Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Reluctant, Coercion, Blackmail, Heterosexual, Spanking, Humiliation, Oral Sex, Masturbation, Big Breasts, School, .
Desc: BDSM Sex Story: Chapter 1 - Headgirl is spanked and humiliated (With Apologies to Geoffrey Chaucer)
I am one of less than twenty boys in my school. If that sounds unusual, allow me to explain. I attend Saint Erentrude's, an exclusive, old fashioned and very strict all-girls boarding school. Well 'all-girls' isn't quite true. You see, teachers sons are allowed to attend and there are usually about two or three in each year at the school. They are given no special treatment and their presence does lead to some embarrassment for both boys and girls, given the punishment regime of the school.
Saint Erentrude's employs a regime of corporal punishment. Rule breakers are punished with hand-spankings, the slipper or, for the more serious offences, the cane. The school even reserves the birch as a last resort, only to be used in situations where any other school would use expulsion.
The school has a prefect system, whereby trusted sixth-form pupils are appointed to help the teachers. Their responsibilities include punishing pupils for misdemeanours (naturally, these punishments are corporal in nature). When boys deserve, in the sixth form, to be made prefects, they are - and they are trusted not to abuse their right to remove girls' knickers.
I was never very popular at school. The other lads shunned me and the girls pretended I didn't exist, I was better at English and Maths and Science than at football I was also overweight and had worn glasses and braces until last year when I had finally been able to ditch the braces (at the same time I had swapped my glasses for contacts). This made me a 'freak' as well as a 'swot'; and I was either picked on or ignored by the popular crowd of boys and girls. However I had always taken care to be popular amongst the teachers. Even in French, my worst subject, I had always taken care to try my best.
As a result, when I joined the sixth-form this year at the ripe age of eighteen, I received that rarest of honours. I was one of only three male prefects in the entire school. Nobody dared to pick on me now that I had the power to spank pupils or send them to their housemaster for the cane. Even the other newly made prefects restricted themselves to the odd snide comment.
It was two weeks into term when my first chance for revenge came. The Headmaster was having one of my periodic crackdowns on smokers and had asked all the prefects to keep an eye out on the usual spots (actually with the school's strict rules the usual spots changed on a weekly if not daily basis). So it was that I took twenty minutes of my lunch hour to wander round some secluded areas. I was about to give up when I heard a snatch of conversation from two fourth form girls.
" ... Just been for a tab round the back of the language lab. Prefects haven't clocked that one yet." I smiled and wandered off in that direction.
As I rounded the corner I caught a whiff of smoke and saw a group of three fifth year girls puffing on silk cuts. Behind them were three familiar figures; Richard, Matthew and Dave were the leaders of the
'popular crowd' in my year and my chief tormentors; this was going to be sweet! They were grouped in a small huddle, however I could see only one cigarette, I sniffed again and smiled in triumph, that wasn't tobacco!
I cleared my throat loudly and the six students froze. I marched over to Richard and snatched the joint from my hand before he could recover. I stubbed it out on the wall and palmed it. Then I turned to the three girls.
"Put those out," I snapped. "All of you come with me."
I led them all into the school building and into an empty classroom.
"You three wait here," I said to the girls. "Come on!" I snapped at the others and led them on down the corridor to the Headmaster's study. I knocked and waited.
"Come," Mr Critchley ordered. I opened the door and ushered the three miscreants in and then stepped in after them, closing the door behind us. I succinctly explained how I had found them just a few minutes ago. I handed the half smoked spliff to the Head and he sniffed it and frowned more deeply. "Thank you," he said to me.
"My pleasure," I replied evenly, "just doing my job. If you'll excuse me Sir I have some cigarette smokers I'm going to deal with myself."
"Of course," the Headmaster replied. "You were right to bring this to me"
I returned to deal with the naughty girls with a renewed spring in my step. I love being a prefect.
Richard, Dave and Matthew's fate was announced in assembly the next day. Richard had been identified as the instigator - a baggie was found in my pocket and he admitted to being the one who got it for the others. So while Dave and Matthew would each receive twelve of the best at a Whole School Public, Richard would be getting the birch. It was the best news I'd heard in ages. Whole School Publics were almost unheard of. House Publics were rare enough, one a year, if that. Only the teachers could remember the last WSP.
