Dom’s Sissies Pt. 5: A Day in Sissy School

𝐌𝐨𝐧𝐝𝐚𝐲

𝐅𝐢𝐫𝐬𝐭 𝐋𝐞𝐬𝐬𝐨𝐧 - “𝐅𝐞𝐦𝐢𝐧𝐢𝐧𝐞 𝐅𝐚𝐬𝐡𝐢𝐨𝐧, 𝐏𝐫𝐞𝐬𝐞𝐧𝐭𝐚𝐭𝐢𝐨𝐧 & 𝐃𝐞𝐩𝐨𝐫𝐭𝐦𝐞𝐧𝐭”

(𝟎𝟖:𝟎𝟎 𝐀𝐌 - 𝟏𝟎:𝟎𝟎 𝐀𝐌)

Ashcroft opened the door, and a small, pretty woman looked at them from inside the room. That she was pretty immediately caused Corey’s light-brown wig to itch a bit more intensely. In fact, he felt everything very intensely right now. The soft pantyhose rubbing across his newly hairless legs, coupled with his cock being so cruelly prevented from hardening in its pink hard plastic cage, had to be simultaneously one of his most exciting and humiliating experiences of his life. He shifted slightly where he stood, resisting the urge to rub at the lingering sting in his ass through the thin layers of his panties and skirt.

“The two girls,” Ashcroft said to Miss Clara Bell, his tone even, “a small warning. They missed breakfast, so I wouldn’t expect too much from them before lunch.”

“Oh, I never expect too much from a sissy,” Miss Bell giggled lightly. “And really, they both look as though they could stand to lose a few pounds, so missing breakfast is probably for the best. We do like our girls a little trim, after all.”

“Stand to lose a couple of pounds”? Corey repeated in his head, disbelieving. Not once in his life had he seriously been called fat, if anything, always the opposite. Liam too was taken aback, though he naturally dealt with the issue by calling Miss Bell a bitch in his mind. That old perverted fuckwit spanking him while he had to kiss Corey had ensured he had enough open resistance. At least for today.

“By the way,” Ashcroft added, almost as an afterthought, “I did not inform them about the… special function of their cages. I suspect you’ll derive rather more enjoyment from that than I would.”

Clara Bell gave a delighted little squeal. “Oh, you do know me too well.”

“Mm,” Ashcroft murmured, a faint smile touching his beard. “I try.” He turned toward the door. “Well then. Cheerio.” And with that, he took his leave.

It seemed strange that this woman was apparently placed in a position of authority. Her diminutive stature and immature manner made her seem rather easily handled to Liam. The little woman quickly ushered them into the room, and Corey had to smile despite himself, despite the wig, the dress, and the cage. Her energetic manner and pretty face that lit up every time she said something made her incredibly cute.

Clara Bell, who before coming to work for Dominic Mercer had trained to be a schoolteacher, wore her light-brown hair in a girlish bob that beautifully framed her innocent-looking face, with its button nose and bright, Bambi-brown eyes. When she spoke, her voice had an almost sing-song, playful quality to it, one that she in fact practiced in front of the mirror.

As with nearly everything in the mansion so far, this mock classroom was designed to mirror a real one, though the added sissy accents made it clear that this was meant to degrade. The room itself was deliberately small, with a row of windows along the left wall, while the right side was decorated with sissy art projects, outfits cut out from magazines glued onto real pictures of guys, glittering affirmation posters that said things like “Sweet sissies don’t talk back,” and careful sketches of heels and dresses, all neatly pinned up on the wall so no one could miss them. Clearly, the six sissies already present here had been hard at work.

The outfits the six were wearing were the exact same ones Liam and Corey wore. The same pleated skirts that fell just above the knees, the same soft blouses, and the same white pantyhose paired with delicate black ballerina flats gave them, in Clara’s mind, a properly sweet and sissy appearance. The most significant difference between the six and Liam and Corey was their wigs, each one wore a different girlish style: a neat brown bob, a long honey-blonde ponytail, or soft black curls that framed the face. But there was also that the six sissies wore some light makeup, whereas Liam and Corey did not as yet.

Directly opposite the door, facing the class, stood Clara’s teacher’s desk. Facing it in turn were four school desks, two sissies sharing one desk. The school desks, of course, were done up in a deliberately girlish style, painted in soft colors and decorated with little flowers and hearts. They were also noticeably smaller and lower than Clara’s desk, making anyone seated at them look diminished, driving home the point that they were literally lower than the “teacher.”

