This story was written in 2000, I only had a physical copy so had to transcribe it from the original. Along the way, of course, I rewrote substantial sections, but kept the story intact. It's not my best story, I know... in a way it pleases me to read the original back because it shows how much I've improved over the years. But the reaction on Literotica has been largely positive, so I feel like I haven't wasted my time. I do have more old stories in hard copy, though none as long as this one, but my next story will definitely be all new, though I can't say more than that because I'm juggling several at once at the moment.
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!
*****
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.
Eventually the office door opened and the headmaster poked his head around to call her in. The headmaster liked making people wait for him, it always made them feel nervous and gave him the upper hand in most situations.
Jessica nervously picked up her bag and walked slowly into the headmaster's office. She looked round to see if Helen would follow her in, but she remained seated and still apparently reading her report.
The headmaster told Jessica to sit down, then he sat down behind his desk and looked straight at her. God he wanted to fuck her. His cock felt so hard right now and he just longed to feel her tongue curl around it. She looked so timid and defenceless, that's what he really liked. Helen was a great fuck, she was a right horny bitch and he loved screwing her however he pleased, but there was no challenge, or more rightly no genuine 'submission'. When he fucked her in the ass he knew she wanted it just as much as he did and where was the fun in that? He knew that most men would kill for a woman like Helen, but maybe he'd been spoiled. He looked into Jessica's eyes and tried to concentrate, which was hard enough given the state of his cock.
"Jessica, I spoke to your father last night," he began and Jessica tensed nervously.
"We had quite a little chat about you. I must tell you that your father was most pleased to hear about your outstanding work in your first term here at Maverley Park. I told him that lately you had made great progress and should turn out to be a great asset to him one day."
Jessica looked confused but relieved.
"You see Jessica, I told you I wanted to help you and I do. Now I have something here that you might like to take a look at."
The headmaster turned around in his chair and turned on the old television in the corner of his office. He pointed a remote at the VCR next to the TV and a video began to play.
Jessica peered at the images, the recording quality was not brilliant and there was no sound, but the images were clearly taken from yesterday's meeting. She tensed as she remembered that occasion once more. She looked up at the corner of the ceiling and spotted the security camera she had not noticed yesterday. Now it became clear why 'Helen' had sat where she had as she was not in the shot at all.
Jessica turned towards the headmaster to see him smiling at her. He waved his hand towards the television, clearly gesturing that she should continue to watch. The video lasted no more than a couple of minutes and to Jessica at least it had clearly been edited somewhat. It culminated with the headmaster leaping from his chair and ordering Jessica out of the room.
When the screen clicked off Jessica turned back to face the headmaster, who was looking at her with a Devilish look in his eyes.
"So Jessica, what do you think your father would make of that?"
Jessica sat dumbfounded, why on earth would he want to show this video to her father?
Then the truth dawned on her, and she now clearly understood why the headmaster had reacted as he had. The video is it appeared now clearly showed her undoing her shirt in front of the headmaster and then moving around the desk before dropping to her knees...
Jessica's face paled as she realised she had been set up perfectly. Even the fact that the headmaster's secretary had been in the room at the time had made her feel a little less guarded, a little safer, but if she appeared in the video it would look wrong. Now it appeared that she had been alone in the room with the headmaster and when confronted with evidence of wrong-doing (the tale of the girl in the back field no doubt) she had guiltily tried to worm her way out of it by offering the headmaster sex.
He had of course been a little weak, but in the end had come to his senses and shouted at her to leave his office. What else could he do? If anyone had walked in with her half-naked and on her knees he would have been the one in trouble, it was perfect. That he had let it go as far as he did only showed that he was human, and besides it had to go far enough to be damning.
Jessica really didn't know what to think now. But she was smart enough to know that headmaster had her over a barrel. Had the headmaster really spoken to her father? Surely if he had told him what he'd said he had then how could he be mad at her... but what if he hadn't? And there was still the video, she could never explain that away. She was trapped, and she knew it.
"What do you want from me?" Said Jessica meekly.
"Ah Jessica, you are at least clever enough to know when you are beaten, that will serve you well in later life..."
Beneath the desk the headmaster stroked his straining cock through the material of his trousers. He loved this point in a fresh girl's initiation. He loved the feeling of power as he watched them squirming, knowing that he had them exactly where he wanted them, and wondering exactly what that meant.
"Well Jessica my dear, I suggest you begin by finishing now what you started yesterday."
He looked at her intently, aching to see her full tits once again. His cock strained harder against his trousers as he looked over at Jessica, her hesitant fingers poised over the buttons of her shirt.
"Come on Jessica, don't keep me waiting. I want to see your beautiful tits again. You have no idea how hard it was for me to follow the plan yesterday, I could so easily have bent you over the table and forced my cock inside you... but patience brings its own rewards Jessica, and I want mine right now."
The headmaster turned his chair to the side and released his thick prick from his trousers. Jessica stared at it almost in shock. She had never even seen a cock in real life before and here she was about to be forced to do God knows what with it.
She looked at it again, she couldn't believe the size of it. She imagined it wasn't much longer than normal but it looked far too thick to fit inside any woman, let alone her tight virgin pussy.
The headmaster motioned for her to stand up and come nearer. Jessica hesitated again and the headmaster began to lose his patience.
"Jessica, get up and get over here right now you little slut. I know you want it, don't try and pretend you don't. You rich girls are all the same, you all act so innocent but when it comes down to it you all love getting fucked by a big, thick cock."
Despite her reservations, Jessica actually felt the beginnings of something she knew she shouldn't be feeling. Her stomach felt light and her hands were shaking as she finally pulled herself from the chair. She still hadn't revealed her breasts, in fact only two of her buttons were now undone.
"That's it Jessica, you're going to be just fine."
Jessica rounded the desk and stood before the headmaster, she looked down at his rearing shaft and gently bit her lip. The headmaster's patience was wearing thin now and he reached out and grabbed her shirt, yanking it open and dislodging a couple of buttons which fell to the floor.
Jessica gasped as her shirt was ripped open and she instinctively made to cover herself with her arms. The headmaster gently but firmly batted them away then gazed at her soft-skinned stomach and felt the ache in his balls grow even more intense. He reached out again and pulled the cups of her bra down and then let them go so that they pushed her full tits upwards and out, making them look even more enticing than they already were.
"Beautiful," he said as he reached down and started stroking his meat.
Jessica watched as he stroked his hand up and down the shaft and felt slightly light-headed as she wondered how it would feel to touch it herself.
"On your knees girl," barked the headmaster as he tugged at her shirt, pulling her down to the floor.
"We can do each other a lot of good you know, I'm going to teach you a lot about yourself and later in life you'll thank me... even if you hate me now."
As he said this he put his hand on the top of her head and pushed it down towards his burning cock. Jessica nervously traced her tongue around the tip and the headmaster shuddered with pleasure.
"Good girl, that's it... I knew you would be a natural, you rich girls always are. I suppose it's the easiest way to get what you want isn't it? I've heard of girls your age sucking off their father for a skiing holiday."
The headmaster gently pushed the back of her head once more and Jessica finally opened her mouth as wide as she could as she started to take his cock his cock between her lips. The silky texture of her mouth drove him to the brink, but he managed to hold himself at bay for a while longer.
With a bit of guidance from the headmaster, Jessica's head began to slide up and down his shaft and warmth of her mouth made a fantastic contrast to the cool air that circled around his wet prick when she rose to the tip. He knew he couldn't last much longer and soon his hips started to grind as he felt his spunk rising. Jessica instinctively tried to pull her head away but the headmaster had done this many times before and held her head firmly as he exploded into her mouth.
Jessica only swallowed what she had to and the rest dripped from her lips and onto his cock and balls.
'Lick that up!' He commanded. 'You'll learn to swallow, I'll make sure of that.'
Jessica reluctantly leaned forward and dragged her tongue along his cock, tasting his slightly bitter cum on her tongue and trying not to think too much about what she was doing. For his part, the headmaster loved the feeling of a tongue around his cockhead after he had cum, and the fact that this one belonged to such an innocent little slut only heightened his pleasure.
"Did you enjoy that?" He asked, sarcastically.
"No!" Jessica spat.
"Pity... because I foresee a lot of cocksucking in your future."
He reached down between her legs and she instinctively clenched the muscles in her thighs. The headmaster gave her a warning look and she relaxed slightly, just enough to allow his fingers to slide a little way between them.
"It's funny," he said. "Considering you didn't enjoy it, your pussy seems awfully wet."
Jessica blushed, furious at her treatment but already his fingers were working their magic and she felt herself surrendering even as she opened her mouth to protest.
"I hate you," she hissed.
The headmaster ignored her words, and continued stroking her pussy through the moist material of her knickers. Despite her best efforts Jessica felt her muscles loosen as she unconsciously spread her legs a little wider, offering him better access. Encouraged by her willingness the headmaster slid her knickers to one side and gently inserted a finger into her tight, wet pussy. Jessica weakly tried to push him away but the headmaster persisted and Jessica sighed loudly as she felt his fingers gently swirly inside her.
"Relax Jessica, you can't tell me this doesn't feel good... can you?"
Jessica couldn't deny her growing arousal, but she wasn't about to give in to the headmaster easily. She gripped his arm again and tried once more to remove his hand from between her legs.
"Oh Jessica... I see you still have a little spirit, perhaps I need to be a little firmer with you."
The headmaster pulled his hand from between her legs and raised the sodden fingers to his mouth, then looked her straight in the eye as he licked her juices from each digit.
"Absolutely delicious," he complimented her.
Abruptly he stood up and grabbed Jessica's arm. He marched her back to the other side of the desk and then stood her in front of it facing his chair.
"I think it's time you learned some hard lessons."
He placed his hand in the middle of her back and pushed her firmly down until she was flat on his desk, her ass sticking out and awaiting his attention.
"You know Jessica, I am very disappointed in you. I guess nobody has ever told you that you should keep sucking until you have swallowed every drop of a man's cum. Well I'm telling you now. In future, when you suck my cock, you keep sucking until I tell you to stop. If I decide to cum on your face or tits then I will pull it out myself, do you understand?"
Jessica didn't like the sound of 'in the future' one bit, but she slowly nodded her head.
"Don't nod your head at me you little bitch, you answer me properly."
"Yes, Sir."
"That's better."
The headmaster reached down and lifted the hem of Jessica's skirt, placing it over her back. He looked down at her sodden, white knickers and smiled at her obvious arousal, his cock already stirring once more.
"What a beautiful backside you have Jessica," he said as he rubbed his palm over one of the cotton covered cheeks. "I'm going to have a lot of fun with that."
Jessica shuddered, but felt her pussy grow wetter still as he touched her ass.
"Spread your legs girl."
Jessica reluctantly moved her legs a couple of inches apart.
"Look Jessica, if you want to make this harder on yourself that's you problem, but if you know what's good for you you'll do as I say, when I say. Now spread your fucking legs."
Jessica moved her legs further apart, but the headmaster still grabbed her thighs and moved them a little further apart.
"And don't you dare move them back!"
Jessica was not quite so scared of the headmaster now, she was more scared of how she felt in herself. His treatment of her was degrading and yet her pussy was soaking wet. Was he right about all rich girls being sluts?"
The headmaster stroked the backs of her thighs for a moment, studying her prone form as his cock, still protruding from the front of his trousers began to harden properly. He wanted to fuck her, but he also desperately wanted to punish her cute little ass.
He stroked her ass again, then his hand found its way to the edge of the material and he pulled it upwards slowly. Jessica gasped as she felt the cotton pull tighter and move up between the lips of her pussy and the cheeks of her ass.
"Feels good doesn't it Jessica, a bit of friction around your pretty, young pussy..."
Jessica felt some minor discomfort but she couldn't deny that she was getting wetter by the second.
"Well I don't want you to enjoy this too much, so I think it's time for you to be punished."
The headmaster removed his hands from her body and she felt a chill of fear course through her as she heard him slide his belt through the loops in his trousers.
"Please don't..." begged Jessica. "Please, I'll suck you again if that's what you want, but please don't use your belt on me."
The headmaster placed his belt on the desk, right where Jessica could see it, then leant closer and whispered in her ear.
"I'll do whatever I want to you Jessica, but don't worry, I'll warm your ass up with my hand first... believe me, it will make it easier for you in the long run."
Jessica groaned her displeasure but the headmaster took no notice. He placed his hand on her now almost naked ass and rubbed it in a circular motion for a few seconds. Then he pulled his hand away before bringing it down with a stinging slap on Jessica's right cheek.
"Oooow!" yelped the girl loudly.
The headmaster's cock twitched and he circled it with his left hand and started to rub as he lifted his right hand once more and brought it down on her other cheek.
"Oooooooow!" wailed Jessica.
