tagNovels and NovellasA Sissy Saga Ch. 02

A Sissy Saga Ch. 02


When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness.

"Better make a start," he said, "If we loop a cord around your middle it'll give you something of a waist and make your skirt flare out more."

William noticed that his cousin's face was lovely and made-up to feminine perfection, and when he spoke his voice was in keeping with his sweet features. He seemed surprisingly calm about being made to wear a frock and lipstick, but full of doubt and unused to standing in shoes that raised his heels he himself sank down onto the Chesterfield. Frowning and biting his lip, his eyes followed his companion, gazing in wonder at legs sheathed in sheerest black nylon. He couldn't deny Archie looked good in a skirt and stockings, and the raised heels of girl's shoes provided a sort of tension that gave the back of his legs a marvellous shape.

"Well, what do you think?" Archie asked when he returned to tie a velvet strap about his waist and then began brushing his blond locks with an onyx hairbrush. "Do you like the way your outfit feels?"

"No I don't. I hate it," William fumed. "I'm a man and I don't want to wear dresses and girls underwear. Jennifer shouldn't be allowed to make me do it."

Archie unzipped a small red bag full of cosmetics. "Did you tell her that?"

"Yes, well sort-of, but she's awfully cruel. She nanny-spanked me over her knee in the garden, then nearly pulled my balls off a few minutes ago. Well I mean that's not right is it? She's only a girl."

"You're cute. You're just the type she likes to smack, and exactly the kind she likes to put in a skirt."

"It's degrading to make boys dress like this. Everyone will think we're weird, and it's all your fault for kissing me yesterday."

"You liked me kissing you."

"Yes - well, but just look what's happened because of it. You've given Jennifer a chance to be a bully."

"She's always a bully, and she's awfully fierce, isn't she? She says she'll not marry until she finds a rich boy who can beat her in a fight, but she does exercises every day and she's stronger than most boys, so I think the rest of us will have to suffer for quite a while."

"Your mother - Aunt Miriam - she should stop her from being so beastly."

Archie sighed as he contemplated turning his cousin into an erotic young maiden like himself. Like himself William was beautiful, but in a different way. A degree smaller and softer and rather more camp.

"Mother admires what she does, and sometimes she puts me in a schoolgirl uniform herself when she takes me shopping." He reached out and stroked William's cheek. "Trust me. No one will think you're weird. They'll think you're a cute girl, that's all."

William wasn't reassured. The whole family were crazy. What they were doing was absolutely, totally and utterly wrong. The females were deviants, while Archie accepted things so easily it was unnatural.

Taking William's chin between his finger and thumb Archie said, "Sit up straight, I have to work on you."

Unaccountably William obeyed, stiffening his back and tilting up his head, aware of an odd sensation as his cousins delicious perfume assailed his senses and their stocking clad knees ribbed together with a whisper of nylon. The insignificant rasping signalled his first nylon-on-nylon experience, and it made something throb.

"You've a lovely complexion so you won't need much make-up," Archie gushed, "Nice features and a good mouth too, and you've eyelashes any real girl would die for. Your lips don't really need lipstick, but Jennifer will expect to see some so we'd better do it right. Shame you don't have pierced ears though."

"I've never been allowed to have my ears pierced."

"Jennifer will tell you all girls' have their ears pierced, but never mind for the moment, when we get around to earrings I think I'll be able to find a pair of clip-ons for you. We'll do your nails first, 'cos they'll need time to dry."


"Your fingernails you chump, they'll need to be lacquered. What colour do you think? Red is too harsh for you - I think primrose pink like my own. It's a colour people associate with young girls."

William's face darkened like a thundercloud and he gave his industrious cousin a petulant look as he twisted his hands in his lap. "I already look girly in these clothes. Do I really have to have make-up too?"

"Of course. Come on, you'll look really elegant, and you know you'll have to give in eventually. Jennifer will have you dressed like this for as long as you stay here."

"All the time? Every day?" The thought sent shivers down William's spine and a look of horror developed on his face. What kind of family had he blundered among?

"Certainly all the time. It amuses her to dress you as a sissy and watch you behave like a girl - for a few hours or a few months - for as long as it pleases her. You won't find any of your own clothes upstairs now. The cupboards in your room will have frocks in them. Look, your jolly lucky really, I have to put up with it every time I'm home on holiday."

