Sissy Education I

Story by Ashley Natter on SoFurry

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#1 of Sissy Education

A commission for Jammish (https://www.furaffinity.net/user/jammish)


The car jolts and splashes along the rutted lanes flooded by the heavy rains. Through its grimy window, all that Jammish can see is the unfamiliar countryside with bare hedgerows and the skeletons of trees, looming out of the morning mist. The young housecat shivers and clutches his travelling suitcase around him more tightly, its worn and sturdy sides are comforting to him.

The Policewoman, a strong lioness dressed in a sharp uniform and with attentive blue eyes that Jammish has felt looming over him during the entire trip stays immobile; she had been accompanying him since he had been captured at the airport. She kept a diligent vigil over the young housecat, even though Jammish never would have even dreamed of running away, he is sure that the lioness can hunt him down and bring him back, no matter what he does.

Where she is strong and fit, Jammish is small and weak. The young housecat's coat is almost entirely white, with only his hands and the tip of his tail being a charcoal black, but his most distinctive feature is the red strip on his right shoulder.

Her uniform is a perfect black, impeccably kept, immaculately framing her fit body. She had hardly spoken a word, not yesterday all the way down in the train from the airport, nor this morning on the car journey. But she has never stopped watching the young housecat. Even without looking at her, Jammish know she's watching him now.

Perhaps she's wondering if he will falter and try to run away, maybe she is hoping he will try to run so she can have some fun with him before the delivery.

This isn't what Jammish had planned for his life.

As many other housecats, he had been born in a very different world. Jammish had once enjoyed a life of luxury and riches, being the son of an affluent CEO, he had been groomed from birth to one day take control of the whole corporation, taught in the best private schools that money could pay for, but nothing of that mattered anymore. The revolution had brought a new order where people like him had no space in positions of power. Housecats these days were seen as weak and meek in comparison to the strong and domineering lions that had taken control of their society.

The housecat had made the unforgivable mistake of trying to run away, he even managed to get all the way to the airport before finally being caught by the police.

They reach a crossroads and turn right. This lane is more deeply pitted, rocking the car from side to side. The trees cluster thickly here, deepening the gloom.

"Please, I can pay you if you let me go," Jammish pleads in a low voice, eyes fixed on his white feet.

"Not far now," she twists her mouth into a smile, but her eyes slide past his.

The forest on one side of the lane is replaced by high stonewalls stretching into the mist. Before long, the car jerks to a halt.

Looking out, Jammish see that they have stopped by tall iron gates. His pulse beats faster. "This isn't the place, is it?"

The lioness nods with a small smile in her lips.

The knot in his stomach tightens. This is far grander than he had expected.

"Keep your face smooth. Don't betray your feelings," he whispers to himself.

A slim housecat walks out of the lodge; he wears a long, loosely fitted leather jacket that gives glimpses of metal under it as he moves. Chains connected to piercings in his nipples and bellybutton, the chain forms a delicate harness around his chest, a collar around his neck, and elegantly locks his small cock in some form of chastity cage. The chained sissy unlocks the gates. As the car passes, he stares at Jammish and smiles with a small wave towards him. Jammish is surprised by his decorations, the image of himself ending being like him crosses his mind, but deep inside he knows that his destiny will be much worse.

The gravel driveway winds through the grounds leading to an imposing house set on a rise, with an ornate roofline of turrets and cupolas. At the sight of it his heart sinks.

What will they do to him?

When they stop again, the lioness says, "We have arrived." She's smiling again, almost as if encouraging. She opens the door and descends from the car, ordering the housecat to follow with a simple gesture. But Jammish shrinks back, feeling a fluttering in his chest like moths trapped behind his breastbone.

For a moment Jammish consider if he can try to run, if by some way he can escape this place, or if he can even survive with his sanity intact.

A tall and slim cheetah lady in a black dress appears in the doorway and speaks to the lioness in a voice too low for him to hear.

Two sissies dressed in frilly maid dresses comes to the door of the carriage and look at Jammish with curiosity, both of them have large leather collars in their necks.

"You must get out now." Says the cheetah in a polite, but not warm voice.

Somehow, his feet carry him down to the ground. Next to him is a low railing surrounding the lawn. Jammish can easily step over it; walk away across the grassy space, away from all these staring faces.

But he can't.


In the misty light, a weight of stone looms over the young housecat, the building looking even more forbidding now that he can see it properly.

The cheetah looks over him with a bland smile. "My name is Ms. Steed."

His mouth dries.

"I put myself under your command, mistress," Jammish repeats the mantra as he have been taught. "Jammish exists to please you."