Sophie Rudkin, a persistent offender, had received ten strokes of the cane naked before the whole school when first one, then two and then eventually all twelve of her first year victims had plucked up the courage to tell the head about her systematic bullying campaign.
Meanwhile Richard would be the first boy to receive the birch in Saint Erentrude's history. Almost everyone in the hall could remember the screams from the last girl to receive the birch. Ellen Sykes had been caught trying to steal an exam paper and had received the school's ultimate sanction.
The Whole School Public was part of Thursday morning's assembly. The Headmaster led the two naked boys onto the stage, the girls hardly bothering to hide their sniggers and comments. Mr Critchley delivered as fierce a caning as anyone present had ever witnessed and then left the boys naked, facing the school while he finished assembly.
At Friday at 9.00 the whole school stopped for the birching. I was in a free classroom with the three fifth year girls I had caught smoking. I had decided their discipline should coincide with the birching and so Kelly Sheridan a very attractive schoolgirl lay across my lap, her pleated school skirt was raised above her waist and I had lowered her knickers below her knees.
Her two friends, Liz Allen and Sarah Short stood facing me hands on heads, waiting their turn. Kelly's spanking would continue once she had finished listening to Richard's screams which could be heard even from here. He finally fell silent and I paused to let it sink in before I spoke to the three girls.
"Remember that is what can happen to trouble makers and count yourselves lucky you escaped with a hand spanking this time. Kelly you've got ten more to come count them out please."
The effect on my fellow students was immediately noticeable. People who wouldn't give me the time of day before now went out of their way to be civil to me. The only person who dared to be rude to me now was the Head Girl, Alison Jackson. She hadn't been spanked since she was a third year and had never had the cane.
As Head Girl she considered herself above such concerns (and above most of us mere mortals). She was very popular with all the teachers (even more so than me) and with the pupils, she was the best looking girl in school and she knew it! She had an acid tongue when teachers were out of earshot which endeared her with the in crowd of sneeringly superior 'beautiful people.'
Unfortunately I doubted I would ever get revenge on the ice queen and so I did my best to ignore her and did so perfect a job as Prefect that she would never be able to reprimand me in her position as Head Girl and First Prefect.
However my chance did come, I was making my way to class when Alison came dashing the other way, running late for French class on the other side of campus and anxious not to upset the notoriously strict Mr. Killian.
She careered into me and hissed a particularly vile insult at me as she picked herself up and went to grab her bag. That's when she froze, I followed her gaze and saw why, a bottle of vodka wrapped in a spare jumper had rolled out of her bag, she snatched it into her bag but she was too late. I took her bag from her and said,
"I think we'd better have a word." I led her into an empty classroom and shut the door. "Well, well, well," I said slowly, "our very own Head Girl with booze in school." To her credit Alison had completely recovered by now and resumed her usual sneer.
"Listen shit," she snapped, "I'll just tell the Headmaster it was me that found it on you and now you've concocted a ridiculous story to try and get yourself out of it. I think we both know who'll be believed. Now unless you want the cane I suggest you give me my vodka back."
"I believe we both enjoy Mr. Critchley's trust," I replied. "I just need some hard evidence." I picked up her bag again and began rummaging through it, ignoring Alison's protests.
In the front pocket was a scrunched up Victoria Wine bag. I opened it up and rummaged inside. I pulled out a crumpled receipt, on closer examination it was a credit card slip
"Dr. Phillip Jackson, that's your father isn't it. You're a signatory on my card aren't you?" I knew the answer to this, Alison was always flashing the Gold Card about and boasting about her rich background. "Smirnoff Blue, fifteen pounds I continued."
At last Alison cracked and began to plead. She was used to getting what she wanted and clearly thought she could get round me.
"Please," she started, even using my name (normally she referred to me as 'shit' or 'geek'.
"Let me off, I'll let you come to the party and I'll make sure everyone's nice to you, there'll be lots of girls there and..."
"I'm not interested in partying with people who're only even being civil with me to keep you out of trouble," I told her.
