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Old December 18th, 2023, 05:23 PM   #31
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Cyrus coughed awkwardly. "Well...yes of course. I hate having to do this. It's really unfair that you have made me do this to you," he said, partly trying to convince himself, though even he did not find his words convincing. As he fiddled with her waistband, he silently appreciated her help as he struggled to slide her tight pants down her voluptuous thighs.

"This is your second spanking in two days," he admonished her. "Of course it's going to be worse. You don't get the protection of pants this time." He was surprised to see her bare cheeks in her thong. Surely she thought there would at least be a possibility of her getting spanked again today. Did she wear the thong on purpose? No it had to be an accident.

He started to smack her bare cheeks, but was surprised by the bare cheek of her retort. "Do their homework for them? NO! NO! NO!" He punctuated his last words with spanks on her wide bottom, with strong spanks pushing her pelvis into his thighs. "You are a teacher, damn it! You can help them with their homework and motivate them to work hard, but no cheating!"

He eyed his black bag and moved it next to him with his foot. He stared at it, wondering if it was time to use it.
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Old December 18th, 2023, 10:23 PM   #32
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Because he was just lazy? Or because she looked more ridiculous this way? It was a little mystery why he elected to pull her trousers only halfway down instead of removing them fully. Regardless, feeling them accordioned around her legs was a constant reminder that her bottoms were indeed lowered. Maybe that was the point. As for her thong.. Well, she simply didn't want to give herself some terribly unfashionable ptl. And since her underwear exposed most of her cheeks anyway, perhaps it wouldn't be a necessity to bare her further.

“I know how to count, thank you,” she felt the need to say, hoping that she wouldn't have to be in this awkward position a third time. “Thiiis time?” Carmen protested still, the pitch of her voice getting higher. “I didn't even have trousers last time.”

Normally, she would have only appreciated anything that made her feel younger. Not through spanking though. It almost felt like she was back in her school days while lying across a lap for this particular activity. “Oww. Oww!” Her springy bottom was like a French dessert, melting when whacked, and setting back when left untouched. “Sarcasm. Ouch! Sarcasm,” she explained herself. Of course she knew better than to do their homework herself as an educator. The harder smacks joking about that earned Carmen made her wide bottom wider as her cheeks sort of spread out more under the pressure.
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Old December 19th, 2023, 08:52 PM   #33
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"Well if you know how to count, you'll know that I warned you what would happen if you were neglectful again," he scolded still smacking her bottom watching her cheeks wobble briefly before perking up after each spank. "And since you received a bare bottom spanking last time, you deserve at least a bare bottom spanking again this time!" he said as he pulled the waistband of her thong, again stopping them at her thighs. Indeed, it did seem like more of a punishment for them only to be partially lowered...a reminder of her helpless state.

"Well it's not like that thong covered much," he said, lightly pinching one of her butt cheeks. "But it's about the embarrassment..." He spanked her now fully revealed bottom, while pondering to himself. Would a more painful or a more embarrassing punishment suit Carmen today. "I think more embarrassment is needed for you to clearly remember the lesson, Miss Carmen," he said, growing bolder at having his former teacher bottomless and vulnerable, draped across his lap.
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Old December 19th, 2023, 10:13 PM   #34
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It obviously depended on what she wore at the time, but it wasn't that unlikely to make accurate guesses after a glimpse or two about her bottom’s wobbling tendencies. It was unlikely, however, to actually verify that. In this particular case, this certain activity was a foolproof way of checking it. Of course, Carmen wasn't very proud of demonstrating it.

“Well it’s called giving it time and thought,“ the woman tried to explain. In most cases, progress was only possible with patience after all. “You can't expect a miracle in a single day.” Apparently, his patience only lasted a few smacks before giving in to the desire to see her bottom fully bare. She supposed all that ‘bare yesterday bare today’ talk was meant to lead to that.

After overcoming her trousers, her thong must have felt flimsy. “I teach chemistry, you know..” Carmen said, feeling that flimsy little thing gliding smoothly on her skin. The bottom of her underwear clung to her bits while the rest slid down. “Not biology.” Following an ever so subtle snap, the fully disconnected undergarment continued its downwards trip to join her trousers. “It did cover enough,” Carmen argued, believing that she didn’t need to admit that this was indeed embarrassing for her, or to tell him to unsee this once he left. And it was supposed to be more embarrassing still? “What do you mean exactly?”
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Old December 21st, 2023, 03:39 AM   #35
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Cyrus explained "I know it won't be night and day improvement. But I think you deserve punishment everyday until I see the improvement." Cyrus watched her cheeks ripple after each spank. "And I talked to them, and I don't feel you gave them adequate instruction. And that's also why today's punishment must be worse."

