Poker-Face Jenny by ToddCheese


(This story is Copyright 2005 by ToddCheese.)

Poker-Face Jenny by ToddCheese

Jenny walked slowly through the Scouts' headquarters, the heels of her pumps clicking sharply on the cement floor. Her glazed eyes traveled from one dull craft exhibit to the next: A butterfly collection, some artwork made entirely out of different kinds of leaves, a hand-carved totem pole. She was bored but tried

not to show it. Jenny felt an obligation to support local youth groups, as they were a good influence and kept the kids busy and out of trouble.

It's just that this wasn't nearly as fun as going clubbing with Ashley. Most of the booths were games aimed squarely at younger kids, not a sharply-dressed young woman in a tight skirt like herself.

The pinewood derby was easily the most interesting event. That was where the Scouts built their own model cars, carving them out of blocks of wood, strategically weighted, and sent them racing down a track to see whose design was the most aerodynamic.

Jenny covered her hand with a mouth, stifling a yawn.

"Hey lady, you bored?" came a young male voice beside her, startling her slightly.

"No, no," she apologized hastily, not wanting to appear rude. "I was just..." But she couldn't think of a good excuse.

"Hey, it's okay," said the boy, who wore thick glasses and a brown and green Scout's uniform. (And, Jenny thought, looked somehow familiar.) "This stuff is dullsville. But we've got a way more fun game going on in the back, and it's by invite only."

"Oh. And I take it I'm invited, then?" asked Jenny as the Scout led her to a door in the back and rapped on it in an elaborate series of code knocks. Cute, Jenny thought.

The door cracked open, and a fat kid's face came into view. He started to ask, "What's the pass--" but when he saw Jenny, his eyes widened and he let them in without hesitation. The room was small, and empty save for a circular table with 5 chairs situated around its circumference. Three other boys were

waiting inside: The fat kid on door duty, a redhaired lad, and one who was quite thin and noticeably taller than his peers.

"So," asked Jenny as the Fat Kid shut and locked the door. "What exactly do we have here?"

"A little side fundraiser," answered the Glasses boy, leading her to the table. "To help us earn our fundraising badges. And a lot more fun than any of the stuff going on out there."

"You got money?" Fat Kid asked abruptly. Red Hair punched him in the arm to shut him up. Jenny checked her purse. "About $40. Why?"

"For betting," answered Glasses, as Tall Kid shuffled the deck. "The game is poker. Five cards, aces high, nothing wild. Anything we win goes into the Scouts' community improvement fund."

That sounds nice, thought Jenny, but... "What if you lose?"

"It's our own money," answered Red Hair. (Where had Jenny seen these boys before?? She racked her pretty blonde head trying to recall.)

"So if we lose it comes out of our own pockets," Glasses added. "But we're counting on the generosity of our patrons to let us win at least some of it back."

"Fair enough," decided Jenny. She set her purse down under one of the chairs, and the five of them sat down to play.

Jenny's luck was spectacular. In the first hand she got two pairs, then a full house. Then three of a kind. Then an unbelievable straight flush! By that point, the Scouts were completely out of money. They looked absolutely devastated, and Jenny felt guilty.

"Well, I guess that's that," sighed Glasses.

"No money for the fundraiser," said the Tall Kid, looking crestfallen.

"And no new badge," added Red Hair miserably.

"We don't even have enough left to get ice cream with the others," said the Fat Kid. He looked like he was about to cry.

Jenny felt absolutely horrible. "Here," she said, offering some of their money back. But this only made the boys hang their heads, looking even more ashamed. Of course, Jenny realized, she had emasculated them. She'd have to let them earn it back themselves. After all, Jenny thought, it's only money.

"How about we play for it," she suggested. "I'll bet everything I've just won from you in a single hand." "Yeah, but," sniffled Fat Kid, "then we'd just be right back where we started. This whole evening will be for nothing."

Looking at their sad, innocent faces made Jenny soften even further. "Okay, tell you what," she added. "I'll even bet the $40 I have in my purse."

"You're on!" said Glasses.

Tall Kid shuffled and dealt, and this time Jenny tried to complete a hand, but her luck seemed to have suddenly run out. Two discards and none of the new draws made her hand any better. Red Hair called it, laying down his cards to reveal three of a kind. Jenny had lost.

"Time to ante up," said Glasses.

"Oh, all right," Jenny sighed. She felt a bit foolish she'd be down $40, but at least it was going for a good cause.

