A bully out of his league

My name is Alex Brooks and, if you had met me two weeks ago, you would be taking with the king of Saint Monica highschool. Getting that tytle was not to hard, as I had both the looks and strenght to make all those losers and nerds bow to me. I am five feet and eight inches tall, with short, coal-black hair and green eyes. I am no captain of the football team, but I still can lift two nerds at the same time without breaking a sweat. Infact, that is what I did the first day, with enough strenght to ripp their nerdy underwear into shreds and leave those two twitching on the floor with tears in their eyes. I got detention, but I also gained the other's attention and, most importantly, Carlotta.

As captain of the cheerleader team, she was the school's most popular and desired girl and she had the looks to show it. I am not talking about that long, blonde hair of hers or those blue eyes she has, but her perfectly-hourglassed body, with a cleavage and butt which did not seem from this world. Add to that the fact that she only wore mini skirts and tank-tops and you can understand why I was so eager to get to the top and get her as my girl. Of course, if I knew just how self-centered she was and how little coversation she had apart from clothes and the cheerleader team, I might have not been so eager to get to the top.

Who am I kidding? She was so hot I would not have cared anyway!

Well, you may ask now, how did this dream of a life end? If you want to know it, we should start with a name: Paul Sulivann. Imagine the nerdiest nerd who ever walked this Earth and multiply it by ten: Short, scrawny, with thick glasses, suspenders, knee-high socks and a tie. I have to make a double take to make sure I was just not imagening things. And more surprising still: He was a senior, just like me! Chuckling to myself, I cracked my knuckles and waited until he was leaving class, books close to his chest, to give him the proper "greeting" he deserved by slamming him face-first on the locker.

"Ack! P-Please, don´t!" he begged so fast, I almost felt a little dissapointed. Then I saw the line of white cotton coming out of his shorts and my smile returned with a vengance.

"So, you are the new nerd?" I chuckled "Why I am even asking? Of course you are! Just look at those clothes!"

Paul groaned and closed his eyes. By the time my fingers moved to the waistband of his tightie's, I could see the sweat pouring all over his skin. I allowed him another moment of terror, just so he could better regret his choice of coming to high school like this. Then, I squeezed my fingers into the cotton and pulled hard! The fabric erupted like a volcanoe and so fast, I almost fell back! Luckily, I pushed one of my feet back and enjoyed the sight of the growing stream of white tightie's, going past the screaming nerd's shoulders and then his head. I did not even know underwear could stretch that far! By the time I snapped the waistband over his nose and left him to twitch on the floor, I was bending over, laughing with tears in my eyes.

"We are going to have so much fun together!" I said, before picking him up by his trembling legs and releasing him head-first into one of the trashcans at the school's gates.

And that is what happened for a couple of days: He came, I forced him to bend over and then lifted her off the ground by his tightie's. I even got Carlotta to join in the fun a couple of times, me tugging his undies from the left and her, from the right. He kicked and screamed so hard, I almost swore we were about to tear him into two smaller nerds. And every day, he had to drag himself back home, with a long trail of white fabric stretching out of his shorts and covering the whole street. It was so much fun, I left the other nerds alone and focused only on Paul, believing that nothing wrong could come of the fun I was having.

I was still thinking that the fourth morning after Paul came to my school. It was a warm, spring day and I had just left my home wearing some jeans, combat boots, a leather jacket and a matching black shirt with a big, grinning skull in the middle. There were no homework or exams in my mind, only Paul's frightened face, as I knew it would be once I caught him trying to sneek into the classroom and then have a bit of bouncing fun with his tightie's. It was such an amusing image, I almost did not spot a hottie at the street's corner, arms crossed, waiting for someone to come by. And she was hot! She was more than a head taller than I, with smooth, ebony skin and the tough body of one of those WWE wrestler-models. Grinning, I winked at her, getting a long eye-roll and a scoff before she froze and stared at me again, this time with a look in her blue eyes I could not read.

