A Sissy Saga Ch. 21

Before anything could develop between them the pantyboy's attention was diverted by a woman tottering towards him, in one hand a glass of sherry, in the other a semi-opaque yellow drink containing a skewered cherry. She was youngish, mid-twenties, rather good looking with immaculately coiffered hair, and she looked exotic and friendly - if also rather tipsy. Sammy recognised her as a sort of celebrity newsreader from national television.

Joanna Toppingham had been discreetly observing Sammy since she'd arrived. The moment she'd entered the room her eyes had been drawn to the strikingly attractive poppet in female attire, and she thought him incredible. He carried himself so elegantly in his little black dress, just like a real girl, and the delicate threadlike straps on his bare shoulders tantalised for being all that supported the concealment of his adorable little chest and nipples.

Something had stirred in her immediately, and had eventually compelled her to appraise him from a nearer view.

"You're lovely," she murmured, inclining her head and offering him a merry smile. "I'm told that the girls here are really boys, but you all look so sweet it's hard to believe it's true. What's your name?"

Sammy suddenly felt tense. "Sam - Samantha, miss."

Chuckling at her own daring lasciviousness the woman sluiced down the sherry and handed the empty glass to Gloria who was standing nearby. "Is there somewhere this - erm, lovely creature and I could have a moment of privacy?"

Intimidated, the housekeeper became uneasy. She too had recognised the woman as Joanna somebody-or-other who was quite famous on television, and famous people tended to overawe her.

She flustered awkwardly. "There ain't nowhere 'cept Miss Hancock's study, but I don't think she'd want anyone in there."

Used to having her own way in all things and with an ego the size of the West Riding, Joanna poured the yellow drink down her throat and pulled a rye face. "Come, come woman. The headmistress is a charming person and I can't believe she'd refuse me a small favour. It would only be for a short time' and we'd just stand inside the door."

Her voice was slurred, but buoyant and insistent enough to make the housekeeper's resistance crumble, and Gloria hesitantly took a key from her pocket and led the way to the study door. "Just for a minute then, and I'll have to come with you."

Unconcerned by the ultimatum the guest swept blithely past her, dragging a bewildered Sammy by his arm. Once inside the room Gloria shut the door and stood with her back against it while Joanna leaned down to be at eye level with her chosen sissy.

"Show me, darling," she said, "Slip down your panties and prove to me you're really a boy."

Sammy inched up his little skirt coyly, but then found himself paralysed by her avid attention. "You're making me blush, miss."

"Ha!" The woman tweaked his pretty nose, "Silly creature. There's no need to be shy with me. I do lots of television work and I frequently visit dressing rooms when young men take their pants off. There! I shouldn't have said that, but you've such an open face I feel I can trust you."

Immediately she took control of things herself, pushing Sammy's hands aside and groping beneath his flimsy dress. "My, what pretty legs you have." she muttered as she hauled his pants down over his nylons. With a brisk flick of an immaculately manicured hand she raised the front of his skirt and gazed in delight at the male-genitals revealed. Smooth, well-formed and dangling with deceptive innocence.

"What a naughty surprise to find in a girls knickers, and such delicious pair of balls too, they look so cute in their little pink bag. Gosh, you are a honey. How old are you Samantha?"

"Eight-eighteen, miss."

"Eighteen! In that case I expect your willy will get stiff if you play with it. Will you play with it for me?"

The developing situation increased Gloria's interest and she left her place by the door to peer over the guests shoulder. "Go on. Do it fer the lady, Sammy luv. You've done it plenty of times before with people watchin'."

Usurped from her accustomed role of dealing directly with boys herself, the housekeepers thoughts wandered to other things as Sammy started to jink his foreskin to and fro.

The visitors derriere was thrusting back at her invitingly, in a nice, round, impudent kind of way, and it was undeniably attractive. Gloria was quite disposed to girl-on-girl stuff from time to time, but hadn't done anything with a woman for months. Miss Hancock always had something else to do lately, and none of the other females at the school would allow her to touch them intimately.

