Jessica at the Finishing School Pt. 02

This story was written in 2000, annoyingly I am having to transcribe it from a physical copy since that is all I have available. I hope you enjoy it and you think it worth my efforts. This is part one of four or five, since the feedback has been so positive I am cracking on with the rewriting/transcribing with the aim to get at least one part done each week until it's finished.

I'm posting this under my old name because it was written so long ago, and so it probably should be with my older stories. I have more of this kind of story (in hard copy) so I may do some more if people enjoy it and want more.

Check out my newer stories under my new name Robert_Anthony.

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This story is set in a fictional college/finishing school called Maverley Park. Ostensibly the school is reserved for very rich clients, needless to say all characters are over 18!

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In her daze, Jessica had not noticed that Helen had not been at her desk when she left. In fact Helen had not been at her desk from the moment Jessica had been called in by the headmaster.

After Jessica had left, the headmaster opened his door to see Helen just returning to her desk, she looked a little flustered and the headmaster knew where she'd been and exactly what she'd been up to.

"Helen. Five O'clock, I want you in here!"

He slammed the door behind him, saying not another word and leaving Helen to ponder her fate.

The rest of the day passed slowly for Helen as she waited for 5PM to come. She had cum watching the headmaster's exploits with Jessica but she wanted to taste his cock herself and as the hours dragged by she became more and more horny and impatient.

At two minutes before the hour, Helen got up from behind her desk and locked the outer door of the office building. It was nearly dark outside and the car park was almost empty. Despite the fact that it was a boarding school, about half the teachers lived in a nearby town and went home after teaching hours.

Helen felt the radiator by the door, it was just kicking in and there was quite a chill in the air. She walked back towards her desk and then diverted to the door to the headmaster's office. She knocked gently and waited a few seconds for him to answer.

"Come in."

Helen slid her fingers around the door handle, depressed it and slowly pushed the door open. It was quite gloomy in the office, the blinds were closed and only one light was on. The headmaster rose from behind his desk and walked towards her.

"I think you've been a naughty girl today, haven't you?"

"No Sir, I was just..."

"You were just watching the security camera is what you were doing, girl."

Helen felt her stomach flip, she loved it when he called her 'girl' in that particular tone of voice.

"No Sir, honestly I just had to go and see another member of staff about someth..."

The headmaster raised his hand to stop her digging herself any deeper.

"Helen, I simply don't believe you. I'm quite sure the second that door closed you were out of your seat and off into the back room... well I hope you enjoyed the show, because now it's your turn to be punished."

Helen shuddered as he spoke the words, she loved being punished and she loved being forced to take whatever punishment the headmaster deemed necessary.

He walked up close to her, grabbed her roughly by the arm and pushed her towards the chair on the nearside of the desk, the one that had parted Jessica's legs so efficiently. Then he bent her over its back, so that her head was down near the seat and her ass was up in the air.

"Stay there!" He commanded as he walked back round the desk and opened one of the drawers. He pulled out a large leather covered box and placed it on the top of the desk. Opening the lid, he retrieved a couple of leather cuffs, two short lengths of thin chain and a couple of padlocks.

The headmaster then bent down to the foot of the chair and fitted the cuffs to Helen's wrists. Then he wound the chains around the legs of the chair and secured these to the cuffs with the small padlocks.

"There, that should keep you in place while I discipline you!"

Helen groaned with a mixture of apprehension and excitement. She knew that the headmaster was really annoyed with her and was expecting to be severely chastised, she just hoped he wouldn't leave her frustrated at the end of the session.

The headmaster stood up and returned to the box on his desk. He pulled out another item and slipped it into his pocket so that she couldn't see. He looked down at Helen, she had removed her glasses before she came in and her dark hair now fell forward over her face. She was still fully clothed and the headmaster decided that he would address that immediately.

He placed his hands on the back of her silky red shirt and tore it straight up the middle of her back. He struggled a bit when he got to the collar seam, but eventually he managed to rip through that as well. The two halves of the shirt fell from her body and slid down her arms, gathering around her elbows and flowing down to the floor. For her part, Helen let out a soft groan as she felt herself exposed to the air.

