The Headmaster

Though I must apologize to my wonderful readers who are hungry for more "Orgasm Torture" for not posting any installments lately, I hope that this "early work" of mine will amuse and arouse them. There a hundreds of fantasies that take place in all-female academic settings (and that's just in *my* mind!) but hopefully, you will find this one different enough to make it stand out from the rest.

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The Headmaster.

Ever fantasize that you are a teacher at an exclusive finishing school for young ladies? Maybe your charges have been getting into too much trouble - the headmaster had caught some of them - out after curfew, maybe smoking. The headmaster was forced to deal with them quite harshly - taking them to a room that is shrouded in mystery - even fear - among many students. You'd heard that the headmaster would administer a thoroughly spanking or even paddling to the offenders in that room - but you'd never actually seen anything for yourself - just rumors. Even so, the thought of such a thing intrigued you. That, and you had strange feelings for the headmaster - a quiet, studious, yet somehow irresistible tall, dark man.

At times, you imagined yourself having to answer to him for an infraction worthy of the kind of punishment you'd heard rumors of. The thought of it mad you wet between the thighs, and once or twice, you had to hide your blushing face from the headmaster.

You're surprised as a student interrupts your English class with a message that the headmaster wants to see you immediately.

"oooooohhh!" your class whispers.

You quickly quiet them and put one of your student aids in charge of the class. Straightening your skirt, you quickly head to his office, wanting to make a good impression.

"Ms. Smith" he says meeting you at the door to his office."

"Yes Mr. Banner?" you answer quickly.

"Walk with me, we have an important matter to discuss" You follow him down the long hall as he strides to a part of the school you never visit.

Taking a well-worn key from his pocket, he opens a door at the end of the hall and gestures for you to enter. He follows - the door closes and locks behind him.

"Ms. Smith, I'm sorry to say that 5 of your students have been sent to me for discipline over the last month. It seems that you are not making a very ladylike impression on your students. It is your job - yet it seems to say that I needed to make a more tangible impression on them."

"Sir?" you ask, getting quite nervous.

You notice then that the room is devoid of furniture - except for a high padded table with a slanted top in the middle of the room. The rest of the room is bare except for a cabinet of the wall.

"Ms. Smith, you are doubtless familiar with the rules of our institution - disobedience or insubordination will not be tolerated in any form. I assume you are also familiar with the terms of your contract?"

"My contract sir?"

"Of course, I refer to the section that speaks to remedies provided to the administration to ensure that the teachers provide the proper example to the students."

"Why, of course" you say - lying - you didn't read the contract at all.

"Then you'll understand if I have to ask you to accept the prime remedy prescribed for teachers such as you."

"Of course" you lie again - hoping he would quickly tell you what the answer was.

"That would be for the teacher to receive corporal punishment if 3 or more of their students were referred to the headmaster for discipline within any 30-day period."

You felt a cold sweat break out - surely he couldn't expect you to accept a spanking like one of the students!

"Well then" he concluded, walking to the high end of the padded table, and patted it. "Let's get on with it then" - patting the table again - indicating you should take position bent over it.

"But, but, Mr. Banner..."

Now Ms. Smith, let's not make this any more unpleasant than it needs to be" gesturing again.

You screw up your courage and walk to the table - bravely standing on your toes, you lean over the high end of the table, lowering your head and upper body to the padded surface until they are lying lower than your hips. You feel your short skirt riding up - possibly exposing your stocking tops - but you couldn't reach to pull it back down. Mr. Banner stepped behind you and seemed to study the fabric stretched tightly over your quivering bottom. He swiftly lifts your skirt up over your hips and bottom by the hem as you object and try to rise. He pushes on the small of your back, putting you back into place.

"Ms. Smith - now don't be difficult or I'll be forced to attach restraints to you.

The embarrassment of him seeing you bent over with only thin silk panties covering your bottom was only the beginning as you felt him reaching for the waistband and tugging them down.

"NO!" you cry out, trying to stand again as the silk panties are pulled below your knees, then off completely.

"Ms Smith, do I need to tie you?"

"No please, I promise to do better, don't do this!"

He laughed - "You wouldn't believe how many times I hear that same thing said in this very room." 'This is your first visit here, so I won't have to be too severe with you - but one more outburst on your part, and I will tie you down Ms. Smith!"