"I'll be nice to you for the rest of the year she continued. I'll make sure everyone lays off you. Please"
"I think you'll be nicer to me anyway once you're no longer Head Girl and I'm still a Prefect," I said smugly. "No, I'll think I'll give you a spanking and then send you to the Head for the cane. Maybe it'll be another Whole School Public I teased."
Alison went pale. She had never had the cane and the mere thought terrified her. As for a Whole School Public, the humiliation would be too much to bear. Then her parents would punish her for losing her rank as Head Girl (Daddy would probably cut off her allowance) and she would lose her much loved authority.
"Please," she tried again "couldn't you punish me yourself, you know you could give me the slipper or something,"
I simply smiled and shook my head.
"Or, or I could you know give you a ... a blowjob" Ali finally said clearly desperate.
"Very well," I said. "So, in addition to your spanking you're going to get the slipper and then you're going to receive some additional, intimate punishment from me.
"In return you may keep your vodka and no one else need ever know. Very well but you will do exactly what I say. Understood?"
Ali looked horrified she'd been prepared to suck me off to escape the cane but to take a spanking and a slippering as well ... However she had little choice.
"Yes" she said quietly "Yes what?" I prompted. "Yes Sir," she said blushing
"Very well, come here." I ordered. She came and stood in front of me. "Take everything off above the waist," I ordered.
Reluctantly, Alison moved to comply, she undid her tie, folded it and placed it on the desk. Then she untucked her blouse and slowly began to unbutton it.
The few male students at Saint Erentrude's all agreed that Alison had the biggest and best tits in the school and as she took off her blouse, folded it, put it on the desk and stood before me in just a black lacy push up bra I was even more impressed.
"And the bra," I prompted she reached behind herself pushing her jugs out even further and unclasped it. Then she pulled the garment off her chest altogether and placed it on the desk with her shirt and tie.
"Put your hands on your head." I told her as she tried to cover herself. Blushing harder than ever, Alison raised her hands onto her head displaying her charms lewdly to me.
"Now, ask me to play with your tits," I ordered. Alison looked ready to storm out but she didn't.
Instead she muttered, "Please play with my tits, Sir."
"I'm sorry I didn't hear that," I said innocently, "and look at me when you speak to me.
"Please play with my big tits, Sir," Alison repeated loud and clear, looking me in the face this time (though she was bright red with the humiliation of it).
Who was I to refuse a lady?! I reached out and cupped the breasts I had fantasised about and began to squeeze them and rub them and play with them. After about ten minutes of this I released them
"Now what do you say?" I prompted.
"Thank you for playing with my tits sir," Alison replied obediently.
"Now put yourself over my knee, I ordered. I'm going to give you a good spanking before you get the slipper. You obviously need to learn how a Head Girl should behave." So saying, I seated myself on the chair and motioned for her to approach me.
Shamefaced and taking tiny, reluctant steps in her smart high-heeled pumps, Alison advanced toward me. Despite her eighteen years and mature, shapely figure, her demeanour suggested that of a very young girl about to receive a deserved spanking.
Taking her by the hand, I gently but firmly pulled her face down across my lap. Nearly falling into position, Alison lay with her palms on the floor to balance herself. Her school skirt rode up to reveal a generous amount of black stocking, and her knees were slightly bent. Knowing what was coming, she was scarlet with embarrassment.
I reached down with both hands and, with great slowness, began raising the hem of her pleated black school skirt. Lush, tapering thighs, enhanced by black stockings, came into view,
followed by the heavier portions of her stockings. Then came milk white thighs, contrasting vividly with her black stockings.
The school skirt came up to the waist, slowly bringing into view form fitting black knickers that could barely contain her lovely and fully rounded buttocks. With her stocking tops, bare thighs and black panties on full display, Alison was a picture of feminine embarrassment. Her face was a flaming scarlet and she kept her eyes tightly closed, as if that would block out the shameful display she was making of herself.
I paused for a moment to enjoy the breathtaking view, not missing a single detail as my eyes moved from the tips of her nicely shod feet to her head. Both of us were aware of the erection that the display had already produced.
Alison moaned and wriggled with girlish apprehension as I clasped my left forearm and
hand around her waist to hold her in position.
"OK Alison, I'm going to start by spanking you over your knickers to 'warm you up' but then they'll have to come down. We'll start with ten over the knickers — you will count them out." I ordered her.
