A Sissy Saga Ch. 08

He balked at the little-girl training bra she offered to him, a delicate lacy thing with a pretty pink bow affixed between the shallow cups.

"I don't really have a reason to wear this kind of thing yet." he protested meekly as she threaded his arms through the straps. But he didn't struggle. He knew the slightest sign of resistance would only cause in him to be stretched across her lap, and Jennifer could be quite pitiless when she spanked a boys bum.

The girl scowled. "Don't bother straining your peanut-sized brain thinking about it, deary. Weakling dyed-in-the-wool girly-freaks like you need to have decisions made for them, and I've decided you're to wear a bra. It'll create a nice effect." She clamped it onto the front of him and fastened it at the back. "There! You look like you have breasts, and that will make you feel like you have them."

The sissy-boy wriggled and squirmed as he snuggled his chest into the diminutive cups, and then his mammoth cock began to extend full and solid, just as he had when he'd first arrived at Fairyfield Grange and been compelled to constantly wear a skirt. His arousal then had been so persistent that he'd been made to endure an elastic band around the base of his penis to restrict the flow of engorging blood until he became accustomed to his gymslip.

Jennifer's remedy this time was less sophisticated. She deflated the offending anatomy with just a couple of sharp taps with a pencil, then covered the drooping item with a pair of G-string panties.

Pulling Poppy to his feet she threw on his shoulders a red nightie, hated it, pulled it off and kicked it across the room, then settled for putting him in a sumptuous chiffon peignoir of baby-doll proportions the bottom of which fluttered about high on his thighs. Slipping his hands through the armholes she eased the filmy jacket around his shoulders. It was periwinkle blue with an enticing silk tie beneath the bosom, and was clearly designed to splay open at the front and reveal the wearers panties.

She tied the silk bow at the front and watched as the delicate, diaphanous material settled against his skin, knowing how thrilling it was for boys to feel dainty and girly and be forced by women to wear short skirts and skimpy dresses. Almost immediately Poppy's tiny panties bulged, and she knew the sissy faggot had developed another erection.

Jennifer cursed under her breath, but this time she chose to try and ignore it and sat him in front of a dresser covered with Limerick lace and a swathe of cosmetics. When she began to apply varnish to his fingernails Poppy offered to do it himself, but she just scoffed. "You're too much of a fusspot. You'd take an entire weekend just to pack a purse."

Whilst the nails were drying some use was made of a Coty box and swansdown power-puff, then lipstick, a lively cherry-red, was creamed onto his mouth, and his eyelashes were masked with mascara. "Keep still!" she snapped, dragging a comb painfully across his scalp. "I'm trying to transform you, you moron, and I can't do it properly if you keep jigging about. Turn your head."

She examined him carefully. "I wanted to make you tres 1930s debutante, all sultry and debonair, but your face is too soft and round, so I'll have to settle for just making you neat."

"What are you doing all this for, Jennifer?" Poppy asked, ensuring his voice was sufficiently subdued and respectful.

"It's time for an important sissy training session, and you need to be dressed correctly." Jennifer explained abruptly.

The boy used his natural coquetry and acted big-eyed and little-girl-lost. "I still don't understand." he said in a voice that was purposely cute and sweet.

His mentor gave him a vexed look to let him know he was being tiresome. "It doesn't matter if you understand or not, because I understand. Don't try pretending you don't you don't enjoy being dressed-up. Just look at your panties with a hard cock in them. You're a creampuff and you love wearing pretty things, so empty your puerile little brain of silly male thoughts and just do as you're told."

"But, why? Where am I going?"

Jennifer lifted her eyes as if appealing to heaven. "Why do all the fairies in this place ask so many fucking questions?"

Crestfallen, Poppy put a finger to his mouth and thoughtlessly contemplated sucking it, at which Jennifer grabbed his hand and delivered a sharp smack to his wrist. "I've just lacquered your nails, you effeminate cretin. Sit still. You're going to see my mother in her bedroom, that's why I'm taking so much trouble with you."

She gave the risen shape in his pants a cruel scrape with her pink-tipped fingernails and made him squirm. "Mmm, yes! Little Poppy loves being a girl, don't you? Mummy's taken a fancy to you since you made yourself so prominent chasing after that ghastly creep Judd."

A misty look entered Poppy's eyes. "I loved Judd." he murmured in a beatific voice.

