tagNovels and NovellasA Sissy Saga Ch. 11

A Sissy Saga Ch. 11


"Your financial accounting is abysmal, Miss Hancock." said the man from the Department of Inland Revenue. "Some of the necessary records are incomplete and others are totally missing. How can you hope to complete a Tax Return for your business without appropriate qualifying evidence?"

Miriam Hancock eyed him with some malevolence as he poked the documents in front of him with a bony finger. Horace Weevil was a tall, thin man, who despite the long spell of fine weather was wearing an expensive looking coat with a heavy fur collar, over which peeped dark shifty eyes and a small, thin moustache. She thought he looked like a minor gangster.

Since they were alone in her parlour-office she didn't hold back from seeming a little helpless. "My business is just getting on its feet. Both I and my secretary have practically no experience with business-tax, and obviously the accountants I employ have proved quite useless at correcting our innocent errors."

"Innocent?" The man's smile was almost a sneer. After qualifying as a chartered accountant he'd spent fifteen years with the Inland Revenue, most of it on Special Investigation teams looking into tax-abuse scams. This particular case was a doddle. The woman had tried cheating her returns in a blatant, amateur way. "You've made dodgy declarations all over the place, Miss Hancock, and that looks more like a deliberate attempt to defraud the Inland Revenue of it's legitimate tithe than an act of innocence."

"The errors were never intentional, and I'm prepared to do whatever it takes to correct them, Mr Weevil."

The visitor grimaced and tugged at a badly knotted tie that had the colour of gravy. Long fingers complimented his lean features which were not improved by greasy brown hair parted on the left and scooped behind his ears.

After a further glance at the papers in front of him he placed his elbows on the desk, pressed his fingertips together and inclined his head. "My job is not to make personal visits to assist people - but on this occasion we could perhaps come to an arrangement, Miss Hancock."

"An arrangement, what do you mean?"

He leaned forward slightly, drawing her in towards him as if about to let her into a great secret. "You run a unique institution - lots of beguiling young men wearing skirts. Well - um - I could repair the damage you have committed to paper and vouch for everything as acceptable, but such a favour would require a favour in return."

Miriam was in no way obtuse about his requirements, nor was she inexperienced in making such deals. She said she would need a few minutes to deploy some people and if he wished to smoke while he waited would he do that outside her office.

Horace went into the main hall, took a cigar from his pocket, pondered about it, then put it away again. There was no one in the hall at that moment to look at, but he'd heard about this place from that perv' Arkwright who lived in the village. Arkwright had said the place was teeming with effeminate homosexual talent, and he'd recently had a fine old romp with one of the residents.

They were probably all the same here, Horace thought. All gagging for it. Gagging for a tall, lean, horny guy like himself to give them a good sordid memory. He'd never been with a man before, much less with one who wore a frock, but why disqualify himself from trying it? Horace Weevil and his sensibilities could be accused of many things but lack of direction wasn't one of them. When opportunity offered, he took it, especially if it was connected with something he'd always been curious about.

After a moment he took a leisurely stroll down a passage that led to the kitchen, bidding his time and in no great hurry now. Trying out his randy dick in an effeminate lady-lad was one of his fantasies, and there was plenty of scope for any amount of that kind of sexual deviance here.

He looked through an open door. The kitchen was fitted with an ancient black gas stove and was furnished with heavy, dark wood pieces. But it wasn't gloomy; it glowed bright with multi-coloured fabrics. Red and blue crocheted covers lay over the chairs and summery yellow and green check curtains framed the window and screened the doorless recess that was used as a pantry.

The stove was spotless with its brass rail and knobs shining like burnished gold, and standing in front of it on a piece of seagrass matting was Poppy. He was alone, a delicate and lithe five foot six youthful male dressed up girly. Over the top of his skimpy dress he was wearing a long, plastic blue bib-apron emblazoned with a huge white teddy bear and the words I'M CUDDLY, while his hands were swathed in a pair of oversized pink rubber gloves.

Horace hung back a bit. He'd never propositioned a man before, but this one was a real good-looker. Sweet, nice legs, long and sexy. After taking a peep behind to make sure no one was following his hand rubbed the front of his trousers, stroking his penis for luck. "Hullo, who are you." he enquired.

