On Tuesday Liam and Corey awoke to find Max (Minnie) and Samuel (Sophie) in their room, who had been ordered yesterday to make sure the new girls would arrive at every class on time and acceptably dressed and groomed. So Liam’s and Corey’s day began by being shown the showers. Unlike the suites for the elites, no sissy room had an individual shower. Instead, sissies showered in communal showers that could be found in the various sissy bathrooms throughout the mansion. All their sissy rooms contained was a tiny bathroom with a toilet, a mirror, some basic toiletries, and a vanity basin. After all, sissy rooms were not meant for much more than sleeping in.
The sissy bathrooms turned out to be just as carefully designed as the rest of the mansion. The walls were covered in soft pink tile that gave the entire room an almost doll-like atmosphere. Long mirrors stretched above rows of white vanity basins, each station neatly stocked with expensive skincare products, hairdryers, incredibly soft towels, and little baskets filled with makeup remover pads and cotton swabs. Naturally, there were no urinals anywhere in sight. Only enclosed toilet stalls that couldn’t be locked and whose white doors had written on them in pink cursive script: “This stall is used by a tinkling sissy.”
The shower section itself offered even less privacy. Several large shower heads hung side by side along the wall with no dividers between them whatsoever, forcing every sissy to wash in full view of the others. But despite this deliberate humiliation, the facilities themselves were luxurious. The shower heads were massive rainfall models with adjustable temperature controls, and the provided soaps, shampoos, conditioners, shaving creams, and body washes were clearly all high-end products. Detailed murals of admittedly beautiful sissies decorated the otherwise pink walls. Tiny chastity cages, no trace of muscles on them, large pleading eyes, long flowing hair. Clearly Mercer was displaying his ideal when it came to sissies here.
They stood at the threshold between the shower room, with its tiled floor and slight downward pitch toward the drains, and the changing room beyond, lined with hooks for hanging clothes and narrow wooden benches where Max and Samuel already sat undressing. They talked casually as they removed their pajamas, which were still relatively masculine nightwear compared to the babydolls the later grades of sissies were made to wear.
Clearly Max and Samuel had already, in their short time here, lost all compunction when it came to undressing before fellow sissies, because in no time at all the only things remaining on them were their pink plastic chastity cages. And then, to both Corey’s and Liam’s surprise, they simply pulled them off.
“Woah,” Corey said.
“I thought those fucking things were locked,” Liam added.
“They are,” Max began to explain while Samuel grinned shyly at their surprise. “So you know they’re electronic, right? That means they can unlock them in the morning, and they expect us to clean our cocks, or ‘clitties.’” At this he made quotation marks in the air. “So we don’t develop a rash and whatnot.”
“But why put them on again?” Liam asked, dumbfounded. “I mean, they shock us with them, and I’m pretty sure they track us too, so couldn’t we now just... run?”
“I mean, yeah,” Max agreed. “But nobody wants to get sued for breach of contract, nobody wants to get picked up by the police and driven back to sissy school, and above all nobody wants that fuckhead Mercer to publish pics and recordings of you in revenge. He does that, you know. I say it’s best to keep your head down, try to pay off your debt before too much damage is done, and then fuck off.”
This was actually something a sissy every now and then managed. Some sissies Mercer had to let go because they slipped out of his contracts, and his system only functioned as long as it stayed within the plausible bounds of being technically voluntary and technically escapable. However, Max was also a good example of the upside these rare escapees provided. They kept many beginner sissies subdued in the hope that they too could escape their ordeal quietly and legally. Many a sissy would have made far more trouble during her time at Mercer if the possibility of a clean escape had not seemed real.
As Liam and Corey began undressing from yesterday’s school uniforms, which they had fallen asleep in, Liam discovered to his dismay that even around a day after the waxing that had removed all their body hair, there was still no sign of regrowth, something he had feverishly hoped for. After all, this would be his last week in Mercer’s fucked up fetish mansion, and he didn’t want any of his or Corey’s friends finding out about any of this.
