Ultimate Sissy Weekend Ch. 01

Story Info
Two sissies lock themselves into the sissiest weekend ever.
1.7k words
4.13
50.8k
38

Part 1 of the 8 part series

Updated 06/09/2023
Created 12/19/2019
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Dressed head to twinkle toes in beautiful baby pink, Sissy Susie nervously waits for her friend to arrive and the most humiliating weekend of her life to begin. She winces as her teeny clitty squirms in its pink prison, a chastity cage that's been on for four frustrating weeks. Her cage is safely tucked away in her pink ruffly panties, covered in sweet little bows and with 'Please Spank Susie!' in girly script on the rear. The wonderful petticoat keeps her pink maids dress nice and high, almost displaying her panties, but definitely displaying her bare shaved legs for all. The dress is covered in darling bows and has 'Sissy Fairy' written in glitter across the chest. The enormous ruffled sleeves make her arms look tiny.

Her slutty red lipsticked lips blow her bright pink nails dry. Even she can't believe how far she's gone with her make-up. Her cheeks glow with blush, and mascara and eyeliner highlight eyes covered in bubblegum pink eye shadow. Big red hearts have been lipsticked onto each cheek, so thickly that even a make-up wipe will leave shadows of them on her face for many days to come. She blushes anew and tugs nervously on one of the pigtails on her blonde wig, watching her giant pink hair bow bob adorably. She jumps as the doorbell rings, and quickly gets to her five-inch heeled feet. Sissy Tinkerbell is here! Which means the sissiest weekend ever is about to begin.

She minces to the door, gulps and opens it. She gasps as Tinkerbelle curtsies. Susie has only ever seen pictures online of Tinkerbell, and is not prepared for how she looks in person. Tink is wearing a beautiful green sissy dress, with large white wings, and an even bigger petticoat than Susie's, perfectly showing off the leg openings of her gold panties, tight around her cute rear. She is holding a ridiculous wand in one hand, an electronic juvenile one that makes a loud sparkly sound and says "sissy!" loudly whenever Tinkerbell moves it even slightly. Her blonde hair is in a cute fairy bob - of course - and with a big green hair bow. But Susie's eyes are drawn to Tink's earrings, two golden bells that ring loudly when she minces about. Her make-up is even more OTT thank Susie's. Her white tights lead to a pair of green tap shoes with a three-inch heel, perfect for drawing even more attention. She certainly doesn't need help there, as several onlookers laugh loudly as Tinks holds the hems of her dress and dips a curtsey, her wand announcing her a "sissy!" and her little bells ringing delightfully. Susie blushes anew as Tinkerbell says:

"Sissy Tinkerbell wishes to spend the weekend being a perfect pansy with her sissy sister Susie. Oh please can we be little chaste weaklings together all weekend long?"

She clasps her gloved hands together and starts hopping up and down, pleading and saying "please please please!" over and over, her shoes tapping loudly. The laughter only gets louder.

"Of course, sissy s-sis!" says Susie, dipping a curtsey of her own. "Please c-come in!"

"Oh thank you thank thank thank you!" says Tinks, doing a celebratory twirl. Susie catches the eye a giggling neighbour, a pretty lady in her early thirties, and quickly averts her gaze Oh God please can we just go inside.

"Come on in Sissy Tinkerbell" says Susie politely with another curtsey.

"Sissy Tinkerbell's suitcase is soooooooo heavy," says Tinkerbell, nervously clutching her wand with both hands. "Sissy Tinkerbell was hoping Sissy Susie could help her bring it inside?"

Tinkerbell waves her wand at a large suitcase next to a lamppost at the far end of the street. Susie realises with horror that Tinkerbell must have got the taxi to deliberately drop her off too early. Oh nooooo this sissy is the real deal.

"It would be Sissy Susie's pleasure," says Susie, curtseying again.

And so the two sissies mince down the front path and to the lamppost, to the giggling and wolf-whistles of Susie's neighbours. Tinkerbell keeps her wand raised the whole time and looks at Susie, who quickly raises her arms so her palms face out and they don't dip below her waist. Tinks smiles and nods as Susie minces sweetly up to the suitcase.

Sissies aren't known for being strong, and these two pantywaists are no exception. Together they struggle to heave the suitcase, moving it agonizingly slowly to the safety and seclusion of Susie's house. Forced to bend down and pick up either end, their pantied bottoms are on display for all, revealing that Tinks has 'Perfect Pansy!' written on her rear. It takes the two darlings twenty minutes to heave the suitcase into the house. Susie is exhausted and relieved, until she feels Tinkerbell taking her hand and walking her back outside. There, hand-in-hand, Tinks insists upon them curtseying to the neighbours. Finally, after over a dozen curtsies (Tinks insists on them being perfectly in sync) Susie is inside, the door shut behind her, her sissy secret now the talk of the neighbourhood.

Tinkerbell gives Susie a big sissy hug.

"Sissy Tinkerbell is so proud of you!" she squeaks. One of the sissy rules that Tinkerbell and Susie had written up was that the sissies always had to refer to themselves in the third person. The punishment for breaking a rule is to write it out by hand a hundred times.

