Sandra's Wedgie Gifts

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A bully comes up with a unique wedgie strategy to make money.
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The holidays were supposed to be about buying gifts and having a good time. The problem was that the nerds at her college that Sandra typically bullied had managed to hide from her for the last week.

And so her revenue stream from taking allowances and lunch money (just half of their lunch money, she wasn't a total monster) had dried up like the snow on the ground.

Broke and it's a green Christmas, it can't get much worse, Sandra thought. She kicked the slushy ground as she walked to the park.

She was walking for maybe a minute when she saw a nerd she picked on from time to time. Her name was Casey or something and she came complete with glasses kept together with tape, and pants hiked up past her belly button, bending over by a trash can.

Her butt was facing Sandra. Sandra, a cheerleader and experienced bully, had a lot of ways of picking on the geeks and losers. But wedgies were always her favourite for the way the nerds reacted and how she only had to give the smallest pulls before her targets were reduced to sobbing and blubbering ATMs.

Sometimes it was grody tugging on the underwear of a loser, but Sandra had always been raised with the belief that you had to work for your money. So she sucked up her reluctance and got hold of their gitch and gave a few giant pulls.

This time would be no different. Maybe this nerd would have a few bucks.

Sandra rubbed her hands together. That's when she spotted a second nerd who was facing away but starting to turn towards her. If she spotted her the two of them might run, and she wasn't in the mood to run. Even if the holiday season was all about giving, she didn't need to give a wedgie that bad.

So she leapt forward and before the nerd could stand up Sandra sunk her practiced hands into the nerd's dark pants. She felt the familiar sensation of old and stretchy cotton before she yanked up hard enough to shock the nerd into what Sandra had started to call "wedgie shock."

The nerd was paralyzed and trapped in the moments before her mind caught up with the pain and reacted with squeals and squeaks and other noises to display her hurt.

During the wedgie shock, Casey Somethingorother was feeling a mess of emotions. Humiliation and embarrassment over her underwear--a pair of pink Hello Kitty panties that had definitely been stretched before based on how easily they slid up this nerd's butt--and maybe even a bit of pleasure. Because it was underwear rubbing against you, and if Sandra pulled just right, she could even make the wedgie feel a little good.

"Aiieee!' Maybe Casey whined. "Not another wedgie! I already got my daily wedgie!"

"Yeah, but not your hourly wedgie," Sandra said. She chuckled, lowered her arms, bent her knees and jumped into the next pull, lifting the small nerd off her feet and stretching her panties until a few holes appeared over Hello Kitty's white eyes.

"Cassia!" The other nerd who had been standing nearby watched with wide eyes that didn't know if they wanted to watch the climbing underwear, her struggling friend, or the blonde bombshell of a bully who looked way more athletic than she was even in her dreams.

Sandra gave Cassia's (Casey is better, Sandra thought) underwear another tug.

"What's up nerd?" Sandra said, looking straight at the second nerd. "You want some of this?"

"No mam!" The nerd, who was probably also Sandra's age, said. She hung her head and sighed.

"Nerds," Sandra muttered. She gave Casey/Cassia's underwear another hard tug, and kept the nerd on the tips of her toes, while her taut panties creaked. "Hey loser. How much money do you have?"

"I'm broke!" The nerd whined. "I've been spending my money on new undies. And the video game The Callisto Pro--"

Sandra yanked the underwear hard enough to cut the loser off.

"Nerd, if I wanted to know your life story I'd give you a journalist wedgie." Sandra pulled harder on the underwear and dangled the nerd above the ground until her biceps started to feel the burn. It wasn't as intense as the burn the nerd would be feeling in her crack, but it was enough to know this nerd would have given her money if she had any.

Sandra released the underwear and it drifted back to the top of the nerd's hiked up pants. Casey pushed her glasses up her nose, which had come askew amid the panty-pulling. And with her nasally voice, she gave a sigh of relief.

"You better run, nerds," Sandra said. "And don't pick that wedgie. Unless you want to be hanging on one of these trees."

The nerds jumped and started running as quickly as they could. Sandra followed behind them and after a few seconds she could hear their voices, fading but still clear.

"Wow, that was a rough wedgie! She totally ruined your undies."