In the meantime Liam had been working on a mental plan for how to pay back Corey’s and his gambling debts without Mercer’s money. The idea he had arrived at was that they would simply sue Mercer. It should be easy enough to win with all the abuses that took place here, no matter how wealthy Mercer was, Liam reasoned. If anything, he wondered why none of the other fuckups here had come up with this idea. Perhaps they all just enjoyed being sissy sex slaves too much, or perhaps they were all stupid or afraid. Whatever the case, he was sure his stepfather would pay for a lawyer once Liam made it clear to him just how much money they could all make with such a lawsuit.
His stepdad might not like him, but he certainly liked money, Liam was sure of that. He could also ask his mother, who was his actual biological parent, for money, but the truth was she rarely had any, and Liam couldn’t even be sure if she would be home this weekend or if she was having one of her episodes.
The communal shower room was thankfully empty this early in the morning, occupied only by the four of them. Warm water began hissing from whichever showerhead you stepped beneath as soon as it detected movement. Soon the room was pleasantly warm and filled with steam.
As Liam and Corey quickly became aware, another humiliating problem immediately presented itself. Without their cages, their cocks had gone hard almost instantly, even without any real stimulus, simply because they could and hadn’t in some time.
“I’ve got to do something about my fucking porn addiction,” Liam thought. It shouldn’t be the case that his cock couldn’t go two days without masturbation.
Corey meanwhile instinctively moved to shield his genitalia from view with his hands.
In his case, there truly had been no direct stimulus at all. The constant teasing pressure of the cages, the enforced denial, the humiliating outfits, the touching, the exposure, all of it had left him in a state of near constant arousal he could neither explain nor accept. It was a relief that Liam’s cock was also hard. At least that meant there would be no awkward questions about why Corey’s was.
Max noticed and gave an awkward little laugh as he scrubbed shampoo into his hair. “Yeah... that happens a lot at first. Your body kinda freaks out from not masturbating.”
“At first?” Liam asked suspiciously. He tried not to look, but couldn’t help noticing that neither Samuel nor Max were hard.
“Yeah,” Max answered with a small shrug as water ran down his slim shoulders. “I think after a while your body just kinda gets used to the cage.” Samuel nodded in agreement.
That, however, was not the whole truth. What none of them knew, and couldn’t know, was that the Mercer Foundation quietly introduced feminizing compounds into almost every aspect of daily life inside the mansion. The food itself was carefully controlled and supplemented. Even the water the sissies drank contained dissolved anti-androgen compounds. The skincare products distributed throughout the mansion also contained hormonal additives designed to absorb slowly through the skin over time.
Naturally, all of this made every such product far more expensive than untreated versions would have been, but Mercer regarded all this more as a personal hobby than a business.
And hobbies were allowed to be expensive.
After the shower, Max and Samuel showed them the laundry room where their clothes were usually supposed to be returned at the end of the day, though yesterday Corey and Liam had simply fallen asleep in their school uniforms. After that they were brought to the outfitting room for the sissies, where they received the outfits allotted to them for the day.
It was hard not to notice how tightly controlled all of this was. They hadn’t seen their male clothing since yesterday morning with Ashcroft, and the only clothes they would have access to until Friday were feminine ones.
Max explained, “On a normal school day we usually get like three outfits. The uniform, some normal but still girly clothes for free time, and then pajamas and babydolls for bed. When we’re well behaved we get normal but feminine clothing like we’re wearing now, but when someone misbehaves they sometimes have to wear actual sissy clothing for a day or two and...”
Liam interrupted him sharply. “Sissy clothing? I thought we’re already wearing that.” He pointed down at the new skirt he had just put on.
Samuel laughed at that and said, “No, no. This is like... normal. If an advanced sissy wears normal clothing and you don’t know she’s a sissy, you’d probably just think she’s a girly girl. But sissy clothing is the kind of stuff that lets everyone immediately see that you’re a sissy.”
