Wedgie Tax: Part 2

“421, 422, 423…”

Leon continued counting. His legs were shaking from having to hold his position for close to ten minutes now, and he had a long way to go still. The sharp pain between his cheeks had gradually turned into a dull ache that was now pulsing inside of his butt.

No matter how many times Cass wedgied him, he was always astonished at the amount of pain and humiliation she was able to extract over him by using his most intimate article of clothing.

From time to time, he entertained the idea of breaking position and picking out his monstrous wedgie. Cassidy was definitely gone by now. But he didn’t have the courage. What if she was hiding somewhere, lurking in the bushes, waiting for him to slip up?

She had gotten in Leon’s head so much that even when he was home he felt like she was watching him. Every time he put on a pair of white briefs, he felt like Cass is about to pounce.

“501, 502, 503…”

Leon’s legs were aching. He had a hard time keeping them straight for such a long stretch of time, but the wedgie position demanded it.

The boy tried to shift his focus. His butt was getting sorer by the second. He could feel the back of his tighty whities painfully digging into his butt, narrowed to the width of a thong. But it almost felt like material was expanding, pushing his cheeks apart. Meanwhile, the elastic borders on the front were so tight that they were cutting into the sides of his groin, right on the most sensitive part where his thighs met his crotch. He felt a constant squeezing pressure inside his balls, like he was wearing a pair of briefs that were several sizes too small.

Once again, he tried his best to focus on something else. He didn’t want to focus on his aching legs, and he also didn’t want to think about the pain inside his butt and crotch. Suddenly, he felt a lump in his throat. He’d been feeling it for a while now, but he hadn’t been quite able to put his finger on it. But now the feeling was clear - it felt like cotton. He’d spent such a long time in this wedgie, that he was beginning to taste his own underwear!

“598, 599, 600!” - he said in a loud voice, relieved that his torment was finally over.

Triumphant, Leon collapsed to his knees and rested his head on the tree. His aching legs became ten pounds lighter as he breathed a sigh of relief.

Almost as soon as he collapsed to the ground, Leon undid his jeans and pulled them down to below his butt so that he could pick his massive wedgie.

From experience, the boy knew it was best to go slow with these things. First, he carefully readjusted the white briefs in the front. He immediately felt the pressure on his crotch subside, although it didn’t disappear completely. Because there was still the problem of his actual wedgie.

Leon took in a deep breath and turned his head to inspect the damage. His once snug and comfortable tighty whities were draped limply over his waist, stretched out to the point of almost being unrecognizable. Of course, the part wedgied up his butt was tighter than it was ever meant to be.

The boy sighed as he took the elastic borders of his leg holes and started pulling them out of his butt. He did it slowly and gently, without any sudden movements.

“Aaaahhhh….” - Leon groaned as he peeled off the final bit of the wedgie.

As he pulled the undies out, he felt a gap inside his butt. Over the last ten minutes, his cheeks had become so used to being spread apart that for a moment Leon thought if they would ever come close to each other again.

That’s what ten minutes of having your underwear up your bottom does to you - your body gets so used to the pain and discomfort that its sudden absence feels weird.

Leon readjusted the tighty whities, which were now much looser than they were before, almost sagging off of his hips. The only thing he hated more than wedgies was having saggy briefs. So, to remedy that feeling, he hiked the undies up his hips, until they were sitting somewhat comfortably again. Which wasn’t saying much, given how stretched out they were.

Their back was soggy with sweat from the wedgie - for the last ten minutes they had been bunched up inside his butt and the sweat from all the stress and embarrassment had left them soggy. Instead of keeping him warm, they were now ice cold on this chilly spring day.

He quickly buttoned up his jeans, picked up his backpack and started making his way home, doing his best to forget what had just happened here.

This, of course, was basically impossible. As he walked, he was constantly reminded of the pain in his butt. The skin on the sides of his crotch was also sore, and when he looked to inspect the damage, he could see the skid marks left by the elastic borders of his leg holes.

He began to waddle. That way his thighs didn’t rub against his aching package, and his cheeks didn't rub the sore spot inside his butt. The only thing that kept Leon going was the thought of the aloe vera he was going to rub on all the sore spots when he got home.

***

The sight of his house was definitely a welcome one. He immediately went to his room. He just wanted to have a nice, cold shower and get this day over with.

“Hey, Leon! How was school today?” - he heard his Mom say in a cheery voice, as she entered the room and gave him a warm hug.

Heather was 39, with the kind of toned physique you'd expect from a yoga instructor. Because of all the private lessons she gave, she was constantly not home. As a single mom, she had to work a lot to take care of everything. Leon noticed she held a shopping bag in her hands.

“Hey, Mom. It was Ok.” - he replied

“Have you finally solved the mystery of why all your underwear keeps disappearing?”

Leon tensed up.

“Or are you finally going to confess that you’re actually eating them?” - she laughed

Leon blushed. In a sense, she was right - except it wasn’t his mouth that was eating them…

“But don’t worry! I just got back from my shopping trip, and I’ve got you some new undies!” - she said in an excited voice. - “I wanted to show you!”