"Are you Alex Brooks?" she asked in a monotone which still was infuriatingly sexy for me.

"Yep. And sorry, I am already taken. Then again, if you really want to, I won´t tell my girlfriend" I said, moving closer to the older girl.

What happened next, I still have trouble understanding. One moment, I was grinning at her. Then next, I had spun around and, still in mid-grin, could feel the back of my jeans stretching back, so my full, grey-covered rump, was exposed to the hottie. Finally, my brain worked once more and I began to look around in shock, before freezing as the girl's full hand sunk into my boxers. The feeling of her warm fingers against my buttocks was so nice, I almost did not realize how those same fingers clenched around my underwear until some cloth sunk into my crack. The next thing I knew, was just why my victims screamed so much whenever I gave them a wedgie.

"AHIIEEEEEE!!!" my world became a blurr as I was shot off-ground, arms flailing almost as much as my legs. At the back, my ass felt as if someone had sunk a whole spear into it! I howled, screaming at the clouds with every cell in my lungs. Then, only a moment after the tug started, I felt my waistband brushing against the back of my neck. My eyes crossed. Just how had she managed that?! These were boxers, not Paul's ultra-stretchy tightie's!

And, unlike them, they just could not stand the full power of that woman's ultra-wedgie. One bounce and I heard a tear on the back. Two and, as my body bent-over forwards, I heard a louder one. By the third bounce, I could almost see the insides of my brain at the pure hellfire in my crack, just before the fabric gave up and threw my to the floor with three strings of grey gliding slowly behind me. Still not saying a word, that woman picked me up by my jeans, sinking them into my crack as she carried me to a trashcan and dropped me head-first into it, leaving me blinded by rubbish with only my legs to kick wildly out in the air.

After much swining around, I managed to tilt the can to a side and roll out, groaning and covered in waste. There was no sign of the girl and I remained laying there, silent, still trying to understand just what had happened. I somehow managed to get back home, grab a fresh pair of underwear and then reach the school right on time. But I was to lost to listen to the classes, or even hunt Paul down. I could only think about that girl, that hot godess who had just kicked my ass without a word. I began to day-dream during the break, imagening myself fighting that girl again and wining her wild heart. Carlotta was gone from my mind, only that mysterious amazon mattered now. Once the bell rang, I decided to just hang Paul up the flagpole by his new pair of tightie's and throw his pants into a trashcan so he could moon both the other students and the teachers who later came to his rescue.

My heart almost leaped out of my chest when, as I was about to reach my home, I saw the goddess waiting at the fence, her eyes dangerously narrowed to the phone she had on her hands. Then she heard me and her glare only increased, which I did not mind. She was even hotter when angry.

"You got me good back there. So, what's your name?" I said with a smirk "I like to know the name of the people whose ass I am going to kick"

"Mandy" she said, her glare never faltering.

"A beautiful name for a..." I could not end my pick-up line. One second and my belt was gone, leaving my jeans to fall down to my knees and my new pair of dark-blue boxers to be shown to the world. Next, a hand to my neck, bending me forwards so I was staring at my knees when Mandie's warm hands clenched around my underwear for the second time "How can you be so faaAAAASSIIIEEEKKK?!?!" again, my boxers seemed to fly towards the sun, leaving my buttocks to bounce pale and free with cotton stuffed deep between them. One more tug and I was kicking off ground again, only this time Mandy caught my head between her amazing thighs and continued to pull as high and hard as she could.

Twenty seconds and I was once more kissing the cold floor, only this time my butt was bare and the strings of fabric gliding down to my ass and hips were coloured blue. Groaning and sore as I was, I did not fight when Mandy pushed my head up with a finger pulling up my chin. Infact, once I was eye-to-eye with that gorgeous amazon, I prepared my lips, believing that this would be the moment of the kiss. Instead, I felt something sour being pushed into my mouth before my chin was released and I realized I was chewing my own sweaty, ripped underwear! Even then, embarassed as if I were a lowly nerd, I could not keep my eyes away from her, or how she swung those perfect buttocks as she walked away.

