Miss Agatha's School for Lost Sissies: Chapter 1 (Patreon)

DISCLAIMER: This story contains diaper usage, public humiliation, masturbation/diaper sex, crossdressing, hypnosis, diaper filling, and other ABDL themes. I hope you enjoy!

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“There’s no way he’s in here,” thought private detective, Matt Colson, as he stared down at the address on his phone in utter disbelief. It had been nearly a week since his best friend, Jesse Jennings, had gone missing. Given that was the first time that he was required to track down someone he knew personally, he felt an understandable urgency to scrape up any leads he could get his hands on. Sadly, after days of leaning on contacts and digging through dumpsters, he was beginning to lose hope. That was until he scored a tip that led him to where he was now, though he wasn’t feeling particularly optimistic as he stared at the entrance of a large pink castle with pearly white gates guarding its exterior. In front of the scenic estate was a sign painted in cutesy, pastel colors that read, “Miss Agatha’s School for Lost Sis-”, with foliage obstructing the final word. Matt could only assume that was the conclusion of the manor’s long title was “Sisters.” Needless to say, it wasn’t exactly the type of place he’d ever imagined Jesse would end up at.

Jesse was the kind of person who made friends with everyone he met. He had been the running back for his high school football team and an all-star performer in show choir while also maintaining a perfect 4.0-grade point average. Meanwhile, Matt couldn’t have been more opposite. With few friends to speak of and middle grades at best, he was comfortable floating through school as under the radar as possible.

And yet, somehow, despite the massive differences in their personalities, Matt and Jesse had been practically inseparable from K through 12 and managed to stay in touch in the years following their time as students together, with Jesse going into sports journalism while Matt followed in his father’s footsteps and became a PI. That all changed recently, though, when Jesse ended up missing their usual Friday night at the local pub. Matt initially thought nothing of it. It wasn’t the first time that Jesse had ditched him for some one-night stand. It wasn’t until two days later when Jesse’s boss gave Matt a call to see if he knew why Jesse wasn’t answering his phone that Matt realized this was more than just a casual disappearance.

*BZZZZZZZ!*

An old, loud buzzer greeted Matt as he approached the comm box next to the estate’s grand entrance. Normally, he took his time to scope out the scene before moving in for some one-on-one interviews. However, enough time had already been wasted, causing him to make a brash and impatient decision.

“Hello, sir or madam. Please state your purpose here today and someone will assist you shortly,” said an automated system, catching Matt off-guard as he lifted an eyebrow at the robotic vocals. Pressing the talk button, he quickly considered which role he should play today, improvising a story he’d gone with several times, “Hi there, I’m supposed to be doing a writeup today for the local paper. My boss told me I should be expected.” The second sentence was the kicker, acting as a secondary authority figure to pressure whatever minimum wage pencil pusher answered the call.

Much to Matt’s surprise, when a human voice finally came through the grainy speaker, it wasn’t a stuttery mess attempting to explain that he wasn’t on whatever list they had in front of them. “Oh yes, Mr. Greene, we’ve been expecting you,” said the soft, feminine voice moments before the shimmering gate began to open. He wasn’t certain who this Mr. Greene was but he made sure to silently thank them for making his job a million times easier.

Making his way up the winding path, Matt soon arrived at the top of the hillside where the gaudy pink castle awaited his arrival. It looked like something straight out of a fairy tale picture book. From the stained glass windows to the well-maintained lawn and dazzling flora, it was the kind of sight that would make any little girl’s heart flutter. Matt, tragically, was not a little girl, and thus found little enjoyment in the rare sights he was seeing.

Perhaps the most shocking thing of all, though, was the massive moat that curved around the front of the Victorian-style mansion with a single bridge plugging up the only entrance to Miss Agatha’s feminine kingdom. He supposed it added to the overall aesthetic even if it was overkill after investing in the metal fence. He was not a fan of how long the bridge took to lower, the medieval-era feature forcing him to wait nearly five minutes for the heavy wooden door to be lowered into position.

Once he was finally able to cross into the castle’s ostentatious entrance, Matt was instantly greeted by a tall woman who looked like she was edging into her late 20s wearing a short, frilly blue dress that barely covered the length of her panties. “The School of Lost Sisters must be run by a bunch of pervs,” was the first thought that came to Matt’s head as he stared at the young woman’s ridiculous and revealing attire. Since he was uncertain if the rest of the faculty dressed in a similar fashion, he decided to keep his mouth shut even if the small boner in his pants had much more to say on the subject.

