Seemingly, Amanda and John were a normal professional suburban couple. Nobody would guess that John had a fetish for cross-dressing. Amanda hated his fetish. Like most women. her idea of a man wasn’t one of a man wearing women’s clothing. They did have a healthy sex life occasionally role-playing, with Amanda as the dominatrix and John as the submissive. Sometimes the role-playing included a little bit of cross-dressing just to humiliate John. A little bit of role-playing had some lasting effects in that John began to practically worship Amanda’s every move. It seemed there was nothing he wouldn’t do for her.
Amanda loved keeping John in this compliant state of arousal, but at the same time hated his cross-dressing. She realized she could leverage his fetish for her own gain. It started by making John clean the whole house in a maid’s uniform while she was out with her friends. It was perfect. She didn’t have to see him cross-dressed, and came home to a spotless home. Having John clean the house that way became a weekly ritual.
The next week Amanda had her regular lunch with her girlfriends and spent the rest of the day shopping. She finally came home with a devious grin.The sound of Amanda’s heels clicking against the hardwood floor echoed through the quiet house as she entered the kitchen. Her eyes scanned the spotless countertops, the gleaming stainless steel appliances, and the freshly mopped floors. She tilted her head, a sly smile creeping across her lips. Perfect. Just the way she liked it.
She pulled out her phone and opened the message from John that he had sent her earlier while she was having lunch with the girls. There he was, standing in their living room, dressed in a French maid uniform—black dress with white lace trim, stockings, and even a little frilly headband perched on his head. His face was made up, complete with red lipstick and eyeliner. Amanda’s nose wrinkled slightly. She still wasn’t fond of this… thing of his. But she had to admit, he looked the part—and more importantly, he’d done an impeccable job cleaning the house.
“Good boy,” she muttered under her breath, slipping her phone back into her purse. She didn’t need to respond. He knew the rules: clean the house, send the photo, and make sure everything was pristine by the time she got home. No exceptions.
The thought of him alone in the house, dusting and scrubbing in that ridiculous outfit, made her chuckle softly. It was such a bizarre arrangement, but it worked. The house was always spotless now, and she hadn’t had to lift a finger. Plus, she’d canceled the maid service entirely, saving hundreds of dollars a month. All because of John’s… unique interests.
But Amanda wasn’t one to let an opportunity go to waste. If John could clean the house for free, what else could he do for her? She’d been thinking about it for weeks, ever since she stumbled upon an article online about cross-dressers making money on cam sites. At first, she’d dismissed it as something too ridiculous to consider. But then she started reading more—about how discreet these platforms were, how models could block certain geographic areas to avoid being recognized, and how much money they could make in just a few hours.
Her mind began to race. Why not? If John enjoyed dressing up so much, why shouldn’t he put that hobby to good use? After all, she had plans—new shoes, a spa day, maybe even a weekend getaway. And she wasn’t about to dip into their savings for that. Not when John could earn the extra cash himself.
Amanda poured herself a glass of wine and leaned against the counter, her thoughts crystallizing into a plan. She’d start small, of course. No need to overwhelm him right away. A few hours here and there, a modest goal of $300 per week. Enough to fund her indulgences without cutting into their budget. And if it worked, well… who knew where it might lead?
When John walked into the kitchen moments later, still in his maid outfit, Amanda raised an eyebrow. “Still dressed, I see.”
He froze, his cheeks flushing crimson. “I-I was just finishing up,” he stammered, fidgeting with the hem of his skirt. “I thought you’d like to see the house before I changed.”
She gave him a cool once-over, her expression unreadable. “It looks fine. But you can take that off now,” she said, gesturing vaguely at his outfit. “We need to talk.”
John nodded quickly, relief washing over his face as he hurried upstairs. By the time he returned, wearing sweatpants and a T-shirt, Amanda was seated at the table, her laptop open. She gestured for him to sit.
“So,” she began, tapping her nails against the table, “I’ve been thinking. You enjoy this whole… cross-dressing thing, don’t you?”
He hesitated, clearly unsure where this was going. “Um, yes. I mean, I know it’s not your—”
“Save it,” she interrupted, waving a hand dismissively. “We’re past that. What I want to know is, would you be interested in doing it more often? Maybe… in front of others?”
His eyes widened. “What do you mean?”
Amanda leaned forward, her voice dropping to a conspiratorial tone. “There’s a website called Chaturbate. It’s like a live-streaming platform where people can… perform. And apparently, cross-dressers are quite popular. You could make some decent money.”
John’s mouth fell open. “You… you want me to do that?”
“Why not?” she countered, shrugging. “You’re already dressing up. This is just taking it to the next level. Plus,” she added, her eyes glinting, “it’ll help us out financially. Think of it as… contributing to the household.”
He swallowed hard, his hands clasped tightly in his lap. “I don’t know, Amanda. That seems… risky.”
“It’s completely anonymous,” she assured him, leaning back in her chair. “You can block our area so no one local sees you. And it’s only for a few hours at a time. Honestly, it’s a win-win. You get to indulge your little hobby, and we get some extra cash. What do you say?”
John stared at her, clearly torn. On one hand, the idea of performing in front of strangers was terrifying. On the other hand… Amanda was offering him a chance to explore his fetish openly, without judgment. Well, less judgment, anyway.
“Okay,” he said finally, his voice barely above a whisper. “I’ll try it.”
Amanda smiled, satisfied. “Good. I’ll set everything up. Your first show is tomorrow night.”
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The next evening, John stood in front of the mirror in their spare bedroom, adjusting the straps on his maid uniform. His stomach churned with nerves as he applied the final touches to his makeup—a swipe of lipstick, a dab of blush. In the other room, Amanda was getting ready to watch a movie grinning knowing John was dressed like a slut getting ready to make her a few dollars.
Amanda texted from the other room, “Remember, keep it classy. No full nudity. Just tease them a bit. Make them want more.”
John texted back, though he felt anything but confident. “How long do I have to do this?”
“However long it takes to hit our goal,” she replied matter-of-factly. “Tonight, we’re aiming for $300. Once you reach that, you can log off.”
He took a deep breath, trying to calm his racing heart. “And… you’re going to be watching?"
Amanda texted, “Of course I’ll log in to check your progress. You’re now my working girl. Someone has to keep an eye on things. Now, get on the couch and start the show. Oh, and don’t forget to smile.”
As he turned on the camera and activated the stream, John felt a strange mix of anxiety and excitement coursing through him. The chat box popped up on the screen, filling with messages almost instantly.
“Wow, sexy maid!”
“Clean my house, please!”
“Those legs though…”
Amanda logged in for a moment to check on him. It looked like they loved her obedient crossdresser already. With the satisfaction she was catering to John’s fetish and earning 300 dollars without lifting a finger, she started her movie.