You lie against the table and resolve to take the punishment - and not to give him the satisfaction of breaking down in front of him. You hear the creak of old hinges as he opens the cabinet on the wall. He fumbles for a moment and returns to your left hip.

"I've selected a soft leather paddle for your spanking Ms. Smith - It will sting considerably, but if you hold still, shouldn't leave any lasting marks. I think 20 or so licks should suffice for a first offense."

Part 2

You feel his left hand firmly - but yet gently on the small of your back again - not so much to hold you in place, more like he's trying to make contact with you. You imagine the view he is getting - your quite bare and vulnerable bottom, framed by the stocking tops and garters. You're bent over fairly sharply - you imagine that from the right angle, he could see between your shapely thighs and cheeks to see the fur-covered lips of your pussy - the pussy that even now is growing wet with excitement. You are surprised and a little embarrassed to think that the prospect of being spanked like a little girl by the headmaster should arouse you so. You feel the gentle touch of the leather paddle touching the skin of your bottom - you jump in spite of the soft touch - ready as you were for a stinging swat.

"Easy Ms. Smith, we haven't even begun yet." he tells you, quite calmly, even charmingly.

"I thought I would make your introduction to the paddle a gentle one - rest assured, I don't do this for the students sent to me."

He continues to gently slide the smooth leather over your bottom cheeks, so softly, cheek to cheek, around each one, top to bottom. You bite your lip to suppress a moan of pleasure. You are powerless to suppress the waterworks being turned on between your thighs however. You are beginning to worry that your excitement will soon become obvious to the headmaster - what would he think of you then?

He draws the paddle back an inch or two and gently slaps it against your bottom. You jump - not with pain, but with surprise. You inadvertently let the moan that was hanging in your throat escape - telegraphing your true state of mind. The paddle is large enough to cover both of your cheeks at once, but the "blow" he delivered left neither sting nor redness.

You relax and settle onto the table while the headmaster draws the paddle back for another spank. Six inches back this time, and brought down a bit harder - Smack! - more noise than pain though. You again jump from all the pent-up adrenaline, but only "MMM" escapes your lips.

You're sure you feel a trickle of your excitement begin to escape your labia now as erotic thoughts fly through your head. Another smack coming - a bit harder again -

"Smack!" across both cheeks - delivering a sharp sting that quickly changes to warmth that seems to course through your pelvis and up through your stomach. The warm feeling between your soft thighs grows steadily as the moisture continues to build.

SMACK! the slightly harder slap causes your bottom to ripple under the headmasters skilled hand. Now you're sure that your lubrication is beginning to overflow from your steaming pussy.

SMACK!! Another blow, just a bit harder than the last. You realize now that the tone of your cries has been anything but distressed. The sound you make reminds you of your excited moans and whimpers as you pleasure yourself late at night - you feel your face warming with a blush as you realize that the headmaster knows you are aroused.

Sensing your total arousal, the headmaster delivers 5 more strokes at the same intensity in rapid succession - to add a bit of pain to your pleasure. SMACK! SMACK! SMACK! SMACK! SMACK!

You buck with each blow, and emit a more suitable "OH!" or "OW" with each impact, though you remember having been spanked much more severely as a youngster. Though heat now exists on the surface of your bottom, the heat from within has far outpaced it.

You feel the headmaster's hand caressing your back now, sliding over the silky garter belt, touching you on the soft naked skin above the lovely cleft between your now rosy cheeks. "mmmmmmm" you moan - uncontrolled, and unmistakably passionately.

"10 so far Ms. Smith - are you learning anything?"

"Yes sir" you answer, trying to disguise the sexy huskiness that has worked it's way into your voice. Once again the paddle caresses your bottom, soothing the built-up heat with it's smoothness.

Your bottom doesn't hurt - it feels energized! You think to yourself that you will have to make a stop in your room after this - not so much to get straighten your clothes, but rather to relieve the desire that has been building between your thighs.

He continues to stroke your now sensitive bottom with the paddle as his left hand caresses your back - almost to the cleft.

"Tell me what you're feeling Ms. Smith," he demands, "and please be honest."

"I, I, um...." you hesitate to say what you're truly feeling, for fear of admitting too much. "It hurts Mr. Banner, but not terribly so." you offer.

