3 comments/ 76337 views/ 12 favorites The Headmaster By: P_V 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. ***** 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. The Headmaster I wanted to say thank you to the One that helped me write and get this ready for submission, ~smiles~ You know who you are. As always feel free to vote and send feedback, its always appreciated. ************* CRACK Standing behind her desk Mary Elizabeth watches as the girls turn around in their desks looking for the source of the noise. Nodding to them she starts to greet the class when she notices Jacquelyn in the back... cell phone on and chattering away. Making her way from behind the desk leaving the ruler on the edge of it Mary moves towards her. ”Gimme the phone Jacquelyn” Holding her hand out Mary looks down at the girl. Glancing up at her teacher Jacky (as her friends call her) pointedly looks at the hand out then turns a bit and goes back to her conversation. ”Well Tammy, daddy just promised me he would buy me that red miata, and you know him he never goes back on his word” Sighing with exasperation Mary taps Jacquelyn on her shoulder trying to get her attention, she never realized when she was in college going for her teaching degree how much trouble some children would be and it makes her almost wish daily that she had become a nun instead. Rolling her eyes Jacquelyn sighs loudly “hold on Tammy, Ms. Livingston is bothering me again.” Turning back to her teacher she gives her a dirty look. “Do you mind Ms. Livingston this is an important phone call and you keep interrupting me.” What a bitch she thinks. ”YES I mind Jacquelyn you are interrupting class and I would appreciate it if you would end your call and pay attention. If not I will be forced to send you to Headmaster Stockton.“ Laughing Jacquelyn places the phone again at her ear. “Yeah Tammy, I need to go I think I am going to be sent to the headmasters office, yeah I am so scared to” Looking over at Ms. Livingston she rolls her eyes in a smart aleck way and says her goodbyes. Shaking her head Ms Livingston gives up, Picking up Jackys books she hands them to her and points to the door. ”Jacquelyn please go to the headmaster’s office, I will be down shortly to explain to him what happened, till then you can wait.” Muttering under her breath Jacky stands up yanking her books to her chest covering the insignia of the private all girls schools uniform she is required to wear, tugging her shortened skirt down she makes her way to the door.. Turning and taking a bow to her classmates she makes her way out the door shutting it behind her, closing out the sounds of the giggles from her exit. ---------------- Yawning Jacky swings her legs in the chair as she awaits the headmasters call into his office. After what seems like hours the door opens and Headmaster Stockton crooks his finger at her motioning her in. Gathering her books Jacky stands up and arrogantly makes her way into his office with a swish of her hips and barely able to hide her contempt of this man and the teachers here. Looking around the office she sneers at the decoration thinking that her daddy’s office was more tastefully decorated and that he the headmaster must not be paid much if his room looked like this. Watching Jacky, John Stockton sits behind his desk and sees the expressions cross her face, with an inward grin he realizes that he will enjoy what happens next. ”So Miss Bonaparte just why are you down here at my office today, surely it’s not on a sightseeing tour.” Laughing to himself he watches her squirm as she realizes he saw exactly what she was feeling upon her face. ”I didn’t do anything wrong Headmaster Stockton, Ms. Livingston rudely interrupted my phone call and then sent me down here, I see no reason to stay, it’s her you should reprimand. With those words Jacky stands grabbing her books and turns to leave. ”Stop” the voice was quiet but firm and to her surprise Jacky feels herself stopping in her tracks and turning. ”Now sit! We will wait for Ms. Livingston to come in; it’s nearly the end of class.” Backing into a chair and sitting down without realizing it, Jacky watches as the headmaster ignores her and turns to the work on his desk. Head down but eyes’ resting on her, Headmaster Stockton watches her as she squirms; he figures it’s probably the first time she’s ever found herself listening to someone. He had read her personal file when the secretary had informed him she was waiting, and had seen notes from the other teachers about how difficult she was. Smiling he wondered how long it would take to wipe the smugness from her and replace it with proper respect. Lifting his head he watches as the door slowly opens admitting Ms. Livingston. Smiling at the headmaster she takes the other chair slowly and quietly. Good Afternoon Ms. Livingston it’s a pleasure seeing you again, you sent Jacky here because….?” He left it hanging watching Ms. Livingston squirm a bit, probably He thinks, remembering time she was here last, and finally she raises her head and nods. ”Yes Sir, she was interrupting class by talking on her phone and then when I asked her to hang up she was very rude. I sent her to you for you to take care of.” Grinning broadly he nods at Ms. Livingston then stands and moves out from behind his desk making his way in front of Jacky. Standing there so close makes the girl crane her neck back to look at him. Well Miss Bonaparte I see we have a problem and we have 2 solutions.” Grinning down at her “We can either punish you in front of the whole school letting them know how inappropriate it is to talk on your cell phones in class OR we can see to your punishment here where only Ms Livingston and I will know of it, which would you prefer?” Staring definitely up at her headmaster, Jacky could not contain her anger any longer she had seen other girls take the public punishment and would not let him think he could get away with doing the same to her. Imagine him, thinking he could force her into this. He had another thing coming. ”I was talking to my friend; my daddy gave me the phone and said I could use it whenever I wish and I wished to in Ms Livingston’s class. Its not my fault she’s boring and I have to keep myself awake. As for your punishment, you just try and I will tell my daddy and he will have your job.” Smiling at this spitfire Headmaster Stockton shakes his head “No I don’t think your daddy will find out because if you tell him I will be forced to tell him some things as well, such as how you have been smoking in the girls’ bathroom and sneaking out to see that boy your father warned us about.” Groaning Jacky slumps in her seat, she was sure she hadn’t been noticed as she snuck out of her first floor dormitory room to see Keith. He is so cute and dangerous, which Jacky liked and most of all she had not yet had a chance to go “all the way” with him. ”Now Miss, Bonaparte which will it be, punishment here or in front of the school?” Crossing his arms Headmaster Stockton stood there awaiting her answer, sure of what she would say. ”I will take punishment here Sir.” Saying the words made Jacky’s mind reel in wonder of what her punishment would be, she never had been punished in her life, her mother had died when Jacky was 3 leaving her father and the housekeeper to raise her, and neither had ever said no to her. Almost forgotten Ms. Livingston, Mary Elizabeth, sat quietly in her seat watching both with riveted eyes knowing what was to come and