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12 min read

Betting Against My Stepbrother

When Jenny Taylor bets 24 hours of doing whatever her stepbrother wants against his Ford Mustang, she'll discover that losing has consequences.
Betting Against My Stepbrother

“I swear all Giant fans are a bunch of pussies,” Ronnie downed the rest of his beer, shaking his head as the camera zoomed in on a fight that broke out as the referee called an illegal move. “I mean, did Grey have to do Stevenson dirty like that? Your quarterback had it coming.”

“Oh, piss off. I know the Giants are going to win,” Jenny snorted, huffing as she threw popcorn playfully at her stepbrother. It was another tense Superbowl season in the Green household.

This year, Ronnie and Jenny had a lot riding on whether the Giants or the Patriots came out on top.

When the game started, it was a way for the stepsiblings to connect. They bet on small things while their parents watched in amusement. Things like loose change in their pockets, an old sweater in the closet, or a Starbucks gift card that Jenny had lying around. But as the years went on, the bets became bigger and bigger and bigger.

Ronnie had just placed his Mustang up for grabs. He had purchased it less than a month ago with all the savings from his summer job. Jenny, who couldn’t think of anything to match his offer of a Mustang finally threw in an offer to do whatever Ronnie, or Ron as she liked to call him, wanted for 24 hours…if his team won.

Their mom Linda had raised an eyebrow at that. But Jenny just shrugged. It would probably be some embarrassing stuff like doing his laundry or cleaning his room, but Jenny figured, wagering 24 hours of her time against his Mustang was a fair tradeoff.

“May I remind you I’m the wide receiver at a D1 school?” Ronnie asked, “Trust me, Stevenson’s out. Stefanski can’t coach for beans and the Giants have literally zero defense. The Patriots are so totally going to win.”

Ronnie squirmed a bit in his seat, his cock stirring at the prospect of being able to command his stepsister for 24 hours.

Since they had met, Ronnie had never been able to get over Jenny’s looks. While Ronnie had taken all of puberty to grow into his lanky 6’3 frame, Jenny had been beautiful from the moment they met.

At 5’7, with a voluptuous figure and long red hair that fell down her back in shimmering waves, Jenny Taylor had turned her fair share of heads since high school. Right now, she was working at a diner. Although it didn’t pay much, Jenny always seemed to bring home a decent amount, thanks to tips.

She probably would have made a killing at Hooters, but Ronnie made sure to kick the ass of anyone who had even hinted at the suggestion. Ronnie had kicked a lot of asses.

In the kitchen, Ronnie’s dad put down the phone and called out to the kids, “Hey kiddos. I’m heading out with your mom to pick up your aunt Caroline from the airport. If you need anything, feel free to give us a call. Don’t go too crazy with your bet now, you hear?”

“We’ll be fine, dad,” Ronnie said with a wave.

“You sure you don’t want out of this bet, Jenny?” Ronnie asked as the door closed.

“I believe in the Giants with all my heart,” Jenny replied. “…and my butt, and my whole body. I believe in them. I’ll bet everything I have into this.”

“Oh? Should we take this bet upstairs then?” Ronnie challenged, arching a brow at his stepsister. He smiled mischievously. “You want to bet everything into this, right? I’ll do the same. How about every time the other team scores, the loser loses,” Ronnie paused for dramatic effect “…an item of clothing.”

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