Jessica At The Finishing School Pt 03

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 three of four or five, since the feedback has been largely positive I am cracking on with the rewriting/transcribing with the aim to get at least one part done each week until it's finished.

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

Check out my newer stories under my new name Robert_Anthony.

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

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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.

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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.