finding herself waiting with anticipation. ”Good choice young lady, why don’t you stand and make your way to my desk, then lean over it and grasp the other side with your hands, NOW!” Jumping at the tone of his voice Jacky was up before she realized it reaching out over his desk hooking her fingers over the other side and digging into the crease as her well endowed chest presses against the wood rubbing her clothe covered nipples against the hard surface. Gazing at the site before him, Headmaster Stockton moves over behind her then turns and nods at Mary Elizabeth to lock the door. Moving quietly but with much grace she walks to the door locking it and returns to her seat. Smiling he turns back to Jacky admiring her ass as it wiggles under the skirt, the desk pushing it up cutely as she laid over it. Reaching out with one hand he lifts the skirt draping it over her back. Hearing her gasp of surprise only makes his job that much more pleasurable. The white panties strained against her perfectly curved ass accenting it and moving with each wiggle she makes. Grabbing the waistband in both hands he drags it down her legs causing her to struggle. Reaching out with his right hand he brings it down hard on one cheek. ”Stop that! I didn’t tell you to move” Growling he places one hand on the small of her back holding her in place as he begins to swing, his hand landing on her ass once more, then again. The loud smacks echoing in the small room. ”What do you think you are doing Headmaster Stockton? I will have your job for this; I will tell my girlfriends and make sure they tell their parents what you are doing.” Sputtering out her anger Jacky strains against his hold trying to get loose, jumping and crying out with each smack to her ass. ”Shut up Jacky! You chose this punishment and if you so much as tell one person about it I will tell them you came onto me and when I told you no you went out threatening me, and remember I have Ms. Livingston as a witness. Then we shall see who they believe.” With those words he grabs a paddle under some papers on his desk and starts to swing it landing each blow in a different place from the last watching as her skin reddens from the impact. Turning his head a bit he looks over at Mary Elizabeth noticing her squirming and wondering if she was remembering the last time he did this to her, reliving the pain and pleasure she learned to get from it. Motioning with the paddle he watched her stand obediently and move next to him, as he resumes the spankings. He moans to himself as he watches Jacky’s flesh ripple with each crack to her ass, her thighs and ass red and hot to the touch, her body squirming in-between each blow as she cries silently now. Dropping the paddle back on the desk the headmaster stands there for a moment, delighting in the sounds of Jacky’s cries as she sniffles and whimpers shifting positions to try and ease the pain she is feeling. Smirking he reaches out pinching one of the welts that were raised on her ass hearing her gasp as the pain shoots through her body. Moving his hand a bit lower he slides his fingers between her thighs feeling the wetness dripping there. Unable to resist he presses his fingers between her aroused lips searching for her clit and hearing her gasps of surprise and pleasure as she fights with herself at this utterly wrong thing her headmaster was doing. Moving her legs slightly apart Jacky wars with herself feeling Headmaster Stockton’s fingers causing a sensation to start low in her belly, and yet she knew what he was doing was wrong. Shaking herself Jacky sputters as she loosens her hold on the desk. Standing up she turns to face the headmaster with a fiery look on her face. ”This has gone too far Sir, punishment is one thing but this is far different, I am calling my daddy NOW!” trying to cover herself again with her skirt Jacky had but a moment to stand before she felt herself getting spun around and forced back against the desk, a hand planted on her lower spine and her legs being forced open farther as she fought to get loose. ”Listen and listen well Jacky, I am the headmaster here and I tell you what goes, you will learn respect and courtesy if I have to beat it into you, as a matter of fact, that sounds like a wonderful idea.” Holding his hand on her spine he motions to the desk and gives Mary Elizabeth a look she knows all to well. Mary Elizabeth Immediately knows what he is expecting of her and feels herself grow damp, it had been so long since she had done this, and probably the last time she had been in the headmaster’s office at the same age Jacky is. Mary Elizabeth slips out of her panties and moves to where Jacky’s face is, still sputtering and cursing as she fights against the headmaster’s restraint. Standing at the edge of the desk Mary waits for John to pull Jacky back by her hair then slipping onto the desk opening her legs wide for Jacky to see. Feeling as if her hair is going to be ripped from her head Jacky stops bitching for a moment and then watches stunned as her teacher, the one she despised the most, the most prim and proper teacher she has crawling onto the desk, her pussy wet and open as her legs are stretch wide. “No no, please don’t Sir please don’t,” Jacky shakes her head as she begs and pleads realizing what is about to happen. ”Ohh yes my lil slut, its only right that you pleasure Ms Livingston after making her day so hard.” Grinning Headmaster Stockton pushes her roughly down pressing her head against her teachers’ pussy, rubbing her face against it as Miss Livingston moans and takes control. Holding Jacky’s hair is all Mary Elizabeth can do as she thinks of how hot Jacquelyn is. Wishing she were in the girls place, and just once more that she could feel the headmaster using her body as he was Jacky’s. Rocking her hips she grips the younger girl’s head tight between her thighs, not caring if Jacquelyn did anything with her tongue, and using her student’s pert nose to stimulate her clit Mary Elizabeth loses herself in the pleasure. Grinning at the two women John grabs the paddle and smacks Jacky again, the force of each blow making her face press tighter into her teachers’ pussy, masking her sounds and complaints. Tossing the paddle down finally John gives into his lust, pulling out his 8 inch cock that had been straining against the fabric of his pants and underwear. Letting out a groan of pleasure he then takes it in hand as he steps up behind Jacky then slides the fingers of his other hand in and out of her pussy making sure she was wet and ready for him. Moaning in disgust and more then a little desire Jacky feels Miss Livingston’s pussy press against her face rubbing against her nose and leaving the musky wetness behind. As she goes to protest her mouth opens and she’s almost gagged by the unfamiliar taste and wetness sliding across her lips and tongue. She jumps again when she feels the blows sting her ass causing Miss Livingston’s pussy to be forced harder against her lips and tongue. Jacky is unable to get loose and starts to shake as she realizes that even with all of this she was getting turned on. Turned on more then her b/f could do, and turned on by a pussy and spankings. She moans in pleasure as the beatings stop spreading her legs more as her headmasters fingers start to explore her insides, her willingness to fight slowly seeps out of her as Jacky lets go and begins to enjoy herself. Pressing back against the headmasters fingers Jacky starts to moan with desire