Wedgie Tax: Part 1 (F/M Wedgie Story)

Leon could feel his heart pounding. His fingers were cold, and he cold sweat was running down his back.

"Oh, why in the world did I ever agree to this?" - Leon thought, as he walked through Mulberry Park to a meeting he'd been dreading since yesterday.

As usual, the park was deathly quiet. Ever since it was abandoned ten years ago, almost nobody came here and the place was in total disrepair.

The path was suffocated by the overgrown trees towering over him. Their thick branches completely enveloped the path Leon was walking on, and he felt like they were watching his every move, ready to strike the moment he turned his back on them. Even now in the middle of the day they looked creepy.

All manner of junk was littered throughout the place: there was a carpet of broken bottles and plastic wrappers all over the ground, old tattered clothes were hanging from branches and thrown across the ground, crusty with dry mud.

After a couple of minutes down the dilapidated trail, the boy came across a gap in the thicket. He recognized it by the white piece of fabric hanging from one of the branches. He sighed. He remembered very well what that piece of fabric used to be...

Making his way through the thicket, Leon finally reached a small clearing. It looked unassuming, apart from a big oak tree in the middle of it. A tree he was intimately familiar with. If you knew where to look (and by virtue of his many painful memories, Leon knew exactly where to look), you could see pieces of white fabric hanging from some of its lower branches.

He put his backpack against the tree and looked around, but there was no sign of Cassidy. Strange. On Fridays, her classes ended earlier than Leon's. Why wasn't she here? Suddenly, he felt a sharp slap on his left shoulder which nearly knocked his glasses off. He heard a feminine voice:

"Hey, Leon! How's my favorite little nerd doing?"

He turned around and he felt a familiar, sinking feeling. You'd think he would have gotten used to this, but every time he saw Cass, he felt the same dread as the first time he met her.

As usual, she had her blonde hair in a ponytail which exposed the partial buzzcut along the back of her head. She wore black cargo pants, and a loose, unzipped black hoodie. Her T-shirt was plain, except for a logo depicting two people doing Brazilian Jiu Jitsu.

Even though she was the same age as Leon, Cassidy was a couple of inches taller than him. Her loose clothing hid her tomboyish form well, but he knew that those loose fabrics were hiding an athletic figure with broad shoulders, wiry muscles and thighs strong enough to crush a melon.

Leon couldn’t help but be transported to when high school began - the moment when his life became a living hell. From the first moment he saw her, he was scared of her. Like a predator stalking its prey, she had immediately pounced on him.

She used to take his lunch money, make him do her homework and wedgie him during recess in front of his friends. Pretty soon, Leon became a pariah, as no one wanted to be seen in public with someone as pathetic as him.

But one day, near the end of their Freshman year, Leon had an idea. The homework he had given her was wrong. And since Cassidy wasn't all that bright, she couldn't tell the difference. She failed the class, and was - predictably - furious.

But before she could unleash her fury on him, he offered her a deal she could not refuse: he would give her homework that's correct and in exchange, she wouldn’t wedgie him in school. Instead, they would go somewhere private where she could do whatever she wanted with him. She agreed. Not before making sure he couldn’t walk straight for a week, of course.

Now here they were, in their Senior year. It had been four years since their arrangement, and Leon was still just as nervous as if it was his first time meeting her.

"Oh! H-H-Hi, Cass..." - Leon stammered, "I guess you’re g-g-going to want..."

"I’m going to want to give you a wedgie?" - she said with a huge grin. Leon shivered.

"Patience, Lose-on! I need to see the goods first!"

“Lose-on” he thought. That was probably the dumbest name she’d used yet. It seemed to be a pattern with her - the dumber the name, the longer Cass would use it.

Leon sighed as he took out a blue folder, and handed it to her. She quickly leafed through it as Leon told her what was in it. His heart was pounding and his fingers were getting cold from the anxiety:

“It’s all there - Math, Biology, Chemistry... And like I said, I’ll have the essay ready by Monday.”

“And it’ll get me an A?”

“Yes, of course! You know I’ve never let you down!”