William's face reddened and he squeezed his knees together. It seemed he didn't have any choice but to comply with what had been arranged and he needed time to think of a plan to escape the ghastly trap he'd fallen into. And, Oh dear. Why were things becoming stiff?

For the next twenty minutes Archie worked ceaselessly, all the time chattering in an effort to ease his cousin's concerns. He stroked a little lipstick onto his mouth and applied eyeliner to give him what he termed 'a surprised little girl look' then, when the cosmetics had been put away he slipped slender silver bracelets on his wrists and an elegant black velvet choker around his throat, tying it at the back with a bow.

"Perfect!" he remarked with approval, "You look really cute." To emphasis the compliment he leaned forward and kissed William lightly on the cheek.

William was overcome by the erotic nature of what was happening. His body tingled and his poor cock was in horrible distress and he feared embarrassing himself by cumming in his pretty pants. Then. Oh no. Archie was reaching under his skirt and touching - feeling!

Archie lifted William's skirt and pondered on the stiff, pretty shape inside a pair of filmy panties, a condition derived from rampant youthful hormones and pure lust. Not bad, he thought as he measured it with his slender fingers. "Better do something about that before you show yourself to Jennifer. She's a stickler for the way a skirt hangs, so it's best not to risk any unsightly lumps and bumps."

William gasped with erotic shock as his cousin reached under the waistband and eased the garment down his erect treasure, whimpering as soft fingers gently squeezed his testicles.

No, not bad at all, thought Archie as he caressed the eighteen-year-olds jewels. He slid his hand down carefully curling it around his scrotum until he held his testes in the centre of his palm. William had two well defined balls within a cute, pink bag and he had a cock that was quite stiff and smooth and deep pink at its tip, a tip already slick with preliminary drools. His right hand slipped around the slim hard shaft and his fingers squeezed gently, teased down the foreskin and pressing the smooth glands through his fist, rubbing the leaking goo over the pee hole with his thumb. Then he eased the pressure and started to stroke.

William trembled and gasped. "Ooh, Archie!" Immediately his pelvis began to rise up, straining and jerking and thrusting with an innate, urgent need. It was all so shameless but so very much needed, and he'd been yearning for such a thing to happen ever since he and his cousin had first met. The more Archie jerked his foreskin the more disinclined he was to object, and Archie was no slouch at understanding his pleasure.

"You like this sort of thing, don't you?"

"Uh, yeh, Archie. I, uh, well yeah, it feels lovely. You do it so nicely."

"All the girls say that."

William's ears were ringing with the rush of blood to his head and he heard his voice faintly as if it were an echo. He flushed. Did he mean real girls, or was he classing him as a 'girl'?

It was the wrong time for questions and he wasn't about to demand Archie stopped what he was doing. He was soon panting and rolling his head from side to side and rocking his hips.

He gasped, slumping down and opening his legs. "Do it Archie. Stroke my cock. Your hand feels so wonderful. Oh yes. Faster, do it faster."

His cousin obliged, his words being a spur to the hand working up and down on his rigid shaft. He changed to a full-handed grip and increased the tempo of his strokes to a rapid pounding.

"Ooh, oooh, ooooh!" William's chest heaved and he began to thrust his hips upwards. "Don't stop. Make me do it. Rub me faster and make me cum."

His cousin's eyes sparkled. "Faster still? Yes of course, if you're ready for it. And a gentle stroke under your balls too. That'll help."

William bucked sharply. "Oh, yes. Oh Archie I'm cumming now. Oh yes, oooh, mmmmmh!" A single splash of semen-cream leapt from his tense, throbbing stem to be followed by a lazier, warm ooze. It felt wonderful. Stomach clenching he panted and groaned, enjoying wave after sweet wave of rippling pleasure.

Archie had expected a quick finish and he stroked the beautiful lad lovingly, kissing his slender neck as warm cum slicked on his hand. "You shoot stuff beautifully. It's so sexy."

It was a proper reward for William, a youth who'd known so little joy so far that day. His skin glowed when it was over, and he felt not at all guilty. Archie was just the kind of young man he always enjoyed falling in love with.