trying to show him how much she was enjoying that, ”Well she is a slut, just as I thought” John thought to himself as he grabbed his cock one more time lining it up to her pussy and with a nod to Mary Elizabeth he shoved it deep into the young women in front of him, hissing in pleasure as his cock sinks into the velvety softness of her. The tight pussy milks him as he pulls out again then shoving back in he reaches around grabbing the small breasts in hand. Lifting her a bit he watches Mary Elizabeth hold her head to keep Jacky in place as she pleasures herself. Jacky torn between the pussy in front of her and the hard cock fucking her from behind feels her orgasm climb higher without any touch other then the cock and breasts. Digging her teeth into Miss Livingston’s lips she starts to bite and gnaw, her tiny teeth finding the clit then hearing the cries of pleasure come out of her teachers’ mouth. ”OHH yes Jacky that’s it, fuck me with your tongue and bite my clit, oh god I am going to cum... Ohhhhhhh…..” Mary Elizabeth cries out holding Jacky’s head hard as her hips move covering Jacky in her pussy juice as she orgasms. Her thighs locking around the younger gals head as she shudders through her pleasure. Moaning at the site in front of him Johns hips speed up, his own orgasm imminent as he feels the younger beauty under him, pinching her nipples and fucking that hot pussy. Finally letting out a bellow John shoves himself in deeper feeling Jacky spasm around his cock milking the cum out of him as he jerks over and over in her unloading his cum deep in her pussy and making his legs weak. Jacky feels John speed up; her own body’s response takes her by complete surprise as she orgasms with her Headmaster, her first orgasm without her fingers doing the work. Gasping and shuddering she feels his hot cum end up deep in her body all she can think of is how much she loved this and how she can get into trouble again. Mary Elizabeth lets go of Jacky’s head pressing it lightly to her thigh letting the young girl catch her breath as she herself caught hers. Looking up she watches as John stirs, pulling himself off of Jacky’s back where he had slumped after his orgasm. Smiling at Mary Elizabeth he slowly pulls out of Jacky and makes his way around the table holding his cock up and nodding as Mary Elizabeth leans in taking it and sucking it clean making sure her tongue covers every inch. ”Yes just like old times” Thought Mary Elizabeth. The Headmaster After parking across the street from the aging brick building, I look both ways and make the sprint. My bag is heavy with gear but it doesn't slow me down. It couldn't possibly. I am here. The dark stairwell leading up smells of sweat. Probably somebody cleans it once in a while, but it will always smell this way. That's because the dojang is a sweaty place, and... that's a good thing. In the women's locker room I strip quickly. My hair is already French-braided so I don't have to worry about that. On with the sports bra, the uniform. Then my belt, the blue stripe. Any day now I will be called to test, but I really don't care about that. What matters is the sweat. I tie the belt correctly, high color on the right, grab my bag and get to the mat. I'm early but there is no time to waste. Being past thirty means the more time spent stretching, the better. Eighteen months ago one of the black belts took me aside. "Don't forget." he said. "You never stretch a cold muscle." I haven't forgotten. My gear bag gets tossed in a corner and I start running laps. It is wonderful to feel the easy way the air moves in and out of my lungs, feel my thigh muscles waking up and saying thank you, thank you for using me. A dozen laps clockwise, a few more counterclockwise, and I'm nice and tacky. I plop down then and spread my legs as far apart as they will go. I'm not rail-thin the way I was when younger, but more shapely, with better muscles. Stretching, ah, twisting at the waist, bending my nose to my shin. Left, center, right, center, chest to the mat, arms spread wide... Laura comes in and we do some partner stretches. Her legs are longer than mine so I push the soles of my feet against her ankles. "How's life at the bank?" I ask. We stretch in opposite directions: my hands reach to her left ankle, her hands go to my left. "Same ole, same ole," she answers. "How about the college?" "Fun week," I grunt. "Started inspecting hospitals." I explain that we do that for the sake of the medical students' education, and she laughs. "Will you push down my knees?" she says. Of course. We take turns kneeling behind one another. She pulls the soles of her feet together for the butterfly. My arms come around and lightly, carefully, I press down on the knee joints until she spanks the mat. Then she presses my back, something I really appreciate, because the hip joints need that precursor if I'm going to kick anyone in the head. Which I plan to do -- in a friendly way, of course. My legs can spread wider now. Laura gently but firmly leans her weight against my upper back. I can feel my boobs squashing flat on the mat. My hands grasp at the air in front of me. "Inhale," she directs. I breathe in, then, "Exhale," and she presses a bit more as the breath whooshes out of my lungs. This works. I love it. "Thanks." I tap the mat, and she nods, and lets up. Other students have been trickling in. Rick and Jacob, the Burke twins. Not my favorite people. Carol Martin, the matriarch. She is the oldest student. Andrea, a trusted friend. Adam, strawberry blond and green-eyed, he's hot. I wouldn't mind a few partner stretches with him, but he's never shown any interest, and I don't feel like making the first move. Three white belts. Couple of yellow belts. The lead black belt claps his hands sharply. "Let's line up!" he bellows, and the twenty-five or so students scramble into place, lined up by rank. I'm in the middle of the pack. Everyone faces forward for the opening ritual. Bow, salute the flag. Bow, to the headmaster. Bow, to the black belts. My long dark braid slides over one shoulder. The headmaster barks out the official warmup. "Move your hips!" the old man snaps out. Off the mat, he is the nicest guy you'd ever hope to meet. Students universally adore him. On the mat, you'd better do what he says, or brace yourself for a solid kick in the ass. The forms begin. "ONE!" comes the command. My left hand shoots out to the side, a sharp knife-hand. I make the horse stance. There are many ranks in the room, so the person behind me does something different, the person in front of me does something else, and to my left, something still different. In the frieze we look like some odd modern dance. "TWO!" Down block, turn ninety degrees. My eyes don't go anywhere but where they should. Back straight, wrists straight. I'm completely focused on my invisible target. "THREE!" For a second I wonder if he ever gets hoarse doing that. After each count, there is a slight pause while the teacher looks over everyone's form. Sometimes he corrects someone, and the pause is a bit longer. Out of the corner of my eye I see the black belts helping the white belts. At step seven, my block isn't what the instructor wants. The whole class pauses while he steps over to demonstrate. No words are spoken. He realigns my shoulders, a warm, reassuring touch. Then his uniform snaps like a sailcloth in the wind. I do my best to imitate the master. He does it again. I do it again. He gives me the keep working on it look. The