The next morning, I thought myself clever as I waited at the corner half of an hour earlier than usual, peeking my head over with a new fresh of stretchier boxers under my jeans. Fifteen minutes later and nothing. Twenty and I felt two fingers giving a light tug to my new, exposed red underwear. Gulping in fear, I began to turn my head back, even if I did not need the confirmation. Two gorgeous blue orbs stared at me from above. Trembling, I tried to say something, but instead I screeched as I was once more rocketed off-ground by my own underwear, only this time at least I did not lose my pants in the process!
The amazon bounced me with one hand, then another, each tug slicing my innards until I could almost felt my buttocks bursting out due to pressure.

Four minutes of tugging later and I was, once more, with my stomach on the ground. This time though, my underwear had not ripped, which did not help matters as Mandy had pushed my feet through the legholes so I would be giving myself a jock-lock wedgie for a while. Grunting at the pain in my ass, I watched Mandy go and then crawled back home, hoping beyond hope that my mother would not catch me in such an embarassing position.

This time I went bersek on Paul's tightie's, wrapping him up in that white fabric and then dumping him once more in the trash. My crack was still sore after the wedgie-madness of that morning, but a firm squeeze of Carlotta's bubble butt and a wink from her, managed to lift my spirits. With Paul still struggling in his lunch-spot at the trashcan, I brought my blonde bombshell of a girlfriend to our own spot and made-out for a while. Giggling, she grabbed the neck of my shirt and pulled me closer, until her scarlet lips were brushing my ear.

"My parents won´t be at home for a while" she purred.

Once the bell rang, I picked Carlotta up and ran to her home, with the speed only a promise of a good time can provide. I was so eager, I almost forgot about Mandy. Unluckily for us, she had not forgotten about me and she was waiting just a street and a half away from my girlfriend's home, her eyes quickly sharing that gorgeous glare she had to me, with Carlotta. I froze, trembling with the same intensity like a guy who had just been caught in bed with a lover by her girlfriend. The cheerleader on my arms just stared confusedly at Mandy and then let out an angry growl, jumping off my arms to return the glare to Mandy.

"Hey, out of the way bitch!" she snapped "You really don´t want to mess with him"

For a heartbeat, I swore I saw an amused smirk on Mandie's lips, but it was so fast it could had been my mind playing tricks as well. Stretching her arms up, Mandy took a step forward, making my girlfriend take one back, her eyes not so confident now that the much-taller woman was coming towards us. Soon, she was with me, shacking so much her skirt began to slide down, revealing a large pair of pink, granny panties, the prize Carlotta had to pay for her big, bubbly behind. At that moment I also remembered my own new pair: An extra-stretchy pair of white boxers with pink hearts and a waistband to match. Looking at each-other, we spun around and were about to flee for our lives, when Mandie's fingers found their mark.

"NOOOOO!!" granny panties and stretchy boxers yanked us back, screaming, with our jaws dragging across the floor. Then Carlotte flew, eyes crossed stupidly as Mandy managed to keep her airborne for a painfull second before she fell and I myself was rocketed up towards the cloud, whailing as I started to taste the sweaty cotton inside my crack! Again, Carlotte came next, this time losing her skirt so her fine, big booty could jiggle naked with just a slim line of cotton to hide it. I soon stopped seeing that fine view though, for Mandy was quick to lift me up a couple of inches higher than my blonde girlfriend. Teeth gritted, I curled into myself, knees glued together, arms flailing uselessly and crack smocking after each, fiery tug.

Mandy had "a heart" though and was "kind" enough to drag our sore butts across the street and pull us up towards the branches of the tree near Carlotte's home. We both yelped and rolled our eyes in agony when our undies caught us in mid-fall, leaving us to dangle and spin under the tree, mooning everyone who passed by with our pale soccers. Nodding to herself, Mandy turned around and left us to whimper in our hanging wedgies.

