Jessica at the Finishing School Pt. 01

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 three or four, I am going to see what the feedback is like before I decide whether to do the other parts as it's quite laborious and truthfully the story needs quite a bit of rewriting along the way, and I need to decide if my time is better spent working on something new.

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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The knock at the door was faint and the headmaster decided to ignore it. After a few seconds he heard the knock again, louder this time. He rose from his desk, smiling at his secretary who sat in the chair next to his and walked towards the door. His cock was semi-hard but he didn't think the girl would notice... not yet anyway.

As he reached for the door handle her noticed that his hand was still wet with the juices from his secretary's pussy. He smiled to himself again and wiped it on his trouser leg, then opened the door.

"Aah, Jessica Warne... shouldn't you have been here ten minutes ago?"

"Yes Sir..."

"Well your punctuality leaves something to be desired to say the least, never mind, we'll address that point later."

He was about to tell her to sit down, but then thought better of it and simply left her standing in front of the large oak desk while he milled about his office for a few moments. Eventually he stopped fiddling with things and took his place, directly in front of her.

The girl stood trembling slightly, she was not used to being in trouble and was therefore not a 'cocky' girl like some of the others at the school. The headmaster was more than aware of this and felt no shame in his ability to exploit her naivety. She vaguely wondered why the headmaster's secretary was also sitting behind the desk, but thought little of it.

"Now Jessica," began the headmaster, not bothering to introduce his secretary or explain her presence. "I've been hearing some rather disturbing reports about you."

The girl's expression betrayed her surprise at this, but she said nothing. She looked straight at the headmaster... he was in his mid-forties and clean shaven. His dark hair had a few whispers of grey running through it, be he didn't look 'old'. His complexion was quite dark, but it seemed right with the colour of his hair.

"Several of the teachers have told me that your work of late has been of a very poor standard and that you are not applying yourself to the work that you are being set. On top of this it transpires that a girl who very much fits your description was seen in a state of undress with a local boy in a field at the back of the school a few days ago."

Jessica's mouth dropped open.

"So unfortunately, I'm obliged to ask what you have to say for yourself."

The headmaster leaned back in his chair and crossed his arms across his chest, waiting for the girl to find her voice.

"I... I don't know what to say... I... it wasn't me in the field, I swear!"

The headmaster exhaled loudly and leaned forward, his hands flat on the desk.

"That's all very well Jessica, but the thing is, I simply don't believe you. Your teachers are clearly dissatisfied with your application and I am reliably informed that it was indeed you in the field. You may protest your innocence, but personally I don't think it's going to wash with your Father when I speak to him later on this evening."

"But I didn't..."

In actual fact the girl had done nothing wrong to justify her presence here, other than to catch the eye of the headmaster and his secretary. Jessica wasn't the first girl to be lured into the headmaster's office under false pretences either. Jessica fitted the bill perfectly, she was sent to boarding school by her parents several months before and her timid nature and attractive figure had soon alerted the headmaster's attentions.

"What didn't you do Jessica?" Enquired the headmaster.

"I wasn't in the field with a boy!" Pleaded Jessica.

"Well you may say so, but I have been positively assured that it was definitely you."

"No, no it wasn't!"

She was starting to panic a little now. Her Father had quite a temper and the last thing she wanted was to have her allowance suspended. God knows what he would do if the headmaster told him she had been seen in a field half undressed with a boy.

The headmaster studied her face for a moment. Jessica had only just turned eighteen, but was quite well developed. She wasn't stick thin like a lot of the girls in his charge, in fact by the standards of most of the rich 'daddy's girls' at this school she was almost 'curvy'. In particular, her breasts looked quite spectacular beneath her regulation white cotton shirt.

Jessica had her long blond hair tied in a plait and the headmaster couldn't help but imagine what it would be like to wrap it around his hand as he fucked her from behind, maybe even sliding his thick cock deep into her tight little asshole as he used her hair to control her like a lead.