sweat is pouring down my body. Of course I will. The count proceeds. At step twelve, I do something I'm not supposed to do. The form calls for a kick that I just don't agree with, so I change it. It's dumb to kick with the toes extended! I've always been taught that's a great way to get your toes broken. So I change it, and strike with the heel. The headmaster notices but doesn't correct. So I keep doing it. This is brash, and in a few moments I'll probably get a lesson. Stubbornly I tell myself I don't care. At step eighteen, many of us are finished. We hold the last position, stock-still except for the panting and sweating, while the advanced ranks continue to follow the count. I'm lucky. The poor white belts have to stand still for a long time. I get to keep moving twice as long. The count finally rolls to 36. My heart rate is decreasing. Then something odd happens. The headmaster gives a rare command. "Gather around. Sit down." Most us kneel, palms on our thighs, to show respect. One of the white belts is observant, and follows suit. The rest will, in time. If they stick around. "I need to raise a delicate issue," the old man continues. Involuntarily I shudder. The upper ranks' faces are impassive, but their eyes flicker. Something or someone has annoyed the man, and they don't like it. "How many times," he asks, "have we talked about setting goals in this class?" He looks around. "Mr. Burke?" "Many times, sir," comes the answer. "That is correct. Where are goals, in time?" I raise my hand and he nods in my direction. "The future," I say. "Again correct," he affirms. "But for the next two hours, I want you to stop thinking about your goals. Why is that?" No one can answer. He looks into each face. "Daydreaming!" he finally snaps. "When you are in the future, you are not here. Because the future has not happened yet, you are not there either. "You must pay attention to the here and now. It is through daydreaming that you are distracted. It is through distraction that there are injuries. There will not be any injuries in this class. Do you understand?" Everyone nods, basically too terrified to speak. A few mumble yes, sir. "What?" "Yes, sir," is the loud chorus. "Good. Where are your minds today?" "Here and now, sir." Satisfied, the headmaster stands. He orders the lineup, by height this time, for sparring. He catches my eye. "Miss Crane," he says curtly, and points to the ground in front of him. I jog over and stand formally, eyes down, while he gives the rest of the class orders to spar. "Now," he turns to me, "tell me why you changed your kick." I tell him I think the kick looks like a pretty ballerina. "Uh-huh," he grins. There is a twinkle in his eye, which lets me know I can relax a bit. "Now think about your form," he instructs. I do as I'm told. It is in my mind. "What do you think is happening, here?" "Breaking a board?" I try. Shake of the head. "Striking an opponent?" No, that's not it. I feel like a dufe. "One-step sparring," he orders. "Kick my balls." My head rolls back and I choke on a laugh. "I can't do that!" But he motions me into position. "Attack." I step forward and swing my fists into place. "Ay-yah!" He steps backward and repeats the salute. Then I kick viciously towards his crotch, striking with the heel. In less than one-tenth of a second, the pretty ballerina foot loops up, catches my leg and neatly flips me onto my back. I land with a loud whump and barely remember to slap the mat. Some of the shock is absorbed but I am dazed. The shapes in the ceiling plaster look like a horsey ... a duckie ... the Mona Lisa ... The forearm that enters my field of vision has grey hairs on it. The hand opens, grasps mine, easily pulls me to my feet. "Pretty ballerina," he snorts. "Never heard that one before." The next ninety minutes go by too swiftly. By noon my arms are trembling from sparring and push-ups. My sports bra is glued to my skin and I smell like a goat. I have never been so happy, except of course for last Saturday at this time, and the Saturday before that, and the one before that. In the women's locker I elbow to my place between Carol and Andrea. "So, Miss Greene," I ask, "lunch?" "Nah, not today. Kids." "Oh, too bad. We'll miss you." "Yeah, maybe next week." Laura's coming, though, and Carol. Some of the guys will, don't know who yet. Knowing isn't critical. We get through the shower -- hot, delicious, lathery, soapy, it feels so good -- and combing our wet hair, we walk across the street to our typical haunt. I order an egg salad sandwich on whole wheat, and freshly squeezed orange juice. There is nothing like feeding protein and whole grains to a body that is alive with exertion. You feel like you could just about levitate, if you tried hard enough. Only half a dozen of us make it to lunch today. The headmaster is at the opposite end of the table from me, too far really to engage in conversation. But our eyes meet from time to time and our friendship is easy and warm. I really respect that man. After lunch I am checking my tires before the long journey home. One of them seems a bit low, I think, and I hook up the portable compressor. While it's whirring away, I floss in the driver's side mirror. "You might want to keep an eye on that," says a voice, and I jump. Quickly I yank the floss from my teeth, flash a grin and hop out of the car. "Oh, it takes a minute. Aren't you headed home?" My teacher seems at a loss for words, something I have never seen, and finally he says, "I want to talk with you. Care for a beer?" "Ah, sure." I am puzzled and surprised. He names a pizza place on the other side of town, and in our separate cars, we drive over. "So," I say. "So," he replies. Across the table in the dim restaurant he looks just like somebody's dad, or somebody's grandfather maybe. His shoulder-length hair is all grey, going white. It is impossible for me to tell what color it might have been. He touches my face, runs his fingers gently over my mouth. "Did I hurt you today?" "No, sir," I say quickly. "Good." He pours us each a beer. I am starting to get the picture or what I think is the picture and my mind is filled with images of his body in the dojang. I am remembering the hundreds of times he has moved my limbs into position and the gentle strength in those touches. Thoughtfully I sip my beer. "You know I'm not married," he begins. *** It's Wednesday night. For the first time in ages I am skipping class. The clock reads 8:55 and I stroll softly around the room, lighting candles and sipping a little wine, trying to remain calm, but my palms are sweaty and my stomach is jumpy. He'll be here any minute. With a sigh, I stretch out on the couch. I'm aware of my skin, newly clean, and freshly shaven in so many places, cocooned in a silk kimono. Usually this attire is a treat just for me, to wear for meditating after a scented bath. Tonight it's for someone else's pleasure, too. The anticipated knock skyrockets my heart rate. I drop the magazine I couldn't read anyway and rush to the door. There he stands. This is real. Hands shaking, I put my fingers in his and draw him in. "You came," I whisper in shock. He leans in close, his beard tickles my neck and he plants a quick kiss. "I expect we both will," he says in my ear. I have to laugh. My nervousness drops away as he pulls at his jacket. "Wait," I say. "Dance with me first." Sade is asking — Is it a crime? We sway in gentle steps, my bare feet adding to the feeling of lightness. My lover strokes my back