Cyrus smiled as she argued her thong covered enough. "All the more reason to remove it then," he quipped back mostly to himself. But now it was time for him to make the big play he intended for the day. He took a deep breath and pulled an object out of his black bag. It was a black silicone butt plug. "I think you should wear this for the remainder of your punishment today. It's purely as an embarrassment tactic to motivate you to improve. That's all." He said tersely.
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Old December 21st, 2023, 10:01 AM   #36
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Among all the talk about improvement, it sounded like some home improvement was taking place in the living room given all the hammering happening. The removal of her knickers didn't change how her bum behaved under pressure. Apart from the very core, things didn't look much different either. “Oww! I’ll start giving them proper instructions immediately. Oww!” Carmen claimed. In truth, she didn't quite know what kinds of instructions he meant exactly, but agreeing to it was much more preferable to questioning it during a spanking.

A new pair of knickers? With a silly pun written on the back? Bought as a meaningful gift of sorts? Carmen asked these questions in her head when putting her shapely bum in a different piece of clothing was mentioned. Putting something in her shapely rather, she’d yet to find out. “Wear what?” she looked back. “What?!” and asked again upon seeing it. Unmistakably, it was an anal plug what her eyes widened at. Her surprise lasted. “A bloody what? Cyrus!” As far as embarrassments go, that would indeed be a final nail in the coffin. A thick one at that. “You can't just- I'm your- Do you know how to use it even?”
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Old December 27th, 2023, 05:54 AM   #37
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<Sorry, was out of town>

Cyrus lightly shaked the plug, watching it wobble, not completely unlike Carmen's bottom after a spank. "A well...it's not like rocket science...I'd Imagine...I just have to part your cheeks and then put it in..."

Cyrus shook his head. "Listen it's just a precaution," wondering to himself what he even meant by that. "Let's start this," he said as he gently began to spread her bottom, prepared for the insertion.
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Old December 27th, 2023, 01:48 PM   #38
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Usually, they weren’t that wobbly. No. Not her cheeks. Toys with this particular use. Not that she knew a whole lot about them! And on their usage... Technically, that was the idea, spread and push in. At the same time, calling it simple was a giant understatement. “Should have contented yourself with just imagining…” the teacher grumbled. “Actually not even that. Why would you imagine that!” Even for her former students, it wasn't such a deal frankly to have her bum appearing in their dreams on occasions. If she was indeed so eye-catching back there, they could even fantasise about a pat on the bottom. Though, plugging her arse was surely far beyond any of that.

“Unbelievable…” Carmen, still across his lap, flipped her hair. In an anxious state, her eyes shifted about while Cyrus spread her ample cheeks, practically leaving nothing unseen about her below the waist. Her ample cheeks dwarfed the little star that showed up between them. With a sudden protest, she pulled her arms back, putting her hands together around the centre of her bottom. “Huh? You can’t insert it like that when it’s dry!”
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Old December 27th, 2023, 10:30 PM   #39
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Cyrus would be lying if he denied fantasizing about Carmen during school. She was his favorite teacher, and her round bottom provided visions of him spanking her...and more. "This isn't just a fantasy," he replied, being half truthful. It was a fantasy, but it was also for discipline purposes...right?

His first gaze at her bottom hole left him nearly breathless. It was real, right? He was really seeing Carmen with her naked posterior draped across his lap and cheeks spread and vulnerable parts exposed? He snapped back to reality with her critique. "Yes...of course, I know," he said, though truthfully in his excitement he had forgotten to lube it. He took a bottle of lube from his bag and squeezed it on the plug and spread it out with his strong wide palm.

He then squirted some lube between her spread cheeks. He positioned the plug at her entrance. "Ready?"
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Old December 28th, 2023, 12:14 PM   #40
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Babysitting jobs usually didn't come with such unlikely opportunities dropping into the sitter’s lap. Dropping literally in this case. Alright, more like, gingerly lying across it. Anyhow. This was the risk of making open ended deals and bold claims.

Thanks to her generous backside, Carmen could have probably kept enough eggs necessary to make fresh pasta warm had she been a chick. The hindquarters weren’t self-heating though. She felt cold when the lubricant was applied, goosebumps rising on her skin. Hopefully, it was a compatible one that wouldn’t break the wobbly silicone material that was apparently bought for her bum. Well she knew about these, because she taught chemistry.

“I’ll give you the benefit of the doubt and pretend this is not your fantasy and,” she paused as he spread and lubed, which felt as awkward as it sounded, “this is not the first bum you do this to.” One look at the toy, and another at her opening should tell that it wouldn’t be easy for Carmen to be completely ready for it. “No?” she said so as well. While thinking, she looked to the right. And to the left. Her eyes rolled between two points. “I guess, the faster we be done with this the better,” Carmen sighed. After more consideration, she added. “Actually, I take back the fast part.”
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