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

R-1A

"Turn around for me, Naru."

"Okay, [Reader]~♡"

Narutaro eagerly turns his back to you. This is going to be fun.

You reach inside his pants and get a hold on the soft fabric hiding underneath. Then, you slowly pull up on the undies for a bit, letting only a small bit of the waistband peek out from Narutaro's pants. You lean in close to Narutaro's ear and softly whisper;

"Are you ready, wedgie boy?" You say, punctuating your question with a slightly harder tug.

"Mmm... Yes, [Reader]. Naru's ready." An aroused Narutaro says softly, his breath shaky. He's looking forward to what's coming to him.

You smile for a brief moment. Then, you tug on Narutaro's undies with at least 60% of your strength.

"Eep!" This earned you a high-pitch squeal from the petit wedgie boy as his tighty whities started to stuff themselves into his ass and squish his erect cocklet. Already, Narutaro's legholes are outside his pants, but more importantly, these tighty whities are showing a great deal of resistance, which means... they're not so stretchy. This could be a good opportunity for another lesson. But whatever, you'll still have to stretch out these undies just a bit more to proceed with the lesson.

Next, you switch your grip to the pink haired boy's exposed legholes and bounce him. Albeit, not as strong as you would've hoped to because you don't want his tighty whities to rip too soon.
Each bounce pushes more of the undies into Narutaro's crack and earns you a pained whimper from your wedgie disciple.

Still bouncing the poor boy, you ask him;

"Do you remember what kind of wedgie this is, Narutaro?"

"Ah– Ah— It's... ah... um... a b-bouncing ngh... wedgie!"

"Good boy~"

"Ah... nghaah~♡" The praise-loving maso boy moans out with drool dripping down his chin.

You continue gently bouncing the lightweight boy while also walking to where the real lesson for today will happen— the tall metallic coat rack.

When you arrive there, you release Naru's white briefs and quickly get a beanbag chair.

Narutaro, still slowly recovering from his bouncing wedgie asks;

"Aww... Is the lesson over for today, [Reader]?" with a sad pout on his face.
"Far from it, Naru. Just stay there." You respond as you put one of the beanbags on the floor in front of the coat rack.

You go behind Narutaro and tug on the legbands of his stretched out undies once again. Narutaro whimpers as his tight undies chafed against his ass and crotch. You stand on the beanbag chair, and sure enough, you were able to successfully attach the wedgie boy's tighty whities on one of the coat rack's hooks.

You let go of the boy's legbands, causing him to drop with a bounce.
"YIIEEEP—!" Narutaro squealed as he bounced on the thin, razor-sharp strip of his underwear. The seams of the pink haired boy's underwear started to pop. Although the tighty whities seemed to barely fit Narutaro– or at least just not be stretchy– they were somewhat durable enough to support Narutaro's weight. Narutaro's body slowly swayed like a pendulum as he hung by his undies, his feet failing to reach the floor. The dork cutely whimpered in pain as his undies rested inside his asshole and between his balls.

Fuck. This scene was so hot.
"How's it 'hanging', Narutaro?" You joke after you let him get settled into his first hanging wedgie for a few minutes.

"Mm~ It feels so good..! Auughh..." Naru lightly kicks his legs and groans as he continues to slowly sway by his undies.

"Good, good."

"—Now for the cherry on top..."

You get closer to the dork and yank his pants down to his ankles!

"[Reader]...?!" A surprised Narutaro exclaims with a blush on his face when he feels the cold draft on his legs.

"...Perfect."

Now with Naru's pants out of the way, you can see his pained balls popping out of the legbands of his briefs that tightly wrapped around his erect but still small penis. This sight makes you so aroused, and clearly, Narutaro's aroused too as evidenced by the small wet stain where the outline of his tip is on his briefs.

As fun as giving Narutaro wedgies is, you still have to hold your end of the deal and teach him about the wedgies he's enjoying.

"Now, Naru, you're getting a 3-for-1 wedgie lesson from me today."

"The wedgie I gave you where I hooked your nerdy undies is called a hanging wedgie."

"When I pulled your pants down, I gave you a pantsing— which means, the wedgie you're in right now is called a hanging pantsing wedgie."

"—And, oh yeah, different types of wedgies can mix. Were you listening to me or does the wedgie feel too good for you, dork?" You teased, the last sentence having been said as your finger softy traced the outline of Narutaro's tip all the way down to bottom of his crushed scrotum. This earned you a twitch from the boy's pained and petit penis and a gasp from Narutaro himself.

"N-Naru was listening, [Reader]!" Narutaro replied, biting his lips with a pleasured look on his face.

"Good boy, Naru~"

"I almost forgot to mention... Those white briefs..."
"Wha-What about Naru's briefs, [Reader]?"

"Those are called tighty whities, and they're so nerdy that they make whoever wears them just the perfect target for wedgies— like you." You can see that this teasing makes Narutaro's dick more excited.

"Moving on, let me introduce one last type of wedgie for today..."

"This kind of wedgie could also double as a way for you to get out of the hanging wedgie~

"But... before we proceed, I'll let you choose, Naru. Do you want me to assist or do you want to try this on your own?"

What would Narutaro want to do?

a.) "Naru wants you to help him, [Reader]..." (proceed to R-1C)
b.) "Naru wants to try it on his own!" (proceed to R-1D)
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MetaNotes:
+25 Narutaro_Dominance
+5 Narutaro_Trust