"Well Jessica, what am I to do?" Asked the Headmaster. "I have already spoken to your father's secretary and he is expecting me to phone him back later on this evening. Of course, he doesn't know why I am ringing, so I suppose that if this can be worked out before then I could always tell him that I was calling to congratulate him on his daughter's performance in her first term..."

Jessica's face brightened at this, which indicated to the headmaster that she obviously had no idea what he was about to suggest.

"The thing is Jessica, a few years ago you may remember that your sister Charlotte was sent here for a few years... well, like you, Charlotte got herself into a bit of a mess with a local lad - of course, your father never heard about it, I saw to that. But as I recall, your sister was absolutely terrified of what your father would have done if he had found out about it. She seemed to think that if she were expelled from here she would be transferred to a school with a much more oppressive regime."

Jessica realised that the headmaster was talking about a Catholic finishing school that was one of the alternatives discussed when choosing a school for her.

"I don't think you would like it there Jessica, some of those nuns are positively inhuman to the girls in their charge."

Her face gave away that he had found her weakness. Jessica was petrified of nuns and had begged her mother not to let her father send her to that other school, she couldn't face being expelled and then sent there, not now she'd made friends here.

"Jessica, I want to help you, I really do, but I have a duty to your father. What we must find is a compromise, where I feel that you have been suitably punished and where I will not have to bother your father with your foolish behaviour."

"Yes Sir." Jessica almost didn't care what the punishment would be as long as she didn't get into trouble with her father.

"The thing is Jessica, you have been very badly behaved and I feel that you may need to be punished very severely for the way you have acted. Wouldn't you agree?"

"But I didn't..." she started to protest.

The headmaster's eyes narrowed and he slammed his hand down loudly on the table.

"Don't lie to me girl, you're only making things worse for yourself."

"Yes... s, sir," stammered Jessica meekly.

"Good. That's what I wanted to hear. I don't offer help to all the girls you know Jessica... only the girls who I really believe deserve a second chance. You do 'deserve' a second chance don't you?"

"Yes Sir, I promise I'll behave..."

The headmaster couldn't help sneaking a sideways glance at his secretary - Helen. Out of sight of the young girl she had sneaked her hand up under her short skirt and was casually rubbing her clit through her soaking wet underwear. The headmaster smiled to himself, he had been fucking Helen for four years now and was never disappointed by her. She was a dirty bitch and her mind was as depraved as his. She also liked the taste of a girl's cunt almost as much as she liked to lick her own juices and the cum off his cock after he'd fucked her. The headmaster always liked that. She was also the first woman who he'd ever met who never objected when he slipped his thick cock into her arse. He liked that even more...

The headmaster's cock was starting to really stiffen now and as he was becoming harder he wished he could just cut the crap and fuck this little slut. But he knew that if the plan was to work long term he had to go through the usual motions and so he returned his attention to the nervous girl in front of him.

"Now listen Jessica, if we are to have an agreement over this little matter then you must do exactly as I tell you, okay?"

Jessica looked even more nervous now, but she didn't want to blow it now that she'd got the headmaster on her side. Not while the phone call to her father was on the table.

"Yes sir, I'll do whatever you say, I promise..."

"You're making a lot of promises Jessica, I hope you aren't going to let me down."

"No sir," she stated firmly.

"Good girl. Well the first thing I want you to do for me is to... unbutton your shirt."

The headmaster leaned back in his chair and beneath his desk, out of sight, his right hand automatically fell into his lap and started gently rubbing his throbbing prick through his trousers.

The girl hesitated and the headmaster prompted her.

"Come on Jessica, I've been very generous with you... you don't want me to make that phone call in a bad mood do you?"

Jessica looked at the headmaster, then his secretary, but found no compassion in either of their faces.

"I'm waiting Jessica."