Only... where was the $40 she'd brought? She dug around in her purse but couldn't find it! What had happened to it?

"Is there a problem, lady?" asked Red Hair.

"Oh..." said Jenny, embarrassed. "I, um... can't seem to find the money I thought I had. B-but don't worry!" she added, not wanting to seem like a deadbeat to the nice young lads. "I'll find some way to pay you..." She wasn't sure how she'd do that, though.

"What about that necklace?" asked Glasses, pointing to the one Jenny wore around her neck.

"Oh, no, I couldn't..." said Jenny. It was one of her favorites.

"Hey, don't worry," said Fat Kid. "We'll give you a chance to win it back."

"Just like you did for us," agreed Tall Kid.

"Well... okay," said a reluctant Jenny. "But what can I bet for the next hand?"

"What else you got in your purse?" asked Red Hair.

Jenny poked through it but found little of value: Tissues, feminine pads, her subway pass, her emergency makeup kit, but nothing of value other than her cell phone. "Well... I guess I could part with this," she decided. She could always get a newer model if she lost again.

On the next hand, Jenny did great! She was dealt four clubs and picked up a fifth with a discard, making a flush! She called it. "Ha! Beat that, boys," she called triumphantly, setting the cards down.

They went around the table. Glasses had a pair of aces. Tall Kid had three jacks. Red Hair had nothing. But... Fat Kid had his own flush, in a higher suit than Jenny's! Reluctantly, Jenny handed over her phone.

"Wanna try again?" Glasses asked. "We'll bet the phone and necklace against your purse and whatever else is in it."

Jenny thought about this... She really didn't have much else of value, and she really wanted the necklace back, so she put her purse on the pile in the center of the table.

The next round brought Jenny two fives at the start, and also three diamond cards. She could go for fives, possibly a full house, or try for something better. She decided to go for another flush. It was a long shot, but would guarantee her a win, she thought. So she discarded her two fives, and drew... and got the other two! Damn! If she hadn't just thrown the first two away she would have won for sure! And she was still two cards short of the flush. But maybe next round...?

Too bad, Red Hair called it and won with two pairs. The boys grabbed her purse and began rummaging through it eagerly.

It was then that Jenny remembered her subway pass! Now she'd have to walk home! And it was 10 miles from here, at least! And her house keys were in there as well!

"Um, boys?" she said meekly. "I do kind of need my keys back."

"Sorry," said Glasses. "You bet everything in your purse. And that includes the keys."

"But I didn't think..." No, that was her problem, Jenny realized, she hadn't thought! "There must be something we can work out," she pleaded.

"Hmmmm..." Glasses thought a moment, then decided, "Swap you for your shoes."

"My shoes?" Jenny wasn't sure she liked that idea at all. She'd still have to walk all the way to the subway, now barefoot, and she wasn't sure they'd even let her ride without shoes on. The pass would be useless. "How about my shoes for the cell phone?" she asked. If she got that back, she could call someone for help.

Someone like...

"Hi, Ashley? This is Jenny! Listen, I need your help!" Jenny explained the situation as best she could,

ending with, "Just get over here, and bring some money so I can pay them off. I'll reimburse you

tomorrow, I promise!"

And so, about 20 minutes later, Ashley strode impatiently in, still in her red strapless dress from a night on the town cut short. She looked supremely annoyed at the inconvenience her blonde friend had caused her. In the meantime, at the Scouts' suggestion, Jenny had played a few more rounds to pass the time and had ended up losing the cell phone again, plus her shoes, earrings, and the ribbon she used to tie up her hair. She couldn't understand it, she just kept losing game after game, and after she'd been doing so well at first!

And what had happened to the $40 whose disappearance had gotten her into this awful mess, to begin with? If Jenny had been less trusting, she might have suspected that one of her young opponents had pilfered it from her purse while she wasn't looking. But, no, these fine young boys would never do something like that!

Jenny looked up as the brunette approached. "Ashley, thanks for com--"

Ashley rudely pushed Jenny out of the chair and sat down. "All right, let's get this over with," she said impatiently. "I have $80, against everything she lost. I win and we're squared."

"Um, Ashley?" piped in Jenny. "Don't you think you should win it back a little at a time, instead of trying to do it all at once?"

"Shut up, Jenny. It's your fault you're in this mess, so I'm in charge now, got it?" Then, to Glasses, "Deal."

