A Sissy Saga Ch. 20

"Must have escaped from a zoo." retorted another voice.

Pamela Upduff was stiff with concentration and her face felt like cement with the effort of trying not to pant. It was all so awful. A young man dressed-up like a girl, exposing his genitalia, blatantly displaying his gigantic - erm -youthfulness.

A horrible guilty pleasure engulfed her. The best kind of pleasure. It was ten-times more reprehensible than she could ever have imagined. She felt suffocated while the other women whistled and cackled like hens. Even Mrs Carter-Plackett, a charming and motherly woman in a flowered dress and neatly curled hair was cheering. They were enjoying every vicarious moment of the joyous erotic panorama.

The women around her panted audibly. She herself boggled in disbelief and didn't know whether to exult or scream. What were they all thinking of? In the daytime they were all so ultra-respectable, but apparently when the sunshine faded so did their morals.

"Oh," Mrs Fawcett grinned, "He's scrumptious. An absolute poppet."

"Drop-dead gorgeous." agreed Hyacinth Glossop, corpulence overflowing her chair and leaving only a streak of guilt wood to be seen here and there.

Pamela felt trapped in a cloud of heady floral scent as Poppy drifted in front of her. His presence seemed to penetrate beneath her public veneer and see into her mind. He introduced a paroxysm of guilt she had rarely known before that uncovered all her most wicked susceptibilities.

"Erm!" She faltered, tempted towards a compliment but lacking quite enough nerve. Her mother would be beside herself with horror if she knew about this. Oh how could it be happening? She went out of her way to be a good neighbour, she went to church three times every Sunday, felt sorry for all the little poor black children in Africa, and she made regular donations to a donkey sanctuary. Yet there she was, lusting unhealthily along with all the others.

With a small, sly smile on his mouth Poppy stood with his weight on one leg so that his pelvis tilted up at an enchanting angle, then reaching down slowly he took his gigantic prong in his pretty manicured hands and held it upright as he waltzed out of the room, regarding it with the reverence given to a dance partner, slicking back the foreskin to gaze at the bulbous knob-end as if he really was in love.

***

When the guests had gone Poppy found himself in another room. It was an impressive salon where the walls were covered with a copy of a fresco one of Mrs Boroclough's relatives had seen in a mausoleum at Halicarnassus. Naked and robust women and effeminate looking youths, miraculous in their levitation, sprinkling flowers on heavily armoured Greek warriors.

The room had a white and gold coffered ceiling and was snug, though it was more of a showpiece than a place to live in and the furniture was all draped with dust sheets. He was naked and Mrs Boroclough was scrutinising his delectable body and serpentine penis with an attentive expression. At fifty-five she was still a woman with regal baring and the aloof, unshakeable confidence that came from living a thoroughly privileged life.

"Lovely creature. Even more delicious than the last time I saw you. So beautiful, so feminine - in most respects - and so sweet."

The sissy was standing with his back to the wall, and beside him the woman's thin, big-boobed companion, Clementine, was observing him too. "Nice little breasts, Mrs Boroclough," she enjoined, "They belong on a girl really. And just look at those male parts, so out of scale with the rest of him."

Mrs Boroclough nodded. "Breasts, tiny but perfect, and the rest of him..." She glanced down at his groin. "Exceptional. Incongruous, but extremely arousing."

Uninvited, she pressed her lips to Poppy's warm cheek, enjoying the delicate undertone of his skin and its moist scent, a scent that seemed to indicate that a bunch of warm lilies were somewhere couched at the base of his neck. Gliding her lips along the curve of his neck she moved lower, kissing his breasts and drawing the nipples into her mouth, then flicking her tongue against them.

Her passion made Poppy gasp and he twisted as she suckled on him.

"I doubt if any man could pass you by without admiring you, sweet thing. Do you allow men to copulate with you often?"

Poppy blinked. He was not familiar with the term she used and didn't understanding at first. "Pardon."

Patiently the woman lowered her level of expression. "Do you allow men to shag you?"

"Um, sort of."

"A lot of men?"

"Quite a lot."

"In that case I won't cause you any undue discomfort if I imitate them." She unclipped her skirt to reveal she was wearing the biggest and best item Carmine Wilcox had to offer. Poppy's eyes grew large when he saw the bizarre phallic tool strapped to her pubis. The wicked shaft was rather odd looking. It was a semi-rigid plastic pole, flesh coloured with a bulbous tip, but it had a gentle upward curve and was deeply ribbed with tiny, pointy-warty nubbins along its entire dramatic length.

The woman stood, legs apart, hands on hips, her mouth presenting a slightly crooked smile as she basked in the pleasure of possessing such an impressive piece of male-like genitalia. She looked raunchy and wanton. Taking a grip on the uplifted shaft she stroked it in simulation of a man masturbating.