Jessica slowly started to undo the buttons of her white cotton shirt. As each button came undone so a little more skin was visible and the headmaster and Helen both started to become more aroused as their latest adventure got underway. Both always got a tremendous rush from the first time with a new girl, in fact their adventures usually only lasted a few weeks as after this time the girls were usually fully corrupted and lost their innocent appeal.

At the end of the day, everyone was a winner. The girls found out about their sexual needs and capabilities in a safe environment and the headmaster and his secretary got to fuck a seemingly endless string of young girls, each time delighting in the opportunity to corrupt their young minds while pushing them to their sexual limits.

"That's good Jessica, keep going..." encouraged the headmaster.

Jessica's trembling hands struggled with the tight buttons but she persisted, still fearful of her father's raging temper.

Eventually her shirt fell open and the pair's eyes fell upon Jessica's chest. Helen's finger continued to tease her clit, though Jessica would never have noticed, especially as her head was dropped forward in embarrassment.

"Now look at me and pull your bra down Jessica," again the headmaster's voice came.

Jessica didn't look up as she hooked her fingers into her bra and pulled it down so that her fleshy breasts fell free. The headmaster licked his lips as he drank in the sight of her young tits with their hardening nipples. The office was always quite cold and the chilly air was affecting her whether she liked it or not.

"Now come here Jessica... and kneel down in front of me." The voice was giving an order now, there was no mistaking that.

Jessica slowly rose and started moving around the desk.

"Keep looking at me Jessica," warned the headmaster.

Jessica slid around the desk as the headmaster started to turn his chair towards her. She paused for a moment and then started to sink to her knees. Suddenly the headmaster's mood changed. He stood up, pointed to the door and ordered her to 'get out'.

Confused, Jessica hauled herself to her feet and hurriedly began buttoning up her shirt as she ran to the door.

The headmaster turned to his secretary and smiled as the door closed.

"Get her back in here tomorrow morning at ten, that'll give me time to edit the video," he said as he began unbuttoning his trousers and pushing them down to reveal his aching, rampant meat.

"And now... as I've had to delay fucking that sweet, innocent girl... I think I'll have to take out my frustrations on you. You can start by sucking this, you horny little slut. I bet your pussy is dripping wet after that little performance isn't it?"

Helen started to answer but was cut short as the headmaster's cock entered her mouth. She was on fire after that little episode and would do anything he wanted right then. Her lips opened as he pushed his hard cock inside and then slid along the length of his shaft, lubricating it with a mixture of saliva and her red lipstick.

He looked down at her as she sucked him, she was attractive and still in good shape despite approaching her late thirties. Her shoulder length, dark hair and glasses gave her an air respectability he appreciated in a secretary, in fact, except for her choice of lipstick she actually looked quite 'prim'. No one would ever guess she was actually a completely depraved slut.

Her head started to move faster on his cock and he knew he wouldn't be able to last much longer. He felt her fingers stroking his balls and then her other hand reach between his legs, seconds later he felt her index finger slide slowly between his cheeks and pierce his asshole. Almost immediately he felt the spunk churning harder to escape his full, aching balls.

He let out a gasp as he started to cum and his cream spurted into Helen's willing mouth. After the first few spurts she pulled her head back, swallowed his load and used her tongue to tease the remaining cum from his angry looking cockhead.

"That's right, lick it all up you bitch," the headmaster growled. "I know you would rather have it in your dirty ass, but you'll have to wait a while."

She continued to suck and lick his cock until it became almost painful and he pulled it away from her and refastened his trousers. He looked down at her and saw a pleading look in her eyes. He pushed her chair round and knelt on the floor between her legs, pushing them apart as he did so. Helen sank bank in the leather chair and lifted her legs over the arms, giving the headmaster better access to her soaking wet cunt.

The headmaster slid his rough hands along her thighs until he reached her black underwear.

"You little whore, your knickers are sodden," he said as he hooked them with his fingers to reveal her slippery, pink flesh.

