Mondo's and Ishimaru's Wedgie Bonding

“Bro, are you sure about this?! Such a thing…I give out detentions for such things and you wish me to give you one?!” Ishimaru exclaimed. It wasn’t odd for him to be called into Mondo Oowada’s room, but the request for the two to wedgie each other was a surprise.

“I saw it on the internet that it’s supposed to some sort of bro-bonding shit-“ Ishimaru gave him a look when he swore “-says that you grow closer because you trust them to give you a wedgie. Told Momota about it and apparently, he’s gonna do it too. Just gotta rip each other’s underwear off.”

“I am still unsure…but if you are sure of this, then I will agree to it, though it will be difficult since it is against my moral compass!” Ishimaru nodded.

“Then why don’t I wedgie you first?” Mondo suggested. Ishimaru paused before sighing and turning his back to the biker. “I’ll make it quick, don’t worry bro.” Mondo gripped the white waistband with one hand, and place the other hand on Ishimaru’s shoulder. He slowly began to ease the waistband up causing Ishimaru to take a sharp breath from the slow increase of pressure to his crotch.

The legbands began to emerge from Ishimaru’s pants as the briefs were stretched up his back. The underwear creaked slightly but Mondo quickly realised that they were never gonna rip if he went at this rate. He silently apologised to Ishimaru before gripping the legbands with both hands and jerking them up roughly. Ishimaru let out a cry as his feet momentarily left the floor. His legs shook when he hit the floor again and he fell towards the bed, using his hands to stop him from falling completely. Though this action caused him to fall deeper into the already intense wedgie which led to Ishimaru’s eyes watering up.

“Shit!” Mondo growled when he pulled Ishimaru back up on instinct which just led to another yelp. “F-fuck!” He looked down at the hall monitor who let out a low groan as he stood back up. “You wanna keep going…?”

“Y-yes…” Ishimaru managed. “I can get through this…” Mondo hesitated but hauled the briefs up again, forcing Ishimaru onto his toes. His thighs went together as the white strip that attacked his butt went rigid and the crushing pressure on his front increased. As Mondo continued to stretch the underwear out to make it easier to rip, Ishimaru let out a series of ‘ack’s, ‘urk’s, and ‘gyah’s with each yank to his once comfortable briefs.

Mondo cursed slightly at how durable these briefs were jerking them up again. By this point they had managed to reach the upper parts of Ishimaru’s back. The victim was trying to take away some of the pressure by pushing the front of his underwear down though it didn’t help the legbands grating against the sensitive areas of his body. He couldn’t help it when a few tears began to trail down his face.

The seams began to pop and there were tiny holes near the waistband and legbands. Mondo smirked at this sight and tightened his grip. “Alright, I’m just gonna go for the full rip. You ready?” Ishimaru nodded slightly. Mondo crouched then jumped up, throwing his arms up with him. The seams popped further and some holes grew in size though the briefs remained on Ishimaru’s body, so it only caused Ishimaru to be dragged brutally into the air by the tighty-whities.

Ishimaru cried out and held his hands tightly over his crotch. “Just one more, this time for sure!” Mondo said taking the same position and imitating his previous action, this time the legbands broke apart and the underside of the underwear ripped completely. Ishimaru let out one final yelp at the momentary pain before they ripped. The remnants sat around Ishimaru’s waist pooling over his pants, the hall monitor carefully removed the pieces and threw them in the nearby bin. There was a horrible burning sensation left from the wedgie but he had at least managed to stop his tears.

“My turn then.” Mondo said, taking his jacket off and turning his back to Ishimaru. The hall monitor frowned, doing this was completely against what he stood for…but he was doing it because Mondo wanted to…did that make it okay? It was consensual. Mondo wanted him to do it. And he’d be lying if he’d never wondered by people always had fun targeting him with wedgies. Ishimaru took hold of the white waistband of Mondo’s orange underwear.

The hall monitor took a moment to process it all. The feeling of the fabric in his grasp, the anticipation of knowing what comes next. He took a breath and jerked the underwear up with more strength than intended. The appearance of the legbands was surprising, he didn’t think Mondo would have worn briefs too. Mondo let out a surprised grunt at the sudden sensation as the legbands rubbed against him. He was used to being on the giving end of wedgies so this was an unpleasant experience to say the least.

