A Sissy Saga Ch. 08

Poppy had seen countless erections before and the cock sprouting out from the loins of Miss Hancock was impressive. It made her seem even more authoritative then normal, and awesome too - powerful and utterly in command.

Miriam usually held her emotions under tight restraint, but exposing herself in such a shameless way excited some wanton behaviour, and she shook her hips to made the prosthetic shudder. In no more than a few seconds the demure headmistress of Fairyfield Grange had taken on the attributes of a randy stallion, and a certain expectation shone in her eyes as she contemplated the petite, lissom young man spread before her. Eyes misted over, lips slightly agape, he looked tantalisingly like a real girl waiting to be ravaged. Certainly he had a remarkable cock and handsome balls, but she chose to ignore them completely.

"Spread your legs nice and wide." she told the awe-struck she-boy. "I know sissies need lots and lots of sex, and since I'm sensitive as to how females mystify you I intend to make love to you like a man."

Poppy shivered and gazed at her in dumb disbelief. Her - the headmistress! A woman. She was going to make love to him ... she was going to fuck him.

Miss Hancock bypassed his amazed expression. Twin vices caught his ankles. Big hands. Her hands. Long, strong fingers and supple palms, lifting his slender, smooth legs up and pushing them back around his ears to a level that caused the dimple between his buttocks to give a show. Being hairless and smooth such a position allowed an unrestricted view of his anal ring clenched in apprehension, and after first drenching her extension with baby-oil she then dosed a good deal onto Poppy's tense little bum-hole.

"Right! All ready?" Miriam muttered in a sibilant hissing voice, "Stay on your back and spread your knees - let me get in between them."

Breathing hard, stomach taut, Poppy gazed between his splayed thighs like an anxious girl, then he flinched as the headmistress loomed over him and something cool and hard furrowed indecently between his buttocks, screwing about and searching for a way in. "Unh!" He groaned and his eyes opened their widest as he felt the thing find its target and press forward. "Miss - Miss Hancock, ladies shouldn't do this to boys." he wheezed helplessly.

Her reply was hot and treacly. "But you're not a boy, you're a girl, Poppy." She pushed with her thighs and felt a slight give in his ring, and when she maintained the pressure his tight little buttonhole gave way and she was able to force the head of her cock beyond his sphincter.

"Wooow!"

"There we are! You see, you are a girl aren't you Poppy. Admit it."

Poppy's whole body quivered and contracted, and then ... jerk ... jerk ... a panting, 'oooh, oooh, aaah! and a sob. "Yes, miss. Yes, I'm am a girl."

She grasped the soft curves of his bottom, rotating them so they created a warm intimate friction, then the spearing tip of her apparatus bullied further forward, making Poppy moan as the bulbous head and thick shaft stretched him and a familiar sting assailed his insides. The gate once breached offered no more impediment, hands clawing the bedcovers, he accepted everything given, gripping the hefty lance with his anal muscles and squirming against it. Jubilantly the headmistress dug her fingers into his soft flesh and humped the clinging anus to make it slid down the length of her cock, leaning slightly back to watch the tight ring squeeze along the shaft.. Then she went down on him, ramming him energetically and enjoying his little moans.

"Oh, miss - ooh, Miss Hancock, ooh. It's big - it's too big."

"Don't be so melodramatic. I suspect its size is rather modest when compared with some of the men who've used you in the past.." Skewering him another inch she licked her lips. "That's it, let me do it. Let me fuck you like men fuck you."

"Ooorrrommmh!" Poppy's voice rattled rather than gurgled in his throat as he twisted, rolling his head back on the pillow and pointing his chin upwards. Miriam knew him to be a play-actor, and whilst steeped in confusion and yielding in her embrace she suspected his little utterances of protest were no more than the inane ramblings of a girl surrendering to a new lover.

She held him steady, lowered her hips further and squeezed more of her plastic cock into his pliant backside, contorting her whole body with delight as the strap-on glided forward and sank in up to its balls. When she was certain his rectum was packed full she pushed herself up slightly and began to fuck him gently, gyrated her hips slowly to make the thick dildo stretch his helpless boy-pussy in every direction. The sissy gave a little buck with each in and out, intensely aware of Miss Hancock's strong thighs pressing between his legs, and even more aware of the pitiless dimensions of the thing she was causing the burning feeling inside his greased bum-hole his initial show of distress became increasingly vocal.