"Is that all Ms. Smith?" "ummm Yes" you lie. Suddenly, the leather crashes down on your helpless bottom 5 more times - harder than the last five. CRACK! CRACK! CRACK! CRACK! CRACK! Each blow drawing an honest yelp from you. He quickly places his bare hands on your cheeks - preventing a real burn from developing. You draw your breath in through your teeth as his hands meet the tender flesh of your bottom. He gently caresses the red areas.

"Ms Smith, I've been spanking young women's bottoms for over 10 years, you don't intend to tell me that your honest answer to my question is 'It hurts'. Now, I ask you again - tell me how it feels, and if you aren't completely frank with me, you'll get the next 5 harder still, and some additional strokes for lying."

You blink a tear from the corner of your eye from the sudden sting and sigh. You answer honestly this time:

"I like it Sir, it feels good even though it hurts."

He isn't ready to let you off that easily:

"What do you mean by 'like it'?"

"I like it sir, it feels good, it makes me feel, feel excited - sexually."

"Yes - I knew that Ms. Smith - but I wanted you hear you say it."

His soothing hands begin caressing your pink bottom. His strong hands rub slowly around each warm globe, from the top to the bottom of your cheeks - all the way to the crease where thigh meets bottom. A stray finger even lightly brushes your pubic hair, making you even more aroused.

"Why don't we finish then, Ms. Smith" he remarks, more of a statement than a question.

You brace as he picks up the paddle again, but needn't - the last five strokes are hardly more powerful than the first few, with ample soothing of the paddle being slide over you skin between each stroke. He finishes the "punishment" and returns the paddle to the implement cabinet. You feel him standing behind you, silent, taking in the full view of your freshly spanked bottom, seeing the trickles of your personal moisture escaping your pussy onto your inner thighs. You subtly adjust your hips on the table, spreading your legs slightly, giving him a better view.

Part 3

He notices the subtle shift in your position which gives him a better view - and smiles - both from the splendid view of your ripe womanhood, but also from the knowledge that he has thoroughly aroused this sexy woman. He decides to put the second part of his plan into effect.

"Ms. Smith - your spanking is quite finished - you took it quite well. You're free to get up.... unless...." he pauses.

She was a bit disappointed to hear him say it was over - she was too hot to allow it to end here.

"Unless what. Mr. Banner?"

"Unless you'd be interested in assisting me with a little research I've been working on - strictly voluntary, you understand."

Not knowing what it would be, but suspecting it would involve more of his intimate attention, you agree quickly.

"Good! I have some new ideas that I brought back from a conference last summer in Japan that I need to try out before incorporating them into our policies."

He continues, stepping in front of you and kneeling to talk as you lie on the table.

"Several institutions in the East have found that often poor behaviour or performance in women such as you is not the result of poor discipline, rather, it seems to be sexual frustration."

Though she was not happy to admit that she was sexually frustrated, she did nod her head in agreement.

"Some of my contemporaries have found that mild corporal punishment, combined with relieving this pent-up sexual energy did wonders for their students and teachers concentration. Apparently the theory and practice goes back over 100 years."

Unlocking a cabinet under the table, he withdraws an ancient, but highly polished rosewood box or oriental design.

"I obtained this special 'counselators' set in Japan."

He unlocked the box and opened it for her to see.

"These are antique Ivory, used by the headmaster of an exclusive school in Tokyo. When he retired, he gave them to me to employ here."

She saw 5 ornately carved cylinders of ivory ranging in size from an inch in diameter and about 6 inches long, up to one nearly 3 inches in girth and over a foot long. At first she didn't grasp their significance.

"Beautiful craftsmanship, don't you agree?"

Upon closer inspection, she realized what she was being shown - each "cylinder" had a smooth, rounded tip that exactly resembled the head of a man's erect penis! The smooth tip, flaring slightly to a pronounced ridge, then a slightly slimmer "shaft" that was a perfect replica - except for the intricate flowers and dragons carved into it. Finally, the other end was shaped into a handle.

"With your permission, Ms. Smith, I'd like to see if we can achieve the kind of success that our counterparts in Japan have experienced."

She looked at him and nodded dumbly, unable to speak for the excitement of what was about to happen.

