A Sissy Saga Ch. 04

Such sweet looks. Such innocence. What reason could she invent to punish such an individual?

"Do you know why you're here, Poppy?

There was a breathless quality to the pupils voice as he uttered the first words since his arrival. "When I'm told to come to this room ladies always smack my bum - sorry miss - I mean, bottom, Miss."

"I expect that's because you're naughty. You've probably been naughty today."

She wanted to incite some guilt in him that would dismiss her own uncertainties, but instead she faltered. The soft mouth pouting with apprehension, and the shine in his large appealing eyes aroused maternal instincts that were alien to her nature. She became aware of a tightening in her stomach, a symptom of a growing fear that she may not be up to what that infernal headmistress expected of her. Then, suddenly the precious boy failed to conceal a fleeting slant of mouth and sideways glance that betrayed the talent that had so nearly been her undoing.

Cats eyes! she thought as she reassessed the glow about his face. Yes, there was definitely something feline about Poppy at that moment. She was being tricked. The youthful androgyny was deliberately ruffling her emotions and manipulating her with playacting worthy of a thespian. His versatile smooth face could conjure up an expression to suit any situation, and change with the speed of an express train, and that was probably the ability for which the sly Miss Hancock had selected him.

She took a deep breath and leaned back. No one was going to kid anyone, anymore. "Naughty girls need to be punished, don't they?"

"Yes, miss," Poppy agreed, shuffling his feet, "But I haven't done anything wrong."

"You awoke with an erection this morning, and you played with yourself and did a cummy in your hand without asking permission."

"Oh no - honestly miss, I didn't..."

"Stand still, and don't argue," she said curtly. With a swish of skirt and stockings she turned and moved a token distance away from a delicate situation. This was more like it, the real Emma Twist was back in the driving seat, she thought as a tingle arose in her breasts and heat besieged her lower down. This was why she wanted so desperately to work at Fairyfield Grange, and she was now ready for a little innovation of her own.

She went over to the travel-bag she carried with her and took out an hairbrush, a cheap plastic item, but broad and flat and ideal for her purpose. The back of a hairbrush would be classified as a paddle in Miss Hancock's list of approved tools, and plastic was the perfect material for chastisement. In her experience it provided keener impact than wood or even ivory.

She gripped it in one hand and tapped it into the palm of the other as she returned to the boy, slowly walking around him and ensuring it passed under his vision. "Well, my little lady, it's time to pay the piper."

Poppy gazed at the hairbrush in genuine dismay. "Please don't smack me, Miss. I'll do anything you want if you don't smack me."

His words were evocative and calculated to stir the imagination, and Emma could appreciate how successful they often were. Oh, he was good! Such a gift for diversion deserved a place in some theatre, but she was wise to him now. She pointed with the brush to an horsehair sofa. "Sit down."

Brushing close to him she became aware of an emanating perfume, a fresh floral fragrance of the type so often favoured by young girls. She decided she liked it. It was distinctive, subtly teasing. Whatever it was it stimulated. "Lean back and raise your legs." she told him.

"M-my legs?" The boys voice was almost inaudible.

"Don't give me any trouble or I'll make things twice as hard."

As he eased back and reluctantly brought up his knees the woman leaned forward and grasped beneath them, hauling back until the undersides of his thighs and the seat of his knickers were exposed. "That's it. Stretch your pretty legs up, and don't bring them down until I say so. I'm going to smack the backs of your thighs and your bum cheeks quite sternly, but you'll only get extra if you struggle."

His young bottom swelled firmly inside the tight white pants, but Emma tapped the flat side of the brush against the bare skin around the rim. "Now Poppy, as you're aware misbehaviour will always be met with punishment, and since you've been trying to trick me ever since you came into the room, punishment is what you're going to get."

At last she was able to apply the hairbrush, and she smacked it lightly against the boys bottom.

"This -" smack, smack! "- is the part of anatomy which is, as it were, 'tailor-made' to receive an award for misbehaviour." CRACK! A blow descended onto the fleshy part of his upper thigh. "But other areas can be just as useful."