"I'm Poppy." replied the effeminate, "I'm doing kitchen duty and helping the cook to make dinner. It's just porridge with toast and jam in the mornings and bread and cheese for lunch. Dinner is the only cooked meal we have here." His eyes dipped. "I do washing pots and cleaning mostly, but sometimes I'm allowed to peel potatoes."

"I see. Is that part of the training you do here?"

"I've finished my training and I'm doing this while I wait for a placement. Miss Hancock says I might go to live with a sultan."

Horace smirked. "And what's on the menu today?"

"We have minced beef in the larder, so we can do meat and potatoes, or meat with spaghetti, or we can have pie or burgers." As he spoke a single bloated rubber-clad finger flicked from side to side in front of him in the graceful, precise movements of a windscreen-wiper on an automobile. "Minced beef is very versatile. We can do lots of things with it."

Horace moved across the kitchen towards him. "You're obviously very talented."

Poppy's mouth curved into a poor-little-me smile while his sparkling eyes teased from beneath fluttering lashes. "Most people think I'm stupid. But I'm not."

"Course you ain't. Bet you've got all sorts of talents. I expect you've got a good talent for pleasing men. Have you been with many men?"

The she-boy looked at him suspiciously. "A few."

"A few? I think you're being modest. I reckon you to be a little honey when you're in the mood. Are you in the mood now?"

Poppy had no misconceptions about himself. He was a fully fledged pansy-faggot and a push-over for a kindly, soft-spoken gentleman who wooed and courted him with nice words. He'd let a nice man shove a cock up his bum in a jiffy, but he didn't like to be taken by storm. He didn't like the stranger's creepy-crawly looks or his creepy-crawly attitude. He smelt strongly of violets, which was sort of nice, but he sensed he wasn't intent on being nice. He took a pace back and raised on an air of condescension. "No, I'm not in the mood at the moment."

Horace grabbed his arm and pulled him close. Putting a hand under the apron he squeezed a small breast through the thin fabric of the dress beneath. "Come on, loosen up mi' little filly. I ain't exactly repulsive, am I?"

Poppy winced and his heels went click-clack as he stepped from the matting onto the flagstoned floor. "No, you're not very repulsive. You're just... you know... unpleasant. Just sort of a little bit repulsive."

The man glared. "Ha! You're a cheeky minx, you are. I'll forgive you, but you'll do what I want or else I'll have you an' Miss Hancock both out on the street. She owes me a favour, y'see, and you're it."

Poppy repressed a shudder as the man leaned forward and belched stale cigar-breath into his face. He could tell by the gleam in his eyes he was going to take whatever he wanted.

"No need to be coy wi'me." Horace leered as his other hand yanked up Poppy's skirt, "A chap as needs. You don't mind, do you? You're a breathtaking piece of meat that's probably had more pricks than a pincushion already. We need to get better acquainted. No need to tell anyone. Mum's the word, eh?" he pulled at the hem of the dress. "We'll have this rag off for a start."

Spindly-legged spiders seemed to suddenly crawl over Poppy's skin and his face went porcelain-pale. "Oh -- um -- er -- I'm not free. Y-you have to pay me first."

Horace paused. "Pay you? Are you on the game?" His voice registered confusion and disappointment. The bitch-boy wore frocks and was as queer as a lead shilling, but he hadn't countered on him being a professional dick-pleaser.

Poppy looked him in the eye. "I may be a tranny but I still like to spend money." He held out his hand. "Ten pounds, please."

The man's jaw dropped. "Ten quid?"

"Yes. The men down at the clinic pay me that. They give me fifteen if I let them shaft me bareback."

"Clinic? What clinic?"

"The VD clinic in Peasmarsh. It's the only clinic I know around here."

The reply caused a rather stranded expression to appear on Horace Weevil's face, as if he didn't know quite how to take it. His complexion became the colour of chewing gum and he opened his mouth, then closed it again, cancelling anything he could have said.

Hurriedly he retreated into the passage outside the kitchen to vent a string of colourful oaths. VD clinic? The pervert was lying, wasn't he? Yes, of course he was lying -- wasn't he? It didn't matter if he was lying or not, the faggots reluctance and his reference to clap-clinics and knob-rot had killed all the amour he had for that particular Missy. He felt slightly cheated and reached in his pocket for the cigar that may offer some consolation.

"There you are, Mr Weevil. I wish you wouldn't wander around, I've had to search for you."

The woman who confronted him was slightly boss-eyed and built like a large onion. "Oh, and you are...?"

