Greenwood Academy Ch. 01

With a start, he brought himself back to the task at hand. "How many is that, Georgiana?" He demanded, straightening back up, his cock straining against his trousers almost painfully.

"Six, Sir!" Georgie whimpered.

"Two more. Poor baby, this is rather a harsh punishment for your first time, isn't it. Well, afterwards I shall soothe you and we'll have a little talk." He stepped back, took aim and lashed the cane down on her buttocks, laying a stripe diagonally across the parallel pattern that striped her spread cheeks so prettily.

"AAAAAAAAAAAAAAAAAAAAAAAAAAAAAHHHHHHHHHHHHHHHHHHH!!" Her scream rang through the room, and not for the first time he was glad it was virtually soundproof.

"Last one. I hope this has taught you your lesson, Miss Montgomery. Although I expect you're going to be one of my regular visitors, hmmmmmm?" He smirked and raised the cane, aiming the last stroke to fall wickedly across the middle of her thighs, knowing this to be one of the most vulnerable spots on a girl's anatomy.

SWWWWWWWWWWWWWWWSHHHHHHHHHHHHHHHHHHHH...the cane whistled and landed with a satisfying smack of thin oak on girlflesh.

"AAAAAAAAAAAAAAAAAAIIIIIIIIIIIIIIIIIIIIIIIIIIIIIEEEEEEEEEEEEEEE!!" Georgiana shrieked, sobbing and howling, as the last wicked lash marked itself into her tender thighs, bringing an indelible end to her first caning.

Mr. Jordan laid the cane down on the desk and wiped his forehead, then sank into the chair and pulled it close to the trembling, sobbing girl. He gave her a few moments to absorb what had just happened. This moment was one of his favorites, the euphoria of feeling his dominance, of knowing that the pain she felt came from him, and was well-deserved, and would be taken by her and used to mold her character and behavior.

Georgie lay there, shaking and spent. She felt Mr. Jordan's hands gently untying her wrists, pushing the drawer between her thighs shut, taking her onto his lap. She winced as her welted bottom came in contact with his lap, and he shifted her to a more comfortable position slightly on her hip. He stroked her hair and waited as her sobs slowly subsided and she relaxed against him.

"Shhh, now. It's over. It's over." He soothed, feeling her body subsiding into his embrace. Her skin was smooth as satin and he ran his hands down her back, her arms, her softly rounded hips. His cock was standing to attention and he shifted slightly, letting her feel it against her. She gasped and raised her eyes to his, long dark lashes matted and wet with her recent tears.

"Headmaster?" she whispered, blinking slightly as she realized that his hands were caressing her slowly.

"Hmmm?" He murmured, leaning down to plant a small kiss behind her ear. She squirmed and let out a tiny moan. His hand slid down between her thighs and one finger slipped between her slick pussylips. She moaned louder as he stroked her, teasing her.

"You weren't a very good girl for your punishment, Georgiana. I really shouldn't be rewarding you in this way..." He murmured against her ear, pulling his hand away.

"Oh...please..." She moaned, writhing on his lap.

"Please, what?"

"Please...don't stop..." She pleaded, raising her face to his, eyes full of confusion.

"Poor little Georgiana. This is all so new for you, isn't it?" He resumed teasing her, his skillful fingers finding her clit and tweaking it softly. She gasped and jumped, and a smile spread across his face. "Here at Greenwood Academy, our goal is to mold and shape you girls into young women. Education, discipline...punishment...and sometimes, reward." He circled her clit slowly, his other hand reaching behind to trace the welts from his cane. "And although you don't deserve a reward, not for your appalling little performance in the classroom, not for your snotty attitude, and certainly not for your lack of control whilst getting a very well-deserved punishment, I do understand that you're confused, and I believe that you want to be a good girl."

Georgie nodded slowly, a slowly dawning realization forming that she DID want to behave for Mr. Jordan. His fingers stroked her slowly as she processed this information, her pleasure connecting in her mind with the need to be a good girl for the Headmaster. He watched the emotions play across her face, satisfied that she was 'getting' the lesson he was teaching her. His fingers stroked and played with her gently as he listened to her soft moans. He found her clit again and pinched it between his thumb and forefinger, rolling it and feeling her ride the waves of her pleasure. Her pussy was slick with juice and he raised his fingers to her mouth, smearing it across her lips.

"Taste what a good girl you can be, Georgiana." He murmured, then stood and lifted the compliant girl to her feet. She moaned in protest but he shushed her and led her to the couch in the corner of the room where he laid her down on her stomach and pulled a jar of ointment from his desk. He started to rub it precisely into the welts on her bottom, taking care to be very gentle with her. She let out little gasping cries as the ointment stung before soothing, and soon the little cries were replaced with little questioning moans as his fingers slipped back between her thighs, parting her lips and gliding into her tight little pussy. She rocked back, arching her back, and he slid one finger into the tight puckered bud of her anus. She gave a sharp little cry and shrunk away from his touch slightly, but he shushed her. "Now, Georgiana, you must give in to whatever I feel you need. This is the beginning of your training and I'm going to be very firm with you about everything, punishment, pleasure and how I use you. Now relax and enjoy the feeling, and after you've had your release we shall begin on training you to please me."