The headmaster stroked her back for a moment before unfastening her bra, which fell the same way. He reached beneath her and roughly squeezed her breasts before maliciously pinching her bullet-hard nipples.

"You never learn do you Helen... you never learn to just do as you are told. Do you know why that is? I'll tell you why, because you're a horny little bitch who can't keep her fingers out of her cunt for five bloody minutes."

He was very rough with her nipples, but she only felt pleasure as each squeeze and twist served only to make her pussy even wetter than it was before she came into the room.

"I hope you haven't been playing with yourself all afternoon... there's still work to be done around here, and don't you forget it." warned the headmaster.

He released her nipples and a small moan escaped Helen's lips. Then he ran his hands down her back, over her arse and down her black-stockinged legs.

"Such slutty stockings, anyone would think you were trying to attract other men... is that what you want Helen, other men? Maybe you would like more than one of them at that. You would probably like a whole bunch of them to abuse you wouldn't you? Four or five of them taking turns with your pussy, ass and mouth, eh?"

Helen groaned louder, she was a real slut and she knew it, and the headmaster loved to play on it. He knelt down behind her and pushed her skirt up to reveal her expensive black lace knickers.

"Oh Helen, it gets worse... this underwear can only mean one thing."

The headmaster spanked the insides of her thighs lightly until she moved her legs further apart. He then slid his fingers into the part of the cloth that covered her ass and pulled it to the right. Helen felt his breath on her ass and waited desperately to feel his tongue.

The headmaster pulled her cheeks apart and leaned forward to tease her pussy with his tongue, the tip of his nose gently brushing against her puckered hole. After a few extremely light strokes, which tormented Helen because she could barely feel them, he moved his head up between her cheeks and began to tongue her asshole.

"Ooooooooh yes, lick my arsehole... I love it," moaned the secretary.

He continued to lick her arse, then slid one finger into her sopping, slippery slit. Helen started to grind herself against his probing digit and tongue until her muscles started to tighten in anticipation of release.

Abruptly the headmaster pulled away and left her hanging.

"Noooo, please don't stop, I was so close..."

"I'm well aware of that you little whore, but you haven't been punished yet and you're certainly not going to cum until you have."

Helen's head sank dejectedly towards the chair seat as the headmaster pondered his next move. After a couple of seconds thought he walked over to the wall and pulled something down from a peg.

"No, please not the cane, it hurts so much, please!"

The headmaster laughed at her pleas and took his place at her side, ready to begin inflicting the pain she both craved and hated.

"Please Sir, please don't cane my poor arse, I know I've been bad, but I can make it up to you. I'll do anything you want me to, but please don't cane me!"

The headmaster swished the cane through the air a few times and then gently placed it on the cheeks of her arse.

"What a pity you are such a very bad girl Helen, if you weren't so incorrigible then I might have been kind enough to warm your poor arse first, but as it is..."

"No please, please don't... please."

"I'll tell you what I'll do Helen. If you promise to be a good girl and to take your punishment properly, then I will give you a treat. But if you whimper and scream like you usually do then I will take it away again... do you understand?"

"Yes Sir, I promise."

The headmaster removed the cane and reached into his pocket and pulled out a good sized vibrator. He turned it on and set it to full speed, then reached down between her legs and forced it into her slippery hole, bringing a sigh of pleasure from his secretary as the thick plastic tube stretched her wanton pussy.

"Hmm, these knickers are going to be in the way as well..." said the headmaster as he roughly pulled them down her legs. When they reached the floor he told her to step out of them and he placed them on the desk in front of her.

Then he replaced the cane across her arse, it felt even worse now without the thin layer of fabric between the cold, hard rod and her pale skin. The headmaster held it there for what seemed like an age to Helen, before she felt it lift and rapidly return. The pain seared through her and she clenched her entire body as the red stripe appeared across her cheeks.

"Ooooooow!" She wailed loudly.

Immediately she felt the vibrator pulled out of her and the buzzing stopped as it was switched off.

"One stroke, and you've already failed... that was absolutely pathetic."

