The Wedgie Bet

Summer Homework

"Let me go, let me go!" I call out to my guy best friend Milo as I swear, if my panties were pulled any further he might rip me in part.

"How did you even get in here!"

Milo laughed at my predicament, taunting me. I woke up to him giving me the hardest wedgie I ever experienced distraught and humiliated.

"Squirm more and I'll just pull harder," he proclaimed laughing before my underwear was pulled so hard and stretched so far that he snapped it on my forehead.

I immediately reached to grab it, to which he respond with a tisk, grabbing my arms and pinning them behind my back.

"You lost you're bet loser, now take it," he responded.

I groaned, fighting back to which he laughed more at, easily holding me in place.

"To how I got in here, you know your mom loves me.. I just told her I was working on summer homework with you and she was more then happy to let me in."

"This isn't fair, if I didn't trip I would've won!" I exclaimed struggling against the wedgie, causing it to ride more up my ass and him to grip me down harder.

Just the other night I lost the bet to Milo, but he quickly jumped on it, making sure my last days of summer break were miserable.

"It's not even the start of first quarter yet now let me go!" I cry out.

"Hmm, would you rather me catch you after both our practices got out and hang you in my locker by these adorable panties until they rip?" he taunts.

Suddenly embarrassed, I remember I wore my heart design granny panties to sleep, causing my face to heat up. I freeze for a moment, before once again squirming against my grip.

"Aww, speechless now bug?" He questions, pulling on the bunch above my crouch, intensifying my atomic wedgie and causing my head to shoot back.

"You- you can't do this," I state back now less confident then before, causing him to laugh once again.

Suddenly, Milo drags me off the bed by my underwear causing me to yelp, as he lifts me so high by them that I'm now on my tippy-toes.

My hands immediately shoot back to my underwear trying to grip it from his hands, as I cry out. "Do you want me to pull harder," he questions?

"No— please," I respond retreating my hands, flustered and empty minded by the pain and humiliation now filling my mind.

"Good," he responds.

Still on my tippy toes I whine begging for him to let go before he continues. "I want you to understand, you lost this bet. Now I'm free to wedgie your however I please. I don't want complaining or I'm going to be more mean, do you understand?" He asserts with a harder tug, lifting me off the ground before I land on my tippy toes once again.

I panic, squealing out in response, "but Milo it's not fair you won by default!"

Milo used to give me wedgies as a joke, but not like this. I'm convinced now that he's enjoying bullying me, and it's no longer just a prank.

Suddenly Milo let's go and spins me around, my sight glued to his plaid pajama pants, suddenly embarrassed to meet his eyes. He grips the front of my underwear lifting me to my tippy toes once again.

"Ow that hurts!" I call out as the cotton slides into the innermost part of my privates, immediately burning.

"Look at me," he affirms lifting harder, causing my face to flush. Something about him wedging me from the front felt so much more emberrasing.

I keep my eyes glued to the floor and he lifts me up, causing my underwear to press even harder against my sensitive parts as he lifts me up to my tippy toes and back down causing me yelp once again before looking up.

"Okay,okay!" I yell out before meeting his deep chocolate eyes, that are now squinted in an unrecognizable way.

"He keeps his grip firm on my underwear causing me to wince in pain as I try my best to hold his gaze.

"We can rematch in the race, but if I win I will hang you off the back of those bleachers and leave you there until you rip- and the wedgie deal extends to the semester not just the quarter," he adds with an annoying smirk.

My eyes widen at his statement, taken aback by his sudden request to torment me so badly.

What is he getting out of this?

The thought leaves my mind as soon as it comes, my mind too focused on the sharp pain in my sensitives.

I almost say no due to how confident he seemed, but I remember how far behind he was in our race.

"Fuck de-deal, now let me go," I stammer out, causing him to smile and let go.

I stumble in response, regaining my balance and immediately reaching to fix my horrible wedgie.

"See you tonight bug," he lets out before leaving my room. Once my door shuts I pick out my remaining underwear from my crotch and asshole groaning in pain.

What the fuck.