Jessica at the Finishing School Pt. 02

The headmaster pulled away from Helen and left her kneeling on the floor. She continued to rub her pussy as she watched him move over to where Jessica sat with her legs spread and her pussy exposed to the pair of them.

The headmaster looked down at her and she found herself looking into his eyes as his rock hard cock bobbed just inches away from her. Part of her wanted to reach out and touch it, but she was too nervous and unsure to do so. Instead she continued pleasuring herself, her fingers rubbing her clit as she waited for his next instruction.

"You look so innocent Jessica, and yet... underneath it all, you're just another horny.. little.. slut."

Jessica let out a tiny groan as he spoke and her chin trembled slightly.

"What are you Jessica? I want to hear you say it."

"I'm a horny little slut..." she gasped.

He smiled and corrected her.

"I'm a horny little slut, Sir!"

Jessica repeated his words and he smiled wickedly.

"I wonder if you've learned anything yet..."

He grabbed his cock and moved forward, pushing his cock between her lips and filling her mouth with his throbbing, hot meat. He watched as Jessica struggled with the new sensation, allowing her to go at her own pace, wanting her to enjoy her first taste of cock. He looked over his shoulder at his abandoned secretary, clicked his fingers and pointed to the floor between the girl's widely spread thighs.

"Get down here and lick her slut."

Helen almost leapt across the room, such was her eagerness to taste the pure, virgin pussy she was being offered. She sank between the girl's legs and pushed them slightly further apart, grabbing the girl's fingers and licking them clean before she lowered her head and began to put her eager tongue to good use.

Jessica found the idea of another woman licking her pussy disgusting, but as Helen's skilful tongue teased and pleased her pussy she slowly forgot her inhibitions and found herself squirming against the pleasure giving muscle between her thighs. Encouraged by her actions, Helen took it upon herself to slide first one, then two fingers into the girl's tight virgin hole.

"Do you like having your pussy licked Jessica? I think you do... I think you like it a lot.

Maybe if my secretary is very good, I will allow you to lick her hot, sticky cunt later, would you like to lick her pussy and make her cum?"

The look in Jessica's eyes betrayed her repulsion and he smiled to himself as her continuing naivety and innocence displayed itself for his amusement.

Eventually Jessica closed her eyes and concentrated on trying to please the cock that filled her mouth, at the same time enjoying the sensations that Helen was providing between her thighs. As the pleasure built more and more she let the headmaster's cock slip from her mouth as her body slowly tensed and then exploded as she came hard on the other woman's tongue.

As she recovered from the exertion of her orgasm, Jessica opened her eyes to find the two of them looking at her intently.

"So, being licked by another woman isn't so bad after all then..." stated the headmaster sarcastically.

Jessica said nothing, now that she had cum she suddenly felt ashamed of her slutty behaviour and quickly closed her legs, trying to hide her sodden pussy from view.

The headmaster reached down and helped his secretary to her feet, then kissed her hard on the lips, tasting the young girl's juices as he slipped his tongue into her mouth.

"Delicious," he said and smiled at Helen before he turned his attention back to Jessica, who was already in the process of pulling her skirt down and trying to regain some sense of decorum.

"And what do you think you're doing?" Enquired the headmaster. "I haven't finished with you yet!"

He reached out his hand and Jessica stood up to take it. His fingers closed around hers and he lead her over to the desk. Once there he lifted her up and told her to lie down.

Jessica lay back, and as he pulled her legs back towards him so that her arse was almost on the edge of the desk, Helen was removing her clothes and tossing them aside until she stood naked bar her black, seamed stockings. As she watched the headmaster arranging the girl as he wanted her she couldn't help but tease her pussy with her fingers and then taste herself once more.

The headmaster lifted Jessica's skirt, then slid her knickers down her legs and off over her feet. He placed them on the desk next to her and then started to push Jessica's legs apart. She resisted at first and he pushed harder, his strength gradually overcoming her resistance.

"All you have to do is say the word and we'll stop right now Jessica... but you know what will happen if you do, don't you?"

