This is a work of fiction, all characters are over 18. Any resemblance to real, imaginary, or fictitious people or events is a coincidence. And I am not a professional writer, so just enjoy the story with all its flaws.
***
Jordan was 19, attending a local community college and living at home. He was taking machinist, millwright, and welding classes. He'd figured that he could get a well paid skilled job that wouldn't burn him out by the time he was 30. The idea of an office job was horrifying to him. His plan was to end up with a good job and as little debt as possible when he graduated.
To save money he rode his bike to school. The cost of owning and operating a car was too much when he still had to pay for school. And it forced him to exercise twice a day, so win-win. Winter was gonna be tough with the snow and ice, but he'd walk if he had to.
Despite working towards a trade instead of some office job, he was a nerd. He played a lot of D&D and fantasy board games with his buddies. They were all geeks, without much hope of getting girlfriends. Except for Dante; he had a girlfriend, but she wasn't what you'd call 'pretty' that's for sure. But Dante did get a lot of sex, so maybe settling for less had its merits. Jordan had had a few girlfriends in high school, and he'd lost his virginity last summer before his last girlfriend went off to University. But in college he was striking out.
After midterms were over in October one of his buddies brought up the No Nut November challenge during a gaming session. It was starting real soon. A few of them tossed around the idea of doing NNN, but Jordan didn't want to do it unless there was a payoff of some sort. Why torture yourself for nothing? Not that anyone would admit to jacking off, but it was understood as kind of a given.
One of the guys said they should bet on it. Cash. Winner take all. They kicked the idea around and Alex wrote up a contract for them to sign. Alex was such a nerd. In the end they decided to make it really worth their while. They put in $500 each, which was really a financial stretch for Jordan. The jackpot was $4000 so the winner would net $3500. That money would make a huge difference to Jordan, and he figured he could easily get through the month if there was that much at stake. The rules stipulated that if there was more than one guy left at the end, the contest continued until there is only one left. Last Man Standing. If no one makes it to the end, the money gets donated to Movember and the last guy out gets the charitable donation receipt. And Rule #1 is NO LIES. If you nut out, you admit it.
Twelve days into November, Jordan was watching a hockey game on Saturday afternoon. So far, his NNN experience had been a minor inconvenience. He found that he was able to keep his libido in check without too much trouble. The money that was on the line was enough to keep him from touching himself. School, studying, gaming, and his part time job helped fill the time and keep him distracted.
His sister Cheryl, an 18 year-old High School senior, came home that day along with her two friends Katie & Alison. The girls sat down in the living room, which was weird, because they didn't like watching sports and they usually avoided Jordan as 'Cheryl's creepy older brother'. Then things got weirder. They were sitting around talking about lingerie and skinny dipping and explicit sex, right in front of him.
Jordan can't help but be distracted from the game. Katie and Alison were hot, like really hot. You might mistake them for sisters, as both were about the same height, with long brown hair done up in pony tails, nice boobs, and had similar features. His sister was quite the hottie too, although he tried hard not to notice that about her. If any of his friends ever saw him checking out his own sister he'd be ridiculed to death.
Out of the blue Cheryl asked him "So, Jordan, have you failed No-Nut-November yet?"
"What the fuck? Where did you hear about that?"
"So it's true! Yes! I KNEW it. You're playing, aren't you?"
"Aw fuck! I'm leaving."
"He IS. Whoa, you were right!" said Katie.
"Hey bro, gonna go wack off now? I can't imagine how you've actually lasted this long!" his sister jibed. She grinned evilly at him, her eyes going down to his crotch where his boner was quite apparent.
Jordan left the room under a hail of innuendo and laughter. He went to his bedroom and called Alex. Someone blabbed, he told him. He knew Alex wouldn't, as he had 3 sisters, who would all be even worse than his own.
Alex said "Oh fuck no, please don't let my sisters hear about this! Fuck, who would do that? This was supposed to be a secret, so no one would interfere with the bet."
"Maybe it was Dante?"
"Yeah Dante, it's gotta be him, the little shit. So your sister knows?"
"Yeah, her and her friends. They just started hassling me about it, right there in the living room. This was supposed to be a secret. I don't think I can put up with their crap for like another 3 weeks."
"Why, what were they saying?"
"They were going on about their favourite positions for sex and shopping at Victoria's Secret. It was like they were trying to get me hard. My balls ache enough without that, man."
"Fuck I hope my sisters don't hear about this, they'll be just as fuckin bad. Or worse.'
***
Over the next week, Cheryl invited her friends over every single day, and they spent every minute they could around him. Teasing him and taunting him. Jordan usually got home from school just before his sister, and their folks got home between 6 and 630, so on weekdays the girls had a couple of hours in which to tease him. At first it was just kidding him about the NNN contest, but then they started actively trying to make him cave. They talked about sex, very explicitly recounting their experiences, literally blow by blow job. Then they started taking off their bras when they arrived at the house, doing it right in front of him. You know, that little trick of removing a bra while leaving the shirt on. They all did it, even his sister.
