Cassandra couldn’t believe she’d lost the bet, and to Tommy no less.
They’d been sitting around with the other staff after their shift had ended and the last customers at the bar had left, trading horror stories for the night. She was sure she’d be the winner and so when one of the others had suggested a little wager, she agreed.
She hadn’t counted on Tommy’s bathroom debacle with the three drunk women projectile vomiting all over him as he tried to clean up the mess.
They hadn’t set the terms of the wager up front and that had been a mistake since Tommy had said he’d collect later and she knew he would come up with some stupid idea she’d have to beg off of.
But it had turned out better than she’d thought, all he wanted her to do was to test out a new app he had been working on. It turned out to be a game and she had to admit, after playing it for a bit, she was really in to it.
She’d been playing for a few days when he’d asked her about it and she’d told him how good it was.
They’d talked for a bit and just as she was leaving, he said something that seemed a little funny at the time, “I bet you can’t play the game even more.”
Something seemed to click in her mind and she decided that she wasn’t going to lose this bet with him and so she played it even more over the next few days.
The next time they talked she gloated at him about how much she was playing his game and a predatory grin crossed his face, she was a little weirded out by it but then he said “That’s great, I bet you won’t come over to my place tonight and tell me all about it.”
She felt the click again and she responded, “Oh yea, I’ll be there, you just wait and see.”
And that’s how the last few weeks had gone. They’d talk for a bit and at the end, he’d make her a bet.
“I bet you won’t take your top off.”
“I bet you won’t go to the gym more often.”
“I bet you won’t suck my dick.”
“I bet you won’t dye your hair blonde.”
“I bet you won’t fuck me.”
“I bet you won’t wear more makeup.”
“I bet you won’t be my slutty date on Halloween.”
And so here she was, playing the game as she waited for him to pick her up and take her out for Halloween.
The game chimed a little tune as she completed another level and a small wave of pleasure washed over her. She knew she was winning the game, just like she had been winning all the bets with Tommy, and she couldn’t wait to beat him again tonight with whatever crazy bet he came up with.