A Most Wicked Headmaster (BDSM Erotica)

by Jay Merson

  She cried out softly at the feel of the hand suddenly touching on her backside, a large hand, his hand, the fingers stroking and feeling with a calm reverence. The girl stood still, her eyes still closed, bathing in the sensations as his hand roamed all over the mounds of her buttocks. She whimpered her pleasure as the long fingers teased at the backs of her thighs, edging slowly downward toward her sex. She shifted her feet apart to allow him access and gasped as the fingertips brushed against the puffy lips of her pussy.

  "Dirty little slut," he hissed, his face close to her left ear, "you dirty teasing little slut."

  She almost came; the situation, the words, dirty words and insults pushed her level of sexual arousal higher still and that increased more so as one of his long fingers wormed its way up into her wet pussy.

  "Touch your toes, whore," he breathed excitedly.

  The girl, with his finger still up inside her pussy complied, whimpering as her internal muscles clamped around his thick digit as he moved her body. She remained there, bent over at the waist whilst he pumped his finger in and out of her pussy.

  "Mmmm," she muttered and sighed, "So nice it feels."

  "Grasp your ankles," was his gruff reply.

  The girl pressed her breasts against her knees and gripped her ankles. She cried out as the palm of his hand slapped down onto her bare buttocks to send a slapping sound echoing between the high wall and the gardens buildings. Again the big hand slammed in and then again, building a steady rhythm as he spanked the girl's bare backside hard. Her body jolted under the heavy impact, the searing pain burning deep in her flesh and down between her thighs to further enflame her pussy lips.

  Fifteen times he spanked her, moving to differing parts of her buttocks on each time he landed his hand on her. It reddened and warmed her, increasing her arousal and his, ready for the sex to come. The headmaster allowed himself a long and luxurious feel of her ample breasts with one hand and a stroking of her enflamed pussy lips with the other before kneeling down behind her and kissing at her moist inner lips.

  The girl grunted and shivered as the feelings rushed through her, the heady feel and the tingling sensations she experienced were out of this world to her. She gasped as he began licking, running his tongue up and down the slit of her pussy and dipping the tip of his tongue up inside. She shuddered in pre-orgasm as he formed his tongue into a soft firm wedge, gripped her hips with his hands and then pushed fully up inside her wet tunnel.

  The girl came, gurgling and shuddering as her orgasm ripped through her, intensified by the tip of his nose pressing against the puckered ring of her anus. Throughout her orgasm and for long afterwards he licked and tasted her, dragging the flat of his tongue, cat-like, over the tip of her throbbing clitoris at times to send to even higher planes of sexual delight. It was oral stimulation of the most wonderful kind; his expert tongue had worked its magic to convince her that in future, sex without being licked simply wouldn't be sex.

  The headmaster withdrew and stood up, straightened the girl to stand also and slipped a hand under her buttocks to cup the warmed mound. He manoeuvred her to face the high brick wall and a little back from it, pressing his naked cock hard again her buttocks.

  "Hands and arms outstretched and lean on the wall pressing your palms again it," he aid excitedly, "and spread your legs."

  The girl leaned forward as instructed, her lithe body bent and her back arched to present her buttocks high. She was stretched, up on tiptoe and angled out to reach and press her hands against the cold brickwork. She gasped as he entered her and pushed fully up inside her pussy, feeding it in inch by inch until fully home. She whimpered and panted as he fucked her, her head nodding in time with his urgent thrusting. The girl pushed back against his lunges to accept the whole of his great cock up inside her.

  "Awww," she moaned in disappointment as he slowed and pulled out of her pussy. Then she tensed and cried out as he gripped her hips, pressed the head of his cock to her anus and forced brutally up inside her.

  Her back arched like a bow, the breath left her lungs in one great shocked sigh and then she screamed as the wide girth ripped her sphincter apart. The excruciating pain burned deeply through her insides, a most terrible burning discomfort and raw rubbing pain on her previously unexplored rectum. Her cries were reduced to muffled protests as one of his great hands came around to clamp hard across her mouth. She wailed pitifully into his smothering palm as he rutted hard into her, slamming his hips against her on the inward drives of his cock.

