A Sissy Saga Ch. 08

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Snurge
Snurge
133 Followers

"No sign of Abigail yet." observed one of those watching breathlessly. He noticed that some of them were flagrantly reaching under their skirts and rubbing themselves as they contemplated the young man in the van.

"Stop that at once. Adjust you clothes and go to your rooms." Wendy ordered. He'd been appointed a prefect in recognition of being a founder pupil, and probably because his aunt was the headmistress, but he'd never got on with being a figure of authority and left the punishment of students to others whenever he could. It was a flaw the first-termers sometimes took advantage of, and they'd often tested him to the limit.

The voyeurs avidly watching Judd sluggishly obeyed his dress instruction, but hardly stirred away from the window. Isolated from the outside world and living in circumstances that conditioned them to be girls they had acquired a girlish enthusiasm for idolising anything that wore trousers. In particular they shared an infatuation for the muscular youth old Larkin brought with him to offload the groceries. They could predict his routine to perfection. While the old man went into the kitchen for a cup of tea Judd always remained in the van until Abigail came along to provide a brew more to his liking. When the head-girl arrived, all flirting and fluttering, they would go off together to the old scullery at the end of the yard - just to have tea, Abigail said.

Wendy felt a good deal of bitterness toward Abigail. His cousin had become aloof when his mother had nominated him as head-girl at the start of term. Praise and admiration had gone to his head and his appointment had given him arrogance that was quite unpleasant. He was rude with almost everyone and he'd left his oldest, most trusted friends behind. Wendy had been left behind, ignored and forgotten, the relationship they'd once shared now in tatters.

In charitable moment Wendy sought comfort in halcyon memories. There had been pleasant times in the past, times of thrills during a summer when Abigail and he had sauntered around the gardens in a wonderfully mannequin-like way, carrying parasols and wearing sun-hats with enormous brims while swinging their hips beneath tiny summer frocks. At Christmas there had been kisses under the mistletoe and promises to stay true forever, and while he never expected himself to be Abigail's only lover he had hoped he would remain his most permanent one. He wasn't a man any more, he was a sissy and he needed to be fucked. And oh, yes, sex with Abigail had been sublime and as thrilling as he could wish for; fierce and tender, outrageous at times, but always adventurous.

That was all dust now. Abigail now never sought his company for anything.

He looked at the other boys around him at that moment with searching curiosity. They were all screeching pantywaists like himself and he'd shared sexual intimacy with all of them at some time, but they never fully compensated for the loss of his truelove.

"Judd's such a scrumptious hunk," murmured Jemima, "I'd drop my pants for him any time."

Having recently been inside Jemima's pants himself Wendy knew he wasn't being altogether frivolous. He was an eager little queer who'd shamelessly impale his backside on any cock that came near him.

"Bet he's got a dick like a hockey-stick when it's up." said Holly wriggling girlishly nearby.

Jemima grinned. "Wow, a hockey-stick! That'd make anyone's eyes water." And he contemplated the idea with spread hands caressing the rounds of his bottom.

The other sissies chuckled, and Wendy didn't doubt their sissy cocks were quivering inside their panties. He stared down at the van. He guarded an admiration for Judd himself that he'd not expressed to anyone else, and he wasn't about to share it with this bunch of tittering trouser-watchers.

"Go back to your rooms and wait for the lesson bell. Move now or I'll line the lot of you up and strap your hands right here." This time he added thunder to his voice and the others reluctantly began to back away.

At that moment Daisy came bounding along the corridor in a lather of urgency. "Abigail's fallen down the stairs." he wailed.

"His he badly hurt?" asked Wendy.

Daisy flapped his hands and gazed at him with wide anxious eyes. "I dunno, I didn't find out. Look, I'm just a first-termer, I need someone to tell me what to do."

Wendy gave him a furious glance. "Go and find matron or tell one of the tutors, you twerp. I'll go and have a look at Abigail."

He went along the corridor with the group of curious first-termers dogging his heels and found Abigail sitting halfway down the back steps nursing an ankle.

"You've got everyone worried. Are you okay?" Wendy asked in genuine concern.

"No, I'm fucking not okay," fumed the head-girl, "I slipped and twisted something, and it fuckin'-well hurts."

A single astute observation told Wendy the reason. Instead of wearing sensible court shoes with block heels with his nylons he'd found from somewhere a pair of chic black things with tall, narrow spindles at the back. No doubt he'd been intent on impressing Judd with them and had hurried too quickly on the steps.

"Can you get up? Can you stand on one foot?" he asked.

"No, I bloody can't. I told you I'm hurting."

A bittersweet smile played around Wendy's mouth and there was a gleam of malicious satisfaction in his eyes. Judd would be sitting outside in the van wondering why Abigail hadn't shown up. Maybe he'd go to the old scullery in search of him. That being a possibility he could think of better things to do than be nursemaid to Abigail when he was in such a crabby mood.