The headmaster slowly increased the intensity of her spanking, until he was randomly hitting both cheeks and starting to move to the tops of her thighs. One slap caught her in a particularly sensitive part of her inner thigh and she jumped a little and moved her legs closer together.
"What did I tell you about keeping your legs apart," he barked.
"I'm sorry Sir, I couldn't help it..."
The headmaster grabbed a wooden chair from the corner of the room and pushed the feet between her feet, effectively spreading her legs and keeping the spread.
"That should keep your legs where I want them girl."
He slid his hands over her nicely warmed arse and down between her legs. His fingers slipped along the lips of her warm pussy, which was still separated by the sodden white cotton of her panties.
"Ha, you may protest you don't like it, but your pussy clearly does. Just another rich girl slut for me to play with..." His victorious tone irritated Jessica still further, but she couldn't help but ache for him to touch her pussy again.
He worked his fingers alongside the material and slowly curled them between Jessica's lips. Jessica groaned with pleasure as his fingers softly stretched her wet, pink flesh. The headmaster's other hand pumped his cock faster as he pleasured her but he tempered his enthusiasm as he didn't want blow his load just yet.
He removed his fingers from her slick hole and made a great show of picking up the belt from the desk.
"I think your arse is warmed enough now Jessica, as I'm feeling particularly generous I will allow you to rub your clit while I punish you. I'm sure you don't need any encouragement to do that at night in your bed, so there's no need for you to feel embarrassed about doing it now. Besides, it might take the edge off the pain..."
Jessica made no move to take up his offer and the headmaster shrugged his shoulders.
"Suit yourself, I won't always be so kind to you... I would advise you to take advantage when the opportunity arises."
As he said this the headmaster wound one end of the belt around his right hand and swung it through the air a couple of times. Jessica tensed as she heard the leather belt whistling through the air and prepared herself for the worst.
After a couple more practice swings the headmaster finally brought the wide leather belt down across the cheeks of Jessica's ass.
"Ooooooooowwwwwww!!" shrieked the girl.
The headmaster wondered whether Helen had reached orgasm yet. He knew full well that she would be listening in from her desk outside the door and rubbing her clit beneath the desk as she did so. The headmaster liked to keep Helen in her place and so would occasionally refuse her permission to join in some of his teacher-pupil sessions.
He knew that Helen was (amongst other things) particularly fond of watching young girls being spanked, and to miss out on this session would frustrate her no end. He loved the power trip, but he would make sure she came hard later that evening once the school had closed.
The headmaster returned his attention to Jessica once more. He raised his arm again and laid a steady barrage of strokes across her cheeks. With each contact Jessica cried out louder and louder until the headmaster began to wonder if it would be necessary to gag her. His cock strained as he thought of ripping off her knickers and shoving them into her mouth, but then he decided on a better course of action.
Jessica wondered how much more she could take, each time the belt caught her skin it was like a bolt of electricity coursing through her body. The initial pain transforming into a warmth that always seemed to spread down between her legs to her aching, sodden pussy. Jessica longed to touch herself, the headmaster was right about that, but she was damned if she was going to let him see her do it.
Jessica was amazed at how much the pain was turning her on, even though her ass felt like it was on fire and her eyes were filled with tears. She felt completely humiliated bent over the desk with her legs spread, how could she be so hot when she was being degraded so badly?
The headmaster laid the belt on her arse a further four times, wanking his cock as he did so. He knew he couldn't last much longer, as much as he wanted this to continue. He looked down at Jessica's angry red cheeks and almost felt a little sorry for her. She had definitely had enough for one day and he dropped the belt on the floor as he started to concentrate more on his impending orgasm.
He pulled the chair out from between her legs and grabbed the girl roughly. He shoved her down onto her knees and jerked his straining cock inches from her face. Jessica's relief at the end of the beating was obvious and she struggled to hold herself upright.
"Okay you little slut... this time you're going to do it properly aren't you, or would you rather I put you back over the desk for some more?"
"No," pleaded Jessica. "I'll do it, I'll do it properly..."
"Good girl," sighed the headmaster as he slid his cock between her lips for the second time that afternoon.
Jessica felt his hands grip her head as the smooth head of his cock slipped into her mouth. The headmaster wasn't merely content for her to suck him this time, he wanted to fuck her mouth and cum in her throat. Fortunately for Jessica he was so close before he entered her that after a few strokes inside her wet, velvety mouth his body started to shudder and his cock began to spurt before he had a chance to skull-fuck her properly. But still she found herself gagging as his cock hit the back of her throat as it dumped it's second load of the day inside her mouth.
Jessica was caught by surprise and some of his cum slipped out of her mouth and down onto her uniform. She quickly wiped it off with her finger and hoped he wouldn't notice, the last thing she needed was to be punished for ruining her shirt.
The headmaster pulled his wilting cock from between her lips and milked the last remaining drops of cum onto her tongue.
"That was much better Jessica, in time you'll learn to take my cock as hard as I can give it. But now, as much as I'd like to have some more fun with you... I suppose I had better let you get to your next lesson. But before you go, do want to cum?"
Jessica shook her head, even though she desperately wanted to cum. The headmaster chuckled to himself... "What did I tell you about answering me properly, do want to be punished, is that it?"
"No, Sir..."
"No you don't want to be punished or no you don't want to cum?"
"Both, Sir."
Now it was the headmaster's turn to shake his head. He refastened his trousers and helped her to her feet. Jessica smoothed down her skirt and tried to regain her composure a little. Her ass was still burning and the taste of the headmasters cum lingered in her mouth. The headmaster sat down at his desk and picked up some papers, which Jessica took as her cue to leave.
"Oh and Jessica, I'm sure I don't need to tell you that what happened here is to stay private. To be honest, no one's going to believe you anyway and I'd hate to have to ring your father back and tell him I had you all wrong."
Jessica nodded and then opened the door to leave. It wasn't until she was half way back across the car park that she realised that her knickers were still pulled up hard into the crack of her ass and tormenting her burning clit...
--- ---- --- --- ----
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.
-- -- -- -- -- -- -- --
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.
The headmaster pulled away from Helen and left her kneeling on the floor. She continued to rub her pussy as she watched him move over to where Jessica sat with her legs spread and her pussy exposed to the pair of them.
The headmaster looked down at her and she found herself looking into his eyes as his rock hard cock bobbed just inches away from her. Part of her wanted to reach out and touch it, but she was too nervous and unsure to do so. Instead she continued pleasuring herself, her fingers rubbing her clit as she waited for his next instruction.
"You look so innocent Jessica, and yet... underneath it all, you're just another horny.. little.. slut."
Jessica let out a tiny groan as he spoke and her chin trembled slightly.
"What are you Jessica? I want to hear you say it."
"I'm a horny little slut..." she gasped.
He smiled and corrected her.
"I'm a horny little slut, Sir!"
Jessica repeated his words and he smiled wickedly.
"I wonder if you've learned anything yet..."
He grabbed his cock and moved forward, pushing his cock between her lips and filling her mouth with his throbbing, hot meat. He watched as Jessica struggled with the new sensation, allowing her to go at her own pace, wanting her to enjoy her first taste of cock. He looked over his shoulder at his abandoned secretary, clicked his fingers and pointed to the floor between the girl's widely spread thighs.
"Get down here and lick her slut."
Helen almost leapt across the room, such was her eagerness to taste the pure, virgin pussy she was being offered. She sank between the girl's legs and pushed them slightly further apart, grabbing the girl's fingers and licking them clean before she lowered her head and began to put her eager tongue to good use.
Jessica found the idea of another woman licking her pussy disgusting, but as Helen's skilful tongue teased and pleased her pussy she slowly forgot her inhibitions and found herself squirming against the pleasure giving muscle between her thighs. Encouraged by her actions, Helen took it upon herself to slide first one, then two fingers into the girl's tight virgin hole.
"Do you like having your pussy licked Jessica? I think you do... I think you like it a lot.
Maybe if my secretary is very good, I will allow you to lick her hot, sticky cunt later, would you like to lick her pussy and make her cum?"
The look in Jessica's eyes betrayed her repulsion and he smiled to himself as her continuing naivety and innocence displayed itself for his amusement.
Eventually Jessica closed her eyes and concentrated on trying to please the cock that filled her mouth, at the same time enjoying the sensations that Helen was providing between her thighs. As the pleasure built more and more she let the headmaster's cock slip from her mouth as her body slowly tensed and then exploded as she came hard on the other woman's tongue.
As she recovered from the exertion of her orgasm, Jessica opened her eyes to find the two of them looking at her intently.
"So, being licked by another woman isn't so bad after all then..." stated the headmaster sarcastically.
Jessica said nothing, now that she had cum she suddenly felt ashamed of her slutty behaviour and quickly closed her legs, trying to hide her sodden pussy from view.
The headmaster reached down and helped his secretary to her feet, then kissed her hard on the lips, tasting the young girl's juices as he slipped his tongue into her mouth.
"Delicious," he said and smiled at Helen before he turned his attention back to Jessica, who was already in the process of pulling her skirt down and trying to regain some sense of decorum.
"And what do you think you're doing?" Enquired the headmaster. "I haven't finished with you yet!"
He reached out his hand and Jessica stood up to take it. His fingers closed around hers and he lead her over to the desk. Once there he lifted her up and told her to lie down.
Jessica lay back, and as he pulled her legs back towards him so that her arse was almost on the edge of the desk, Helen was removing her clothes and tossing them aside until she stood naked bar her black, seamed stockings. As she watched the headmaster arranging the girl as he wanted her she couldn't help but tease her pussy with her fingers and then taste herself once more.
The headmaster lifted Jessica's skirt, then slid her knickers down her legs and off over her feet. He placed them on the desk next to her and then started to push Jessica's legs apart. She resisted at first and he pushed harder, his strength gradually overcoming her resistance.
"All you have to do is say the word and we'll stop right now Jessica... but you know what will happen if you do, don't you?"
The thought of her father being called and whisking her away to the dreaded Catholic school made her surrender and she relaxed the muscles in her legs. The headmaster pushed them wide, exposing her wet, slippery pussy and moved forward to position himself at the entrance to her inviting hole. He grabbed his cock and gently teased her lips and clit with the head, savouring the first moments of her deflowering. Despite herself the sensation sent a shiver through Jessica's body and she found herself moving in time with him, desperately craving more friction and pleasure and ultimately to feel him inside her.
He grabbed her sodden panties and thought for a second about gagging her, he didn't want the place screaming down when he took her virginity with his large cock, but then he had a better idea.
"Helen, get up here and sit on her face," he half whispered.
Helen was on the desk like a shot and before Jessica realised what was happening the other woman's pussy was being lowered onto her mouth.
"No.." protested Jessica as she turned her head away from Helen's dripping slit.
The headmaster eased the tip of his cock into her tight teen cunt.
"You have to learn to give and take Jessica, and if needs be I will beat that lesson in to you."
The headmaster pushed deeper, feeling the girl's incredibly tight pussy contracting as he forced himself inside her virgin hole. Jessica groaned into the secretary's hot, wet pussy as she struggled to accommodate his throbbing meat. The headmaster loved nothing better than the feeling of a fresh, tight cunt surrendering to his cock, though he'd taken countless girls by now it was a feeling that never got old.
"Get that tongue moving Jessica, unless you want me to use my belt on you again."
Jessica's body tensed and strained as the headmaster's cock stretched her poor virgin pussy wide open. Her half-hearted, stop-start pussy-licking was ineffectual, but Helen was still aroused by the feeling of her pussy being teased by the young girl and the sight of her lover defiling her innocent body. She reached down and pulled the girl's shirt open, exposing her pale skinned belly and then pulled her bra up roughly until her soft tits sprang free.
The headmaster reached up and squeezed them as he continued fucking Jessica's sweet cunt, his pace quickened and he drove his cock deep and hard into the young girl, all too aware that he couldn't hold on much longer. At the last second he pulled out and pumped it hard with his hand, releasing a huge load of cum which erupted all over Jessica's stomach and tits. Jessica felt the cum landing on her skin and gave up the pretence of attempting to lick Helen's pussy completely
Helen leaned forward and greedily licked her lover's cum off the girl's body, as she did she moved back slightly and Jessica was spared the sight of the older woman's pussy dripping onto her face.
"You will learn a lot from Helen," said the headmaster. "But like many things in life, there's an easy way and a hard way."
As he spoke he idly fingered her wet, stretched pussy
"So Helen, how would you rate little Jessica's skills today?"
"Awful," smiled Helen. "She barely even tried."
It was clear to the headmaster that Helen was looking forward to seeing the girl punished.
"Oh dear, lack of experience I can forgive, but selfish disinterest I can't abide. You realise of course that it will be necessary to punish you... and I think, as it was Helen who suffered your unwillingness to perform, that she should decide your punishment."
