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71
Active Sissy Stories
/ Re: The Second Floor
« Last post by BabyJay on June 23, 2025, 10:26:23 AM »
Finally, He's taken the first step into the realms of Feminised Sissyhood. I hope Emily will induct him gently in to his new world. Await with anticipation.
72
Active Sissy Stories
/ Re: The Second Floor (#24)
« Last post by petticoated on June 22, 2025, 08:14:44 AM »
Leighton's deepest fantasies...his most arousing fetishes...had collided. And no matter how much (or how little) he might want to deny or resist where this might lead, he was in way over his pretty little head. The looming image of a Feminized Allen and these two incredibly beautiful, Feminine, and controlling Women were way out of pretty little leighton's league. And to think he had foolishly harbored  momentary far-flung aspirations of finally finding a potential girlfriend with Emily! This night was destined to exceed even the "friend zone" scenario that leighton had come to accept time and time again. Tonight  his delicate little fingers already had been strategically and purposely guided by Dorian to rest squarely on the wide white French Lace hem of Her minislip. Her white wool miniskirted power suit spoke volumes about who was in charge. And it was made very clear that this tall Blonde Goddess would brook no nonsense from Her "administrative assistant," Allen, who She had openly referred to as "Allison," promising to ~"Petticoat"~ him if he failed to perfect his curtsy. Would She really humiliate him? Tonight? In front of another "man?" Then there was Emily. And Her Dress! OMG! HER ~Dress,~ indeed. ULTRA~Feminine.~ Powerful. And the undeniable ~Envy~ of every Effeminate sissy wannabe, including leighton. Now, in the girly confines of this UltraFeminine bathroom, as leighton obediently, albeit hesitatingly, removed his male trousers and discarded his boxer shorts into the pink trash bin, his weak...and trembling little fingers daintily took the sissifying white bridal satin and ruffled white French lace thong, slowly pulled it up his nearly hairless feminine-like legs, adjusting the shameful sissifying pouch to excitedly (he couldn't help it) accommodate his embarrassingly small little "soldier," the cool bridal satin already was at work, heightening poor leighton's arousal while weakening his token resistance...
73
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Baby Mac on June 20, 2025, 10:19:28 AM »
Please have the females dress as villainesses and fight him
74
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on June 20, 2025, 05:02:28 AM »
Chapter 195.

Timothy spent the afternoon with Jasmin and Ellie.  Lavinia had warned them to treat him with kid gloves – she didn’t want anything else scaring him off.  So they did all they could to appeal to his ego, flattering him shamelessly and playing the innocent, adoring underlings – the polar opposite of their natural selves.  And Timothy, being Timothy, swallowed it and wallowed in it.  It had the desired effect, of quite restoring his confidence.

So it was with fewer misgivings that, on the following Wednesday, he returned to Pitt’s Wood and to the stable with a green door, in response to a phone call from Nicole.
“Cynthia’s finished your first outfit, Timmy – I hear Timmy’s your official name now – and you just need to come for a fitting.  Lavinia will pick you up and Cynthia and I will meet you at the stables.”
“Okay…  Er, what’s it like…?”
“You’ll see.  I think you’ll like it.  It’s rather too macho for my taste, but…”
That cheered him up even more.  “Oh, really?  Okay, I’ll get ready.”
“She’ll be at yours about eleven.  See you later, then.”

An hour and a half later Timothy and Lavinia were walking down the path between the stables and the field.  It was early, and, being a weekday and a school day, the Centre was relatively quiet, though all the permanent staff were hard at work mucking out, cleaning tack, and exercising the horses.  Jasmin and Ellie were working a few stables up from their destination, and they called to him and waved as they walked past.  He greeted them happily.  It felt as if he were already accepted as an important member of the team.  He was feeling slightly nervous, but also excited.  If the uniform was okay, starting next Monday he could look forward to making some proper money!

Nicole and Cynthia were waiting outside the green door, the latter carrying a yellow canvas bag. 
Nicole smiled, and Cynthia, to his surprise, gave him a hug.  Perhaps a hug of reassurance?  “Timmy dear, we’ve come up with our first design.  It should fit perfectly, if I got all my measurements right.”
“When do you not, Cynthia?” teased Nicole.  “All right, Timmy, are you ready?  Lavinia and I will wait out here.  We can’t wait to see what Cynthia’s come up with.  No, she hasn’t even shown it to me yet!  I have no idea…except she says she decided to use my suggestion…whatever that means.  Anyway, whatever it is, I really hope you like it…”
“So do I,” said Lavinia wryly.  “It’s too late to change it now…”
Timothy glanced at her face.  Was she joking, or…?”