She nodded mutely, and allowed the pleasure to wash through her, finding to her surprise that the feeling of her tight little anus being stretched on his finger was indeed an erotic one. In a few moments the Headmaster had brought her to a gasping, shuddering orgasm on his fingers, feeling her pussy and ass clenching and pulsing with her excitement. "You are not allowed to play with yourself in secret, do I make myself clear, Georgiana? The pleasures of the flesh are mine to dole out to you, not yours to take." Mr. Jordan stood and lifted the limp girl off the couch, setting her down on her knees in front of him. She stared mutely down at the floor until he raised her chin with one finger, forcing her to stare into his eyes. He noticed with satisfaction that all of the defiance had fled, not only from her posture, but from the expression in her eyes and on her face.

"Y...yes Sir..." She whispered, her lips trembling as she spoke.

"And when you feel the desire to do so, you are to come to me, and we will discuss whether you are to be allowed release."

"Yes." Her voice was so soft he had to lean down to hear her. He smiled.

"Good girl. You are beginning to understand how I operate here, and how I intend to make you into my very good girl, aren't you?" His fingers caressed her face as he spoke, and she nodded.

"Now. Punishing you has given me a bit of a problem. When I'm forced to take action like that, it makes my body respond in a way that might seem...inappropriate to some people. Do you know what I mean, Georgiana?"

She nodded again, remembering the feeling of his hard erection against her as she was caned, and then again on his lap.

"And as you are the cause of this...difficulty, you will be the one to take care of it, hmmmm?" He brought her face closer to his bulging trousers so that her eyes were firmly in line with the outline of his erection. Her eyes widened, and he chuckled softly. "Have you ever seen a man's cock before, little girl?" He asked, his voice husky.

"N...no, Sir...not a man's..." She trailed off, embarrassed.

"Well, this shall be your first lesson then. Give me your hand." He reached down and she hesitantly put her hand in his, and he brought her palm up to cup around the fullness of his shaft. She let out a little sound somewhere between a cry and a gasp. He molded her hand to his thickness and shifted it up and down a bit, nearly exploding at the contact of her little fingers around him. "Unzip my trousers." He commanded. Her hand fumbled a bit and he helped her to find the zip pull, and moaned as she slid it down. "Take it out." He could hear her swallow audibly, as she reached into his pants and touched his cock for the first time. Her fingers closed around the silky skin of the head and tugged hesitantly. With a groan of impatience he pulled his cock free and pulled her close to it by her hair. "Taste it." He demanded, forgetting all his plans to be slow and gentle with her, nearly frenzied with the sight of her so close to his throbbing member. The head was oozing precum and her huge eyes were fastened on it, a mixture of fear, fascination and bewilderment obvious in them.

He sighed and loosed his grip on her hair slightly. She didn't draw back, but instead, to his amazement, leaned forward and let the pink tip of her tongue flick out against his cock, tasting him.

"Oh fuck..." he moaned before he could control himself. It was just too good, this beautiful little girl kneeling naked before him, her ass striped with the marks of his cane, her thighs smeared with the juices of her orgasm that he had wrung from her, and now...she was tasting cock for the first time ever.

His cock.

"Oh, my little girl..." He moaned, his hips moving forward involuntarily as he held her head. She moved toward him slightly and opened her full lips, taking the head into her mouth, swirling her tongue around him as if she were sucking a particularly delicious lollipop. He was torn between a moan and a laugh at the innocence of her, the exquisite touch of her warm, wet mouth on him. She swirled and sucked him in deeper and he held her head gently between his hands, letting her set the pace.

"Sweetheart...you're a natural..." he managed to gasp. Her mouth worked up and down his shaft with hesitant determination, her hands snaking up to hold his thighs and gain her leverage to take him deeper. She seemed determined to give him the same sort of pleasure that he had given to her. He could feel his balls tightening as he came close to exploding, and he pulled back slightly, afraid to frighten her too much. She surged forward, resisting his attempt to slow her down, and with a low cry he felt himself begin to cum, gushing his load down her throat as she choked a bit attempting to swallow it all. He pulled out, fearing that she couldn't breathe, and shot out the second half over her face, bedewing her cheeks, chin and eyelashes with pearly strands of his cum.

His hips jerked with the force of his orgasm, and he realized that he was still holding her head. Her eyes were shut, face thrown back, covered in his cum. He was panting, almost disbelieving that she had managed what she had just done, her first time sucking cock. She opened her eyes and gave him a beatific smile.

"I'm a fast learner, Mr. Jordan."