“OWIE! OWW!” A young boy winced as his white briefs shot up his butt. The young, black haired boy that was administering this wedgie merely laughed in response, not a hint of mercy dripping from his childish chortle.
Unbeknownst to him, from off the side and by a bench, the ears of a white knight for the children of the park twitched. The screams of a child in pain summoned him and from behind the small, brutish boy came the shout of the older boy that was going to save the day.
“Hey!” Gabe’s voice rang out as he stood with his arms crossed. The black haired boy, surprised, let go of the poor kid’s briefs and turned to look up at the bigger, silver haired kid. As the undies snapped against the butt of the small boy, Gabe bent down and began waving a finger in front of the tough boy’s now pouty face. “Who do you think you are?”
“I’m Xavier.” The boy said, hands behind his back. Due to being distracted, he didn’t catch the boy he was teasing sneaking off and shoving his underwear back into his shorts.
Gabe sighed. “That’s not what I meant. I mean, you can’t go around giving wedgies to other kids on the playground. You need to play nice.”
When he heard those words, Xavier rolled his eyes. He didn’t want to hear this…
“Now then,” Gabe began again, closing his eyes as he imagined the scenario he wanted to share to Xavier in his head with his hands on his knees and leaning forward, “How about you go and apologize so you both can be friends and have a nice fun time at the--?”
Gabe had only shut his eyes for a few seconds but when he opened them, Xavier wasn’t in front of him anymore. He turns a bit to see Xavier suddenly behind him, attempting to reach into the back of his pants with those curious, mischievous little fingers of his.
“Ah, ah, ah!” Gabe snapped, swinging around and turning his butt away from the kid. He had to grab Xavier’s arm to keep him from reaching forward again. “No! No more wedgies. Especially not on kids older than you. That’s just a really irresponsible and silly thing to do.”
Xavier, looking at his held arm and then back at Gabe, got teary eyed. Gabe gasped a bit, having not expected that and before he could say anything to calm the situation, Xavier burst out into a torrent of tears!
Two waterfalls jet streamed from his eyes as he screamed aloud and cried. “WAAAAAH! BIG BROOOOOOOOTHER~!” he screamed, making Gabe shrink back and then wave his hands about in a panic. He was sweating and shaking now.
“No, no, no. Please! Calm down!” Gabe asked before footsteps tramped their way up behind him. Gabe stood and shook, pupils dilating before he slowly turned and spotted the slightly taller boy with the upshooting, matching black hair.
“What’s happening here?” The scary looking older kid asked, arms crossed and face looking unamused.
“I-I uh… uhm… w-well…!” Gabe was stammering, looking back and forth between the two of them. His words didn’t come out fast enough before the crying young boy interjected once more.
“Xander! He was being mean to me!” Xavier said, pointing at Gabe, which made his heart thump.
Xander leaned forward and pressed his nose against Gabe’s. Gabe’s eyes couldn’t get any smaller. He suddenly felt like he needed to use the bathroom.
“I think I’ve seen you around here before. You’re…?” Xander muttered under his venom soaked breath.
“G-G-Gabe…!” Gabe said, gulping with a nervous smile and twiddling with his fingers. Xander looked him over, noticing how prim and proper his manner of dress was. Why was this kid wearing a tie, a dress-shirt, and slacks in the middle of a playground? Did he think he was better than them or something?
Xander, having already made up his mind about Gabe’s character, grabbed him by the shirt collar. “Okay, Mr. Too-Mature-For-Us-Business-Man…!”
“I-I assure you I have normal, casual shirts too! See, my dad--!” Gabe began before Xander planted his hand on Gabe’s head and began to push down on it, making him crumple to the grass with his eyes crossing in pain. “Urnnnnghhh…?!”
