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Caitlyn was failing her final year of school, and yet she was too poor to afford a tutor, so she approached Mr Jones, the school guidance counsellor for help.
“I think you need to be realistic, Caitlyn,” said Mr Jones, as the blushing 18-year-old schoolgirl sat opposite him in his office. “At this rate, you’re not going to graduate, and for a girl like you in this town, that means a career as a stripper or a prostitute.”
Caitlyn burst into tears. “I don’t want to be a stripper!” she wailed. “I don’t even know how!”
“I’ll make you a deal, Caitlyn,” said Mr Jones. “You come here for two hours after school every Wednesday, and I’ll tutor you. We’ll spend an hour trying to improve your grades, and an hour preparing you for the possibility you’ll be a stripper.”
Caitlyn was stupid, but not that stupid. She knew this wasn’t a normal thing for a guidance counsellor to offer – but she had no alternatives. She agreed.
On the first Wednesday, Mr Jones started by telling her to lift her shirt and expose her bra. “You’re going to need to get used to being undressed in front of people, Caitlyn,” he told her, “or you’ll never make it as a stripper.” He stared at her as the embarrassed teen pulled up her shirt and showed him her bra-covered tits. He smiled, and told her she was a good girl, and then went to work for an hour of remedial mathematics.
At the end, he started her hour of “stripper training”. He put a collection of porn clips on a screen, and made Caitlyn watch, and take notes, and at the end asked her for ten reasons why the girls on screen were more desirable than Caitlyn. Caitlyn blushing identified the fact that they were nude, they had big plastic tits, they let men fuck them, their pussies were shaved, they let men slap them, they had sex with other women – and then she ran out of ideas. As punishment, Mr Jones demanded that she remove her panties. Caitlyn went bright red as she reached under her skirt and slid her underwear down her legs. Mr Jones took it from her, made a point of noticing the wet patch in the crotch, and then placed the panties in his desk drawer and closed it.
“Don’t wear panties anymore, Caitlyn,” he told her. “Not even once. Understand?”
She did understand.
She was hesitant about returning next Wednesday. Going an entire week without panties – both at home and at school – had made her feel like a slut. She was always worried that someone would catch a glimpse up her skirt and see her pussy – or worse, see her pussy and see that it was *wet*, because the sense of constantly being exposed was making her very, very aroused. She felt dirty. She felt like she wasn’t really like the other girls at school, because they were wearing panties, whereas she was studying to be a stripper (or a whore, her mind whispered).
And yet the studying – the “normal” studying” – she had done with Mr Jones did make a difference in her maths classes that week, so on Wednesday after school she came back to see him.
The first thing he did was lift her skirt to check she wasn’t wearing panties. She blushed. She had never let a boy deliberately see her pussy before – let alone an adult man – and she knew he could see how soppingly, whorishly wet her cunt was.
“You have a pretty fuckhole, Caityn,” said Mr Jones, and watched as Caitlyn turned bright red with humiliation.
“Oh, does that embarrass you?” he said. “As a stripper, you’ll need to get used to people talking about your body. Sometimes it will be a compliment. Sometimes it won’t be. Sometimes it will be intended as a compliment, but it will still make you feel degraded. Either way, you need to learn to accept it with a smile. Say thank you for my compliment, Caitlyn.”
“Thank you, sir,” said Caitlyn in a small voice.
“Now take off your shirt and bra,” said Mr Jones. “Slowly. So that it entertains me. It will be good practice.”
Caitlyn did her best attempt at a striptease, unbuttoning her school shirt slowly to reveal her white bra, and then uncinching the bra and letting it fall away, to reveal her tits. She felt awkward and self-conscious, acutely aware that she didn’t know how to strip sexily, didn’t know how to please a man.
“Your tits are huge, Caitlyn,” said Mr Jones. “They make you look like a cow. You will be popular as a stripper.”
Caitlyn was mortified. Mr Jones was being cruel to her, she knew – her tits weren’t even that large, on the top end of a C-cup at most – but she knew this was practice, and she knew what he wanted her to say.
“Thank you, sir,” she replied.
They moved on to the tutoring, this time focused on Caitlyn’s English Lit class. Mr Jones stared openly at Caitlyn’s breasts whenever he had the chance, and whenever Caitlyn covered her breasts – or even sat in a way that didn’t thrust them forwards and emphasise them – Mr Jones would stop, and correct her posture, moving her arms out of the way and putting her tits on centre stage. He would say, “You look more fuckable like this,” or, “This pose makes you look more like the stupid bimbo you are,” and Caitlyn would say, “Thank you, sir.”
She blushed and blushed and blushed all the way through this treatment – but the tutoring was good, and she did feel she understood the subject better by the time it was over.
Then it was time for stripping practice – or in this case, as it turned out, lapdance practice. Mr Jones put porn videos on the screen again, and had Caitlyn sit in his lap and grind her ass against the front of his pants. She could feel his stiff cock poking against her anus and pussy through the thin fabric of his trousers, but she obediently wiggled her buttocks and groin against him, and watched the lewd video on the screen. Her cunt was sopping wet and she knew she was leaving a wet patch on the guidance counsellor’s groin – but near the end of the hour she felt him groan, and his cock twitch, and then he was making his own wet patch in his trousers.
She blushed, knowing what she had just done to her teacher. She let him push her off his lap, and then down to her knees between his legs, now facing him. She watched, blushing, as he unzipped his pants, and took out his cock, coated in the cum of his ejaculation. Then, before she could react, he had picked up her school shirt, and used it to wipe himself clean – or as clean as he could.
“You can clean up the rest of the mess you caused with your mouth,” he told her, and grabbed her by the hair, and pulled her face down onto his dick. Before she could think about resisting, she had a cock in her mouth for the first time in her life, and he wouldn’t let her pull away.
With no options, she obediently licked and sucked at his cock, cleaning up the last of his cum, and then he lifted her off his phallus and applied her tongue to his pants and underwear, to clean them as best as she could as well.
Finally, he gave her her shirt back, and told her to go home. He didn’t return her bra, and she understood implicitly that the rules were the same as last week – she was no longer to wear bras, in any setting.
Caitlyn walked home with the taste of cock in her mouth and with dried cum on her shirt.
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