Jessica at the Finishing School Pt. 01

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.