The Vegas Challenge

[ScrappyPaperDoodler]

Here's a story I've had in mind for a very long time, that I'll never actually write myself:

1. Three young (probably hot, definitely sex crazed) investment bankers make a million dollar bet to blow off some steam.
2. They take a plane to Las Vegas (or anywhere else — hell, make it Monaco if you want to be classy).
3. The goal is to have as much sex as possible, with a simple scoring system.

I was thinking it should definitely be a cast of two men and one woman with each having their own strengths and strategy. That's three POVs. Player One might started splurging on sex workers, Player Two would call a crazy ex-girlfriend and start from there, Player Three might head into suburbia and knock on doors, hoping to stumble upon horny stay at home parents and their awkward, video game obsessed (18 year old) offspring.

 

[Brandnewbuddy]

that could be fun. Especially if you go heavy on the hijinks. This version is three men but you could change one of them to a woman without much change

Like one of them thinks ALL of Nevada has legalized sex work and only realizes when he gets there that it’s not the case. So he rents a car and runs to Reno but his car breaks down…however he winds up scoring multiple times at the repair shop while he waits

One of them strikes out a few times and decides to hit the casino floor, tosses down all of his money on one spot on a roulette table…and wins. Only problem? The casino accidentally put too much in the armored car and the bank they work with is down so they can’t cover his bet till the last day of his trip. Not wanting to panic the other guests, the casino owner, who is a rather attractive woman, talks to him alone, awards him an upgraded room, and finds out why he came there. She says that it is true that escorts can’t officially work in Vegas buuuut…if he were to say…have some nonspecific charges on his hotel bill (to get the amount they would need to pay Him down) she could arrange for any woman he wants.

Guy looks at her and he can’t help but ask if that includes her…and needing to keep him from cashing out, she agrees while also offering bonuses to any of her female employees who join in.

Guy hits the suburbs trolling for housewives and bored college kids and older teens when he gets let into a very nice house with a couple of insanely gorgeous women who greet him with a kiss and then tell him to get back in the car and they’ll be along in a second. He does and they come out a second later with huge black bags. They just robbed the place and think he’s their getaway driver.

Dude peels out and they soon realize he’s not the guy so they pull guns but assure him they won’t hurt him as long as he does what they say. They stop at a motel and make him strip and hand over his phone to check for bugs and he’s clean…and also packing. Women apologize and make a deal: he lets them lie low in his hotel room while they fence their goods and not only will they let him have a cut but they’ll also fuck his brains out. Of course their other criminal contacts become involved and guy winds up getting more action of every kind.

End of the trip all three men are exhausted and well and proper fucked

 

[ScrappyPaperDoodler]

I like the idea of leaning into the hijinks and, although I've never been there myself, I think Vegas/Nevada offers a lot of opportunities as a location.

Some things I'd change/add:

I'm reconsidering money as the prize. Money comes easy to these guys, so maybe they should fight for something like a promotion instead. Then add some tragedy... It's a three-way contest to be the new VP of Whatever at Bank X with the other two promising to drop out if they were to lose the Vegas Challenge. At the end of the story, we follow the winner into their boss's plush New York office. They're about to get the job, but wait, it turns out an escort they had sex with (and were maybe a little mean to) during the trip was actually a bank employee too. Turns out, she gets the job.

Throw in a few opportunities to score high, e.g. 100 points if you can have sex with someone on the plane ride over, 200 points if you can win a sexual encounter over a hand of poker, etc.

 

[Brandnewbuddy]

I agree, the prize should be something non monetary. I also like the twist. Maybe she was on a Vegas trip and decided to pretend to be an escort so she’d have a wild story but the winner treated her as really disposable (after all he was trying to just get as many women as possible)

 

[draco519]

I think one thing that would make this whole story entirely more wholesome is the bet involves the VP of the company and two people competing for his job. The VP is either retiring early because he can or stepping down soon, right?

So the VP has two men, or three, in the competition for this job. One can be a woman. It doesn't matter.

Man 1 goes off on all the hijinks. Has all the slapstick moments reminiscent of the hangover.

The woman runs off, pretends to be an escort, has a lot of sex and fun and pregnancy scares and broken condoms and winds up handcuffed to a stripper/hooker and they're running around trying to find someone with keys to let them out.

It's all very fun and lighthearted.

Man 3? He actually runs into his college ex-girlfriend. They reconnect. She's actually wound up in Man 3's home city (he moved away, or she did and came back but hasn't seen man 3 yet.) And... they still love eachother. Life pulled them apart but here they are; like it was fate. Maybe she even has a son that looks like him and was his. She just never told him; scared of rejection or whatever.

Wrap up the week long story...

Man 1 is back with his amount of sex he's had, eager for the job.

Man 2 (or woman 1, again it doesn't matter) had fun, eager for job.

Man 3 surprises the room by quitting/accepting a lesser paid position that allows him more flexibility with his life. He doesn't want to work the 95 plus hours a week that he'd be required to put in married to a phone and emails. He wants to be married to a woman.

The VP sees this about Man 3, respects it, and offers him a massive severance to start his new life.

You get a funny story and a wholesome ending.

 

[Carnevil9]

There is no way this could be a fair competition if it involves both men and women. The women would always have a huge advantage.

I've often considered a story of two women having a blowjob contest: they go to a party or a concert or whatever (a Vegas casino would be ideal), and compete for who could swallow the most loads. They would split up, and document each conquest with a quick cell phone video. Then they meet up at midnight to see who had the most.

 

[sirhugs]

There is no way this could be a fair competition if it involves both men and women. The women would always have a huge advantage.

I've often considered a story of two women having a blowjob contest: they go to a party or a concert or whatever (a Vegas casino would be ideal), and compete for who could swallow the most loads. They would split up, and document each conquest with a quick cell phone video. Then they meet up at midnight to see who had the most.

but who was best?

 

[ScrappyPaperDoodler]

There is no way this could be a fair competition if it involves both men and women. The women would always have a huge advantage.

I've often considered a story of two women having a blowjob contest: they go to a party or a concert or whatever (a Vegas casino would be ideal), and compete for who could swallow the most loads. They would split up, and document each conquest with a quick cell phone video. Then they meet up at midnight to see who had the most.

Good point, but the woman is taking on more risk. That could be a plot point: she agreed to the bet a month ago and one week later something happens that means she's no longer on birth control. She can't back out of the bet because of pride or economic circumstance.

At first, she decides she'll try seduce women (like her male coworkers will be doing) but she quickly realises she's horrible at it.

Maybe she starts on the plane with a flight attendant and gets rejected hard. She runs into the airport bookshop, panicked, and picks up a best selling guide written by a sleazy pick up artist. She tries the strategies on women, no luck. She has an offhand conversation with some guy in the process. He's an asshole and she wonders if the book's strategies will work on him. Turns out they do and she's got him in the palm of her hand. Hijinks ensue...