“Well, there you are,” Clara chimed happily, clapping her hands once as if greeting a regular school class. After a moment, she pointed toward the only free desk, the one in the second row by the window, and chirped, “Don’t just stand there, girlies, sit, sit. Go on, find your seats. It’s not difficult.” Corey lowered his head and started moving immediately. Liam, meanwhile, gritted his teeth for a moment before eventually following. It was becoming increasingly clear to him that he needed to have a talk with Corey about how quickly he was giving in to everything.

In front, Clara picked up her long teacher’s pointer again, which had been leaning against the wall beneath the whiteboard when Headmaster Ashcroft had knocked. It gave her something to toy with as she paced, which she often did while teaching. She was entirely in her element here. Looking out over her class, she saw six already well-behaved sissies, legs or ankles crossed, fingers interlaced, sitting quietly and watching her, and her two newcomers, still sitting like boys. God, how she loved newcomers.

She could only imagine what those two were feeling as they took in the scene before them, her obedient little class, knowing, whether they admitted it or not, that this was their future. And this was only a beginner class. That mattered, because the finished sissies were often so far removed from how beginners looked that it was difficult for them to even imagine becoming like that. But this… this was close enough to be believable. The soft, pleasurable tingles in her tummy told her that she would need to blow off some steam during lunch today, with some luck, one of the more advanced sissies would be down in the bad room again.

Clara tapped the pointer lightly against her palm, her gaze drifting toward Corey, whom she knew was Tiffany’s son, soon to be daughter. “Well then,” she chimed, her voice sounding so bright and excited it was as if nothing in the world could possibly ever be unpleasant, “let’s get started, shall we?”

She turned lightly on her heel and wrote in neat, rounded letters across the whiteboard: “Fashion, Appearance, and Presentation class.” When she was done, she turned back to the class and tapped the words with her pointer. “In this class,” she said sweetly, “we’re talking about haute couture, but sissy style!” She paused and tilted her head just slightly. “Because if you don’t look the part, then what’s the point?”

A few of the other sissies straightened instinctively. “And right now,” Clara added lightly, “you two very much don’t look the part.” She began pacing slowly between the desks. “But don’t worry,” she trilled, “that’s what I’m here for.”

When she arrived in the second row, she stopped beside Corey, the tip of her pointer lifting to indicate him without quite touching.

“Tell me,” she said, her tone curious, “what do you think you’re doing with your legs like that?” Corey froze for a moment before glancing down, suddenly aware of how he was sitting.

“Uh.”

She tapped the side of his knee lightly with the pointer and said, “Mm,” cutting him off before he could answer. “No, no, sweetheart, we don’t ‘uh’ in this class.” Liam’s patience with this bitch was seriously wearing thin, meanwhile. Without Ashcroft in the room, the biggest threat was gone, and that this tiny cunt was walking around this room, completely surrounded by eight guys, thinking she had complete immunity, was infuriating.

“Or what?” Liam muttered under his breath, just loud enough to be heard.

Clara stopped. Slowly, she turned her head toward him, her expression unchanged for a brief moment before her smile returned, just a little brighter. “Oh,” she said softly, “there you are.” The pointer lowered at her side as she shifted her attention fully onto him, her eyes lighting up with quiet satisfaction. “I was wondering how long it would take. There’s always one who needs a little demonstration.”

Liam held her gaze, refusing to look away. “Go on then,” he said, leaning back slightly, legs still spread. “What are you going to do?” A small, pleased hum escaped her. “Nothing at all,” Clara replied sweetly, reaching into the pocket of her skirt and pulling out her phone. For a second, it did not even register what she was doing, her thumb already moving across the screen with practiced ease.

“You see,” she said lightly, now addressing the whole class, “presentation is not optional here. It’s encouraged.” Her eyes flicked back up to Liam. “And every so often, a little encouragement is necessary.” There was a faint click.

Liam flinched. Not violently, but enough. His body jerked slightly, his breath catching as a sharp, sudden sensation shot through him, unfamiliar and immediate. For a split second, confusion crossed his face, then tension followed as his hands clenched against the desk. Clara’s smile widened. “Ah,” she said softly, clearly pleased, “there it is.”

Her thumb moved again. This time, the reaction was stronger, Liam’s shoulders tightening as the sensation hit again. He sucked in a breath through his teeth, his composure slipping just enough for everyone to see. The room had gone completely silent, the six other sissies watching without moving, while Corey stared at him wide-eyed.