"Tosh! You don't 'love' anyone. You flirt with everyone and fall for any creep with a hard-on. Judd as the brains of a hamster, he couldn't even pull the clothes off you without getting caught."

Poppy pouted. "I'm not a prick-teaser, Jennifer."

"No," the girl agreed, "You're more of a prick-pleaser I'd say. You like men, but you're not strong enough to be a man yourself, so you have to take cock up your little sissy arse."

She knew he wasn't alone in his homosexual interests. The entire school was composed of effeminate panty-boys only slightly less shameless than he was. They were all full of girlish mannerisms; wafting hands, cheeky smiles and light skipping steps, and no harsh words were needed to compel them to hold hands when taken out on nature walks. The use of cosmetics was banned during school time, but they usually risked a hint of perfume, and early in the day each of them would exude a delicate floral fragrance.

They were always clean and neatly dressed too, which was in itself uncommon among young men, and while such a thing was demanded of them by her mother she fancied there were other reasons why they spent so much time bathing and tidying their hair. They did it for each other, because they wished to seem alluring and desirable to their classmates and dormitory friends.

They always looked so endearing and blameless - angelic almost - but she knew there was unlikely to be a virgin arse among them. Quite apart from the depravity of old Hardwick she knew from questioning Abigail and the prefects that when lights-out was imposed in the dormitories at the end of day the emasculated little bitches were at each other like cats. Cock-sucking and mutual masturbation was rife, and anal sex commonplace. They were absolutely without morals when the mood gripped them.

She had no use for their contemptible pricks herself, but she was perversely turned-on by watching queers perform, and just the thought of them doing things together made the lips of her proud young pussy pout against the stretched tightness of her panties. It didn't matter if they were full-blown homosexuals or had merely been conditioned to it by being deprived of the companionship of suitable girls, such bad boys needed constant correction.

She pulled up his hands to examine Poppy's lacquered nails. "Nice fingers, do you ever wear rings?"

"I do when I'm allowed."

"I think I've got some that will fit you. Only dress stuff, not real silver, but good enough for a girl's first date."

She had plenty of rings; enough to provide one or more to each of his slender fingers, and Poppy beamed at being decked-out with so many baubles. Because she was preparing him for her mother Jennifer took inordinate trouble garnishing him further. She screwed onto his ears the prettiest earrings she possessed; two teardrops of opaque jade that seemed imbued with an animation of their own and shimmered when Poppy made the slightest turn of his head. And finally shoes, silver sling-backs with heels so high the youthful princess was practically on tiptoe and felt in danger of toppling forward when she made him stand up.

Being swathed in perfume and effeminate attire excited Poppy. The gentle tug of the flimsy baby-doll on his shoulders and the soft fabric caressing his belly saturated him in femininity, and as he posed for Jennifer's inspection he gripped the hem of his diaphanous negligee at either side and slowly rotated, a pantyboy in girly-land, seeming oblivious to the tenting of his pants. "Does it look okay?" he asked, "It feels nice."

***

Jennifer accompanied him hand in hand along a passageway, if not quite like a girlfriend then at least like a big girl caring for a smaller sister who was simpering and squirming about. Earrings swung against Poppy's neck and bangles slid along his forearms, and he was in exactly the right frame of mind for being cared for and adored.

"Will I have to see your mum - I mean, will I have to see Miss Hancock, alone?" he asked.

The girl gave the prodigious sigh of a person relieving themselves of a burden as they approached a door at the end of the corridor. "You're not a six-year-old, even if you enjoy acting like one sometimes. Be a bit grown-up about this for goodness sake. I'm leaving you here. Just knock at the door and await permission to enter."

Left alone, Poppy tapped lightly on the door before him with some trepidation, and listened for a response. The voice that bid him enter was matter-of-fact and not altogether reassuring in its tone.

Miriam Hancock's bedroom had a high flung ceiling and mullioned windows looped with heavy crimson curtains. Modern cupboards lined one wall while a chaise longue upholstered in red satin together with an old fashioned chair stood by a walnut spinet that had been converted into a dressing table. With its western aspect and pine panelled walls the room made a gracious setting for the antique four-poster bed with spiralled mahogany pillars that had dominance. The main house had been built in the 1830s, but the bed predated everything around it by a hundred years, and Miss Hancock maintained that it came from the original manor. Everything in the room declared opulence and its occupants appreciation of fine things.