She frowned:

“I can think of one particular time…”

He gulped.

“Ok, I guess that’ll have to do.” Cass said as she put the folder down. She crossed her arms. “Assume the position.”

He felt a thick lump in his throat. Like every other time, he hoped she would forget about that part of their arrangement. But just like every other time, she didn’t.

Leon sighed and turned around. With a sense of foreboding, he realized that this routine had become second nature to him. He bent over and pressed his hands against the oak tree. He spread his legs apart, slightly beyond shoulder width, and he arched up his butt.

Cassidy let out a small giggle as she moved in closer:


“You’re such a good nerd! You even stuck out your little butt, just the way I like it!”

His cheeks blushed a light pink as he felt the backs of her thumbs slightly pull back on his jeans.

He felt her grab the soft waistband of his white briefs and slowly pull it out of his jeans. She giggled:

“Tighty whities again? Leon, do you actually like getting wedgies? Or does your mommy still buy you undies?”

He face blushed a deep red, as he mumbled:

“She never listens to me…”

Cass laughed as she slowly pulled up on Leon’s waistband. The slight tug worked the tighty whities snugly between his cheeks, giving Leon an uncomfortable sensation. Right now, his underwear was in a sort of natural wedgie, the kind you would be used to having if you wore briefs all the time. But he knew that Cassidy was just getting started.

Instinctively, he tried to clench his butt, in the vain hope that it would make the wedgie hurt less. But with his legs spread out, all he could feel was the back of his thighs getting stiffer - his butt remained relaxed. Somehow, that made him feel even more vulnerable.

“You are so pathetic…”

Suddenly, Leon felt a sharp pain in his butt as Cass quickly hoisted the tighty whities up his back. He let out a grunt as he felt a burning sting between his cheeks, which was getting more intense by the second.

She kept pulling on his underwear and he could feel more of the fabric getting crammed into his crack, leaving a sharp, searing pain wherever it passed.

With a grimace, Leon looked back and saw that his white briefs were standing a solid eight inches above his waist, the leg holes clearly visible. He knew exactly what was coming next.

With a giggle, Cassidy switched her grip from Leon’s waistband to his leg holes. But instead of getting tighter, the wedgie actually got a little looser. Leon knew this was only a temporary reprieve, as he saw Cass bending her knees and slightly pulling down his tighty whities.

“Liftoff!!!” - she shouted.

Cass yanked up the white briefs, rocketing them up Leon’s butt and lifting his feet an inch off the ground.

With nothing left to support him, his weight was now entirely resting on the tighty whities wedgied deep inside his butt, which were now splitting his cheeks like a thong. The thin white fabric was cutting into him, and the front had become so tight that it was crushing his testicles.

He could feel the elastics on the front cutting into the sides of his groin, just as the back of his briefs was slicing deep into his butt.

Unable to hold the pain anymore, he gave off a high-pitched scream:

“OWWW!”

Cassidy giggled maliciously:

“I love it when you squeal!”

Suddenly, Leon’s undies gave out a pop. Cassidy allowed his feet to touch the ground and repositioned herself closer to him. She still held the briefs high, maintaining the pressure on his butt and crotch.

As soon as his feet touched the ground, Leon spread out his legs again. He knew better than to break his posture and give Cass a reason to increase his punishment.

Leon saw her widening her stance and he took in a sharp breath, bracing for the torture to come.

Cassidy bent her knees again and readjusted her grip on Leon’s leg holes. Suddenly, she shot up, taking the tighty whities with her. She lifted Leon off the ground again, this time a little higher. Then, she took him down by an inch or so. While he was flying down, he felt a brief moment of relief as the pressure of the wedgie suddenly decreased. Alas, the moment passed, because just as his feet were about to touch the ground, Cassidy pulled up on the tighty whities, lifting him off the ground again:

“Bouncy-bouncy!” - she giggled, taking pride in the world of pain Leon was in.

His eyes were welling up with tears as he felt his white briefs getting rammed further and further up his butt, and his balls were getting squeezed ever more tightly.