“Yeah, it’s deliberately humiliating,” Max added. “Layers and layers of petticoats, lots of frills and bows, stupid fucking slogans across the chest, glitter, thigh highs, chokers that say stuff like ‘sissy slut,’ cat ears sometimes. Shit like that.”
After that they went to breakfast, where Liam and Corey once again spotted Emily up on the raised section talking to the guy they had already seen her with yesterday. Corey silently stewed over his little bowl of strawberry yogurt topped with sliced banana and granola while occasionally glancing up toward the raised section whenever he thought Emily wouldn’t notice.
After their first two hours of Theoretical Foundations of Sissification, once again taught by Headmaster Ashcroft and his impressive white beard, Liam, Corey, and Max were walking through the corridors of the large mansion on their way to one of the courtyards so they could spend their first break outside in the fresh air.
As they walked, Emily caught up to them from behind. Giggling, she said, “Oh wow, you two really look like girls from behind in your little outfits and wigs.”
Annoyingly enough, this was true.
“Oh, hey Emily,” Corey said, his mood lifting slightly despite his girlfriend seeing him like this. “This is Max, by the way,” he added, introducing their companion in his inky black wig.
“Hi, nice to meet you,” Emily said brightly. Then a mischievous smile spread across her face and she asked in mock disbelief, “But is Max really your name?”
Max looked down at his feet, clad in soft white pantyhose and black slippers with little bows over the toes, as he answered, “No, miss. It’s Minnie.”
This girl was pretty, around his age, and treated embarrassing him as the most normal and expected thing in the world. At that moment Max could have killed his sisters for what they had done to him.
As they walked out into one of the beautiful side courtyards of the mansion, Emily asked them all sorts of questions about what their time there had been like so far. Corey and Max gave embarrassed answers, while Liam said nothing and simply tried to control himself enough not to hit Emily. He couldn’t believe this chick he had gone to school with, and whom his friend now dated, had turned into such a bitch so quickly.
They wandered deeper into the little courtyard tucked beside the mansion. The spring sunlight could not fully dispel the lingering New England winter cold, however, and so the three sissies, whose slender arms were left bare by the white blouses that were part of their uniforms, soon stood around with visible goosebumps on their forearms and chattering teeth.
Finally Emily came to the one question she had actually wanted to ask them.
“So guys,” she said, using the word deliberately to get their attention. She smiled slightly as all three immediately fixed her with their stares.
“Already getting unused to being called guys?” she thought smugly.
Then she continued, “What do you actually think of all this so far? Think you’ll make it to the end of the three months?”
“No way,” Liam said immediately. “This crap’s gonna be done on the weekend. We’ll get our phones back on Friday and I’ll talk to my stepfuck about suing the shit out of Mercer. I definitely won’t be back on Monday. Corey won’t either.”
Emily was a bit disappointed by the answer. She had hoped this would go on for longer, ideally the full three months. She also disliked the promptness with which Liam had answered and the certainty he projected.
“Very unsissylike,” she thought.
“Yeah, he’s right,” Corey agreed. “I don’t think I’ll be back either.” When he saw his girlfriend’s expression fall slightly, he quickly added, “But you can still do your full three months here. Get your money. It’s only me and Liam who’ll be leaving.”
“And you?” Emily asked, turning to Max. She was asking more out of politeness than genuine interest. She didn’t know him after all.
“Oh, I’m staying,” Max said with a shrug, trying to make himself sound much more fine with his fate than he actually was. “I’m already in debt to Mercer anyway, and my parents won’t let me leave here. They think it’s ‘cute’ and ‘right for me,’ and they definitely wouldn’t help sue Mercer like your stepdad would.” He nodded toward Liam.
“And you’re fine with... I mean, look at the house sissies. Look at Jessica. You’re really fine with becoming like them?” Corey asked Max, urgency creeping into his voice.