“W-was the too much?!”

“You just started. Hurry it up.” Mondo said. Ishimaru nodded and proceeded to jerk the underwear up again which prompted another grunt from Mondo. Ishimaru’s expression made it obvious he was overthinking on how to do this. Was there a certain way you were supposed to administer a wedgie? Was there a proper way to give someone a wedgie to prevent ripping the underwear? Then would Ishimaru need to do the opposite? He’d received so many over the years, you’d think he’d just know…

Using the experience from the past, Ishimaru grabbed the legbands and forced them up causing Mondo’s crotch and butt to be brutally assaulted by the orange briefs. Mondo tried to say something but he was completely dumbfounded how quickly Ishimaru had gotten into this. The sudden excruciating feeling of his briefs pushing his crotch flatter against his body and the rubbing, like rope, of his underwear against his but forced out a gagged noise from the back of his throat.

Mondo shoved his hands down the front of his pants and tried to force the briefs away from his pained groin. He used to give Takemichi wedgies frequently because he was the only member of the Crazy Diamonds who wore tighty-whities. Is this how it felt? Being sliced by your own undies?

He didn’t have much time to think as Ishimaru gave another vicious yank A seam or two on the waistband popped off. Another yank and the back of waistband separated from the orange fabric. Mondo let out a small sigh of relief before realising.

“Wait…I am supposed to rip the underwear off completely.” Ishimaru spoke moving his hands to grab the legbands and yanked them up into a single strip of fabric to resemble an orange and white thong. Mondo’s face reddened as the briefs continued to chafe and attack his sensitive parts with each new tug was another increase in pain to the point where he couldn’t even make a noise in response to the wedgie. Ishimaru, though, seemed too focused on what he was doing to notice it.

A few small tears pricked the eyes of the biker but he did his best to discretely wipe them away before Ishimaru could ever tell though with each agonizing pull the tears seemed to quickly be replaced.

Pop. Pop. Pop. With each tug was another pop of the seams around the legbands. Ishimaru gave a determined expression and crouched down and imitated Mondo’s actions when he has reach this point. One legband snapped off leaving one in working condition. Mondo let out a high-pitched yelp, his face completely flushing at this point. Though, once again, Ishimaru seemed to take no note of this.

Ishimaru took hold of the remaining legband with both hands and pulled with all his strength. Mondo let out a gagged groan and the lone legband shifted and twisted against his groin and his butt before the satisfying snap came. Ishimaru let go and let the remains of Mondo’s briefs curtain around his waist. The biker removed the bits and pieces of his orange briefs and shoved them in the bin, on top of Ishimaru’s white briefs.

“D-damn…” Mondo tried to prevent himself from stuttering, though it seemed to be in vain. “You really went for that.”

“It was for our relationship, bro! I will do whatever you need me to if it will help us grow closer!” Ishimaru smiled. “…though, that was perfectly good underwear gone. I do not wish to walk back to my room without underwear. Kuwata-kun has apparently been going on a pantsing spree.”

“Well…” Mondo walked over to his drawer and pulled out a pair of black briefs. “…it’s not exactly what you’d like, but I can give you these until you get back to your room.” Ishimaru took the briefs from Mondo and frowned. Mondo knew Ishimaru only wore tighty-whities, but he didn’t own any. He wasn’t a nerd.

“Very well. I will return these as soon as possible.” Ishimaru nodded and quickly went into the bathroom to put them on. He came back out and bowed to Mondo. “I will admit, it was rather fun.”

“Huh?”

“I do not agree with using it as a bullying technique but in a situation like this, I found it rather fun for us to exchange wedgies!” He placed his hands on his hips as if proud of the fact. “We should do it again, though it would probably require some underwear shopping. I can buy you some sensible white briefs! What a perfect opportunity!” Mondo blushed at the idea of going underwear shopping with Ishimaru but nodded anyway.

“Yes, farewell for now, bro!” Ishimaru bowed again before leaving the room.

Mondo sat on his bed and thought about what had just happened. Something about exchanging wedgies with Ishimaru was…exciting…? He gulped, suddenly realising. He locked the door to his room and began to undo his belt…