Jessica's heart sank. What kind of perverse punishment would that crazy, sex-mad bitch come up with?
Jessica tried to hide the huge grin that was threatening to engulf her face, she was delighted to be consulted but she knew her options were limited at the moment. What she really wanted to do was slip into her largest strap-on and plough the girl's tight ass, but she knew the headmaster wouldn't allow it at this early stage.
"I think the little slut should be caned," she said after a few moments thought.
Jessica gasped in fear as the memory of her first caning returned.
'Not very imaginative' thought the headmaster, but an adequate punishment under the circumstances.
"Okay Jessica, get up and lean over the desk."
"No, over the chair like befor..." started Helen.
The headmaster glared at her as Jessica lifted herself up and stood between them on the floor.
"Over the desk," repeated the headmaster firmly as he turned to retrieve his cane from the wall, just as he had the last time. Helen was really making a rod for her own back today.
"Please, don't cane me... I'll do it properly if you want me to, please," begged the girl.
The headmaster held the cane in his fingers, twirling it as he enjoyed her obvious discomfort.
"I'm sorry Jessica, but you need to learn to do as you're told... and you need to learn to do it, or at least try to do it, without being told twice."
"But..."
"I'm sorry Jessica, but unless Helen is in a forgiving mood, I'm afraid you'll just have to take your punishment."
The two of them turned to look at the secretary, but Helen was never going to give an inch.
"Cane her," she hissed.
The headmaster shrugged and tapped the cane on the desk. Jessica slowly lowered herself over the desk and felt the headmaster lifting her skirt up and out of the way once again. He looked over his shoulder and saw Helen sitting in a chair, her legs spread wide and her fingers working her clit as she enjoyed the sight of her lover preparing the girl for her punishment.
He turned his attention back to Jessica, all too aware that any second now his secretary would be forcing at least one finger into her own ass as she brought herself closer to orgasm. He placed the cane across Jessica's cheeks for a moment, before swiftly lifting it and slamming it down onto the girl's flesh.
Jessica howled in pain and he snatched up the girl's knickers from the desk where he had laid them earlier. In a flash he grabbed the girl's jaw and pushed the wet ball of cotton between her lips.
"You have to learn to keep quiet girl!" He snarled.
He glanced over at Helen, who was now indeed fingering her ass as she watched on, and clearly not too far away from cumming.
"Dirty bitch," he muttered to himself before turning back to Jessica again.
He looked down at the one red stripe that currently decorated the girl's cheeks, then ran the tip of the cane down the crack in her ass before letting it slide back and forth against her pussy lips a few times. He rested the cane parallel to where the first blow struck and Jessica waited nervously for the next searing blow to arrive. The waiting was almost as bad as the actual strokes, and the headmaster strung it out now as he listened to Helen's rapid breathing and moaning behind him.
He firmly placed his hand on Jessica's back to keep her still then laid three quick, hard strokes across the girl's cheeks. Jessica screamed into her panties, while on the other side of the room Helen screamed in ecstasy as she took herself over the edge and her body convulsed through a huge orgasm.
The headmaster placed the cane on the desk and removed the panties from the girl's mouth.
"I hope you have learned something here Jessica."
"Yes Sir," she murmured, struggling to get the words out as she wiped the tears from her eyes.
"Good, you may go now."
Jessica got herself together and left them alone in the office. The headmaster retrieved his shorts and trousers and dressed himself as he looked down at the exhausted, motionless form of his secretary
"I think you should spend an afternoon alone with her," said the headmaster. "Teach her how to eat pussy properly, her innocence is endearing but we need to bring her on or we will run out of time."
Helen nodded in agreement, her eyes still half-closed as sat up and tried to collect herself.
"And you... I think it's time you were taken down a peg or two as well, barging into my office like that, who the fuck do you think you are?"
Now it was Helen's turn to look at the floor.
The headmaster went to his drawer once more to retrieve the leather covered box. He selected a heavily contoured dildo from the box and smeared it with some kind of gel. He walked back over to Helen and told her to get down on her knees. She complied immediately and the headmaster quickly and roughly parted her cheeks before forcing the dildo deep into her ass.
The gel was hot and within seconds Helen's arse was on fire. The headmaster watched in amusement as she struggled and writhed below him. He reached down and grabbed the base of the dildo, turning it inside her before pulling it out and slamming it back in again. Helen felt some of the gel slither down between her legs and start to heat up her pussy, she reached back and tried to brush it away but all she did was work it into the skin and make it more effective.
The headmaster knelt down beside her and rubbed his hand across her arse cheeks.
'Time for a good old-fashioned spanking' he whispered as he lifted his hand and slammed it down again.
Helen had been spanked a thousand times before, but never with her ass burning from the inside out. The headmaster spanked her backside until his hand was numb and her cheeks were crimson red. Beneath him Helen was snivelling into her forearms as she struggled to cope with her punishment, but she knew as well as he did that she wouldn't have it any other way. He toyed with the dildo some more before getting up, walking back to his desk and putting the box away again.
"Get dressed," he said. "And leave that dildo in for the rest of the day. I'll be checking on you later."
Helen dressed awkwardly and scampered out to her desk, it was going to be a long afternoon.
--- --- --- --- ---
Jessica was next summoned to the headmaster's office a few days later. She arrived slightly early and waited outside for a short time before entering the reception area. No one was at the desk so she sat down in one of the reception chairs to wait. Eventually, after she had waited about ten minutes, she decided to try knocking on the headmaster's office door. A voice called out to her to enter, but it wasn't the headmaster's voice, it was his secretary, Helen. Jessica opened the door to see the woman sitting behind the headmaster's desk.
"Oh...err, where is the headmaster?" Enquired the girl.
"We... won't be needing him today Jessica," smiled Helen. "I will be calling the shots this afternoon."
Jessica almost wished the headmaster was here, especially when Helen stood up from the desk to reveal that apart from her shirt she was completely naked. The older woman rounded the desk and walked towards her and taking her school bag from her hand.
"We won't be needing that either," she said, dropping it into a nearby chair.
Helen walked over to a large, rather ornate sofa that hadn't been in the office on Jessica's previous visits. She sat down on it and lay back, spreading her legs as she did so. There was a cushion placed on the floor between her legs and she told Jessica to come and kneel on it. Jessica wondered what would happen if she left, but soon decided that once Helen told the headmaster about it she would be in even more trouble.
"In case you're wondering," began Helen. "This was the headmaster's idea, and he won't be very impressed if you don't co-operate. You've already been punished for your selfish behaviour, do you really want to be caned again so soon?"
Jessica most certainly did not, her arse was still a little sore even now, and she didn't relish a repeat of that in a hurry.
"No, I didn't think so," said the other woman, as she registered the look on Jessica's face.
"So get over here right now!"
Jessica walked over to where Helen lay and reluctantly sank to her knees.
"Today I am going to teach you to pleasure a woman properly... with your mouth."
Jessica's face curled in disgust and Helen had to fight the urge to slap her straight across the face.
"That attitude isn't going to get you anywhere, and if you don't co-operate I'm going to make sure you leave this office with more than a sore arse."
If Helen had her way Jessica would leave this office with a very sore and very stretched arse, but she knew the headmaster would punish her severely if she went too far too soon. She leaned forward and grabbed the girl's head, then pulled it down between her thighs.
"Now gently lick all around my lips," she ordered.
Jessica gently licked up and down Helen's already very wet lips, trying to think about something else to take her mind off what she was being forced to do. Helen meanwhile was enjoying her attentions and occasionally pushed her mound forward towards to try and create a little more friction between them. After some time, Helen instructed the girl to push a finger inside her, which she did rather carelessly and caused the older woman to wince in discomfort.
"Careful!" Warned Helen as she gently slapped the girl on the side of her head. "Now tease my beautiful pussy with it as you lick me."
Jessica continued with her task for a while and then she felt a hand on her head guiding her tongue upwards towards Helen's clit.
"Mmmm, that's better," moaned Helen.
Helen kept Jessica between her legs for quite some time until she eventually came, pressing the girl's head between her legs as she did so. When she eventually caught her breath she let fly with her opinion.
"Well, you got there in the end, but it wasn't exactly brilliant. I think I shall have to talk to the headmaster about some regular tuition if you're ever going to reach the standards necessary to graduate from this school."
Jessica's face fell, the last thing she wanted was to be stuck licking Helen's pussy every week for the next two years, or however long she was supposed to stay here.
"Oh dear," teased Helen. "It looks like Princess Jessica isn't pleased by that idea. You aren't learning very fast are you girl?"
Jessica scowled at her tormentor.
"No, I just don't want to lick y..."
"I don't care what you want. And neither does the headmaster. You are here to learn... and now it seems I must teach you yet another lesson."
Helen got up off the sofa and went to the desk. She pulled out the leather box and removed the cuffs, a joining bar and a whip. She walked back over to Jessica and told her to put her hands behind her back. Jessica refused at first, but Helen grabbed her arms and pulled them back behind her and then fitted the cuffs. Then she joined the cuffs together with the bar and pushed her back down onto her knees.
"I don't remember telling you to get up either Jessica, you are a very difficult girl, and difficult girls have to be punished - it's the only way they learn."
Helen shoved her hand under Jessica's skirt and between her legs, once there she rubbed the girl's pussy vigorously. She continued until she felt the material become damp and laughed in the girl's ear.
"You can stop pretending you're not turned on now Jessica, your body will always betray you."
Jessica said nothing, but little out a tiny moan of pleasure.
"See there's no reason to pretend now is there?"
Jessica did not speak and Helen grabbed her jaw and turned the girl's face to hers.
"Is there?"
"No," replied Jessica.
"No, what?" Persisted Helen.
"No... Miss," spat Jessica.
Helen smiled at her and kissed her full on the lips, tasting her own juices there. Jessica pulled back and Helen gave her a warning look. She looked directly into the girl's eyes as she reached up and tore the girl's shirt open, then pulled her bra down to release her youthful tits. She let go of the bra and it sprang back and caught underneath, pushing Jessica's breasts up and forward.
"Did you enjoy making me cum?"
"No," insisted Jessica.
"Wrong answer," countered Helen.
Helen reached under her skirt again and roughly massaged her pussy until the girl's breathing became heavy and rapid. Continuing this, she bent down and sucked and licked the younger girl's nipples until they were rock hard. Once satisfied, she pushed Jessica's shirt back and down her arms slightly and addressed her again.
"Do you know what I'm going to do to you know girl?"
Jessica looked worried but did not respond.
"I'll tell you...in a moment, I'm going to whip your pretty little tits. Maybe that will teach you to be a bit less selfish in future."
"No please, please don't do that... I'll be good, I'll do whatever you want..."
Helen wasn't about to be dissuaded however and the girl's pathetic pleading was only serving to make Helen more irritated with her.
"In fact Jessica, you are going to beg me to do it, unless you would like a more severe punishment?"
Helen leaned in closer and whispered the next part for greater impact.
"Perhaps you'd rather have a nice big, hard dildo shoved inside your tight little arse?"
Jessica squirmed at the thought and Helen grabbed her hair and looked her straight in the eye.
"Well my little slut... I'm waiting, what's it going to be."
Jessica faltered for a second and then crumbled.
"Please Miss, please whip my tits. I am a bad girl and I need to be taught a lesson."
Helen smiled and gave Jessica's wet cunt another firm rub.
"That's much better... and your pussy is so wet, are you sure you aren't getting off on this?"
Jessica looked at the floor and Helen knew that part of her was. Then Helen took the small whip in her hand and began to whip the girl's soft breasts. It was a fairly soft leather whip, but when she swung it right it could still deliver a sting. Jessica cried out several times throughout her punishment, which was punctuated by Helen rubbing her pussy every so often to make sure she was still wet, and also to solidify the association between the pleasure and pain the girl was experiencing.
Eventually Helen decided that Jessica had had enough and dropped the whip on the floor. Jessica looked down at her sore, red tits and wondered how she ever got herself into a position where these people could do these things to her.
Helen began rubbing Jessica's pussy again and then worked her fingers inside the girl's panties and began to slide her fingers between the folds of wet flesh between her thighs.
"Have you learned your lesson Jessica?"
"Yes Miss," groaned the girl, she would say anything if it meant she didn't have to feel the whip again.
To test her somewhat, Helen lifted her pussy-soaked fingers to the girl's lips and waited for Jessica to lick them clean. Jessica submissively accepted the older woman's fingers into her mouth and used her tongue to clean them thoroughly.
"Good girl," said Helen as she lowered her fingers and pushed them back between Jessica's legs again.