“Look...” Max said slowly, clearly wanting the conversation to end. “It’s not like I’ve got a choice. My parents think it’s right, Mercer’s got all sorts of pictures and videos of me already, I owe him money, and my sisters, who got me into all this trouble to begin with, have blackmail shit of their own. I’m kinda trapped, and I’m trying to make the best of things, so just stop talking about it.”
He nearly shouted the last part and regretted it immediately. He had become far more emotional than he had intended to show.
“I mean, it’s fine. Stop worrying about me.”
The rest of Tuesday passed pleasantly quickly for Emily and excruciatingly slowly for the boys.
Wednesday began much the same for them, except that during breakfast Samuel reminded them that sex-ed, or “Sexual Education for Sissies” as the class’s full title was, would take place that day.
The moment he mentioned it, both Liam and Corey quietly began dreading the lesson for the rest of the day. The class had been scheduled in the fourth lesson slot from 03:30 PM to 05:30 PM before dinner. It had been placed so late strategically, so that the sissies, already exhausted from nearly a full day, would be less capable of resisting.
By the time the day’s final lesson arrived, all eight beginner sissies were exhausted.
The classroom had gone quiet in the way it always did late in the afternoon. Two sissies sat at each little desk, their shoulders slumped and their attention dulled by fatigue.
Without anyone currently in the room who could punish him, Liam saw no reason to even pretend to sit properly anymore and rested his forehead against the desk he shared with Corey, one arm folded beneath his head.
Across from them, Samuel and Max looked only slightly better. Samuel’s round glasses kept slipping down his nose whenever his head drooped, while Max absentmindedly scratched beneath the edge of his black wig.
Their wigs always became hot and itchy after an entire day of wear. Their soft pantyhose constantly rubbed infuriatingly against their shaved legs whenever they shifted in their seats. And worst of all were, of course, the cages. Tight locked plastic tubes that, after a full day of wear, settled into a constant dull pressure where every movement reminded them of their emasculating presence.
But when the classroom door finally opened, all the sissies instinctively stirred again, straightened their backs, crossed their ankles or legs, and placed their hands visibly on their desks. Even Liam made the effort. He only had to survive until Friday and wanted to avoid any further problems if he could. Especially since he planned to sue the place and didn’t know whether misbehaving would somehow weaken his case.
Corey looked lazily toward the door, expecting Doctor Keene again or, in a worst case scenario, Clara Bell.
Instead his stomach dropped.
Tiffany Mercer stepped into the room.
She wore a cream blouse tucked into a dark pencil skirt and low black heels that clicked softly against the classroom floor as she entered carrying a stack of folders against her chest. Her chestnut hair was pinned up neatly once again, and rectangular glasses rested low on her nose.
Corey immediately sat upright.
A humiliating prickling sensation spread across the back of his neck. Seeing his dad like that was somehow even more emasculating than wearing skirts himself. He wasn’t entirely sure why, but he thought it might have something to do with being confronted by the fact that if this could be done to his father, what chance did he stand?
Of course, it was also simply difficult to accept how completely the feminization had worked in just a few years.
The voice too... the voice.
That always threw him off. How was that even possible?
And then there was the near endless humiliation he would feel if any of this ever got out to people he knew. Reduced to this. Tottering around atop high heels and in a tight skirt, clitty locked away, owned and bred by Dominic Mercer. It had the potential to follow him for the rest of his life.
The thought alone made heat crawl up his neck and chest and tightened his stomach. The cage between his legs suddenly felt even tighter, as though his own body were mocking him too. In that moment he hated Dominic Mercer more than any other man on the planet.
Looking at Tiffany Mercer, Liam thought there had to be several million dollars invested in this teacher he knew to be a sissy, though unlike Emily he still didn’t know Tiffany had once been Corey’s father. Millions had to have gone into her appearance through surgeries alone.
“Insane,” he thought.
Mercer was clearly unbelievably wealthy, and this was the deranged shit he spent his money on?
The other six sissies already knew that Mrs. Mercer was Corey’s parent.