and caresses my butt. "I have always wanted to tell you what a glorious ass you have." "Thank you." The aroma of leather fills my nose, I breathe it in. My hands do a little squeezing, too. "So do you." Against my tummy, I feel his cock jerk in his pants. I want you to want — me, too — pines the music. His mouth falls to my neck like a shooting star and my legs forget to move. Our breathing sounds faster and he pushes the silk away from my shoulders. My skin pinks and he murmurs his appreciation. His beard scrapes over the tender skin, languorously working south of my neck. Red marks appear and start to swell a little. His knowing fingers untie my obi without any difficulty and he lets it drop. The kimono is just a loose robe now, wide open to the longed-for attack. I hang onto the soft leather armor for dear life, bending backwards as he makes his way to the swell of my bosom. His forearm makes a steel bar at the small of my back, and he leans to nuzzle the lace of my bra. The half-cups offer up what I have to give, barely covering my nipples. The pink aureoles are clearly visible and he homes to the target, his hand dipping in to rescue my left breast. "Ah!" is all I can gasp out, and then his tongue is on that delicate peak, electricity bolts through my system, and my knees turn to water. He has held me before, caught me when I fell, but never like this. "My nipples are very sensitive," I explain as he lowers me to the sofa. "So I see." His eyes glitter with lust and good spirits. His beautiful mouth descends to mine. I suck his tongue as if it were his cock, demanding, flicking the underside with the tip of my own. My hand finds his hardness and strokes the length. I caress his huevos, squeezing gently. He breaks the kiss. "Stephanie—" he pleads. "Way ahead of you, brother." We leave the saxophones in the living room and I lead him down the hall. My bedroom is plain, but illumined by candles. I tug his shirttails out of place. Now it is my turn to run my hands over his ribs: to feel, to explore, to appreciate. The buttons give. How many times have I noticed his chest in the vee of his uniform; how many times have I felt those abs, sparring, training, making me what I am? Now I openly caress his belly, his breastbone, and lay my lips to that fine smooth shoulder. With the tip of my tongue I circle his nipple, press hard. To my satisfaction, he draws a sharp breath in response. Against his body I speak softly, "You are wearing far too many clothes." I keep nipping and kissing his torso while together we shuck his pants, the particular sound of the zipper like a clarion call in my ear. He peels off his shirt and I push him to sit on the bed. My face is in his underwear while I untie his shoes, yank them off, and away with those damn socks, and toss the black jeans anywhere, out of the way. I keep my face in close contact with those low, tight briefs, humming with happiness, letting him feel the alto vibrations all over his shaft and balls. He strokes my hair, a gesture both selfish and thankful, encouraging the ministrations. Suddenly I begin to laugh. "What!" he exclaims. "What's so funny!" I look up in mischief. "College days," I smirk. "There was a group of guys who called themselves the 'Pink Helmets.' This is what they were talking about." I lick the crown in question, savor the tiny drop of fluid, and slip my fingers under the leg elastic. My palms are flat against his hips — those marvelous hips — and I slide my hands around further, skin upon skin, gripping those handsome cheeks, until he is sitting on my hands. A simple move up, a light tug down, and finally, he is naked in my bed. He lies on his side, resting on one elbow, looking up at me as I get to my feet. I pause. In the candlelight I look him over frankly. "You're gorgeous," I tell him. "You're so beautiful." I coast my hand over his bodyscape, trail my fingers over his thick stylus and up, up to his mouth. He bites and tongues my digits. "You're not so bad yourself. Come here, woman, keep me warm." Willingly I comply. I spread the kimono like a pair of silken wings over our bodies, and slide my arms free. Our hands get busy. He finds my bikini underwear and without fanfare, simply rips it off and throws it away. I shiver with delight. The full-length, full-body contact assaults my brain. We savor the complete nakedness, eyes reflecting simmering desire in the half-dark. I taste the sweat at the hollow of his throat. His callused hands pet my body. He grips my hips and guides me to straddle him. We both groan at the sharp, intimate touch. My wetness is hot against his wood and he lifts my body, as if I weigh nothing. "Yes, move me," I implore him. My voice is husky with passion. "Move me the way you want me to go." I give him full play to my limbs and he spreads my legs wide so I am doing the splits, my toes poking out to the sides of the bed. "Come here," he orders again. I lean forward, finding our kiss again, and his thumbs rub over my nipples, not too gently. "MM!" I moan against his lips. He has quickly learnt my fine points. He keeps teasing the delicate nubs, driving me wild while he sucks my tongue, plunders my mouth. I am going under, drowning in the flames. His hands go everywhere, stroking my thighs, my ass. He pulls my ankles up to his shoulders. Our abs press together. His prick is horizontal in my trench and with just a wriggle ... just a twitch, he could slip right in. I start to move. But he rolls us over, and keeping my legs on his shoulders, shimmies down my belly. I clench at what's to come, shudder and buck as his kisses sparkle over my hips. My arousal is dripping down over my perineum, slicking the crack of my ass. He wastes no time in licking that vertical path and I wail a keening cry. I clutch at the bedclothes, my hips jerking under his strong hands. He holds me firm while he makes love to my labia with his tongue, suckling, penetrating my secret places, pursing his lips in a passionate kiss to my clit. He takes his time, nosing my muff, exploring every fold and valley, thrusting deep inside. I can't stand it, I can't stand it. I am writhing in pure animal pleasure that builds to erotic torment. I find myself saying out loud, "I can't stand it!" How did he get that latex on? I have no idea but urge him up, calling "Please!" "Tell me what you want!" he growls. "Bang my brains out!" I pull him to me, urgently. "Fuck me!" He does. His penetration explodes a sharp gasp from my lungs. Oh, goddess! A perfect fit! The ride is hot and hard. His balls slap my ass and the spanking drives me higher still. Our eyes meet and hold, lasers of pure lust connecting. Then we look down to watch his cock pounding into me. Bang... bang... bang... bang. The sight sends me over the edge, I lose it completely. Somewhere a woman screams "YES! YES!" and release courses through me, thunderous and sweet. His own is a heartbeat later, his eyes shut tight, his guttural roar filling the air. My hips lift to meet him, my back arches like a bow. Again and again he spurts his liquid fire, jabbing at my insides, pounding his awesome strength into my being. The Headmaster Finally he slows, stops, collapses on my chest. "Hmmmm," he chuckles. We roll apart just a little, panting, his head still on my shoulder. He reaches for my slit, stroking the wet, sticky flesh. "Do you need more?" I love a man who is courteous in bed. "No, thank you." I gently push his hand away. "Too sensitive right now." "Ah," he assents. "You are