Helen groaned as she felt the cold air flow over her exposed lips and then groaned louder still as she felt his tongue part her and rub her inner walls. He licked her for a while, before slowly licking all of his fingers and coating them with spit. As he did so he looked her straight in the eye, relishing the lust he saw there.

He slid one, two then three of his fingers into her sopping hole. Helen grunted with the intrusion but quickly accepted it as he had started to play his tongue over her aching clit. He knew it wouldn't take long, but just to speed things up he slid his other hand underneath her and quickly forced a digit into her asshole. As he reached the second knuckle Helen's body bucked beneath him while he struggled to keep his tongue in contact with her clit, such was the violence of her orgasm.

When she had recovered her breath he slid up her body and kissed her on the lips. Helen loved the taste of her own juices and eagerly swirled her tongue into his mouth to sample it. He smiled at her again and stood up, looking down at her with her legs still spread wide and her skirt rucked around her waist.

"Don't forget, ten o'clock tomorrow. I'm of to do the necessary..."

He walked towards the door without looking back while Helen dragged herself out of the chair to smarten herself up before returning to her own desk and continue with her work.

-- -- -- -- --

Jessica didn't get much sleep during that night. She was very confused by the whole episode and a little fearful. Had the headmaster already called her father, and if so what had he told him? Would her father believe her if she told her side of the story? Should she tell another of the girls at the school about her situation or should she keep quiet and hope that it would blow over?

About eight her alarm went off and what little sleep she had achieved was finally curtailed. She lay in bed for a few moments, thinking over how she should approach the day and decided it would be best to carry on as normal. She got out of bed and had a shower to try and wake herself up for her lessons. After all, she didn't want any more complaints from the teachers getting back to the headmaster.

Jessica met her friend Kelly in her first lesson and wondered for a while whether she should confide in her. Eventually she decided against it and got her head down into her books. She hated maths but at least she felt safe here. She looked up at the clock on the wall, it was 9:50am. She returned to her studies for a few moments until the door of the classroom opened. Another girl, who Jessica recognised as Lauren Ball, walked into the room and passed a note to her teacher.

Lauren was quite well known at the school, she had hung around with Jessica's group of friends at the start of the year but in recent weeks her attitude and general behaviour had deteriorated somewhat as she had started to mix with some of the 'lesser' girls at the school. Jessica thought it was ridiculous that she should have been reported to the headmaster when girls like Lauren were cavorting around , in fact, thought Jessica, it wouldn't be any great surprise if it turned out that it had been Lauren who had been the one seen in the field behind the school.

The teacher in the classroom stood up and took the note from Lauren and opened it and read it before addressing the class.

"Jessica Warne, you are to report to the headmaster's office at ten o'clock."

Jessica sat bolt upright. She looked at the teacher who gave her a disapproving look and then she looked at Lauren who gave her a slightly strange look. Did she know what was going on? How could she though... the headmaster surely wouldn't have told her.

The lesson finished and Jessica packed up her school bag and set off to the headmaster's office. She had to walk across the main car park to get there as for some reason which Jessica had never understood it was situated on its own in a separate building which backed on to the boiler room and the gymnasium.

Under normal circumstances Jessica would be worried that all the other people in the classrooms which overlooked the car park would be able to see her making her 'walk of shame' towards the headmaster's office. But today she was more worried about what was going to happen when she finally arrived.

She walked through the outside door of the building and felt a jolt as she saw the headmaster's secretary sitting outside the office at her desk. Jessica approached nervously and Helen smiled at her and picked up the phone to tell her superior that 'she' was here. Jessica looked at the nameplate on the desk, it read 'Helen Grey'. She replaced the phone and told Jessica to sit down in the chair opposite her desk until the headmaster came to fetch her.

Jessica sat on the rather uncomfortable reception chair and tried to stay calm. She looked over at Helen to see if she could glean any information from her, but she was looking down at her desk reading some sort of report and did not make eye contact.