"A-Amami-kun...?" Shuuichi stammered out. He was just innocently searching through the library, hoping to find a book he could take back to his room when Rantarou had crept up behind the unsuspecting detective and pulled on his grey trunks. It wasn't a rough tug, but it would certainly be felt.
"Sorry about this, Saihara-kun. I lost a bet with Ouma-kun, and he told me to give you a wedgie as punishment, though I suppose it's more of a punishment for you, right?" Rantarou smiled sheepishly, tugging a tiny bit more on Shuuichi's underwear. He seemed reluctant to really try to give Shuuichi a proper wedgie, the detective noticed. It was odd, after being subjected to so many brutal ones from Kokichi, or the playful but still rough ones he'd occasionally get from Kaito. Or even the excruciating one Gonta gave him after Kokichi tricked Gonta into wedgieing the poor detective. "Ah...I really shouldn't be doing this...I suppose this is what happens when you make a bet with Ouma-kun without thinking..."
"I-it's fine, I get it. I just seem to be Ouma-kun's favourite target, so it's not your fault." Shuuichi shifted his position causing the underwear that was bunched up in his butt to shift with him. Rantarou raised his eyebrow.
"You are, aren't you?" Rantarou mulled over that fact. "In fact, whenever a guy in our class gets wedgied it almost always seems to be you..."
"Th-that's mostly because of Ouma-ku- ugh?!" Shuuichi let out a grunt as Rantarou pulled on the trunks again, with a little more power than before. "A-Amami-kun?" The detective looked back to see Rantarou gazing at Shuuichi with an intense focus, as if trying to read him completely.
"If I think about it, you being such a common target might not be an accident. Or completely due to Ouma-kun." He followed up his sentence with another rough tug, making Shuuichi go onto his tiptoes. "There are plenty of ways you could have avoided this one right now, actually. The library echos, and I wasn't being silent at all. You would have heard me walk up behind you."
"I w-wasn't paying attention..." Shuuichi's face burned slightly. He looked at the floor so Rantarou wouldn't notice.
"Not just that. Even your outfit...for someone who wears a belt, they sit rather low on you, and your waistband was a bit above your pants. If you ever bent over, everyone would see your underwear." Rantarou pulled again, now bringing the legbands of the grey trunks into view. "You're a rather tidy person, Shuuichi. I can't imagine that outfit being an accident."
Rantarou's hands moved to the legbands and yanked the trunks up into a T shape. But it wasn't playful or sadistic, it felt more methodical, as if Shuuichi were his test subject and he continued to force the trunks deeper into Shuuichi's body, the pressure around his crotch growing and the strip of fabric between his cheeks tightening and rubbing harshly.
"Ouma-kun wouldn't target you all the time without a real reason..."
"Wh-what do you mean?" Shuuichi could feel his feet about to leave the ground and Rantarou continue the up and down motion, stretching the trunks further up his back.
"Even when you stand upright, your hands go to your hips, and you tuck your thumbs under the back of your jacket and it'll raise slightly, so you almost always have your underwear exposed, which is like begging for situations like to occur. The only time I don't see you do it is when you don't know someone is there...and I've seen plenty of times where you should have felt Ouma-kun's hands before he gave you a wedgie..."
Shuuichi's face was beet red at this point, his hands pushing down on the front of his pants and underwear. He knew where Rantarou was going with this, but...
"Tell me, Saihara-kun" -Rantarou used his strength to lift Shuuichi into the air by the legbands, leaving the detective to wail into the almost empty library. Rantarou smiled his question- "Are you...into getting wedgied?"
"H-huh?!" Shuuichi spluttered out, his legs twisted in from the pain of the fabric chafing against his dangling body. The reluctant wedgier had transformed into some kind of analytical giver.
"It would make sense, right? Why you're always in a position that would make it easy for you to wedgie. Why Ouma-kun always wedgies you. Why these situations only happen when you know somebody else is around...you actually like it when someone wedgies you, right?"
Shuuichi attempted to answer, but all he could think about was the feeling of the hanging wedgie he was getting off someone usually so laid back.
"Ouma-kun probably wanted to see if I'd figure it out. That's why he made this my punishment for losing the bet. It was more for your own humiliation...you probably know that Ouma-kun knows, but you don't ever object to the wedgies. Not to mention you're best friends with Momota-kun who would do it as a friendly prank, so that's even more reason to keep doing what you do. Though you got too careless..."
Rantarou lowers Shuuichi to the ground and retakes the waistband of the trunks and pulls again. Shuuichi's back arched as Rantarou forced the trunks half-way up Shuuichi's back. Rantarou leaned into Shuuichi and whispered "Tell me if I'm right, Saihara-kun..."
Shuuichi's face was completely flared up, his legs and hands were trembling. "Y...yes. Y...you're right..." He admitted timidly. "E-everything was right..."
"Ah, so I was right..." Rantarou let go, and Shuuichi fell to the ground with his bunched up underwear pooling out from his pants. "...sorry, I got a little carried away, but when I get a theory I need to see if it's true." He rubbed the back of his head.
"I...d-don't mind." Shuuichi replied, standing up slowly, he turned to Rantarou but didn't look at him.
"No, I suppose you wouldn't have. Don't worry, I won't tell anyone...you have your thing, so...you do you. But...I don't think you can really expect wedgies from me. Not unless I end up falling for another one of Ouma-kun's bets, anyway...heh."
"R...right..." Shuuichi felt so ashamed in this moment. He never expected for Rantarou to out him on wedgies. It was a set up from Kokichi, but that doesn't make it any less humiliating for him.
"I feel bad." Rantarou admitted with a frown, contemplating what to do. "...alright then, how about this? I'll give you a free pass to give me a wedgie sometime. Private or public, you pick."
"Wh-what?" Shuuichi looked up at Rantarou in surprise. "D-don't I weird you out though..?"
"There are plenty of masochists out there, Saihara-kun. Ones that do way weirder things than you. Just...let's not do the wedgie today, okay? I've got my favourite underwear on, so I'd prefer not to have 'em stretched out."
"A...are you sure?"
"Sure. I mean, I'm certainly not a fan of wedgies, but if it'll make things up to you then I think I can endure at least one."
Shuuichi paused for a few moments, "A...alright then. I'll let you know..."
"Cool." Rantarou smiled. "Oh, and just in case you wanted to know, Ouma-kun is in the game room right now. Momota-kun went to his room. Y'know...for reference in case I'm not good enough for you."
Shuuichi smiled weakly as Rantarou walked off, he pushed his underwear back into his pants as best as he could. Rantarou probably knew that what he did worked fine.