"Excellent!" he replied. "I do have a few minor preparations to make first however."

With that, he set the box down in front of her and moved again to where her bottom was waiting, elevated for his attention. She felt him gently lifting her left foot up and outward, setting it on a step at the table leg, he cinched a leather strap around her ankle. He moved the right foot outward in a like manner, securing it as well.

She realized now that he had spread her legs quite widely - leaving no secrets about her state of arousal. She felt his left hand on her bottom again, but differently this time. Gently, even passionately, she even felt his thumb caress the top of the cleft between her cheeks.

"I just need to get an idea about size Ms. Smith - You have had sex before?

"Well, yes, in my final year of college." she answered - knowing not to dare lie!

"and nothing since then?" he probed.

"Well, not sex, but I, ...." she stammered.

"Say no more Ms. Smith, I will assess the situation."

With that she felt him gently caressing her labia, sliding a finger from the bottom to the top of her dripping slit, then sliding slowly into her hot vagina.

"Mmmmmmm" she purred. A bit more caressing, then two of his fingers entered her soft wetness.

"Ohhhhh!" she moaned. He withdrew these, then replaced them with three of his fingers.

"AHHH!" she gasped out, feeling his fingers filling her. He returned to the head of the table and knelt before her.

"I think we're ready to begin the experiment Ms. Smith" he said, reaching for the box, and selecting the middle sized ivory shaft. She guessed it to be about an inch and three-quarters thick and about 12 inches long.

He smiled at her as he hefted the long dildo in his hand - she smiled weakly back at him. He walked behind her again and put his left hand back on her bottom.

"Ready Ms. Smith?"

Nodding, "Yes," came the nervous reply.

She felt the cool smooth tip touch her labia, and begin to trace the same path his fingers had a few minutes earlier - up, down, bottom to top and back through her slippery slit. She felt it pause at the entrance to her vagina - she took a deep breath. Slowly, he pushed the flared head of the dildo into her - she felt her labia stretch around it - widening, bit by bit, 'til she felt the head pop in. She suppressed a sigh as it did.

Her thighs were trembling in anticipation of what would come next. He held just the head inside of her for a moment, then slowly began to advance it in further. The texture of the ornate carvings began to caress her wet labia as the shaft slowly slid inside her. She felt it filling her, more - more - filling her still more.

His thumb caressed further down the cleft between her cheeks as he continued to slide the hard ivory dildo into her pussy. She let out a slow moan as the dildo moved deeper inside her - filling her so full - so filling - so satisfying!

Her labia being tickled gently by the texture was giving her tingles like never before - she could feel the flared ridge of it's head moving deeply inside her. So deep, so hard, so hot! Her breathing was more regular now, deep and full - just like her pussy. Still the thick dildo slid deeper inside. He moved it farther inside - he was moving it so slowly - so slow she could feel each millimeter it moved, so slow that the carved designs slid slowly past her sensitive lips.

She felt a pressure inside of her that was new to her - he had slid the dildo deep inside of her, to the bottom of her hungry pussy - to her cervix. Such welcome fullness! She let out a very satisfied sigh as she felt the pressure.

"Mmmmmmm!" she moaned in appreciation.

He held the thick shaft deep within her. She had to concentrate on her breathing, the sensation was so intense, the pressure of the dildo's head pressing against the deepest part of her vagina. He kept a gentle pressure on it, not pushing, but not retreating either. He allowed her vagina a few seconds to adjust to it – he could see it slowly slide a little deeper in as her vagina stretched to accept as much as possible. A full additional inch slowly slid in as he held it. He could feel the trembling of her muscles through her back and bottom – his thumb gently stroked the top of her cleft.

"Doing OK, Ms. Smith – or should I stop?" he asked calmly.

"NO!" she cried out, "I mean, I'm fine, don't stop!" she said a little more calmly.

He grinned "Good, I think you will especially like the next part."

He slowly drew the ivory dildo back – only about a quarter of an inch, then slowly moved it deeply in again. She sighed as she felt the ridged head move within her, the carvings teasing her inner labia. Slowly, gently, he began to repeat the stroking – just a quarter of an inch out, then back in, over and over, massaging her pussy so deeply – plumbing her to the greatest of her depths.