"Oh - h - h!! Miss Hancock! Oh - h - hh! You're killing me - you - are - killing me! Ah - hh - Oh! Oh! Oh!"

Poised directly over him Miriam used the expertise she'd gained from encounters with innumerable young women, supporting her upper body on her elbows and undulating her thighs in a supple easy motion to ensure her cock moved smoothly back and forth in his anal tract. Her ample breasts all but spilt out from her basque as she pressed them against his chest, but having established a rhythm she had become negligent of such things. Her face became a mask of rapture as her hips arched back and forth to skewer him forcefully, harder and faster with each stab, going right up until her facsimile scrotum was slapping against his conquered bottom like the ball-bags of a randy stud.

Lost beneath her and trapped by her all-encompassing physique Poppy clutched desperately at her hips, and without actually planning to found himself worming his bottom in response to her movements. His mind seemed to melt. The plastic thing had started to touch a mysterious erogenous place inside him that he'd once been told about, but had forgotten the name of, and was beginning to provide a lovely feeling that made him want to please. - made him want to do whatever the headmistress wanted to do. Oozing and shimmering with her he found himself groaning as he lifted his body to bounce in tempo with the relentless beat of the phallus moving piston-like in his fully compliant rosette.

"That's it, darling," encouraged Miriam, "Wrap your legs around my waist, move your cute little bum and hump with teacher." She settled down on him, moulding herself against his smaller frame. Because she was taller her chin nested on the top of his head all she was aware of was the sensation of Poppy's face and cheeks pressing into her neck and the roll of his bottom pinned in place by the short, intense strokes of the object in his anus.

"Oomph!" Poppy whimpered as his bottom repeatedly rocked in clasping waves, slavishly pursuing the woman's wild thrusting. "Oh, miss... You want... I want... I want to be your girl..."

Miriam sucked in her breath. "I know you do, and tonight you are my girl. Get ready for when teacher shoots." With each forceful push of her thighs the base of the apparatus pressed against her to send tentacles of lustful sensation to wrap about the tiny bud between her legs. She was fucking a beautiful boy-arse and could feel what she was doing. She could feel it through the inanimate object that connected them, and combined with the psychological thrill generated by the unacceptable act she was engaged in it was beginning to make her quake. As she fucked him harder and harder she became breathless. The tingle and throb in her clitoris was no longer under her control and her pussy-flesh began to palpitate.

"Aiieeee!" She squealed softly, her body jerking and trembling against his. "Here you go, sweet thing. Take it... ooooh... lovely... take it... All up in you. Let me fill you with cock-cream..."

As she orgasmed one hand reached down to squeeze her facsimile testicles and send a streams of facsimile cum along the shaft of her appliance, hosing into him far more copiously than any man could, pumping spurt after spurt of replica semen into his jerking body... using him... making him her whore... filling him up... filling his sissy-arse with spunk.

Her fingers squeezed ceaselessly for a short while, massaging her improvised ball-bag until its entire contents had poured into the clutching tissue that still clung diligently to her sliding penis, squeezing quickly until the bag was empty. Movement didn't cease until Miriam was exhausted, and Poppy was fully fucked.

Afterwards, when they had thrown off the lassitude that follows heady fornication, Miriam eased out her cock and rolled away. She then slumped content, looking at Poppy with her dark shadowy eyes. "Your big willy is still erect, dear thing, so you may milk it whilst I cuddle you. But make sure you don't get any of your sticky spermies on me."

***

Hardwick awoke as he always did, early. Six thirty in the morning. The curtains were drawn, but not completely, and through the gap between them the morning air flowed in, fresh and invigorating. It was light, and the sky was clear in promise of another fine summer day, so for a moment he lay drowsy and relaxed, steeped in the pleasure he had known the evening before.

He ran his fingers through his own taupe locks which he always parted on the wrong side, then reached out and touched the body beside him just as he would have touched a piece of porcelain or sculpture, just for the pleasure of feeling the shape and texture beneath his fingers. His light caress didn't disturb the sissy, and when he withdrew his hand he still slept.