"This...is not so fun from the other side" whined my girlfriend as she kept slowly spinning by her heart grannie's.

I nodded and blushed hard when I heard childrean laughing at us from behind. Pressing our faces against the fence for anonymity, we kept hanging there, suffering the teases of children and teens alike for what seem like a lifetime, before our underwear gave and we fell with high-pitched yelps. Needless to say, Carlotte was not in the mood for a fun time, or anything, after that time at the tree. And, strangely enough, neither was I.

The next morning I went ready for a fight. I had trained the whole evening until my legs had given up and had bought the last pair I would like to wear, but the most useful against Mandie's brutal yanks: Tighty whities. Just wearing them made me want to puke. But war was war and I wanted to win against Mandy, before then wining her heart. I traded blows with an invisible foe, training until I was sweating with the effort. Ready and eager, I spun around the corner, fists at the ready to find...my girlfriend...and her granny panties?

Carlotte was all red, her new pair of pink grannie's with white polka dots stretched all the way over her tight, red shirt to then rest down to her nose, forcing her to bend her neck back and push her jiggling, jean-covered buns up. I was so entranced by the strange hotness of it all, I was to slow to notice Mandie's shadow coming from behind, or her fingers grabbing my exposed tightie's....

"OWIEEEEE!!!" the tightie's were over my head in one yank and down to my chin after another. Blind, in agony and smelling and tasting my own crack, I bent back, flailing my arms uselessly while my legs trembled at the fire in my crack. Still-whimpering, I was dragged to my girlfriend's side and then tied up with some rope (which I did not mind since I could feel Carlotee's crack pressing against my chest. Stumbling, we were pulled across the street until we began to hear the sound of laughter once more. Then it hit me...some of the teens who had seen our hanging wedgies were from our school!

"The kind and queen of losers have arrived!" sang someone.

"LOSERS!" taunted another.

Then, they tugged our jeans down. That was the last straw for Carlotte and I to finally sobb our eyes out, as we knew that now our of our popularity was gone. She would no longer be a cheerleader, or be invited to other teams who she had laughed at for so long. I would no longer be feared, but become the top nerd of the school, a tighty-whitied loser who would bend over to jocks and nerds alike and get lifted by his underwear. We did not even feel the flagpole as we were pushed against it, our bottoms still facing the ground. Then, I felt the cotton being pushed off my eyes. Blinded by the light, I looked back and froze when I not only saw the gorgeous Mandy, but also Paul...and they were kissing!

"See? I told you I could handle it" winked Mandy to the nerd.

"Thanks" said Paul with tears in his eyes.

My mouth did not close, not even when we were lifted at the flagpole's very top and left to moon the whole school and neither when our panties ripped and we had to do our walk of shame back home. I had been beaten, by Paul of all people! That hurt almost as much as all of Mandie's wedgies combined. Because, now I knew, I was the school's biggest loser...

--

Dear diary,

Thanks to my sweet, wonderfull girlfriend Mandy, today begins the first day of my new life! No one picks on me anymore, or teases me about my looks. I can have lunch in peace and can go near a trashcan without the fear of being thrown into it.

It is also the first day of a new life for Alex and Carlotte too. And I know they were mean bullies and all, but I can´t help but feel a little sympathy for those two. After the flagpole, they are no longer the school's most popular pair and their desperate tries to reverse the situation have not helped them much in the matter. They are now the school's "top wedgie couple" and the cheerleaders have taken the job of making sure they stay that way until graduation. Right after class, they have given them both atomic wedgies and pushed into the same empty trashcan before kicking them downhill. Tamara, the new captain of the cheerleaders, says that this will be a new tradition for those two.

Anyway, at least they are not me!

Sincerely, Paul.