Willing and Wedgie

Cocky, Cautious and, Cars

It's Friday school just ended and Max is coming to pick Will up from school and hang out for the rest of the day.

Max pulls up to the school and sees his brother waiting on the curb with his Pokemon briefs stretched out his pants as long as well himself, probably the aftermath of an Atomic wedgie.

"Heh, you wanna explain the cape, Willy?" Max asked chuckling but really didn't care, he can see Will still hasn't actually picked the wedgie even though he took it off his head so it probably means he liked it.
"Not really." Will said blushing a little.
"and my name's not Willy." Will said and reached for the passenger door but it was locked.
"Hey, aren't you gonna let me in?" Will asked. And Max got an evil grin on his face
"First, say your name's Willy and put your underwear back over your head." Max ordered.
"No Way!" Will said shaking his head aggressively.

"Ok." Max said and started to pull off the curb when he heard Will yell for him to stop.
"The bus already left how am I supposed to get home?" Will asked.
"I can think of one way." Max said and gestured to the Pokemon cape coming out of Will's pants. Will thought about for a second and then reached back for his briefs and pulled them up and over his head which was pretty easy since they were already stretched out before.
"Ah!" Will said after he snapped the waistband over his forehead. Max opened the door and Will wobbled into the car sat down worsening his wedgie. But to him, it felt really good!

"And what's your name Wedgie dork?" Max said. Max's teasing wasn't always in good taste but it never came from a bad place, it was mostly for his own entertainment but there's a little part is upset his little brother he's with all the time doesn't feel confident in telling him about his love of wedgies granted he already knows but still, anyway all that's to say when Will looked absolutely pissed before saying his name was Willy wasn't what Max was going for.

Max was driving and kept looking over at an unhappy Will and started feeling a little tiny bitty guilty.
"Hey, you gonna be mad at me all day?" Max asked and Will just looked at him and huffed.
"Well, it's going to be hard for us to enjoy your surprise if you stay mad at me." Max said and Will's eyes lite up like a Christmas tree.
"A surprise?!" Will asked, max nodded.
"What is it, what is it, what is it, what is it?" Will said repeatedly as he bounced up in down in excitement still in his atomic wedgie but way too excited to remember to pretend he didn't like it.
"I can't tell you it's a surprise." Max said.
"Awww, please." Will said.
"don't worry after we stop at home real quick you'll see." Max said smugly. Will said ok and continued his adorable excited bouncing.

The two arrived home and Will ran out the car into the house and changed his clothes, which unfortunately meant taking out his atomic wedgie that he was really enjoying.

"Alright got what I needed so we can go to your surprise now." Max said as he walked to the door, Will heard ran downstairs and into the car.
"ok, so what's the surprise?!" Will asked after he and Max had only been on the road one minute.
Max chuckled.

After a few minutes of Will's constant begging, Max was getting annoyed.
"If I give you a hint will you stop begging?" Max asked annoyed.
"YES!" Will said.
"It involves one of your favorite things." Max said.
So Will's five favorite things other than family, friends, and wedgies are any vehicle like motorcycles, cars, trains, but most of all planes there his favorites then there's anime, mythology, sports, food.
So basically, "That hint's not helpful!" Will said.
"Didn't say anything about it being a helpful hint now stop asking." Max said. A few more minutes of driving they pulled up to.
"Mini golf?" Will asked confused.
"Naw it's over there." Max said and pointed at a full parking lot for.....

"GO CARTS!!!! YESSSSS!" Will said and ran into the go-cart park. Max followed.

"Hey Max, hey Will." the brothers were greeted by Max's best friend Tom.
"Sup, Tommy." Max said.
"His names not Tommy." Will said.
"Oh be quiet Willy." Max said.
"His names not Willy." Tom said.
"Yeah." Will cosigned and high fived Tom. Max rolled his eyes.