So saying I raised my hand and brought it down lightly upon her right buttock,
leaving it in place right where it landed. Her youthful bottom felt velvety soft and resilient through her skimpy underwear. Alison groaned
"Oooh!" her gasp reflecting mortification as much as discomfort.
"One, Sir. Thank you Sir" she counted. I raised my hand again and brought it down a little more forcefully, on her left buttock this time
"Two, Sir. Thank you Sir" moaned Alison.
I took a moment to rub and squeeze her delectable arse — I had no intention of rushing her punishment, intent as I was on savouring every second...
"Ten, Sir. Thank you Sir" Alison's voice wavered, the discomfort and humiliation of her spanking had the formerly haughty head girl on the verge of tears.
After a long pause, I reached for the waistband of the young girl's wispy panties. Alison moaned and quivered with humiliation as she felt my hands committing the final indignity that would leave her totally bare and disgraced.
"Lift up a little, Alison," I ordered her. Haplessly, the attractive pupil lifted her hips an inch or so from my lap, and I slowly pulled the panties down.
Alison's breath-catching feminine bottom flashed into view, a beautifully soft mixture of pink and white, and deliciously rounded. The feminine contours were girlishly big but not too big. Alison trembled with humiliation and as she did so, her pretty nates quivered like bowls of jelly. She remembered to hold her stockinged legs tightly together, for the moment at least, concealing her feminine treasure.
I finished pulling the panties down below the tops of her black stockings, and paused to enjoy an enthralled look at the lush and tender feminine buttocks that were just waiting for further discipline.
"You have lovely buttocks, Alison!" I told her, knowing that the comment would embarrass rather than please her.
I had no intention of rushing things. Slowly I raised my right hand and watched the pretty teenager shrivel with embarrassment at the bare-on-bare contact. After a moment's pause, I raised my hand to observe the pretty pink spot that had suddenly appeared.
I applied the second slap to her right cheek, slightly lower down, and once again allowed my hand to remain in place for a moment afterward.
The third smack landed slightly lower than the second. I then repeated the procedure, this time making the smacks slightly more forceful.
"Oh! Oh!" Alison gasped, her pigtails flying. "This is awful! Please, I'm too big for this!"
By this time the attractive pupil was a little breathless and her buttocks were a healthy shade of rose pink and the comely teenager was squirming with a mixture of embarrassment and discomfort.
After pausing a moment to admire my own handiwork, I began the next series of slaps with a light slap just above the top of her right stocking. Alison moaned and her right foot swung up momentarily. I began working up her right thigh and bottom cheek with a light series of smacks, always allowing my hand to remain in place on the cringing feminine flesh beneath my palm.
From there, I worked down the left side to the top of her stocking. I repeated the entire course again, working up, the right side and down the left.
"Please! Please!" Alison pleaded. "Please stop! That's enough! Please don't humiliate me like this! Please, I'm tool old for this, I'm eighteen!"
Once again my palm traversed the course, working up one side and down the other. A distressed "Oh!" followed every smack, and her reddening buttocks began to squirm more and more over my lap despite her obvious efforts to control herself.
Black patent leather pumps began swinging upward from time to time, and I knew there would soon come a time when she would no longer be able to hold those pretty legs together.
"Ouch! Oh, stop, please! Please!" Alison pleaded, looking back anxiously over her shoulder. "Please, don't! It's too humiliating! Please, your bare hand on my ... my bare ... Please, it's so humiliating!"
"Yes, my dear, I replied cooly, "that's the point"
I paused once again to admire the scenery, Alison's lush spank spot was a bright scarlet. She was wriggling miserably, her full buttocks continually flexing and puckering in a thoroughly provocative manner. Her pretty face was as red as her bottom, and her distress was all too apparent as she continually looked back over her shoulder.
It was time for the bottom smacking to start in earnest. I raised my hand and brought it down forcefully on Alison's buttocks, producing a loud smack as it landed squarely across the crevice.
"Ouch!" Alison shrieked and suddenly burst into girlish tears. Smack! Smack! my hand began moving up one side and down the other, each smack crackling with a crisp report as it landed on defenceless feminine flesh.