Heather dumped the shopping bag on his bed. Leon felt a pit in his stomach as he saw a flowing river of white. As he scanned the contents, he saw that they were all tighty whities.

“Mooom! I told you I wanted you to get me boxers!” - Leon pouted.

“Honey, we’ve talked about this!” - Heather said in a patient voice. - “I always want the best for you, and briefs are much better than boxers!”

Leon rolled his eyes. He’d heard this spiel a hundred times already. But there was no stopping her once she got started:

“You’re an active young man, and briefs give you a better fit and better support for your manly bits! They’re also better at absorbing moisture, and we both know how sweaty you can get down there!” - she smiled as she pointed to his crotch.

Leon blushed:

“But why do they have to be white? That’s such a nerdy color!” - he said with displeasure

“Nerdy?! White is practical! It looks good on you, and it lets you know when you need to change your undies! It’s also the color of calmness and purity! Did you know that white actually has healing properties? I’ve been reading this book by…”

“Healing properties? Yeah, tell that to my butt!” - Leon thought as he started zoning out. He always got annoyed when she talked about that yoga mumbo-jumbo.

His gaze drifted to the underwear strewn over the bed. They were all different kinds of white briefs. Most of them were in packs of three or four. There was the traditional design with a thick waistband and a double-layered front pouch for extra support. He winced as he saw the thick elastic borders around the leg holes. A wedgie in these would hurt a lot. And that waistband was probably really strong. He could almost picture Cass pulling these up his butt.

Another pack held four white briefs with a flyless, high-cut design. The material looked thin and breathable. The waistband had a thin red line in the middle, and the seams on the front were also red. He’d be sad to see these go. He knew from experience how fast thinner cotton tears.

As his gaze drifted along the different pairs, he suddenly felt a pit in his stomach. He was utterly horrified as his eyes were glued to a particular pack of tighty whities.

The pack in question held two pairs of flyless white briefs with no seams at the front. What horrified Leon was the fact that both the waistband and the elastic borders on the leg holes were a gentle, pale pink.

“Mom, wh-wh-why are these pink?!” - he said as he pointed to the pack with a trembling hand.

“They’re not pink, they’re white!” - Heather corrected him. - “Oh, you mean the waistband? Well, it was the only color they had left. They’re made of bamboo and I really wanted you to try them!”

She got more excited:

“I know how much you like cotton, but bamboo is much more sustainable! It’s also much more breathable and it’s very comfy! I tried some bamboo bamboo panties a week ago, and I’m never going back to cotton!”

“Yeah, b-b-but why pink?”

“It’s all they had left! But why does it matter? What’s wrong with pink?” - Heather said, genuinely confused.

“Because pink is a girls’ color!” - Leon was absolutely mortified. Was she really that oblivious?!

“Nonsense! Did you know that in Medieval times, they used to wrap girl babies in blue and boy babies in pink? That’s because pink was considered the softer version of red. And red is the manliest color! It means strength, it means passion, it means royalty! And besides, color is universal. There’s no such thing as a male or female color!”

“I need to take a shower.” - Leon said, furious. His Mom was hopeless.

“Try them on after you’re finished! Believe me, you’ll love them!” - Heather said as she exited his room. She shook her head.

“Teenagers!” - she said under her breath.

Leon took off his shirt, and unbuttoned his jeans. As he took them off, his saggy briefs dropped along with them. He took a good look at them. After some hesitation, he threw them in the bin, and got in the shower.

The cold water helped clear his head. It also alleviated some of the soreness, especially on the sides of his crotch. His butt still needed some care, though. He wrapped a towel around his waist and got back to his room.

He opened the top drawer on his night stand and took out a tub of aloe vera. One of the perks of your Mom being a yoga instructor was having all sorts of balms, ointments and oils lying around the house.

He cleared out his bed and got on all fours. He dabbed some of the cream on his fingers and started applying it to his sore butt crack. A soothing coolness spread inside his butt as he sighed in relief.

After about five minutes, Leon felt much better. As he stood up from the bed he stepped on something plastic. It was the pack of pink-waistband tighty whities. He groaned.

“Well, I’m obviously never going to wear these in public. Wouldn’t hurt to try them on now…”

Leon took the briefs out of the packaging and held one of the pairs in his hand. He was immediately struck by how soft they were to the touch. He stepped into them and slowly pulled them up his legs.

His eyes bulged in shock. These briefs were the softest thing he had ever worn in his entire life! It was like he was wearing a cloud. Most importantly, the elastic borders were extremely soft.

Against his better judgment, he grabbed the waistband above his butt, and gave it a sharp pull. The briefs bunched up inside his butt crack, but he only felt a slight discomfort. The tighty whities were already up to his mid back. If these were the cotton briefs he just threw away, he would already be in massive pain.

He picked the wedgie out of his butt. Maybe these tighty whities weren’t as bad as he initially thought…