They knew because Tiffany usually couldn’t quite keep quiet about the fact that her son would be coming to this particular mansion, and once she had mentioned it the news spread through the beginner classes almost immediately.
Yet none of them had warned Corey.
Not maliciously, however.
Max especially had considered telling him several times over the last two days. But beginner sissies rotated between several instructors for sex-ed, and there had genuinely been a chance another teacher would handle today’s class instead. If that happened, Corey would never need to find out that Tiffany taught blowjob technique and sissy intimacy classes.
So none of them had said anything.
Tiffany herself knew, of course, that Corey would be in this class. Still, seeing him, in his wig, blouse, and little skirt, seated behind one of the tiny desks with his knees together like a good girl, struck her far harder than she had expected. But not wholly in a negative way. It was a striking image, her own son sissified like that. Like her. She still wasn't sure what to think of Corey's sissification yet, but seeing it already progress so far in so little time was striking.
For a moment, shame almost painfully inside her chest. This was her son! There should be no world in which she was happy for sissification… But wasn't that also the point? He was her son. Perhaps sissification was his only possible fate because of that.
Then, far away from the mansion, high above Manhattan, Dominic Mercer smiled faintly. His office monitor displayed the classroom from the security camera mounted discreetly in the back corner of the classroom near the ceiling. He leaned back comfortably in his chair.
Tiffany teaching this particular class today had not been a coincidence. He had arranged it personally. When scheduling for the week had been finalized, he had overridden the normal rotation himself and assigned Tiffany to Wednesday afternoon sexual education.
Back in the classroom, Tiffany finally composed herself enough to speak. “G-good afternoon, girls,” she began softly.
“Good afternoon, Mrs. Mercer,” came the response.
Despite Corey's fear throughout the day what sissy sex ed would actually bring with it and the initial shock of seeing Tiffany teaching it, this first hour wasn't actually too bad. Except for the tightness in his cage, the lesson produced. His questions regarding his own sexuality. Because what they did in this lesson was watch what essentially amounted to sissy pornography.
But not any sissy pornography, some taken from a website called “Sissy Social Premium,” which was the premium version of a broader website called “Sissy Social.” And this website not only belonged to Dominic Mercer but, as they found out, exclusively showed porn involving his girls and occasionally him personally.
That was what they were watching: POV videos involving Mercer, who was recording as he had sex with sissies. Now luckily these weren't sissies Corey or Liam knew or had even seen yet. The large wall-mounted screen at the front of the classroom displayed polished, professional-looking videos filmed in luxurious bedrooms, penthouses, dressing rooms, and lavish hotel suites. The camera perspective was often Dominic’s own point of view, his voice occasionally entering the audio calmly giving instructions or praise while heavily feminized sissies obeyed him eagerly on screen.
Luckily for Corey and Liam, none of the girls featured in the videos were anyone they recognized. That would have made it infinitely worse.
The room remained mostly silent except for Tiffany occasionally pausing the footage to clinically explain concepts like “sissy intimacy,” “presentation during sex,” and things of that nature.
Corey tried very hard to focus on literally anything except the videos. Unfortunately, his body was not cooperating, as the cage between his legs had grown steadily tighter throughout the lesson, pressing painfully against him every time something on screen triggered another pulse of unwanted arousal.
Why did the finished sissies seem so genuine? Was the training just so good, or had Mercer truly discovered who they were inside? Whatever the answer, the implications weren't good.
Thursday’s most memorable moment for both Liam and Corey was easily their first-ever class of what Roxanne Blake, whom they met for the first time that day, called “sissy ballet.” She called it that because, in her words, “Real ballet is fucking difficult, gals. It’s brutal on the body. Years of training, gotta have balance, stamina, and sheer damn will. Actual ballerinas are tough as hell.” She folded her muscular arms across her chest and smirked slightly. “Sissy ballet, meanwhile, is shortened, simplified, and tailored specifically for weak little sissies who would collapse crying halfway through a real ballet lesson.”