Clara stepped forward and stopped right in front of Liam’s desk, looking down at him with that same bright, almost innocent expression. “Now,” she said gently, “let’s try that again.” The pointer lifted slightly, indicating his legs. “Knees together.” Liam hesitated, her thumb hovering just above the screen. “And ankles crossed.”

There was a brief pause, but eventually Liam gave in and reluctantly adjusted. Clara watched closely, head tilted again. The moment he settled into position, she let out a soft, satisfied hum and slipped her phone away again. “See?” she said brightly, turning back to the rest of the class. “That wasn’t so difficult, was it?” Her gaze swept across the room once more before returning briefly to Corey. “And that,” she added lightly, “is why we don’t say 'uh'.”

𝐅𝐢𝐫𝐬𝐭 𝐁𝐫𝐞𝐚𝐤 (𝟏𝟎:𝟎𝟎 𝐀𝐌 - 𝟏𝟎:𝟑𝟎 𝐀𝐌)

Clara dismissed them with a cheerful clap, and the class quickly filtered out into the hallway and then through the glass doors into the garden outside. The morning sun had risen fully now, casting soft light over trimmed hedges and neat gravel paths where small groups had already gathered.

It was easy to guess which sissies belonged to which group. The beginners still moved carefully, a little stiffly, and still basically appeared as guys in drag. The intermediates were smoother, their movements already more natural, hands relaxed, and posture practiced. And the advanced… they didn’t seem to think about it at all. Everything about them looked effortless, as if this had always been who they were.

Near one of the benches stood Madison and Jessica with another finished sissy, talking quietly. When Madison spotted them, her face lit up, and she gave a small, girlish wave, easy and natural. Corey found himself lifting his hand in return before he even thought about it. Liam didn’t. He just stared.

“Fuck this,” Liam muttered under his breath, dragging his eyes away. “I’m not just standing around like an idiot.” His gaze moved across the garden until it settled on one of the other beginners, a guy who looked just as out of place as they did. No makeup, posture not quite right, movements still stiff. Good enough.

Liam jerked his head slightly. “You. Come here a second.” The other guy hesitated, then stepped closer, glancing around briefly as if unsure whether he was even allowed to.

Liam didn’t wait. “Hey, bro. How are we gonna get outta this contract?”

The guy blinked at him. “Get out of it? Why would I want to get out of it?” That answer alone was enough to throw Corey off, who had drifted closer without really thinking about it. As it turned out, five of the six other sissies in their class were here wholly voluntarily. That surprised Corey more than anything else. He had assumed everyone here would be like him and Liam, trapped in some way, looking for a way out. But that wasn’t the case at all.

They had come to the Mercer Foundation on their own, not despite what it was, but because of it. Two of them had dabbled in sissification and saw the Mercer Foundation as someone who could facilitate their jump into a permanent sissy lifestyle. Three others had nothing except the foundation, crossdressers who had been kicked out at home after their secret was revealed, with nowhere else to go. The foundation was their life.

And then there was the sixth one. Named Max. But his situation was… weird, Liam and Corey agreed.

“I-uh… haven’t worn male clothing in some years,” he eventually admitted. “N-not since my two little sisters forced me into dresses. And my parents, they... sorta found it cute and didn’t really care, so my sisters had free rein. And half a year ago they found the Mercer Foundation, and the Foundation gives my parents a stipend, so they’re fully behind the idea now… and meanwhile I get indebted to the foundation for the 'privilege' of being sissified,” Max pressed the last part out between clenched teeth.

Liam was more than curious to ask how it was possible that this weak loser could’ve been forced into dresses by his little sisters but thought better of it. It wouldn’t be smart to alienate the only other guy who seemed willing to get out of his predicament.

Corey, meanwhile, was thinking of his own little sister, Olivia, and how he would’ve reacted if she ever tried to force him into dresses. The thought made him cringe. “No way in hell,” he told himself, trying to push it out of his mind. That his own girlfriend, Emily, seemed already more than willing to accommodate Mercer in this very endeavor was trouble enough.

