Jessica At The Finishing School Pt 05

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 the final part and I hope that those of you who have enjoyed my story believe it was worth the effort.

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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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.

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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...

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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.