Helen then reached behind the girl with her other hand and started to tease her pussy from both sides. Once they were both soaked through she moved her right hand higher so that it was concentrated on the girl's clit and soon she could tell the girl was approaching orgasm. She increased the intensity of her attentions and at the same time she moved her other hand back so that her sodden fingers where between Jessica's ass cheeks. As the girl started to shake Helen forced one finger into the girl's ass and immediately felt her muscles clamp hard around it as she came very hard.
Jessica didn't know what had hit her and if Helen hadn't been there to hold her up she would most likely have collapsed onto the floor. When Jessica finally stopped cumming, Helen removed her fingers from the girl's body, then carefully undid the cuffs and removed them from her wrists. Then she stood up and walked back over to the desk again and replaced the cuffs, bar and whip before closing the lid.
"Better get up Jessica, your next lesson begins in five minutes."
Jessica stood up silently and wobbled slightly as she made to adjust her clothes. Her tits were tender and her ass felt weird too, but she had to admit, she had never cum so hard in her short life. Was she as bad as they were, deep down? She didn't even want to think about it...
Despite this, for the next few days, when she lay awake in bed at night, she found her fingers drifting to her pussy and her thoughts returning to all the degrading things Helen and the headmaster had done to her... and each time she came her fantasies got a little more embedded and she started to crave their attentions, even though she still hated them.
-- -- -- -- --
The headmaster called Jessica in to his office, and as she walked in through the door she noticed Helen walking in behind her. The headmaster told her to sit down and Helen walked around the desk to sit next to the headmaster.
"Now then Jessica, Helen tells me that your performance the other day was... adequate, but nothing special."
"She whipped my breasts!" Countered Jessica.
"As well she might, in the circumstances..." said the headmaster. "In any case, I want you in here at ten twenty every Tuesday and Friday for the next three weeks. Helen will teach you to eat pussy properly and if she feels that she needs to whip your tits to get the message through then she has my complete blessing."
Jessica fumed at the thought of six more meetings with the 'Slut Secretary from Hell'. But what could she do?
"Anyway Jessica, down to business... stand up and take your skirt and knickers off.
Jessica stared obstinately at the pair of them.
"Now!"
Helen squirmed with delight as Jessica stood up and removed her lower garments. She already had her fingers in her pussy and couldn't wait to get started on the girl again.
The headmaster however, gave her a disapproving look, and she calmed down slightly.
Jessica didn't like the abruptness of the headmaster's tone, and he seemed to be in something of a bad mood today.
"Lean over the desk Jessica." Said the headmaster as he rounded the desk.
"What are you going to do to me now?" She moaned.
"You'll find out soon enough."
Jessica felt herself shoved down across the desk once more, and waited nervously to see what would happen next.
"You have a very nice arse Jessica, one day you'll make a good slut-wife for somebody."
Jessica opened her mouth to protest, but quickly thought better of it, and no sooner had she relaxed again than the headmaster began to spank her.
"But it will look even better with some colour to it," he said as he laid a volley of hard slaps on each cheek.
Then he knelt down behind her and pushed her legs apart, before grabbing her ass cheeks and pulling them open, exposing the girl's tight puckered hole. Jessica tensed, remembering how Helen had fingered her arsehole at their last meeting, but the sharp intrusion she was expecting never came. Instead, she felt the headmaster's warm, wet tongue flicking and pressing against her opening and as she relaxed and started to enjoy this new and unexpected sensation she felt her cunt flooding with juices.
Next she felt the headmaster insert a finger into her now sopping pussy and begin to pleasure her as he continued to tease and invade her arse with his tongue. After a while he removed his finger and stopped licking her ass, Jessica was quite disappointed as she had begun to enjoy the feeling and was at the very early stages of starting to orgasm.
The headmaster reached up onto his desk and grabbed the marker pen that was placed there, the one with the bullet shaped lid which he kept for exactly these occasions. As she watched him grab the pen, Helen sighed as she remembered her own initiation into anal pleasures so many years ago.
He pulled it down and placed the tip at the entrance to her pussy, sliding it in gently and ensuring it acquired a liberal coating of her juices before he withdrew it and pressed it gently against the entrance to her arse. He pushed it gently forwards and it slid fairly well, but after a few seconds he pulled it back and reached into his pocket. He pulled out a small tube of clear gel and applied some to the tip of the marker, before replacing it and pressing the marker pen between the girl's cheeks once more.
As the marker pen slid smoothly into her arse, Jessica realised it didn't feel half as bad as she'd been expecting. The headmaster, sensing her acceptance began to push and pull the marker in and out of her arse and then re-introduced his finger into her wet cunt, co-ordinating the two while Jessica learned to accept the double penetration.
Once Jessica was used to this, the headmaster pulled a smallish dildo from his pocket and pushed that into her pussy in place of his fingers. The girl seemed to be coping well and then, without warning he removed the pen from her arse and pressed the dildo inside her instead. The dildo wasn't that much bigger than the marker, but it felt it to Jessica and she cried out. The headmaster slapped her arse once again and berated her.
"Don't be so pathetic girl, Helen takes my cock up her arse all the time, and so will you before too much longer."
"No I won't!" Exclaimed Jessica.
The headmaster chuckled and continued to fuck her arse with the dildo.
"You'll do as you're told!" He snarled.
Eventually Jessica got used to the intruder in her arse and it became less uncomfortable. Meanwhile Helen had risen from her chair and removed her skirt and shirt. She opened a drawer in the desk and pulled out a harness which she proceeded to fasten around her waist. When she had finished Jessica realised to her absolute horror that the woman now possessed a rubber cock which was extending from between her legs. Helen moved around behind the girl and the headmaster pulled the dildo clean out of her arse. She suddenly felt very empty, but the sensation didn't last long as Helen forced the tip of her 'cock' into Jessica's tight arse and slowly forced it inside her.
Even though Helen had quickly smeared the strap-on with some of the gel from the headmaster's pocket, Jessica found it hard to take. It wasn't much bigger than the dildo the headmaster had used on her, and it certainly wasn't as large as a real cock, never mind the headmaster's impressive tool, but it still felt huge to the young inexperienced girl and she wailed as the strap-on reamed her tight hole.
"What's the matter Jessie, don't you like me fucking your arsehole?" Taunted the secretary.
"No you bitch," groaned Jessica.
This only spurred Helen on to fuck her deeper and harder, while the headmaster watched on, somewhat amused by their interaction. After a while he placed his hand on Helen's arm and whispered to her that it was 'enough'. Helen was slightly disappointed, but after one more hard thrust she undid the straps that fastened the cock to her and stepped away. Then she refastened the straps around Jessica's waist, leaving the rubber cock trapped inside the girl's well fucked arse.
Then the headmaster told her he was going to show her how a woman takes it in the arse and when he came around the desk he was naked with his impressive cock sticking straight out in front of him. Jessica looked terrified, but then she saw the headmaster sit down in his chair and his secretary move to climb on top of him. She was naked now as well, and she climbed on to his lap with her legs either side of his, facing him so that he could suck her tits as he fucked her if he wanted to. The position also gave Jessica an excellent view of what was about to happen and realising that she wasn't about to be impaled by the headmaster's huge cock she began to relax somewhat.
The headmaster grasped his cock and slid it easily into Helen's dripping cunt. Helen groaned loudly as she impaled herself on his length, holding onto his shoulders as she started to ride him hard. Jessica watched as the headmaster reached around and started to use his fingers to work some more of the gel into Helen's arsehole, and then suddenly he lifted her up slightly and slid his cock out of her pussy. He placed it firmly at the entrance to her arse and Helen sank slowly down onto it.
Helen gritted her teeth as she felt her lover's huge cock penetrate and stretch her. She consoled herself that this was nothing to what Jessica was going to feel when she was invaded by this monster cock, and she gritted her teeth while she became used to the headmaster's size. After a while she started to ride him faster, eager to prove herself to both her boss and their pupil. The headmaster sucked and bit her tits as she worked his cock with her ass and after a while Jessica sensed that the performance was rising to a climax.
"Ah, fuuuuck!" Moaned the headmaster as he felt himself nearing the edge, then spilling over it and pumping rope after rope of hot sticky cum inside his secretary.
The pair collapsed in the chair and Jessica watched as the headmaster's cock subsided and slipped from between Helen's cheeks, a stream of cum dripping out of her and coating his thighs and balls. Helen lifted off and Jessica watched on as she knelt down between the headmaster's legs and started clean him with her tongue. The headmaster watched both women with interest, amused both by Helen's absolute slutiness and Jessica's disgusted reaction to it.
"Jessica, I want you to go now. Take that harness with you and the gel on the table, and when you come back next Thursday at 4:00pm I want you to be wearing it just like you are now. You'll have to make sure you put it on during your lunch break and I guess you'll have to wear it through your afternoon lessons... but at least that means you'll be somewhat prepared and ready for my cock when you get here."
Jessica couldn't believe what he was saying to her, the thought of the headmaster's huge cock penetrating her tight little arse was terrifying, but she just nodded, collected her things and left the room as she was told.
As she reached the door, the headmaster spoke once again, "And Jessica, don't forget your meeting with Helen here at 10:20 on Tuesday morning."
-- -- -- -- --
Over the next three weeks Jessica dutifully attended the six 'special' lessons as instructed. Jessica still didn't like doing it, but at least she had become accomplished enough for Helen to tell the headmaster that her performance was now 'satisfactory' and no further lessons would be necessary.
Jessica had gone to the headmaster's office on the Thursday afternoon as instructed, but there had been no one there to see her. During the day she had done as instructed and fitted the dildo in place, sitting through two hours of schooling with her backside full of rubber cock, and all for nothing. The following two weeks the same thing happened, she had been given a message both times to come to the office at four on each Thursday, but each time she went through the whole charade only to find the office empty and the headmaster's door locked shut.
After Jessica's final session with Helen, she had told her to come to the office on Monday morning at 9am, and to be wearing the dildo. During the last three weeks Jessica had not had any contact with the headmaster and his secretary had been so busy using the girl's tongue that she was actually feeling quite neglected.
Consequentially, Jessica has spent most nights with her hand between her legs bringing herself off. Strangely, having gotten used to the feeling of the dildo in her arsehole, Jessica had found herself enjoying the sensation and even fingering her back passage as she brought herself to orgasm. This snowballed, and by the end of the three weeks Jessica found herself bringing herself off with the dildo buried deep inside her and to her surprise found herself craving a larger model. She was still scared stiff at the idea of the headmaster's huge prick ploughing into her, but the thought of having a real, warm, flesh and blood cock reaming her hole was starting to appear in her fantasies more and more.
Although Jessica didn't realise it, she was playing out another part of the headmaster's carefully constructed (and indeed 'tried and tested') plan. There was never supposed to be any meetings during those three weeks, she had been left to her own devices and as expected her frenzied teenage hormones, her natural curiosity, and her fear of being fucked by the headmaster's oversized cock had brought about the expected results.
Now she stood in front of the headmaster's desk once again, with the dildo firmly embedded in her arse, she wondered whether today would be the day when he finally fucked her. The thought of it gave her chills, but also a tiny bit of excitement as he was sure to make her cum hard to compensate for the pain.
Jessica stared at the two empty chairs behind the desk. Both the headmaster and Helen stood behind her and she soon felt her skirt being removed. She had put her knickers on over the dildo and harness and the headmaster removed these before kneeling down behind her to fully appreciate the extent of her penetration.
"Very good Jessica," he said. "I'm pleased to see that you have carried out my instructions properly. Tell me though, you don't seem too uncomfortable... would I be right in assuming that your arse isn't exactly a stranger to that rubber cock anymore?"
Jessica closed her eyes tight and said nothing. The headmaster brought his hand down hard on Jessica's arse and then asked her how many times she had fucked herself with the toy. When she didn't answer he spanked her ass several times with increasing force and repeated the question.
"Quite a few times...Sir," she admitted in a tiny, shameful voice.
"And are you ashamed of yourself Jessica? Or do you think it's acceptable for one of my students to lie in her bed fucking herself in the arse with a rubber cock?"
Although Jessica felt quite ashamed by what she had done, hearing the headmaster describing her actions was making her quite horny. The headmaster continued as Jessica's breathing quickened slightly and she started to feel the heat building between her legs. The headmaster alternated between prodding the exposed end of the dildo through the harness and reaching between her legs to tease her moist cunt.
"Well Jessica, do you think it's right? Do you think it's just fine to have that rubber cock pressed between your cheeks, stretching your hole and filling you up inside?"
The headmaster was enjoying this and his cock was becoming uncomfortably hard inside his trousers.
"I bet by now you'd like a real cock up inside your little arsehole, wouldn't you? Just like you saw Helen have the other week. I bet you've been frigging your little clit like crazy remembering every moment of that scene. I bet you've been getting off on that every night since, with that dildo shoved right up inside you, just wishing it was my thick, long cock, haven't you? Well don't worry Jessica, because I'm not going to disappoint you today."