𝐒𝐞𝐜𝐨𝐧𝐝 𝐋𝐞𝐬𝐬𝐨𝐧 - “𝐏𝐬𝐲𝐜𝐡𝐨𝐥𝐨𝐠𝐢𝐜𝐚𝐥 𝐀𝐝𝐣𝐮𝐬𝐭𝐦𝐞𝐧𝐭 𝐭𝐨 𝐒𝐢𝐬𝐬𝐲 𝐋𝐢𝐟𝐞”

(𝟏𝟎:𝟑𝟎 𝐀𝐌 - 𝟏𝟐:𝟑𝟎 𝐏𝐌)

The second lesson of the day was held in a clinical room, one that felt distinctly different from Clara’s classroom. Where Clara’s space had been a bright, almost playful mock classroom, this one was white, sterile, and smelled of antiseptic. Of course such a class was taught by Dr. Veronica Keene, and unlike Clara, she did not bother with theatrics.

Psychological Adjustment to Sissy Life, as she explained it, was about “alignment.” Alignment between behavior, thought, and identity. It was not enough to act like a sissy in class. The goal was to remove the divide between their sissy self and real self. Apparently, many beginner sissies started out by treating sissification as a role to be performed to avoid punishment. But the end goal was complete internalization of sissyhood.

“Discomfort,” the white-haired doctor said at one point, pacing slowly in front of them, “is not a sign that something is wrong. It is a sign that something is changing. You are not losing anything of value, after all,” she added calmly, making a note on her clipboard without looking up. “You are discarding behaviors that were never right to begin with.”

At several points, she called on students, asking them to describe their reactions. Once, when Liam tried to laugh something off, Keene stopped him mid-sentence. “No,” she said flatly. “You don’t get to hide behind humor.” Liam was left to silently stew in his rage at her humiliating call-out of him, but he knew he wouldn’t return next week, which helped to calm him somewhat.

By the end of the lesson, it had become clear that this class was not about teaching them something new but about cutting away pieces of their old self. Only Keene didn’t seem to regard their old selves as genuine but rather as a front, or a fraudulent performance, something they had put on all their lives and hidden behind. She seemed convinced, to Corey’s annoyance, that at their true core sat a sweet, obedient sissy hidden behind layers of performative masculinity.

𝐋𝐮𝐧𝐜𝐡 (𝟏𝟐:𝟑𝟎 𝐏𝐌 - 𝟎𝟏:𝟎𝟎 𝐏𝐌)

The dining hall, which they entered at lunchtime, was large and, of course, adequately girly. Flowers sat neatly arranged on each table, and tall windows let in plenty of light that played prettily across the pinks, lavenders, and mints of the small, round plastic tables and chairs. The chairs were deliberately low, forcing anyone sitting in them into a smaller, more contained posture. All in all, ten such little tables, with four chairs each, though some sat empty, stood in the sissy section of the room.

Beyond the sissy section of the hall there was the so-called “raised section.” It comprised the other half of the hall and was demarcated by a single broad step that ran across the room, cleanly separating it into two levels. The sissies occupied the lower “sissy section,” while the upper “raised section” was reserved for staff and their trainees, Emily, Corey’s girlfriend, among them. The elevation difference was small, it could be crossed in a single step, after all, but unmistakable.

Another ten tables stood on the raised section, but these were different. They were made of dark wood instead of plastic, they were larger, heavier, and more imposing. The chairs there were taller as well, reinforcing the hierarchy. From where Liam and Corey stood, the contrast was obvious. Those on the raised section were always placed higher up, literally looking down on the sissies, who, in combination with their brightly colored plastic furniture, were truly infantilized.

On the far side of the room, opposite the door through which they had entered, was a service area and kitchen, accessible from both levels. Housegirls moved back and forth between the two sections, Jessica and Madison among them, carrying trays and serving food in skimpy serving girl uniforms. Liam had by now taken to manually reminding himself, “These are guys,” whenever he saw truly advanced sissies and did it here again.

Soon enough Liam and Corey were seated. Two other boys from their class sat with them. Max had to introduce the other as Aidan because he seemed too embarrassed to get out a single word. “But when anyone with some authority is listening, you’ll have to call me Minnie and him Cherry,” Max explained. Aidan’s, or “Cherry’s,” wig was fittingly fire red, and so were his cheeks. His pretty green eyes never once met Corey’s or Liam’s.

Max’s wig was inky black and cut into a neat, feminine bob. The comparison between him and Jessica, who was moving toward their table with effortless grace to bring them their lunch, was simply mind-boggling for Corey. For example, Max’s Adam’s apple was still visible, his voice was still clearly that of a guy, and his face still had a certain sharpness to it despite the makeup he wore. None of that was the case with Jessica anymore, in her tight serving girl’s bodice.

It was easy to feminize the big features, but Corey realized that the real danger lay in all the small details that alone didn’t seem like much of a problem but, when combined, meant that even if Jessica purposefully were to dress as a guy again, she would just seem like a girl wearing baggy clothes in muted colors.

