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.
"Currently, we work together, but I've known him my whole life. He grew up across the street from me. We were friends as kids, but we had very different families, which ultimately tore us apart. He's a strange dude, but we have always been very competitive. He's got to be hating the amount of attention I'm getting from you. He went ballistic at me when he got back, yesterday." Chad explained.
"So, how did you both end up here?" Alice pressed.
"Not so fast, missy! I think you owe me another dare," Chad said, running his hands up and down her thighs.
Alice pouted, making Chad laugh.
"I dare you to interrupt BJ, and get her and the guy she is talking to, to come back here," Chad said.
Alice saw BJ leaning against the bar flirting with a muscular man. He had a short buzz cut, and a perfect tan. He was hot, but looked high maintenance.
"Answer my question first. We won't be able to talk once they are here," Alice asked.
"Fine. This room is owned by the place Eric and I work for. The bar is basically a front. We use this place to earn extra. Business hasn't been great and Bobby, our boss, came up with the idea. Bobby is Bill's brother, and the bar was owned by the family. Eric and I alternate the nights we come to oversee things. But when he paraded you around earlier, I couldn't resist. I was surprised when Eric said he found someone new, who was eager to start right away. You don't seem the type to take money for this at all," Chad revealed.
If Chad knew she wasn't here by choice, he wasn't letting on to it. She nodded her head at the new info, and stood up to begin her next dare. Alice felt Chad smack her ass as she stood up, making the plug send another wave of tingles through her.
On her way to BJ, she was able to see Eric in the crowd. He was intently watching her, an angry red look on his face. Alice imagined him as a cartoon character with steam coming out of his ears.
"Hey guys!" Alice started, when she reached her destination.
"Hey! How's it going? Having fun?" BJ was bouncing up and down, as she spoke.
"Chad and I are kinda lonely in the corner over there! Come join us," Alice hoped there wouldn't be much persuading to do.
"I don't know. Bobby Joe is offering me a really good time right now. Not sure I want to pass that up," Muscle Man stated.
"Bobby Joe is amazing solo, but four hands and tits are better than two," Alice tried. She winked at BJ, hoping to get some help.
"Come on Mickey! This will be fun! Alice is already naked, so you know she's down for whatever!" BJ chimed in.
Alice needed this to work. She needed answers from Chad, and this was the only way. In an effort to seal the deal, she grabbed BJ by the waist and kissed her.