As the pert, poised rear-end of the guest seemed to be inviting some attention she chanced brushing her hand across its expanse, and on receiving no objection from the preoccupied Joanna-woman she became bold enough to slip the hand beneath her skirt and fondle the chubby bottom. Still no protest. Fortified by alcohol Joanna seemed to have put aside any pretence of scruples.

'Drunk as a skunk an' ripe for some jiggery-pokery', decided Gloria gleefully. She pushed two fingers forward to find the gusset of the woman's pants pulled tight between her thighs and drawn up so taut they accentuated the plumpness of her vulva delightfully. New found confidence quickly blossomed into impertinence as the housekeeper raked her fingers back and forth, stroking more firmly and digging deeper with each successive pass.

The television-person was entirely occupied observing Sammy's penis as he pumped with his hand, and appeared oblivious to Gloria's touch. Outwardly she remained impassive to the fondling between her legs, but strangely her very immobility gave the housekeeper encouragement to continue.

Gloria knew all about anatomy, so even though the woman was secured in her pants she had no trouble in worming a fingertip around the site of her clitoris before drawing it back to test the accessible nature of the hidden vagina and probe lewdly at the indentation of her anus. Eventually moisture began to filter through the gusset of Joanna's knickers, just a slight oily dampness at first, but soon becoming a copious ooze.

The woman started to gasp, and the more Gloria rubbed, the more she panted. Sammy didn't understand what all her noise was about, but her excitement infected him and his cock rose up like a stick.

"Oh, it is stiff!" Joanna exclaimed, trembling with enthusiasm. "It's come up wonderfully, and it as such an adorable well-formed knob-end. It looks firm, wet and gooey. It's ready to unload, I just know it is. Don't stop rubbing it Samantha. Keep wanking, you naughty girl."

"I-I don't know if I'm allowed to do a squirt, miss." Sammy answered faintly.

"Of course you are," Joanna gasped desperately, "No one will object to you pleasing me, and I want to see you shoot."

With a reddening face hot with flushes she snaked her head around to glare at Gloria. "Tell this creature it as permission. I want to see the tranny-tart toss-off."

"'Course you do," soothed Gloria as she strummed the woman's slushy pants, "Listen Sammy, you jus' carry on an' make a proper job of it. We's all here to please people today." As her fingers slithered around the puffy shapes inside the woman's pants it would have been difficult to dissuade herself from such duty at that moment.

"That's it." enthused Joanna as Sammy's fingers began to accelerate their movement. "Freaks like you need milking constantly. Not by me of course. You should have a pretty girl with soft hands doing it, or a man. Yes, you'd probably prefer a man, and given the chance they'd probably queue down the street to play with your doodle. They'd want to cum in you and on you and empty your pretty pink bag over and over again."

Sammy jiggled his cock furiously for several more moments, then he uttered a small choking moan as a streak of semen jerked from its tip and plummeted to the floor while another slavered over his fingers.

"Yes," the woman exclaimed, "I knew a queen like you would squirt beautifully. Keep wanking you tart, get it all out."

Almost as if to pacify the woman's inane urging Sammy's cock jacked out another big creamy dollop and Joanna's eyes bulged as she watched it roll over his fingers. At first she whimpered softly and sucked her lips at the sight, then quite abruptly her mouth became slack. "Oww, bloody 'ell! Ooooow, aaarh!"

She tore herself away from Gloria, clutching her groin, thighs scissoring one against the other, knees flexing, head bobbing up and down.

"Aaaarh, mmmm!" Lips drawn back and teeth fully bared, her expression was one of pain and anguish, but even Sammy knew it was rapture. Joanna Toppingham was experiencing a huge cum herself.

Eventually the gyrations ceased, and as shame soaked through the guest's alcohol addled brain she became irrational enough to jab an accusing finger at Gloria.

