Bad Break

Ch. 19 Caught His Fall

"What happened? Did Kevin bother you again?" asked Jack

Sniffle "They ripped off my underwear in front of her, and now I'm commando..." Jonathan had a tear roll down his cheek

Jack peeked over the back to see Seth and Kevin laughing hysterically. Jack Sighed "Man why do they have to bully us so much, why???" 

Meanwhile Chloe looked at the torn red briefs and quickly dropped them just now realizing she was actually holding someone's underwear

"Bleh!"

She really did feel bad for Jonathan, she wanted to make it up to him, could say she had a crush on him. She had a thought of how she could make him feel better, she got up and approached the two.

Meanwhile Jack was trying to console Jonathan, while Jonathan was rubbing his sore behind, whilst his face was bright red. 

"Jonathan..." he heard his name and looked up to see Chloe with a concerned look on her face.

"Oh... Chloe, I um... I..."

"Shh, its okay we don't need to talk about it, I just um, wanna sit with you, that is if thats okay" Chloe looked at them both

"Uh.. yeah that's fine" sniffled Jonathan

Chloe looked to Jack "Jack, can I talk to him alone?"

Jack huffed "Yeah sure, thats fine" he grabbed his backpack and stepped over Jonathans legs and walked to another seat, while Chloe told him to scoot over. She rubbed his back and leaned her head on his shoulder 

Jonathans head popped up as he felt her head on his shoulder, he had never been touched by a girl, this sparked some feelings, well... a lot of feelings throughout his body. But she didn't stop there, she rested her hand on his upper thigh, slowly feeling at the fabric of his jeans. He felt a familiar tingling in his area, this causing Jonathan a sweat as he was wearing no support under his pants, for obvious reasons, his happiness clearly being obvious as it was tenting against his jeans without control. Chloe of course noticing, she looked up to him and grinned, groping his hard package, stroking it ever so softly. But the fun ended too quickly when they arrived at school

"To be continued" Chloe said to him as she got up and walked off

Jonathan felt like he was flying after what had just happened, his day went from horrible to incredible. He got up and cringed as his dick was uncomfortably pressing at his bare jeans, he turned a little red facing the window to adjust himself, as he did he was pushed by Seth as him and Kevin got off. Jonathan got up from the seat sighing and walking off the bus, he looked down and saw his raging boner, he looked around to see if anyone saw, luckily no one did and he decided to use his backpack trying his best to hide his boner. He caught up to his friend Jack and told him everything.

Since it was the first day, there was a big assembly in the gym. His walk very awkward and painful as he had no underwear on and not to mention, a stiffy. He asked his friend Jack if he happened to have any extra or anything, for some reason, he did.

"I thought that we would need them in case of emergencies, like a situation like this" Jack said

"Thank God for you Jack" Jonathan said as he looked in and saw they were cheap white briefs, but it was better then nothing. Jonathan ran to the bathroom took of his jeans and pulled up the briefs, they were really tight as he was a medium and these were small sized. "Ngh... there" Jonathan pulled them over his erection "That should do... mff" they were really tight on it, he had a small natural wedgie but it was fine.

He went back out to his friend Jack where they sat on the bleachers waiting for this assembly thing to start. He sat down and dropped his bag between his legs and looked around for Chloe, he saw her in a distance but she was on the other side, he waved to her but she didnt see him as there were many other students. He leaned forward, his head laying in his palm, but in doing this, the back of his shirt rose up, revealing the waistband of the tighty whities he had just put on, by now you'd think he would be more cautious of 'wedgie me' moments but he was too caught up with this girl. He felt a harsh tug at his underwear, so harsh the legholes already pulled out from his pants, he also heard pops loudly as they had stretched, he turned around and saw it was some random person he didn't even know 

"Cut it out..." Jonathan said shyly

"Why should I? You're wearing tighty whities your asking for it" the random guy said as he pulled again hearing it stretch and pop

"Let go dude, they're gonna rip!"

Jonathan turned and tried to push the guy away but he still had a grip on his underwear, and from his peripheral vision he saw Seth and Kevin approaching

"Haha need some help?" Seth asked the guy

"Can you believe this guy still wears these?" he pulled hard again

"He has been all throughout highschool, we've been giving this guy wedgies since middle school haha, in fact today we ripped them right out of his pants, and he still continues to wear briefs, lets give him a hanging wedgie and see if he will learn his lesson for once." Seth said as Kevin didn't really say anything

"Hahaha okay, from where?" the random guy said

"How about there" Seth pointed

Jonathan hearing everything and looking in the direction "No!! Wait guys hold on!" He said while struggling in his grip "Please don't give me a hanging wedgie, I'll ... uh I'll do your homework.. I'll, do anything! Please! AGh!" His heart was pounding. Seth and his new friend picked him up by his legholes and took him to a stairway that lead up to a walkway above the basketball hoop, used mostly for pep rallies and talent shows. Of course he struggled to escape the grip and he was being held up by two possible varsity jocks.

They got up to the very top and pulled up his tighty whities and dropped him "Dont! .....Uff!" the sound of ripping being heard then abruptly stopping as his fall was broken thanks to his underpants being snagged on the tip of a large sword plaque. The familiar feeiling of his underwear up his butt bringing a cringe to his face as the pain was unbearable as he dangled and didn't even try to struggle as he had been in many wedgies before 

The entire gymnasium going quiet for a few seconds then roaring with laughter and flashing lights from their phones. Chloe seeing that it was Jonathan and looked up to see Seth and Kevin up top as well as the other person, she shook her head and got up leaving the gym. Jonathans face red as an apple he sighed and turned slightly around to try and pry his underwear off from the sword, but it was not use he was too heavy. His legholes beyond out of his jeans, he dangled in defeat. He heard and felt his underwear start ripping, a lot, shhhrrrip riiiiip, he looked down spreading his legs and saw that right below him was the basketball hoop, he looked back and saw only the waistband stuck on the sword, he tried getting into a more comfortable position but then SNAP! he went falling right into the basketball hoop butt first, getting stuck again with his butt crack and ripped underwear hanging out of his pants below.

"This can't be happening!" He thought still bright red