“Hi there, mister! My name’s Kimmy, and I’ll be your escort today as you tour the grounds. Please don’t hesitate to ask if you have any questions,” said Kimmy in a chipper, yet deep voice. It would sound almost sultry if she didn’t speak in such an excitable, immature manner, “Now then, you can follow me to the front office so that we can sort out a guest badge for you.”

Following closely behind Kimmy, Matt was led through a series of winding corridors, causing him to become disoriented and lose track of which way he’d entered. “I’m impressed you know how to navigate this place. I've been in corn mazes less complicated,” he said, letting his rural roots slip for a brief moment.

“You get used to it after you spend enough time running around here. Trust me, though, it is quite the learning curve,” said Kimmy, spinning around and walking backward as she chatted with Matt. All the while, she curiously looked him up and down as if were some alien species, “By the way, aren’t you supposed to have a camera? The memo mentioned you were hoping for some exclusive shots of the facility.”

Stealing his composure with the skills of a ten-year professional, Matt was so used to fielding questions he could lie with almost perfect ease. “Oh, those big cameras are a hassle. Most photographers use phones now,” he said, having no clue if what he said was even remotely true as he pulled out his smartphone and flashed it to Kimmy.

*SNATCH!*

Suddenly, Matt was stopped in his tracks as Kimmy stole the cell phone right out of his hand. “You were informed in the email that cellular devices were not permitted on our premises,” she said sternly, the cheeriness in her voice disappearing in a split second.

Clenching his jaw tight, Matt merely sighed and smiled at the young woman as he held up his hands. “Apologies. I wasn’t thinking when I left for the assignment. I’m so used to my phone being my camera at this point that I didn’t think anything of it,” he said, wanting to defuse the situation as efficiently as possible. After all, it wasn’t like he cared much about the phone in Kimmy’s hand when he had a back-up tucked under his crew sock, “You wouldn’t happen to know if there’s a camera I could borrow. I promise to ensure its safe return.”

Flipping back to her amicable persona, Kimmy smiled warmly at Matt as she took his hand in hers and pulled him forward. “Absolutely! I’ll make sure you get a suitable replacement after you’re all signed in,” she said, leading him down another long and twisty hallway until they arrived at a set of golden double doors. Behind them was a standing-looking office with cubicles and computer desks scattered throughout the wide space, “Please allow me to welcome you to our front office. It’s nothing compared to what’s in store but we can consider this your first stop on the tour.”

Matt’s eyes were instantly drawn to the enormous portrait of “Miss Agatha Thronebrush,” the founder of the i. She was a stunning, middle-aged beauty with hair that was such a deep shade of violet that it was nearly black. It was almost hypnotic the way his gaze traced the red dress that hugged her curvaceous body. Most alluring of all was the mountainous cleavage that her tight dress produced, increasing the bust over her already ample bosom.

“Quite a woman, isn’t she?” said Kimmy, her words startling Matt back to reality. He blushed ever so slightly as he, uncertain of how long he’d be staring at Miss Agatha’s painting, “No need to be embarrassed, Mr. Greene. I promise you’re not the first to be lost in her beauty. However, we have a schedule to maintain, so I must insist we keep moving.” Taking Matt’s hand once again, she pulled him forward, silently snickering as she caught him sneaking one last look at the enchanting portrait.

Waltzing through the heart of the office in lockstep with Kimmy, Matt’s nose was met with the overpowering aroma of flowery perfume, making him want to gag. He struggled to hold down his lunch as he strode through the sickeningly pink office space, finding there wasn’t another man anywhere to be seen. Just more women dressed similarly to Kimmy’s hyper-feminine ensemble, though in a variety of colors, styles, and fabrics. It was like he’d fallen headfirst into a land ruled by the Stepford Wives. Worst of all, every cubicle he passed came with a new set of eyes to gawk at him with, no doubt due to how rare it must’ve been for a member of the opposite sex to be in their presence. Having never been super confident around women in general, his hands quickly found their way into his pockets as a cacophony of whispers and soft giggles echoed all around him.