He did, and Ashley growled in disgust at her lousy hand. Three discards later, she was left with a simple pair, not nearly enough to beat the full house Fat Kid brandished.

"Aww, ****!" Ashley swore. But she wasn't about to leave broke. She could win it back.

"Jenny," she ordered, "give 'em something."

"I don't HAVE anything else, Ashley!" came the protest.

"Your blouse."

"M-my blouse?!" stammered Jenny in disbelief. "B-but..."

"Give them your damn blouse, now!" snarled Ashley.

Meekly, Jenny obeyed, undoing the buttons down the front one by one, exposing a black push-up bra holding her perfectly-formed D-cup breasts. Ashley grabbed it and tossed it on the table. The Scouts managed to tear their eyes away from Jenny enough to exchange looks of incredulous disbelief at their


Jenny clasped her hands over her front as Glasses quipped, "Look, she's playing Texas Hold 'Em!" The other boys found this hysterical.

The cards were dealt, and this time Ashley knew she had it made, with a full house right off the bat. She called it, but -- how in the HELL?! -- Tall Kid had one too, with higher cards.

"Dammit!" muttered Ashley. She held out her hand to Jenny, snapped her fingers, "Skirt."

"Noooo!" whined Jenny. "You can't do this, Ashley!"

"You had your chance," the saucy brunette told her. "Now we're doing things my way."

The Scouts watched with wide, eager eyes as Jenny stood, unzipped her skirt, and stepped out of it, leaving her lower body in just a pair of red and black checkered *******.

"Oh, cute underwear," scoffed Ashley.

"Hey, look, she's got a royal flush!" teased Glasses, indicating Jenny's deeply reddening face and neck.

"Yeah, and I have a straight," added Fat Kid, "In my pants!" He was staring at Jenny's cleavage.

Another round, another loss for Ashley. Now she demanded that friend give up her bra.

"Come on, Ashley," wailed a desperate Jenny. "We've lost everything! Let's just call it quits? Please??"

"I am NOT giving up!" And to show just how serious she was, Ashley began pulling her OWN red strapless dress over her head...


"This is all your fault!" muttered Ashley as she stepped out into the night, one hand over her breasts, the other over her pubic region. Behind them, the Scouts had just finished divvying up the evening's winnings. A fight had looked to break out over Jenny's bra.

"MY fault?!" cried Jenny. "I didn't bet everything I had at once! I'm not the one who bet YOUR dress! I'm not the one who didn't wear anything underneath!"

They stood against the backside of the building, arguing. Jenny felt utterly ridiculous, standing there in just her *******. The Scouts had let her keep them, deciding they looked cute on her shapely ass... and because she'd been a good sport, letting them recoup their losses.

"Well what are we going to do now?" demanded Ashley, her clothing gone and her night ruined.

"Go home, I guess," was Jenny's only answer.

"And how exactly do you propose we do that? Like THIS?" Ashley indicated her naked body. Jenny realized Ashley had a point. Ten miles walking, and the subway would be even worse.

Both ladies jumped as a horn honked sharply and a vehicle pulled up beside them. It was Ashley's red convertible!

"Want a lift?" asked Glasses, behind the wheel. Jenny couldn't BELIEVE it when Ashley had wagered the car.

"Here, sit up front," invited Red Hair, in the passenger seat.

"No, back here, between us!" said Fat Kid, in the back with Tall. He added, "That way you won't distract the driver."

Jenny climbed in, keeping her hands over her breasts, looking morbidly embarrassed. Ashley prepared to follow.

"Sorry, lady," said Glasses. "Only room for one more."

"That would be unsafe," added Red Hair, proudly displaying his safety badge.

"And she--" Tall Kid pointed to Jenny, "--helped us earn our fund-raising badges."

"Plus now we'll get a 'Helping a Damsel in Distress' badge, too!" said Fat Kid.

"But just so there's no hard feelings," added Red Hair, "here." He tossed something at Ashley's feet.

"Consolation prize," explained Glasses. "You get to keep the cards from tonight's game. Maybe use 'em to win some clothes off somebody else. They're marked."

Glasses spun the wheel and the car pulled away into the night, leaving a furious Ashley naked and coughing in a cloud of exhaust.

"I'll get you for this, Jenny," she vowed, through clenched teeth.


(This story is Copyright 􀀁 2005 by ToddCheese.)

March 29, 2022 6:36 PM