"I's Gloria, Miss Hancock's housekeeper. Miss Hancock as put someone in the staff common-room for you. Come wi' me and I'll show you where it is."


Disconsolate, Wendy seated himself on a lumpy horsehair sofa in the staff common-room. It had been ages since he'd been punished like this, being a prefect had secured him from such things, but now punishment had returned, and it was his passion for Judd that had been his undoing. He'd always dreaded his clandestine meeting with the village youth in the east wing would come to his aunts notice, because she had an uncanny knack of learning about everything that happened at Fairyfield Grange.

He had dark suspicions about Abigail. He was sure Abigail hadn't been asleep when he'd paused to put on some lipstick before leaving the dormitory that night. Perhaps the lipstick he'd put on, or perhaps the look of eagerness on his face had alerted Abigail to what he was doing, and he couldn't get the idea out of his head that his previous great love had betrayed him.

He had entertained an Outsider, so that morning his status as a prefect had been revoked and he'd been soundly strapped. His aunt had spared him the ignominy of being stripped and bound and thrust into the dungeon only if he agreed to entertain a visiting guest in the common-room - a guest who would want to play a 'game' with him. A sex game. A bottle of baby-oil standing on a side table explained just about everything.

He glanced towards the door as the sound of shuffling shoes approached beyond it, and he felt nervous. It was hard to say want kind of nervous, but it was mostly to do with meeting a strange man for the first time and being required to have sex with him immediately. It would have been prostitution if he'd been paid to do it, but he was expected to perform free and gratis.

The figure that entered the room was no gorgeous Prince Charming, it was that of a scrawny man with a pencil-line moustache, and he had prominent cheekbones that made his face look hollow and cadaverous. His jaw was pointy too, and his eyes were narrow squints. It wasn't a man, it was a rat, thought Wendy.

Face twitching, the visitor closed the door and stood directly in front of it, legs astride, hands clasped behind his back whilst studying the pseudo-schoolgirl with a morose expression. "So, you're Wendy."

Wendy felt a flush on his cheeks as he rose to greet him. "Yes sir."

The rat-faced man's eyes continued to look at him a while longer. There was a kind of reined-in excitement about him, and even though he noted Wendy's indecently short schoolgirl skirt he didn't mention it, he just ran the tip of his tongue across his lips and stood there for what seemed ages. The common-room was a kind of ancient parlour, all Victorian folderol's and a preponderance of overstuffed furniture, and perhaps he was checking that no one else was hiding in the corners.

Wendy hoped he wasn't blushing even though he knew he was. Then he suddenly got the idea that the visitor was blushing too. The man looked awkward and embarrassed, and he was probably hesitating because he'd never had sex with a man before. Eventually the stranger took a large red spotted kerchief from his pocket and wiped his face. "You're a pretty - er - girl." he murmured at last.

Wendy did what seemed appropriate and squirmed sweetly at the flattery. "Thank you, sir."

"Yes, very pretty, but also very naughty." the man said.

Blue eyes stared back at him in all innocence. "I don't know what you mean, sir."

The visitor had decided it would be rather appropriate and good fun to put on the air of a schoolmaster with someone wearing a gymslip. He moved closer. "I've received disconcerting reports about you," he declared, trying to inject some solemnity into his voice - trying to invoke a stern tone of authority but not quite succeeding. "I've been told you're a naughty boy Wendy, one that dresses up as a pouting schoolgirl to tease men. That's clearly true isn't it? And wicked girly-boys who do that kind of disgusting thing have to be punished. Oh, yes, they have to have their naughty bottoms smacked, and it as to be done on their bare. They have to take their knickers off."

Wendy wiggled his bottom nervously, imagining his pants felt somewhat tighter as he anticipated what was about to happen. Spankings hurt, but like many sissies he found them curiously erotic. Still, the way the man looked at him made him feel a twinge of unease. It occurred to him the visitor was even more nervous than he was himself and was likely to give him a real good tanning to fortify his excitement. He didn't like nervous men, they were unpredictable and sort of creepy.

Nevertheless he would be expected to put on a good show, so he huddled his bum-cheeks in his hands. "Oh sir, I-I don't think - I mean - oh please sir..."

"Please! Please what?"

"Please don't make me take my pants off, sir."

"And why not pray? Dirty little madams like you deserve whatever they get. Now get them down, d'you hear?"

"But sir..."

"This instant Wendy - I shan't tell you again."