Cynthia opened the stable door.  “Come on then, darling.”
As he entered, Timothy caught a glimpse of Ellie and Jasmin trotting down the path towards them.  Had they been invited to the fitting, too?

Once inside, Timothy saw that the stable floor had been swept, and a makeshift curtain had been hung across a corner.
“That’s your changing room, Timmy.  Now take everything off – everything, mind – and pass them out to me.”
“E-everyfing?”
He voice assumed a more businesslike tone.  “Yes, darling.”
“O-okay…”
He did as he was told, till he was standing naked behind the curtain.
“Good.  Now, there are only five components to your outfit.  Number one, pants.”  Her hand appeared around the edge of the curtain.  He took from her something smooth, cool, compact and yellow.
“These are…”
“Latex, yes.  Now pop them on, please…  Quickly – we don’t want to keep the ladies waiting all day.  The label’s at the back.  They should slip on easily.  It’s our new super-slick latex and I gave them a tiny smear of lube…”
He held them up.  His heart sank.  Fine bright yellow latex with tiny red latex frills.  He wanted to protest, but to tell the truth he had become a little frightened of Cynthia.  At first she had seemed so motherly…  Now there was a strictness about her, an edge to her commands.
“Well?  Are they on?”
He stepped into them, and pulled them up.  They snapped neatly into place as if they had been made for him…  Oh, yes, they had, hadn’t they?
“Yes, miss.”
“Now your top.  Here.”
That was also yellow, with a big red letter T on the chest,  It only came half-way down his torso.  This was getting worse and worse.  It was followed by red latex gloves, and red rubber superhero-style boots.  He looked own at himself.  How could he possibly…?”
“Right, let me see.”  She pulled the curtain aside, looked him up and down, nodded approvingly, and plucked and tugged at his outfit till she was satisfied with the fit.
“Good.  Excellent.  The last thing is the cape.  Stand still.”
By now he was totally cowed.  He stood obediently while she fastened on his spandex-lined red latex cape.
“There.  You’re a real super-hero now, sweetie.  Let’s go show the others.”
She ushered him out.  Waiting for him were Nicole, Lavinia, Jasmin, Ellie, and three other girls he’d never seen.  He was greeted with gasps and applause.  One of the unknown girls rushed off  “to get Marcia and the others”.   He wanted the ground to swallow him up.  Nicole and Lavinia took snaps.  Cynthia simpered and rubbed her hands.
“The customers are going to love you, Timmy,” said Lavinia.
“Smile, Timmy!” cried Nicole.  “Please…just a quick one…  No?  Well at least try to look a bit macho, then!  At the moment you look like you’re about to burst into tears!  Put your hand on your hip.  That’s right.  Super.  Great pose!  Got it!” 
75
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on June 20, 2025, 04:54:03 AM »
Chapter 194.

