Life of a Wedgie Masochist

What 'Hanging' Out With The Jocks Outside of School is like

After a full week of being tormented by the Jock's. A full week of being wedgied, swirlied, wet willied, canned, and shoved in lockers finally the weekend was here. I can relax and try to enjoy some alone time without being bullied. I was home relaxing, I had on white tube socks, a polo shirt, black basketball shorts and a pair of Tighty Whities that were labeled "JOCK'S BITCH" on them. Despite not being at school, I still had to make it known that I served the Jock's, that I was the Jock's property and that they owned me. I played video games all night until I got bored. I decided to go to sleep. In the morning, Bullsworth's quarterback had rang our doorbell. My parents answered the door, the Jock asked them if I was home and they replied yes he's still sleeping. My parents let him in, letting him know that they were leaving. They let the Jock know that it was only going to be us in the house. I was steady asleep. The Jock crept up into my room, he pulled out a chain with a hook on the end. I laid on my side facing my ass to the door and to the Jock. Sticking out of my black basketball shorts were the waistband of my Tighty Whities. The quarterback read "JOCK'S BITCH" on my waistband tried his harder to hold in his laughter to avoid waking me up. He took the hook and attached it to the back of my waistband. The Jock held the chain in his hands getting a really good grip. He counted himself down,

"3.....2.....1......WAKE UP LOSER!" The quarterback screamed in my ear, as I slowly opened my eyes. Unsuspectingly, the Jock gripped onto the chain and pulled as hard as he could ramming my Tighty Whities up my ass. My legholes were already up to my shoulder blades as I screamed and moaned in pain.

"Uuugh... Pleease stop" I cried as I was woken up by an intense wedgie. Nevertheless, the Jock's unrelenting strength on the chain kept stretching my Tighty Whities further up my ass, crushing my morning wooded crotch. The seams of my underwear started to pop as he dragged me off of my bed onto the ground. My Tighty Whities ripped right off of me, resting onto the hook as if the Jock had just gone fishing and caught himself a loser.

"HAHAHA, YOU LIKE THAT WEDGIE ALARM CLOCK? SEE, NOW YOUR WIDE AWAKE NERD!" The quarterback bullied me.

"Owww... What are you doing in my house?" I asked the Jock.

"WELL YOU SEE, WE DON'T HAVE ANY FOOTBALL PRACTICE SO I THOUGHT TO MYSELF. WHAT OTHER BETTER WAY TO SPEND MY DAY THAN BY BULLYING MY 'BESTFRIEND' MY FAVORITE LOSER!" The quarterback teased me. He took the ripped Tighty Whities and held them up inspecting them.

"MAN YOU NEVER LEARN YOUR LESSON NERD, YOU ALWAYS FORGET TO WIPE. JUST BECAUSE OF THAT GET OVER HERE DORK!" The Jock bullied me staring at my ripped Tighty Whities that had skidmark stains on them. The quarterback grabbed me and pinned me onto my bed. He took my Tighty Whities and gagged me, shoving the skidmark stained side into my mouth tying the Tighty Whities to the back of my head. I couldn't speak now. The Jock walked over to my drawer full of Tighty Whities and grabbed a random pair. On the pair it read "JOCK'S SLAVE"

"WOW LOSER YOU REALLY DO LOVE BEING BULLIED BY US! YOU REALLY TOOK THE TIME TO WRITE ALL OF THESE ONTO THE WAISTBANDS OF YOUR TIGHTY WHITIES, SO PATHETIC HAHAHAHA!" The Jock pantsed me exposing my bare ass and threw the pair at me. I put them on and pulled my black shorts. The Jock than shoved me onto my bed face first. My ass was arched up when the Jock lunged at the waistband of my Tighty Whities. With a swift movement the Jock shot my Tighty Whities up my ass and kept lifting me off the ground. My weight was used against me as he split my ass in half with my Tighty Whities. I screamed and moaned in pain into my skidmark stained gag.

"MMMMPPHHHH MMMMPPPHHH" I cried into my gag as he crushed my balls and split my ass into two using my Tighty Whities giving me a brutal bouncing wedgie. My Tighty Whities started to stretch out more and more as the legholes were up to my shoulder blades. With one brutal bounce, the Jock ripped my Tighty Whities right off of me as a loud ripping sound followed by groans echoed throughout my room.

"WHAT TYPE OF CHEAP ASS UNDERWEAR ARE YOU BUYING NOW NERD?!" The Jock teases me as he goes searching into my drawer to grab another pair when he discovers it. In my drawer I have a pair of Tighty Whities that I labeled "QUARTERBACK'S LOSER" in black bold letters on the waistband.

"WELL WELL WELL, LOOKS LIKE I HAVE A FANBOY! LOOKS LIKE YOUR THE 'QUARTERBACK'S LOSER' YOU LIKE BEING BULLIED BY ME LOSER?" The Jock degrades me when he pants my black shorts off of me and slips on the "QUARTERBACK'S LOSER" labeled Tighty Whities onto me. The Jock walks me out of my room and out of my house. I'm only in my White tube socks, Tighty Whities and polo shirt. He opens the front door and shoves me out into the frontyard. In my frontyard we have a house flagpole where we have our american flag hung up on it.

"HOW ABOUT I MAKE MY 'LOSER' THE NEW FLAG OF HIS OWN HOME? WOULD YOU LIKE THAT NERD? YOUR PROBABLY EXCITED YOU LITTLE PUSSY, YOU LOVE IT WHEN I BULLY YOU DON'T YOU?" The Jock degrades me as he shoves me to my flagpole. He grabs the secondary rope and lowers it revealing a metal hook. The Jock effortlessly slips my legholes onto the hook.

"YOU READY DORK? ON 3......... READY, 3! LIFT OFF LOSER!" The Quarterback screams as he pulls the rope as hard as he could bringing me to my tippy toes off the first pull, I groaned in my gag as I knew it was over. All my neighbors were going to know that I'm nothing but a Bullied Loser. My thoughts were disrupted as the Jock splits my asscheeks with my Tighty Whities lifting me 2 feet off the ground. The Jock relentlessly heaved on the rope until my nerdy ass was hanging at the top of my flagpole.

"HAHAHAHA! LATER LOSER, I HOPE YOUR NEIGHBORS ARE ENJOYING THE SHOW! SEE YOU AT SCHOOL MY 'LOSER'!" The Jock bullied me before walking off leaving me stuck hanging on the flagpole of my own house. I was screwed. The Jock doesn't only embarrass me infront of the entire High School but has embarrassed me infront of my entire neighborhood and family. I bounced up and down trying to help aid ripping my Tighty Whities. The feeling started feeling more satisfying as it rubbed against my g-spot, flossing my ass. I started to have an erection and let out moans into my gag. I spun myself around and hugged my flagpole, wrapping my legs and arms onto it. I started bouncing and rubbing my erected wedgied crotch against the flagpole. I was losing my virginity to my Tighty Whities as I grinded against the flagpole. I started reaching my climax. I increased the speeds I was grinding the pole and bouncing forcing me to taste the cotton of my Tighty Whities with how far up they were up my ass. I orgasmed shooting my loaded into my Tighty Whities as my cum drizzed down my flagpole leaving a long streaking stain on the flagpole. I had to wait for my parents to get back and they weren't going to be home for several hours so a loser such as myself should get more comfortable staring at this view of my neighborhood.