Outside on the terrace the trip-trapping of high heels on stone alerted Jennifer to the approach of her two effeminated victims. Archie remained a step behind at a respectful distance, while heart pounding William stood in front of her, knees pressed together, head drooped and hands folded in front. The quite was absolute, and for William the tension almost tangible. The girl observed him with a stern look of appraisal, relishing his embarrassment and circling around behind the pint-size package of beauty that didn't even reach her shoulders.

"All dressed up in skirt and nylons," she simpered in his ear, "Now you really are a naughty boy, aren't you?" The remark was smug and mocking, making a shiver run down William's spine.

"Oh, please don't tease me, Jennifer."

She only grinned and husked into another ear. "Oh, but you are. You're a naughty sissy-boy showing himself off as a luscious little girly nymph. Does it feel sexy? It looks sexy. Do you feel ashamed? Most boys of any age would die of shame."

He pouted helplessly as she continued her tormenting. "Now you're a wriggly girl we can't call you William anymore, we'll need to think of a girly name. What would you like to be called?"

William blushed for the umpteenth time that morning. With his heart beating hard in his chest so furiously he knew it must be visible his knees nearly gave way under him.

"Come along. Think of a name. I bet you've thought about it before. I bet you've thought about what you'd like to be called if you were a girl. If you can't decide I'll have to give you a name you may not like."

"I - I sort of like the name, Wendy." he muttered in hushed reluctance.

"Wendy." Jennifer wobbled her head as she considered it. "Yes, that's quite good enough. It could hardly be mistaken for a man's name. She gripped him firmly by the shoulders and turned him. "Now, remember how you promised to be a lovely girl for me, Wendy. Show me how you can perform in girl's clothes. Walk to the end of the terrace and back again. Don't rush. Keep your head up and lean back slightly from the waist." Launching him like a boat on the river, she added, "Take short strides and place one foot in front of the other as you go."

In the crannies between the slate flags were planted clumps of tyme and aubrietia, and inevitably there were also weeds, but for the most part the terrace patio was level and provided an adequate catwalk. He began to walk, treading measured steps, feeling his hips swaying beneath the hem of his tiny dress and being eerily conscious of the soft elastic tug of suspender straps holding his stockings in place. He'd never been so aware before of putting each foot in a certain place, but it seemed vital that he performed precisely in the way Jennifer had instructed. There was something unworldly about the sensations he felt. There he was, a young man, parading in a short underslip and a pair of daringly skimpy thong pants and submitting to being the play thing of a heartless teenage girl.

At the farthest extent of the patio he paused, backed elegantly to the left, swung his hips around in a faultless Paris-turn, and sashayed back right on cue.

Standing at his sister's side Archie breathed heavily, impressed by such impromptu talent. "Wow. He's a natural isn't he? And such gorgeous legs too."

Jennifer nodded. "Yes, he's rather regal. Keep your arms straight as you walk back," she told William, "Fan out your hands and try a little wiggle - oh yes, lovely, and such a cute, sulky mouth too. You're going to make quite a little princess."

Before William was able to complete his return she signalled for him to stop.

"Go to the kitchen and get me some fruit juice. Gloria knows you're a sissy that I'm making you into a girl, so she won't be surprised to see you dressed like that."

As he obediently went off he noticed Jennifer cruelly twisting her brother's ear.

"There were a couple of things you could have done better Abigail, and of which you need reminding." she said as she hauled him towards one of the basket chairs. There was no doubt in William's mind that his cousin was in for some unduly rough treatment, but he could only feel glad to be away from the bullying girl himself for a while.

His mind became filled with resentment. His situation was ridiculous, but how could he change it? No one was prepared to criticise Jennifer, and he would have preferred staying with his grandmother to suffering anymore of the humiliation she provided. But Aunt Miriam held his allowance and he'd no other money, and her house was in the middle of a wilderness hundreds of miles away from Brighton.

He tottered carefully down the dusky corridors still unsure of himself in his towering high heels, and for the same reason he twice as carefully descended a short flight of steps carpeted in red that led to the kitchen. The house was a confusion. No two rooms appeared to be on the same level. In a small lobby he found himself confronted by a full length wall mirror. It was of another time, the heavy, gilded rococo frame a riot of twisted scrollwork with, at its corners, plump little cherubs bearing oddly knowing expressions.