At lunch, Timothy started to become aware that he may already have a certain notoriety.  He wasn’t sure how, seeing as he hadn’t even started working yet, but he was conscious of being stared and pointed at by girls at other tables.  There was excited chatter and giggles too, but whether connected to his presence he couldn’t determine.
“Miss Lavinia…?”
“Yes, Timmy?”
“Is it always like this here?”
“What do you mean?”
“All these girls…chatting and laughing like this…?”
“Oh, yes, I’m afraid it is.  You’ll have to get used to it.  They like to let off steam here.  Many of them have been doing hard physical work all the morning.  On top of that, they have to be so reserved and respectful to the riders and visitors, some of whom are those posh upper-class types.  It’s “yes, madam”, “of course, madam”, “three bags full, madam” all the morning.  Just wait till you start work.  You’ll have to serve a lot of those privileged women.  They like their servants – that’s effectively what you are – they like them to be obedient and submissive.  You’ll soon learn how to call them “miss” or “madam” and grovel.  And you’d better not leave a speck of dirt on their boots, or a square centimetre unpolished, or you’ll be for it.”
Timothy stared at her aghast.  This wasn’t quite what he’d imagined.  He’d thought…well, he’d thought everyone would respect him…that he’d be someone special, who everyone would look up to…
Lavinia could read his mind.  She gave him a short, reassuring smile, and sipped her coffee.
“Do you mind if we sit here?”
She looked up.  Two young stable girls were standing by the table holding their lunch trays.  They were smiling mischievously.  There was an empty table only a few yards away.  Timothy was about to point it out, when Lavinia spoke.
“Of course not.  Shift up a bit, Timmy.”
She and Timothy were sitting opposite each other.  The two girls sat down next to them, also facing each other.  Timothy felt self-conscious, and tried to ignore them.  There was silence for about a minute, though both girls were smiling and fidgeting as if trying to contain some private joke.  Then the girl sitting next to him, whose freckled arm, decorated with several coloured leather bangles, was almost touching his, turned her head towards him.  She had a mass of dark wavy hair, which fanned his face whenever she moved her head.
“Hi…are you one of the new boot boys, by any chance?”
Timothy was taken aback by this direct question, and despite himself, turned bright red.
“M-me?  Er, yeah…I…”
“We thought so!” cried her friend, a blonde with a long ponytail.  “You must be Bobby’s friend!  What’s your name?”
“Er…Timothy…”
“He’s officially called Timmy,” put in Lavinia.  “Goes better with Bobby.  What are your names?”
“I’m Pat,” said ponytail.  “This is Emma.  Hi, Timmy.”
“Hi…”
Emma hesitated for a moment, glancing at her friend as if for advice. 
“Is it true…?  I mean, there’s a rumour that, you know…  Bobby is gonna be wearing this really cute…I mean, cool…uniform…”
“Like latex or something…” blurted Pat.  “I mean, it’s just a rumour…” she added, seeing Timothy’s face fall.
Lavinia saw no reason to deny it.
“Well, don’t tell anyone else – though they’ll find out soon enough – but yes, it’s true.  In fact he’s going to have several outfits.  And yes, they’ll need to be latex, so they can be easily wiped down when they get dirty from all the mud and polish and everything.”
The girls faces lit up.
“Wow,” cried Emma.  “I can’t wait to see him in his uniform.  He’s quite handsome.  We saw him the other day, inspecting the stables.”
“And so are you Timmy,” said Pat.  “I don’t know which one of you I fancy the most!”  And she collapsed in a fit of giggles.
Timothy, still blushing, turned to Lavinia.
“Does that mean…I’ll ‘ave to wear, like, latex stuff too?  I thought I was going to get a choice!  That’s what I was told.”
“Well, you will get some choice, Timmy.  Maybe which one to wear first.  But of course it’ll have to be latex.  Maybe not all of it.  Didn’t you read your contract?  It says quite clearly you have to wear whatever the Centre prescribes.”
“That’s not fair!  Why didn’t Miss Poole tell me?”  He glared at the girls.  “It’s not funny!”
Lavinia couldn’t conceal a smile. 
“I’m not gonna do it.  People are gonna laugh at me!”
“Oh, Timmy, please.  Stop acting so macho.  In any case, you don’t have a choice, so you might as well make the most of it.”
“I do have a choice.  I’ll go get a job somewhere else.”
“Oh.  You really haven’t read the contract, have you?  You’re on a year’s contract,  If you leave any time within that year, you incur a penalty.  Now, how much was it?  Three months’ salary, I think…that’s not far short of five thousand…”
“What?”
“I’m afraid so…”
He stared at her.  “I’m fuc-ked, then…”
“Oh, and that’s another thing.  There are penalties for rudeness, disobedience, and swearing.  Not all of them just financial, either.  So I advise you to read the contract with a little more care, and adjust your behaviour accordingly.”
“Don’t worry, Timmy!” laughed Emma.  “We won’t make fun of you.  Not all the time, anyway…”  She looked him up and down.  “I wonder what sort of thing you’ll have to wear…”
76
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on June 20, 2025, 04:48:36 AM »
Chapter 193.

