Caned and Humiliated!

Caned & Humiliated!

A word to all, even though this is set in a school all the characters in this story are at least 18 years of age, this includes all the students portrayed. These students are seniors in the school and all are at least 18 years old.

Part Two: The headmaster!

Ellesmere Hall was a private school known for its harsh discipline, the atmosphere has always been strict and intimidating. The school's gothic buildings add to its fearsome presence. Inside, students wear stiff uniforms and are required to move quietly through dark hallways, avoiding eye contact with stern teachers. The curriculum is tough and corporal punishment is common; the sound of a cane striking across the bare buttocks of one of the many students is a daily occurrence. Even small rule breaks result in severe punishment, creating a climate of fear and obedience. Silence is mandatory, and any hint of rebellion is quickly crushed. The staff, strict and unbending, enforce the school's tough standards, believing it builds character and respect. However, beneath the surface, students often feel subdued and long for freedom. The prefects are even worse than the teachers, they use their power to bully all the other students, and of course no one is allowed to 'tell-tale'. If a student was to report another student, it is more likely the student who reports the misbehaviour is likely to get the more serious punishment.

The headmaster of Ellesmere Hall, Edmund Blackwood, was an imposing figure, characterized by his tall, stern presence. Clad in a formal, dark suit, complete with a waistcoat and high collar, he exuded authority and discipline. His piercing eyes could silence a room with a single glance. His posture was always upright, conveying a sense of unwavering control and expectation. Known for his strict adherence to rules and rigorous academic standards, he commanded respect and, at times, fear among his pupils.

Mr. Blackwood walked into the punishment room, "What a glorious sight," He thought, "two perfect naked round asses up in the air ready for their punishment" He gazed admiring the gorgeous asses, both close to perfection, both pale and ready for their caning.

The two young 18-year-olds both naked, asses up and vulnerable to the head, but both equally aroused by the whole situation.

"Well children, I have heard the two of you were caught in a very lewd and inappropriate compromising position. Young Rupert you had your hand up this young lady's underwear and you Henrietta seemed to be enjoying the nasty advances of this badly behaved boy. Therefore, you are both due equal punishments. Here at Ellesmere Hall, we treat both sexes equally and so you will both bear the same punishment." Edmund enjoyed his play on words and smiled to himself. He walked over to the two young people and ran his hands over Henrietta's bare ass and slid his fingers up her hot wet little pussy, "Enjoying this are we? Are you a budding slut, my dear, do I need to beat that out of you?"

"No Sir, please sir, I'm not a slut, you won't catch me behaving so lewdly in school again," the poor girl begged in fear although she knew it was going to be difficult resisting someone touching her hot wet pussy as the head just had, but she wanted to keep her punishment to the minimum.

"Good, I did want to leave some skin on your lovely round ass," The head nodded to himself and walked over to the boy, where he also ran his hand over the boy's delightful firm round buttocks, "Such a feminine ass," He thought, especially with so little hair. The boy whimpered, but in a sad pathetic way.

"Is your little dick hard, boy, why are you aroused, do you like having your bare ass up in the air as if ready to be filled by a thick rod," the head demanded.

"NO SIR!," the boy shouted in fear.

"Do you protest too much?" asked the head as he gave the boy's little nuts a gentle squeeze.

The boy whimpered again, "No Sir, please, I like Henrietta, and please sir, may I take her punishment, and you let her go back to her room."

"Tut-tut, boy, very admirable, maybe you shall take some of her punishment," the head replied running his hand once more over the boy's very round cheeks and sliding his big finger down the boy's ass crack and over his puckered little anus.

"Oooh," the boy responded to the touch, "please sir, I will take her punishment," and Rupert begged earnestly. He really didn't want Henrietta to see him snivelling when he was beaten, he knew already that he would struggle with the pain. He was a very sensitive boy, his mother always said so.

The head gave the boy's ass another hard slap and stepped away to the cupboard where he kept his rattan canes. The boy squealed at the slap. "What a sissy," the headmaster thought. He took out his favourite vicious looking rod of rattan and as he walked back to admire the two youngsters, he 'swooshed' it through the air a couple of times and got two gasps of shock from the two waiting victims.

The headmaster stood back a little behind the two prepared bare asses and admired their gorgeous round cheeks. As he quietly watched knowing this anticipation will only make their ordeal far worse, he quietly unbuttoned his trouser and took out his thick hard cock. The two youngsters were not in any position to see the headmaster's bared big thick rod, he always administered punishment in this was as it always aroused him, both the sight of a firm round bottom so lewdly displayed with the holes fully on show, and his enjoyment of administering the vicious sharp strokes of the cane.

Now, who to choose first. He felt the boy was the weaker and it would create more fear for the girl when she heard her 'friend' cry out. He stood to the left of the boy and laid the cane across the centre of the boy's buttocks. The boy clenched his teeth, he did not want to cry out and he didn't want to sob in earshot of Henrietta but had no idea how much this was going to hurt, he just knew it was going to be bad.