Poppy entered tentatively, pausing just inside the door, eyes aflutter. The headmistress stood as a dark silhouette against the far window and didn't move for a moment, even when the soft click of the door told her it had closed. Then she swung about, hands thrust deep into the big pockets of a white bath robe, her eyes glittering.

She was a woman so tempered in her movements that at times she appeared to do everything in slow motion, and that was the effect she gave as she glided towards him at that moment. The image she presented was one he'd never seen before. Her rich brown hair was pinned up in swirls as usual, but her fine arched eyebrows had been darkened to emphasis the fairness of her skin and her lips seemed unusually sensual. It was also the first time he's seen her so close to being undressed. Her robe was pulled open at the top and he could see the cleft between her breasts, and he suspected there were few clothes beneath the coat.

Blinking rapidly, he stood transfixed, fingers clutching nervously at his chiffon peignoir and only relaxing to flourish the hem in the expected curtsy before pulling the fragile fabric close to his body.

As she moved towards him Miss Hancock observed the doe-eyed sissy shrewdly. Stockings and suspenders looked wildly incongruous when worn with a negligee, but Jennifer always did have a taste for the dramatic and loved dressing up boys as French tarts. That night Poppy's figure was displayed to perfection by the way her daughter had adorned it. Still only eighteen-years-old his face was delicate and dimpling and extraordinarily pretty, and with eyelashes fluttering and hair shining he was the image of a sweet girl on the verge of womanhood. Then she caught a glimpse of the tumid thrust in the front of his panties as his inappropriate big dick strained forward and a slight smile turned the corners of her mouth. Sweet, but not so innocent, she thought. Poppy had a reputation for being easily stimulated by frilly things.

"Jennifer's dressed you in a stunning fashion, Poppy. So beautiful, so sweet. You wouldn't be out of place in a sultan's seraglio and it's just unfortunate I've yet to cultivate any contacts that serve the orient. Did Jennifer explain why she'd dressed you like this and brought you here?"

"She did tell me," the she-boy admitted, "but I didn't understand most of it. And she made me wear a bra, and I don't understand why she did that either."

Miriam paused to consider the not quite unconscious turn-away of the boys head. He had charming dark eyes, at once sparkling and shadowy, a pert nose and an impetuous mouth that lent a touch of naivety to his manner. It contrasted amusingly with what she knew of him, but of course she knew he had a talent for laying-on expressions.

Since her meeting with Lady Diana she had been preoccupied by the threat the woman posed to her and she needed to relax, and at that moment Poppy was her ideal person to relax with. Slipping an arm about his narrow shoulders she steered him towards the four-poster. "The thing is Poppy, you can't remain at Fairyfield for ever and I'm bound to sell you soon. You will be employed by a person of good standing as a houseboy or upstairs-maid, or perhaps as a personal dresser or companion. Whatever role you're given you're certain to be used in a recreational way too. That being the case, there is a need to assess you."

Poppy blinked hard. If what Jennifer had said was a mystery to him, her mothers explanation was just as unfathomable. "Recre-what, miss?"

A smile touched Miriam's face. The so-called assessment was a frivolous excuse of her own devising. She had become keenly aware of his sexuality that morning when he'd been brought before her in little more than stockings and a garter-belt trimmed with lace. She'd felt aroused by his near nakedness, and when aroused Miriam could be consumed by passion that raged like an inferno. For months such things could lay dormant until some small inexplicable thing awakened them; the glimpse of a bare thigh, a pretty smile not meant for herself, an inadvertent glance or a satisfactory conclusion to an aspect of business. Reasons were varied and unpredictable, but whatever they were when the passion came there was no peace until it was sated. In sexual matters she much preferred the company of other women, but now and again she had the urge to spin off at a tangent and try something new, and Poppy was an ideal subject for innovation.

She seated herself on the edge of the bed and smiled affectionately as she brought one hand up to touch his cheek, the gesture tender. "Recreation, Poppy. Recreation as many facets," she explained pulling him down to sit at her side. "Sex for instance is useful in procreation, but it can also be pleasurable play. You know about sex, don't you?"

He smiled weakly in return and gazed down at his hands. "A little bit, miss."

"More than a little bit I think. Your dormitory friends are forever wanting to sample you are they not?"

"They're wicked, miss."