"Ouch! Oh, no! Ow! Stop! Ouch! It hurts too much!" Alison exclaimed, her voice reflecting her pain and shame. "Ow! Ouch! Oh, no! This is awful!" Shapely legs prettily attired in black
stockings and high heels began swinging merrily back and forth as I spread the stinging smacks across her already-smarting posterior, and the pretty teenager began wriggling furiously over my lap.
As she reflexively began jerking her legs hard and wide, bright flashes of pink cuntal lips could occasionally be seen along with an intriguing patch of light brown fleece.
"Oh, no! Stop! Ouch! It hurts too much!" Alison begged, her voice nearly choking with tears. "Stop, please! I'm just burning up!"
Keeping her squirming, bucking body under full control, I continued to apply the loud smacks in a lusty, energetic fashion. Shapely long legs in stockings and heels kicked frantically back and forth, and the entire combination of tear-stained face, glowing buttocks and swinging legs was exquisite.
"Oh, please, stop, I can't take it anymore!" the miserable girl sobbed between soprano shrieks of pain. "Stop, please! Pleeeese!"
At last, I decided that my suffering victim had endured enough of that kind of discipline. As she lay crying hard across my lap, I finished removing her black panties and tossed them on
the floor. my hand slipped between her legs, the lips of her warm teenage pussy felt deliciously soft and juicy, and I slipped a probing finger gently into the wet interior. Alison moaned, an intoxicating mixture of arousal and humiliation.
"Fetch me the slipper I ordered and Alison got up and made her way to the small cupboard at the back of the room. There was one like it in every classroom and they all contained the same things, a slipper, a long wooden ruler and a paddle. Alison reached in and picked up the
slipper, a thick soled size twelve.
She brought it over and handed it to me.
"Now back into position" I ordered.
"Yes Sir," Alison replied resignedly as she slid herself over my lap once more, trying to ignore the throb of my erection.
"Now then, let's see I think twenty whacks for the vodka and another ten for trying to get out of punishment. You will count each whack aloud. If you count incorrectly or call out other than to count I will add another five.
"One Sir, thank you Sir" she gasped out as I laid the first whack on her buttock.
When I reached ten I snaked my left hand around to cup her breasts and played with those as I completed her slippering. Alison was so flustered that she lost count twice so she had to take forty in the end and I succeeded in reducing the proud girl to real tears.
As she lay on my lap groaning with pain and humiliation I rubbed her arse slowly then slid my hand between her legs to her cunt. It was wet. I leisurely fingered her for a while, playing with her tits again with my free hand.
"That turned you on didn't it," I teased.
"Yes Sir," the Head Girl admitted breathlessly.
"It's time for the next part of your punishment," I told her. "You know what you have to do, don't you?" I asked quietly.
"Yes. Yes, sir!" Alison managed to reply, trying to get her tears under control.
"Kneel in front of me and take it out yourself!" I instructed.
Wiping the tears from her hotly flushed face; Alison meekly slid into a kneeling position
between my legs. Her pretty face clearly mirrored the distress caused by the spanking, but I could also discern an underlying look of excitement about what was to come.
She was quite breathless and her full young breasts were heaving. Her expressive blue eyes narrowed intently as she focused them on the handsome curve in my trousers.
"Go on," I told her. "Take it out of my pants yourself, and then I'm sure you know what to do!"
Her eyes flashed upward for a moment. Nervously Alison licked her full lips then, very shame-faced, the pretty eighteen-year-old began unzipping my fly. Her small fingers worked slowly but showed no hesitation.
Leaning back casually in my chair, I watched closely. As Alison pulled my open fly apart, my throbbing, bone-hard penis suddenly sprang out into full view. As she caught sight of the solid eight inches of cock, the comely teenager gulped noticeably and involuntarily wriggled with girlish surrender.
"Go on, Alison, you know what you have to do!" I told her quietly.
Alison extended her small right hand and encircled my hotly throbbing member in a possessive grip. Her smooth feminine hand felt exquisitely pleasant, and I caught my breath sharply.
She cupped my balls in her hands and looked up at me. Then she kissed the end of my knob and began working her way down with little kisses and licks until she reached my balls. She sucked each one in turn while wanking the shaft in her soft warm hand. Then she kissed her way back up to the top of my cock.