“I don’t care.” Xander said. He knew all he needed to know as far as he was concerned. “Here’s what’s going to happen. You’re gonna let my little brother give you a wedgie. Understand? You’re also going to give me your address. Don’t worry. We won’t visit your house. It’s just to make sure we know where to find you if you don’t keep coming back to the park to PLAY with us each day.”
Gabe began nodding, tearing up as the pain of Xander’s hand pressing on his head was starting to make his head go foggy. When Xander handed him a little notepad, Gabe wrote the address down without question, hoping he’d show mercy if he obeyed. He was already bent over a bit due to this position which made his butt protrude out a little though. Xavier, Xander’s little brother, had stopped crying a while back and was now licking his lips and rubbing his hands in excitement at the exposed waistband from Gabe’s pants.
With child-like glee, he gripped the white waistband of Gabe’s briefs and shot them straight up into the air, right up his butt.
“Can we talk about theeeeeeYAAAAAAAAAAAAH~!” Gabe suddenly became the park’s opera singer, screaming in a high pitched falsetto that would shatter glass due to the pain that jolted across his body thanks to this little boy’s harsh wedgie. He was far stronger than he gave him credit for, that was certain.
“What do you say?” Xavier asked, giggling to himself.
“WEDGIEEEEEEEE~!” Gabe screamed, clenching his teeth and letting his tears fall now.
“Close enough.” Xavier said, still tugging on them as he saw his big bro Xander place a finger under Gabe’s chin and help him stand up. Xavier wasn’t as tall so the wedgie wasn’t going up as high but that was okay. Xander went behind Xavier and lifted him up by his armpits. “Oh! Thanks!” He said, beaming with excitement.
“Hang on tightly to those undies, okay?” Xander said happily as he trudged backwards to a wooden fence. Gabe was forced to march backwards along with them, due to not wanting his butt torn asunder by their deepening wedgie. It didn’t matter though, because it was about to get much deeper.
Xander lifted Xavier up and helped him stretch the briefs over the top part of the fence, making sure they were securely latched on. Then he let go and watched as Gabe’s scream returned, his eyes crossing once again as more pain went up his backside from the dangling, hanging wedgie he was now trapped in.
“There. Want to add any final touches?” Xander asked.
Xavier thought it over for a bit before snapping his fingers and pantsing Gabe, leaving him dangling in his tighty whities before the entire park. Their attention had been captured now and a lot of the kids around the area were loving the show.
“Good job.” Xander said, patting his brother’s head. As the two of them left Gabe to dangle there until his undies ripped, Xander gave him one last look before adding, “See ya, tomorrow.”
Gabe stayed up there for who knows how long but eventually, his underwear ripped and he was about to slide out of them enough to fall flat on his face. With his pants gone, long taken by some random kid who thought it’d be funny to snatch them from around his ankles as he hung there, he had to tug his dress shirt down and fumble his way home, completely naked from the waist down, in the dark.
Needless to say, crawling in through the window he left open felt like something a delinquent would do and the shower he took to clean himself off was quite possibly the best shower he’d ever had in his life.
On the second day, Gabe did as he was told and arrived at the park again. This time he wasn’t wearing a dress shirt, feeling like going more casual would do well to help break the ice.
It definitely did not work.
Once he spotted Xander and Xavier headed towards him, he shrieked and tried to speak again, appealing to the sides of them that would rather be friends instead of wedgie lovers.
Instead, Xander told Gabe to bend over. Gabe did as he was told, momentarily confused, before Xavier, tugged his pants down and began slapping his butt repeatedly with his bare hand.
“AH! AOW! OWIWEEE! OOOOH!” Gabe yelped and screamed, clenching his teeth and fists as he got spanked by this little boy in front of the whole park.
“That’s what we call proper discipline.” Xander nodded as if he had said something profound.
Gabe’s spanking day at the park went on for way longer than he felt possible. Xavier’s hands started to sting and he had to switch to a tiny branch he broke off from a tree. With his butt searing red and crying out in abject pain, he was given another wedgie that turned Gabe into a stage singer once again.
