Jessica at the Finishing School Pt. 04

This story was written in 2000, annoyingly I am having to transcribe it from a physical copy since that is all I have available. I hope you enjoy it and you think it worth my efforts. This is part four of five, since the feedback has been largely positive I am cracking on with the rewriting/transcribing and the last part should be done very soon.

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

Check out my newer stories under my new name Robert_Anthony.

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

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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.

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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 accidently cum without permission.