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Previous chapters:
One
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Going without a bra at school was difficult for Caitlyn. The standard white school shirts weren’t fully opaque, and without a bra, it was easy to see the full shape of her tits and the dark circles of her areolae through the fabric.
She felt like a whore from the moment she got to school. Everyone could see what a slut she was. There were giggles and outraged gasps as she walked through the school corridors. All eyes were on her slutty outfit. She wanted to run and hide in the toilets, but she hadn’t even brought a bra with her – there was nothing she could do now.
In the very first class she attended, her teacher – Mrs Eldham – sent her straight to the principal. “I can’t believe you think you can act like a whore in my class,” she sputtered.
The principal – Mr Welks – was initially torn between simply forcing Caitlyn to wear a bra, or expelling her, but Caitlyn, desperate and embarrassed, put some of what she had learned with Mr Jones to work.
“Please, sir,” she said. “Are my tits really that ugly?” And, blushing, she unbuttoned her shirt, and let the principal see them clearly.
“No,” he admitted.
“I really can’t wear a bra, sir,” she said. “Isn’t there an agreement we could come to?”
It turned out there was. He brought her over his lap, ass up, as he sat in his chair, and gave her a spanking. When he lifted her skirt and found she wasn’t wearing panties, he called her a slut and a whore, and she knew it was true. When he slid a finger between her exposed pussy lips and up into her fucktunnel, he let him do it, because she knew she deserved it, even though it was the first time she had ever had part of another person inside her pussy.
And when he spanked her… it was good. He beat her exposed buttocks with his bare hand, and on each spank she could feel his erect cock pressing into her groin through his trousers, but rather than hurting, it made a pleasant warmth spread through her ass cheeks. Each thud of his hand sent vibrations through her pussy – which was already wet, long before she walked into his office – and by the time he stopped disciplining her, nearly fifty strokes later, she was quite deliriously aroused.
She didn’t even need to be told what to do next. She remembered from Mr Jones. She was on her knees between his legs. She managed to position herself so that the toe of one of his boots was pressing against her naked, wet pussy. Then she extracted the principal’s cock from his pants, and began sucking.
When she had sucked Mr Jones’ cock, he had already ejaculated, but the principal was still horny. He tasted good, honestly – warm and salty. It felt good to have a cock in her mouth – secure and right, like her pacifier had felt when she was a child. She humped her pussy against the principal’s shoe, and bobbed her head on his dick, and when he finally groaned and she felt sperm shooting into her mouth, she orgasmed right along with him.
Afterwards he told her she was a “good girl”, and he sounded so genuinely satisfied and happy that it produced a warm glow within her own brain. She realised this was the first time all year that any teacher had offered her genuine praise for *anything*, and it felt wonderful.
She left the principal’s office that morning with a stomach full of his cum; a happy, wet pussy; and a note from the principal giving her special permission to dress without a bra, due to her “medical condition”. No one but her and the principal needed to know that the condition in question was “being a whore”.
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On Wednesday, when Caitlyn arrived at Mr Jones’ office, he didn’t even have to say anything. He just looked at her, and Caitlyn blushed, and stripped off her shirt, doing her best to be sexy, to arouse him with her body and her tits.
When she was done, he gave her a device, and said, “Put this inside you.” Caitlyn recognised it immediately – it was an internal vibrator. Her mother had one, although Caitlyn wasn’t supposed to know that.
“Do I really have to?” she asked plaintively. She recognised that she was sliding further down a path to whorishness. Her plan for the year had never involved giving her principal a blowjob, or stripping in front of her guidance counsellor, or inserting a vibrator into her pussy in front of an older man. She felt control – and her sense of identity as a “nice girl” – slipping away from her.
“You need to get comfortable with sexual arousal being your natural state, Caitlyn,” said Mr Jones.
Caitlyn bit her lip. It seemed like arousal already *was* her natural state. She had been wet all week. The way her pussy seemed to wetten eagerly whenever she was humiliated or submissive had been a significant source of shame for her.