As Jessica reached their table, she set their plates down with practiced ease and then glanced at Corey. When she looked at him, she gave him a quick, smug wink that seemed to say, “You’re a mess, but I see you.” Corey looked down, blushing, unable to suppress a small smile. What was it about this sissy that made her seem so like the big sister he never had?

The food she had served them was something the famished Liam could only really describe as “a sad fucking assortment of various grasses,” which he then promptly described it as, to laughter from Corey and Max and even a little smile from Aidan. It was clear they were all going on a diet.

In truth, the plate was a carefully researched portion the Mercer Foundation had designed to provide all necessary nutrients while encouraging muscle loss and fat redistribution: a bed of mixed greens with spinach, a few slices of grilled chicken breast, a halved boiled egg, and a sprinkle of seeds and nuts for texture. To stay hydrated, they had each been given a tall glass of infused cucumber water.

While eating, Corey let his gaze lazily drift around the dining hall when he suddenly saw someone familiar on the raised section. “…No fucking way,” he muttered under his breath, feeling his stomach drop. Liam immediately followed his gaze and saw her too. Emily sat at one of the dark wooden tables, one leg crossed over the other, engaged in what seemed to be a lively conversation with a tall, broad-chested, and, Corey hated to admit it, handsome guy.

The guy, named Jason, though Corey didn’t know this yet, had messy, dirty blonde hair of medium length, a strong jaw, and a face that seemed permanently set in a relaxed smile. His broad shoulders filled out his shirt without effort, and everything about him, from the way he sat to the way he leaned in while talking, carried an unthinking, natural confidence Corey immediately hated him for.

Corey knew he was pretty, people had told him that all his life, but he was also small and not the strongest. Girls had never been unwilling to date him or anything, but they also took on a certain “relaxed” attitude around him, one that he interpreted as “not being exciting enough.” In the back of his head, there had always been this anxious scenario playing out. Guys like that, like Jason, stepping in and talking to his girlfriend, and Corey just… not being able to do anything. Occasionally, when he spotted a guy he instinctively knew he couldn’t compete with walking toward them, he would subtly steer Emily to the other side of the street without explanation, talking over the moment as if nothing had happened. But now there was nothing he could do except watch this fucking guy over there, talking to “his” girl, and her making such intense eye contact in return. It made Corey’s chest tighten with hot but ultimately helpless rage.

But one of the advantages Jason had with girls, one Corey didn’t even know he had, was that Jason had never considered any girl “his.” Perhaps it simply came with being successful with girls.

𝐓𝐡𝐞 𝐁𝐚𝐝 𝐑𝐨𝐨𝐦 (𝐂𝐥𝐚𝐫𝐚’𝐬 𝐋𝐮𝐧𝐜𝐡 𝐁𝐫𝐞𝐚𝐤)

While Corey and Liam ate their lunch, Clara Bell entered the teacher’s lounge.

As she did, Doctor Keene immediately got up from the table that stood central to the room, walked to the coffee maker, and poured a cup for Clara. After offering it, she said, “Angel is being punished again. I sent her down there earlier today for not showing enough enthusiasm even after several warnings.”

It was normal that Clara would be informed of this, as head of discipline, it was her job to deal with girls in the bad room. Angel was there every now and then, almost always for the same reason: lack of enthusiasm. For a beginner sissy, it was fine to simply go through the motions, be obedient, and do as she was told. But for intermediate sissies, as Angel was, expectations grew to now really behave in a sissy manner.

It was not enough for an intermediate sissy to just mince. A beginner might take small, careful steps, knees slightly turned inward, arms held stiff at her sides as she tries to remember every rule. But for an intermediate, it had to look effortless. Her steps had to flow, hips swaying naturally, hands relaxed, as if moving like that were the most normal thing in the world for her.

For a beginner sissy, it was fine if her mince looked mechanical, stiff, and strange as long as she did as she was told. But an intermediate sissy’s mince could be expected to look natural: small steps, fluid movements, arms held close to the body with limp-wristed, effeminate little movements of her hands.

At the beginner level, regarding sissy speech, it was acceptable if the sissy read off the pages without much intonation or emotional expression. It was also expected that a beginner would only speak like that when prompted and revert afterward. By the time they reached the intermediate level, however, it was expected that she used fillers like “like,” “uhm,” and “totally” in normal speech, referred to herself differently, and carried real emotional expressiveness in her voice. An intermediate sissy begging for something should be willing and able to degrade herself verbally to get it, and it should sound like she genuinely believes every word she says.

