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The Sissy Maid Bet
It's just a little wager. What harm could it do?
It's easy to be bored when you're a beautiful young woman with money to burn, but the millionaire heiresses Miranda and Jennifer have found a new game to keep themselves amused: betting on human beings. With a hundred grand on the table, Miranda gives Jennifer a sexy wager she can’t possibly refuse – in just twenty-four hours, she has to turn their hot alpha-male waiter Sam into a passable sissy girl.
Getting him to the apartment is the easy part. Convincing him to go along with being her chastity-locked maid is a little tougher. When he realises that it’s not another woman he has to convince but Miranda’s hot male friend, however – a man who is looking for a slutty maid all of his own – Sam has to decide just how far he’s willing to go to earn his money.
Will this sissy’s oral skills be able to convince them he’s a real woman – and even if he does, will Miranda and Jennifer ever let him go back to his normal life?
This story contains themes of sissification, forced bi, and male chastity.
Extract
‘Good boy,’ I said. ‘Or girl, I suppose. How does that make you feel, being my good girl?’
‘I… I don’t know,’ he stammered. ‘OK, I guess.’
‘You guess? You’re going to have to do better than that to get your money.’
‘Sorry,’ he said. ‘I like it. It’s weird, but…’ His voice faded away, leaving the rest of the sentence unsaid. It didn’t matter. I knew exactly what was going through his mind.
‘Good,’ I said. ‘The rules, then. For tonight, you’re Samantha. You’re my maid, newly hired. You’ll do exactly as I ask you to, and you’ll try and be as feminine as possible. I’ll cover for you as much as I can, but at the end of the day it’s down to you: if you fuck this up, it’s you who loses out. Do you understand?’
‘Yeah,’ he nodded. ‘I think so.’
‘Tut tut,’ I said playfully. ‘I don’t think that’s how a maid would address her employer, do you?’
‘Ma’am?’ he suggested.
‘Mistress, I think.’ A faint blush began to cross his face: subtle, but strong enough that it showed even through Olivia’s makeover. ‘Unless you have a problem with that, of course?’
‘No,’ he said. ‘If you say so.’
‘No, what?’
‘No Mistress.’ It wasn’t strictly necessary for the bet, but I loved the feeling of power I got from humiliating him like that. He must have known that it was going to be an embarrassing evening, but I doubt he had any idea of what I’d do to him – and, more to the point, what I still had planned.
It's easy to be bored when you're a beautiful young woman with money to burn, but the millionaire heiresses Miranda and Jennifer have found a new game to keep themselves amused: betting on human beings. With a hundred grand on the table, Miranda gives Jennifer a sexy wager she can’t possibly refuse – in just twenty-four hours, she has to turn their hot alpha-male waiter Sam into a passable sissy girl.
Getting him to the apartment is the easy part. Convincing him to go along with being her chastity-locked maid is a little tougher. When he realises that it’s not another woman he has to convince but Miranda’s hot male friend, however – a man who is looking for a slutty maid all of his own – Sam has to decide just how far he’s willing to go to earn his money.
Will this sissy’s oral skills be able to convince them he’s a real woman – and even if he does, will Miranda and Jennifer ever let him go back to his normal life?
This story contains themes of sissification, forced bi, and male chastity.
Extract
‘Good boy,’ I said. ‘Or girl, I suppose. How does that make you feel, being my good girl?’
‘I… I don’t know,’ he stammered. ‘OK, I guess.’
‘You guess? You’re going to have to do better than that to get your money.’
‘Sorry,’ he said. ‘I like it. It’s weird, but…’ His voice faded away, leaving the rest of the sentence unsaid. It didn’t matter. I knew exactly what was going through his mind.
‘Good,’ I said. ‘The rules, then. For tonight, you’re Samantha. You’re my maid, newly hired. You’ll do exactly as I ask you to, and you’ll try and be as feminine as possible. I’ll cover for you as much as I can, but at the end of the day it’s down to you: if you fuck this up, it’s you who loses out. Do you understand?’
‘Yeah,’ he nodded. ‘I think so.’
‘Tut tut,’ I said playfully. ‘I don’t think that’s how a maid would address her employer, do you?’
‘Ma’am?’ he suggested.
‘Mistress, I think.’ A faint blush began to cross his face: subtle, but strong enough that it showed even through Olivia’s makeover. ‘Unless you have a problem with that, of course?’
‘No,’ he said. ‘If you say so.’
‘No, what?’
‘No Mistress.’ It wasn’t strictly necessary for the bet, but I loved the feeling of power I got from humiliating him like that. He must have known that it was going to be an embarrassing evening, but I doubt he had any idea of what I’d do to him – and, more to the point, what I still had planned.
20 pages, Kindle Edition
First published October 3, 2014
3 people are currently reading
22 people want to read
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Displaying 1 - 4 of 4 reviews
January 19, 2016
A really well written story about a young waiter willing to let a wealthy young woman his age transform him into a sexy French maid to win a bet against another wealthy young woman his age. If he avoids detection as a male, he stands to win £20,000.
Will he win his share of the bet? What will he have to do to win? Will he like it? Will he ... Read this amazing book to find out! A must read for those who like voluntary feminization, female domination, whimsical changes to another person's life, and other very hot sexy kinky fun.
Will he win his share of the bet? What will he have to do to win? Will he like it? Will he ... Read this amazing book to find out! A must read for those who like voluntary feminization, female domination, whimsical changes to another person's life, and other very hot sexy kinky fun.
February 8, 2016
Two wealthy young women brighten up their lives with bets. Miranda challenges to Jennifer to make Sam their waiter, look like a convincing woman by 8PM the next day. Not being a well off man, Sam decides he has to do it for the money Jennifer offers.
The story us fun, though Sam's hopes of an end are not realised as he is trapped in his new life.
The story us fun, though Sam's hopes of an end are not realised as he is trapped in his new life.
December 23, 2025
Short story that basically proves (at least in a fictional way) that everyone has a price. Waiter Sam is offered 20,ooo pounds if he allows himself to be transformed into a sext girl. And if he fools a 3rd party and obeys every demand. Is that enough pounds for his to acced to the most humiliation ever? How much will it take? That’s the story…
July 24, 2020
A Bet Is A Bet!
A young waiter is offered money in a silly way, and becomes a pawn! He is professionally turned into a woman. The she must pass a test. Success! The best is won and fashionably so. More to come, I am sure.
A young waiter is offered money in a silly way, and becomes a pawn! He is professionally turned into a woman. The she must pass a test. Success! The best is won and fashionably so. More to come, I am sure.
Displaying 1 - 4 of 4 reviews