Once in Lavinia’s car, Timothy turned to her.
“Who were they?  And why was that other girl wearing that hood fing?  Are they friends of Nicole’s?  How do they know Bobby?”
“Oh, Kaiya and Barbara.  Yes.  Miss Poole once employed them as maids  - that’s to say waitresses – at one of the Centre’s parties.  Then they sort of, er, helped out at another party.  Sort of acted as Bobby’s chaperones…”
“Chaperones?”
“Well, I don’t know, friends, whatever…   Anyway, you can ask Bobby about it.  He knows them better than me.  Sounds like you’re going to meet them yourself soon, anyway.”
“What did you mean by a “session”?  What sort of session?”
“Timothy, I don’t think that’s really our business, do you?.  For now, let’s just focus on your training, right?”
“Sorry…”
“No problem.  Now, you’re going to need to learn fast.  We’ll talk about different types of boots – riding boots, fashion boots – ankle boots, calf boots, knee boots…”
“Thigh boots,”  added Timothy.
Lavinia glanced sideways at him.  “Yes…thigh boots.  Do you think you’ll be able to handle thigh boots?  On a girl with a mini-skirt, for example?”
Timothy shivered, and bit his lip.
“I told you, it’s not an easy job.  But if you want out, this is your last chance.  I heard from Miss Poole this morning.  She’ll be there today, and your contract’s all ready for signing.”
“Oh.  Brilliant.  It’s so exciting.  My mum’s dead chuffed I got such a good job.”
“Yes.  Lucky you asked about Bobby when you did.  A day later and someone else would probably have got it.”
She turned the car down the short track to the car park.
“We’re here.  We’ll go straight to the place – it’s right at the end of the new stable block.”

They walked down the hill between the two lines of stables to the yellow doors.  Now there was even a painted sign attached to the wall, “Boot Parlour.  Opening Hours 9am to 12 noon, 1pm to 5pm, Mon-Fri, 9am to 1pm Sat.  Please book at Reception.”
Lavinia led the way in, along a short corridor with a window at the back, and opened a door on the left.  The room was painted yellow, with blue tiles on the floor, and seats along the walls.  The walls were hung with horsey pictures.
“This is the waiting room.”  She gestured towards the left-hand wall.  “You can get water, coffee, and even a snack.  Now on the right we have the toilet, and that” - she pointed to the door in the corner – “is the door to the inner sanctum.  Let’s take a look.”

The boot parlour was ready for business, with two special padded reclining chairs with foot-rests, a bit like dentists’ chairs, at the far end, under high windows, and one at the near end next to the door.  They were fully adjustable for height, back and knee angle, and had foot-rests that were also adjustable, and could be folded up if not required.  The cupboards were finished and packed with kit, there were washing facilities to the right of the two chairs, and drains for washing muddy boots.  On the right side there were two simple waiting-room chairs for family, friends, or observers.  Timothy looked around, and examined the special chairs.
“Wow.  Cool.  What are these for?”  He pointed to pairs of steel rings fixed to the wall at varying heights either side of the main chairs.
“Oh…  They’re probably for hanging up tools or brushes or something.  Yes, she hasn’t skimped on anything, has she?.  And did you know you’ll have your own private room as well, in case you want to stay overnight?  I’ll show you on the way out.”

They spent a few minutes looking through the contents of the cupboards, which contained everything imaginable that they might need, as well as two largish cases with the basic tools.
“These are for use if you have to attend to someone who doesn’t have time to come to you – for instance, someone who needs a quick clean or polish in between events – say between show-jumping and dressage.  That may be important especially if, say, it’s a wet day.  So when you’re working you’ll also be on call.  I don’t know how it’s going to work out - it may be you’ll have quiet periods, or you may be worked off your feet.  No-one knows till it happens.  The whole thing’s a bit of an experiment.”
“What’s in them locked cupboards?”
“Don’t know.  I haven’t got a key.  More kit, presumably.”  She looked at her watch.  “Right, we need to walk up and see Miss Poole.  I’ll show you your quarters first, though.”
They made their way out through the waiting room into the corridor.  Lavinia opened a door opposite.  It was a large room with a sofa, a table and chairs, a television and a computer.  Three doors led off it.
“The kitchen’s through there, and you have two ensuite bedrooms.  She’s really thought of everything.  I hope it pays off…”
“This is really for me an’ Bobby?  It’s amazing!  So cool.  Our own place!  We can ‘ang out ‘ere instead of going ‘ome?”
“I think so.  You’d better ask Miss Poole.  Come on.”