Holding his legs tight she brought down two more blows, one for each leg, then two more where plumpness showed around the elastic edge of his pants. Poppy squealed and wriggled, but was no match for her strength. Placing the hairbrush down for a moment she dragged the gusset of the undergarment into the furrow of his bottom to expose the fullness of his bare little behind, and then came the staccato cracking sound as the brush once more resumed its task. Splatt! to the left. Smack! to the right Wallop! dead centre, to visit both cheeks at the same time.

The brush made several trips up and down the back of his thighs but paid greatest attention to the base of his buttocks. In fact it visited every inch of the tossing backside, lighting blaze upon blaze on the sissy's bottom cheeks. Pale skin reddened quickly under its tutelage and any thought of stoicism soon vanished.

"Ooow, aah, wheee!" The boy wailed as a rosy hue blossomed on his skin and his small buttocks twitched. The hairbrush swooshed again, a leisurely stroke, but the impact keen enough to make his legs jerk. "Nnnarrr!"

"You deserve it." said Emma Twist coldly.

"I know -B - b - but - OUCH! - my b-bottom's so sore - OWW!"

Nothing he did could ease his plight and his head rolled from side to side to become a tearful vignette of discomfort. Emma patted the crimson bouncing backside and decided to give it a final wallop. WHACK! He jumped sharply, "Ooooch!"

At last she released him, and leaving him sobbing in distress she smiled grimly, delighted at the sight of his half-bared red bottom. She felt better now, and calm enough not to make obvious the excitement she felt inside.

So far, so good. Now the next step. She'd show that fussy headmistress just how good she could be at handling sissy boys. She'd let lose some of the passion she'd been forced to hold in check most of the time elsewhere when she took him across her knees.

The boy sniffed and rubbed his eyes.

"Do you have a handkerchief?"

He groped into the little pocket on the front of his skirt. "Yes. Yes Miss."

"Well wipe away your tears, I haven't finished with you yet." He was a succulent little charmer, she decided. Far better he was in a place like Fairyfield than out in the wide world where unscrupulous men would be forever be trying to coerce him into their beds. It occurred to her he was probably homosexual anyway. He just had to be.

"Are you?" she asked. "Are you queer?"

He feigned surprise. "I-I don't know what you mean, Miss."

"Do you enjoy being admired by men?"

"I like to be admired by everyone."

She tried another tack. "Do you like being a girl?"

His eyes flashed a wary glance. "I'd be in awful trouble here if I said I didn't."

"And so, if I asked you if you were a girl or a boy, what would your answer be?"

He dipped his chin, but continued to look up with cautious eyes. "I suppose - I suppose I'd have to say I was a girl, miss. I'd have to say I'm a girl with a cock - erm - I mean, a girl with a willy, Miss."

"And do you like to stroke your 'willy' against other willy's in the dark of the night?"

His mouth fell open in a gesticulation of horror. "Miss! We're not allowed to do things like that at this school."

Emma tutted. He'd cleverly avoided admitting anything, but just wait until she had him over her lap. Then he wouldn't be able to dodge giving her a straight answer. She'd make him shout it out.

"You're in for a nanny-spanking before I'm done with you, and for that you'll need less clothes, so get undressed."

The she-boys wet eyes blinked, taken by surprise. "Please miss. I don't think it's right. Only first-termers should get spanked across ladies laps."

She favoured Poppy with an avuncular smile. "And you're not a first-termer?"

His bottom lip protruded and he shook his head. "I've completed two terms here. I'm nearly nineteen."

A protest was to be expected. An over-the-knee bare-bottomed hand-spanking was the most humiliating because it was the most childish, and with an airy roll of her eyes Emma pretended to give the matter some thought before making a pronouncement. "Well, I think it only proper that sissy-creatures should just do as they're told. So you WILL go over my knee."

"Oh - erm, yes miss. But please, miss - ladies never make me take my clothes off, not all of my clothes anyway." he protested mildly.

Emma's lips tightened in a show of irritation. The faggot's repertoire of expressions included an adorable little grimace so charming she felt tempted to softly bite his pretty mouth to punish his insubordination. There was no doubt in her mind that this particular 'schoolgirl' got spanked a lot. Grabbing him by the wrist she pulled up his hand and deliberately bent his fingers back. Gorgeous! He didn't even try to fight her, he simply grimaced with pain.

"I don't know what other ladies do, and I don't care. Get undressed."

