Chapter 8
by
dikmin
Wanna bet?
"It will be funny."
"I bet it won't," said Jake, "I bet they'll laugh at his misfortune and he'll be a good sport about it. We can make plans together if I win, or Eric and I will do anything you want if I lose."
"Anything?" Janie said the word like sexual innuendo, but Jake doubted she would request anything too nasty of her brother.
"...Anything that can be completed this weekend."
"You seem so confident. Maybe he will behave with you involved, but--yeah, OK, I'll take that bet."
Jake and Eric went to Eric's room before Janie's friends arrived, as promised. Janie and her friends sounded like they were staying in the living room and kitchen to discuss plans. They were snacking here, but their original plan was to get coffee at a nearby shop soon.
Jake wondered how Janie was explaining her outfit, but he didn't try to leverage bets to find out.
Eric needed to use the bathroom not too long after he and Jake arrived in the room, so Jake checked the hallway. Nobody was in this part of the house.
As soon as Eric was out of the room, Jake heard a loud BANG from nearby. A shouting voice erupted and died in that moment, followed by a dull THUMP and two voices briefly complaining over the top of each other.
Jake ran to the hallway. One of Janie's friends had slammed Janie's door open and rushed out, running into Eric in the process and knocking both of them backwards onto the floor.
The girl was an Asian with long black hair, pale skin, and mild curves. Nothing really stood out about her slim-but-toned body, but it suited her. She was in great shape and not wearing a shirt. Some kind of makeup stained her bra and part of her shoulders, and her face looked odd with her work only partially finished.
Eric looked shocked into silence. He was waiting for her response.
A few seconds later, she began to laugh.
Everyone was gathered in the living room having a laugh. Janie and Eric had told the story of their condition with high spirits, and nobody seemed to find this chain of events unlikely. Jake pushed his luck and bet the Asian--Clarissa, California-born Chinese--that he could fix her makeup mishap. If he won, she'd go braless. Jake knew nothing about makeup and Clarissa turned out to be a lesbian who hated men more than anything, but twenty minutes later she was distracting Jake with her thin t-shirt and nobody in the group acted like it was weird.
Her makeup looked pretty fucking great now, too.
The group briefly discussed café options but they were interrupted by Clarissa.
"Eric, you know this won't end well, so keep it in your, um..." she had to stop and laugh. It sounded like genuine amusement. "Keep it in your strap, I guess."
Everyone turned to look at Eric. He had been staring at Clarissa's nipples, and now an erection was poking out from the thin crotch strap of his costume.
How does the group react? Does Jake make a bet?
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Wanna Bet?
Ever Wish You Could Win All Bets
Characters gain the ability to have people accept, lose and pay up on all bets, no matter what
Updated on Jun 4, 2026
by dikmin
Created on Feb 20, 2026
by CosmoWrite
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