The class itself took place in one of the mansion’s mirrored dance studios. Polished wooden floors, metal barres along the walls, soft piano music emanating from a speaker, the whole nine yards. As the six other beginner sissies had been in this class for some time already, they were separated from Liam and Corey almost immediately. While the others practiced simple turns, posture drills, and basic coordinated routines, Liam and Corey were stuck doing what Roxy called “baby’s first ballet steps.”
Their outfits alone were humiliating enough.
Both had been issued pale pink wrap tops made of thin, stretchy fabric that clung tightly to their torsos and emphasized just how little upper body muscle either of them had. Beneath those they wore white beginner leotards that snapped tightly between their legs around the constant pressure of their cages. Over that came short pastel skirts that barely reached mid-thigh and fluttered embarrassingly whenever they moved. Their shaved legs were once again encased in soft white ballet tights that showed every line and shape of their legs, while soft pink ballet slippers wrapped tightly around their feet with little satin ribbons tied around their ankles.
Again and again Roxanne corrected them physically, forcing their shoulders back, adjusting the angle of their hips, repositioning their arms into softer poses.
“Posture matters,” Roxy barked while circling them like a drill instructor. “Nobody wants to look at some stiff little goblin stomping around the room. Elongate your body. Point those toes. Hips relaxed.”
They hated every second of it.
Friday was the day all sissies, like everyone everywhere, longed for. On Fridays the day ended early, with lunch at 1 PM, though of course the sissies and elites who stayed over the weekend still received dinner later in the evening. But for those elites who drove home, and those sissies who were picked up by friends or family, the day effectively ended there as well.
In truth, most sissies stayed at the mansion over the weekends. Some had simply drifted too far from their old lives already. Others no longer had anyone willing to pick them up. And Dominic disliked seeing his sissies drive themselves anyway. He thought it looked ridiculous and unfeminine. So unless a friend, relative, or partner came for them, they stayed at Mercer for the weekend.
Today, however, there was an exception. To make a good impression on Liam’s stepfather, Corey’s mother, and Emily’s parents, Dominic Mercer himself had driven up north from New York to personally bring the three teenagers home.
After lunch Liam and Corey had finally retrieved their phones, wallets, and clothes from Doctor Keene. They had changed immediately. And now the three of them stepped out into the busy parking lot outside the mansion.
Cars rolled slowly across the broad circular driveway as elites departed for the weekend. Some advanced sissies stood chatting in little groups while waiting to be collected. Others hugged goodbye with dramatic promises to text each other. A few beginners lingered awkwardly beside their bags while family members signed paperwork near the entrance.
But Corey didn’t pay attention to any of it. He felt free. He was free. No fucking weekend of his entire life had ever felt this liberating.
The spring sunlight felt warm across his skin as he stepped outside in jeans and a hoodie again, without a wig itching against his scalp or pantyhose rubbing against his shaved legs. Most importantly of all, there was no cage right now. The moment the thing had unlocked in Doctor Keene’s office bathroom earlier that morning and he’d finally removed it properly, his cock had hardened almost painfully fast from sheer relief alone. Even now, standing outside in the warm afternoon sunlight, he was still half-hard in his jeans simply because nothing was restraining him anymore.
He could walk normally again. Sit normally. Move without constantly feeling plastic pressed against the most sensitive part of his body. Every little motion no longer reminded him of what Mercer had done to him. And ahead of him lay what suddenly felt like the freest weekend of his entire life.
His phone was back in his pocket. TikTok waited for him. His PlayStation waited for him. His own bed. His friends. Real food. No lectures about posture or obedience or femininity. No stupid skirts. No teachers correcting how he sat. No wigs. No makeup. No humiliating classes. Just normal life.
Beside him Liam looked equally relieved, though far angrier underneath it all. Meanwhile Emily, who unlike them had spent the week in luxury, seemed almost strangely reluctant to leave the estate behind. Then, parked near the front steps among the expensive black vehicles, Corey spotted Dominic Mercer waiting for them.