Grade A wedgie

A Quick Lesson✏️

"What is my name?" Mr. Alfonzo said as he pulled harder on Grayson's baby blue boxer briefs, having them dig deeper and deeper in Grayson's ass.

"Sir!!!" Grayson said with pain in his breath as he felt his balls being pushed inside of him.

Mr. Alfonzo undid the button on Grayson's black slacks and yanked the down and off his shoes, taking them all off, put leaving his socks on his feet.

Grayson felt the cool breeze from the window on his legs and could feel it tickle his bum, but all he could really feel was his briefs being tug further up his ass.

"Do you like being wedgied?" Mr. Alfonzo said as he flipped Grayson around so he was pulling on his front waistband. "Would you prefer a Melvin?" Mr. Alfonzo said as he pulled the underwear until the leg holes were exposed.

"No...Ow...No sir! Ow" Grayson said as though he had helium in his breath.

Grayson could feel the underwear slowly coming out of his ass as it was being redirected into smashing his nuts.

"Then why do you not remember to call me Sir, you twit!?" Mr. Alfonzo said as he was able to pull Grayson's boxer briefs to Grayson's own chest.

"Because I'm a little nerd, who needs to be wedgied to feel useful!" Grayson barked out as though he had rehearsed it. Which he basically did saying it to Mr. Alfonzo for almost 4 years now.

"Maybe we should do a "squeaky clean" start?, what do you say nerd? Make sure you remember?" Mr. Alfonzo said with a condescending tone.

"Please Sir! I can't rip another pair...my mom will kill me!" Grayson said with tears and pain in his eyes.

Mr. Alfonzo just laughed

"Oh is that what the big nerd is worried about? Making mommy mad? Well..."

Mr. Alfonzo moved his one hand on the back of Grayson's already stretched waistband....

"If that's the case then the only thing I can do to make sure, mommy doesn't get mad is too..."

Mr. Alfonzo put his other hand on the front of Grayson's front waistband and gripped it as tight as his other fist and leaned in to Grayson's ear and whispered ...

"Replace them"

Mr. Alfonzo with all his strength pulled on both front and back of Grayson's underwear and skyrocketed them completely to Grayson's shoulder without ripping them.

Grayson was in immense...no unbearable pain...but with what little strengthens had left, did not make a peep. For he didn't want to make Mister Alfonzo more upset.

"Awww man almost completely ripped off, but no dice. Guess we have to do each side." Mr. Alfonzo said with a evil grin curled on his face.

Mr. Alfonzo began pulling back and forth on Grayson's underwear, front, back, front, back, front...and so in till...

Rrrrrrip!!

"Uh oh looks like the back end gave out first."

Mr. Alfonzo wrapped the back waistband to Grayson's forehead.

"Aww isn't that such a fun headband?" Mr. Alfonzo said with a laugh

"And now feels my final trick I will make these underwear..."

Mr. Alfonzo unhooked the waistband from Grayson's head...

"Disappear"

With a swift and strong yank, Mr. Alfonzo completely ripped off Grayson's baby blue boxer briefs.

"Ta-Da" Mr. Alfonzo said with a laugh as he held up Grayson's underwear as a trophy and had knocked an exposed Grayson to the floor.

Grayson groaned in pain as his ass and balls were stinging with pain, and he could feel his exposed willy being well exposed and then quickly covering himself with his hands.

"Oh come now, don't be shy, not like I haven't seen your baby pecker before!" Mr. Alfonzo said with a laugh.

Mr. Alfonzo walked behind his desk and discarded Grayson's underwear in a drawer. He then reached into another and place a pair of...

"Tighty Whities?" Grayson whined "but sir?!"

"What is it boy?" Mr. Alfonzo said with a little rage in the back of his throat

"What if the other boys see me wearing these?" Grayson said sadly

"They won't, unless you want them" Mr. Alfonzo said calmly

Grayson hung his head and began collecting his slacks and shoes. He grudgingly put on the TW's as they were a size to small and really "held" himself all together. He then put on his slacks and shoes and presented himself to Mister Alfonzo.

"I'm sorry Sir. I will do better I swear." Grayson said heart-fully

"Very good and just so we don't forget"

Mr. Alfonzo pulled on Grayson's new TW's and had them pulled over his pants and had them resting on top of his t-shirt.

"Sir!?" Grayson blurted our

"Calm down son, no one will see with your blazer on, now you know the rules...good afternoon" Mr. Alfonzo said as he continued his work.

As Grayson was heading out the door, "Also why don't we keep that in till we arrive home, shall we?" Mr. Alfonzo said with a smirk.