"I'm sorry Sir," she cried. "Please give me another chance."

"And why should I do that, girl?"

"Please, please I beg you... please don't take it away."

The headmaster smiled to himself and looked down at the wet, shiny plastic he held in his hand.

"Well, let's see... this looks as though it's almost wet enough to..."

The headmaster's voice trailed off as Helen felt his fingers prise her ass cheeks apart and she felt the head of the now silent vibrator push against her tight, pink hole. She gritted her teeth as her muscles stretched to accommodate the intruder and the brief stab of pain quickly gave way to pleasure and an overwhelming feeling of fullness.

"Is that better?"

"Yes," sighed Helen. "Yes, thank you Sir..."

The headmaster slowly turned the base of the plastic cock and the motor whirred into life once again. Helen trembled with pleasure as the vibrations spread through her arse and sent a warm glow to her dripping cunt. In fact she was so busy concentrating on these sensations that she almost forgot about the cane, and so when the second blow hit her the shock was even worse.

"Aaaaaaaaaaaaaaggggggggggghhhhhhhhhhh" wailed the secretary as the cane stung her flesh.

The headmaster angrily snatched the vibrator out of her arse and threw it on the floor where it continued to buzz annoyingly. He then laid four more stinging angry red stripes across her cheeks before pausing to decide his next move.

Helen was close to tears, and when the headmaster viciously added another two strokes the tears overflowed and spilled down her cheeks. Her arse was on fire and sensing that she'd had as much as she could take for now the headmaster dropped the cane and unbuttoned his trousers.

"Don't cry my little whore, Daddy has something special for you."

He moved right up behind her and guided the tip of his prick straight into her arse. His cock was slightly thicker than the vibrator and so her ass had to stretch again to accommodate him. As he forced his cock into her he reached underneath her and rubbed her clit roughly with his fingers.

Helen shook visibly as the headmaster built up the speed of his thrusts and the tightness of her ass pulled him closer and closer to his own orgasm. Each stroke felt harder and deeper than the one before to Helen, and barely thirty seconds after he had entered her she felt herself spasm as a huge orgasm tore through her body and clamped her muscles around his driving prick, pushing him over the edge and forcing him to spurt violently inside her.

The headmaster's legs gave way and he collapsed onto Helen's back. He lay there for a few moments to catch his breath and then pulled himself upright again. As his cock slipped from her ravaged arse a stream of cum slid from her stretched hole and he watched it slither obscenely down her inner thigh. He reached out a finger and gathered some on the tip, before bending down and reaching beneath the mess of her hair to push it between her open lips.

He stood up again and looked down at her ass, the stripes he had laid on her were clearly visible and well positioned. He congratulated himself on his accuracy then bent down and released Helen's hands from the cuffs and pulled her upright. As she turned to face him he kissed her full on the lips and despite the pain that was burning through her backside Helen returned the kiss, her tongue probing his mouth and mingling with his, sharing the remaining taste of his cum.

Eventually the headmaster broke away and allowed her to sit down as he picked up the various discarded items from the floor.

"I take it you have a jacket of something?" He said, indicating her torn shirt.

"Yes Sir," she replied, still a little breathless.

"Good," he said as he walked towards the door. "Oh and get that Jessica girl back in here on Friday. She needs a bit more special tuition I feel."

He winked at her and then left her to tidy up the office.

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Several days passed and due to various other commitments Friday's proposed meeting never happened. Of course Jessica didn't know any of this as the headmaster had never indicated to her exactly when she would be recalled.

The weekend also proved to be rather busy, but Monday morning's second lesson was interrupted by a note summoning her once again to the headmaster's office.

Within a few minutes she was walking towards Helen's desk again and this time the secretary looked up and smiled.

"Ah Jessica, we've been expecting you."

Jessica didn't quite know what to make of the 'we' part of that statement, but she didn't have too much time to think about it as the older woman stood up immediately and walked over to lock the outside door. Jessica watched as she walked back towards her and then led her straight into the headmaster's office without knocking or waiting for a reply.

The headmaster looked up and gave Helen an annoyed glance, she was impatient and he didn't appreciate it when people came into his office unbidden. He resolved to punish her later for that, but for now he was more interested in Jessica.