The gym-teacher was generally a contented man, which surprised many people. He'd once held a critical post at the Royal School of Ballet until a fall from grace left him with no option but to settle for work as a fitneess-instructor-sometimes-handy-man at an obscure school in the Yorkshire dales. But lower status hadn't made him bitter. He was a man of simple tastes and defined interests, and he found everything he desired at Fairyfield Grange. He appreciated the beauty of young men who dressed as girls, and his new place of work was full of them.

Hardwick had long ago developed a fatherly demeanour and fancied all his pupils adored him. He believed he had the kind of looks young lads found irresistible - dark seductive eyes, a strong sensuous face and lean body - and he flattered himself they shared with him the kind of relationship that imitated the erastes and eromenos of ancient Greece, one that was affectionate, trusting and pure. In London he'd always made a point of tucking them into bed and kissing their foreheads in the evenings. They were always so placid and content after a good milking, and once they'd had his dick up their backsides they couldn't get enough.

Overconfidence had been his downfall. The administration at the School of Ballet usually turned a blind eye to a bit of discreet man-on-man frolicking, but when he was discovered taking photographs of a class of male novices he'd dressed in tutu's, bad tempers had flared and he'd been told to go.

The ousting had been tough and had ended a way of life. Denied the use of his old haunts he'd had to roam far and wide in a quest for co-operative young men of the quality he was accustomed to, and it had often proved a frustrating business.

He found the regime at Fairyfield to be the answer to a prayer and a blessing to his pocket too. Miss Hancock laid great store in retaining youthful beauty by regular exercise. She wanted her students trained in girlish bodily expression and to appeal to the eye in every possible way, and she wished for them to be physically fit without appearing too muscular. Smooth slender limbs and a narrow torso was the ideal to strive for, she'd said, since apparent helplessness was part of a sissy's charm. He'd convinced her that an ex-dancemaster such as himself was exactly what was required. He was adept at all kinds of gym work, and nothing could equal ballet routines for maintaining suppleness of limbs and developing elegance and poise. And the dear things would have dancing lessons - not ballet, but country dance, some ballroom and a little jive - all most suitable activities for young ladies.

Everyone must think he had the best job in the world, but it wasn't always easy. Being a trainer of sissies sounded glamorous and there were some perks - so many of the gender-benders needed a regular visit from a cock - but it could be hard for a man alone.

Sometimes he thought he was the only one who did anything useful at that school. Teaching the babydolls how to please men was his responsibility. The women faddled around instructing in fashion, cosmetics and elocution, but it took more than that to produce a first-rate pussyboy. It took plenty of evening commitment, lots of cock, and galleons of cum. Yes, and it was vital to keep emptying them of all the spermy juices that made them manly.

He couldn't understand Miss Hancock's attitude. Despite being determined to make a profit from the pretty things in her trust she had so little imagination. Sissies needed men to fuck them regularly, and there were too many for him to manage alone. She could so easily combine that vital requirement with earning a sound additional income. In the past he had visited a number of 'meatracks' that discreetly provided sweet looking lads, and he knew some men would pay exorbitant fees to make use of the real good lookers. He knew the headmistress gave certain people access to the beauties at Fairyfield Grange, but unaccountably when he'd suggested opening the school to a wider clientele she'd told him she 'left the running of brothels to others'.

He moved closer to his young companion and eased him onto his side before drawing back the covers to study the pale bare buttocks. Reaching out he spread them with his hands to reveal the slightly pink whorl between. Clenched in sleep it displayed no trace of the pleasure it had given the previous evening. At last the mans drowsiness departed and became replaced by restless energy. He wet his fingers with spittle and gently rubbed the exposed anus in a circular caress. The she-boy stirred and moaned sleepily, and Hardwick felt a twinge of pleasure as his penis thickened. Almost casually he reached for the container of oil on his bedside table and drizzled a copious amount of the clear lubricant onto it. He preferred oil to patent jellies or creams, since it never cluttered him with residue.

