High Stakes, Cheeky Bet

The following story was a gift I made for a secret santa event I was a part of. Enjoy.

West Feake Port. From an outsider's perspective, the city wore a veneer of charm, its facades adorned with the luster of prosperity and the promise of opportunity. Gleaming skyscrapers reached for the heavens, and meticulously manicured parks whispered of a city that had mastered the art of presentation. Yet, beneath the polished surface, West Feake Port revealed its duality, a place of greed. A place that does nothing but take and take and take some more. 

Alex Kyung found herself at one such place. Cotton Crypt. An underground gambling den filled with the city’s worst of the worst. A place where dreams go to die and people are broken. And broken was what Alex was currently feeling as she saw her last chip slip through her fingers like whispers of a lost fortune.

Now, normally, losing a game of roulette wouldn’t have mattered much to the young woman, cause she could just call up her dad and beg him to send her the money she needed and she’d have it within the hour. But not this time, because he was tired of his daughter’s entitled behavior, so he threatened to cut her off if she went over her monthly allowance of $100,000 this time. And boy did she blow through it this time.

Over 3 million lost in the span of 5 hours. But this didn’t faze her since she was confident she could win it all back easily. She just had to take out a loan with the den with their secret collateral and she’d be back in business.

And it was this arrogance that led her right back to where we last saw her. Sitting dead eyed at the table as she was over $9 million in debt with no feasible way out of this predicament that the gambling habit she picked up from her grandfather landed her. She would have lost herself in her own head if it weren’t for the shout coming from over her shoulder.

“Oh, sorry suga tits!” Exclaimed the owner of the seedy establishment, Vea Smith, but most people just call her One Eye Smith, staring with her one good eye at Alex’s rather large chest, “Looks like you’ve lost again. It’s half an hour until closing and I don’t see you winning back what you owe me anytime soon. So how about you end this rather embarrassing situation here and we just collect our collateral, hmm, doll?”

Now normally, Alex would have closed the unbuttoned top section of her shirt and gotten angry at the remarks and the way she was being talked to, but after 5+ hours of constant losing and the rather large stature of the woman talking down to her made the college student rather quiet.

“O-okay. What do I owe you? It might take a while for me to bring it to you” She sheepishly said as she pulled out her phone, intending to write down what she needed to bring to the one eyed woman to erase her debt.

“Oh, I don’t think it’ll take that long,” replied One Eye Smith as she slipped all 10 of her fingers into the back of Alex’s purple plaid skirt, “Especially since what we want is right here!”

With this, Smith’s hands rocketed towards the ceiling as soon as she had a good enough grip on the red waistband of Alex’s green high cut panties with candy cane prints.

“Eeeek! What are you doing! Don’t you know who my daddy is? He’s the assistant headmaster of Wildwood Academy! I’ll ruin you and your little “establishment” if you don’t let me down this instant!” yelled Alex, her usual gusto brought back to her with the first of what would be many tugs.

“And explain to dear old daddy how you’re $9 million in debt? I don’t think you will,” this seemed to shut up the bombastic brat as the thought of her angry dad ran through her mind, “And as for what I’m doing, it seems telling you what the collateral was slipped my mind. The collateral was you. Or more specifically, your ass. If you weren’t able to pay back the loan, we got to do whatever we wanted to your cute little ass." Each word seemed to be emphasized with a massive bounce that took Alex off her toes for a moment.

“B- but why a-a wedgie?” grunted Alex through each painful bounce, tears threatening to slip down the sides of her face.

“Because this is the Cotton Crypt!”

“Where cotton goes to die!” Roared the entire room as they all stared at the fresh meat in front of them.

“That’s right girls! Now Susan! Come help me teach our new guest a lesson” One Eye Smith shouted as a larger, more intimidating woman stood up and walked over in front of the bouncing brat, grabbing the front waistband that once sat just beneath her belly button and now reached the bottom of her huge chest.

Before Alex could protest further, the front of her panties were immediately pulled to eye level, shutting her up as she bit the inside of her lips to prevent herself from crying out in pain. This was the start of a long and brutal squeaky clean session as the candy cane prints distorted and turned to long streaks of red and white. What followed next was something Alex wished she could forget. Without speaking, the woman named Susan dropped her pants and turned around before shoving Alex’s head in between her massive and muscular behind. With this, the back waistband was passed to the bigger of the women as she pulled them above her 7 foot frame and held them above her head for what felt like an eternity. One silver thong, the only thing separating Alex’s nose from Susan’s butt.

After what felt like forever in there, Alex was finally pulled out from her fleshy prison and fell to the floor, both the cheeks on Alex’s face and the cheeks Alex’s face were just stuck between, were damp with the tears of the large titted rich girl. But as she began trying to pick her panties out of her ass, she felt 3 large, burly pairs of hands grab her waistband and leg holes and lift her entire 5’10” frame off the ground as they marched her outside, followed closely behind by the rest of the gambling den’s patrons as they brought her to a fence that faced the public street just outside the building and hung her up on one of the chain-link fence’s 7’ post before dropping her and beginning to disperse.

“Hey! Wait! Where are you guys going!” Alex shouted, “Get me down from here!”

“You’ll get down when we come back for you in the morning. Or if your undergarments rip, whichever comes first,” shrugged Smith as she pulled out a card with a number on it before handing it to Alex, “And don’t forget to come back here next week. We’ll be doing this to you once a week, every week, for the next 9 months. That’s how you’ll be paying back your debt to us.”

“Wha- 9 months! I can’t do this for 9 months!”

“Okay everyone! Shows over! The show’s over! The Cotton Crypt is now closed! You don’t have to go home, but you can’t stay here!” Susan shouted to the crowd, speaking for the first time since this whole ordeal started.

“Hey! Get back here! Someone! Let me down right now!”

As the crowd of drunks, gamblers, and bikers began to disperse, they each made sure to reach up and either grab Alex’s leg and pull down to worsen her wedgie, spank her bullied ass, or grope her massive tits as they all left to go their own directions One even stole her skirt and another unbuttoned her shirt further, leaving her black bra exposed and showing off her massive camel toe.

As the morning sun began to rise over the city of West Feake Port, it wasn’t the blare of her alarm clock that woke Alex up that morning, nor did she feel the softness of her mattress. No. What woke Alex up that morning was the honk of a car horn. As soon as she awoke, her eyes immediately started tearing up as she was reminded of the events of the previous night and the sheer pain happening between her legs. And as she looked up to see who honked at her, to her horror, she found the car stopped on the side of the road was full of her classmates from the private college she went to, Wildwood Institute.

“See! I told you it was Alex! Hey, Alex! What are you doing here, babe!” Shouted a blonde as she stuck her body out of the window.

“Please. Just help me down,” Alex weakly said as she fully let go and began crying again from the pain and embarrassment.