A Sissy Saga

Simon Blanquette went down the stairs quietly hoping to get out of the front door before his mother could confront him, but the woman was alert and had been half-expecting a sly escapade, and he didn't make it.

"Where are you going Simon?" she asked him in the hall.

Technically an adult he quivered like a child in front of her and offered a soft ingratiating smile. "I said I'd go and see Caroline this evening."

"Caroline!" the woman frothed, "You're going to see a GIRL?"

Simon squirmed slightly where he stood. He was blond with high, well-coloured cheekbones and the kind of dainty build that made him look cute. "I know she bullies me, but she is a sort of friend. And I am eighteen now so I should be allowed to see girls if I want too."

The woman's mouth curved down in a sulk, making the most of her pretence of being hurt. "But Simon this is not the right time to go visiting. Tonight is the last evening we will have together before you go to your next school and we may not see each other again for months. Don't you love your mummy enough to spend time with her?"

Her son gazed down at his shoes. She always demanded utter deference to her wishes and there was no escape. Despite being technically an adult his mother still dominated his life and constantly scolded him as if he were a child. Whenever she did that he could help feeling like a child. "I've given my word to Caroline." he responded meekly.

Brusquely the woman took hold of his sleeve and received no argument when she guided him into the sitting room and closed the door. The room was large and open-plan and generated an air of opulence. The air smelled of furniture polish, there were cream walls hung with abstract paintings, and modern rugs scattered on a shiny oak floor. Two red sofas dominated, flanked by black lacquered furniture, and a copy of 'Sussex Life' lay on a side table. "If you go out and leave me I won't be able to give you the lovely present I've bought for you."

Simon experienced a rather ominous sensation in the pit of his stomach. He couldn't help it. Every time she dragged him into the sitting room in that way his confidence ebbed, just as it used to as a child summoned before the headmistress. But it seemed he wasn't to be given all black marks that evening. "A present. You've got a present for me? What is it?"

With his blue eyes open wide Simon could be rated as alluring, and the woman's own eyes sparkled as she returned his sudden enthusiasm. "It's the sweetest little outfit ever. Such a snug bodice, and with a delicious flaring short skirt."

Simon felt his heart rise in his mouth and the funny turn in his stomach did a flip-flop as his mother opened the lid of the package she'd previously placed on one of the red sofas.

The young man blinked. "It - it looks like a school uniform. It looks like a girl's outfit."

"That's exactly what it is. I want you to wear it tomorrow, which means you'll have to play dress-up tonight."

Simon felt an odd sensation in his pants, just like he always did when she offered him a present such as this one. He took the dress from its packaging and held it up against himself, spreading out the hem so that the skirt flared. "I suppose I could call Caroline and tell her I've got toothache or something."

His mother nodded. It was important to make it absolutely clear that she was in charge and that he was expected to do just as she wished. Hers was a feudal ownership and her subjects had no right of appeal. "Do it upstairs. Take the clothes with you and put them on. I want to see how they fit."

Simon hesitated and blushed as was only proper at such a demand, but he quickly recovered and nursing a shy smile he draped the new clothing over his arm, turned, and made his way out to the stairs. When he had gone Mrs Blanquette sat down and thought things over, but was really quite sure in her mind that the plans she had made provided the best solution.

On attaining the age of twenty-one Simon was due to inherit a huge amount of money and complete control of his late father's estate, which at the moment she held in trust for him. Her most morbid fear was that he would one day develop a streak of independence and sideline her importance. The very fact that he had contemplated sneaking out to visit a girl that night was a dangerous sign and it had to be crushed. That was why she had enrolled him in that school. The woman there was adamant that following a year of tuition in her establishment he would be utterly emasculated and one hundred percent subservient to a mother's wishes.

The school was rather exclusive, and the criteria for acceptance was discriminatory. The height of a student had to be in the range 1.68m and 1.72m, and they had to be fair of face and as thin as a rake. Luckily Simon was five foot six and qualified easily in the other respects.