Jessica's cunt was on fire. His fingers were still teasing her, first at one hole and then at the other. Meanwhile Helen had taken the girl's wrists and fastened the leather cuffs around them once more. Jessica wondered why, but knew better than to ask.
"She doesn't seem very talkative today, does she..." Pondered the headmaster to his secretary. "I think she's probably just so ashamed of herself for all that arse-fucking she's been giving herself... and so she should be, what a dirty little whore."
The headmaster gave the dildo a prod which caused Jessica wobble on her feet slightly.
"I think the little slut needs punishing for her disgraceful behaviour. Being forced to do something is one thing, but she's enjoying it far too much..."
The headmaster held out his hand and Helen passed him a multi-tailed whip with a large, turned wooden handle. The turned elements of the handle made it comfortable to hold, but they also had another use. Jessica was ordered to lean over the desk and she complied immediately. Helen lifted her shirt tail out of the way and the headmaster began whipping Jessica's poor exposed backside. He didn't hit her too hard, just enough to bring some colour to her cheeks. When they were nice shade of pink he switched the whip around and pressed the turned handle against her pussy lips, sliding it inside her with relative ease. Each turned part of the handle teased her pussy in a different way and by the time the handle was fully inside her, Jessica felt very turned on and very full. Of course, with the strap-on cock still buried deep inside her as well, she really did feel completely stuffed, and the final torment came in the form of the whip tails, which hung down between her legs and tickled her clit every time she moved.
"I think I'm going to have to cane you again Jessica, you're enjoying this far too much."
"No, please, not again... it hurts so much!"
"Nonsense, besides... now your arse is nicely warmed up it won't hurt nearly as much. Unless I want it to..."
The headmaster fetched his cane and Jessica soon felt the cold, thin rod placed gently on her warm cheeks once again. The headmaster quickly struck and Jessica howled in pain. He struck again, leaving two burning red stripes straight across her pale skin. Jessica howled again, even louder this time and reached around to cover her arse, protecting it from more attacks.
Helen was delighted to see this and looked to the headmaster. He nodded his approval and his secretary rushed around the desk. The headmaster pushed away her hands and told her in no uncertain terms to put them in front of her on the desk. As she did, Helen grabbed them and quickly fastened them to the desk, leaving her completely vulnerable and unable to defend herself further.
Helen pulled the chain that secured her wrists to the desk tight, which pulled her forward so that she was balancing on tip-toe and stretched the muscles in her arse and thighs. The dildo in her backside felt even tighter than before and she was semi-relieved when she felt the headmaster begin to undo the harness which held it in place. He very slowly withdrew the rubber cock from her stretched arse, which created an amazing and intense sensation for Jessica which only came to an end when her muscles clenched and forced the remainder of the dildo out of her body.
"Excellent," said the headmaster. "Now those straps are out of the way, I can cane your arse properly."
"No," wailed the girl. "Please, not again..."
"Oh I'm sorry, I almost forgot."
Jessica wondered what he had 'almost forgotten' and then felt the wooden whip handle being pulled out of her cunt and pressed against her loosened arsehole. He firmly pushed it into her, but the ridges made it almost unbearable for Jessica and she cried out several times as each new ridge stretched her wider and wider.
Eventually the handle was fully inserted and Jessica was breathing deeply, trying to get used to this feeling of the large handle filling her arse. Again the whip tails hung down and each movement she made caused them to tickle her pussy lips, but right now that was the least of her worries. The headmaster resumed his caning and Jessica howled with each painful stroke, closing her eyes to try and block out the burning sensation that came with each fresh stripe across her rump.
She opened her eyes after the final stroke to see Helen sitting in the headmaster's chair with her legs spread wide, her fingers buried inside her pussy and clearly enjoying every second of Jessica's torment. As the headmaster moved away from the girl, the secretary got out of the chair and moved around behind her. She heard a rustling sound and then she heard the woman sucking on the headmaster's cock as he encouraged her and forced his cock deep into her throat.
"That's it, get it hard for Jessica's tight little arse."
Helen's fingers clamped around his shaft as she licked the tip of his meat.
"Yes bitch, squeeze it hard," he hissed. "That's real good, make it fucking solid so I can split her in two."
Suddenly the noises stopped and she felt Helen move behind her and push her tongue into Jessica's pussy. Then one or the other of them started fucking her ass with the wooden handle of the whip. The older woman started alternating between licking her cunt and biting the insides of her thighs, the mixture of pain and pleasure was intense and mixed with the thick handle moving in and out of her arse it began to stir the beginnings of an orgasm deep inside her.
Abruptly the pleasure/pain stopped and the handle was extracted, very quickly this time, but Jessica still felt each ridge as they rubbed over her abused ring. Jessica started to panic, realising that this was the moment she'd been dreading all this time.
"Please don't fuck my arse, please... I can't take it, you know I can't take it."
Jessica tensed as she felt the headmaster move closer and rub his cock against her red-striped cheeks. The secretary was still between her legs and somehow had managed to contort herself so that she could still manage to get her mouth right next to the girl's dripping cunt. In fact Helen was sitting on the floor, with her legs straight out in front of her, her head was pressed back against the front of the desk and this way she was just about able to lick the teenager's clit. One of her hands was between her own legs and she rubbed her own clit as she worked on Jessica's with her probing, eager tongue.
Jessica felt the headmaster pull her ass cheeks apart and then felt a torrent of cold gel being squeezed into and around her hole. This was followed by his fingers swirling through the gel and prising her arse open. The headmaster worked her arse for some time before she felt him guide the tip of his straining cock towards her opening and then tease her by rubbing it up and down her crack a few times, in the process thoroughly coating the first few inches of his meat with the gel.
"You can't wait can you slut? You just can't wait to have my thick cock inside your arse can you?"
"No... please, please don't stick that thing inside me, it's too big... I'll do anything, anything you want, but please don't fuck me with that..."
Finally he placed the tip of his rock hard prick against her opening and began to force it into her. Jessica was thankful for the extra lubrication and the pre-stretching she had already endured, but his cock was still painfully large. If it wasn't for the expert job that Helen was performing on her clit it would have been absolutely unbearable, as it was she couldn't help but howl as it plunged its way into her body, stretching her further than ever before and gradually working itself deeper and deeper into her poor arsehole. Slowly, the headmaster began to work his cock back and forth inside her. Jessica's breathing was intense and laboured but she was just about coping. Gradually over the course of a few minutes the pain subsided and Jessica slowly started to enjoy the feeling of fullness inside her.
"You love it don't you, you little slut. You love feeling my shaft deep inside your arse, don't you?"
The headmaster was in his element, he loved nothing better than fucking a young girl in the arse, especially when they howled and screamed like Jessica did. His sadistic side loved every second as he broke them and indoctrinated them with his twisted cocktail of pain and pleasure.
As Jessica got used to the sensations inside her he started pumping his thick shaft faster. Helen's discomfort increased as the fucking continued and the girl's mound was repeatedly bashed into her face, but she knew the headmaster would punish her severely if she did not complete her task properly. She lifted her hand up and caressed the headmaster's balls, and then tried to reach back and finger his hole, but she couldn't quite make it. The headmaster was annoyed that she was trying to 'bring him on' and vowed to punish her later. For now though he concentrated his anger on Jessica and began thrusting even harder into her.
Jessica squealed yet again and this spurred the headmaster on even further. Helen, sensing the increased urgency in the headmaster's strokes, doubled her efforts on the teenager's bud, but she wasn't quick enough and she felt the headmaster tense as he unloaded his balls directly into Jessica's raw arse. As he pulled his cock away, Jessica gave a load groan - a mixture of pain and relief, while the headmaster's cum dripped down, out of her arse and into the waiting mouth of his secretary.
Watching on, the headmaster pressed two fingers inside the girl's dripping cunt and roughly slammed them in and out, making sure to hit her G-spot on each stroke. Within thirty seconds Jessica was screaming again as her body convulsed around his fingers and she endured a huge orgasm that ripped through her like she'd never experienced before.
As she started to come down the headmaster used his free hand to spank her tortured ass cheeks, while Helen again teased her clit with her tongue and these two conflicting stimuli triggered a second orgasm that left her breathless, completely spent and collapsed across the desk.
Helen pulled herself up from underneath the girl, then wiped some spilt cum from her chin. The headmaster gave her a stern look and told her to untie the girl immediately. She rounded the desk quickly and slipped the cuffs from around Jessica's wrists, allowing her to fall back onto her feet again, but she remained splayed across the desk, completely and utterly shattered.
The headmaster leaned in close and whispered that she could go now. After a few moments Jessica stirred and the headmaster helped her into a chair so that she could recover fully before getting dressed. He walked back over to Helen and spoke to her in a very quiet, but very severe voice.
"You are in a lot of trouble, not only did you fail to make her cum while I was still inside her, but you also tried to cheat me of my ultimate pleasure by trying to make me cum too soon!"
Helen couldn't look at him, she had failed and she knew it.
"I was going to get Jessica to lick you before she left to show me what she had learned these past few weeks, but I don't think I'll bother with that now. Maybe I should allow Jessica to choose your punishment, after all it would only be fair. But then I doubt she'd be able to come up with anything depraved and humiliating enough, so I suppose I shall have to do it myself... In the meantime, you are not to touch yourself and if I suspect that you have then I will make it ten times worse for you."
Helen shuddered at this twist, she hadn't cum during the session, largely because of the discomfort she was in squashed under Jessica with her head bent back, and now she was being banned from even relieving her frustration. The worst part was that the headmaster had an uncanny knack of knowing if she had cum and so she couldn't even risk doing it secretly. It wasn't worth it anyway, despite her frustration she didn't doubt for a second that he could come up with something truly torturous if he put his mind to it and she didn't fancy giving him any excuses to extend his creativity any further.
The headmaster returned to Jessica and knelt by her side.
"Well done Jessica, I am very pleased with you. I want you to take the rest of the day off and go and relax. By the way, I have a couple of guests arriving a week tomorrow and would like for you to meet them."
He stood up and walked back to his desk, not even bothering to glance at Helen as he walked by. Jessica smiled to herself, not only had she had an amazing orgasm, two in fact, but the bitch from Hell was in trouble as well! Mind you, her arse hurt like hell inside and out and she didn't fancy a repeat of this any time soon, if ever. She wondered who the guests might be, she didn't really have a clue, but she hoped and prayed they didn't want to fuck her arse too.
Eventually Helen came over and helped her get dressed again, and within an hour she was back in her bed asleep. She couldn't help but drift off to sleep with her finger gently teasing her clit, but her arse was far too sore for even her slender fingers.
--- --- --- --- ---
Helen was barely left alone for the next three days, the headmaster spent as much time as he possibly could with her to make doubly sure that she could not relieve her ache. Helen was used to having sex at least once a day and for her to go three days without cumming was unbearable.
By the end of the third day Helen was unbelievably irritable and the headmaster was satisfied that the first part of her punishment had been a success. He told her to come into his office at five that afternoon and she spent the rest of the afternoon in a state of nervous excitement, desperate to cum... but wary that the headmaster would probably have a few tricks up his sleeve before he let her release her pent up frustration.
At 5pm she entered the office, her knickers already sodden due to her inability to concentrate on her work during the afternoon. The office appeared empty but she heard the headmaster behind her. Before she could turn around he instructed her to 'stay still'. He came up behind her and wrapped a blindfold around her head, then removed all her clothes and stuffed her saturated knickers into her mouth.
"I don't want you screaming the place down once I get started."
The room was always quite cold, but today it seemed absolutely freezing. Helen's nipples quickly hardened and the headmaster tweaked them roughly, pinching them hard and making her flinch. A muffled moan escaped her mouth, but the headmaster ignored it and continued squeezing, pinching and flicking at her pink buds.
The headmaster moved away slightly and then she felt a pair of leather thigh cuffs being strapped onto her legs. Then a pair of wrist cuffs were slipped on too and finally the two were joined together with a metal clip, effectively fixing her hands at her sides. Then the headmaster slid a leather collar around her neck and attached a chain to it, he also tied a wide leather belt around her waist before telling her to get down on her knees, jerking the chain downwards to emphasise his point. Once there, rather than go to the trouble of removing her gag, he rubbed his hard cock over her face and neck. Her soft skin felt delicious on his straining cock and he thought about all the times he had had her down on her knees like this and erupted all over her face and mouth...
The headmaster wanted her on all fours, but with her hands fixed to her thighs as they were he had to help her down so that her right cheek was pressed flat against the floor and her weight was supported on her shoulder. It was a little uncomfortable, but she'd suffered worse positions before. He then fed the chain from her collar between her legs and fastened it to the back of the belt around her waist. The chain was pulled tight and pulled on her neck slightly, but more importantly the metal links fitted snugly into her crack and split her pussy lips perfectly.