He gazed at the group who had followed in hopes of seeing blood and broken bones. "There's nothing I can do. You lot stay here with Abigail until one of the ladies arrive." he told them as he pushed beyond Abigail and went down the stairs.

Generally pupils weren't allowed below the second floor until midmorning, but he used his privilege as a prefect to scurry down to the door that led out into the cobbled yard. The coach-house was now the gym and the old stables were now garages or workshops. The scullery was beyond them behind an ancient wooden door set in lichen covered walls of York stone. Larkin's van with Judd still seated inside stood in the yard, and rather than let Judd or anyone else see where he was bound he didn't go outside. Instead he took a route by way of a warren of flagstoned storerooms and entered the scullery through the back of a disused pantry.

The place was empty, only used as a kind of tea room by the gardeners who were already busy with their chores. It was dingy inside, only the morning sunlight lit the room to cast shadows across the white plaster walls and the ancient girandles that in earlier times had supported candles and rushlights.

He found a clean mug and a kettle plugged into a solitary wall socket and stood shaking. He was being wicked, but would Judd come and make it all worthwhile?

He'd just made the tea when he turned and saw the figure of the youth standing in the doorway - tall and slim with dark hair, long and thick in texture. Coming forward Judd ran his fingers through the tumbling locks and flicked them away from his eyes.

"Ahr, well now, I was expectin' to find Abigail here, but here's a nice enough soul who'd not deprive a workin' lad a brew." He wiped his face with his sleeve and pushed the door shut behind him.

"Abigail's had a small accident, so - so I've come instead." Wendy explained, feeling his legs tremble as he placed the steaming mug down on a dust encrusted table. He regarded Judd keenly from where he stood, and as the youth reached out for the tea he felt himself blushing unexpectedly. He saw in the grocer's assistant everything he admired, his shirt stretched tautly across his broad shoulders and forearms, muscles rippling beneath the fabric. When he leaned forward to pick up the mug his shirt flapped open to reveal a glimpse of a bare chest.

Wendy accentuated a feminine manner and put on a sweet girlish voice. "It's a grand morning outside."

"Aye, it is a grand mornin'." replied Judd, "It's going to be a hot one. It's hot already."

"There's a breeze getting up; it may be windy later, but it'll still be hot."

"Aye - Sorry to hear about Abby. You's Wendy, ain't you?" The mention of his name startled Wendy and he felt suddenly tongue-tied. Judd gave a canny wink and a nod of his head. "Abigail's a fine pal, but I keep my eyes 'n' ears open. I likes to know who's about."

Wendy's own eyes followed the village lad as he moved out into the centre of the room and his excitement throbbed as his muted gaze detected the unmistakable bulge in the front of his trousers. He didn't seem to be wearing underwear, and a long thick shape was well defined.

"Penny for your thoughts." said Judd, watching him.

Wendy's heart missed a beat and he guiltily dragged his eyes away from the tantalising shape and stared at the floor. He knew exactly the kind of act he needed to put on to please a youth like him: submissive, shy, cute and girlish. "Oh - nothing." he murmured faintly.

A smile played about Judd's lips as he took a pace nearer to lift his chin with a fingertip and looked down into his face, his light brown eyes reflecting unmistakable interest. Wendy felt strangely uncomfortable, but he shook with the pleasure of having such a brawny youth standing so close and paying so much attention to him.

"This is a good drop-o-tea you've made." Judd remarked, then he added with an earthy rasp. "You's a winsome lass and' no mistake, Wendy. I's been watchin' you on 'un off for a while lately. You's got a nice cute shape to you, an' a sweet little waggle on yer backside when you move. I reckons you's a girl who as all kinds o' talents."

Wendy glanced up and blushed coyly, eyes wide, lashes fluttering, mouth slightly open in a sensuous expression of mock surprise. "You're teasing. Don't be silly." It was a gentle rebuke accompanied by a beam of pleasure.

Judd stood closer. A bit too close. Close enough for Wendy to smell the scent of work on him. "I'd like to meet you some evenin'. Somewhere where we can be alone." Judd rumbled.

Wendy saw the desire in his face, recognised the lust in his partially open mouth and quickening breath. Standing there in front of all that was almost electric. He'd like to have reached out and touched him, but electricity could be dangerous. "I can't get away from here. The tutors are very strict, I could never ..."

The youth took a step back as if weighing his thoughts. It was only a moments aberration. Judd then came on again, loomed over him and pressed even closer. His body was firm and warm and his arms were about Wendy's slim girlish waist and squeezing him before he realised what was happening. He was overcome by the erotic force of the village boys embrace and simply clung to him while trying to quieten his racing pulse. The strength and warmth from Judd's hands mocked any attempt to ignore them, his body tingled and he feared doing an unplanned cum in his pretty panties. He wanted Judd to take him. He wanted him to command him and possess him.