Feminising him shouldn't be a difficult job for someone with just a modicum of expertise, she thought. Simon was already a sissy in many ways; everyone knew it, even that Caroline girl. She was sure he only went to visit the strumpet because she allowed him to try on some of her clothes. Neither racing cars or aeroplanes had ever engaged her son's attention, in fact when walking out he liked nothing better than to linger at shop windows and moon over girls clothes, shoes, handbags, iridescent containers of eau-de-cologne, clear lavender water and luscious little bottles of 'Evening in Paris'.

When he reappeared Simon was dressed as she wished in a schoolgirl gymslip over a delicate white blouse. His mother's gaze, slightly mocking now, drifted over him with thoughtful appraisal and lingered like a caress. The bottom hem of the flaring little skirt covered the top two inches of his pale, slender thighs and little else, while beneath it she knew he would be wearing girlish panties and his lovely eighteen-year-old cockie would be fully erect inside them. A new frock always guaranteed to do the full trick for him.

"It seems to fit perfectly. Does it feel comfortable?"

She noticed the quickening of his breath and his reluctance to look her in the eye. He was slightly nervous, slightly excited. He stood by the door smiling coquettishly, the fingers of one hand covering his lips, his new outfit feeling surprisingly strange and light against his skin. "Yes -- yes, thank you." In his transformation his voice was light, immature, almost musical.

Mrs Blanquette beckoned him further into the room and had him stand in the centre of the floor. Simon was not heavily built and would probably always need someone strong to look after him. By good fortune she was rather strong herself. She stood up and moved towards him as she admired his waif-like beauty. He was willowy, doe-eyed and skittish, his golden hair combed into a line that fringed his brow. He may have been a bogus girl when he dressed-up, but he could be a convincing one.

"Yes, it really does the job, doesn't it? But you do look pretty," she said in a soft lilt. "You're beautiful, you're feminine, and you're sweet. You're going to please a lot of people when I allow you the freedom."

His arms remained limp at his sides, and of course she had known from the start he wouldn't resist. She moved closer, put her hands on his shoulders and felt the delicate bones beneath the tunic, saw the flinching pulse in his throat. Suddenly she gave a laugh that came from deep within her throat so it sounded like a chuckle, and a perfect flash of a smile drew him in. His fingers fumbled awkwardly with the folds of his skirt, but at least he remembered to close his mouth and return her smile, even though he felt mildly uncomfortable under her bold, almost menacing stare.

Her hands moved up and down his sides to assess the fit of the main garment, appreciating the shape of the body it contained. He didn't struggle even then, and as she raised his head to appreciate the soap-scrubbed freshness of his skin something passed between them - a look, a flinch of acquiescence. Placing a hand on his head she curled her fingers thorough his hair before taking a firm grip, then with her other hand she caressed his cheek, sliding a finger beneath his chin to tilt it up.

"Tomorrow we'll embellish things with a lacy garter belt. You'll wear sheer black nylons, not passion-killer panty-hose. You have beautiful smooth thighs and you do like to wear stockings, don't you?"

"Well I..."

"You do look good in them. Definitely dark stockings though. Black will make a gorgeous contrast with your creamy skin." She suddenly tutted. "Some of the buttons on the tunic will have to be moved over. Do you remember how to sew on buttons?"

When he silently nodded she began to unfasten things. "Let's get it off." she said reaching forward, pulling the gymslip from his shoulders and helping him to step out of it. "We have a long way to go tomorrow and we must start off early. You won't have time to sew buttons in the morning, you must do it now."

Simon frowned slightly. "I don't know if I want to go to another school, mummy. Not a residential place. I've never been away from home before."

"Don't be childish Simon; you'll make new friends as quick as winking, see if you don't."

He was wearing very little beneath the schoolgirl outfit, the skin of his body was very pale but with a pinkish hue to it. Gorgeous, the woman thought, he smelled like lavender only sweeter, like a sugar bun just out of the oven. Simon was an angel fallen to earth whose little pantied bottom would be a favourite with men for many years to come.

She continued to smile as his nipples peeped at her, pink and displaying hardly any aureole. She loved that. She loved everything about his girlishness. The tightness of his hips and the way his legs moved, and she loved to observe the shifting shapes in his cotton panties. While they stood together she reached down and smoothed her fingers over the contours of the delicate package inside.