She smiles again. "We have been expecting you, soon enough you will really mean these words."

Blood drums in his ears, darkness slides in at the edge of his vision.

A hand touches his arm and his sight clears.

"Please come with me," her grip on his arm is firm.

Jammish glances at his box.

"Don't worry, one of the servant-sissies will bring that in."

Jammish walk up the steps, past the stout heavily studded door. In the porch he stumbles on the coarse mat, but Ms. Steed's arm prevents him from falling. His feet carry him through the inner doors past twin Venus-symbols rising in stained glass.

Inside, Jammish finds himself in a wide vestibule tiled in black and white diamonds that dazzle his eyes. A vaulted ceiling arches overhead. Directly in front of the housecat is a set of tall double doors. The vestibule is empty apart from a polished table that holds arrangement of flowers under a glass dome. The flowers are fresh and seem to have been recently collected.

Ms. Steed presses him on. Her footstep echoes on the tiles, the sound of her heels like a perpetual remembrance that her position is superior to the housecat, in comparison his naked paws make no sound.

They go down a corridor on the right. After passing several shut doors, they come to halt outside a door. Ms. Steed holds up her hand. "Please wait." The door closes behind her, leaving him standing outside.

Jammish hear a jingling noise and a young sissy fox in a green dress and an apron appears out of the gloom, he has bells tied to his wrists and ankles that make noise as he walks. His fur is black, with only a hint of soft makeup that makes him look almost like a fairy. He nods at Jammish with a big smile, and then knocks on the door.

Ms. Steed appears. "Ah, Twinkle. Come in." The door closes behind her.

Jammish can hear voices, but not what they are saying. Then the door opens again and Ms. Steed calls, "Come in." he hesitate, but there is no way to disobey her orders. Jammish finds himself crossing the threshold before he can even think about disobeying.

Immediately his eyes are drawn to the elegant desk by the window where Ms. Steed is standing, looking at three pieces of paper lying on its polished top. She studies them, leaning down and frowning, as if the writing is hard to decipher.

The young sissy fox, Twinkle, waits with his hands clasped in his back, making his small, budding breasts protrude, he keeps smiling to Jammish.

"Take a chair," Ms. Steed gestures to one in front of the desk.

Jammish sink on to it, clutching the arms. His heart thumping hard on his chest.

Ms. Steed scrutinizes him for a moment.

"You are very pale for a housecat, Mister Wingder," she says reinforcing his species so that Jammish know he's inferior in her eyes, a being worth less than an animal.

"I'm sorry," Jammish replies almost automatically, knowing that it was one of the few answers that wouldn't put him in trouble.

Ms. Steed leans forward. "Right now you are worth less than any of my beloved dogs, but we can make you better here, follow our orders and work to get better so that one day you can receive a proper position for someone of your species." Her manner is kind, as if she pits his situation.

Jammish stare at her, bewildered. He swallows hard. "Why would you do this?"

"Because you're a housecat."

"That's bad?" Jammish asks utterly confused.

"Yes, but for your luck this is a school." she pauses. "Here we will make you feel better, this is a perfect place for a young sissy like you to blossom out."

Ms. Steed smiles. "You are lucky that you are here where we have the skill and the will to cure you, in many other countries people like you are allowed to walk free, a danger for themselves and the community. You will soon settle in."

She turns to Twinkle. "Mister Wingder seems quiet enough at the moment, but we need to keep him under close observation for now. We will try him in the Main Gallery for now."

She glances at me. "Tiana Twinkle is one of our most dedicated students, he once was like you, but now he has learned his proper position. He will look after you and make sure you are progressing in your education."

Jammish looks at Twinkle, wanting some reassuring sign, some hint of pity. But he says, "Come with me," in a sweet, girly voice, and stands by the door, holding it open.

Jammish looks at Ms. Steed. he should say something. "I--" But his voice dies.

Twinkle make a small movement of his feet that makes his bells ring and gestures with his head. Jammish want to ask him what they will do to him in this place, but the sissy moves too fast just ahead of him.

The corridor ends at a door. Twinkle produces a key from a small pocket from her dress and graciously opens the door. The door swings open, they pass through, and Twinkle locks it behind them. Now They're walking on bare tiles; the tap tap of the Twinkle's high heels echoes on the stone.

Jammish try one more time. "Do stop! This is a mistake. I shouldn't be here."

But the green fairy moves ahead of him relentlessly. Powerless to make him turn, Jammish is forced to follow him until he's lost, trapped in a maze of passages and locked doors.

Twinkle ushers him into a high-ceilinged, narrow room with a stone floor. It has a row of windows like slits, high up in one wall, and along the opposite wall are shelves stacked with linen. A musty smell pricks his nose, a smell of unwashed clothes and damp.