He was left dangling on the same face, crying and blubbering as the two boys walked away. He couldn’t help but glance over at the pair of tighty whities that were hanging on the fence just the day before. Just like before, he eventually ripped them enough to fumble his way out and had to trudge home, half-naked, once again.
On the third day, he tried to stand tall with his hands on his hips and chin up, looking as close to cool as he possibly could. “You’re not going to make a fool out of me this time. I’m putting my foot down.”
The tactic of standing up for himself didn’t work. Within seconds, Xavier had tugged his pants down and was shoving mud down his tighty whities, making Gabe wince and fidget in extreme uncomfortable disgust.
“Uh-oh! Baby pooped himself!” Xavier said.
“Best crawl to papa if you want a change!” Xander added.
Gabe whimpered but did just that. He got on his hands and knees and began crawling around like a baby as they laughed at him.
“Was that good?” He asked. They answered, “Yes!” and then proceeded to give him another wedgie on the fence. The wait before the undies would rip and he’d be left sneaking home naked in the dark just felt longer with each day that passed him by.
Several days of tighty whities being left on that fence eventually saw him getting wedgied and pantsed, showing off a stunning surprise for Xavier and Xander.
“Are those cartoon underwear?” Xander asked.
Gabe blushed and nodded, now standing in a pair of Star Wars briefs.
“They almost look too cool for you.” Xander said, pinching Gabe’s ear. Gabe teared up a bit. Admittedly, he wanted to wear the coolest of cartoon undies he could find. He had plenty but these were the ones that made him seem less embarrassed in comparison. Fact of the matter is, all his normal tighty whities were now hanging on this fence in the park.
At the end of the day, the Star Wars briefs were added to the fence collection.
When Gabe showed up to the park again, he was pantsed and delighted the two boys with Power Rangers briefs.
“Uh-oh. We’re getting increasingly more childish as this goes on.” Xander said. Xavier merely giggled and began tugging on the briefs, almost impatiently.
“I-I don’t know if it’s really f-fair to say--!” Gabe began.
“Sing and dance!” Xavier suddenly said.
“What?!” Gabe asked, confused.
“Sing the Power Rangers theme and dance! DO IT!” Xavier snapped.
“EEP!” Gabe winced, now afraid of this younger boy. “O-Okay!” Gabe said, gulping before looking about the park. All the kids around suddenly got more noticeable.
“You heard him! Get to it!” Xander said, slapping Gabe’s butt and making him jump while rubbing his behind.
“Go Go Power Rangers~!” Gabe sang and started to shake his fists up and down.
“Shake that bubble butt!” Xaiver screamed.
Gabe flushed red and began doing just that. He turned around and shook it all about while he sang, leaving the two boys to laugh and enjoy themselves. Hopefully this put them in a good enough mood to finally be a bit more merciful.
Nope. The Power Ranger underoos dawned the fence next.
After that, the rung of undies just got more babyish. Next saw him being pantsed with Muppet Babies undies on. Gabe had no defense for this one. He merely stood there with his pants around his ankles, sucking on his lip before he got the order to dance and sing to the theme of the Muppet Babies too. He put his all into that butt dance that day, for sure.
They shouldn’t have been surprised anymore but they were. The next pair that ended up dangling from the fence were a pair of pink Disney Princess themed briefs. Gabe had grown more and more desperate and had left behind so much underwear that he was down to the humiliating dregs that he would never be caught dead in. He had no choice though. Plus, the more this happened the less calm he remained. Now his undies were basically shreds, due to tearing himself from the fence using brute force whenever he could.
Then, the day of reckoning came.
Gabe showed up at the park again but this time, he was acting weirder than usual, shuffling about and keeping his shirt tucked down. When Xavier and Xander approached him, they looked him all over as if examining him for something new.
Then they pantsed him, eliciting the loudest scream from Gabe they’d heard yet.