Mercifully, Matt and Kimmy soon arrived at one of the cubicles and proceeded to spend the next ten or so minutes going over the rules for his visit. Other than the rule about phones, he was forbidden from fraternizing with the students, couldn’t go anywhere without Kimmy escorting him, and would only be given two hours to tour the grounds. He cursed his luck, knowing how much harder it was going to be with Kimmy looming over him in such a short timeframe He’d have to find a way to ditch her at some point if he was going to search for anyone who might know why Jesse was here and where he might be headed.

Beyond that, the rest of Kimmy’s spiel was about the purpose of the school and her duties as a member of the faculty. This allowed Matt the perfect opportunity to take in more of his surroundings as he couldn’t care less about the mission of some ritzy, all-girl school. Kimmy was fairly tidy with how she kept her cubicle but there were still a few key artifacts that he made sure to take note of. For one thing, it was odd that there wasn’t a single photo or picture frame anywhere on her desk. And while there were several explanations for why that might be the case, it didn’t explain the second, much bigger red flag. Why did she have a stack of papers listing several male names? Certainly, for a school consisting of only women in both its staff and students, it was out of place, to say the least. He strained his vision to see if he could spot “Jesse Jennings” among the list of names but was unable to make out more than a third of the list due to how small the text was.

“Mr. Greene?” said Kimmy, snapping Matt to attention, “Your badge?”

Looking down at Kimmy’s hand, Matt let out a nervous laugh as he accepted the laminated badge from Kimmy’s hand. There was no name on the badge, only the word “Visitor” written in bold pink to match everything else in this place. “Thanks. We’re good to go, then?”

“Almost! One last thing before we can head off,” said Kimmy, reaching into a manila envelope and pulling out a stack of papers before placing them in front of Matt, “Merely a formality. I’m sure you’re used to NDAs in your line of work. We, of course, strive to maintain our privacy and security.”

Matt cautiously picked up the first page of the contract he was now expected to sign. Contrary to Kimmy’s assertion, this wasn’t something he was used to as a private eye, though she didn’t need to know that. Skipping most of the pages, he flipped to the final sheet to print and sign his name, making sure to write as illegibly as possible just in case Kimmy knew whatever this Mr. Greene guy’s first name was supposed to be

Thankfully, Kimmy didn’t say anything as she looked over his signature to make sure all i’s were dotted and t’s were crossed. “Perfect! We’re all set!” she said, tucking the contract back into the folder and securing it away on her desk, “Ooooh! Let me show you to the observation deck while we’re here! Trust me, you can’t ask for a better view of the entire school.” Guiding Matt back through the office, she detoured away from where they entered and toward a small, wooden door that looked out of place in relation to the grand entrances and sterile doorways he’d seen up to this point.

Matt was forced to duck down as he stepped out onto a small balcony with a stone railing. True to Kimmy’s word, it was quite the sight to behold as he gazed upon two dozen acres that made up the luxury estate. Though, to call it an estate felt like an understatement. In reality, the school may as well have been its own private town, complete with shops, restaurants, and plenty of activities to choose from. All of which was decorated to match the pastel pink castle at its heart. “Woah!” he muttered, losing his composure momentarily as he took in the unparalleled extravagance. Catching his split-second break in character, he immediately went to recover, “I mean, what a view. That Miss Agatha sure put together one heck of a place.”

“Hehe! No arguments here! We all owe so much to Miss Agatha and her kindness,” said Kimmy, entering behind Matt and taking a deep breath through her nose as she soaked in the view from her favorite hidden spot, “It feels like only yesterday that I was a young, budding sissy looking for any sort of guidance. She’s helped me in ways I could never even begin to make up for.”

Nodding his head and smiling as he passively listened to Kimmy, Matt froze as he focused on one aspect of Kimmy’s statement, his brain struggling to piece together the very obvious puzzle. “I’m sorry, I must’ve misheard you but…did you say you’re a sissy?”

“Pfffffft! Well, of course, I am! Would be a little odd not to be a sissy in the School for Lost Sissies, after all,” said Kimmy, elbowing Matt at what she assumed had to be an obvious joke. Little did she know that as Matt anxiously laughed along next to her, his "joke" was anything but.

TO BE CONTINUED…