Wedgie Tax: Part 3 (F/M Hanging Wedgie)

Leon was putting the finishing touches on his campaign. He had just discovered Rapiers of Righteousness, and it was so much better than D&D! It eschewed the chaos of the D20 system, and put roleplaying over strategy. Yes, the rules were a bit dense, but it was worth it!

Or, at least that’s what he thought. Even though he had an entire bookshelf of TTRPG books and supplements, he never had anyone to actually play them with…

The nerd was taken out of his reverie when he heard his alarm go off. He was going to be late for school! He quickly put on a T-shirt and some shorts, packed his things - including the homework for Cassidy, and dashed out of his room.

But as he was running, Leon had a nagging sense that he was forgetting something…

***

Leon became tense as he once again made his way through Mulberry Park. Every Friday he had the feeling that school ended at least twice as fast as usual. Existential dread tends to do that to you. He quickly made his way to that all-too-familiar oak tree.

Cassidy still wasn’t here. He reached into his backpack, took out the folder with her homework, and set it on the ground. But even as he did that, he still couldn’t shake the feeling that he had forgotten about something important.

“Hey, Lose-on!” - Cassidy shouted.

Leon jumped, his heart skipping a beat.

“Oh, did I startle you?” - she feigned surprise. She was wearing a black sports bra and a pair of black yoga pants, her well-toned muscles on show.

“J-J-Just a little. Y-Y-Your homework..”

“Yeah, yeah, I saw it. You know the drill.” - Cass said as she drew a circle in the air with her index finger - “Assume the position!”

Leon complied, laying his hands against the sturdy tree, spreading his legs, and sticking his butt out.

“So obedient! I might even go easy on you this time!” - the bully said, lying through her teeth.

The nerd felt her cold fingers reach into his shorts, grab a hold of his waistband and slowly pull it out. Which tighty whities was he wearing today?

His heart sank. He just remembered what it was he had forgotten about, as the quiet clearing was pierced by Cassidy’s shrill laughter:
“Hahahaha! You can’t be serious! Are these pink?! Are you wearing pink tighty whities?”

She pulled on the briefs some more. Not hard enough to hurt, but enough to start wedging them in his butt.

“Even the leg holes are pink! This is too funny! Even for a nerd like you!”

“There’s more white than there is pink, you know…” - Leon mumbled defensively, a deep blush across his cheeks.

“Legs together!” - Cassidy’s cold voice sent shivers down his spine

Leon quickly put his legs closer together, and used the opportunity to clench his cheeks.

The hapless nerd suddenly felt a breeze on his legs as Cass pulled his shorts down to his ankles. He gasped.

“There! That’s so much better! I almost feel sorry for what I’m gonna do to them…” - the bully said in an increasingly malicious voice.

She grabbed Leon’s briefs again and sharply yanked them up. He squealed as he felt the material invade his butt, despite his clenched cheeks. He realized that he’d never had a wedgie in bamboo undies before.

Although the underwear reached his mid-back, Leon felt only a mild sting. Maybe this wasn’t going to be that bad, after all?

“These are stretchy! I like ‘em!” - Cassidy said as she switched to an underhand grip on the pink leg holes.

Now he was definitely feeling the burn as the once soft elastic leg holes of the tighty whities began cutting into his butt. Clenching his cheeks had done little to stop the material from entering deeper inside of him.

Suddenly, Leon felt Cass give the underwear a little slack. He clenched his butt in preparation.

“Liftoff in 3… 2…” - she yanked on the briefs with all her might, lifting the boy off the ground.

He let out a high-pitched whimper as he felt the pink leg holes dig deeper into his butt and groin.

“You know what? I got a better idea!” - Cassidy said with sadistic enthusiasm, as she let the tighty whities go and let them snap to Leon’s back.

He gulped. Maintaining his position, he felt the girl grab onto his thighs and lift him up, leaving his shorts in a heap on the ground. To keep his balance, he put his hands on her strong shoulders.

“No, Cass, please! Don’t! Not a hanging wedgie! Please!!!” - Leon begged.

But his pleas fell on deaf ears, as he felt Cassidy fiddling with his undies. Suddenly, she let go of his legs.

The boy felt his stomach jump as he dropped. His mind screamed in panic as his hands instinctively braced for impact, until his entire body jerked to a halt. His body stopped in midair, a pain erupting against his stomach and sides.

He bounced for a second, and then his underwear went rigid. As his body quickly settled, he felt incredible flashes of pain across his entire butt and crotch.

Dangling by his tighty whities, Leon felt the full force of the hanging wedgie as his body weight drove him deeper and deeper into his white and pink harness of agony.

His once soft and comfortable undies were now slicing into him in excruciating ways, turned into a cruel torture device.

He felt a searing pain as the briefs stretched down from his tailbone, cutting deep between his cheeks, painfully grinding his sensitive anus and perineum, before they finally became unbearably tight around his package. The pink leg holes had painfully dug into the sensitive sides of his crotch, leaving a searing burn through inch of flesh they touched.

Trying to find some kind of relief, Leon tried to shift his weight to the front. He winced as he let out a pathetic whimper. While the pain on his butt and tailbone lessened, the pressure on his crotch and stomach dramatically increased. The leg holes cut into his groin even more cruelly than before, and the pressure in his balls sent a shockwave of pain to his head, screaming:

‘This hurts! This hurts! Please, make it stop!’

Unable to take it anymore, he straightened up. This alleviated the wedgie in the front, but it ignited a new fire in his butt as the tighty whities sliced into him with renewed vigor. Leon whimpered. He just couldn’t win.

