Whatever I said next next was replaced with a squeak as I clenched my butt instinctively from what seemed to like a pull…
Only for Jess to laugh, making me realize she’d given me small playful tug just to mess with me at the start.
“Heh, you’re pretty jumpy there lil’ bruh~” Jess said as she ruffled my hair; “Now c’mon, don’t clench your butt cheeks, ‘kay? Not gonna do you any good…”
I sighed as I immediately unclenched my rear… Just as I’d relaxed the last square inch of one of my cheeks, however?
“Wedgie-Nator!”
I squealed as I felt myself being lifted into the air, my upper body dipped towards the floor, with my hips and butt tilted up as Jess hauled me up by my baby blue briefs!
Jess giggled loudly at the noises I’ve made and she kept me on my tippy toes. My briefs were stretched to my neck in one fell swoop and now she began the arduous process of stretching them all out.
“Look who’s got his special undies out. I love the blue brah.” Jess cooed, “Most boys here have only boring tighty whities. This one has color!”
She yanked me off my feet and began to bounce me up and down. “Think I’ll call you Little Boy Blue instead of [Anon].” she teased.
“Could you NOT?!” I ask as I kick in midair awkwardly, given the embarrassing pose I was in thanks to how Jess dangled me.
“Chill lil’ bruh, just a pet name… [Anon]’s still a cute name!” She said as she gave me another bounce before she transitioned to just walking on foot, a skateboard held under one arm while also using her other hand to keep me suspended in midair by my underwear, much to my chagrin.
“Never had a girl give you a tour like this, have ya?” Jess asked as she raised me up a bit more, just to make sure she didn’t drop me.
“Please lemme go!” I squeaked out. I was squeezing my legs together due to the fire between them raging.
“Heh, of course bro.” Jess said with a wink.
I then realized my mistake as she dropped me down. However my briefs were attached to the lockers and to my bafflement, they stayed stuck!
As such, when I fell down I fell down into a huge hanging wedgie!
“Eeeeeek!” I squealed loudly while Jess roared with laughter and began keeling over hugging her stomach.
“I see you’ve got a bit of plumber’s crack forming there little dude!” Jess said while laughing.
It took a moment or two for me to realize what she was saying as I thought over how I was hanging…
I yelped with embarrassment as I dove my hands up to cover my buttcrack peeking out a bit over the top of my pants thanks to how I was hanging from the locker.
“Quit looking!” I protested with an annoyed, blushing face.
“Ahahahhaha! Oh you should see the look on your face!” She said as she ruffled my hair while I hung from the locker.
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