Poppy's small shoulders slumped forward in an attitude of submission and he pushed the straps of his gymslip down, brushing away a stray tear before starting to unbutton his blouse. Standing up he shook the garments onto the floor and revealed himself in his underwear - a little halter-top worn high on his chest like a substitute bra, and a pair of hipster pants that clung to him like a dream.

Emma surveyed his body as unobtrusively as she could. Slender and blemishless, with skin so pearly white it was almost translucent. His tummy, flat and sensual, quivered slightly, and she noticed a small gold ring in his pierced bellybutton, while his waist was narrow, accentuating his hips and giving him an element of girlish grace. Only the plump coiled shape in his panties destroyed the illusion of him being a real female.

She rose to her feet and stood close to him, raising the skimpy halter-top just enough for his nipples to peep out beneath, tender sprouting things, the tips pouting upward from pale firm flesh. Men would fight each other to kiss them. A small gasp rushed from his mouth as she gently tugged them with her fingers, but he didn't move away. Could it be that he actually liked having his nipples caressed?

He was a gay-boy without doubt she decided, and a bimbo too. Fully clothed his face was beguiling enough to be taken as a girl, and many of his mannerisms - the way he turned his head, the poses he struck, the expressions he favoured - all hinted at femininity. Stripped down to his underwear there was no doubt to his gender, but little doubt either of his inclinations.

"Miss Hancock is quite right to dress you as a girl. Why should ladies have to put up with clumsy boys in ugly trousers when they can have dainty girls tripping about in revealing short gymslips and bare legs - obedient girls who'll do exactly as they're told? You always do as your told, don't you Poppy?"

The she-boy nodded at once.

"Good! Take your knickers off, there's no point in being modest with me."

The boy wiggled his hips and peeled the pants down over his legs. "My bum's very sore, Miss. You won't spank me very hard, will you?"

Emma watched, in transfixed in fascination, and didn't even bother giving an answer. Only her eyes followed his movements. His thighs were smooth and hairless, his pink balls, no doubt brimming with girlish-goo, hung beneath a remarkable penis. It was immense, fat with a purple tip and dangling almost halfway down to his knees.

Her own pants were becoming wet, and she felt an odd fluttering inside her stomach. The unrestricted view of his incredible over-endowment was erotic and provoking and she had to resist an urge to grab at it. Another trap she realised as she reinstated her composure. She had been warned. Any indication that she considered him male would ruin everything.

Sitting down once more she pushed up her sleeves, hiked her skirt to reveal bare skin and garter straps above her stocking tops, then patted her thighs. Soft yet stable, they formed more than an adequate platform for the task ahead.

***

Miriam Hancock found herself pacing restlessly across the floor of her parlour-office, her usual self-control and clear judgement under attack. Knowing that a person should remain unpartisan when selecting staff she nevertheless found herself wishing for Miss Twist to succeed. Her school was lacking in intellectual minds, and apart from Jennifer, there was no one she could talk to at the level she craved. From the moment she'd met Emma Twist she'd been attracted by her feisty nature and good looks. She really was an enchanting young woman, and it was refreshing to come across a person so eager to experience the new and unfamiliar - so thirsty to quaff the unique pleasures that Fairyfield Grange could offer.

To distract herself she threw open the door and turned her attention to the wide main entrance hall and the polished banisters and sweeping stairway that comprised its heart. Outside it was a brilliant spring morning, and sunshine filtered through the fanlight over the main door, projecting the colours of the stained glass into the house and making weird patterns of light on the floor. The wood panelled walls and rich mahogany barley sugar balustrades of the stairs lent the scene a kind of regal splendour. How beautiful, she thought. How breathtakingly different it was from just a year ago.

In its heyday the Grange would have been staffed by forty-two people, including fourteen gardeners, and every portion of its interior would have had a skivvy assigned to its upkeep. Now she could only afford three part-time gardeners and a handful of local women to clean the rooms at ground level. Still, she'd overseen a vast improvement on her inheritance and that was reason enough to congratulate herself. Initially the transformation of the decrepit country house into a residential school had seemed a formidable task, but by nature she was an opportunist and totally unafraid of taking chances, and as time passed the easier things had become.

There were numerous well-proportioned rooms on the ground floor, including a huge kitchen at the back. Upstairs were bathrooms and ten bedchambers of varying dimensions, some of which were easy to convert into classrooms, while others served as apartments for staff accommodation. The third floor, under the eaves of the roof, had several attic-rooms that provided adequate if somewhat cramped dormitories for three dozen resident students. Amenities could be extended even further when funds to refurbish the still unused east-wing became available.