“NO! NOOOOOOO!” Gabe shouted, hands clamped to his blushing face. What on Earth could have been so much worse than what he was usually wearing?
A diaper! Gabe was wearing a DIAPER!
“A DIAPER! HE’S A BABY!” Xavier shouted.
“NO! No I’m not! I’m not a baby!” Gabe panicked, face super red beyond what was thought possible. He hated being in this diaper. It was comfy, sure, but it was also super distracting. Plus, it was really stretchy and covered in Sesame Street designs! He could only handle so much!
“If you’re not a baby then what’s with the diaper?” Xander asked.
“My dad noticed all my underwear was going missing and he assumed I was hiding them to cover up ‘accidents’ I was having… so this was his solution…” Gabe bit his lip. Of course this only caused the boys to laugh harder. The wedgie he got immediately after this, made his cross-eyed, teary-eyed face look even more pathetic as a result. They hung him from the fence by his stretchy diaper, delighted that their combined efforts got this boy reduced from briefs to huggies.
As Xavier snapped a picture to celebrate this accomplishment, Xander grabbed Gabe’s legs and poked his head through them with a delighted smile. “Haha! Baby Gabey got put back into diapers!”
Gabe could only cry and look down at the young boy he scolded all those days ago as his humiliation was being preserved. He couldn’t do anything as they made that proclamation and even had to stomach them later tying a bib around his neck and forcefully spoonfeeding him babyfood while he was up there. Xander had to hold Xavier up to Gabe to get him to do it and yet Gabe still looked like the youngest of the three.
When Gabe was left there, that day, Gabe found that for the first time, he couldn’t get off by waiting for the underwear to rip. These were stretchy diapers.
He twitched and winced, realizing he had to go potty. If he came home in a wet diaper, that would just confirm that his dad had been right about accidents!
It took some time but Gabe eventually managed to unhook himself.
Unfortunately, the impact he made from hitting the ground, sent a sharp pain through him that signaled his bladder that it was waterfall time.
Gabe sat there with wide eyes as he christened his diaper in the middle of the park at night.
Great. Now he was stuck in these things for who knows how long…!
That kid he rescued had better be grateful…
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I absolutely loved the gradual regression. I'm not sure if ive ever seen you do gradual regression like this before but i truly enjoyed it. Watching him go from plain briefs and descend to disney princess briefs was fun enough but diapers took the cake! And to top things off since he's going home wet he may end up stuck in diapers which will be a cute juxtaposition to his super mature demeanor. My only question is how many pairs of big boy undies does he even have left after all of that wear and tear lol, poor gabe.
I absolutely loved the gradual regression. I'm not sure if ive ever seen you do gradual regression l
Youre welcome! I can tell.you worked hard. The way you described every wedgie and his change in attitude as time went on and his underwear only got more and more embarassing with every pair destroyed truly drew me in. I'm a huge fan of gradual descent and slow but sure humiliation so this art and story may be one of my favorites by you yet.
Youre welcome! I can tell.you worked hard. The way you described every wedgie and his change in atti
Poor little Gabe. Xander and Xavier need to be given a swift, hard kick in the nards, their tiny, tiny nards. There are a few solutions for Gabe to avoid his daily wedgies at the hands of these two, he could tell his parents what is happening and why he keeps going through underwear ( and pants) if the situation escalates/goes on for too long or to prevent any escalation. If he doesn't what to get his parents involved, he could just go commando so he can't get a wedgie and glue a large leaf to his bubble butt and a smaller leaf on his junk so that he doesn't show off his boyhood to onlookers. Or he could meet up with them but(t) be butt naked to challenge them if he's feeling bold enough, or wearing just a robe until he's with them and take it off then if he isn't daring enough to walk all the way to the park shamelessly strutting and showing off his birthday suit.
Poor little Gabe. Xander and Xavier need to be given a swift, hard kick in the nards, their tiny, ti