Twinkle gestures towards a wooden bench. "Get undressed."

Jammish stares at him too astonished to speak.

"You must have a bath."

"But I'm quite clean."

Twinkle frowns. "It's the procedure."

"But I'm not dirty. I--" he sees the look in the fox's eyes. He's not that much older than him, Jammish is at least a head taller, yet he doesn't dare to defy the fox.

"But that's not everything, is it?" Twinkle's tone was mild, but Jammish feels as if his hand had been slapped. He takes a step back, feeling as if he was back in school and in the headmistress' office for a reprimand.

"Umm, sorry?" asked Jammish.

"We take care of each other in here," says Twinkle, looking at Jammish with a soft smile on his lips, "You need to learn that we don't want to hurt you, just help you become better."

"I know what you do in here," replies Jammish confidently, "I don't know what lies they feed you in here, but I don't like it at all."

"Ah but if you are so confident," Twinkle replies firmly as Jammish feels a faint flutter of panic in his stomach. "Then why don't you allow me to show you what we really do."

"Well, yes, I..." Jammish struggles to reply.

"Do you understand why I chose to serve the lions?" Twinkle cuts Jammish off. "Do you understand why I do their bidding and follow their desires?"

Jammish shook his head and look down, not wanting Twinkle to see how embarrassed he suddenly felt. There was something in the cadence of his voice, the flicker of his bells that seemed to attract him like a spiral, always falling deeper and deeper. Twinkle was right, though Jammish hates to admit it. If he didn't understand why did they choose this life, how could he say it wasn't for him? Jammish wants to protest. The feline feels his normal confidence ebb away, what was going on here?

"It's not for everyone," Twinkle begins, sounding almost as if he is giving a lecture, "being a sissy."

"I'm not talking about some mindless slave," Twinkle continues, a look of distaste on his face, "The sissies in here choose it. Oh sometimes, life doesn't give them much of a choice, but even then, it's up to them in the end and We'll only take a sissy who has the right attitude, who's up to it."

"Up to it?" echoes Jammish, sounding dim even to his own ears.

"Yes," Twinkle says, warming to his task, "You have to understand it's a distinguished honor and privilege. You provide a vital service to our society."

"But, you are like a low servant to them," replies Jammish, the thoughts coming slow and difficult.

"Well, quite," Twinkle shot back, "But that's our proper position, don't you agree that one should do what pleases them the most, independent of money or status?" Twinkle only give Jammish time for a slight nod of the head. "Before the Revolution, most people spend their days in mindless and pointless pursuit of money and status, but the new order has done away with all that. Now we can all enjoy what give us the most pleasure and contribute to society each in their own way."

Jammish wonders if he was supposed to say something, but before he had a chance, Twinkle asks "Now, do you have any idea where you fit in all that?"

Twinkle looks straight at him. Jammish couldn't look away. Much as he wants to, he can't think straight. "No," is all he can say.

"Well then," smiles Twinkle. Jammish sags with relief as he feels released from the vulpine's gaze. "Why don't you let me show you?"

"Yes, Miss Twinkle," replies Jammis, shyly almost automatically. He feel his own words blurring, almost as if he was repeating a script someone was whispering in his ears.

"Yes, so educated and nice, but there's no need for this between us, I'm just a sissy like you. I left home early, my parents were," Jammish could see the emotion in Twinkle's eyes, "well, let's say they didn't help much. The first year was the hardest, living on the streets and doing small jobs here and there just so I could survive. I had nothing when Mistress Steed found me turning tricks for food, she offered me warm food and a bath if I was only to listen her for a moment, she told me of a better way to live, a way to have a purpose in life if I was only to surrender to her."

Jammish is surprised at how calm Twinkle is. "Aren't you bitter or anything?" He could sympathize.

Jammish see the vulpine's eyes flick away and then back again. "No, I'm grateful to her from rescuing me from a short and unhappy life."

"Thank you for being so open," says Jammish quietly.

"So," Twinkle asks, "you understand a bit better now?" Jammish nods and the sissy continues, "About the choices I have made, it takes strength to surrender like that, doesn't it? To find your place and be content on it. There's a fine line between us, even though you still don't see it. Why don't you come with me and stand in front of the mirror for a moment?"

Jammish looks around, confused. Mirror? Then he sees a large floor length mirror on one of the walls. He must have not noticed it when he came in. A little reluctantly, the young housecat goes and stand next to Tiana, both of them looking into the mirror.