She thought of the times before she'd come to Fairyfield, of the boredom, the narrowness of existence and the dearth of anything to inspire her. What marvellous changes her new venture had made to her life, the possibilities for wealth and social position had never been greater. In her fine mansion she felt invulnerable and in control.

Suddenly her attention was drawn to a clicking of heels as a youthful girly-boy, bare legs flashing beneath the short skirt of a gymslip, appeared in the hall, making his way towards the stairs.

"You - come here!" she demanded.

The figure altered his direction at once and made a timid approach. His blond hair was brushed neat and it gleamed, while his face was scrubbed to a pristine shine. He became rooted to the spot in font of her, quaking and swallowing hard, but remembering to curtsy.

"Yes Miss." he said, bobbing.

His hair was honey blond and simply arranged with pink ribbon threaded through the locks, while his petite face was extremely pleasing, its best features being dark eyes, well open and straight gazing. His figure was trim and pleasantly lacking in height.

"Name?" she snapped.

"A-Amanda, headmistress."

Ah yes, she remembered him then. Amanda was the most well behaved sissy in the school, obedient and sweet and as cute as a button. He was also a victim of skulduggery. Due to inherit a fortune at his coming of age, his reptile of a mother wished to ensure her control of him by having him feminised and trained to serve as a housemaid in his own mansion. She wanted the young man to be a hot little teenage she-male who constantly waved his soft, sissy bottom at men, thinking that if he always had a big cock in his bottom he'd have little interest in pursuing his legal rights. While in a classical frame of mind she'd suggested Cassandra as a name for him, but the mother, being an unread philistine, had preferred instead a lazy pedestrian name. A name she'd once given to a goldfish.

"Why are you out of class, Amanda?"

"Mrs Pardoe excused me to go to the loo, but the one upstairs is crocked - er, broken - it's not working miss."

"Then you should have gone up one floor, not down. You've been at Fairyfield long enough to know the ground floor is out-of-bounds until 10 am."

Amanda woefully glanced at his wristwatch. "Please Miss, it's 11 o'clock."

Miss Hancock riled, angry at being so out of touch and made ridiculous. "Don't be impertinent. It seems you've yet to discover the consequences of being cheeky to a lady."

"Oh, honestly, Miss. I wasn't..."

She knew his response had been made in innocence, but she'd been seeking something to fill her time until Miss Twist had finished with Poppy. And he was a sweet thing. "Get inside my office."

The young sissy stumbled through the door and stood bewildered until nudged towards a nearby carver.

"Kneel up on the chair." the headmistress ordered. She closed the door as he positioned himself, then moved up behind him to raise the back of his skirt and tuck it into its waistband. Amanda peered over his shoulder fearfully as the seat of his knickers went on show.

"Are you going to spank me, Miss?"

"Yes, of course. Maybe then you'll learn not to speak out of turn."

Inserting her thumbs into the waist-elastic of his pants she dragged them down to expose the small bare mounds of his buttocks. Charming! She thought as she watched them judder slightly. Few artists in their prime could reproduce such translucent skin charged with such a delicate hue of pink. Most of all they would be frustrated by that imponderable thing, the virgin bottom, fresh and chaste. So attract. So seductive! So very smackable!

"Please Miss Hancock, I really don't think my mother intended for me to have my pants taken down."

"Nonsense! She gave approval when she brought you here. Are you shy about displaying your bottom? If that's the case something must be done about it." She took a moment to study him. His eyelids had a warm pinkish sheen and the lashes were long and sweeping, and when they fluttered they made him coquette without any conscious effort.

"You're a pretty girl, Amanda. I'll speak to Mr Hardwick and insist he includes you in the aerobics team that will perform on the lawn on Open Day. That means you'll need to attend detention with Mr Hardwick some evenings of course, and on such occasions you'll wear nothing but a tiny posing-pouch. That will certainly cure your silly modesty."

Palming the smooth contours of his bottom speculatively she glanced about for a slipper, then changed her mind. A hand would suffice on this occasion. Yes, intimate contact, skin on skin. Slapping his small unclad behind would be rather lovely.