Up above, he saw the massively stretched out line of white, rimmed with pale pink. Cassidy had expertly attached the pale pink leg holes to the thick branch. There were no signs of tearing. While his entire being was engulfed in pain, tinged with humiliation, a small part of him was relieved. He really didn’t want to see these tighty whities rip. They were so comfortable! Or at least they used to be. Before they were so viciously rammed up his butt…

Meanwhile, Cassidy was enjoying the show, her arms crossed in front of her chest and a wide grin of satisfaction at a job well done.

“Your panties are so cute, all stretched out like that!”

Grunting in pain, Leon mumbled:

“They’re not panties! They’re briefs!”

“Are they? Because they look more like a thong from here!” - the girl giggled. Suddenly, there was a glint in her eye. Leon knew that look. It was like a light bulb came on inside her head as she got a bright idea. He gulped because he knew it meant trouble.

“Actually, you know what? Why don’t you start wearing actual panties?”

Leon felt mortified.

“Wh-Wh-Wh-What?!”

“Yeah! You’re already halfway there with those pink tighty whities!” - Cassidy grinned, pointing to the nerd’s stretched out briefs. - “Besides, you’re already my bitch, might as well start dressing like it.”

Scrambling for a way to get out of the humiliating prospect, Leon pleaded:

“C-C-Cassidy, please! My allowance isn’t enough for me to buy panties!”

The bully laughed:

“Boy, you really are pathetic, aren’t you, Lose-on?”

Cassidy reached one of the pockets of her yoga pants, fished out a couple of bills and tossed them on Leon’s shorts, which were still standing in a heap on the ground.

“Here, and make sure they’re cute! So, no granny panties! Got it?”

“Yes, Cassidy...” - Leon said in a defeated tone, his head hung low.

He suddenly felt her hands grab his feet as she yanked down on his legs, pulling him deeper into the wedgie.

“Aaaaahhhh!!!” - he squealed

“What do we say after someone does something nice for us?” - she cooed.

“Aaahh! Thank you, Cassidy! Thank you so much!” - Leon screamed through the fits of unbearable pain.

“Such good manners! You’ll be a well-behaved little girl in no time!” - his tormentor giggled, suddenly letting his legs go. The poor boy winced as he bounced inside his white harness, the pink leg holes of the tighty whities grinding painfully into his butt and groin.

“And next week, you’ll be getting three wedgies instead of one! Girl’s gotta get her money’s worth!” - she said as she wrapped her hands around his ankles again. - “Now, what do we say?”

The boy bit his lip, tears welling up in his eyes:

“Can we please not do this?”

She sharply tugged down on his legs, sending a fresh sting of pain burning across his butt and crotch, as his balls got painfully scrunched up.

“AIIIIIIIIEEEEE!!! Thank you for the wedgie, Cassidy! Thank you for putting me in my place! I’m a nerd, and I will be a nerd for as long as I live!” - he shouted in a high-pitched voice, screaming in pain, as tears started falling down his cheeks and fogging up his glasses.

“And don’t you forget it!”- Cassidy said as she let go of his legs and started to make her way out of the clearing. Leon didn’t even entertain the idea that she would help him down from his predicament. He just hoped that he would stop bouncing soon.

As he watched Cass walk away, she chuckled:
“With you wearing panties, I just hope I don’t lose track of which loser I’m wedgieing - you or my sister…”

Leon breathed a sigh of relief. At least she was gone. The nerd felt a cold breeze against his legs as he settled into his hanging wedgie. He sighed. He was going to be here for a while. He slightly spread out his legs so that his thighs weren’t adding to the pressure on his package. He winced as the leg holes sliced even deeper into his groin, occupying the tiny space freed up by moving his thighs. On the bright side, that did take a little pressure off of crotch.

He relaxed his stomach. The pink waistband was still cutting into him, but once he was no longer fighting against it, it hurt just a little bit less. That gave him an idea!

In all the hanging wedgies he’d gotten from Cass, Leon could never figure out what to do with his butt. His instinct was to clench it as much as he could - first his butt cheeks, then the inside of his butt. Of course, that never really helped him. But it was the only way he could keep at least some shred of his dignity. A bastion of un-wedgied flesh.

He winced once more as he felt the briefs kept digging into him.

But what if he didn’t fight it? What if he accepted the fact that he was a nerd? What if he embraced the wedgie?

Going against his base reflexes, he willed his butt cheeks to relax. Clenched around the tight white and pink fabric, his cheeks gradually became softer. Leon gave out a high-pitched whimper as even more of the bamboo tighty whities invaded him, exploring the deepest recesses of his butt, and leaving a slicing pain everywhere they passed. But just like with the front, this allowed the wedgie to settle. And while it felt like he was being split in half, at least it was something he could conceivably imagine living with.

Consigned to his underwear prison, with his pants on the ground below him, and his legs swaying in the wind, he realized how pathetic he must look right now. But for the first time, he was hopeful. He knew that once this torture was over, he could get back to planning his Rapiers of Righteousness campaign, rewatching Xena: Warrior Princess, and just generally live his life.

His undies didn’t define him. This wedgie didn’t define him. Sure, it hurt. It hurt a lot! He was definitely not going to be able to sit down for at least a couple of days. And it was definitely humiliating and emasculating. But sooner or later, his undies were going to rip, and this whole ordeal was going to be over.

Yes, he was a nerd. He was always going to be a nerd. And that was okay!

Leon winced. Now there was only the matter of waiting for these tighty whities to rip. And by the look of things, it was going to take quite a while…

***