And then, of course, the curtsy. A beginner often forgot to curtsy, and when she did, it was stiff, rushed, and clearly done to avoid punishment. But an intermediate curtsy should be smooth and deep and look as though the sissy has learned her place and accepted it.

“How long has my sweet little angel been down there, and what’s the punishment?” Clara asked Veronica as pretty Clarissa Sterling opened a window to smoke her Sobranie.

“Mm, about two hours now,” Veronica answered. “It’s relatively standard: latex catsuit, vibrator, little condom strapped on to collect the evidence.”

“Ooh, that sounds like fun,” Clara squealed. “I think I’m going down to play with my little angel.”

The “bad room” surrounding Angel was silent, except for the buzzing of the vibrator stuffed deep into her tush. Angel didn’t know how long she’d been down here. Hours? Time had stopped early, at about her first humiliating orgasm. The problem with these kinds of full-body orgasms caused by vibrators was that they really wiped away any sense of time.

The latex suit clung to her less like clothing and more like a second, suffocating skin. Each twitch of her bound legs rubbed her thighs together, slick with sweat and sticky at the creases. Her curls, damp and matted by now, stuck to her cheeks as she trembled. And all the time, the buzzing inside her went on unabated. The cage at her crotch, her clitty, they called it, had a little condom pulled over it to catch every bit of release.

By now, she’d cum three times so far. Or rather leaked, as Clara had once called it with a delighted giggle. The first had been not long after she had been strapped in, her body convulsing softly as warmth spread out through her belly, pushing itself through the pressure of the cage and finally spilling out into the small, sticky condom taped beneath it.

Her arms were chained above her head to the ceiling, slick with sweat and numb at the fingers. Her legs trembled between a spreader bar. The whole setup caused her to sway like a human pendulum.

Then, quite suddenly, light.

Angel flinched, squinting, and then already came the sound she had dreaded. “Heeeellooo, my sweet Angel!” Clara cried, delighted. “My, my, don’t you just look like a melted lollipop!” Angel whimpered. That was all she could do. Her legs were shaking, hips twitching from the overstimulation. Her cheeks burned.

Clara crouched near her, the frilly hem of her dress flouncing as she peered under the latex-covered sissy. “Now, let’s see what your pretty little clitty’s been cooking up for me so far…” With one soft pop, Clara detached the sticky condom from the cage. It made a squelch as it peeled away, and Angel wanted to sink into the floor.

“Oooooh! Two-and-a-half spoonfuls!” Clara cooed. “Someone’s got a gushy tushy! That little vibey must’ve sung you lullabies, huh?”

Angel shook her head weakly, but her arms barely moved. Her mouth opened. Then closed. Then opened again. “Ah, ah, ah,” Clara wagged a finger. “You know the rule, sweet sissy. We doooon’t waste. This is for sipping!” She stood and held the dripping condom aloft like a prize, pinching the tip closed. She walked around Angel slowly, humming, dragging her finger along the sissy’s latex-covered shoulder. Then she stopped in front of her.

“Open up, darling dear.” Angel hesitated for a moment and kept her mouth closed. “C’mon, cupcake. Open that sweet sissy mouth.”

But knowing Clara, Angel gave in not long after, slowly opening her mouth. “Good giiiirl,” Clara sang.

The condom was tilted, and the watery contents oozed onto Angel’s tongue, the salty, bitter taste running down her throat. Clara clapped her hands together with delighted glee. “Ooh! Good job, sweety! Not one little dribble down your chin!”

Angel stared at the floor, at the toes of Clara’s bright yellow Mary Janes tapping idly against the concrete. She just couldn’t stand still. What the hell was wrong with her, Angel wondered?

“Aww, shy now?” Clara asked. “Don’t worry, dolly. Shy little sissies are the tastiest kind.”

The latex suit squeaked as Angel shifted, trying to find a way to ease the pressure in her arms and legs. But the spreader bar kept her wide open, the chain kept her pulled upright, and the tight cage remained fixed in place.

“Angel, my little sweetie pie…” Clara asked, her voice turning syrupy sweet in a way that Angel knew meant danger. “Why is it that every time you’re down here it’s because you read out your lines like a cardboard box instead of a sissy? It’s not that difficult to be a convincing little sissy, is it?”

