While thinking of what to do with Jacob from that point, Principal Sloan looked out the window and saw the flagpole that stood in the courtyard in front of the school. That long metal pole face him an idea, an awful, wonderful idea. "Ringo! Rocco! Get him up! He's going up the flagpole!" He said.
With that, the two burly prefects hoisted the wedgied boy up to his feet and marched him out into the halls. While still in the vicious atomic wedgie, he couldn't see where he was going, but he heard the whole thing, and he knew where he was going. He also noticed that the halls were becoming more and more crowded by the second. It seems that the entire student body wanted to see the boy's humiliating wedgie up close.
Finally, the large group got outside and Ringo and Rocco went up to the flagpole with Jacob firmly in their grip. When they got to the long pole, Ringo went up to it to take down the normal flag of their school's crest and freed the clasp in preparation for Jacob's journey up. Rocco was holding said wedgied boy in his grip in on hand and in the other, he was stripping the underwear off of Jacob's head.
Now that he could see, Jacob began to get weak in the knees. The flagpole went up to twenty feet in the air. He couldn't imagine going up that high.
"I wouldn't worry, Jacob," Principal Sloan said, as if he could read Jacob's mind. "You won;t be going all the way up. Just high enough for you to feel gravity's full affect on your ass crack." He laughed and the other student laughed along with him.
Now that the flagpole's clasp was freed and the atomic wedgie was undone, Ringo and Rocco proceeded to hook Jacob in to the clasp by hooking the clasp in between the leg holes. When he was all hooked in, Ringo and Rocco both smacked him on the butt and went to the rope. Jacob was nervous yet excited. He had always dreamed of getting a wedgie such as the flagpole wedgie. And now, the day has come. His legs turned to jelly at the thought of going up the pole by his undies. Well, he was going to get what he wanted. "Oh thank you, devil lady for this opportunity! I'll never regret this decision ever!" he prayed silently.
Then, it happened.
"Alright boys, hoist him up!" Sloan said, and the two strong prefects heaved at the rope. And Jacob's undies went up his butt once again.
His crack was once again filled to the brim with stretched and ruined cotton. He exclaimed and moaned as the fabric sliced into his now delicate behind. He clenched his legs to help slow down the wedgie to no avail. The more they heaved, the higher the underpants went. Higher and deeper into the poor boy's butt the undies went and the more time went by, the higher Jacob himself went. His was hoisted off the ground almost instantaneously.
After his feet left the ground, he was actually hanging by his underwear, a feat that he achieved only a few times by himself, and none of them were this humiliating or pleasurable. He was loving every bit of this wedgie, and the school could tell, because his pants were still at his ankles and he was sporting another boner. The students and teachers watching were taking pictures and videos with their phones to send over the internet later that day no doubt.
As Jacob hung there, gravity took its effect on him and Jacob sunk into the underwear very deep. The stretched out front of the underwear was almost unnoticeable because Jacob leaned into the front as he went up higher and higher up the pole. The length of the back end of the underpants was almost twice as big as when he was given the atomic wedgie before. From him leaning to the front, he accidentally exposed his plumber's crack to the student body as well. He blushed at his exposure to the other students.
When Jacob reached five feet off of the ground, Ringo and Rocco were signaled to stop pulling, so they did. Then, they secured the rope to the pole to keep him in place. Jacob's flagpole wedgie was complete as he swayed in the wind by his tighty whities. Principal Sloan had a nice long laugh of accomplishment along with the rest of the audience. "Alright, lets get back to class everyone. Let this be a lesson to him for revealing his waistband to a crowd of bloodthirsty wedgie enthusiasts." With that, he and everyone else began to leave.
Jacob snapped out of his wedgie high just long enough to realize that he was all alone now. "Hey, what! Who's gonna get me down?" he asked the people who were retreating into the school. "Hello? A little help here, please? My legs are going numb and my butt really hurts!" But his pleas were let unheard and he was alone now. He sighed. "Well, at least I'm not that high off of the ground, so when my undies rip i won't fall that far." he chuckled to himself.
Jacob hung on the flagpole for hours until his underwear finally ripped clean off. He was amazed at how far they stretched before they finally gave in. He then proceeded to walk home, and by "walk" he really means "waddle," holding his aching booty in his hands.
What happens next?
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