"Oh, you are a naughty girl. That stiff stalk of yours will distract you all evening if nothing is done."

Simon blushed when he noticed the familiar shine in her eyes. His girlish willy-wonker was very stiff and pushing out the front of his pants, and he knew what was going to happen when she looked at him in that way. His eyes became bright with anticipation, and in a moment she was sliding the panties down over his legs and allowing everything to rear up.

"Sit with me on the sofa." Mrs Blanquette cajoled softly, while escorting him with an arm about his waist.

Apprehensively he settled next to her, and gauging the situation calmly his mother put her hand on his knee and caressed his leg and upper thigh before reaching in further. The warmth of his limbs were invigorating, his thighs seemed hot, his skin softer and finer than she'd anticipated. Her hand went in low, beneath the delicate, silky dip of his belly. She allowed herself a second to absorb the shape of his arousal which displayed a pleasingly nice size, then almost casually her fingers flexed around the flesh, and she hesitated. No need to hurry. No need to startle by being too brisk.

Simon gazed at her with big blue eyes, and his own hand moved over to nudge her fingers. "This is naughty." he said. Fortified by such seeming acquiescence she tucked her fingers under the firm flesh and closed her thumb around the top of it, marvelling as her touch defined the sturdy core beneath the pliable silk-like foreskin.

Slowly she wrinkled the skin north and south and noticed the length extend slightly and felt the girth expand a little more. His breath quickened to encourage her so she began stroking in earnest, rolling the soft skin up and down with steady rhythmic movements. Simon's head lolled back, his eyelids drooped and he responded with little gasps. "Uuugh, aah, aaah."

Oh yes, she thought, sissies the world over, she loved to hear them bleating their little squeals of ecstasy when she did this for them, when she was pumping them with passion. Ignoring her previous caution she picked up the pace, hauling down the sheaf of skin to expose the helmet glistening with moisture.

"There! Bet that feels nice, doesn't it? As good as anything that girl Caroline does for you, I'll wager."

The young man clenched his teeth and whinnied. "Mmm, aaah."

So quick and so soon, thought the woman. It was a disappointment in a way. She had expected things to go on for a minute or two before a conclusion, but Simon's excitement was plainly fiercer than she had judged. His breathing suddenly became laboured and he began tensing up almost immediately, his eyelids blinked rapidly and his face contorted. His erection was quite man-sized now and standing up like a gate-post.

Determined to play a full part in proceedings Mrs Blanquette gripped his gland firmly with the full encirclement of her fingers, then pumped up and down frantically. Within moments his thighs started jerking and shuddering, and then... "Ooh, oooow, aaah, OOOOOWWW, mummy, mummy!"

A heavy glop of translucent cream jumped out from the shiny tip, shooting an inch in the air and swirling crazily for a moment before dropping down to drape the woman's fingers. Then out came more making an even stronger exit, spitting twice the amount and leaping three times the distance before collapsing.

As a rivulet of warm semen flowed over the back of her hand Mrs Blanquette slowed down to squeeze the remaining ooze from the squidgy nozzle before finally relaxing her grip and meeting his dazed blue eyes, all smoky with wonder.

***

The following morning Mrs. Blanquette's car headed north beneath an overcast grey sky that gave no hint of the hot, dry summer that would soon descend upon the entire country. The breeze through the open window wasn't cold though, and birds sang a tuneful chorus in the hedgerows.

A year had passed since Miriam Hancock's mind had spawned the idea of a school, and now her latest recruit sat perched in the passenger seat at his mother's side. Simon Blanquette remained silent for much of the journey that morning, his mind preoccupied with his destination. His face was scrubbed to a shiny cleanliness and glowed with youthful vigour, as did his blue eyes set beneath thick lashes. His fair hair had been styled in a neat page cut, the fringe of which flew about lightly from time to time to highlight an aura of cuteness when caught by the wind.

The effect was a compliment to the navy-blue serge gymslip his mother had recently purchased in London, a style of smock that had once been the hallmark of a good girl's school, but which was now rapidly loosing favour in all but the most conservative of establishments. He was eighteen, but his new outfit, simple though it was, enhanced his arresting good looks, but equally important was the subtle change in his demeanour it introduced. It was a contrast to the puffy-sleeves and flaring skirts of the dresses he had worn so often in the past, and a reminder of the serious business that lay ahead.