The thought of her father being called and whisking her away to the dreaded Catholic school made her surrender and she relaxed the muscles in her legs. The headmaster pushed them wide, exposing her wet, slippery pussy and moved forward to position himself at the entrance to her inviting hole. He grabbed his cock and gently teased her lips and clit with the head, savouring the first moments of her deflowering. Despite herself the sensation sent a shiver through Jessica's body and she found herself moving in time with him, desperately craving more friction and pleasure and ultimately to feel him inside her.

He grabbed her sodden panties and thought for a second about gagging her, he didn't want the place screaming down when he took her virginity with his large cock, but then he had a better idea.

"Helen, get up here and sit on her face," he half whispered.

Helen was on the desk like a shot and before Jessica realised what was happening the other woman's pussy was being lowered onto her mouth.

"No.." protested Jessica as she turned her head away from Helen's dripping slit.

The headmaster eased the tip of his cock into her tight teen cunt.

"You have to learn to give and take Jessica, and if needs be I will beat that lesson in to you."

The headmaster pushed deeper, feeling the girl's incredibly tight pussy contracting as he forced himself inside her virgin hole. Jessica groaned into the secretary's hot, wet pussy as she struggled to accommodate his throbbing meat. The headmaster loved nothing better than the feeling of a fresh, tight cunt surrendering to his cock, though he'd taken countless girls by now it was a feeling that never got old.

"Get that tongue moving Jessica, unless you want me to use my belt on you again."

Jessica's body tensed and strained as the headmaster's cock stretched her poor virgin pussy wide open. Her half-hearted, stop-start pussy-licking was ineffectual, but Helen was still aroused by the feeling of her pussy being teased by the young girl and the sight of her lover defiling her innocent body. She reached down and pulled the girl's shirt open, exposing her pale skinned belly and then pulled her bra up roughly until her soft tits sprang free.

The headmaster reached up and squeezed them as he continued fucking Jessica's sweet cunt, his pace quickened and he drove his cock deep and hard into the young girl, all too aware that he couldn't hold on much longer. At the last second he pulled out and pumped it hard with his hand, releasing a huge load of cum which erupted all over Jessica's stomach and tits. Jessica felt the cum landing on her skin and gave up the pretence of attempting to lick Helen's pussy completely

Helen leaned forward and greedily licked her lover's cum off the girl's body, as she did she moved back slightly and Jessica was spared the sight of the older woman's pussy dripping onto her face.

"You will learn a lot from Helen," said the headmaster. "But like many things in life, there's an easy way and a hard way."

As he spoke he idly fingered her wet, stretched pussy

"So Helen, how would you rate little Jessica's skills today?"

"Awful," smiled Helen. "She barely even tried."

It was clear to the headmaster that Helen was looking forward to seeing the girl punished.

"Oh dear, lack of experience I can forgive, but selfish disinterest I can't abide. You realise of course that it will be necessary to punish you... and I think, as it was Helen who suffered your unwillingness to perform, that she should decide your punishment."

Jessica's heart sank. What kind of perverse punishment would that crazy, sex-mad bitch come up with?

Jessica tried to hide the huge grin that was threatening to engulf her face, she was delighted to be consulted but she knew her options were limited at the moment. What she really wanted to do was slip into her largest strap-on and plough the girl's tight ass, but she knew the headmaster wouldn't allow it at this early stage.

"I think the little slut should be caned," she said after a few moments thought.

Jessica gasped in fear as the memory of her first caning returned.

'Not very imaginative' thought the headmaster, but an adequate punishment under the circumstances.

"Okay Jessica, get up and lean over the desk."

"No, over the chair like befor..." started Helen.

The headmaster glared at her as Jessica lifted herself up and stood between them on the floor.

"Over the desk," repeated the headmaster firmly as he turned to retrieve his cane from the wall, just as he had the last time. Helen was really making a rod for her own back today.

"Please, don't cane me... I'll do it properly if you want me to, please," begged the girl.

The headmaster held the cane in his fingers, twirling it as he enjoyed her obvious discomfort.

"I'm sorry Jessica, but you need to learn to do as you're told... and you need to learn to do it, or at least try to do it, without being told twice."