"I've been embarrassed! You've humiliated me, Mrs Fat and Ugly. I wouldn't have come into this room if you hadn't let me. How dare you tease me with emasculated young men and rub me with your grubby paws, you fucking old cow?"

Gloria looked at her quizzically for a moment. "Now then, there's no need to be rude." she said. Then her jaw clamped, her fist bunched into a solid lump and she biffed the famous television-person in the eye with force enough to send her reeling back.

"Yaaaarrrhhh!" howled Joanna as she bounced against the wall.

"Manners maketh the Miss, y'know," the housekeeper told her solemnly, "Bein' rude's a sign you didn't have a good nanny an' weren't brought up right."

Joanna hugged her face and sniffed. "What did yu wanna thump me for? I didn't know you were a nanny. I should have known only a nanny would know how to stroke my pants so nicely."

"Well, I ain't been a nanny for a while, but I ain't forgot how to be one."

The woman tried to compose herself and brushed a strand of straying hair from her face. "I feel sick and dizzy. I need a cigarette."

"Best go out into the front hall then madam," Gloria advised, "Miss Hancock don't like people smokin' in her office."

As the woman departed Gloria followed, pausing only to give the startled sissy-boy a stern glance. "'Ere Sammy, you make sure this place is left clean an' tidy afore you leave else I'll give you a smack if no one else does."

Left to himself Sammy looked about for his pants, then realised that the television-lady had absent-mindedly gone out of the room clutching them in her hand.

Outside in the hall the behaviour of the guests was becoming increasingly ribald, and deprived of the skimpily clad aerobics dancers and with their libido's lowered by alcohol their attention had turned to the waitress's.

Candy was standing at the end of the room held in conversation by a lady and gentleman seated on a couch who were both blatantly stroking up and down his nyloned thighs and reaching under his skirt, whilst Jemima was giggling coyly as a softly spoken man tried to induce him up the stairs to the second floor.

Surrounded by a group at the other end of the room Zoë was being encouraged to dance to the staccato beat of a dozen pairs of clapping hands, and it was only Jennifer's intervention that prevented him from being cajoled into performing a striptease.

In fact she made a point of disrupting all such instances, and smiling sweetly at the guests she made some excuse to drag each of the sissies away. Her mother had a program for the day and she was guarding it scrupulously in her name.

Sammy wiggled his way back into the room and stood demurely before the elderly man who'd been drooling over him previously. Stirred into mischief by the decadence he'd recently been party to he battered his pretty eyes until he was sure he had the gentleman's attention, then began to flip the hem of his little skirt up and down. If the old gent wanted a thrill he had no qualms about giving him one, and he knew it wouldn't be long before it was obvious he wasn't wearing any pants.

Jennifer pounced like a cat, grasped Sammy by an ear and dragging him off to another part of the room, leaving behind the grey-haired man looking annoyed and disappointed. A moment passed, then the man rose up from his seat and slouched off to seek a breath of fresh air.

Wendy had been sent out onto the porch to gather abandoned glasses, a mundane chore that didn't fit with his own sense of status. With a touch of pique he decided to string the job out as long as possible rather than chance being detailed for a second just as distasteful, but he'd being working for no more than a minute when he was joined by an athletic looking, smartly suited man in his fifties wiping his florid face with a handkerchief.

"Too hot for indoors." the man remarked absently.

Wendy lowered his eyelids and smiled back at him sweetly. "Yes, but the weather's lovely outside."

There was moment of appraisal as they studied each other. For his part the man found immediate pleasure in the young, well groomed person before him. The smile and the engaging musical lilt of a voice yet to break fascinated him. He'd just spent forty-five minutes ogling a striking girly-thing inside the hall whilst drumming up the courage to make an approach, only to see him snatched away, first by that ghastly television newsperson Joanna What's-Her-Name, and then by the headmistress's officious daughter.

