Life of a Wedgie Masochist

Becoming The School Flag

I have been the football teams primary nerd since I've arrived at Bullsworth High School. Whenever they needed Projects, homework and test's done they would reach out to me. Although, they would often shove my head into toilets or trashcans and rip my Tighty Whities up my ass to persuade me to carry out the tasks I was still extremely honored and being a masochist, it was a dream scenario come true. I've been the quarterbacks favorite nerd, I've constantly got him straight A's on every single assignment and every test to keep him on the football team to win us state championships. Despite doing the quarterback a huge service, he would always reward me by using my face as a toilet brush or ramming my Tighty Whities up my ass. My mind has always wandered what would happen if I got him a failing grade in his classes and he couldn't play football. Even though the thought scared
me, it also filled my masochistic self with excitement. I decided to start getting the quarterback F's on all his projects, homework, and tests. I thought nothing of it as a couple days had passed.

As some days passed by suddenly a group of 10 Jocks were walking toward me in the schoolyard. Leading the group was the quarterback and behind him were all 9 the strongest linemen on the team. They surrounded me in the middle of the schoolyard. The whole school watched knowing a nerd had messed up big time and I so happened to be the nerd. The quarterback screamed

"YOU THOUGHT GETTING ME AN F WAS A GOOD IDEA? NOW I CANT PLAY IN THE FOOTBALL GAME THIS FRIDAY BECAUSE OF THIS LOSER!" As he's pointing at me. I try to calm the Jock down

"IM SORRY ILL FIX IT I PROMISE ILL GET YOU ALL A'S!" I antagonized the Jocks by begging but they weren't buying it playing right into my masochistic trap.

"ITS TOO LATE NERD, YOU KNOW WHAT HAPPENS TO NERDS WHO FAIL TO DO WHAT THEIR TOLD!" The quarterback yelled.

"And what happens to us that fail to do as their told?" I antagonized.

"THEY GET BULLIED!" The Jock screams, I run no more than 5 feet before having 3 of the linemen tackle me onto the grass giving me a face full of grass. As they surrounded me, they pulled my black sweats down revealing my Tighty Whities waistband which has the writing "JOCKS'S BITCH" which I wrote onto majority of the Tighty Whities in my drawer. They saw this and start laughing as my own underwear is admitting to being owned by them, to being dominated by the Jocks at Bullsworth. Three of the linemen grabbed my waistband and shot them up my ass carrying me by my Tighty Whities effortlessly.

"OW OWWW PLEASE STO-" I begged before being cut off by one of the Jocks pulling out their sweaty Jockstrap out of their pocket and shoved it in my mouth before ducktaping my mouth close gagging me with the sweaty Jockstrap.

"IF YOUR THE 'JOCK'S BITCH', YOU BETTER ENJOY THE TASTE OF MY SWEATY JOCKSTRAP SINCE YOU LIKE BEING OUR BITCH!" The Jock screams.

They carried me by my Tighty Whities to the front of the school where the flagpole is, the whole school watched as the most popular people on the team are tormenting me. They looped the hook through the back legholes of my Tighty Whities and pantsed my Black sweats off of me leaving my ass on display. I begged and begged but the sweaty Jockstrap and ducktape suppressed my cries for help.

"Any last words before you become Bullsworth's new flag?" The quarterback asks.

"MMMMPPHHHHH" I responded.

"What is that? Your honored to become Bullsworth's new flag? YOU HEARD THAT BOYS UP HE GOES!" The quarterback orders the other Jocks to pull on the rope.

"MMMPPHHH MMMMPH" I panicked and begged but it fell on deaf ears. All the linemen grabbed the rope and pulled with all their strength, my Tighty Whities are instantly deep in my ass. The whole school cheers and laughs as I'm brought higher and higher up the flagpole. This is my first ever flagpole wedgie and it is alot more painful than I've fantasized it would be as my balls are crushed my own weight as I'm held up by just my Tighty Whities. I'm brought to top of the flagpole when the Jocks tie the rope to the bottom of the pole. I let out a series of moans into the sweaty Jockstrap. The Jocks degrade me

"I BET YOU WISH YOU DIDN'T GET ME AN F NOW HUH!"
"HOWS IT HANGING LOSER!"
"BOYS SHOULD WE SALUTE TO OUR NEW FLAG?"
I try to get comfortable but ended up constantly spinning to my left on top of the flagpole leaving me on display for the whole school to see. The Jocks die laughing at the sight of my struggle. 3 of the linebacker Jocks bring a dumpster right under where I'm are hanging on the flagpole.

"WHENEVER YOU WANT TO COME ON DOWN, YOU CAN END UP WHERE ALL YOU NERDS BELONG, IN THE TRASH!" The quarterback screams. All the Jocks highfive each other laughing before walking back into the school.

"LATER LOSER, I WANT ALL A'S IN ALL MY CLASSES BY TOMORROW OR ELSE WE'LL BE SALUTING YOU AND YOUR DORKY TIGHTY WHITIES ALL WEEK LONG!" The quarterback warns before walking off with all the Jocks. All the other students watched me asI'm stuck bouncing and spinning myself to give everyone a show. I continuously moan into the gag as my g spot is constantly being flossed by my Tighty Whities.

I've finally become the #1 Bully victim after becoming the schools flag yet the thought of that excited me. The flagpole wedgie has been a dream of mine for quite some time now and after experiencing it it might be the best wedgie I've ever received. I was being flossed by my own Tighty Whities, all I can taste is the sweaty Jockstrap I'm being gagged with, students are still laughing at me.  My wedgied asscheeks are completely on display, I'm absolutely humiliated yet I loved every second of it. My asshole is swallowing my "JOCK'S BITCH" branded Tighty Whities while given a Flagpole wedgie by a bunch of Jocks. I got hornier and hornier as I continually moaned into my gag. I spread my asscheeks using my hands as I continuously bounced myself. A couple of Bullies looked and laughed degrading me

"OH MY GOD IS HE ENJOYING IT?"
"WHAT A LOSER!"
"HE HAS A BONER, WHAT A DORK!"
"ARE YOU ENJOYING LOSING YOUR VIRGINITY TO YOUR TIGHTY WHITIES?"
"YOU LIKE WEDGIES DON'T YOU LOSER"
"IS THAT WHY NERDS LIKE YOU WEAR TIGHTY WHITIES SO YOU CAN BE GIVEN WEDGIES!"
I tried my best to keep my wedgie fetish a secret yet the flagpole wedgie is making me hornier and hornier to the point where I can't hold myself back any longer. I continued spreading my asscheeks and bouncing myself as my Tighty Whities flossed my g spot perfectly. I was reaching my climax as the crowd laughed at my desperation. My hierarchy status being lowered to the nerdiest loser at this school that enjoys being bullied made me have an orgasm as I came in my Tighty Whities as I'm hanging from the top of the flagpole. As I was experiencing utter euphoria, the seams from my Tighty Whities started to pop and as I hung with the sweaty Jockstrap gag and skidmark cum covered Tighty Whities. My Tighty Whities ripped off as I fell face first into the dumpster below me. The crowd of Bullies surround the dumpster waiting for me to get out so they can Bully me. I looked up at the flagpole as my ripped Tighty Whities hung as a flag. Used as a constant reminder of what happens to nerds that wear Tighty Whities at Bullsworth. I love being a nerd and now everyone knows I enjoy it.