"Whoosh," "Aghhhhhhhh!," the poor boy wailed. The cane struck right across the centre of the boy's gorgeous round ass at the peak of its roundness leaving a vicious red welt all the way across. The boy couldn't help himself his teeth started to chatter, and he sobbed.

"Whoosh," "Aghhhhhhhh!," the next an inch above the first.

"Whoosh," "Aghhhhhhhh!," and another inch higher. Now three very red nasty welts across the upper part of the boy's firm round ass cheeks.

The headmaster moved to the left of the young lady and laid the cane across the centre of her luscious round ass cheeks, so pale and perfect in every way her bottom was near enough perfect he will enjoy laying his marks on this ass.

"Whoosh," "Aghh!," the poor girl cried out. As with the boy before the cane struck right across the centre of her gorgeous round ass cheeks right at the peak of its roundness leaving a vicious red welt all the way across.

The headmaster repeated the process on the girl's bottom getting a louder shriek on each strike and now she had the three vicious red welts across her beautiful round ass cheeks.

The headmaster moved back to the boy who was now shaking in pain and fear, and sobbing pitifully. The head looked greedily at the wobbling round ass admiring how gorgeous and round it looked and how beautifully it wobbled with the boy's sobs and of course he admired the three vicious red welts. He laid the cane across the base of the boy's round ass, at the crease with the boy's slender thighs, where the ass was at it softest and the head knew, this was going to hurt the quivering boy even more.

"Whoosh," "Aghhhhhhhh!," the poor boy wailed again and the sobs increased.

"Whoosh," "Aghhhhhhhh!," this time the wail seemed particularly high pitched, almost that to f a girl, as before the next an inch above the previous.

"Whoosh," "Aghhhhhhhh!," and another inch higher. Now three more very red nasty welts across the lower part of the boy's firm round ass cheeks.

The headmaster reluctantly moved away from the boy as he was enjoying how much pain the boy was in and was enjoying seeing the boy's feminine round ass cheeks wobbling and the puckered little rear hole winking at him, as if it was beckoning the head for more attention. He took his position beside the girl and firstly admired how beautiful and sexy her luscious round ass cheeks looked, then he repeated the process as he had with the boy. The first strike along the girl's crease got the desired response and she wailed for the first time. The head knew that this part of the ass, especially on a girl, was usually extra soft and tender, the red welt lining across the crease looked particularly nasty on Henrietta. And she sobbed for the first time. Then the two more strikes each an inch higher.

Now the headmaster was able to stand back and admire his handiwork with some pride. These two students were both very beautiful. Two very attractive young students, both 18-years old and both naked, tied over the punishment horses a pair of very beautiful backsides, both of them striped with six red welts where they had received the necessary six-of-the-best. Both bottoms were quite gorgeous in their own way. The girl had a very round, heart-shaped ass with full cheeks and flared hips from her very slim waist. The boy's bottom was surprisingly feminine, obviously slimmer than the naughty young lady's but still round, nicely full and firm buttocks, giving the boy a feminine curve from his slim waist.

The headmaster was now pondering his choice, he could, as he would normally do, and he was sure the young lady, currently bent over the horse with her holes easily available, expected him to pick one and satisfy his lust after having caned the pair. But his eye was drawn to the young man, barely more than a boy. The headmaster looked upon how shapely the young man's round buttocks actually were, almost feminine, and the boy being blonde and pale, had surprisingly little body hair making him from this angle look quite girly. The kinkiness of the idea was making it almost irresistible for the headmaster.

The headmaster stood behind the boy and ran his hands over the boy's firm round, viciously striped buttocks, thinking how much he had enjoyed caning this nice ass. He placed a large hand on each ass cheek and gently pulled them apart to expose the boy's puckered little hole. There was so little hair down the boy's ass crack and the hairs blonde and light were nearly invisible; "This could be a girl's backside" thought the headmaster, "and I'm sure the poor boy hadn't expected this part of his punishment."

The boy was feeling so very uncomfortable, yes, he expected the severe punishment for being caught with his hand up a girl's dress and knew it would mean the cane but now the head was groping his ass the way he might a girl. "I'm not a girl," he wanted to shout. Yes, several of the other boys had made passes at him, he had very fine features and twice two different boys had tried to kiss him in the dorms. But he wasn't interested in boys, he was totally into girls and ONLY girls. He heard the head hack up some phlegm into his mouth and then felt the spit hit right on his little rear hole. "NOOOO!" He shouted in his head but knew he must remain quiet if he wanted to get out of here without having his ass flogged to the bone. He'd seen Jones's backside after the boy had argued with the headmaster about why he should be caned. There were welts on welts and the poor boy couldn't sit down for more than a week.

"Ouch," the boy called out as the head pressed a finger into the little hole.

"Quiet boy," the head wriggled his finger around to get the boy's little hole to open more, then it was two fingers. The boy bit down, teeth clenched, knowing he must remain silent. But this wasn't right, and it was wrong as he felt the head push the two thick digits into his little tight rear passage.

Then the fingers were gone, and his hole was empty. But not for long, then he felt something much thicker pressed up against his precious little hole that no one had ever touched before. "NOOOOOO!" again he wanted to scream but clenched his teeth for fear of angering the man.