"Rather inspiring, isn't it. A lovely fat hot-dog to put between your slim little buns eh? I chose a nice big one for you Poppy. Can you imagine what it will feel like stuffed up your saucy bottom?"

Poppy paled as he observed the murderous dimensions of the thing swinging up from her thighs, but before he could say anything she turned him and lightly pushed him forward. His hands became pressed onto the top of a small lacquered table. Resigned to an unenviable fate he thrust out his bottom in submission and waited.

The woman contemplated his buttocks, marred only by a little recent smacking but still emitting the lines and texture that made them ever admirable. Small, soft rounds that would separate with the gentlest caress to surrender the enticing little pucker between. Men would pay handsome sums to know the inherent delights of that sweet young arse.

Such appreciation didn't mitigate her harshness. Ignoring the upturn of his buttocks she grabbed him by his hair. "You're too small, you little freak. I'd break my legs trying to get up you in that position, push your bum higher."

"Oh, Mrs Boroclough, oh..." Poppy's pulse raced wildly. Being pulled about and roughly handled had stirred some excitement in him and now his entire body trembled as he felt the nudge of the plastic device pressing onto his splayed bottom. Knowing what to expect helped. He dipped his belly and raised his bum.

Ensuring he was helpless she reached between his legs and pulled back his testicles. When certain he was settled and beyond rebelling she drew back and released his balls but remained watchful as she pressed a thumb between his buttocks and rubbed his anus.

Helpfully Clementine leaned across his back and spread his bottom, oiling all the right areas with the contents of a plastic squeezey bottle, and then holding his small buttocks open while Mrs Boroclough teased him with the tip of her apparatus, stroking the broad tip of her tool against the whorl of his anus.

Gripping the shaft of her strap-on in her fist she guided the broad tip onto a perfect target for cock. For girl-cock. She then took hold of his hips and braced herself.

Poppy braced too, his small bottom tightened as he moved it back and up to meet the awesome object. She positioned the bulbous helmet against the small, neat ring of Poppy's anus and shunted forward with her hips.

"Oooohhh!" He groaned and gripped the side of the table as he responded to the inexorable penetration, and "oooh!" His knees nearly caved in as he felt his hole stretch to accommodate the big plastic truncheon Mrs Boroclough was forcing in.

The woman's thighs tensed and her buttocks knotted impressively as she pushed forward, rubbing one hand along the outside of his smooth thigh while her other hand carefully wedged the tip of her strap-on appliance into its required location. Her face took on a determined expression and she clenched her teeth. Keeping her knees together she angled back, tightened her muscles and pushed with her lean, powerful hips. Glancing down as she squeezed the first inch into the lissom young backside, she began to press forward.

How satisfying to see her rugged girl-staff sink into the bull's-eye of a pretty arse, she thought. She sensed Poppy's anus was rather a snug little morsel usually, but since Clementine had basted both it and her tool with plenty of lubricant it proved no obstacle.

Poppy gulped as the intruding length of greased plastic lifted him onto his toes. "Push back and take it." the woman demanded.

Her cock sank in, and his pink anus flared significantly open as his tiny well-greased buttonhole expanded, thinning and dilating salaciously around the invading prong's blunt oily head. Once started it became easier. Further and further it went in until the she-boy groaned. Pain? Pleasure? Maybe a mixture. The woman didn't care.

Most of her instrument was soon sheathed, and a brisk jerk with her pelvis quickly forced in the rest. When fully installed she experimented by shaking Poppy's rounded derriere left and right and up and down, making him huff and puff as his bottom was pulled about and contorted into gratuitous shapes. His feet arched and his toes curled as the assault intensified and Mrs Boroclough began long-dicking him like a man.

"Wow, oh it's - it's - it's - oh fuck!" The sissy exhaled noisily as his smooth-rounded bum-cheeks bounced and jiggled around on the sliding shaft. He tried to relax, knowing it would be easier to co-operate, but the violent ramming of the full prick inside him forced him to concentrate.

"So you're a squeaker," the woman quipped heatedly, "Well squeak away, girly-fuck, because I'm going to give your precious boypussy a truly deep seeing-to. You're in for quite a lovely ride."

"Oowwwfff!" Poppy gurgled inanely and out loud, tilting his head back and lewdly clenching his anus around the large slippery knob in his backside. He felt the same searing brand inside that all boys feel when a man breaches them, and at that moment Mrs Boroclough was as good a man as any he'd ever known.

"Bounce on it," she demanded, "Bounce around on my cock... That's it... Good girl! Good cock-slave. You're my girl. You'll drop your pants and be my girl whenever I want you to be."

