Thank you to Sexyvibe for his awesome assistance with editing my story!
***
"Where are we going?" Chad asked Alice. He was nursing a beer, and stumbling a little, as Alice pulled him by the wrist.
"Booth. We are going to play a game," Alice replied.
"Game?" Chad questioned.
"Remember the game 'Truth or Dare'?"
"Ha, ha! Yes! It's been years!"
"It's like that. New rules though. You can order me to do anything you want, but you have to answer a question for every dare you give me," Alice explained, reaching the booth in the back.
"Who goes first?" Chad exclaimed, eager to begin.
"You," Alice whispered, coyly. She placed her hands on Chad's chest and pushed him playfully into the booth seat. She straddled his lap, and nibbled his ear flirtatiously. Alice hoped Eric was watching her toy with Chad.
"Frisky! I like it," Chad grinned, running his hands all over her naked body.
"Tell me what to do," Alice cooed in his ear.
"Behind the gaming section is a wooden box. It's all black and is filled with sex toys. I want you to get a butt plug out of it, and ask the first person you see to put it in you," Chad dared, mischievously.
"Butt plug?" Alice asked, slightly embarrassed.
"Get the purple one. Its smaller and is shaped like a mini traffic cone."
Alice nodded, and dismounted the man. She made sure to sway her hips, making her ass jiggle, as she found the box.
The case had dildos, vibrators, lubes, cuffs, cleaners, and a variety of other things Alice couldn't identify. They were all brand new and still in their cases. She found the object Chad described and looked it over. It was rubber and cone shaped, with an abrupt end so it looked like a suction cup with a trunk. She grabbed a bottle of lube, took a deep breath, and turned around.
She headed towards the blackjack table with determination. Her heels made a hard click-clack sound with every step. Alice put on her most confident grin as she neared a group of gamblers.
"Excuse me boys," Alice cleared her throat audibly. She was completely nude between her choker and heels, which caused a lot of heads to turn.
"I need some help with this," Alice pretended to be shy, and held up the toy and lube for them to see.
One man quickly stood up, proclaiming: "I'll do it!"
Alice giggled at his excitement, and noticed a few disappointed faces. She handed over both objects to a thin man with a handlebar mustache. He had muddy brown hair and eyes, and he wore a pin stripe suit. Alice wished he had a monocle to finish the ensemble.
"Please be gentle. It's my first time," Alice asked, with as much sweetness as she could muster. She bent over the blackjack table and spread her legs for the man.
There was some hooting and hollering as her new mustached friend dripped the lube onto her ass hole. Alice made "oooohh" sounds for added theatrics.
"You ready sweet girl?" Mustache Man asked.
"Yes, please!" Alice called out.
Mustache Man slowly placed the tip of the plug at her entrance. Alice tried to relax as he spun the object to gain entry. She felt her ass expand around the object, and cried out. Mustache stopped to check on her, but didn't remove the toy.
"Oohhh. Please, keep going!" Alice pleaded.
He slid the rest of the purple plug into her. She gasped loudly at the amazing surge it gave her when the bulbous end popped into her. She turned and stood, wrapping her arms around the pinstripe clad man. She thanked him, and planted a tiny kiss on his cheek.
Without another word, she sauntered back to Chad, feeling the eyes staring at her back. She had to walk carefully, for with each step she felt the object pulling and pushing. She loved the way it felt, and mentally noted to get her own.
When she reached Chad, she turned away from him to show her compliance. She bent over, with her thighs pressed together and shook her ass, the plug proudly showing above her pussy lips. She was noticeably wet, even with just a sliver of her slit showing in that position.
"Damn! Nice show!" Chad cheered at her. He reached out and pressed on the circular part of the plug. She felt her pussy gush at the sensation, but ignored it. She had a mission and couldn't let this sexy man ruin it.
"Tell me how you know Eric," Alice asked, standing up. She took the spot next to him, and put her legs on his lap.