Alone and unobserved for the first time that morning unbidden, illicit excitement coursed through his veins. Guiltily he cast a look around and shivered, hardly daring to look at his reflection, but eventually the temptation became too strong and he stepped back to view himself. The lobby was unlit and in shadow, so in the mirror his figure stood out against a dark background in stunning detail, and he was shaken to the roots by what he saw. It was absurd, impossible. He was being admired by an adorable young girl with peaches and cream complexion and a luscious little mouth. What nice unblemished skin she had, what lovely shoulders and what a slender waist.

Without being too conceited he knew he was well made and he couldn't help but admire his reflection. Yes, he did look a bit like a girl, he couldn't deny that. His big brown eyes and slender eyebrows did nothing to dismiss the fact, and his stocking clad legs were heart-stoppers. The skimpy black satin underslip he wore as a dress seemed to trickle down over his cool skin accentuating every youthful angle, every dip and sylph-like curve, and emphasising a lissom shape and lovely thighs, while the bodice beneath the swooping neckline hugged him deliciously. As he readjusted his clothes he realised he'd never felt so glittering and attractive. The sensation of nylon and satin caressing his skin made him feel giddy. Lipstick pasted on his mouth, earrings that swung against his neck and the stockings and shoes, all combined with a delicious swirl of the little skirt to summon up feelings of the erotic. His eyelids drooped and his cheeks became suffused with modest blushes as he absorbed a sudden wave of femininity.

He smiled coyly. "Wow. This is weird. Being dressed like this could make anyone feel a bit girly."

The image he saw was alluring and undeniably erotic, and he couldn't resist the temptation to flirt with himself. A coquettish smile developed on his mouth as his mood changed, and without understanding exactly why he struck up a pose that was intuitively sexual and feminine, one knee slightly bending and a hand lightly poised on a thrusting hip. Acting provocatively for his own amusement he swivelled around gracefully to make his skirt swirl, then teased himself with a shameless pout of a glossy pink mouth. He was suddenly aware of the stir of hormones inside his pants as his penis began to throb and push at the material. Hesitantly - guiltily, he raised the front of the dress and despite the attention he'd received from Archie just a short time ago he slipped a hand down inside his underwear. His penis felt thick and his testicles formed perfect oval mounds of their own.

"Is someone there?" A voice from the kitchen brought him shuddering back to reality, and shivering, he straightened his clothes, turned from the mirror and walked away.

The kitchen was a large place smelling of chopped mint and freshly sliced lemons, full of modern conveniences, but dominated by a huge Aga set in one wall. Laid out on a table were the makings of Sunday lunch: smoked trout, salad, blue cheese and a bowl of cherries.

Gloria was at the sink peeling potatoes. A large person encased in a blue overall coat with short sleeves that accentuated her gargantuan bosom, wide shoulders and plump short forearms shaped like muttons. Tossing a potato into a saucepan the woman stopped mid-bustle and latched her attention onto him, her pale eyes hardly blinking as she surveyed the lovely young sissy, resplendent in his tiny miniskirt and shapely stocking clad legs.

"Well, ain't you the glamorous thing. You's look sweet. Girls clothes suit you." she observed with a warm smile.

"Jennifer made me dress-up like this. I didn't do it because I wanted to," William bemoaned fitfully.

His distress had no impact. The broad bodied housekeeper displayed no hint of sympathy for his predicament; she just nodded while retaining her smile. "I guessed that a'ready. Jennifer as a talent for makin' lads do things they don't want to do. It's strange how just a few fancy bits an' a little skirt can change 'em. Jennifer allus makes boys wear such skimpy dresses, but I suppose she knows what she wants. It does make you look cute, an' you've got lovely legs. What's your name now you're a girly?"

The woman was outrageous and William felt himself rile, but had to accept he was helpless against her callousness.

"Jennifer said I'm to be called Wendy," he replied sulkily.

"Umph. Miss Hancock won't reckon that classical, but I suppose it serves the function. "

"Jennifer wants some fruit juice." he said hurriedly, wanting to change the direction of the conversation.

The woman smirked mysteriously. "Aye, she's fond o' juice is Jennifer." She took a jug of orange juice from the fridge and assembled it along with a glass tumbler on a small silver tray. Plink, plink! To lumps of ice were added before she handed the tray over to him. "Can you get this through the house without spillin' it?"

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