"But..."

"I'm sorry Jessica, but unless Helen is in a forgiving mood, I'm afraid you'll just have to take your punishment."

The two of them turned to look at the secretary, but Helen was never going to give an inch.

"Cane her," she hissed.

The headmaster shrugged and tapped the cane on the desk. Jessica slowly lowered herself over the desk and felt the headmaster lifting her skirt up and out of the way once again. He looked over his shoulder and saw Helen sitting in a chair, her legs spread wide and her fingers working her clit as she enjoyed the sight of her lover preparing the girl for her punishment.

He turned his attention back to Jessica, all too aware that any second now his secretary would be forcing at least one finger into her own ass as she brought herself closer to orgasm. He placed the cane across Jessica's cheeks for a moment, before swiftly lifting it and slamming it down onto the girl's flesh.

Jessica howled in pain and he snatched up the girl's knickers from the desk where he had laid them earlier. In a flash he grabbed the girl's jaw and pushed the wet ball of cotton between her lips.

"You have to learn to keep quiet girl!" He snarled.

He glanced over at Helen, who was now indeed fingering her ass as she watched on, and clearly not too far away from cumming.

"Dirty bitch," he muttered to himself before turning back to Jessica again.

He looked down at the one red stripe that currently decorated the girl's cheeks, then ran the tip of the cane down the crack in her ass before letting it slide back and forth against her pussy lips a few times. He rested the cane parallel to where the first blow struck and Jessica waited nervously for the next searing blow to arrive. The waiting was almost as bad as the actual strokes, and the headmaster strung it out now as he listened to Helen's rapid breathing and moaning behind him.

He firmly placed his hand on Jessica's back to keep her still then laid three quick, hard strokes across the girl's cheeks. Jessica screamed into her panties, while on the other side of the room Helen screamed in ecstasy as she took herself over the edge and her body convulsed through a huge orgasm.

The headmaster placed the cane on the desk and removed the panties from the girl's mouth.

"I hope you have learned something here Jessica."

"Yes Sir," she murmured, struggling to get the words out as she wiped the tears from her eyes.

"Good, you may go now."

Jessica got herself together and left them alone in the office. The headmaster retrieved his shorts and trousers and dressed himself as he looked down at the exhausted, motionless form of his secretary

"I think you should spend an afternoon alone with her," said the headmaster. "Teach her how to eat pussy properly, her innocence is endearing but we need to bring her on or we will run out of time."

Helen nodded in agreement, her eyes still half-closed as sat up and tried to collect herself.

"And you... I think it's time you were taken down a peg or two as well, barging into my office like that, who the fuck do you think you are?"

Now it was Helen's turn to look at the floor.

The headmaster went to his drawer once more to retrieve the leather covered box. He selected a heavily contoured dildo from the box and smeared it with some kind of gel. He walked back over to Helen and told her to get down on her knees. She complied immediately and the headmaster quickly and roughly parted her cheeks before forcing the dildo deep into her ass.

The gel was hot and within seconds Helen's arse was on fire. The headmaster watched in amusement as she struggled and writhed below him. He reached down and grabbed the base of the dildo, turning it inside her before pulling it out and slamming it back in again. Helen felt some of the gel slither down between her legs and start to heat up her pussy, she reached back and tried to brush it away but all she did was work it into the skin and make it more effective.

The headmaster knelt down beside her and rubbed his hand across her arse cheeks.

'Time for a good old-fashioned spanking' he whispered as he lifted his hand and slammed it down again.

Helen had been spanked a thousand times before, but never with her ass burning from the inside out. The headmaster spanked her backside until his hand was numb and her cheeks were crimson red. Beneath him Helen was snivelling into her forearms as she struggled to cope with her punishment, but she knew as well as he did that she wouldn't have it any other way. He toyed with the dildo some more before getting up, walking back to his desk and putting the box away again.

"Get dressed," he said. "And leave that dildo in for the rest of the day. I'll be checking on you later."

Helen dressed awkwardly and scampered out to her desk, it was going to be a long afternoon.