To his left Henrietta could hear the different sounds and the sobbing of Rupert and wasn't sure what was happening, she tried to angle her head to see but from her position, bent over as she was all she could see was the boy's legs tied to the horse and she could see the shoes and trousers of the head's leg right behind the boy. She had heard rumours from other students that the head satisfied himself by using one of the girl's holes after the caning, but hadn't really believed them, and now she was growing suspicious that the head was about to use Ruperts tight rear little hole.

The head looked down upon his thick cock pressed against the boy's pretty little puckered star, he pushed, "Relax boy, relax, it'll hurt less," and he pushed forward, and a deep moan of pain escaped the boy's lips. This did not deter the headmaster, and he pushed forward till he had about 3 thick inches in the boy, then pulled back till the tight little sphincter gripped the head of his cock. He loved the feeling of a tight sphincter fighting against the intrusion, especially the first time, it would pulse and clench around his big purple bellend trying to repulse the intruder but would end up just stimulating the man gaining entrance. It didn't help that each time the man pushed in against the boy's arse, this squashed the boy down hard onto his trapped little balls against the wood of the horse.

The head pushed forward getting maybe 4 inches in, pulled back and felt that pulsing sphincter, pushed deeper, pulled back, pushed forward, he had 6 inches in now. He heard the boy whimper, and he reached round and grasped the boy's hard slender dick. "You're loving this boy; your little dick is rock hard." As he kept up the slow in-out movement slowly getting deeper, he gently stroked the boy's slender dick.

This made the whole humiliation 10 times worse for the poor boy. He was hard and erect while being fucked by the headmaster up his virgin little arse hole. A man fucking him in his tight little virgin rear hole, and he was hard and dripping pre-cum; "I'm gay!" was flashing in his head, and he started to sob.

'OMG!" Henrietta had heard the exchange and now she knew not only was the head penetrating her crush but the boy she totally fancied, was enjoying being taken up his arse by the headmaster! To be honest Henrietta found it all very hot, the sex noises, even though she was quite jealous of Rupert and was thinking, "Fuck I need one of my hole to be used."

The headmaster was picking up the pace now, he still had his hand wrapped firmly around the boy's slim dick, but he was just holding it now and no longer stroking, as his full concentration was on penetrating the boy's delightfully tight little rear passage and getting his thick cock as deep as he could. He now had very nearly all eight and half thick inches in, and the poor boy could feel the slap of the bigger man's large balls striking his squashed little nuts on every other thrust. The poor boy was letting out a pained squeal each time his balls got slapped, which made him sound even more feminine and bolstered the headmaster's desire to up the pace and get the last inch of his big cock fully wedged in the boy's tight little anal chute. He drove home with another powerful thrust and hit balls deep, his big balls slapping hard against the poor boys little squashed nuts.

"Arhhhhhhh!" the boy let out a long squeal and feeling his tight little rear passage painfully stretched out and stuffed so amazingly full, with the hard slap onto his little nuts, he cried out again and to his utter humiliation, his slim little dick shot one spurt of young watery sperm out across the floor after another. To his greater shame out of the corner of his eye he could see Henrietta watching his humiliation and his little dick spurting its thick cummies as he got the deep arse fucking.

For Henrietta, she was not only thinking that this beautiful young man was enjoying being fucked by the headmaster up his tight little bum hole, but she was also a little jealous. She had expected to be the one to be fucked, either in her arse or her little pussy. She had heard from other girls that this was usually part of the caning ritual by the headmaster if you were pretty. She was a little put out that the headmaster had chosen Rupert, thinking that he must find the boy more attractive than her, but was glad she could keep her virginities for at least a while longer. She had hoped Rupert would be the one to take her virginity, but now she had seen his rather unsatisfying looking little dicklet she was not so sure. "They could be good friends," she thought," and maybe I will let Rupert's roguish friend Roger take me, he was always chasing the girls and the ones to have claimed to have seen it said he had a big dick.

What Henrietta did find strange, her little pussy was throbbing at the sounds of sex next to her, and this made her jealous as her pussy could do with a hard pounding right now and the pretty Rupert was getting the fucking she wanted.

When Rupert came, shooting his thin watery spunk across the room his tight little anal chute automatically spasmed against the thick rod penetrating him. This was all it now needed for the head to unload his thick spunk deep into the boy's bowels. Rupert felt the thick cock swell and then he could feel the heat and the wetness as his bowels were filled with thick fertile spunk.

Having shot his load, the head stood leaning against the boy's round feminine bottom allowing his cock to soften before he pulled out and he held the boy's round ass cheeks to keep the little hole gaping and watched some of his thick spunk dribble out down on to the boy's squashed little nuts. The head stood for a moment to admire his handiwork, then wiped his still dripping cock across the boy's round ass cheeks.

The headmaster stepped back looked across rather disappointedly at the beautiful young Henrietta, ass up, and looked hungrily at her holes but knew he couldn't be too greedy. He put his thick cock back into his trousers, went out to the corridor where the prefects were waiting, "Don't be too mean to them, a little bit of fun but don't go too far."

Continued in Chapter 3