The Punishment

Miss Pickering called Tasha into her office. When the poor girl got there, she saw that Miss Pickering’s desk had been cleared off and on it was arrayed a flexible, supple cane, a large black butt-plug and a stack of pornographic magazines.

Tasha looked miserably at the ground, her face turning bright red.

“Tasha, do you recognize any of these things?” said Miss Pickering.

Tasha did recognize them — the pornographic magazines had been hidden under her mattress.

“Yes, Miss Pickering.”

“Which items do you recognize? Pick them up and give them to me.”

Trembling, Tasha walked over to the desk and picked up the paddle and cane, handing them to Miss Pickering.

“That’s all you recognize, Tasha?”

Tasha looked up nervously.

“Yes, Miss Pickering. That’s all I recognize.”

Miss Pickering looked the girl up and down.

“Tasha,” said Miss Pickering. “Lift your skirt and take down your panties.”

Face reddening more than ever, Tasha obeyed, as she had many times before. But never with Miss Pickering. Never here, in her office, with a bare-bottomed birching awaiting her.

She lifted her short plaid skirt and wriggled her bottom as she took her panties down her thighs and let them fall to the floor around her ankles.

“Give them to me,” said Miss Pickering.

Tasha stepped out of her panties and handed them to Miss Pickering.

“What the hell are these?” asked Miss Pickering. “Tasha, these are contraband. You were issued a G-string upon induction here –”

“It goes up my butt!” blurted Tasha.

“As a G-string is meant to,” snapped Miss Pickering, raising her voice. “Tasha, from now on you will go without panties each day. Do you understand?”

“Yes, Miss Pickering,” said Tasha dejectedly.

“Now lift your skirt again and show me your bottom. And spread your legs as you do it.”

Tasha obeyed, leaning forward over Miss Pickering’s desk as she lifted her skirt just enough to present her bare bottom to the angered schoolmarm. This placed the stack of pornographic magazines well within her gaze. She could feel the familiar heat inside her beginning as she surveyed the top magazine, one called “BACK DOOR WHORES,” with its naked blond on her hands and knees, ass in the air, with garish legends promising “MAJOR BUTT ACTION!” and “SLUTS WHO WANT IT!”

Am I a slut who wants it? wondered Tasha to herself as the heat grew inside her.

Miss Pickering tsked as she ran her fingers over Tasha’s naked ass. Then she reached between Tasha’s legs and felt her pussy.

“Shameful,” said Miss Pickering. “You’ll get 10 strokes. Count them.”

“Yes, Miss Pickering.”

Tasha’s eyes filled with tears as she awaited the first blow. She had been caned before, but never by a true sadist like Miss Pickering. All the girls knew Miss Pickering was the one who would truly hurt your bottom, would make it black and blue and make you cry.

Tasha was crying already.

The first blow struck with the sizzling heat of a wildfire. Tasha squirmed and moaned “One,” but did not drop her skirt. Then another blow came, and Tasha chirped “Two!” with a pained tremble to her voice. Then another, “Three!” and another, “Four, oh, oh, oh, ow, ow, ow!” each one cutting into her with fierce pain. Finally, on the fifth stroke, Tasha gasped and moaned “F — five — !” as the pain of the blow settled into her bottom; she slumped forward and threw herself across Miss Pickering’s desk, her face now pressed to the porno magazines, so close she could smell the rank scent of their well-used pages, many of which were stuck together. She could also smell the sharpness of the well-serviced butt-plug, which had not been washed since the last time it was used.

Miss Pickering lifted the hem of Tasha’s skirt with the end of the cane. It had fallen down when she had slumped forward over the desk.

“Tasha, if you can’t keep your skirt lifted,” said Miss Pickering, “then take it off.”

“Miss Pickering?” gasped Tasha through her pain.

“Take it off! And spread your legs for the rest of your punishment.”

Chastised, Tasha unzipped her skirt and let it fall in a plaid pool at her feet. She stepped out of it and spread her legs again, but the bottom of her blouse hung as low as her behind. Tasha knew what was coming.

“The blouse, too,” said Miss Pickering. “Take off your blouse.”

Tasha obeyed, looking at Miss Pickering sheepishly as she exposed her breasts to the woman’s gaze.

Miss Pickering eyed the fetching fullness of Tasha’s bosom. “No bra, Tasha?”

“No, Miss Pickering.”

“Tsk, tsk,” said Miss Pickering. “Now bend over my desk.”

Tasha obeyed, leaning heavily against the desk and spreading her legs, her pert bottom now fully exposed, her face pressed hard against the pornographic magazines as she drank in their smell and that of the butt plug, also close by. Her nipples hardened against the cold wood of the desk as she prepared to be birched again.