Suddenly, he started hearing popping sounds, which were getting louder and louder as his poor, abused undies were finally starting to tear. He was almost glad to be hearing that sound, because each pop gave him a millisecond of reprieve from the excruciating pain, as the material was getting looser and looser with each pop. The reprieve was always short-lived, of course, as Cassidy made sure to always keep the white briefs taut.

“Do you hear that?” - Cassidy said with an enthusiastic smile - “It’s the anthem of the nerd!”

Even though Leon couldn’t think straight from the pain, he mustered the courage to say:

“P-P-P-Please, don’t rip my underwear!”

He suddenly felt his feet touch the ground again. However, Cassidy was still holding the wedgie high. He instinctively spread his legs out.

“Why would I do that?”

“Please, I’m begging you!”

Leon felt his feet leave the ground once again, and a new wave of pain burned its way between his butt cheeks and on the sides of his groin where the elastic bands were as tight as ever:

“Give me three reasons why I shouldn’t rip these undies to kingdom come?”

The pain was making it hard to think straight. But Leon saw a light at the end of the tunnel. He realized that it didn’t matter what Cassidy thought of him - he was already used to being humiliated by her. All that mattered now was that he had a chance to save his briefs. Blushing a deep cherry red, he said:

“W-W-W-Well, first b-b-b-because I’ve been really good and I’ve held my position! Even during the bouncing wedgie! Also, I’m running out of underwear, and my mom is going to ask me why. And, also…”

Leon felt his face burning from embarrassment, tears welling up in his eyes. He didn’t know what to say, all he could think about was the pain burning between his cheeks as his feet were dangling more than an inch off the ground. The tighty whities gave out another pop and the toes on his left foot briefly touched to ground, before Cassidy readjusted her grip and lifted him up again.

“Also, because it really, really hurts and I’m going to cry! So, please, let me go!” - Leon hung his head in defeat and closed his eyes. If he was going to cry, at least it was going to be with his eyes closed.

Suddenly, his feet dropped to the ground. Cassidy still held white briefs high, gripping them by the leg holes, which were now up to his shoulder blades. He spread his legs beyond his shoulder width again, making sure his position was correct.

Cass rolled her eyes and said:

“You really are pathetic! You’re such a nerd that you can suck the fun out of anything.” - She sighed.

“But you know what? I’m feeling gracious today, so I’m not gonna rip your precious widdle tighty whities. But you better not pick that wedgie until I’m out of here!”

Just to drive her point home, she gave the white briefs a sharp tug. Leon gasped at the sudden pain.

“In fact, I want you to stay in that position for ten minutes after I leave!” - she looked to the side, trying to do the math in her head. She quickly gave up:

“How many seconds is that?”

Breathing quickly to alleviate the excruciating pain, Leon said:

“That would be six hundred seconds!”

“Ok, yeah! Count to six hundred! And don’t you even THINK about touching those tighty whities! Now, what do we say, nerd?” - she said as she gave the briefs some slack.

He blushed once again:

“Thank you, Cassidy!”

She gave them a sharp tug.

“OOOOUCH!”

“Thank you for what?” - she said, giving her best impression of an Elementary School teacher.

Gritting his teeth from the intense pain, Leon said:

“Thank you for the wedgie!”

“And…” - she cooed

“And for not ripping my tighty whities! I’m a nerd! I will always be a nerd and I will never be as cool as you!”

“Good nerd!” - she said, like a proud dog owner about to give her puppy a treat.

And with that, Cassidy finally let go of Leon’s underwear. He felt the waistband snap to his back.

“Now start counting.” - she coldly, as he went to pick up the homework folder he’d given her.

Leon began the long process of counting to six hundred, bent over, with his hands pressed against the tree, and his butt sticking out. His tighty whities were stretched above his waist, covering his back like a parachute.

Just as he was getting to 98, he heard Cassidy making her way to face him. She put her index finger in front of his lips, and he stopped counting. He looked into her cold, green eyes.

“And one more thing - tell your mom to buy you some stronger undies. I wanna hang you up next week.” - she said with a grin, and she made her way out of the clearing.

“Start counting again! From one!”

***