"Hello again Jessica, please sit down."

He waived his hand at a chair that was positioned to one side of his desk.

"Have you been studying hard this week?"

"Yes Sir, I've been doing my best to stay out of trouble."

"I'm glad to hear it Jessica, you don't want to disappoint your father do you?"

"No Sir."

"Good... well, our last meeting was satisfactory but I've decided that you really need a little expert tuition if you're ever going to learn to suck a man's cock properly."

He stood up and unbuttoned his trousers, then let them fall down his legs.

"Helen, come here."

Helen moved quickly towards him and he pushed her down to her knees.

"Show Jessica how a real woman sucks cock."

Helen pulled his shorts down and the headmaster's cock sprung forwards, growing and thickening in anticipation of Helen's warm, wet, skilful mouth. The headmaster put his hand on the back of her head and Helen's lips engulfed the head of his erect prick. He sighed as her silky lips travelled the length of his shaft, while Jessica couldn't believe how much of his cock was disappearing into the other woman's mouth. The headmaster noticed her surprise and remarked...

"It is quite impressive isn't it? I'm sure you'll get the hang of it soon enough, I'd hate for you to leave the school without learning to take a whole cock deep into your pretty little mouth too."

Jessica thought it unlikely, but she kept her thoughts to herself. She had learned that much over the last few days, if nothing else. She continued to watch with increasing fascination, as Helen throated the thick cock, her face pressed right into the headmaster's groin as she gagged around his length. At one point she pulled back and displayed the full length of the headmaster's cock, it was soaked with spit and Helen worked it with her hand while she caught her breath before forcing her head down onto it once more.

For his part, the headmaster gradually started pumping his cock into his secretary's mouth, literally fucking her throat and holding the back of her head to stop her pulling back. Now he was in complete control and fucked her hard and fast, meanwhile Helen, in a show of submission and obedience, clasped her hands behind her back, offering no resistance to the rough fucking he was giving her mouth.

As she watched, Jessica found herself becoming very aroused, she suddenly realised she was pressing her hand between her legs and rubbing her pussy through her skirt.

Pausing for a moment, the headmaster noticed what she was doing and ordered her to lift her skirt. Jessica took hold of her skirt and obediently lifted it up around her waist.

"Now spread your legs Jessica, rub your pussy through your knickers for me."

Jessica was embarrassed and lowered her face, but her legs parted and her hand fell between her creamy thighs, she was wetter than she thought and her white cotton panties were already soaked through and almost transparent.

The headmaster forgot about Helen for a moment while he watched Jessica begin to rub herself as he had instructed. Jessica looked up for a moment and saw Helen reach between her own legs and slide her hand under her skirt, she was dripping wet and quickly worked a finger between her lips as she took the warm, throbbing cock inside her mouth again.

After a few moments Helen lifted her slippery finger from between her legs and pushed it up between the headmaster's cheeks, he grunted as she forced it into his ass and started to tease his prostate. The intense stimulation nearly pushed him over the edge, but at the last moment he managed to stave off the point of no return and gave her a few extra hard thrusts for her trouble.

"You are such a cum-greedy slut aren't you, don't you ever get enough?"

Helen grunted and used her other hand to squeeze his balls, desperately wanting to taste his cum and to suck him dry.

The headmaster pulled Helen's head back and smeared his cock all over her face, before offering his balls to her mouth. She greedily sucked on them as he gently stroked his cock, tempted for a second to just give in and splatter her face with his hot creamy load.

He turned to look over at Jessica, who was clearly turned on and rubbing her pussy with abandon.

"That's it Jessica, now pull your knickers to the side so I can see your pretty little pussy."

Jessica obeyed with only a moment's hesitation, exposing herself completely and feeling even more turned on that he was watching her touching herself.

"Now... slide your fingers inside your tight little cunt."

Jessica shuddered as her fingers pressed against her wet slit, the feelings of shame and embarrassment mingled with her complete arousal confused her, but as she worked her fingers deeper she gradually gave in to the feelings that were consuming her.