Pick Me! ~Choose Your Wedgie Boy~ (Chapter 1)

R-1D

"N-Naru wants to try it on his own, [Reader]!"

"Alright. Well then, just follow my directions, Naru."

"Y-Yes...gh...[Reader]." Narutaro winces.

"All you have to do, is bounce yourself. Pull your body up and try to fall back down as hard as you can. Can you do it, Naru?"

"N-Naru will try his best!" The ever eager wedgie boy says.

After taking a quick second to pause, Narutaro lifts himself up and quickly plunges himself downwards.

"Hmm~!" Narutaro whines as his face contorts from the pain, biting his lips with his eyes closed. His tighty whities filled the deeper crevices of his hole, started to turn into a thinner string, and pressed harder against his balls that popped out his briefs.

"Di-Did Naru do it right, [Reader]...?"
The wedgie boy asked as he slowly opened his eyes to look at you.

"Good job, Naru. Just keep bouncing yourself."

Narutaro smiled, although a hint of pain still remained on his face as he still remained in his cheek splitting hanging wedgie.

After another quick pause, Narutaro bounced himself again.

"Hnngh~! N-Naru's butt... Haah...!" The boy whines as his tighty whities gave his taint a rug burn once again.

The hot view of the nerd bouncing himself in his hanging wedgie went on for another few bounces, until you realized that at this pace, you and Naru would be here for way longer than you needed to.

"Hey Naru,"

"Ngh– Wha-what is it, [Reader]...? Mmm— Oww~!" The wedgie boy said in between two more bounces.

"You should try bouncing yourself faster. You'll get down from your hanging wedgie quicker that way and it'll make it feel better."

"O-Okay! Na-Naru will go faster!" The submissive nerd says, looking to feel a greater pleasure from a more intense wedgie.

Narutaro then proceeded to bounce himself by his tighty whities quicker. With each bounce brings with it the sounds of Narutaro's moans and the tearing of his undies's seams. Each bounce brought more pleasure to the wedgie boy, evident by the growing wet stain on the front of his briefs and the outline of his erect cock. The strain of Narutaro bouncing himself on his whities makes a hole start to form on the the undies. Each bounce makes the hole rapidly grow more and more until...

RIIIPPPPP!

"Uwah~!" Narutaro falls from his hanging wedgie, but luckily, you were able to catch him.

"Haah... Haah... Th-Thank you, [Reader].." He says with an o-face. You look at his lower half and you see his bare cock dripping with cum, the floor being stained with the seminal fluid. You also see a ripped fragment of his tighty whities still stuck within the crevices of his abused ass.

"Aww~ You look like a cute rabbit with that cotton tail of yours." You jokingly tease.

"Here, I'll pick your wedgie for you." You say as you slowly slide the piece of ripped underwear out of Narutaro's butt and toss it into the trash.

"Tha..Thank you."

"You've been naughty, Naru~ Cumming so much from a wedgie~"

"Naru is... naughty?" He says with a dazed look as he falls to the floor with his legs crossed in a w shape. He must be tired from all the excitement from his wedgie lesson and the cumming from said wedgie lesson.

"But~ You took your wedgies so well today like a good boy, Naru." You say as you ruffle the boy's pastel pink hair, like a light noogie. The cute boy giggles happily.

"—Now let's get you and this place cleaned up. Oh, and you should probably put on a new pair of undies. I can see your little weewee from here~"

Narutaro's eyes widen as he looks down and sees his exposed penis. His face turns as red as cherries and he covers his privates with both his hands.

"O-Okay, [Reader]! Na-Naru will change!" He said, flustered.

"And.. Naru will help you clean! It was Naru's fault for... um... cumming everywhere... Th-Thank you for the wedgies today, [Reader]!"

"Don't worry about it, Naru. Here's your pants." You toss the Narutaro's undone pants to him, and he manages to catch it.

Narutaro changes into a fresh pair of undies and slips his pants back on. Then, the both of you cleaned up the room, wiping the floor of Narutaro's cum and taking Narutaro's ripped tighty whities out of the coat rack and into the trash.

"Hey Naru..." You say as you dispose of the ripped tighty whities.

"Hm? What is it, [Reader]?"

"Why don't we go underwear shopping next time? Y'know, cause I ripped your tighty whities and all. Plus, you could really go for stretchier undies. And don't worry. I'll pay for the replacements."

"B-But Naru couldn't possibly let you pay for his new undies!"

"Come on, let me do this for you."

"Are you really okay with that, [Reader]...?"

"Obviously. I'm the one who offered."

"Okay, [Reader]. Thank you so much."

"No problem. I'll just contact you on Lietzenger again the next time I'm free, okay Naru?"

"Mhm!" The boy nods in response.

"Well, it's getting late. See ya next time, Naru."

"Bye, [Reader]! Let's do this again sometime! And... I hope you can teach me more about wedgies!"

"I won't back out of the promise. I'll make sure you'll have a fun time for our next sessions~"

You end the night leaving Narutaro's home, making one more promise to the boy.
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MetaNotes:
+15 Narutaro_Dominance
+15 Narutaro_Trust