satisfied, then." I let out the breath I didn't know I was holding. "O, yes." It's worth saying again. "O, yes." Quietly we lie together in each other's arms, our breathing steadying out, soaking in the afterglow. Little by little, the dizziness fades, my senses regain. The soft blue LED numbers tick to 11:00. It's been a delicious two-hour fuckfest, time that slid by in a blink. Some of the candles have died. Pleated at the foot of the bed for this moment is an organic cotton sheet. I pull the tender weave over us, stroke his back and cuddle him, as women do. I think he is falling asleep on my shoulder. This is so pleasant and warm, but it's a weeknight. I brush aside his beautiful long hair. "Master," I speak softly. He looks up, fully awake. He puts his fingers on my lips. "Rob," he says. "My name is Rob." He looks at me. "Say my name." Warmly I hug my friend. "Rob." The Headmaster and the Pupil The characters in this story are consenting adults. St. Ann's School exists in the imagination of two creative lovers. If you enjoyed reading these characters as much as I enjoyed writing them, please leave suggestions for what you'd like to see them up to next! ***** -The Headmaster- "WHAT am I going to do with you, Miss Connolly?" I sighed heavily as I pushed my chair away from the desk, dropping Sister Catherine's latest write up of Megan Connolly in exasperation. She was one of the most difficult students to deal with at this school. Bright enough, B+'s and A-'s across the board, admired by her peers and truly a sweet girl. The very same one who baked Sister Brigid cookies and brought flowers when her cat died. But, even at 18, she just could not put up with even slightly strict authority figures, as her latest snarky remarks to Sister Catherine, one of our older school instructors, showed. And having met Mr. and Mrs. Connolly, I could see why they sent Megan off to join us every year. "I could probably charge them double tuition and they'd pay it in a heartbeat," I said aloud, to no one in particular. I decided to take a walk to clear my head, or maybe find some inspiration as to how to deal with Megan. I walked out into the beautiful Indian summer afternoon, wandering the sprawling campus. Whether by accident or by design, my legs carried me into a small grove in the wooded area at the western edge of the grounds, a beautiful, sleepy, secluded spot I would come to to escape from my office. I doubted most people at St. Ann's even knew about this place, and I was perfectly happy to keep it that way. When I got close to the grove, I heard an unusual rustling sound. Concerned it might be some kind of animal, I slowed down and crept gently toward the clearing. What I saw made my jaw drop. -The Pupil- God, I was so wet. I pawed my left breast as my other hand ran quick, gentle rings on my clit. I needed to get off so badly, yet I was happy to take my time. Not very often I could draw out a masturbation session like this in the dormitory. I'd been to the brink three times now, backing off the precipice each time. Nothing felt quite as good as releasing all that tension after edging myself like this. Sometimes I'd even see how long I could hold out before losing control. My personal best was 15. I shrugged off my blouse and dropped my bra to the ground, giving myself unfettered access to my medium-large, tear drop boobs. I decided to cool myself down some, and stopped rubbing my clit and gave attention to each breast. Four times to the brink of orgasm now, I thought I'd settle in and see if I could break that record. That changed quickly. "MISS CONNOLLY!" My eyes flew open as I sat bolt upright, frantically trying to cover my exposed breasts with one arm as I pulled my skirt back down over my groin. Headmaster Duncan stepped into the clearing. "Just what do you think you're doing??" He asked angrily. "I-I-I...n-nothing Headmast-" "Save it. Do you think this is conduct benefitting a St. Ann's lady? I come here to figure out how to deal with your latest back talk and THIS is what I find? I felt my skin burning hot and tried to stammer out a response. "Quiet. You know you have to be punished, yes?" I nodded sheepishly and looked down. "Stand up, Megan." I looked back up, eyes bulging. "Stand UP. Don't make me ask again." I stood up, using my arms to cover my breasts. "Please," the headmaster said bitingly, "don't feign modesty with me now. What I just saw was anything but modest. The headmaster's tone was commanding, I wasn't about to argue. I dropped my arms to my sides, averting my eyes. -The Headmaster- My eyes drank in her young, lithe body as she stood there trembling slightly. Long, honey blonde hair framed a classically beautiful face, with big blue eyes and the faintest dusting of freckles. She gnawed her big, pouty lower lip and she stared intently into the dirt. Her big, full, pert breasts stood proud on her slim frame. Short, fat, succulent pink nipples capped off each one. Her long torso had a taut, firm belly that led to the low waist of her "regulation" uniform skirt, sitting askew on her hips. "What were you just doing, Miss Connolly?" "T-touching myself, Sir." I nodded. "Sins of the flesh are tempting, at your age. Why were you touching yourself? You're a bad liar Megan, so don't try to pull anything past me." Her eyes drifted off into memory. "I was with Bobby Riordan, sir." "And?" I asked sternly. "We...kissed." "You're a bad liar Megan, that includes not telling the whole truth." "He touched my breasts sir." After a beat she added, "Under my bra." "And what else?" "He...he wanted to touch me, under my skirt sir. But I stopped him, honest." "He tried to touch your pussy." The word seemed an electric shock to her. "Let me hear you say it." "He tried to touch my...pussy." "Better. It's good to know you have a modicum of self control. Take off your skirt Ms. Connolly." She froze. "Take off your skirt Megan, you won't like it if I do it for you." That hurried her right along. She wiggled her skirt down to the ground and stood in her simple pink lace cheeky style shorts. They were noticeably darker in front. "Those too. Be quick about it." Automatically she reached for her waistband before freezing there, seeming to only realize what she was doing at that moment. I closed in on her and touched her for the first time. Getting right up in front of her, I grabbed the hair at the base of her head and held her face close to mine. "Listen to me. This is how this goes, I tell you to do something, and you do it. You do it quickly, and with a smile on your face. Do you understand?" -The Pupil- I nodded quickly as I looked into Headmaster Duncan's smoky eyes. He released my hair and stepped away. "Now," he said crisply. "Let's try this again. Take off your panties." This time I followed obediently, lowering my panties to the ground, trying my best to keep my knees tight together as I stepped out of them. When I stood up I felt his eyes snap to the neatly groomed little nest of dark blonde hair on my mound. He circled me slowly, dragging his gaze up and down the length of my body as he spoke, not seeming to mind if I responded or not to his musings. "Now I've always felt that sins of the flesh should be paid for and purged through the flesh. Don't you agree? It's very important that we control our urges, and not give in to our...more base sides. I'm going to show you what happens to sluts. Should straighten you right out." I jolted at being called a slut. Headmaster Duncan seemed amused. "Oooh, not