Wendy knew he'd pushed his luck as far as was wise. Rat-face was warming up to the school teacher play-role and any more arguments could get him more than a spanking from the man's hand - he could get the strap, or even the cane, he just knew it.

Fumbling beneath his skirt he nudged his pants from his hips and pushed them down his thighs. The stranger held his gymslip up at the back and flicked his hand up under the plumpness of his bum as his smooth round cheeks spilled out over the elastic, then as he hopped on one foot to step out from his underwear the garment became snagged in the buckle of his shoe - "Oh, ouch!" - and he teetered unsteadily on his toes as the man took the opportunity to fondle him.

Now the man had his hands on his bare backside he seemed reluctant to relinquish it. "I reckon I'll sit down and have you over my knee - that's the best way to smack a naughty girl, ain't it? Knickers off and over the knee."

With no more ado he settled on the sofa, his strong fingers grabbing at the she-boys tightened bottom as he pulled him down across his lap. Wendy could feel his belly rubbing against the man's thigh, rubbing against something else too. But if his body lay docile his mind was racing, and he was unable to stop thinking about what was to come. His skirt had been scooped up his back and offered no protection, and his penis, which dangled between the man's knees, had started to thicken as a large exploratory hand caressed the smooth contours of his backside.

"Now then my naughty panty-boy, just let me have your hand -" His right hand was hauled behind his back - "and now let me rearrange you -" Instead of holding in place with a firm hand on his back like most people, the man reached underneath and took a full handed grip on his penis, blatantly wrinkling back the foreskin as he did so.

(Rub, rub) "Sir!"

"Yes, I know my dear, I know," replied the rat-faced man's sympathetic voice, "It's not quite what you expected and must be rather a shock..." A broad hand patted his bum-cheeks "...but never mind, you'll soon get used to the idea."

(Rub, rub) The hand jinked his flesh again, while the other became raised in the air before being swung down with relish. Splatt! On a helpless bottom.

"Ooow, sir!" The first solid spank took Wendy unawares. His bottom quivered with its impact and a hot smarting sensation spread fiercely over his punished flesh. He reared up and tried to kick his legs, but found himself firmly anchored in place by the hand gripping his penis.

Smack! On the left buttock, making the flesh judder anew. "Ugh!"

(Rub, rub) "Keep still, naughty girl!" the man scolded, stroking the smarting buttocks, feeling the heat, feeling the lovely crease that separated them.

Whack, splatt! "Oooh, Christ! Oww, sir..."

Rat-face spanked him soundly, alternating the strikes between each lovely reddened cheek and making them both shake, making Wendy's whole body bounce frantically on his lap. As he got into his stride the sound of the hand impacting on bare skin rolled around the room like the slow applause of invisible admirers congratulating him on his efforts.

Wendy could do no more than squeal softly, pain and shock mixing with heady excitement as each blow now came accompanied by a jerk on his penis Each time the contact clapped an octave higher, and so did the resulting cry of confusion. He felt like he almost wants the next slap because it would bring another squeeze on his cock.

Whack! On his right bottom-cheek to intensify its smarting. "Aaaah!" His small buttocks clenched and bobbed from side to side as he tried to make them even smaller and less of a target, but their wholesome rosy glow appeared to be a magnet to the man's hand.

(Rub, rub) His swollen penis was beginning to throb and the man's soft, sweaty hand was rubbing up and down the shaft. Up and down, slow strokes alternating with rapid jiggling. "Does my smacking hurt? It's no more than you deserve if it does."

He tried to wriggle sideways, but whenever he did that the man's hand paused in the shunting of his foreskin and tightened around his penis to haul him back into place. Incredibly, despite the discomfort of such rough handling he felt aroused.

Splatt! "Disgraceful girl!" Crack! "Dirty teasing panty-boy - got a hard-on now eh!"

"Ooooow, eeeeh!"

Wallop! "...I'll make you sorry -" Smack, smack! - "Disgusting fairy princess!" - smackerty-smack!

Then, suddenly he's not hitting anymore, but a hand is still rubbing his penis. Rat-face had made it so stiff and sensitive it was all that he could do to keep from pushing down into his hand. His bum-cheeks were clenching and unclenching all by themselves, and he was pushing his hips up and down - he just couldn't help it - there was such erotic pressure down there, in his cock and behind his balls. Suddenly the unseen hand was jerking him furiously, milking him like a cow.

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