It seemed apt compensation that the lovely sissy-thing near him now was as equally as pleasing as the last. He was younger than he'd first thought, deliciously young, and even more available. His face was sensitive, yet there was a flame in his eyes, and he liked the set of the head on his trim shoulders.

"I - er - I still find it difficult to believe that you and the other young men here aren't really girls." he stuttered awkwardly. "You all look so - erm - adorable in your pretty frocks, and you act your parts to perfection."

He took a brave step forward and his eyes tracked over the young queens sunny face. "What I mean is, I'm - er - not used to it, you see. I'm a stock-broker. I deal with vast amounts of money and I'm usually very sensible. But I've never - erm - never indulged - you know - with a young man, much less one acting the part of a girl."

Wendy feigned surprise and raised two melting eyes. "Not even kissed one?"

"No. I've never even kissed one. Not on the mouth, as it were. I mean that's not acceptable is it?"

Wendy's eyelashes swept up and down. He was always mindful of the clumsiness of men new to using boys, but at least this one looked kind and thoughtful and admitted his failings. Perhaps all he needed was a little guidance.

"Depends who you want to please, sir. Some boys are made for kissing. They love it, and I think you'd love it too if you tried it." He moved forward to reveal his utter loveliness, and the gentleman felt bewilderment he'd never known before.

Hesitantly, timidly, the strangers arm closed around Wendy's shoulders, and on finding the young man made no attempt to slip away he drew him close.

"Gorgeous!" he breathed, reeling from the rise of delicate perfume. "Acting like girls all the time. You she-boys - you young people probably - er - Do you - er - boys kiss each other and stick your tongues into each others mouths?"

With his lips slightly parted and his eyes as big as he could make them Wendy gazed up at his face. This was more fun than collecting dirty glasses. "There's not much we haven't tried. I like boys a lot, but I love men." he answered.

Everything seemed so natural. Without asking permission the banker gathered Wendy against his chest, pulling him close until the sissy felt the rasp of his jacket on his cheeks, the soft silk tie on his nose, and smelt the scent and soap of man.

The man's lips stirred the crown of his hair. He couldn't control his feelings, couldn't hold them in. "What's your name?"

"Wendy, sir." Wendy said.

"Wendy!" He repeated the name, making it come out of a strangled whisper of near panic.

Wendy sank back and tipped up his face, and drawn to the flutter of movement the man caught his chin in his palm.

The next moment he had the young thing in his arms and his lips trembled as he covered the she-boys mouth with his own, firmly clamping onto the soft, pink lips, crushing them and munching hungrily.

It was the kind of fierce melding of hot lips and flickering wet tongues in which Wendy excelled and he gave the amorous gentleman the benefit of his experience, raising up on tiptoe, throwing his arms about his neck and rolling his mouth around quite shamelessly, even opening it wide to invite the man to lick down into his throat.

The stranger was too coy to do such a thing, but he gloried in the warmth of their illicit embrace, in the stir of Wendy's arms and the sensation of his youthful body palpitating against him like a captured bird. When they drew apart he was breathless and he suffered a moment of panic on discovering his hand was intruding down over Wendy's belly. "Oh - I - er -"

"It's okay sir. I like what you're doing." Wendy husked. Ever the manipulator he slipped his own hands inside the man's jacket, pressing himself close enough to detect something big and hard sticking up inside his trousers. Something that was sure to be seven or eight inches of solid meat.

"You're excited, sir. And you're so handsome and manly you've made me excited too."

He gazed up at the man's face, his expression one of deceptive innocent. "But if you want to get my pants off we'll need to find somewhere a bit more private."

Praise is an aphrodisiac, and the scent and the feel of the slender, effeminate beauty in his arms was all the man needed to sharpen his eagerness.

But it was not to be. At that moment Jennifer arrived snapping irritably about uncollected glassware, and the anonymous gentleman blushed madly and swung away in pretence of inspecting an urn of flowers.