fond of that name are you? Well what would you call it? Letting boys touch those breasts, and enjoying it so much you have to come outside and touch your pussy?" Again, I took to long to respond, and he stepped quickly around in front of me, grabbed under my chin and forced me to look at him. "What would you call yourself, Megan?" "A...a slut, sir." "Quite right," he said cheerily. "Now as I was saying, of the flesh and through the flesh. You were very aroused, weren't you, my little slut?" "I am - was, sir." I was shocked at the Freudian slip, but more shocked to realize that it was completely true. If I was wet before, I was positively dripping now. The Headmaster I smiled a wolf's grin as she confirmed what I suspected. She was loving this, even if she was timid about it. I circled her again and unfastened my belt. She tensed at the sound of the clasp. Seeing this, I gently touched her shoulder and said "Don't worry dear, I understand." My hand slid down her arm as I quickly fashioned my belt into two loops to hold her wrists. I secured them both tightly behind her back. Gripping her by the neck, I guided her over to the flat rock on the edge of the clearing. It was just below her waist level, and I pushed her roughly on to it, bending her at the waist. My fingertips traced the curve of her back delicately, finally reaching her plump, firm ass. Without giving her an opportunity to realize what was coming, I smacked her ass. Hard. She yelped and tried to squirm away. Reacting quickly, I made sure she knew how this was going to happen. "Ah-ah-ah Miss Connolly," I said as I pressed down on her back, keeping her pinned to the rock. "If you want to prove that you're a good girl, you're going to stay there and take this." Noticing a bright pink hand print on her beautiful porcelain skin, I gently rubbed it as I continued. "You will stay put, keep your ass up for me, and you'll thank me for the spanks." I pushed her feet a little further apart as I prepped for the next spank. *THWACK* Her ass jiggled deliciously on the impact "Thank you Sir." "Mmmm yes you are a quick learner. Excellent." *THWACK* "Ohhh yes thank you Sir!" *THWACK* On and on I went, giving each beautiful orb of her ass 15 hard smacks, turning each a violent pink. By the end, she was arching her back and pressing her ass to the sky, squirming delightfully. It was almost as if her ass was inviting each strike. When I noticed the sheen of arousal down the inside of her thighs, it was obvious that's exactly what was happening. -The Pupil- It didn't make any sense. Each smack of my bottom hurt, burned, and stung like crazy. Every one got worse...and yet... It felt good. Actually, it felt...incredible. Absolutely fucking incredible. Every touch burned through my skin like fire. My nipples cried so desperately for attention that it bordered on painful. The heat and the moisture coming from between my legs was unlike anything I'd ever felt. After gently rubbing my stinging cheeks, Headmaster Duncan yanked me up and spun me around to face him. I cried out as he suddenly pinched both of my nipples and pulled them away from my breasts. The sensations were overwhelming, and I arched my back to press my breasts closer to his hands. When he asked me his next question, my eyes flew wide and snapped to his. "Have you ever touched a cock? Remember not to lie to me Miss Connolly." Sheepishly I nodded. "Did you suck Bobby's dick?" "N..no Sir. I rubbed it until he...until he came on me." "Good girl for being honest." The headmaster gently guided me to my knees on the soft grass of the clearing. "Let's see what those pretty lips can do Megan," he said, as he unfastened his trousers. I gasped when his hardness came free. It was...big. Longish, thick, with a bulbous purple head, he looked as hard as I was wet. He stepped close and laid his length along my cheek. It was heavy, warm, and throbbing. His hand tenderly held my head, and his desire possessed me. I nuzzled his hard cock against my soft cheek a few times, eliciting a breathy sigh from Headmaster Duncan. Instinct and burning arousal took over next. I lapped the bottom of his shaft a few times, and felt his enjoyment on my tongue. Taking the cue, I slowly, gently dragged a limp tongue and bottom lip up the whole underside of his cock. As I enveloped the head in my moist lips, I tried to remember everything I heard about blowjobs, everything I had seen the few times I saw dirty videos on the internet. When I tickled that spot just under his head, the headmaster positively growled. -The Headmaster- My legs nearly crumbled from beneath me when she finally took my head in her mouth. When she fluttered the tip of her tongue on my frenulum, I had to steady myself with one hand on her shoulder. "Ffffffuck," I rumbled, as I twined my fingers in her long hair. Megan's mouth was incredible. Her big, pouty, moist lips took me in tenderly, passionately, hungrily. She sucked my cock exploratorily, but not timidly. The way she was attuned to my pleasure belied her inexperience with the act. She swept those lips up and down my length, swirling her velvet tongue in circles around my head. "Are you sure you haven't done this before?" I managed to grunt out. A muffled "mmmphhhmmmm" shook its way from her mouth to my dick, making my knees tremble yet again. She bobbed her pretty blonde head up and down my throbbing cock, working her tongue around my shaft. Every delicate suck of my electrified head brought me closer and closer to the edge. This dirty little schoolgirl had me more worked up than I had ever been. I grabbed a fistful of her hair, and Megan immediately responded to my urgency. Seeing her masturbating, the spanking and her response to it, her beautiful, supple young body, and having my cock be the first one she'd ever sucked all conspired against me being able to savor it for too long. She sucked with more intensity, tightening her velvet lips and tongue and around me, sliding my cock in out of my mouth faster and faster. "Ugh fuck, Megan," I grunted out through clenched teeth. "You love sucking my cock don't you, you little slut?" She nodded and hummed a moan that pushed me past the brink. I felt my cock tense up, my balls rise, and finally after a few more sucks, I cried out as my orgasm erupted through my body. She kept sucking as I came, keeping my body wracked with ripples of pleasure. I felt two, then three, and four big spurts of cum as I drained into her mouth. She handled the first two without flinching, but couldn't handle the volume of the third and fourth. My cum dribbled out of her patient mouth, past her still active lips, and down onto her chin. I slid myself out of her mouth, a little too sensitive for her eager ministrations, as the last of my orgasm fell onto her heaving, flushed bosom. Drained and exhausted, I eased myself to the ground in front of Megan. -The Pupil- I knelt there, covered in cum and sweat, with a slightly tired mouth, in awe of what I had just done. It was incredible to have the Headmaster so consumed by what I was doing to him, for him. To be so desired. Apparently I hadn't distracted him as much as I had distracted myself, however. His firm hand on my sticky chin startled me out of my reverie. "Did you swallow?" Headmaster Duncan's thick cum sat heavily on my tongue. I hadn't even realized that my mouth was still full, in my state of awe. I shook my head. "Show me," he said, gently squeezing my face. I quickly obliged, showing him my coated