"Yes, wicked indeed, but you're very tempting, and I don't doubt you taste as delicious as you look." Her hand dropped to the bow on his negligee and dissolved it with a deft tug of her fingers. What she was contemplating was outrageous. She knew what she intended was immoral and unnatural, but she didn't care.

Poppy stifled a gasp. Looking up he became conscious of desire in the face of the headmistress, saw the sensuality in her partially open lips and heard her quickening breath. He'd seen such expressions on men in the past when they looked at him, but this was different, she was a woman.

Her eyes studied him, then she kissed his eyelids, his cheeks and his chin before moving to his mouth where two blends of scented rouge mashed together. Slowly, almost lazily, she rolled her mouth against his lips.

"Ooooww, Miss Hancock!" he twittered. Poppy was promiscuous and he was a manipulator, but he had nothing in his repertoire with which to counter the amorous attention of the headmistress. Alarmed, he meekly tried to resist, but only succeeded in falling backwards on the bedcovers where his petite torso undulated like a snake. His heart beat so much he thought it may explode as she lay down beside him and stroked the negligee away from his shoulders.

As she disrobed him she dictated her injunctions. "Keep still. Don't move. You think you know why you are here, but you haven't any idea. You may think I want you to give it to me, but you would be wrong because I'm going to take it from you. Take it, do you understand?"

"You have a young man's body, yet you constantly manage to flaunt it in the manner of a girl." Unimpeded by any need for modesty she reached low to brush the skin of his belly, then blatantly caressed the hard-on tenting in his panties to make his cock thicken under the pass of her pearly fingernails. "You like that, don't you? Does it feel good? Is this what you like the boys to do when they entice you into a cosy corner?"

Her eyes burned into his, her voice had become honey-coated sex, and before he could respond she kissed him again, her mouth crushing his own in the ferocity of passion while her tongue filled his gasping mouth. Then her mouth glided down over his throat and around his neck and he became aware of her fingers moving up his back. The woman's excitement had become strangely contagious. A pulse beat in his slender white neck and his chest rose and fell rapidly. He was breathless, almost panting, and his throat felt tight as the hook-and-eye fastening of his bra was released. "N-no please. Oh miss, you mus - mus ..."

How delightful, Miriam mused. The boy who had expressed such distaste at being made to wear a bra was now like a virgin little girl on her first date, pleading for her not to remove it. Off it came anyway. The skimpy garment went limp and she scooped it away from his chest to reveal two lovely girlish nipples. Pink and puffy and begging for kisses.

Dominated by the larger physique and greater strength of the headmistress and unable to control what was happening young Poppy groaned in capitulation and pushed his chest up to meet her avid mouth as it attacked his body, his hands clamping onto the back of her head as she feasted on him.

Intent on tonguing and suckling his boy-nipples, Miriam pulled the flesh forward and made the pale pink teats pointy before taking each into her mouth in their turn, drawing in her cheeks to make the swollen glands balloon and tugging at the tender buds with her teeth. In the midst of sucking on his breasts Miriam tucked a thumb beneath the elasticised string of his tiny pants and eased them down over his thighs. His penis, long and swollen, lolled against his thigh, but she shoved it aside to concentrate on stripping off his knickers.

Finally, having enjoyed some gratuitous foreplay she took hold of Poppy's hand and pulled it down to press at her robe where it concealed her groin, and the contours of what lay beneath caused his arm to jolt as if he'd received an electric shock.

"Keep your hand still for a moment," she told him, "Feel the shape down there. Do you know what it is?"

He did know. Confused, he could only gasp, embarrassment mixed with wonder. Miriam shook his hand away and slowly stood up, and the elegance that she'd taken care to nurture so carefully over the years lost none of its attraction as she removed her robe. Her body was statuesque and firm, clad only in a black basque that made a show of two exquisite breasts with peek-a-boo nipples. Beneath her pinched-in waist fine hips curved round to accentuate the additional accessory she'd installed at the vee of her thighs. There, looking ominously businesslike jutted a well proportioned replica penis sculptured in realistically veined pink latex. It was affixed to her closely cropped Mons Venus in such a way it almost seemed part of her anatomy, the illusion only betrayed by the buckles and black leather straps of the supporting harness. Rearing up potent and full of promise it showed itself to be enhanced by a heavily laden scrotum, only a polythene sack, but a thing that swung perversely against the soft white flesh of her thighs like a party balloon half full of water.