The next blow came, and Tasha’s whole body, now naked except for her Mary Janes, twisted and writhed as she whimpered “Six.” Another blow, and she moaned “Seven,” her ass lifting higher in the air and wriggling back and forth as she struggled and tried not to cry out. Still another blow, and she yelped in pain, only half managing to annunciate the word “Eight!” With each blow, angry red stripes appeared on her pale bottom to complement those that were already there. When Miss Pickering landed blows nine and 10, she did it so fast Tasha had to count them both at the same time. Just like that: whack-whack, first across one pert cheek of her bottom, then the other, in a crosswise tangle of agony as Tasha burst into tears, weeping: “Nine! 10! Oh God oh God oh God…”

“Tasha!” snapped Miss Pickering. “What did I tell you about taking the Lord’s name in vain?”

“I’m sorry, Miss Pickering.”

“Don’t apologize to me,” said Miss Pickering with a sneer. “Apologize to the baby Jesus.”

Tasha raised her eyes skyward, taking a deep sniff of the rank-smelling magazines before saying “I’m sorry, baby Jesus.”

Miss Pickering put her hand on Tasha’s bum again, running her fingers first over the angry red stripes she had just placed there, then over the faded, purpled ones — three days old, she estimated, and the more faded, yellowish ones — perhaps a week or more.

“Tasha, how did you sneak the cane into your room?”

“I slipped it into the back of my blouse and put it down my skirt, and walked very upright back to my room,” said Tasha nervously.

“I assume Corinna was involved?”

“She used it on me,” said Tasha. “But I didn’t use it on her.”

“She’s still very naughty. Tasha, you know that all punishment at this institution is to be approved by the teachers. You remember why your punishments were withheld, don’t you?”

“Yes, Miss Pickering,” said Tasha. “I was giggling in class.”

“That’s why I’ve prepared this stack of pornographic magazines for you. They’ve all been well used. You are to study each and every page of those magazines after lights-out, Tasha, with that butt-plug inserted. It belonged to Cassidy, but she’s an advanced student; she doesn’t need it any more. And you will touch yourself while you do it, Tasha, rub yourself until you come. Perhaps that will teach you not to giggle during a pornographic slideshow about the proper technique for receiving anal sex.”

“Yes, Miss Pickering,” said Tasha.

Miss Pickering’s hand traveled up Tasha’s thigh and gently stroked her pussy, which was so moist it was sending streams of juice down her thighs. Tasha moaned and pushed herself back against Miss Pickering’s hand. Miss Pickering slid two fingers in and began to fingerfuck Tasha as she clawed at the desk, sending anal porno mags scattering everywhere. Thrusts of Miss Pickering’s finger struck Tasha’s G-spot and brought her almost immediately to a thundering, moaning orgasm. As she came, her knees buckled and Miss Pickering had to put her arm around Tasha’s waist to keep her from sliding off the desk and falling to her knees.

When Miss Pickering was done, she placed her fingers very close to Tasha’s face. Tasha licked them clean obediently.

“Do you think it’s acceptable for a 33-year-old woman to giggle when she’s being taught how to take it in her back door?”

“No, Miss Pickering,” said Tasha sheepishly. “I’m sorry.”

“Your husband spent a pretty penny to send you to this program,” said Miss Pickering. “I’d hate to think you weren’t getting the full benefit out of it.”

“Now,” said Miss Pickering. “Behave in class, learn how to take it in the ass like a good little slut, and you’ll get your punishment privileges returned. In the meantime, I hope today’s caning has reminded you how much you want your punishment privileges back. Did that little slut Corinna punish you as well as I did?”

“No, Miss Pickering,” said Tasha.

“From the looks of those stripes on your backside, she certainly didn’t. All haphazard and ill-placed. I bet she didn’t even make you come afterwards.”

“No, Miss Pickering,” said Tasha sadly. “She didn’t.”

“Remember that, the next time you want to circumvent the rules. If you’ve learned your lesson, you’ll end up right back here getting what you want, instead of settling for that roommate of yours.”

“Yes, Miss Pickering,” said Tasha.

“Now get dressed. You’re late for oral sex class.”

“Yes, Miss Pickering,” said Tasha, gathering up her clothes.

Good Vibrations

Good Vibrations is the premiere sex-positive, women-principled adult toy retailer in the US. An iconic brand and one of the world's first sex toy shops to focus specifically on women's pleasure and sexual education, Good Vibrations was founded by Joani Blank in 1977 to provide women with a safe, welcoming and non-judgmental place to shop for erotic toys. Good Vibrations has always included all people across the gender spectrum, and is a place where customers can come for education, high quality products, and information promoting sexual health, pleasure and empowerment. Customers can shop Good Vibrations' expertly curated product selection across any of its nine retail locations or on the website, where they can also find a wealth of information pertaining to sexual pleasure, exploration and education.

You may also like...