The headmaster studied his work and was pleased that his calculations on the length of the chain had been accurate. Then he decided to start the spanking. At first it was relatively gentle, but every smack seemed just a little harder than the last and after a minute or two her arse was beginning to redden. Helen was used to being spanked, of course, but she wasn't used to the chain that tortured her clit every time she made the slightest movement.
After a brief pause to rest his hand, the headmaster began again, each stroke slower to fall, but more deliberately placed and with much greater heft behind it. The sound of his hand slapping against her rump rang around the office like a shot and as he increased the power more and more Helen was finding the punishment harder and harder to take.
She howled into her gag as the headmaster continued to beat her, his hand was stinging like hell but he wasn't going to stop until he was good and ready. Helen had never been beaten so hard by hand in her life and continued to whine into her balled up panties.
The headmaster paid her no attention and continued with the beating until finally his hand could take no more.
By the time he had finished Helen had tears in her eyes and her arse was on fire, but still the fire burned between her legs and the chain continued to torment and frustrate her.
He reached down and removed her gag, "Well Helen, how do you feel now, are you horny enough yet or do you need some more?"
"No, please, no more..." She begged. "Please let me cum, I can't take it anymore."
The headmaster smiled, they both knew she wasn't cumming yet, but he was amused by her begging nonetheless.
"I don't think so, not yet... I think perhaps a little caning would help take your mind off your pussy for a while, don't you?"
"Nooooo," wailed Helen. "Please don't do that."
The headmaster chuckled to himself and went to the wall to fetch his cane. Helen heard it swish through the air a few times as he walked back across the room and then felt the cold, thin rod placed against her burning arse. The cane was lifted and Helen tensed up, waiting for the blow to land, but instead she felt the cane between her legs, nudging its way past the chain and penetrating her sopping wet cunt. Helen moaned loudly as she felt the movement inside her and then groaned as the cane slipped out and slowly inched upwards and once again negotiated the chain and slipped easily into her tight hole.
Each time the headmaster moved the cane back and forth it pulled the chain slightly tighter and twisted it against her burning clit, bringing her just a tiny bit closer to her release but nowhere near close enough. Then the cane was slowly extracted and seconds later she felt the searing pain of it brought down across her cheeks twice in quick succession. Helen howled out in pain, but the headmaster wasn't done yet and brought it down a further six times, leaving her arse striped red in eight different places.
To Helen's great relief she heard the cane drop to the floor and then felt hands on her arms, pulling her back upright, but remaining on her knees. The blindfold was removed and the headmaster saw that her mascara had run quite badly and some of her hair was stuck to her face with sweat. The headmaster gave her a few words of praise and a smile slowly returned to Helen's face. Her backside hurt like hell, but she knew the orgasm that was coming her way was going to be epic.
He pulled a chair up in front of her and sat naked facing her, his cock protruding obscenely upwards from between his legs. At the base of his cock sat a cock ring which pulled the skin tight and made his throbbing cock look even more impressively hard and angry than usual. He leaned forward and brushed the hair from her face, then kissed her on the lips. Helen kissed him back passionately, desperate to cum, desperate to suck his cock, just plain desperate...
"I don't want to have to punish you like this," he said in a slightly mocking tone. "But you will persist in being a naughty girl, and you know I always punish my naughty girls, don't you?"
Helen nodded solemnly while the headmaster stroked his cock, right there in front of her face.
"I know you want to suck it Helen, but first..."
He reached behind and grabbed a couple of items from the desk. He leaned forward and attached clamps to Helen's rock hard nipples. They were very tight and she sucked in a lungful of breath as she struggled with the sharp, unexpected pain. As she adjusted to the sensation she looked up at him with big eyes, just like a naughty schoolgirl who was afraid of what was coming next.
The headmaster grabbed her head and pulled it forward, her lips parting as his jutting cock speared between them. With her hands still strapped to her thighs Helen couldn't use them to balance or to stroke him or play with his balls. It was awkward and exhausting and it took a long time, but eventually the headmaster stood up from the chair and took control. He fucked her mouth hard and fast, his cock filling her throat as she gasped for air on every out stroke, her tongue working hard to tease his balls in a futile attempt to tip him over the edge.
Helen's legs were so tired she could hardly stay upright, and every movement of her head only served to rattle the chain that tormented her beyond endurance, but then she felt the headmaster's cock buck wildly and the first spurt of cum erupted into her throat.
He quickly pulled out and jerked his cock hard and fast, ropes of cum splattering her face and tits as he syphoned every drop of cum from his balls.
The headmaster dropped to his knees and kissed his secretary hard on the lips, oblivious to the cum that was still smeared across her face. His hands found her tits and she half screamed into his mouth as he ripped the clamps from her nipples and then roughly massaged his cream into her skin before reaching up and undoing the chain from the collar around her neck. He let it fall to the floor and slid two fingers inside her and slammed his hand repeatedly into her desperate aching pussy. They continued to kiss as she drew closer and closer and then finally exploded, almost collapsing in a heap and crying with relief at her long overdue release.
-- -- -- -- --
The headmaster spent the next few days away from the school, which meant that Helen was left feeling horny again. At least with the headmaster away she could masturbate whenever she felt the need, and besides there was the owner's monthly visit to look forward to...
Daniel Maverley, the owner of the school was pretty hands off, and he allowed the headmaster to run things as he saw fit. He knew what went on and while he wasn't entirely sure he approved, the fact was the school attracted a very wealthy client base. So he kind of took that view that as long as his bank balance looked healthy, he didn't ask too many questions or make too much fuss. He did however, have an arrangement of his own, with one of the other teachers, which meant that once a month he would visit the school and indulge in a Femdom session. For her part, 'Mistress' Claire received a substantial quarterly bonus and got to exercise her dominant nature.
When Helen had found out about the arrangement, she had done her best to make sure that she would be free to watch on the security camera, and she'd hardly missed a session. So, ten minutes before she knew the session would start she settled down in front of the monitor in the back room of the office block. She sank back in the armchair there, spread her legs wide and hooked them over the arms. Her fingers moved between her legs and she started to suck one of the two dildos she had brought with her for the occasion.
On the monitor, she saw Claire sitting at the headmaster's desk. She was already prepared for the owner's visit and she too was leaning back in her chair with her hand between her legs. She was dressed in a black rubber basque with matching stockings and her hair was tied back in a pony tail. The only other thing she wore was a pair of black, high heeled sandals.
Helen watched as Claire rose from the desk and opened the door, just twenty feet or so from where she was now, rubbing her pussy in anticipation of what was about to happen. The owner walked into the office and Claire immediately pushed him down onto his knees. She sat on the edge of the desk and told him to get undressed, as he did she parted her legs to give him a good look at her clean shaven pussy.
Daniel fumbled nervously with his clothes and Claire berated him for his clumsiness. While initially the money was undoubtedly her main incentive, as time passed by it was becoming less and less about the money for her. She loved that she got to abuse a guy once a month and she couldn't deny that each month she looked forward to her session more and more eagerly. Sure the money was fantastic, but in the days before each session she found herself getting wet and day dreaming about what she was going to do to her slave this time.
She slid off the desk, stood right in front of the man and pulled his head between her legs.
"Lick me," she commanded, and instantly Daniel's eager tongue began probing her sodden pussy.
Claire sighed as she felt him work on her aching clit, she grabbed the back of his head and ground her cunt against his face, then abruptly she pulled away leaving him panting for breath and licking her juices from his lips. Claire turned slowly around and leaned forward, her hands resting on her knees to steady herself.
"Lick my gorgeous arsehole," she hissed.
The owner buried his face in between her cheeks and Claire felt his warm, wet tongue slide eagerly into her waiting hole.
"Mmmmm..." She groaned as she pushed back against him slightly. "That's it, get it in there slave."
Helen watched intently as her fingers worked steadily on her clit, she was extremely wet now and pushed the dildo she had been sucking down between her legs. She slid it between her lips and eased it into her sopping cunt, burying it all the way in before pulling it half out again and then settling into a rhythm.
As she watched she noticed that the owner had started to stroke his cock as he serviced Claire's arsehole. It was only a matter of moments before her colleague noticed what he was doing and pulled away from him.
"I didn't give you permission to touch your cock slave! Get on the floor and lay on your back, and don't you dare touch that cock!"
Daniel lay down on his back as instructed while Claire straddled his head and lowered herself down onto his face. Almost immediately she realised that he was stroking his cock behind her back.
"Are you stupid?" She barked. "Do you really think I can't feel you touching your cock when I specifically told you not to?"
"I'm sorry Mistress," he whispered.
"No you're not... but you will be."
Claire lifted herself off Daniel's face and quickly turned around to face his feet. She sank down onto him again and positioned her arse directly over his mouth. She left it there for a few moments, just daring him to lick her without being given permission. He managed to restrain himself this time and finally Claire gave him the order to continue.
Helen was thrusting the dildo in and out of her cunt now as the scene continued to unfold on the screen in front of her. Claire kept him there for a quarter of an hour, just worshipping her arsehole with his tongue. Throughout the whole time she did nothing more than stare at his twitching cock, while rubbing her clit and occasionally reaching forward to slap his balls.
Eventually Claire's breathing became shallower and faster and her muscles started to tighten up in anticipation of her approaching orgasm. Daniel continued to work his tongue against her puckered hole and Claire's fingers moved faster and faster on her clit. She felt it build and build and then teeter on the brink, and then the orgasm hit her and she collapsed her full weight onto Dan's face, forcing his tongue as deep as it would go inside her arsehole.
After a few moments, Claire collected herself and lifted herself off the owner's red, breathless face.
"Well... that was adequate I suppose," she said. "But your earlier indiscretions are going to cost you."
She walked over to the headmaster's desk, pulled out the leather covered box from the drawer and selected a few items before walking back to where Daniel was lying, then told him to sit up. He felt a blindfold placed over his eyes and secured at the back of his head and then Claire told him to turn over onto his front. She coated a dildo with the headmaster's 'heat gel' and forced it into his backside. The heat was instantaneous and he felt himself start to squirm as it steadily increased in intensity.
"If you keep that up," warned Claire. "You'll be feeling the cane on your arse, and I know you don't want that!"
"No Mistress, please."
"Okay, you can turn back over now."
Daniel felt her take hold of his balls and tie a cord around them, then she looped it around his cock and tied it tight, making his cock throb and bulge obscenely.
"Up on your feet slave!"
Daniel got to his feet carefully, painfully aware that the dildo could fall out at any moment and earn him some further punishment. Claire guided him to the chair that Helen had been tied over by the headmaster and as she bent him over, the dildo worked loose and fell to the floor.
"Oh dear, you're really not scoring many points today are you?"
"I'm sorry Mistress..."
She picked up the dildo and shoved it straight back inside his glistening hole, bringing a fresh grunt from Daniel's throat. Then she tied his wrists and ankles to the chair, crushing his cock against the wooden backrest. Daniel heard something being slid from the desk in front of him and then seconds later he felt the first fall as the whip was brought down across his cheeks. He cried out in surprise, but then managed to keep silent as Claire beat his ass and the backs of his thighs until they were glowing pink.
Daniel heard the whip tossed onto the desk and then listened as he tried to make out what was coming next. He heard Claire moving around and some rustling noises, but couldn't quite work out what it might mean... but all he really cared about was that it wasn't the cane, he really hated the cane.
"Are you looking forward to your caning slave?"
"No Mistress, please don't..."
Claire laughed softly to herself, she had no intention of caning him this time, it was clear from their last session that he hadn't enjoyed it and she wasn't a fool. She may be the Mistress, but he was the one paying her bonus - but that didn't mean she couldn't fuck with his head a little! Besides, if she made him think he was getting caned he'd be all the happier when he didn't.
"Aaaaw, really... don't you like it?"
"No Mistress, I hate it."
Claire placed the cane across his cheeks and felt him tense hard.
"Are you sure you don't want me to... I promise I'll be gentle."
Before Daniel could answer, Claire lifted the cane and tapped it softly against his glowing skin.
"There, see... I know you don't want it like I do, but I know what you do want..."
The cane clattered as it hit the desk and the owner felt her move behind him, pulling the dildo out of his arse and pressing the tip of her lubed-up strap-on against his hole.
Helen watched as her friend and colleague inched the strap-on inside her slave. As she did so she pulled the dildo that had been inside her pussy and moved it back towards her arse, placed the tip against her hole and slid it inside. The feeling of her arse being filled brought a fresh stream of juices to her already sodden cunt and she grabbed the second, larger dildo and slammed it inside her wanton hole.
Despite the owner's obvious discomfort, Claire worked the strap-on deep into his arse and then picked up the pace, holding onto his hips as she roughly pounded him. Daniel's tightly bound cock ached and throbbed as it was mashed against the back of the chair and he wondered at one point if he might accidentally cum without permission.
