Kyle knew this assignment from Pur’n’Kleen would be different since Daisy answered the door that first day. And not just because she was a surprisingly high-paying client. Stepping through the threshold, it was obvious the three-story brownstone hosted much more indecent soirees than its neighbors. Various sex toys lay out in plain sight, strategically placed restraints hung discreetly from the walls, an array of whips, crops and paddles hung neatly in another room, and there were assorted fetish clothes and lingerie scattered all about.
As the job progressed, he became intimately familiar with the house layout and its contents. Each floor had a different general theme, each room catered to something more specific. He guessed Daisy was a Madame, and this was confirmed a few months later when the house was no longer empty while he cleaned. Now, it was no longer just a simple cleaning job. The sounds emanating from behind closed doors kept teasing his curiosity.
Occasionally a door was left ever so slightly ajar, a tantalizing invitation for him to peek. Or he’d linger just a bit too long when cleaning a recently used room. Despite the many distractions, he tried to only let his fantasies run wild after he’d finished for the day; he needed this job after all. But today had other surprises in store for him…
“I pay you to clean, don’t I?” Daisy leaned back while spreading her legs wide in one fluid motion. It was impossible not to stare at the busty brunette’s wet pussy on full display, glistening lips clenched around a thick dildo.
She reached down to finger her clit and he felt his cock twitch as his recurring fantasy flashed through his mind: Daisy restrained to the bed as his helpless plaything while he used an assortment of toys on her, before thoroughly fucking her to his satisfaction.
She started working the dildo in and out of herself. Slowly at first, but she soon finds a rhythm and the dildo squelches frenziedly until her moans stutter into gasped breaths. Her back arches, her toes curl and the dildo squirts out of her as she cums. He can’t help but watch, mesmerized.
“Now,” she panted breathlessly, “get down and crawl over here. I need a good cleaning.”
Her request, no…command confused him. This wasn’t what Kyle had in mind, but his body seemed to understand as it complied. Crawling awkwardly towards her, he suddenly felt extremely self-conscious. What was he doing? This was ridiculous. But after months of working here, coupled with his own overactive imagination, it seemed like his tide of pent up need may finally find an outlet by burying itself to the hilt in Daisy’s warm pussy.
He stopped at the edge of the bed as the bottom of her foot planted against his face kept him from proceeding. “I want to hear you bark for me first.” Drinking in the sight of her soaked cunt, a low groan stuck in his throat as his trapped cock reminded him of how long it’s been since he last had sex. He gave a halfhearted woof through gritted teeth.
The slap was immediate; he goggled at her in stunned surprise. She grasped his face firmly with one hand, fingers digging into his cheeks. “I said bark for me like the little bitch you are, or was I unclear?” The last word’s punctuated with another swift slap which seemed to trigger a proper response out of him as he barked for her in earnest.
“Good girl,” she purred approvingly. That simple phrase was the beginning of his fall.
Kyle didn’t get to live his fantasy that day. Instead of using Daisy as he’d hoped, after he’d licked her pussy “clean” to her satisfaction, she made him clean a dozen more dildos with his mouth. She helped him clean by pushing his head down against her strap-on until he was able to take the entire length down his throat.
She made sure to show him a recording of his indiscretions afterwards. “I wonder what Pur’n’Kleen would think if they saw this? How very unprofessional…”
Over the next few weeks, his ass experienced the same treatment and he flushed with shame when she giggled mockingly while spreading his asscheeks apart afterwards, “Look at how loose your slutty boipussy’s gotten.” As weeks turned into months, Daisy steadily groomed him into her perfect maid. Soon, he was cleaning with his ass plugged while fully dressed in a french maid outfit, high heels making the silicone D-cup top he wore jiggle slightly with each step. She kept him locked in chastity and it felt like she’d locked away his whole identity, a past self he couldn’t grasp onto.
He thought of quitting so many times, but kept finding himself back at her doorstep. The pay was too good to walk away from, but more importantly, she not only held the key to his cage but had now amassed a portfolio of his sissy endeavors. Part of him dreaded seeing her, hating how she’d changed him and what unknown plans she had in store for him.
His heart thudded in nervous anticipation; today’s uniform was different. The stunning red dress had a plummeting neckline which made his cleavage look ready to spill over. Its cinched waist accentuated the waistline his corset helped him achieve before flowing out around his hips. His hair was now long enough that he used extensions rather than wearing a wig. She seemed pleased with his transformation. “Just one more thing…”
A bike was the last thing he’d expected her to bring, but as she stepped away he realized it wasn’t a normal bike – the seat had a massive built-in dildo. A wicker basket attached to the front had the words Daisy Maids emblazoned across it.
She was already squeezing lube onto the seat-dildo. “Mr. Shapiro’s a dear client of mine and he’s very eager to finally meet my cleaning slut. Why so surprised? He hand-picked you from your video selections.”