"I wish you weren't going to America, mummy. And I wish I didn't have to go to a new school."

"Don't be silly, darling. Mummy needs to travel so she can make pots of money. The people at your new school will take good care of you whilst I'm away."

Simon had fretted about being taken on a journey dressed as a schoolgirl and was terrified that people would realise he was a boy in a frock, his unease being only partly pacified when his mother told him that all the young men at Fairyfield Grange wore skirts. That would need to be seen to be believed.

They paused at a wayside tea shop and he found himself alone, standing by the car awaiting his mothers return. There his concern almost whipped into hysteria when his brief little skirt billowed in the blustering Yorkshire breeze and a passing gang of roughneck youths wolf-whistled and called out; "That's it, tootsie. Show us yer knickers!"

They were just like so many others that teased him, but if they got him alone he knew they'd want to kiss him and feel his bottom with their horrible big hands. They alarmed him, but in a strange way pleased him too. They demonstrated how convincing he must appear in a dress and gave him some much needed confidence.

"Shall I go to America one day?" he suddenly asked on a long boring stretch of road.

His mother had then changed gear quite unnecessarily. She would have preferred to have used her humble Uno instead of the large unwieldy Bentley, but appearances were important to her that day. "That's unlikely dear. Why?"

"Daddy once said I'd probably like America. He said I'd like to see cowboys."

"Your dear father said lots of things he didn't mean, Simon. The only cowboys in Manhattan wear grey suits and creepy smiles. Let's just concentrate on your education for the moment."

That year the government was into its stride of creating motorways everywhere, but for much of their own journey they needed to make use of the long established Great North Road. Eventually even that was of no use and they were forced onto a narrow country byway that left behind the featureless flat fields and meandered up into forbidding hills. Within a short while the hedgerows disappeared to be replaced by gaunt, black, dry-stone walls.

At intervals they passed through sleepy grey villages full of stone-slated cottages with smoking chimneys lorded over by small old churches with square towers. Some of the shops in such places were curios, the legends inscribed on their front windows boasting of what lay behind. Black Fat, Weasand and Pig Bag; all varieties of tripe; indescribable food delicacies of the north.

The quaintness of such places was lost on Mrs Blanquette. She was a career woman of mature years earning a multiple figure salary and was more of a Mayfair lady than a country girl. If pressed to appreciate rural life she much preferred the South of France or Tuscany to the bleak outposts of northern England, and having gone through various lovers and husbands her facility to enjoy quaintness had long ago retired. She spent money lavishly, but never squandered her cash or time on the antiquated and unfashionable.

South of Skipton the Pennine Hills are composed of millstone grit, only good for growing coarse grass and oats and the short-haired sheep that can exist on such things. There, immense high fells stand poised at precarious leaning angles to cast great dark shadows over the moors, and in one or two of the broader isolated dales some of the 'new rich' of the industrial revolution had once built their homes. It was in one such valley, dun-coloured with dusky charcoals and earthy browns, that they eventually found the school.

"That's it. That's Fairyfield Grange." Simon's mother murmured as they topped a ridge. She slowed the car down and pointed along the dale, and together they gazed at a big grey house with high chimneys disgorged plumes of smoke.

Simon felt a knot grow in his stomach. "Looks like a loony-bin to me."

His mother was slightly alarmed too. At first sight it did appear to be an odd looking place. Like an idea from a drunken architect's cranky dream it didn't seem to gel as a single structure and could easily have served as a Dickensian institute for the insane. "Don't be silly," she chided, "One can't judge a book by its cover, or the quality of a house by its exterior." She glanced up at the scudding clouds. "It probably looks rather picturesque when the sun shines."

Following an uneven road along the dale they eventually approached a fence of tall iron railings surrounding private grounds. A title board by a set of great iron gates proclaimed: 'Fairyfield Grange, School of Charm for Young Ladies' and below that, 'Headmistress - M Hancock.' The gates lay open and a circular driveway led directly to the front of the main building, a house crouching like a monster amidst neat yet oddly incongruous gardens.