  Frantically, maniacally almost, he fucked her arse hard, with a heated sexual passion rarely found within even him. The headmaster came, squirting his warm come deep up inside her backside, emptying himself into her soft warm body. He grunted in satisfaction, good sex with a young and beautiful girl but the thrill had been defiling her most secret of places, hard and roughly.

  As he pulled out of her she dropped to her knees, her face pressed against the brickwork and sobbing her pain and misery to the moss-covered bricks. The girl, even in the darkness, covered her face to try to hide her shame as he stood over her wanking every last drop of his sperm onto her naked body below him.

  ***

  "A more civilised way to conduct business don't you think?" he commented to compliment, "Worthy of such a good looking woman as you."

  The geography teacher blushed despite her forty years.

  "Thank you she replied coyly, and gave him an admiring glance such as a love-struck teenager would give.

  They sat at the back of the vast dining hall, at a table far away from the serving women preparing for the coming lunch break. When the now silent hall would once again become be a noisy chatting and eating place rather than the quite emptiness that existed during their meeting.

  "Let me be direct with you, Dorothy isn't it?"

  "Yes, but you can call me Dot, most friend's do."

  He paused and looked deeply into her eyes, transmitting desire, sexual need and hunger.

  "I find you a most attractive woman Dot. I respect you as a teacher, as a member of the Board of Governors and as a woman."

  She giggled shyly and then swallowed hard, her expression became serious again as his piercing stare didn't waver or relent for a second. She was flattered it was obvious, interested too as the give-away little smirk portrayed. She was a teenager again, being propositioned by the boys, playing coy but beneath it all totally lost to his charm.

  "I like the way you dress, wear your hair, I like your legs, your..."

  "Please!" she protested weakly, "You're embarrassing me."

  "Why? Because I view you in a sexual way?"

  She flushed.

  "Yes, a bit."

  He paused again and rested his elbows on the table, leaning closer over to her and lowered his voice. Conveying to her is interest and desire to be close to her, his tone one of experienced knowing.

  "But it excites you also."

  The woman hesitated and replied cautiously.

  "A little, yes."

  "My lusting for you is not offending?" he probed more deeply.

  She swallowed hard and coughed, glancing nervously around her lest she should be overheard.

  "No, it doesn't offend me...and yes, it does excite me - quite a lot actually."

  "Excellent," he stated firmly.

  "Are you married? I see no ring on your finger."

  Her expression dropped.

  "Yes, I am married, does that make a difference?" she said in a hopeful voice and looked up with pleading eyes.

  He gave a broad smile.

  "Not to me," he said easily and felt his cock beginning to harden, "When?"

  She hesitated momentarily in confusion and then said as a hushed and secretive whisper.

  "The laundry rooms at the back of the kitchens, no one goes there after 3pm."

  He smiled again and felt his cock jerk in his pants.

  "Except us eh? We have a date...at three."

  ***

  The bitch was hooked, utt
erly smitten and ensnared. His approach had been right he felt; compliment the ageing woman and she would be putty in his hands. The headmaster was late, deliberately so, it was twenty past three was he walked along the corridor toward the laundry rooms. Humiliation was his aim with her, to subject the woman to sexual and mental humiliation, that thought made his already stiffing cock firm to full erection and to rub pleasingly again the insides of his trousers.

  "I didn't think you were coming," she gushed, the relief she felt obvious in her nervous voice and her manner.

  He closed the entrance door of the laundry rooms and locked it, turning slowly to face her, a sardonic grin etched on his face.

  "I command," he stated forcefully, "Always, and most certainly when sex is involved."

  She stood shocked by his abrupt and direct manner but mutely nodded her agreement.

