An unfair punishment part 1

4.1K 11 9
                                    

As weeks go by, I am getting better at finishing my chores and getting fewer wedgies. Jack, realizing his scheme beginning to dwindle, decided one day he would do this to me....

"Okay, today is Thursday, and I want to have a party Saturday night! So here is your list. It's over 100 things I need you to complete by 8 pm tonight." Jack explains to me, banding me the list.

"Uh, ja- I mean, sir... I won't be able to complete all this in just 14 hours!" I begin to explain.

"Oh, and I almost forgot, you have to get out of this to begin your chores!" Jack says, turning me around, digging his hands down my pants, grabbing a handful of tighty whities (he made me switch to tighty whities to make wedgies last longer) and rockets them up my ass tugging until he successfully gets the back of my underwear under my chin, spins me around and grabs the front, tugging until he gets them over my face, sticking my arms through the leg holes, securing them tightly to my shoulders then hanging me up on the living room chandelier. "Get out of that, and you can start your chores. Fail to get out and get the punishment of a lifetime!" Jack walks away laughing.

Hours I spent trying to get down from this wedgie, the moment I was able to get down from this wedgie is the moment my undies ripped.... I was lucky enough that I was wearing these undies since yesterday because I got plenty of wedgies in them yesterday, which helped the fact that they were able to rip today. Bad news being I only have 8 hours left to complete these chores... it took 6 hours for those tighty whities to rip, and the worst part is I have to take the 10 minutes to go and put a new pair on because if im not wearing any underwear while cleaning, I get worse punishment because he likes to give my undies a good yank if he happens to walk by me while I'm cleaning. 6 hours pass, and I've managed to do 73 out of the 100+ chores on the list. That's when the doorbell rings, and I answer the door for it to be jocks and cheerleaders from high school 2 hours early for the party.

"NO WAY! HE WASN'T KIDDING, HE ACTUALLY HAS THE NERD WORKING FOR HIM!!" Brody, Jack's best friend from high school barges in as the rest follow behind. "Why don't we have some fun while we await the other guests?"

"Um, I actually have some things I need to get done, so if you'd let me get back to it, that'd be greATT!!!" I try to explain getting cut off with a sharp yank to my tighty whities from the back by Brody.

"She even still wears tighty whities!" Brody says with excitement. "Let's go give her swirlies and wedgies like we'd do every day 4th period back in high school!"

I am then dragged to the bathroom and given swirlies and wedgies for the next two hours, thus not even getting the chance to finish my chores. After the devastating 2 hours of nonstop wedgies and swirlies, Jack comes barging in saying hello to everyone and then turns to me and begins to scolled me.

"So I see you have failed to finish your chores," Jack began. "So your punishment starts here!"

Me, already on my knees in front of the toilet, underwear still in Brody's hands, Jack walks over and takes Brody's place and grabs ahold of my underwear.

"Brody, dunk her!" Jack demands.

As Brody dunks me, Jack yanks CRAZY hard on my underwear, causing me to scream and intake the nasty toilet water.

"Oh sweetheart, this is just the beginning of your night! Should have fished your chores like a good little maid." Jack says with another big yank.

~~~~~~~~~~~~~~8:15pm~~~~~~~~~~~~~~

To be continued....

You've reached the end of published parts.

⏰ Last updated: Mar 21, 2023 ⏰

Add this story to your Library to get notified about new parts!

My Highschool bully's my Boss!?Where stories live. Discover now