“I’m sorry, mistress, I just can’t!” Angel whined. Clara knew what this was, of course, and she also knew Angel wasn’t lying. Many sissies experienced a sort of psychological block when it came to actively humiliating and embarrassing themselves in front of others. For example, it was one thing to read a flirty line off a sissy textbook in a flat voice, it was quite another to actively and convincingly act like a feminine sissy in love with someone.

The culprit, of course, was often the sissy’s remaining self-respect. The idea that certain things were so humiliating that it was better to be hurt for not doing them than not be hurt but have to do them. To destroy this sense of self-respect was Clara’s mission, and after her experiences with Jacob, her cheating son-of-a-bitch ex, and current sissy Jessica, there was little she enjoyed doing more. So far, she hadn’t met a single sissy with whom, in due time, she didn’t discover a reason for why they deserved their sissification.

“Now, now,” Clara said, tapping Angel’s chin with one finger, tilting her head up. “You know what comes next, don’tcha, pretty girl?”

𝐓𝐡𝐢𝐫𝐝 𝐋𝐞𝐬𝐬𝐨𝐧 - “𝐃𝐢𝐬𝐜𝐢𝐩𝐥𝐢𝐧𝐞, 𝐎𝐛𝐞𝐝𝐢𝐞𝐧𝐜𝐞 & 𝐁𝐞𝐡𝐚𝐯𝐢𝐨𝐫𝐚𝐥 𝐂𝐨𝐫𝐫𝐞𝐜𝐭𝐢𝐨𝐧”

(𝟎𝟏:𝟎𝟎 𝐏𝐌 - 𝟎𝟑:𝟎𝟎 𝐏𝐌)

Two stories above, completely unaware of Angel’s ordeal, Liam’s and Corey’s day began to speed past as the sleep debt from their early wake-up slowly caught up with them.

The third lesson brought them back under Doctor Keene’s supervision, though this time the focus shifted away from thought and toward response. Where the morning had been about understanding and internalizing, this lesson was about reaction, how the body behaved, how it could be corrected, and how quickly it could be made to comply.

Halfway through the lesson she asked the room, “How did you respond to authority before you came here? If you received an instruction to do something you didn’t want to, all of you ignored that instruction and simply carried on doing what you wanted to do, didn’t you?” The sarcasm in her tone was hard to overhear, and her implication was obvious. She was suggesting that all of them had been obedient all their lives and were therefore prime sissification material.

As no one volunteered an answer to Keene’s question, she decided to zero in on one of her eight beginner sissies.

“What about you, Sophie?” she asked, a thin smile playing on her lips. “I’m sure when you received an instruction, you simply blew it off.”

The boy with the curly brown hair shook his head. This caused his round glasses to slip slightly down his nose and made his hoop earrings jingle. “No, Ma’am. Of course not,” he answered. He knew it was better to accept the implication of always having been an obedient little failmale than to annoy Keene.

Sophie had a sweet, soft face with beautiful, large brown eyes that his round glasses framed. Being a beginner sissy too, he was still recognizable as male. Though his glasses, wig, and soft face already clearly pointed in the direction his sissification would take him. Before being taken in by Dominic, Samuel Ellwood wore rectangular glasses. It had been one of Dominic’s first moves to replace his glasses with round ones, a move that alone significantly feminized his face, much to Sophie’s chagrin. But he needed to wear glasses to see, so what choice did he have? The wig he wore, long, very curly brown hair, mirrored what Dominic had planned for his real hair once Sophie’s was long enough.

All in all, Dominic aimed to go in a “bookish” direction with this particular sissy. A cute, nerdy slut to take from behind as she recited memorized sissy theory, just as perfectly as he now could dentistry. Though his knowledge in oral anatomy might give him a head start in practical lessons, like the blowjob, as well.

Dominic didn’t know exactly what it was, but there was just something incredibly hot to him about derailing a well-prepared life like this. In high school, college, and then dental school, Sam had always received top marks and, because of his parents, had known from a young age that he would become a dentist and inherit their dental practice. Instead, he was now on his way to becoming a sissy.

“Your body,” she noted, “is far more cooperative than your mind. It simply needs to be taught what happens if you don’t do as you should. It’s your mind that needs justifications, really, the mind needs a story.”

𝐒𝐞𝐜𝐨𝐧𝐝 𝐁𝐫𝐞𝐚𝐤 (𝟎𝟑:𝟎𝟎 𝐏𝐌 - 𝟎𝟑:𝟑𝟎 𝐏𝐌)

The second break was quieter than the first. Conversations were shorter, as the length of the day really began to settle in. Liam found himself thinking less about escape and more about simply getting through the next hour. In a way, this was quite similar to his regular time in school, where the afternoons had also mainly been about staying awake.