"I know! But you know what, I'm so strapped for holiday shopping that I almost told her I'd let her wedgie me for money."

"Too bad she can just wedgie you for free."

"Yeah," the nerd said with a pout. She slouched and dragged her feet as she followed her friend.

"Pay for wedgies..." Sandra muttered. She rubbed her head with a finger. Her blonde hair fluttered in the breeze. "I don't think I can get people to pay me to wedgie them. At least, not in time for the boxing day sales."

She stomped her way through the park until she saw a crowd of nerds all gathered together. Some of them were caroling, some were just chatting and others were dressed up in Christmas costumes.

These were the kind of nerds Sandra would wedgie any day of the week.

She sighed, but a smile crept onto her chiseled face.

If I can't get money I can at least have some more fun giving wedgies, she thought.

Then she stopped mid-step.

Wait. I could try and wedgie all these nerds and hope I get lucky and get some with money. Or I give these losers a once-in-a-lifetime opportunity. They get to wedgie a bully.

Sure, Sandra had never gotten a wedgie before (except for when her thong rode up on its own) but how hard could any of these nerds actually pull?

I'll take a few tugs, make bank and I can always get these nerds back later.

Sandra smiled and patted herself on the back.

"I'm an evil bully genius," she whispered.

She walked towards a group of the nerds dressed in elf costumes, or with reindeer horns on their heads. They all stopped talking as she approached and a few that recognized her started backing away.

"Alright, dorks, listen up!" Sandra yelled. She used her cheerleading voice, which was commanding and carried even to the nerds who were far away. "For one afternoon only you get to give me, the Queen of Wedgies, a wedgie. Five. No ten bucks, buy you one wedgie!"

No one (except herself) had ever called her a wedgie queen, but some of the nerds would know it was true. And even if they had no idea who she was, they were nerds who were picked on and wedgied all their lives. Even the hope of getting to be on the top was enough to draw a few interested people towards her.

"Seriously?" one of them asked. "Only 10 bucks to give you a wedgie?"

'Only 10!' I should have asked for more, Sandra thought.

"Yeah! Now, who wants in on this?"

And after a moment she yelled out again.

"There's limited spots available, so get in line quick!"

One of the nerds rushed up to her. It was Cassia/Casey's friend. A short girl whose head only got to Sandra's breasts. She had a 10 dollar bill in her hand and a fierce fighter look on her face like she had mustered all her courage to do this.

"I'm avenging Casey's honor!"

"Whatever nerd," Sandra muttered. "Let's get this done. And the line forms behind dorkula here."

Casey's nerdy friend deflated at that and Sandra grabbed the cash from her before pocketing it into her tight jean shorts. It was then that Sandra remembered she was wearing a thong--it was better than if it had been laundry day and she was wearing something embarrassing (or worst of all, ew, a pair of granny panties)--but a thong wedgie would probably hurt. Even if the nerds are weak.

Sandra sighed and stuck her butt out for Castle's friend. The nerd struggled to get her fingers into Sandra's tight blue jean shorts, but after a moment she managed it and got a loose overhand grip on the underwear.

Sandra looked over her shoulder and shook her head.

Wedgie amateur, she thought. She grinned. Why was I worried? This will be the easiest money I've made.

The nerd gave a small pull up, enough to bring Sandra's red string-like thong into the air. Nerds around them gasped and a few stepped closer to get a better look.

I should have charged an audience fee. Oh shit, she thought.

"Hey, if I see a single camera capturing this I'm giving you all atomics, got it!"

A few yelps and the sound of the phone hitting the ground echoed in the expectant quiet of the crowd as they watched the ritual of the giver and receiver--a tradition as old as wedgies themselves.

Never thought I'd be on this side, but hey, consider it my good deed. I'm giving all these losers a present, getting to see me like this.

But Sandra's attempts to convince herself weren't enough to silence the growing feeling of embarrassment that was gnawing at her. A crowd of losers were about to see her panties and some of them would even pull on it. This wasn't her, she was the strong one. The bully. The one with power. Maybe this was a mistake. Maybe there was some other way she could make the money.