But she did as she was told. She reached under her skirt, and slipped the thick purple vibrator into her cunt. She was already well-lubricated, and it slid inside her easily.
“Now turn it on,” said Mr Jones, and Caitlyn did. Her lips parted and she made a little moan as she felt it start to buzz inside her.
And then they did more tutoring work. This week it was science – but Caitlyn found it hard to concentrate with the vibrator humming in her fuckhole. Her exposed nipples were distractingly stiff, and as Mr Jones sat beside her, she was painfully aware of his presence, his warmth, his maleness. She remembered the taste of his cum – of the principal’s cum. She pressed her side up against him, leaned towards him when he spoke, and when he turned his head towards her to correct her on a trivial point, she couldn’t help herself – she kissed him on the lips.
He kissed her back – but when the kiss was over, he pushed her away, hard, with a hand on her tits.
“Don’t be a slut, Caitlyn,” he growled. “I’m trying to *help* you here.”
She was sprawled on the floor, legs spread, pussy showing, vibrator still humming inside it. She was confused, hurt. “I’m sorry,” she said automatically, reflexively.
“This is why I’m saying you’re destined to be a stripper or a whore, Caitlyn,” said Mr Jones. “Because you can’t control yourself even when someone is trying to assist you. You think with your cunt, and that’s been clear to every teacher in this school since the first day you enrolled.”
“I’m sorry!” said Caitlyn again, close to tears.
“Get over here,” said Mr Jones, gesturing at the desk. Caitlyn stood, but when she neared the desk, Mr Jones grabbed her left breast, and yanked down on it sharply. Caitlyn squealed, and fell to her knees. The desk was just about at the height of her tits, in this position, and Mr Jones arranged her breasts so that they were resting on the surface of the desk.
“Hands behind your back,” said Mr Jones, and Caitlyn complied, instinctively, automatically.
Then Mr Jones picked up a long, heavy wooden ruler from his desk – and brought it down across her breasts.
SMACK!
Caitlyn squealed, and pulled back, but Mr Jones grabbed her hair and moved her back into position.
“Nine more, Caitlyn,” said Mr Jones. “For being a slut. Or else you can go home and fail the rest of your classes and enjoy your future as a homeless skank.”
Caitlyn whimpered. Her tits hurt. The ruler was painful. But she was a good girl at heart, and she stayed put as Mr Jones whacked her titflesh with the ruler again.
SMACK!
The pain was awful – but, just like when the principal had spanked her, it was somehow good too. This hurt a lot more than a bare-handed spanking – in fact, it was agonising – but it felt *right*. Each whack made her pussy – still stuffed with the vibrator – pulse in a very interesting way. And with each whack she felt her brain turn off a little, in a way that also felt nice.
All her life at school she had struggled to achieve academic goals that she had never been smart enough to complete, and when she failed she had been full of guilt and self-hatred and shame. But here there were rules – even if she didn’t understand them – and consequences. She had been a slut, so she had her tits punished, and then it was done. Mr Jones knew what she deserved. Mr Jones knew what she needed. She just needed to kneel and let him abuse her tits like a good girl, and everything would be all right.
SMACK! SMACK!
Ten vicious blows landed on her breasts in all. By the end she was crying a little – but they were good tears. Tears of catharsis. The tears that came with knowing that a problem had been resolved.
“Thank you, sir,” she heard herself say.
“Sluts don’t show affection by kissing men on the lips, Caitlyn,” said Mr Jones. “How do you think they show affection?”
Caitlyn knew. She reached forward and unzipped Mr Jones’ pants, and he allowed her to do so. Then she extracted his cock – pleasantly hard, and took it into her mouth.
“Good girl, Caitlyn,” said Mr Jones, stroking her hair as she sucked his cock. “When you’re done pleasing me, you can use the vibrator to masturbate while you watch your educational porn videos. And then we’ll talk about how you’re going to practice masturbating in your regular school classes…”
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