Jessica at the Finishing School Pt. 03

"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.