
 
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