"Now answer me honestly," admonishes Twinkle. "We are very similar, aren't we? Look at how small and weak we look; do you think people like us are apt to lead and command?" Jammish wants to rebel, to refuse to answer the question. It was silly, it was outrageous. Twinkle had no right to ask such a thing. And anyway it was obvious, but then Jammish looks in the mirror.

At first sight it was just the two of them, both looking straight into the mirror, he with his simple travelling clothes and Twinkle with his green dress. He had to admit they didn't look the same, Twinkle had a spring to her steps, an ease smile. He seemed weary, tired, and dirty from the road, but then there was a blurred image over him, the strong shape of Miss Steed standing just behind him, one hand pulling him close by the waist while the other rests possessively over his neck, pressing ever so slightly so he could feel her force. She is naked, her perfect body almost invites adoration.

"Wha..." Jammish whispers, nervously.

"What was that dear?" asks Twinkle and suddenly the mirror is not there anymore, they are alone in the bathroom.

"I look sad," Jammish says, looking at the floor, not realizing that wasn't exactly what Twinkle had asked.

"You see dear," says Twinkle "it's a fine line. Some people never get near it. Others find it very easy to cross."

Jammish nods, wordless.

His hands move of their own accord, taking off his gloves and his hat. Jammish hesitates and Twinkle nods at the bench where he lay them down. The feline turns his back on the fox, unbutton his social shirt and take out his pants.

"All of your clothes, Mister Wingder."

Jammish take out his briefs, his heart pounding at the notion of the fox seeing him completely naked. Naked, Jammish turn at last, his hands across his groin. There is nowhere to hide.

Twinkle takes a step towards the feline. His vulpine's eyes going over his body, for a moment almost as if they could pierce his soul.

"I hope we can be friends," Twinkle says with a gleaming smile, his bells tingling happily.

The feline nods.

"I know it's hard for you to be here, but soon you will learn to love this place."

He simply nods once again.

"You are cold, Mister Wingder. Come for your bath."

Jammish don't know how to respond. So, he doesn't, he simply obeys. Twinkle reaches for his hand and laces his fingers through his. The vulpine squeezes his grip and Jammish feel his thumb running circles on the back of his hand.

"What are you...?" He asks. "Tiana?"

He pulls them into the long row of showers that dot the far wall. Jammish refuse to let his hand fall from his fingers. He makes the cat turn around and press his back against the tiled wall, pressing his petite body against Jammish.

Jammish feel the fox's arms encircle his lower back, feel the fabric of his dress slide against his naked body. The cat brings one hand to his face and trace his delicate jaw.

"The Mistress allow us to have fun," Tiana says, approaching his mouth from Jammish's ear, sending shivers of pleasure through his spine. The cat doesn't know how to react, how to tell Tiana that he was straight and even though he looked pretty, he had never wished to have sex with another male. Yet, his body kept responding, almost begging for the fox's touch, to feel him pressed tightly against his body.

Jammish let his hand trace over the lines of Tiana's face, marveled at the softness of his fur. Jammish couldn't have stopped this if he'd wanted to.

With his free hand, Tiana feels along the wall for the silver knob and turns it hard to the right. Tepid water rains down on them, soaking his green dress immediately, matting his black hair to his face. Still, Jammish couldn't speak. Tiana pulls his face closer to his own and presses their lips together. Jammish hear his breath catch in his throat, taste his tongue as he probes the vulpine's mouth gently. His eyes close and Jammish feels himself melting, becoming one body, one soul.

Jammish don't care about Twinkle's soaked clothes, and from the passion Twinkle displays with his kisses, neither did he. The water begins to warm slowly as his hands find the hem of his drenched dress. Jammish break their kiss for the time it takes him to lift it over the fox's head before their mouths crash back together. The water pings off the tile floor and Twinkle buries his face into the side of the feline's neck, sucking and licking. He bites down hard and extracts a long, girly moan out of Jammish, his head falls back, his fingers grab onto the muscles of the fox's slim back.

The water stream down Tiana's face, making small rivers on his fur, beading on his short black hair. Jammish can't stop staring at him, this beautiful fairy that had so completely entranced him. So utterly beautiful, the gentle curves of his body, the budding breasts, even the thick collar around his neck. His fingers are unable to stop their explorations of his body. Jammish press them to Tiana's slightly swollen nipples and kiss them gently, bringing out delicious moans of pleasure out of him.

Jammish know that it would be nearly impossible for him to ever again call himself straight after this moment. In that space that needed no speech, that is ruled by their heart beats, their chests pressed against each other. Twinkle raises his face and kisses the feline gently, tenderly, until Jammish want to burst with it.