  He circled her, deliberately silent, looking her up and down, his expression set and giving no hint as to his mood.

  "Is it sex you want?" he asked and then added, "slut."

  "Unnnh," she uttered, gave an involuntary shudder and nodded her head rapidly several times.

  He chuckled.

  "Like the man to be in charge do you Bitch?"

  The woman gave a whimper; her voice was a throaty whisper as she replied.

  "Yes, very much so."

  He pushed his chest out and moved to her front, commanding and all-powerful, staring critically at the trembling woman.

  "When were you last fucked, slut?" he said the last word as though it was bitter in taste and had to be spat out rather than spoken.

  "Oh God," she muttered, "No one has used such words for...well, for so long now."

  He chuckled mockingly.

  "In need of a cock are you?"

  She hung her head and flushed red but nodded slowly.

  "My husband and I...We don't...Haven't for some long time...well...you know..."

  "Yes or no?" he shouted loudly to make the woman start in surprise.

  "Yes!" she shouted back in nervousness, anxious not to incur the man's wrath.

  The headmaster leaned close to her face, his voice low and threatening, a mocking sneer that increased his sense of command over the nervous woman.

  "If you want my cock, you slut, then beg for it - on your knees."

  The woman hesitated for a couple of seconds and then slowly lowered herself to kneel before him. The stupid bitch even put her hands together as if in prayer and looked up at him with pleading eyes and a hopeful expression on her face.

  "Please," she pleaded softly, "please."

  The headmaster unzipped his fly and eased his stiff cock out of his trousers, gripped it with one hand and offered it before her face.

  "Good God!" she gasped, "I never thought...knew that one could be so..."

  "Like it?"

  She swallowed hard and her eyes bulged wide in amazement.

  "Yes," she said firmly and in the most decisive tone he had heard from her to date.

  "Want it do you, bitch?" he teased and began slowly stroking his hand back and forth to first roll the foreskin over the bulbous head and then back to stretch the foreskin along his huge shaft and to again expose the big head.

  "Yes!"

  He threw his head back and laughed loudly.

  "But you haven't begged for it."

  "Please, please!" she pleaded, "let me have it - give to me."

  "Where, In your pussy or up your arse?"

  She looked up at him, her expression one of utter disgust.

  "Well?" he asked impatiently, "Which is it to be?"

  "My...er...pussy," she said and moved her gaze down once again to his pulsing cock.

  The woman looked longing at the huge cock, marvelling at the size as the headmaster stood before her wanking himself slowly, displaying his cock that she needed so very badly.

  "Not good enough on the begging, slut. You will have to do much better then that. Get on all fours, like a dog, and beg some more."

  The woman didn't hesitate; she dropped forward onto her hands and knees and began her pleading once more.

  "Please let me have it, give it to me. I need it, please."

  It pleased him much to see the desperate woman grovelling, he gyrated his hips, thrusting them out to tease her more with his hard erection.

  "Oh God," she whimpered, don't taunt me, have me."

  The headmaster paused, gripping his cock harder as the excitement pulsed through him. Her pathetic pleading, her mournful expression and the fact that she was willing to grovel so in order to have his cock delighted him.

  "Okay," he said finally to break the electrically charged silence. "You can have it if you agree to two things."

  She looked up questioningly and then back down at his cock.

  "Firstly you have to pee for me, squat and pee."

  She looked up in revulsion, hesitated, looked again at his cock and then slowly nodded.

  "Secondly you have to let me thrash your backside."

  Her gaze didn't move from his cock, she paused silently for a moment and then nodded.

  "Okay," she said in a thick and excited voice.

  The headmaster pushed her further still. The excitement he felt showing both in his thick voice and the way his cock had taken on a purple hue as the blood pumped rapidly into it.

  "Only if you please me will I fuck you. Are we agreed, slut?"

  He could sense her nervousness and hesitation but her great need was overriding all else, her dignity included.

  "Agreed," she said.

  "Very well then, let me see you pee."