𝐅𝐨𝐮𝐫𝐭𝐡 𝐋𝐞𝐬𝐬𝐨𝐧 - “𝐓𝐡𝐞𝐨𝐫𝐞𝐭𝐢𝐜𝐚𝐥 𝐅𝐨𝐮𝐧𝐝𝐚𝐭𝐢𝐨𝐧𝐬 𝐨𝐟 𝐒𝐢𝐬𝐬𝐢𝐟𝐢𝐜𝐚𝐭𝐢𝐨𝐧”

(𝟎𝟑:𝟑𝟎 𝐏𝐌 - 𝟎𝟓:𝟑𝟎 𝐏𝐌)

The final lesson of the day returned them to a more structured classroom environment. By now, fatigue had really begun to set in, and it showed. Their attention wandered, and even simple instructions took longer to register. Mistakes came more easily, and their patience, especially Liam’s, wore thinner with each passing minute.

Doctor Keene’s voice carried evenly through the room as she continued the lecture, outlining some principle of this and framework of that with the same monotone voice as always. But by this point, it all blurred together. Corey found himself staring at the page in front of him, rereading the same line without absorbing any of it. Rather, he was more interested in the fact that he was actually reading a textbook regarding sissification. Dominic had really pulled out all the stops with this little pet project of his.

This final class, being a theoretical one, was really awful. At least during “Discipline and Behavioral Correction,” they got to move around. Here, they just had to sit, listen, and try to stay awake, counting down the minutes.

𝐃𝐢𝐧𝐧𝐞𝐫 (𝟎𝟓:𝟑𝟎 𝐏𝐌 - 𝟎𝟔:𝟎𝟎 𝐏𝐌)

Dinner mirrored lunch: small, carefully arranged portions that looked more decorative than filling, a light pasta with a fine cream sauce and a few neatly cut vegetables. Liam and Corey remained hungry, but that too was by now dulled by their fatigue. Even Liam didn’t complain this time, though the tension in him had not gone anywhere.

Corey, meanwhile, found that the deeper his exhaustion set in, the harder it became to ignore the many new sensations he had been subjected to that morning by Ashcroft and Keene. The tight, ever-present pressure of the chastity cage, that damned itch of the wig against his scalp, and the constant sensitivity of his hairless legs all seemed magnified to him now. During most of the day, he had been able to push it all to the back of his mind so he could focus on what was in front of him and avoid punishment, but now his mind began to fail him.

𝐋𝐞𝐢𝐬𝐮𝐫𝐞 𝐓𝐢𝐦𝐞 (𝟎𝟔:𝟎𝟎 𝐏𝐌 - 𝟎𝟗:𝟎𝟎 𝐏𝐌)

Both Liam and Corey found themselves quickly back in their room after dinner. Rather than enjoying their three hours of leisure time like the other sissies, they simply wanted to go to bed. Nobody stopped them, of course. During “free time,” the sissies were allowed to do what they wished within reason.

Liam simply dropped onto the bed with a quiet groan, not even bothering to comment on anything for once. Even his hunger that still lingered in the background had lost its bite, overshadowed by exhaustion. In his mind, the idea of sleep had become less about rest and more about escape. If he slept, the day would end faster and the weekend come sooner, and by now he was sure as fuck that he wouldn't return next week. He would go to the police, or run away, or just break his contract and deal with his gambling debt another way.

While Liam was still thinking, Corey was already fast asleep. He had not even changed out of his clothes or wig and was just lying like that on his side of the bed they shared. Around them, the mansion still moved, and from beyond the blinds they had drawn, light still fell in. Faint sounds carried through the hall in front of their door, distant voices called, footsteps sounded, and doors were opened and closed. Other sissies made use of their leisure time, talking, practicing, or simply existing within Mercer's strange little empire.

𝐋𝐢𝐠𝐡𝐭𝐬 𝐎𝐮𝐭 (𝟎𝟗:𝟎𝟎 𝐏𝐌 - 𝟎𝟔:𝟑𝟎 𝐀𝐌)

At nine sharp, when the day officially ended, Corey and Liam had already been asleep for three hours. The electronic lock on their door shut them in automatically, as it would every night. And with that, their first real day in Dominic Mercer’s clutches came to its quiet close…