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Tuesday, September 10, 2019

ChaperPWNed 2

Greetings! Our hapless chaperone is back for more Spring Break hijinks.

The caption was just too big to fit the picture this time, and try as I might, I just couldn't find another set of pictures that fit as well as this one, so I'm going to just post the text as a mini-story itself.


***



"I never should've taken that sleeping pill," Principal Barbara Dahlton muttered to herself, scanning the crowded beach.

After a long night spent sandwiched snugly between sixteen Senior boys in the middle of a huge heart-shaped bed, she'd finally awoken at noon, only to find that her teenage charges had disappeared.

Thankfully, the boys had left her a note, at least, though it had been tucked rather inappropriately between her firm breasts. "Gone to find you some clothes, Miss Barbie. Meet you on the pier at One. Oh, borrowed your credit card too."

Barbara narrowed her eyes, struggling to find her charges among the beach's frolicking horde of half-naked Spring Breakers. It had to be well past the promised hour.

"Where are they?!" she growled, impatiently. It was bad enough just being outside the hotel in this ridiculous outfit, but if those boys didn't return soon, she'd have no choice but to start searching the whole town for them. She sighed, forcing herself to calm down again. "I guess it was nice of them to try to find me something else to wear, even if they did steal my credit card again."

She waited several more minutes, ducking behind a pier as a couple of college kids wandered past. One of the girls was holding her real clothes, having just left the changing rooms farther up the beach. Barbara fought back an urge to beg the girl for her blouse, but couldn't stand the thought of revealing herself. Maybe when the boys returned with her credit card, she could get them to offer to buy some clothes from the fellow hotel guests....

"Barbie! There you are!!" The sudden voice made her jump, which very nearly sent her breasts out from their hiding place. The Senior Class President waved at her, running up to her with the rest of the missing boys. "What are you doing down here? Didn't you get my note, you were supposed to meet us on the pier, not under it?"

Barbara fought back an urge to yell at him, as several of the cohort grinned, clearly remembering exactly where their ringleader had left the note.

But before she could respond, the Senior boy shook his hands, waving the question away. "Oh, nevermind. So, good news, we found a shop on the other side of the island that still had some clothes for sale."

Despite her situation, Barbara's heart leapt at the boys words. "You found real clothes?!" She looked the boys over excitedly, but frowned when she saw no shopping bags. "Well, where are they? And where is my credit card, for that matter?"

The class president gave a sheepish shrug. "Yeah, about that... so, we sort of... maxed out your card before we found the shop. The clerk cut it up."

"But, that's impossible, I had at least a thousand dollars left on it when we arrived yesterday and all you've bought so far was--" Barbara stopped. She looked down at her skimpy outfit.

"YOU SPENT ALL OF MY MONEY ON THIS PORNSTAR OUTFIT!!!?!!!"

"Of course not," the teen assured her, "we only spent like $200 on that."

She started to continue her tirade, outraged that her minuscule outfit had cost even that much, but stopped herself. "Wait, so where did the other $800 dollars go?"

"Oh, we took that out this morning, to enter you into the contest." A loud air horn sudden blurted from above them. "Ooh, speaking of which, sounds like it's starting. We'd better hurry, you're going to be late, Miss Barbie. You're contestant number one!"

The boys suddenly grasped her arms, tugging her out from her hiding place and toward the proper entrance to the pier. "Late for what?!" she gasped out, as they hurried her along the hot sand. "And what sort of contest costs $800 just to enter, anyway!?! Shouldn't they be paying the winner a prize, or something?"

"Oh, no, the entrance fee was like $20; the rest of the money was to bribe the judges. First place winner gets $5,000. If you win, you'll be able to buy out the clothing store, with plenty left over."

She considered the teen's statement, as they reach the start of the pier and she was hoisted onto the wooden deck. $5,000 was nothing to sneeze at, especially on her salary. If she won, she'd make enough to go on a real vacation, once this week was over.

"Well, I guess I can't argue with that logic. And if you've already bribed the judges, I guess I'm a shoe-in to win anyway."

The boy shook his head, as they made their way down the long deck toward a stage surrounded by young Spring Breakers. "Oh, no, the bribe wasn't to get you a good score. We had to bribe the judges to let you enter."

"Why?" she asked, distractedly, as they finally pushed through the crowd. The stage was already crowded with young women, all in long cotton shirts. The Class President grinned.

"It's a wet T-Shirt contest, Miss Barbie, and you don't have a real shirt to wear. But thanks to our little bribe, the judges agreed to let you compete topless instead."

***

And for those of you who prefer a proper caption, this is what the first part would've been, had I found a suitable image for part two:


As always, hope you enjoyed today's caption. I've also put a new short cap up on my bdsmlr page, and I think I'll be posting more of those short caps there in the future, rather than letting them clog up this site.

- B-Rex

3 comments:

  1. At 15 August you post a story "Stepmother Knows Best".
    @ when r you writing part 2 ?

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  2. Great work, especially love the card getting cut up and putting her at the financial mercy of her students. It sounds like you reached the end of inspiration for it, but I hope there's more some day.

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  3. Not your VERY best work, but I have been enjoying the progressive downfall of Barbara the chaperone as you go along.
    I wonder what will be next...?

    ReplyDelete