Judd's lips brushed his cheek like a feather, then kissed him gently on the mouth. Wendy was frightened and fearful, but as his own penis begin to stir in his knickers as his face flushed with excitement. His breath quickened as he felt the heavy beat of his heart against the older boys chest. Judd's mouth went down on his own, one arm snaking around him and hold him tight while the hand of the other rose up to cup the back of his head. He kissed with more passion this time. His lips were firm - on his mouth, on his neck, on the curve of his throat, and Wendy couldn't help but revel in such adoration. In a place of shared delights between sissies Wendy had found himself a man and he was in love again.

With complete confidence Judd took one of the she-boys hands and placed it on the front of his trousers, and Wendy jolted as he felt the hard dagger leaping inside. Judd smirked. "I noticed how you were lookin' at me trouser-snake. What do yer reckon to it then?"

There was no going back. The village lad pulled his young lover onto tiptoe and rocked him from side to side as he pressed the arousal in his trousers against his belly. Wendy panted, quite happy to be the weak little girl. "Crikey Judd, we're being naughty. I'll be in awful trouble if someone sees us."

"I'll come back later tonight on me bike an' get into the east-wing. Nobody lives there, so no one will know if you join me."

Wendy sighed, aware of the hands fluttering over him, smoothing and exploring and feeling everywhere. He was more in love at that moment than he had been for months.

"I'll expect you then," Judd half-stated, half asked.

"Okay, yes I'll meet you later." Wendy agreed breathlessly, and he shivered as Judd's rough hands lingered around the hem of his skirt before slipping under to palm his smooth, pliable buttocks.

"That's what I wanted to hear, an' if you're gonna be my girl tonight you won't deprive me of something to be going on with, will yer?" His strong hands rose up and began to heave down on Wendy's shoulders, making the younger man's knees buckle, and he kept pushing until he was kneeling on the floor and looking hot and bothered.

Wendy watched with bated breath as the visitor eagerly unbuttoned the front of his trousers and dug one hand deep into his fly. Judd was a beast. What was he going to do? Goodness it was exciting!

The teenager had to dig and tug, but in no more than a few seconds he'd pulled his throbbing penis out. "We's got a few minutes afore ol' Larkin needs me, so try gettin' yer tonsils around this. A sweet thing like you should be able to manage that easy enough."

It came as no surprise to Wendy that such a teenage hunk had such a good tool between his legs. The thing looked as big as he remembered Abigail's to be, a long column of stiff flesh with a thick prominent vein traversing a tremendous truncheon of firm flesh, the foreskin already drawn back to reveal the flared ridge and a smooth-looking helmet shaped tip. It was so solid looking, so huge, so demanding. "Big enough for you?" Judd asked, his grin wide and hot.

Wendy didn't know what else to do, so he nodded his head, batted his eyes and giggled like a real schoolgirl while staring in girlish fascination at how the gland curved up to display the slit in the flaring cock-head. Judd took a step closer with his erection sticking out in front of him and wagging obscenely.

"Go on, honey-bun - have a taste - take it!" Judd urged, his voice edged with raw with need as he guided Wendy's face towards his crotch.

Wendy hung back no longer. He stroked the cock with his mouth, kissed it and flicked his tongue against the purple head before closing his mouth about its hot dimensions. As he rolled his mouth around to savour the size of it Judd gasped an exclamation of delight.

"Hah! You's got a good mouth on yer me little flower, I can tell straight away you's not new to this kind o' thing." He grabbed hold of the head bobbing in front of his thighs and steadied it, then made Wendy's lips glide right down to his balls. "We ain't got too long, so keep still a minute while I fucks yer face."

He pumped furiously back and forth for a short while pushing his cock to the fullest limits of the obliging she-boys mouth and using the clinging lips as an aid to masturbation. He shook when his orgasm finally erupted, unloading fiercely, almost making Wendy choke with the vast flood of hot, syrup-like semen that suddenly leapt into his throat, but he held his cock in the sissies churning mouth and made him take it all - made him gulp it down just as a good girl should.

Snurge
Snurge
133 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

READ MORE OF THIS SERIES

Similar Stories

New Beginnings Guy is feminized by mothers's assistant.in Transgender & Crossdressers
How I Became a Cheerleader Guy changes schools, life and sex to fit in.in Transgender & Crossdressers
Sin of Vanity Ch. 01 Marcel brings sissy Vance to Carol for feminization.in BDSM
My Little Slut Sissy boy slut finally gets used by Mistress.in Fetish
Her Good Little Boy Mistress uses her boy for his body's true purpose.in BDSM
More Stories