Chapter #2Emily by: Unknown Emily is the very definition of "Girly-girl". With a generous allowance from her wealthy parents, she's able to buy the flashiest, frilliest outfits in order to stand out and above her peers. It was because of this, she was the most popular girl in school during her freshman year, the new girl who could buy everyone's attention and affection. However, as the years went on, people got used to all the pink frills and sparkles, and stopped giving her the attention she demanded. Now in her senior year, she can hardly get people to even look her way, a far cry from the crowds of fans she used to have. And now she's on the hunt, desperate for a solution.
Currently, Emily is finding herself wandering the halls of Underwood High. She's wearing her lucky, pink and white maid cosplay dress1 today, and unfortunately it isn't bringing Emily the most luck, and she doesn't even earn a glance from the busy students. However, the sounds of a rowdy crowd instantly perk Emily's ears up, and she follows the sound until she finds a group of people circled around something. There's too many people in the way for her to see what they're all excited about, so she pushes her way through the crowd until she finds what is riling them up: one of the cheerleaders was in the process of giving one of the well known nerds of the school, Pearl, a monster wedgie!
Emily watched as the blondie gripped and stretched Pearl's massive white granny panties, ripping and pulling until the white fabric was firmly pulled over the squealing nerd's chin.
'This is what got so many people together? A wedgie?!' Emily thought to herself, excitement brewing in her heart as a spark of inspiration began to bloom. She instantly pulled herself from the cheering crowd, driven by the possibility that it would be her next that they would be ravenous for. She was on the hunt for one girl: Desmona. It was well known around Underwood High that Desmona was one of the most infamous bullies around, normally people would want to avoid the Amazonian woman at all costs, but Emily was not a normal person.
After half an hour sprinting around the school, at a surprising rate too given that she had on tall, plastic high heels, she finds Desmona at the back of the school, squatted down and spray-painting an anarchy symbol on the brick wall. Even crouched down, Desmona had an intimidating aura, her long blonde hair was pulled into a long braid like a viking warrior, and if she were standing upright, she'd be at least 6' tall. Her intimidating stature is only amplified by her black biker leather outfit2.
"DESMONA! I'LL PAY YOU TO GIVE ME A WEDGIE!" Emily suddenly burst around the corner, startling the anarchist.
"GAH!" Desmona squawks, flinging her paint-can out of sheer reflex. The can sails through the air and directly bonks right into Emily's forehead. The impact completely stuns Emily, making her flop right onto her back in a comedic way onto the grass.
"What the hell do you think you're doing, you crazy bitch?" Desmona leans over and asks the sprawled out girl. However, Emily doesn't stay down for long. She suddenly springs back up to her feet, making Desmona need to jump out of the way.
"I've been looking for you! You're exactly what I need to get popular again! I'll pay you $20 to give me a wedgie in front of the school." Emily chirps happily, pulling out her wallet and revealing her large stash of cash. After processing what Emily said, Desmona certainly was skeptical, until she laid her eyes upon Emily's small fortune.
"Make it $50, and you got a deal." Desmona crosses her arms, expecting Emily to begin bartering the price.
"Done!" Emily doesn't even hesitate to pull out a $50 bill, as she's hellbent on getting that damn wedgie. Desmona blinks in small bewilderment, but gently takes it from Emily's outstretched hand.
"Alright, lets get going, Princess. You know what you're getting yourself into? I'm not going to hold back." Desmona warns as she begins to walk with the strange, frilly dressed girl.
"Absolutely... Although, I've never really gotten a wedgie before. How bad could it be?" Emily asks with innocent curiosity, making Desmona chuckle.
"So, you're paying me to take your wedgie virginity too? Don't worry Princess, I'll make sure it wont be forgotten." Desmona ruffles Emily's hair a bit, making Emily coo with delight.
"Wonderful, I knew I could count on you!" Emily's excitement only grows exponentially as they enter the entryway of the school, which was already a gathering place for many of the students as lunch was starting.
"Well, it's time for me to do my part of the bargain. Let's get started." Desmona cracks her knuckles before gripping the back of Emily's dress.
"Wait, those aren't my panties, I told you to give me a--"
SHHHHRRRIIIIIIPPPPP
Without any warning, Desmona rips off Emily's dress, tearing the fabric like a wet napkin, and leaving the girly-girl in utterly nothing but a pair of frilly white panties3 decorated with a small chibi bunny onto of an equally adorable unicorn. Instantly, Emily's face turns to a vibrant beet red as the cold air makes her skin get covered in goosebumps and her soft pink nipples of her B-cup boobs perk up. However, before Emily could even react to cover herself up, Desmona grabs two greedy handful's of Emily's frilly panties and heaves them up, driving the stretchy fabric deep up Emily's ass as she gets catapulted off her feet by a mega wedgie. The sound of her dress being shredded already gained a lot of attention, but the shrill, ear-piercing squeal that followed as Emily gets bounced up and down like a yo-yo grabbed the entire floor's attention.
"Oh my god! Look at Emily! Desmona's made that annoying rich brat her little bitch!"
"What kind of childish little panties are those! She's just begging for a wedgie with those!"
The crowd begins to hoot and holler as Emily is utterly wedgied and humiliated in front of them. The ripping pain cleaving up Emily's ass and the exhilarating sensation of being the center of attention is almost too much for her to handle, as this was even more than what she could have dreamed would happen.
-------------------
Option 1: Emily's panties finally rip from the brutal torment, giving her a moment to get a new outfit and pair of undies for another wedgie round at a later time.
Option 2: Desmona decides to hang her up somewhere, giving her a hanging wedgie on the house and letting Emily get herself down.
Option 3: Desmona decides to pull Emily's panties tightly over her face in a brutal atomic wedgie, and leaves the rich-girl at the mercy of the ravenous crowd.
Option 4: Emily continues to get bounced by Desmona, giving the bully a chance to transition from a bouncing wedgie to some other form of wedgie or humiliation.
Option 5: All this excitement goes to Emily's head, and she loses control of her bladder in front of everyone! Leading to a whole new realm of humiliations for the girl to experience.
Image references:
1 (Emily's outfit): https://images-wixmp-ed30a86b8c4ca887773...
2 (Desmona's outfit): https://images-wixmp-ed30a86b8c4ca887773...
3 (Emily's panties): https://images-wixmp-ed30a86b8c4ca887773...
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