"That's enough," sighed Claire as she pulled the strap-on out of her slave's ravaged arse.
Daniel let out a moan of relief, as the feeling of emptiness slowly receded. Claire stood behind him for about fifteen seconds, waiting for him to relax, before she pushed the dildo straight back inside him again.
"Ugh," she groaned as she rammed the fake cock into him. "I love fucking your tight little arse... in fact I could do this all day."
Dan closed his eyes and gritted his teeth again as she reamed his hole, praying that she wouldn't push him over the edge and ruin his orgasm.
Thankfully, after another minute or so Helen pulled out for good and he heard her undoing the straps that held the strap-on in place and dropping it to the floor. He heaved a sigh of relief, he loved being fucked in the ass, but it was often quite intense, both mentally and physically.
Once his bonds were untied, Daniel was told to lie on the floor again and Claire lowered herself onto his face and his tongue was soon in her tight hole again. As she enjoyed the feeling of her slave's eager tongue worshipping her arse, Claire slapped his cock and balls hard and dragged her nails along the length of his straining, throbbing shaft.
Suddenly, she lifted off his face and turned around, sinking herself down and impaling her pussy on his aching stalk. Both of them groaned with pleasure as she started to ride his cock.
"Do you want to cum in my beautiful pussy?"
"Oh god yes..."
Claire ripped the blindfold away and left him squinting up at her.
"Do you?"
"Yes Mistress."
"Then tell me."
"Please Mistress, please let me cum in your beautiful, tight pussy."
Claire reached forward and pinched his nipples hard as she continued working her cunt up and down his stalk.
"No, tell me...look in my eyes and tell me, you know what I want to hear."
Daniel fell silent, remembering their last meeting and how she'd allowed him to cum inside her and then caned him when he refused to lick his cum out of her used pussy.
"Maybe we should stop now and you can just finish yourself off later?" Pushed Claire.
"NO! Please, I'm so close... I need to cum inside you."
"Do you? Well, you know what that means, unless you want me to cane your arse again."
"No Mistress, please, I..."
Claire slowed right down, concerned that he was going to shoot inside her before he managed to get the words out.
"Please," he begged. "Please let me cum inside you."
"Not until you tell me what I want to hear."
Claire was still now, and she reached around and squeezed his tightly bound balls.
"I can feel there's so much cum in these balls... tell me what you want me to do slave!"
"Please Mistress, please let me cum inside your beautiful pussy and... and lick you clean."
"Again, convince me!"
Helen was transfixed by the scene unfolding on the monitor, she had stopped fucking herself with the two dildos now and merely left them wedged inside her pussy and ass while she rubbed her clit. She was desperate to cum herself but she wanted to wait until she could watch Daniel licking his cum out of Claire's well fucked pussy, so she kept taking herself close and backing off, watching and waiting...
Claire slowly started to ride the owner's cock, building up speed as she made him tell her again and again.
"Please Mistress let me cum in your beautiful pussy and lick you clean."
"Please Mistress let me cum in your beautiful pussy and lick you clean."
"Please Mistress let me cum in your beautiful pussy and lick you clean."
"You really want it don't you, you really want to suck all that hot, sticky cum out of my hot, wet cunt don't you?"
"Yes Mistress..."
"Don't fail me, you know what happened last time."
"I won't Mistress, I promise."
Claire slammed herself down on Daniel's cock repeatedly until she felt him tense and then buck hard as he started to erupt inside her. She pounded his body then, draining every last drop of his cum out of his balls and into her greedy hole. As soon as he finished, Claire lifted herself off him and moved up his body. Daniel looked up to see her moving towards him, a slither of white cum already dripping from between her pussy lips. She eased herself down onto his face and after just a moment's hesitation she felt his tongue move between her lips and start to lick her clean.
Watching closely, Helen finally allowed herself to cum and as her body shook with pleasure, her muscles tightened around the dildos inside her holes, intensifying the pleasure greatly. Helen had been watching and toying for nearly an hour and had edged herself repeatedly, when it finally came the orgasm was as overwhelming as it was exhausting.
Through heavy eyelids, Helen watched as Claire's sat astride the owner's face, rubbing her clit as he continued to lick her pussy and swallow all the cum he had shot inside her. The last thing Helen saw before she fell asleep was Claire's back arching as she started to cum...
--- --- --- --- ---
Jessica spent the next week wondering who the special visitors could be, and she still didn't have a clue even as she waited outside the headmaster's office to be called in to meet them. After about five minutes waiting on her own, another girl walked into the reception area... it was Lauren, the girl who had brought the message that day and given her a strange look. Jessica tried to ignore her but she came and sat down right next to her.
"So you're in the headmaster's little gang then?" Asked Lauren.
Jessica turned her face away, not knowing quite what to say.
"You didn't think you were the only one did you? God, the headmaster's fucked all my friends, probably had most of the rest of the school too..."
Lauren's openness put Jessica on edge, but before she could speak the office door opened and Helen called them both inside. The room was empty, but the secretary led them over to another door that was in deep shadow and that Jessica had never noticed before. This room was smaller than the huge office, warmer and cosier, it contained a sofa and a couple of soft chairs.
The headmaster was sitting in one chair and Helen sat down in the other, facing them were two men in suits. The headmaster told Lauren to sit between the two guys and Jessica wondered where she was supposed to sit. She was pleased when the headmaster called her to him and patted his leg, indicating that she should sit on his knee, facing the two strangers.
The headmaster and the two men talked for a while and it soon became clear to the girls that they were school inspectors on a visit. As the headmaster talked to them he started to stroke Jessica's leg and explained to the men that the girls where part of his special training programme.
The two guys looked interested and Jessica was surprised to see that Lauren was already starting to flirt with them. 'What a little whore' Jessica thought to herself. 'She can't wait to fuck them!'
While the headmaster continued talking to the suits, he gradually parted Jessica's legs until they were practically sitting on the edge of their seats trying to get a better look. It must be said that while Lauren was more eager, Jessica was prettier and maintained an air of innocence that the men found very attractive.
The headmaster went on to explain that Jessica was a fairly recent discovery, but that Lauren had been on the scheme for two years already and was almost ready to graduate. He didn't mention that his personal interest in Lauren had all but disappeared. These days she liked getting fucked a bit too much for the headmaster's tastes, it rather took the fun out of it, besides... if he wanted an eager slut he had Helen to play with.
The men, both in their early forties, but fairly trim, started to flirt back with Lauren. The headmaster continued talking with them as they did so and no one even noticed Helen spreading her legs until she actually started openly rubbing herself. Suddenly, one of the guys, Peter, turned his attention to her and motioned for her to come over to him.
Helen stood up and moved across the room, eager to find out what this new guy's cock was like. She sank to her knees in front of him and pushed him back in the chair. She pulled his cock from his trousers and greedily fell on it, sucking the head while she stroked his shaft slowly.
The other guy, James, began rubbing Lauren's tits through her shirt. He was pleased to discover that she wasn't wearing a bra and quickly felt her nipples hardening beneath the thin white cloth.
Jessica didn't know what she was supposed to do. She felt the headmaster part her legs further and his hand fall down between them. He pulled her close and whispered in her ear.
"How would you like to be fucked by three men at once Jessica? One in your mouth, one in your pussy and one in your tight little arse..."
Jessica shuddered.
"Please don't make me do that Sir, my ass was so sore last time," she pleaded.
"Well, we'll see... for now you just make sure these two are happy. Lauren knows what to do, just follow her lead."
He pushed Jessica off his knee and towards James. She watched as Lauren unzipped the guy's pants and pulled his cock out. Jessica pulled James's pants down further and joined her, the girls taking it in turn to suck on his throbbing prick. Jessica was grateful that he was a little smaller than the headmaster, the thought of a bigger cock than the headmaster's drilling her ass filled her with absolute dread.
The headmaster moved behind Helen and removed her skirt, underneath she was wearing black stockings, suspenders and black lace knickers. The headmaster was pleased, a cliché it may be, but at least she had a sense of 'occasion'. He reached under her and stroked her pussy through the lace as she continued to suck on Peter's cock.
It was perhaps as well that Jessica hadn't seen Peter's cock yet, as it was a good two inches longer than the headmaster's already considerable length and at least as thick, if not slightly thicker. Of course Helen was more than happy to suck on this huge new toy and she used her fingers to tease his balls as she greedily swallowed him as far down her throat as she could.
The headmaster pulled his cock out and turned Helen around to face him. She stood up and bent down to suck on his hardening cock, sticking her backside out and reaching between her legs to grab Peter's massive cock. He moved forward and pulled her knickers aside before working his fingers inside her. Then he bent down further, his cock moving beyond Helen's reach as he pushed his tongue into her tight arsehole. Helen groaned loudly into the headmaster's balls as she sucked him, pushing back against Peter's eager tongue, wanting it harder and deeper inside her tight hole.
At the other end of the sofa, James was finding it increasingly difficult to hold back as the two girls sucked and wanked him together. Eventually he gave into the feeling and his cock spurted load after load of hot, salty cum across the two girls faces. The girls eagerly licked his cock and balls clean and then Lauren took hold of Jessica's head and started kissing her, licking the cum from her face and spitting it into her mouth. Jessica was a bit taken aback at being kissed by another girl but she remembered the headmaster's words that she should follow the other girl's lead.
The headmaster watched on smiling as Helen continued to suck his cock. When the girls had finished he told them to undress each other carry on. The two girls unbuttoned each other's shirts and took it in turns to suck on each other's tits. Lauren was eager as always, but predictably Jessica was hesitant and slightly awkward when it came to touching another girl.
Lauren pushed the younger girl down onto her back and then swung her body on top of her, grinding her pussy against Jessica's mouth and chin. The two girls began to lick each other's pussies and before long each had fingers inside the other one too. Lauren was the first one to go for the other girl's arse and forced one of her wet fingers into Jessica's tight hole. Jessica wasn't expecting it and responded by forcing one of her fingers into Lauren's hole too.
The headmaster pulled out of Helen's mouth and she returned to Peter, climbing onto the sofa and sinking down onto his large cock. She gave a little cry as she felt his cock fully penetrate her, the headmaster's cock had been the biggest she'd ever had inside her and now she knew for sure that Peter's cock was definitely longer and thicker.
She watched the two girls over her shoulder as she rode the thick rod between her thighs and was excited to see the headmaster move behind Lauren and push his fingers into her tight hole. Jessica watched from underneath as she continued to lick Lauren's clit, then she saw the headmaster's weighty cock come into view and slide easily into the other girl's wet cunt.
The headmaster wasn't interested in fucking Lauren's pussy, he just needed some lubrication and after just a few strokes he pulled out and eased the tip between the girl's cheeks. Lauren grunted into Jessica's pussy as she felt him forcing his cockhead into her arse. He grabbed her hips to get some leverage and Jessica watched in awe from below as he slid inside her until his balls blocked her view.
Barely giving the girl time to accept his meat, the headmaster quickly started to fuck her hard. Lauren though didn't miss a beat as she continued licking Jessica's pussy and moaning loudly as she pushed back against the headmaster's violent thrusts.
Sitting in between the two scenes, James sat on the end of the sofa, slowly massaging his prick until it was starting to come back to life.
Meanwhile, Helen was really grinding herself down on Peter's cock while at the same time reaching back to finger her own arse. Peter had ripped her shirt open when she had first mounted him and was now chewing her rock hard nipples though her lacy, black bra. The rough treatment of her nipples and the extreme size of his cock was bringing her closer and closer to orgasm and after a few more seconds she started to feel herself cumming and pulled his head between her tits as she clung to his neck.
As she came, moaning loudly into his ear, her pussy tightened around his cock and sucked the cum from out of his balls until it coated her insides. As he came Peter bit hard into Helen's tits, prolonging her orgasm until they both collapsed in a heap.
James watched intently, his cock now fully hard, and as the pair finished fucking he turned back to the right to resume watching the headmaster and the two girls.
The headmaster was really pounding Lauren's arse now, and accustomed to it though she was, even she was finding it hard going. Finally the headmaster pulled his cock out of her and jerked it until ropes of cum splashed across her cheeks and down the backs of her thighs. Some of his cum also fell onto Jessica's face and she felt her own orgasm building quickly as she watched while Lauren continued teasing her aching clit.
But as he pulled away the headmaster ordered Lauren to stop what she was doing and get up. He also reached down and pulled Jessica up off the floor as well and had the two girls standing in front of the sofa, right in front of James, Peter and Helen. Then he ordered Helen up off the sofa and told her to stand with 'the other girls'. Helen obeyed and stood to Lauren's right, she had a pretty idea what was coming next and couldn't wait to see the other girl's reactions.
