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

R-1B

"Follow me." You say, walking towards the desk. Narutaro, the submissive nerd, nods and does as you say. The spring in his step shows Narutaro's excitement for his wedgie lessons.

Before you stands the pink haired boy, in front of him is his desk.

With restrained force, you push Narutaro's back with the rest of his body towards the desk, trying not to hurt him too much. He grunts as his body hits the desk.

"Bend over for me, Naru." You order while caressing his back. Narutaro's
butt perks upwards and his breath becomes heavy with arousal.

You continue to caress his erogenous zones; his head, his nape, all the way to his waist- before pulling down his pants to reveal his tight white briefs hugging the figure of his ass which is already eating some of Narutaro's tighty whties, his balls, and his erect dick. Narutaro blushes as he feels his undies being exposed.

You grip the waistband of Narutaro's tighty whities.
"Are you ready for your wedgie, Naru?" You whisper into his ear.

"Y-Yes. Please wedgie me well, [Reader]."

You can't help but let out a chuckle at the dork's response. Without hesitation, you tug on the boy's white briefs, sending the cotton deep into his cheeks.

"Hngh~!" Narutaro groans, the wedgie making him stand on his tiptoes and clench his cheeks.

You yank on the wedgie boy's undies higher and harder. The petite boy's thin body is lifted off the ground, but the boy, gripping the desk, still remains bent over on the desk.

"You're taking your wedgie so well, dork." You say, slowly lowering him and his white briefs down, praising him, and stroking his head with one hand.

"[Reader]~♡" The pink haired, drooling boy who's lost in pleasure moans out your name. His cock twitches and oozes out a dribble of precum onto the wedgied undies as he's being praised.

"...I know how to make this feel better for you." You whispered again into Narutaro's ear, leaning against his body.

"Pl..Please tell me."

"All you have to do-" You say as you switch your grip from the white undies to the boy's thin wrist. You gently guide each of the boy's hands to each of his asscheeks.

"-Is spread your buttcheeks."

The pink haired boy grabs his ass and moves his hand, and subsequently his cheeks away from each other, spreading open his hole. His dick twitches as he feels both embarassment from exposing his hole for you to see and the wedgied cotton dig deeper into him.

"Mmm...L-Like this?" Narutaro says shyly and with an intensified blush.

"Yes, now just keep it that way."

You switch your grip back to the tighty whities and give them a good pull upwards. The dork moans as he's lifted off the ground.

"So, how does it feel?"

"Ah- My br-briefs...It's so deep in~!"

"Good, good." You say as you give the boy a quick but somewhat hard pat on one of his buttcheeks with one of your hands. You give the boy's whities another sharp tug.

"Ngh~ Owwie- It-It hurts but it feels... so good~!"

You chuckle at the boy's dorky reaction.

"Your reactions are so cute. That and your dorky tighty whities that you have on make you just the perfect wedgie boy." You praise the boy, emphasizing your points by giving the dorky underwear some sharp yanks on certain words.

More precum oozed from Narutaro's small, erect cock to his briefs which dripped down to the ground under the desk. The ample amount of semen that dripped from the boy's small, tender penis could hardly be considered pre-cum anymore.

You give several more tugs to the white fabric, each one being more intense than the last. Each tug makes Narutaro squeal and whine while the seams of his undies pop and fray. Until eventually...
RIIIPPPPP!

The boy's tighty whities rip. A huge portion of the ruined briefs is in your hands, while the other half hangs from his still spread but clenched hole.

"Mngh... C-Cyumming!" Narutaro said with an O-Face as his load stained both the front of his ripped undies and the ground.

"How naughty, Naru~ Cumming so much from that ripping wedgie~"

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

You chuckled, teasing the wedgie boy.

"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 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]!"

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 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
+5 Narutaro_Trust