Licking her lips with her small pink tongue, Alison slowly formed her pretty mouth into a wide oval. Leaning forward, she eased her full lips down over the crown of my massive blood-distended cock.
The full effect of the young girl's hot, wet mouth suddenly hit me like a thunderbolt, and my entire body stiffened as if struck by a jolt of electricity.
"That's the way!" I told her in a deliberately controlled voice.
Alison held the velvety smooth crown of my stiffly erect penis in her mouth and sucked lightly on it, while at the same time her soft fingers played up and down the throbbing trunk of my elongated manhood.
She gradually took about half my cock into her mouth and began sucking whilst teasing the end with her tongue. Her hands returned to my balls. I began playing with her big tits, cupping them in my hands and squeezing them together kneading the heavy mam-meat like play-dough and tweaking her sensitive nipples.
"You're good at this," I commented, "I bet you've sucked a lot of dick haven't you?"
Alison just groaned and carried on giving me a great blowjob. Ali was working hard on my cock, the head fully inside her mouth, touching her cheek as she swirled her tongue around and around.
"Play with your cunt while you do it!" I ordered.
Obediently, Alison slid her right hand under her short skirt and onto her naked pussy. She began to masturbate, moaning around my cock as she worked first one then two fingers into her sopping wet twat.
Her mouth continually filled with saliva and from time to time she was forced to pause and swallow it with an audible gulp. Thoroughly aroused, the shapely teenager continued fingering her wet pussy.
From my position, I could see a feminine finger eagerly exploring between her separated wet cuntal lips. Wriggling her well spanked little bottom, Alison masturbated as she submissively sucked my massive prick.
At this point, I pushed Alison's shoulder back against the desk behind her and pulled my cock out of her mouth. Ali protested, trying to get my dick back in her mouth, but I took her hands away.
Alison's magnificent tits stood out firm, the nipples fully erect, pink and stiff. I let my cock slide down her neck and down her breastbone until it rested between the two mounds of flesh.
I took one of her hands firmly, putting it on the side of her breast, then the other, pulling it away from the spot where it was rubbing her crotch and placing it on her other ripe tit. I slowly pushed her hands together until my cock was buried in the soft pliable tit flesh, the red tip poking up between them.
Ali quickly got the idea and began rubbing my hard prick between her tits, sliding her nipples against my engorged organ with her fingers and murmuring in pleasure. I stood over her a while, enjoying the sensation of smooth tit flesh against his cock. She continued to move her breasts around my dick, ducking her head to lick and suck at the tip as it emerged from between her baps After a few minutes of this I sensed that I was now close.
"OK, sweetheart, I said. "Finish me off with your mouth and make sure you swallow!"
She released my cock from between her big tits and hungrily took it back into her mouth.
Her right hand returned to her wet pussy and her left cupped my balls. I cupped a tit in each hand and played with them as her skilful mouth brought me closer and closer.
I began thrusting forwards, gently fucking her face she moaned and her right hand moved faster underneath her school skirt.
Suddenly, I could hold myself back no longer, Alison looked up at me and I came in her mouth Clamping my hands powerfully around her head, I bolted almost to a standing position. A hot load of thick, sticky fluid smashed against the roof of her mouth, Alison instinctively attempted to snap her head back, but my hands forced her to remain in position.
Another blast of my masculine cream sprayed into her mouth, coating her tongue and trickling down her throat. Alison felt as if a hot fountain of thick cream had been turned on in her mouth.
Hot, sticky masculine lava sprayed forth in voluminous quantities, completely filling her teenage mouth. Gurgling and gulping on the virile, salty fluid, the young and comely schoolgirl began swallowing it with loud gulps. I could see her voluptuous body quaking as she experienced her own orgasm.
As I settled back on my chair, Alison obediently kept my cock in her mouth until it began to go soft. I pulled out and slapped her cheek with my softening prick, leaving cum on her face I did the same on the other cheek. Then I said "Lick it clean, bitch" Alison took my cock back in her mouth and licked and sucked it clean. I put it away and stood up.
"Now what do you say Alison?" I prompted
"Thank you for my punishment Sir," she said obediently.
With that I turned and walked out of the room, leaving the Head Girl kneeling on the floor, well spanked and topless, her knickers round her knees and my cum on her face.