"So gentleman, what do you think of my girls? Aren't they just the biggest bunch of sluts you've ever come across?"
Peter and James concurred with the headmaster's view and were more than on board with the headmaster when he suggested the best thing for them would be a good spanking.
The three girls spent time on each of the men's laps until their arses were glowing red. Peter would finger each of the girl's asses while he spanked them, but James would be the one who smacked the hardest, and each girl was relieved when it came time to move on from his lap to another.
After a good fifteen minutes spanking each of the girls, all three guys had their cocks hard again and were itching to fuck again.
Lauren and Helen were ordered onto the floor this time and the other four watched as they moved into the classic sixty-nine position and their mouths found each other's pussies. Both were eager to cum and they went at it hammer and tongue, desperate to climax before the headmaster found them something else to do.
Jessica's relief at not being asked to join in this lesbian scene was short lived as she now realised she was left with the three cunt-hungry men with big, hard, throbbing cocks. The headmaster asked Peter to lay down on the floor and then guided Jessica so that she was standing over him. He told her to sink down and Peter guided his stalk into the girl's sopping wet pussy.
The headmaster then patted James on the arm and indicated to him that he should kneel above his friend's head and as he did so Jessica dropped her head and accepted his cock into her mouth. Then the headmaster moved close behind her and grabbed the cheeks of her tender arse. He pulled them apart and applied some lube from a tube that was close to hand, before forcing his fingers into her arsehole.
Then he pressed his cock-head into her hole and she felt herself stretching to accommodate his length. With Peter's huge cock inside her pussy as well, she felt incredibly full and hoped this wouldn't last too long.
It took a little while for the three men to find their rhythm, but once they did and Jessica got used to the sensation of three men thrusting in and out of her holes, she started to relax and even enjoy the feeling of being thoroughly and completely fucked. The cock in her ass was the only sticking point, she loved the feeling off Peter's cock inside her pussy and she loved to suck on the one in her mouth but the headmaster's cock was just one too many for her... she knew she was a slut, but she wasn't that much of a slut.
Helen came first of the two girls and as she did the headmaster told the guys to stop fucking Jessica. They all pulled out of her and he told her she had done very well.
"Good girl Jessica, now, go over to Helen and she will make you cum."
Jessica looked over at Helen who wasn't best pleased with this new instruction, but she knew like the other girls she had to obey the rules or face the consequences.
Jessica had never felt so empty as when the three guys had removed their cocks from her body. She slid crawled across the floor to where Helen was and lay down on her back. Helen rolled over and moved between her legs, lapping at the girl's pussy and savouring the taste of Peter's cock on her lips.
The headmaster held out his hand to Lauren and she moved closer to take it. He leaned her over the side of one of the chairs and squeezed some lube into her arse before filling it with a large rubber cock. Lauren purred excitedly as he pulled her up and pushed her down onto Peter's thick meat and then straddled the other man's head and shoved his cock deep into her throat. As he pulled her forward onto his cock, James was moving behind her, a thick coating of lube already applied to his cock. As she sucked on the headmaster's cock Lauren waited for James to pull the dildo out of her arse and for his cock to press against her tightest hole, but instead she felt James's prick slide next to Peter's and squeeze alongside it inside her hot, wet cunt.
As James' cock inched inside her pussy, Lauren looked up at the headmaster with pleading eyes, she almost screamed as the second dick stretched her wider than she'd ever gone before but he did nothing but smile as he looked down at her, watching as she paid the ultimate price for over-achieving in his school for sluts.
Once inside, the two guys found a common rhythm and Lauren was subjected to the fucking of her life. They moved together like one enormous cock and she could do little but surrender to it as the headmaster kept a tight grip on her head as he fucked her throat.
James could feel the dildo rubbing against his cock through the thin wall of her pussy and this added stimulation meant he was first to let go, his spunk flooding the girl's cunt and oozing out of her as the two cocks continued their fucking in tandem. Peter didn't last much longer and his second load of the day soon erupted inside the girl and it too oozed out of her as the two cocks softened and shrank leaving her feeling empty and used.
Finally the headmaster buried his cock deep inside her mouth, his balls mashed hard against her chin as she felt him pulse repeatedly as he shot rope after rope of hot, creamy cum straight down her throat into her stomach.
As Jessica watched what was happening just a few feet away from her she felt her orgasm approaching and Helen's expert tongue took her right over the edge. Once again, right as she hit the edge, Helen shoved her fingers into the teens' tight arse and the girl bucked hard and long, howling in pleasure until at last she was still.
Lauren was left as the only one who hadn't cum, and as everyone else was completely shattered, the headmaster told her to sit in one of the chairs and bring herself off. Lauren was too exhausted to argue and sat down and hooked her legs over the arms of the chair, exposing to her audience the base of the dildo that was still buried deep inside her arse.
Without hesitation or shame she started rubbing her clit hard and fast, her orgasm the only thing she cared about in the world right at that moment. Jessica and the others watched on as she exploded, the two guys' cum still dripping out of her stretched-out cunt and her young body twisting in ecstasy until she too became still.
-- -- -- -- --
A few days later Jessica found herself back in the headmaster's office. As she had waited outside, her friend Kelly had emerged from within looking a bit furtive and had merely given Jessica a weak smile as she left.
'There goes another one' though Jessica as she watched the other girl leave.
Kelly had left the door ajar and she heard the headmaster's voice calling her to come inside.
"Sit down Jessica," began the headmaster.
Jessica sat down calmly, wondering what on earth could possibly happen to her next.
"I've spoken to your father this morning... and it's been decided that it's time for you to leave here. So, someone is coming to fetch you tonight. I believe you are to move back home and potentially finish your schooling at a facility near where you live."
Jessica wasn't quite sure how she felt about the news, part of her was elated to be going home, but she had made some good friends here and she'd learned a lot about herself while she was here.
"I know going back is going to be a bit weird for you," the headmaster said. "But I'm certain that a girl of your calibre will do well and make your father a very proud man."
Jessica rushed back to her dorm to pack her things, she couldn't wait to see her sisters again. The headmaster had told her to come back to the office at 6pm, and when she did she found the offices empty once again.
She looked around the room and thought about all the things that had happened to her here. Standing there alone in that room, it dawned on her just how much she'd changed since she had arrived. She dropped her bags and sat in the chair facing the headmaster's desk for a while, the hours passed but no one came, and she started to get bored and tired. It seemed unusually warm in the office this time, and as she relaxed in the chair she couldn't help but lay back and tease her pussy with her fingers until she fell asleep...
-- -- -- -- --
Jessica woke up about a half hour later. In front of her, sitting in the headmaster's chair was her father.
"Daddy!" Cried Jessica as she realised who was sitting there.
He held out his arms and Jessica ran around the desk to hug him. He sat her on his knee and they talked for a while about what was happening and the move back home. After a while her father started to talk about his plans for her and how he was going to start bringing her into his business when they got home.
"You can be of great use to me Jessica, I hope you have learned a lot while you have been here."
It was only now that Jessica noticed her father's hand resting at the top of her thigh, and now he looked into her eyes as he moved it down under her skirt and down between her legs. Surely her father wouldn't...
"A lot of my clients, and potential clients would like nothing better than a sweet, 'innocent' girl like you to play with... and you wouldn't want to disappoint your father would you?"
Jessica slowly shook her head.
"Good girl."
His hand reached its target and Jessica felt his fingers rubbing her pussy through her knickers. She felt her pussy flood even though she knew it was more wrong than anything she'd done since she'd arrived at the school and the shame washed over her like a tidal wave. Instinct took over and she tried to close her legs, tried to stop him touching her...
"What's a matter baby, Daddy's cock not good enough for you?" Her father whispered as he became a little more insistent with his touch. "The headmaster tells me you've taken his cock plenty of times already, even in your tight little arse."
Jessica couldn't believe it, she'd been set up right from the word go. Now she understood. Charlotte had come here before her and when she came home she started working all hours for Daddy's company, now he needed another whore and she was next in line.
Despite herself, Jessica felt herself getting wetter and wetter. She realised that this whole thing was about breaking down her barriers and making her own body betray her, even with the one person who she should never let touch her that way. She felt his fingers sliding inside her knickers and brushing against her sweet little pussy and couldn't do anything but groan into his neck and open her legs wider, inviting him to touch her. Inviting him to take her and make him hers.
"Does my little baby want me to fuck her?"
She wanted to say no, but her pussy seemed to suck his fingers inside, desperate for his touch.
"I think you do," he continued. "I think you want Daddy's cock real bad..."
As he continued to press his fingers deeper his other hand found one of her breasts and gently squeezed it.
"Please don't make me do this Daddy... we shouldn't do this, it's so wrong."
Jessica was saying all the 'right' things but there was no conviction or fight left in her voice. She looked deep into her father's eyes, looking for the parent that had always been there to protect her and comfort her, but instead all she could see was the lust he had for her body.
"You don't want me discipline you do you baby, your headmaster told me how much you hate the cane."
"No Daddy, please don't... I can't stand the pain."
"I know baby girl, believe me I don't want to cane you either, it's not my thing - that's why I sent you here, to the experts. I don't want to hurt you, I just want to make you feel good."
Jessica felt herself losing any last vestiges of control and opened her legs further still, arching herself forward to pull his fingers deeper into her sodden cunt. Her father kissed her and then raised his fingers to his lips and tasted her delicious juices, he'd waited a lifetime to taste them and his cock was painfully hard inside his trousers.
He slowly undid her shirt and cupped her breasts in his hands, admiring her sexy young body for a moment before speaking again.
"Oh Jess, you have no idea how long I've wanted to fuck you. I wanted to fuck Charlie as well, but you were always my favourite..."
Jessica groaned as she heard those words and wrapped herself around her father, nuzzling his neck and breathing heavily into his ear.
"Fuck me Daddy," she whispered. "Make me yours... like you did with Charlotte."
Jessica's father slid her off his knee and pushed her over the desk. She hesitated, fearful that he would cane her, but he reassured her and she relaxed. Laying across the desk she couldn't help but think how many times she'd been in this position before and how many times the headmaster had punished and fucked her.
She felt her father kneel down behind her and spread her legs wider. He slowly pulled her knickers to the side and when his breath hit her pussy lips she nearly came on the spot. She pushed back against him as his tongue swirled between her soaked lips, then pushed inside to taste her properly. His cock ached like he'd never known before and he didn't know how much longer he could hold back.
"You taste fantastic baby," cooed her father and Jessica moaned into the desk, conflicted but desperate for his cock inside her.
Her father licked her again and then pushed two fingers inside her. Then he shifted his tongue upwards and she felt him pressing it hard into her arsehole, fucking her with his slippery, wet muscle.
"Fuck me Daddy, fill my pussy up with your cock, I need it so bad... please Daddy, shove it in me, I want it, I need it!"
Jessica felt her father standing up and then heard the zip of his trousers as he pulled his cock out. He fed it between her sodden lips and buried it to the hilt in her hot, wet cunt. It was the most overwhelming thing Jessica had ever felt in her life, her father's big, hard cock... the one that created her, filling her up and making her his forever.
Jessica's father grunted as he bottomed out inside her, he knew this was a moment he would never forget and he paused to take in the sensations as he would never feel them again. After a pause he grabbed her hips and slid out almost all the way, then in again, all the way until his balls smacked against her clit. He fucked her like this for a minute or two, but soon he knew his cock was as wet as it was going to get. He pulled it out and grabbed the shaft with his hand, then pressed the tip against her puckered hole.
"No...Daddy, please don't... please, just the normal way..."
She felt the cock press forward, stretching her hole again as the others had done before.
"No please, Daddy, please..."
Her father pushed hard inside her and then grabbed her plait and pulled her head back.
"I'm going to fuck you all the time when we get home baby, and you're going to love it."
He started fucking her slowly, building up his speed as she got used to his thick meat reaming her arsehole. He reached around her waist and his fingers found her clit, Jessica groaned as she felt her arousal peaking again and she felt herself starting to push back against her father's cock, willing him to fuck her harder and deeper.
His fingers worked their magic and within a couple of minutes Jessica felt herself cumming harder than ever before.
"Oh... My... God!" She screamed as her whole body tensed and bucked, her arse tightening around her father's meat and pushing him over the edge too so that he filled her with his hot cum for the very first time.
He collapsed on top of her, kissing her neck and telling her how amazing his little girl was. Jessica felt dirty, but she couldn't deny the power of the orgasm she had just experienced, it made all the others up until now pale into insignificance.
-- -- -- -- --
The next morning the headmaster was pleased to find an envelope addressed to him on his desk. Inside, along with a bonus cheque, he found a letter thanking him for training his middle daughter and promising to send him his youngest daughter 'Chloe' along, just as soon as she turned eighteen.
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