As he massaged himself with his finely manicured fingers he admired himself. He was nicely endowed, and although he prided himself he'd never stooped to the vanity of measuring his erection he was confident it was nearer to eight inches than it was to seven. Just how a young sissy's tender rosebud could manage to accept such a monster amazed him, but just a few hours previously the one in his bed had taken it's length and girth admirably. He'd buggered him almost constantly for several hours and ejaculated into him copiously three times.

Caressing the tense anal bud once more, he transferred to it the surplus oil from his fingers, and at last the boy stirred and sleepily opened his eyes. "Just one last time, then we'll have to get ready for breakfast." Hardwick told him.

He moved forward to press the head of his tool between the slender buttocks and heard a sharp intake of breath as he pushed against the resistance of the lads sphincter. Pushing harder he felt a slight give in the ring, then slowly the tip of his cock breached the anal portal. The sissy stifled a cry as the widest part of his cock-head entered to enjoy some delightful peristalsis as waves of involuntary muscle contracted and pushed around it.

"Here we go then!" Hardwick murmured. He always maintained sissy- lads sparked better during the day if they started out freshly fucked and with a bum full of warm cum

***

Mornings were a rush in the dormitories, which was a distaste to Wendy who wasn't a natural early riser, and unlike the others he had to sit on the edge of his bed and take care putting on his stockings.

It had been a hot night and promised to be a hot day, and it would have been so much easier to just pull on a pair of socks. Hurrying too quickly could create a tear in the fine denier mesh and his aunt detested any hint of slovenly appearance in her pupils. She certainly wouldn't tolerate untidiness of any kind in one of her prefects.

Stretching each item of hose over his hand in turn he rolled them into weightless rings of nylon before reaching down to slide in his toes and smoothing each stocking up high on his thighs. Attaching the clips of his suspender-straps to the top of them at the front he then he stood up and reached behind to stretch each remaining suspender down across his buttocks until he could affix them to the dark welts at the back. Tights would have been easier to put on, but his aunt abhorred them, thinking them grotesquely unglamorous things for a girl to wear under her skirt, and she ridiculed self-supporting stockings as useless since they never self-supported efficiently.

With a rush of vanity he rubbed his knees together to hear the stockings rib together. Nylons may have been a nuisance early in the morning, but they did sheath a boys legs tight and give them a nice shape, and they were ideal for emphasising pretty ankles. Even on hot days they were preferable to the bare legs and little ankle socks endured by the first-termers.

Standing up he took a gymslip from its hanger and lifted it over his head, sliding it down until the shoulder straps settled comfortably over the blouse he'd put on earlier. Making a slight adjustment to the drape of his skirt he then tied the accompanying sash about his waist. The small curvature of his hips was immediately accentuated as the hem of the box-pleated skirt rode high on his thighs.

He stared at his reflection in a wall mirror, turning this way and that. With a little skirt swirling about his thighs he was pleased with what he saw - yes, he did have good legs, and the nylons gave them graceful, attractive lines. He smiled. He thought the dark blue smock and white blouse presented a bright fresh picture, and for an eighteen-year-old young man with a nice, round, inviting bottom he looked rather fetching in a schoolgirl uniform.

Picking up a two-pronged leather tawse he clipped it onto his waist sash. There were times he felt fed-up with life at Fairyfield Grange, but when he thought about it there had been little radical change in his routine since William became Wendy. He'd had no settled home for ages, so when his parents agreed for him to remain at Fairyfield instead of going to his grandmother in Brighton he wasn't particularly upset. Being dressed and treated as a girl had been a shock at first, but since he wasn't academically minded the unchallenging curriculum suited him well.

Being compelled to be a girl was a new experience, but he'd always been precocious in the way he moved, and at his previous school he'd carried himself so lightly the older boys would often wolf-whistle as he walked by. Not being robust he had learned to seek their association to avoid bullies; providing favours in exchange for their protection. He glanced at his wristwatch and suddenly Brighton faded into unreality; forgotten dreams that had never been real. Fairyfield Grange was reality now.

He hurried out onto the landing and walked along to the casement overlooking the kitchen yard to chase away the clutter of students who always congregated there when Larkin's van delivered groceries. At exactly seven-forty-five on alternate days Ned Larkin's van arrived in the yard below with Judd sitting in the passenger seat. Judd was a teenage hunk and everyone's flavour of the month, and the van was already there.