"Y-yes. Oh, yes..." He surrendered, utterly giving into her demented desire and rocking back and forth in tempo to the rhythmic thump of her latex tool. They were united, a big cock and a submissive bottom - boss and appellant - giver and taker. Now he was humping in lurid response to the girl's thick, slippery length and athletic thrusts.

The old woman seized him by the hair and cruelly hauled his head back. "That's it, move with me you little cow. I know you like it. I know you love it. Being fucked in the arse - it's all you're good for - you'd love a girl to give you a baby if she could. You'd love me to give you a baby, wouldn't you?"

The woman's hands gripping his hips tight as she began ramming him with the passion of a buck rabbit just out of celibate confinement and on high heat, sometimes almost lifting him from his feet with her enthusiastic thrusting. "Oh yes. That's it my sweet darling. Oh, you are a fine piece of fuck-mutton."

While this was happening, the redoubtable Clementine, acting as supernumerary to her former employer, was crouching down beside them and milking Poppy's cock industriously, aiming the juicing tip expectantly at a metal wastepaper bin tucked beneath the table.

The thrust of Mrs Boroclough's mature loins increased to fever pitch and each time she went in she drove harder and deeper.

Poppy panted heavily and the woman panted too. "You squeak and moan like a girl. You like to be fucked like a girl, but it's my turn to cum."

She gave a huge lunge that pushed her attached length fully inside, and ominously it seemed to swell. A squeeze on the fat juice laden balls between her legs instigated a glorious disgorging of liquid love along the embedded length.

"Oh, yes." The woman blurted as she pumped with frenzied spurting thrusts that stuffed the tender sissy to the limit, powering her replica seed into his welcoming warmth with a force that made his entire body jerk and jerk again.

"Aaaaarrrrh! Yes, yes. I can feel it filling me up." Poppy squealed as the woman's replica penis exploded like a volcano inside him and his stretched bum hole slithered on the fiercely rutting pole.

"Give out your honey, darling. Empty your handbag." urged Clementine as she frantically jiggled his swollen cock beneath the table.

Poppy mewled and thrashed his head from side to side as his body heaved and rocked. The woman was gripping him tight as he writhed, extending every muscle as a sixty-megaton orgasm took him, and trapped in the midst of delicious torment his cries were probably a reflex.

"Eeeetch! Mmm, yeah! Give me a baby Mrs Boroclough - Oooow yes, give me a baby."

A strangled whimper as his big sissy stick convulsed in Clementine's massaging hand and began to spew cum into the wastepaper bin. Quite suddenly his penis began to ejaculate sticky semen in fierce splatters, Clunk, plink, splot, splat!

Clemmy grinned in delight and continued pumping, her deeply tanned face radiating deep satisfaction as each viscous surge twanged against metal. Agreeably impressed at the amount spurting out of him she gazed up at her mentor. "Goodness, Mrs Boroclough. You've picked a fine specimen this time."

***

Poppy was returned to Fairyfield in the back of a taxi late that same evening, and both Jennifer and her mother met him at the door. Self-consciously the she-boy fished an envelope from his pocket and handed it to Miriam.

The headmistress perched a small pair of spectacles on her nose and studied the note it contained, and having read it she stopped Poppy in his tracks.

The slender she-boy turned and peered at her coquettishly, eyelashes fluttering, budding breasts pressing out the fabric of his dress. Then he came over and stood formally, hanging his head like a miscreant hauled up for some crime, his cheeks tinged with a slight flush of guilt.

Miriam found herself looking at an exquisite ring of gold and amethyst threaded onto one of his fingers. "Did Mrs Boroclough give you that?"

"Yes, miss."

She held the note aloft. "The lady seems smitten. She informs me she wishes to wed you, Poppy. Do you want to marry her?"

He wobbled his shoulders apprehensively. "Um, yes please, Miss Hancock. If I'm allowed."

"We'll decide about things in the morning when I've had a discussion with the lady concerned. You'd better hurry off now and get your beauty sleep."

When he'd gone Jennifer gazed at the note in her mother's hand with an expression of consternation. "A marriage? Mrs Boroclough wants to marry Poppy?"

"It's only right she should ask me. He is rather delicate, a rare flower that can be picked or stamped on, and I'm the nearest thing to a guardian he has at the moment."

All saw Poppy as beautiful, but for Miriam Hancock he represented a certain kind of perfection. The soft shimmer of his hair, the molten-tar smudges of his eyes and the subtle curve of his mouth projected a purity that discounted the bizarre escapades he often became involved in. He was a transvestite who was quietly sure that nothing he did was ever sinful or wrong, and he had the most honest face she had ever seen.

"Marry him? Jennifer repeated. She made it sound like an oath. She was astonished. "Marry? Surely not. It's ridiculous. Poppy could never be an husband to anyone."

Her mother smiled. "Of course. Everyone knows that. He's a full-time girl, so Mrs Boroclough will take him as a wife."