"Anyway, thanks for giving me and Will free rides all day Tom I really appreciate it." Max said.
"Uh, when did I agree to that!?" Tom asked.
"Same day I showed you these pictures of you pantsed and in a pair of tighty Whities." Max said casually as he showed Tom the pictures.
"Oh, right now I remember and look two carts just opened up."  A scared Tom said frantically and escorted the two brothers to there carts. 

"All right Will first." Tom said and buckled Will in the seat and placed a helmet on his head.
"Hmmm, something missing." Max said as he looked at Will.
"I know!" Tom said and reached down and pulled on Will's Captain America Undies and pulled them over the cart seat.
"Ohhh." Will noised.
"Much better !" Max said.
"Can I go now?" Will asked anxiously.
"Yep, all set." Tom said and Will zoomed on the track.

Max got in his cart and when he on all the safety straps and helmet tom reached down and pulled on Max's purple boxer briefs.
"TOMMY IF YOU LATCH THOSE ON THE SEAT I LATCH YOURS ON YOUR HEAD." Max growled and Tom immediately let go fearing for his life. Max picked his wedgie then started driving.

Will was having a blast driving around the track, his chair wedgie felt amazing with every turn and break the underwear shifted in different ways almost feeling like a different wedgie every time and whenever he bumped into anything he'd fly up a Little bit and land right back into his wedgie it was Paradise. Will couldn't help but moan constantly but it was fine all the car noise blocked it out.

After a good long while of racing Will and Max stopped to get some pizza at the concession stand in the raceway. While the two sat down and ate Will in another chair wedgie Max started talking about how cool the track was and Will said, "Eh, it's a little small and easy to get through." Max looked at Will and laughed.
"How can you say that you literally hit the bumpers every turn." Max said laughing not realizing that Will did it to make his wedgie worse, uh I mean better or do I, it's confusing since he likes it anyway, Will blushed and got a little mad and muttered something along the lines of "I'm better than you".

"Oh really? Ok, Willy let's race and I win I'll take you out for ice cream to cheer you up." Max said and Will just looked at him unhooked his wedgie, hopped down from his chair picked the rest out then said.
"You won't win but we can still get ice cream to cheer you up." Will said confidently. Max was shocked to see his little brother so sure. Will walked over to his cart and strapped himself in.
Max did the same.

Tom came over to start the race.
"Ready?"
"Set?"
"Go!"
*TIRES SCREECHH*

It's three laps to win and wasn't even close between the intense speed precision drifting Max had no chance. Will pulled in after winning got out of his cart through his helmet to tom and said.
"Whenever the slowpoke finishes tell him I'm waiting in the car...and my names, not Willy.

After Max finished he was shocked at how utterly awesome Will did. then after he went to the car and heard Will say "Finally, what took you so long?" with his smug proud self and the message delivered by Tom Max knew he had to remind Will of his place.

They had just finished their ice cream, Max got Mint Chocolate Chip and Will got his favorite Rocky Road. Max had told Will he was going to the bathroom but really he was buying another ice cream cone.
"Hey! No fair why do you get two?" Will whined.
" It's not for me, it's for you." Max said with a smile.
"Really?" Will asked excitedly.
"Yep, since you completely smoked me in that race..." Max started and circled Will, Will flowed with his head but stayed still.
"i thought you'd need to cool off hot stuff." Max said and pulled back Wills briefs and dropped the ice cream and let it snap back to Will's butt.
"AHHHHH, Cold! Cold! Cold cold cold!" Will said as he heled his butt and jumped up and down and squirmed as he felt the ice cream melt and the cold traveled all over his lower body. Max then pulls the briefs giving Will quite the messy wedgie. Will loved it the cool ice cream traveling down his butt made it feel like someone was rubbing his butt and it didn't take away from the snug filling he got from having cotton up his crack.
" let's go home, k?" Max said, Will too much in his pleasure simply nodded in agreement and followed as max walked to the car still holding Wills briefs up out his pants.
"Uh, Max maybe I should drive." Will said with a laugh and Max only replied by yanking Will onto his toes.
"Ow, Ow, just kidding." Will said his voice a little higher than before.