"Actually," Sandra started to say. But before she could stop this, the nerd gave her first real pull, and even though she was a loser, and her grip was wrong and her stance was sloppy and her angle was more bent than a nerd's back in an atomic wedgie, when the thong surged up her butt, Sandra still felt it. And it hurt.

She yelped and shut her mouth before any other signs of weakness could escape. The red thong climbed up her back, thinning into a sharp-angled triangle that all the nerds could see. The losers started to laugh, point and a few even started yelling.

"Wow, she was serious! We actually get to give her a wedgie!"

"Look at that thong, it's already getting near her shoulderblades."

"I'm so next!"

"Argh," Sandra grumbled. Her hands tightened into fists and she groaned, lifting her head up the sky as the thong bit into her like a shovel into a mound of snow. She was blushing and trying to turn her face so no nerd could see how much discomfort she was feeling, but they started to circle around her. And while none of them had cameras or phones out to record, as far as Sandra could tell, she knew they'd all remember this.

The nerd let go of the underwear and the wedgie, which lasted only a few seconds, but which felt much longer to Sandra and her formerly wedgie virgin butt, ended. Acting on instinct, Sandra went to pick the wedgie--while Casa (or whatever her name was) and her friend reunited. They kissed and started walking away, hand in hand.

Sandra was about to fix her wedgie when another nerd, this one dressed in a full-on reindeer costume (not just the antler hat, but a complete body costume) jumped behind her.

"No need to pick that madam!" The reindeer nerd had 10 bucks in their hand and was waving it towards her. "I would like to take advantage of this serendipitous proposition."

"Nerds," Sandra muttered with a shake of her head. She hung her head low and waited as the reindeer/nerd took hold of her stretched out thong and gave an even harder pull than the first one.

Sandra threw her hand over her mouth and held back a squeal. The nerd gave a few sharp yanks up, without any of the technique that Sandra had practiced, but they didn't need finesse to give hard pulls.

"You nerds have a lot of anger," Sandra managed to say between the pulls that made her thong creak and also stole her breath.

"All the wedgies madam, they trigger us mam!" The reindeer-dressed nerd answered with a dutiful and helpful tone.

Sandra was preparing an insult when they gave the hardest pull yet, tugging from the top of the waistband with enough power that the red fabric tensed into a hard wire.

She was feeling the wedgie shock, the pain, humiliation (compounded by the fact she had a reputation as a popular person) and even a weird sort of pleasure as the thong rubbed her. It was terrible to be seen and laughed at like this. But she had to work for her money.

"OK, next next," Sandra mumbled. She was trying not to squeal, but it was hard as she realized she gave lots of wedgies, but had no tolerance for receiving them. This had to be the most painful money she had ever made.

A line of nerds took turns on her underwear and it wasn't until one nerd managed to rip her already ruined thong--which was now at least three sizes larger than it was when she first put it on this morning--that Sandra was able to take a breath.

"Alright, that's it," she yelled. She let out a sigh. Her butt was burning, and her embarrassment had peaked at like wedgie number six, and hadn't gone away. She lost track of how many nerds had given her thong a pull, but her pockets full of bills helped soften her aching ass and ego.

I'm getting all of them back, way worse than they got me.

Sandra tore herself away from the nerds who were still standing nearby. She gave her best intimidating bully look at a small group of nerds who seemed like they wanted to keep pulling on her ripped thong. Even though she was still blushing and looked rugged, the nerds quickly backed off.

But a few more were creeping towards her. She swallowed and shook her head.

If they all rush me, I don't think I can take them all, Sandra thought. Not before some of them grab the remains of my underwear.

That's when she felt something cold touch her nose and a few of the nerds started muttering among themselves. Sandra looked around and saw some of them were starting to turn their heads to the clouds.

Sandra looked up and after a moment they were all looking up and watching the first specks of white falling from the sky. The nerds ran off, forgetting about Sandra and going about whatever holiday plans they had.

It's snowing, Sandra thought. She was still looking up as the flakes fell on her, and the chill air was just right for cooling her fiery butt and cheeks. Just in time for Christmas.

She smiled.

I have money, snow. This holiday might not be a total disaster.

Now I just have to plan how to make some more money for New Year's.

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AnonymousAnonymous4 months ago

A follow up story where the bully gets bullied for money and the nerds are fully preped please

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