"You will love it here, we will be able to play every day, you will be my special sissy sister," he whispers as he traces one finger across his forehead, pushing his saturated hair from his eyes. The word "sissy" comes so easily to him, so effortlessly.

Jammish nod and kiss him in return.

Tiana's hands are around his waist already; his eager hands soon were groping his bubbly butt. The vulpine's caged cock presses against his tight, dripping with watery precum. Part of him is scared that this was going to be his destiny, but Tiana's quick hands and warm mouth make him forget it so easily.

All it takes is gentle pressure on his shoulders for Twinkle's knees to bend. Jammish pushes him gently towards the wet tile floor. Tiana's never takes his eyes from Jammish as he got on his knees and massages his cock with a single hand. In a matter of moments, Jammish's hard cock is arched up in front of the fox, visibly throbbing with pent up desire.

"Oh, dear..." Tiana whispers as without hesitation he opens his mouth.

He reaches for Jammish's tights, his tiny hands holding him as the vulpine's eager mouth and agile tongue care for his hard cock, sending shivers through his spine as the warmth of his mouth envelopes his aching cock. His eyes close as he moans with his cock in his mouth, the delicious sound making the cat ready to come in the fox's mouth.

Jammish put his hand over Tiana's head, his hips thrusting into the eager mouth as Jammish loses control of his body, his back leaning against the white tiles. The now hot water splashes against his back and neck, easing any lingering tension. Tiana's deep green eyes stare at him, a look of wonder on his face as Jammish trust inside his mouth, vulpine's hands grabbing at his ass, one hand going for his virgin ass, Tiana's finger penetrating him even as he swallows all of his cock.

"God, you are...," Jammish whispers as he feels the vulpine's fingers penetrate slowly into him, making him shiver, "you are just so damned beautiful."

Jammish couldn't help but moan as he feels his body being invaded like that, his cock still held deep in the vulpine's mouth, Tiana's own little cock twitching inside its cage. The cat's back arches with a shattering orgasm, Jammish feel his hot seed spilling on Tiana's mouth in spurt after spurt, his ass clenching around Tiana's fingers as he feels an orgasm like no other consume him.

Tiana groans as he swallows Jammish's cum, licking the head of his cock to savor the last drops of his cum before sensually licking his lips and slowly pulling out his fingers from his ass. He slowly raises towards the cat, one hand resting on his hips and pulls him into an ardent kiss, sharing his own cum with the cat, the sticky substance rolling through their mouths, coating their tongues as they share a passionate kiss.

Jammish wanted to kiss him forever, wanted their tongues to dance like that until time ceases, Tiana's cock twitching in his cage as he presses it against the cat's tight. Jammish fingers grip Tiana's hair, holding tightly his black hair as the cat press the fox against his body.

"Mister,..." he moans and at that moment Jammish hate that word, hate how it sounds in his mouth.

Jammish eases himself into Tiana's embrace and lead his head back against Tiana's shoulder, closing his eyes. The cat breaths in that wonderful scent of his, clean, deep and girly.

"Thanks," Tiana whispers and kiss his ear. Jammish could feel the sissy's caged cock pressing into his ass and his hips pushing back against him.

"Thank you for everything," Jammish mumbles in reply.

The cat kisses the side of his neck repeatedly.

Under Twinkle's watchful eye, Jammish dry himself as best as he can on a thick, cotton towel, Tiana makes sure to help him reach every place, groping and caressing him all the while. The fox takes out his green dress and proceeds to dry and dress herself quickly. Back in the room where Jammish left his clothes, he goes to put them on but Twinkle stops him.

"Your will have new clothes assigned to you."

Jammish stare at her. "But I--"

A flash from his green eyes and his voice falters.

Tiana continues. "You'll eventually be allowed to choose your own clothes, but in the meantime, they will be assigned to you depending on your assigned task or preference of your Mistress. I can even borrow you some later."

She hands me a set of pink, frilly underclothes then glances at the watch in her wrist. Her lips tighten. Jammish try to hurry, his fingers fumbling with fastenings. With these new garments, he feels stranger and stranger. Bit by bit, he's losing more of himself. Soon he fears he won't exist anymore.

After the pinky frilly sissyshorts panties and the tight pink training bra that is almost see through, Jammish finds a red pleated skirt and a simple white social shirt.

"This is silly," the cat feels strangely naked with the skirt, exposed. The clothes have a sweet and spicy perfume.

"You look great," says Twinkle, kindly.

Tiana gives him a simple black choker, it has the Venus symbol, the symbol of their position and status. Jammish takes it reluctantly, but he finds no wish to disobey. To walk around without any kind of collar would be as if he was completely naked. When he put it on, Tiana gives a large smile of approval.