“I know just the place you can stay,” The saleswoman said yesterday, “but you have to promise to follow the rules or they won’t be happy about it, okay?” You agreed at the time, not knowing just how much worse your predicament could get.
That’s how you spent the next eight or so hours wearing nothing more than an oversized T-shirt, napping in the back of a station wagon after your tiny child body wore itself out. As you drift in an out of consciousness, the town falls away to highway, then to forested backroads, then a bridge across a foggy marsh. By the next morning, you find yourself at a boarding school isolated from the rest of the world. Surreal gargoyles peer down at you from atop a steep shingled roof, daring you to come any closer. You know, intellectually, they can’t hurt you- yet you have the heart of a child and your imagination runs with the idea regardless.
“Hmph.” The headmistress purses her lips as she lifts your chin with her red-painted fingernails. “Your child would not normally be permitted at our fine academy on such short notice, but we can make an exception. They may stay for one semester, and if they adapt, we may have a new student on our hands.” She firmly pats your curly mop of hair. “IF they adapt.”
You follow cold, tiled corridors to your dorm room. The old radiator clangs as it warms a soft bed for you. Your new headmistress folds her hands behind her back and gives you the bad news.
“While attending the academy, you will be required to wear our standard uniform. I hope you understand.”
Your clothes for the foreseeable future are laid out before you. A white button-down shirt, a short silk necktie… a pleated maroon skirt with matching thigh-high socks, white cotton panties, a training bra, a maroon hair ribbon and an otherwise ordinary black backpack. “This is, after all, a girl’s charm school.”
You have several objections. “Um, first of all… “
The headmistress takes a step towards you. Her expression is unchanged, but her body is moving like a tiger seconds from pouncing. “You will refer to authority figures as ma’am or sir. You will refer to ME as Headmistress. Do you understand, Crystal?”
“My name’s not Crystal, it’s- “
Your vision goes red as a hickory switch strikes the side of your head above the ear. Pain ripples through your body with confusion not far behind. The Headmistress had her hands in plain sight, her clothing doesn’t even have pockets long enough to conceal a stick. Where did that strike even come from? “ALSO, you will defer to adult authority figures as long as you are a student in these halls. You are allowed to ask questions, and in fact are expected to do so as part of the curriculum. Bickering and obstinacy, on the other hand, will not be tolerated. The next lash will be on your face. Do you understand, Crystal?”
Blood begins to dribble from your scalp. “Y… yes, Headmistress.”
She claps once and smiles. “Good! We shall get you a styptic and begin right away.”
Your oversized shirt, the last bit of evidence of your old life, is packed away like a half-remembered dream. You stand naked before the school uniform... and dare to ask a question. “Won’t everyone notice I’m not a girl?”
“The faculty shall leave that up to the student’s own scruples. Anyone found mocking you for your appearance is clearly not absorbing the lessons we teach. What we do not trust are your own scruples, Crystal.”
The headmistress watches your face for the signs of confusion. She sighs as if a boulder is forcing air out of her chest. “We know you are a transformed adult among children and have prepared for this eventuality.”
In her hands is something truly evil. It is a short, hollow plastic device with a single hole at the far end, a tight loop meant to hold something snug, and a locking mechanism with a tiny key. For reasons which were just explained to you, it fits your measurements exactly. Silently, you curse your lack of innocence. Silently, you wish you didn’t know this was a chastity cage.
At the very least, you are afforded the dignity of putting yourself in the cage. There are a few uncomfortable moments- exactly two moments, followed by quietly popping into place in a surge of relief. There isn’t even a satisfying click as the lock turns, only a slight increase in pressure. What little you’ve seen of these things on the internet made them look like they were supposed to be difficult to conceal, but your own barely sticks out from between your legs.
Your face begins to flush red as you pull the panties on. Years of wearing loose boxers have let you forget just how snug underwear can be, especially when it is meant for someone skinnier than you. Softness wraps all around you, yet your crotch is numb to all of it; from under the panties you can’t even see anything more than a slight bump. A twitch followed by an iron vice grip around your trapped genitals reassures you that they are, in fact, still there.
While you pull the stockings up your legs, the headmistress nods slightly as if this were the most normal thing in the world. “As you might imagine, your discomfort is the point. It comes off for hygiene and medical emergencies, and absolutely no other time until graduation or expulsion. Do you understand?”
“Yes Headmistress!” You bark out like a wounded dog. While you strap on a brassiere meant to hold breasts which will never grow, you consider your options. This place is clearly insane and only holds contempt for you. You’re expected to fail, and it would be easy to simply be expelled and leave… but your old identity is hundreds of miles away, with a different face and name, while you’re a boy named Crystal wrapping a pleated skirt around his hips and only barely concealing his crotch bulge. Plus, if they’re sadistic enough they might never let you leave in the first place.
Yet as the shirt buttons up around you and the tie tightens- you don’t have to pretend not to understand neckties around the headmistress- you start to feel the pull of this place’s gravity. What kind of knowledge are they so keen on hiding that they built this place so far from civilization? The headmistress knows magic exists, so she can’t be just another authoritarian psychopath, can she? Your stocking feet slide into a pair of brown leather loafers, and your uniform is almost complete…
“I’m certain you’ll find this last part entertaining, Crystal.” With a small flourish, the headmistress slips a wig cap over your head (which only stings your wound a little bit), then grants you a long, straight brunette wig with the ribbon already tied on. It doesn’t quite match your looks, but you can always swap it out later. “There you are, one proper charm school student.”
It feels like mere seconds before you awkwardly show up at your first class. The other girls… oh dear lord they’re gorgeous. It’s like watching a parade of porcelain dolls pass by. Are you… jealous?
The teacher, who is thankfully not the headmistress, signals for the class’ attention. “Greetings, ladies! I am Mrs. Constantine, and I will be your grammar teacher this semester. Now, grammar is one of the Liberal Arts. Can any of you name all seven of the arts?”
You’re scribbling along with her words in a notebook, but you’re barely conscious of what she’s saying. All you can think about is your next move…