"Oh!" said Susie, as she feels Tinkerbells soft hands squeeze her pansy bottom. Susie rubs her own hands on Tinkerbell's rear, and soon the sissies are making out, their clitty cages rubbing against each other in frustration.

'It would be so easy to take my chastity key out of the envelope' thinks Susie.

Instead, Susie is soon bent over in front of the mirror, a camera filming her as Tinkerbelle lifts up Susie's dress and slides down her panties. Tinkerbelle's wooden paddle has holes, to ensure big welts and blisters. Without warning Tinkerbell lifts the paddle and smacks it hard against Susie's right cheek. Susie squeals, composes herself, dips a curtsey to the camera and says "Sissy Susie is so grateful for her first spank! May she please have another?"

SMACK! "Sissy Susie is so grateful for her second spank. May she please have another?"

SMACK! "Sissy Susie is so grateful for her third spank. May she please have another?"

On and on it goes, until Susie's right buttcheek is even redder than her face. Her legs tremble and quiver, her waterproof makeup thankfully perfect even through her tears. As Tinkerbell finally reaches a hundred, she gasps with relief.

SMACK!

Susie jumps and stumbles, not expecting strike 101! Sissy Tinkerbell gives her a big smile and says "it's 100 per cheek Sissy Susie! And 20 more for not curtseying and counting like a good sissy."

SMACK! "Sissy Susie is so grateful for her one hundred and second spank. May she please have another?"

SMACK! "Sissy Susie is so grateful for her one hundred and third spank. May she please have another?"

Her spanking finally over, Sissy Susie now has to give Tinkerbell's cheeks a good reddening. Through her sobs, she diligently makes sure both sissy's are in perfect sync with their hot blistered bottoms. The spanking complete, Sissy Tinkerbell doles out an hour of corner time for them both to calm down. So the two sissys stand there, in different corners of the room, their hands on their heads and noses pressed to the wall. Sobbing and whimpering eventually leads to tedium, as the minutes pass agonisingly slowly for the two freshly-whipped weaklings.

Their hour is nearly up when the doorbell rings. Whimpering, Susie simpers off to answer it. The delivery man bursts out laughing, and snaps a photo of Susie's curtsey, before handing over a box that Susie can't recall ordering. Tinkerbell claps her hands and says its a present she ordered for Susie - they can open it after corner time, which, of course, they must start over.

So commences another dull hour of getting to know the wall. Susie thinks about her neighbours now knowing she's a sissy, and how soon a lot more people will know too. Speaking to Tinkerbell online made for some fun fantasies, but the scary reality of how far two sissies will push each other in person is starting to sink in.

Two hours pass before Tinkerbell declares double corner time over. Susie opens the box and gasps. It's a frilly childish backpack with 'ballerina' in feminine script. The backpack has a tutu! The small straps are tight on Susie as Tinkerbell helps her put it on, unzipping the gold heart zipper.

"Sissy Susie now has the perfect way to hold the envelope!" says Tinkerbell merrily.

Sissy Susie whimpers. It's time. She minces up to her bedroom and with shaking fingers picks up the envelope with her own address on it. Her brain begs her to reconsider as she skips back downstairs and hands it over to Sissy Tinkerbell. Tinkerbell smiles and opens the envelope.

"Is there a back-up?"

Susie shakes her head.

Tinkerbell puts four keys of her own in, then licks and seals the envelope with a kiss. Susie is confused.

"Sissy Tinkerbell has four clitty cage keys?"

Tinkerbell giggles and tells Sissy Susie to turn around. Susie feels the envelope being put in her backpack and the zipper closing. But then she hears a lock snap shut! She reaches behind and feels the padlock, sealing her into her sissy dress. Tinkerbell smiles and shows a lock on her own dress, then takes Susie's hand.

"Sissy Tinkerbell knows your nervous, but it's OK! This is how it's meant to be for sissies like us."

Susie starts to calm down, but then Tinkerbell reveals another surprise. With a flick of the wrist and a quick cold snap of metal, the fairy handcuffs her left hand to sissys right!

***

Susie is stood outside, Tinkerbell locked on her right, in front of the red postbox. The giggling is impossible to ignore. The wind on her bare exposed legs makes her shiver. The backpacks little bells tinkle. Susie takes out the envelope and posts it in the postbox. The sissies whimper as the envelope leaves their grasp. It's Saturday afternoon, so there'll be no post delivery until Monday. The two sissies are trapped in chastity, in their darling outfits, handcuffed together, for at least the next 48 hours.

"It's a bank holiday on Monday," whimpers Sissy Tinkerbell.

Sissy Susie's heart sinks. Make that 72 hours.

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zona_loserzona_loserover 4 years ago
loved it.

omg, i had to go back and read this again. Such imagination and detail. i'm a closet sissy myself and sometimes dress like that. oh how i would love another sissy miss to have a play date with. i loved the part about simpering outside in front of the giggling neighbors,, i would be so mortified if my straight laced neighbors saw me like that. please write another adventure for the sissy(s).

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