  The geography teacher Dorothy got to her feet walked over to the grating in the floor and prepared herself. She wriggled her skirt up around her waist, her black hold-up stockings contrasting harshly against the pale flesh of her upper thighs. She hooked her thumbs into the side strings of her panties and slid them down to her ankles.

  "Right off," the headmaster prompted, "take your knickers off completely."

  She kicked them side, standing with her skirt rucked up around her waist and her thick mat of public hair nestling between her thighs. A true blonde she certainly was not. The woman squatted, an almost obscene position with her thighs spread wide and her unusually long clitoris jutting out from the tops of her pussy lips. She blushed bright red, humiliated and shamed but so in need of sex that she would do anything to comply and to sate her gnawing ache.

  Her face contoured in a mask of pained pleasure as she grunted and strained, squeezing her bladder to empty its contents. It began as a trickle, growing in strength and flow to a thick stream of hot yellow liquid. She closed her eyes so as to hide her shame as she peed before the watching headmaster. On and on the flow went, steam rising as her body fluid jetted out to be lost down the drain grating below her. Finally the flow subsided and she opened her eyes, accepted the offered towel and wiped her pussy lips dry.

  It was a non-erotic sight to the headmaster, the bitch stood, her legs parted wide and her knees bent to spread her thighs wider still. She wiped back and forth with the towel in a grotesque cleaning of revulsion, he decided at that moment that the bitch would suffer for reducing his excitement.

  "Enough!" he barked. "Strip now and take your beating."

  The woman undressed, her head down and uncertain of her ageing body as her breasts and oversized belly came into view.

  "Seen better days haven't you?" the headmaster stated with a hint of disappointment in his voice.

  The teacher averted her gaze but nodded her acknowledgement.

  He pointed to a stack of white tablecloths to the side of the room.

  "Place your hands on the pile and bend over."

  Whilst the woman assumed the position, the headmaster took a linen pillowcase and wound it into a long and thick flexible club. He slapped it several times into the palm of his hand to test it and delighted in her fearful whimper in response to the wicked dull thud it produced. He positioned himself to the side of her, weighing the flexible
club threateningly and ogling her backside. The headmaster had to admit to himself that apart from her sagging breasts and her wobbly belly that the woman was actually possessed a neat naked form. Her buttocks were tight and firm enough, her waist and narrow hips a delight to see and the large labia peeping out between the tops of her thighs made his cock jerk in urgent need for her.

  The dull thud echoed around the silent room as he swung in with the rolled pillowcase to land a brutal lash on her backside.

  The woman squealed and cried out, her whole body jolted under the impact and her buttocks tensed as the burning pain seeped deeply down through her body.

  "Oh Christ that hurt, no more please," she said between gulped breaths as she coped with the agonising pain.

  "Silence slut," the headmaster hissed venomously and then struck again.

  Again and again he whipped her, aiming the blows so that the tailing end of the knotted pillowcase flicked around to sting at the side of her outer thigh. The bitch would take it; she would endure the pain, suffering and humiliation simply to receive his cock up her. He lashed at her harder for it, turning her backside into a mass of red blotchiness with deeper red contusions to mar the otherwise pale flesh. At length he paused, panting hard in his excitement and steadying his rising climax so as to prolong the pleasure.

  "Lay on your back on the tablecloth stack," he instructed.

  The woman straightened cautiously, tentatively touching at her sore backside but moving over the to waist high pile of white tablecloths. With some difficulty in her discomfort she mounted the wide stack, turned onto her back and lay back.

  "Spread you legs then slut," the headmaster snapped in irritation.

  The teacher did as she was bid, drawing up her knees and parting them wide to offer her gaping sex to the man. She rested her head back, closed her eyes and prepared to accept the long-awaited hot cock up inside her.

  He lashed down with the knotted pillowcase in an overhead swipe of tremendous force, lashing it down to strike hard on the jutting bud of her erect clitoris and her enflamed pussy lips.