tongue. "Mmmmm good girl. Now swallow it all for me." Gulping down his thick, salty cum, I showed the Headmaster my empty mouth. The glistening mixture of saliva and cum on his softening cock caught my eye. He was...softer than he was while in my mouth, but he wasn't entirely limp, either. In fact, it looked as though he was twitching back to hardness. When my eyes fixed on his cock, it didn't escape his notice. "You liked that, didn't you, you little slut? Everything...you liked it all. Having someone see you touch yourself, the spanking, sucking me off. You're a horny little bitch, aren't you?" He was right. I had never been so desperate for an orgasm in my life. My body wasn't shy about it either. My cheeks and neck were flushed bright pink, my nipples were engorged, a deep pink color, demanding attention, and my pussy was swollen and drizzling arousal. Subconsciously my thighs had spread themselves as wide as they could while still keeping me kneeling. The headmaster's eyes didn't fail to notice this. He smirked and shook his head at me. "I know what you want next." I trembled at the words. Of course he knew what I wanted. -The Headmaster- "I'm going to fuck you, Megan." "Please, sir," she whispered. I locked my gaze on hers. "What do you want? Say it louder." "I...I want you to fuck me Sir. I want it so badly." "Mmm you need my cock don't you my pet?" This seemed to put her over the edge, she crawled to me, positively pleading. "Oh yes Headmaster. I need your cock, I need your cock inside me. Please Sir." I smiled and adjusted my belt that was binding her wrists, placing them in front of her now. I nudged her shoulders, indicating to her she should lie back on the soft grass. Kneeling between her legs, I knew I needed a little more recovery time before I could give this little minx a proper fucking. Luckily, I had just the thing in mind. Leaning forward, I kissed her flushed neck as I palmed one of her immaculate breasts. Megan stretched her bound hands up over her head, arching her back to press her firm, hot, sensitive flesh hard into my hand. Venturing down with my lips, I traced a swerving path from the ticklish underside of her right tit, as my hand squeezed her left. In quick succession, I pulled one nipple with my teeth and pinched her other. Megan yelped, giggled, then cooed as she settled back comfortably into the grass, pressing her gorgeous boobs back up at me. Repeating the process a few more times, I had her driving her hips upward at me. I simply had to taste her. -The Pupil- The Headmaster kissed his way down the right side of my torso, lingering on my hip bone. Goosebumps rose in anticipation of his lips. I was an earthquake waiting to happen. My hips twitched uncontrollably as he got closer to my desperate pussy. He kissed down to and through my little landing strip, and I moaned loudly, welcoming the glorious next kiss. It didn't come. His tongue dragged gently up my inner thigh. A loud, husky, impatient "fuuuuuuuuuuuuck," rumbled out of my throat. I had never seen this side of myself. My hips writhed as I murmured desperate pleas. No boy had ever done this to me before, but I knew that I needed it more than anything. When his moist tongue dragged its way up the length of my wet slit, my breath caught in my throat. The firm, slow pressure of his tongue on my slickness was delicious. My brain was a web of lightning bolts, my core tensed up so much it almost hurt, and my legs wrapped themselves around his strong shoulders, pulling him deeper into me. There was no stopping this. I was completely out of control of my body, utterly entranced by the Headmaster's tongue. And I fucking loved it. "Ah...ohhhh god...fuckfuck yes," I moaned and I stammered as the dam broke. I pawed each of my tits as I bucked my hips up at the headmaster. My body went totally rigid and I fell silent for an instant, until the crashes of my orgasm took over. I curled my toes as the tension in my muscles broke and uncontrollable tremors rippled through my body. I couldn't stop myself from screaming out as the climax wracked my body. It felt like it went on forever. Until I felt a gentle, insistent pressure at my electrified opening. -The Headmaster- I couldn't hold back any longer. I couldn't let her have the time to recover. I was going to give her another orgasm, and I'd be damned if I wasn't going along for the ride this time. As Megan slipped into the tail end of her climax, I repositioned and pressed my aching cock at her slit. She regained some of her senses and stared up at me, nodding slightly. I slowly slid myself into her still twitching pussy. She threw her head back and groaned as I filled her with my girth. "Oh my god, your cock feels so good Sir," she purred as pressed all of myself into her, settling there briefly. Her pussy was molten, electric, squeezing me like the world depended on it. As I started gently thrusting, she winced a little, before moaning her approval. She'd never been stretched like this before, but she was so ready for it. I started thrusting more steadily now, and her hips rose and fell to blend our rhythms into one. She whimpered urgently as her strong legs wrapped around my waist. "Fuck, Megan, you hot little slut. You love my cock, don't you?" "God yes, you feel so good in my tight little pussy. I'm gonna come again" Hearing this, I sat up, grabbed under both of her legs and pulled her closer to me, picking up my pace and intensity. Her hands flew to her gorgeous tits, massaging them as she groaned louder. Holding onto her hips, I pulled our sizzling cores together in slow, hard strokes. The Headmaster and the Pupil "Ohhhh yes...yesyesyes," she moaned. In time with my thrusts. Once again, her body coiled like a spring. This time, however, I had an incredible view of her supple young body as she built to another orgasm. Her skin flushed a deep pink, her eyes clamped shut, as she begged me not to stop. Determined to stave off my own climax until she came again, I focused all my energy on fucking her without cumming myself. She murmered more and more pleas as her hips bucked and squirmed against mine, until her mouth went slack, her legs clamped my waist in a familiar way, and again she cried out as the tension in her muscles burst. "Fuuuuuuuuuck me sir! Oh god oh god oh god" she said through gritted teeth as her body shook with orgasm. Megan's pussy clamped on my desperate cock as she came, holding me in her velvet vice. It was too much for me to bear and I pulled out of her, giving myself the last two or three strokes I needed until I growled out another tremendous climax. I erupted on her heaving, flushed bosom as she was still in the final twitches of her orgasm. I groaned out as the first few spurts shot up into her cleavage, one shot landing square on her still-hard nipple. My body shook as the last of my cum dribbled on Megan's trim belly. I collapsed next to her. - The Pupil - I regained my senses as the Headmaster's orgasm faded. I was sweaty, my chest and tummy sticky with his cum, my legs slick with mine. My toes still tingled, and I only know remembered I still had my wrists bound by his belt. My ass was still stinging from the hard spanking, and I now understood that "well fucked" soreness my friends had talked about. I felt...empty without him inside me. The whole experience was so intense and yet...I wanted it again. I wanted more. "Headmaster?" I asked huskily. "Hmmm yes, Megan?" He asked behind hooded lids. "What rule should I break next?"