Miss Poole was waiting for them in her office.
“Come in!  Welcome, Timothy.  Good to have you on board.”
“Good to be here, thank you, Miss Poole.”
He was learning fast the importance of politeness.  He had realised already that that was a vital part of the job – keeping the customers sweet.  It also meant bigger tips!
Miss Poole beamed.  “So…  You’ve had a look at your premises…  What do you think?”
“It’s amazing, miss!  It looks so professional.”
“And do you like your quarters?”
“They’ll really be ours?”
“Yes.  Is was an afterthought, but the adjacent stable was empty, so I had it converted, as you see.  Rent-free, Timothy.  I hope it will reinforce your commitment to the job, and to maintain the Centre’s reputation for good service.”
“I’m really grateful, miss.  And I’m sure Bobby is too.”
“It means that if you have to work overtime, or outside normal hours, you’ll have the option of crashing out here.”
“I really ‘preciate the fought, miss…  It’ll be like our first flat…”
“Good.  Excellent.  So, I’ve prepared your contract…”  She slid a slim sheaf of papers across her desk.  “Please read it carefully.  If you’re happy with the terms, sign it and return it to reception.”
“What about Bobby?”
“Oh, he signed his weeks ago.”
“Then I’ll sign it now…”
“No, Timothy, please…  Read it carefully and make sure you agree to all the fine print…”
Timothy flicked through it.  There were lots of clauses numbered and under various headings: “Hours”; “Payment Options”; “Duties”; “Uniform”; “Conduct”; “Penalties”; and so on.  He glanced at the payment options, just to confirm the sums Miss Poole had mentioned were correct.  They were.  He noticed that hours could be extended “in times of high demand”, and that such hours would be designated as overtime.  Duties?  It was along paragraph, but he knew what his duties were – so he skipped that.  Under “Uniform”, he noted that the responsibility for design, fitting and supply were delegated to Nicole and some company called Fantastex – that must be Cynthia.  Okay.  He’d negotiate with them about what he was prepared to wear.  He skimmed “Conduct” – “presentable at all times”…”uniform must be worn at all times on the Centre premises”…”attention to clients’ satisfaction”…”politeness”…yeah, he knew all that stuff.  “Penalties” was divided into sub-headings: “Contract Term” [yawn]. “Conduct and Behaviour” – yeah, be nice to the punters, right?  No probs.  Well, if it was good enough for Bobby…
He borrowed a pen and signed it on the spot.  Miss Poole signed another copy and handed it to him.  She looked extremely pleased.  She folded the copy he had signed with great care, slipped it into a large envelope, and put it in her safe.  She rubbed her hands.
“There.  I think we’re done.  Lavinia, why don’t you introduce Timothy to Jasmin and Ellie?  You’ll find them at the far end of the old block – stable with a green door.”

They walked back down the hill along the old stable block.  Girls were mucking out, horses were being saddled, a couple were mounted and trotting around the field to his left.  So many cute girls, mostly about his age to!  Some dressed in old jeans and T-shirts, working around the stables, others immaculate in boots and breeches.  Several, he noticed, seemed interested, looked him up and down.  Yeah, well, don’t suppose they see many good-looking blokes here.  Looks like it’s all women.  I’ve come to the right place.  Many seemed to smile as he passed.  One or two laughed, and one got the giggles and actually snorted with mirth!  What’s her problem?  Just wait till I’m Assistant Boot Boy!  Then you’ll be pleading with me to squeeze you in ahead of someone else, right?

They had arrived.  Lavinia knocked end entered.  Jasmin and Ellie were seated on haybales laughing about something.  They jumped to their feet and tried to look serious.
“Miss.  Good morning.”
“Hi girls.  Well, meet Timothy.  Timothy, this is Jasmin…and Ellie.  They’ll be doing most of your training.  Probably in here…is that right, Jasmin?”
“Yes, miss.  We have everything we need.”  She glanced at Ellie, and Timothy could see they were struggling to keep straight faces.  What was the matter with the staff here?  In any case, he was senior to them now – mere stable-girls.  He tried to look stern, but they couldn’t meet his eye.  Ellie bit her lip and looked at the ground.
“What shall we call you?” asked Jasmin, composing herself.
Timothy was about to say “Mr Painter”.  It was as well Lavinia spoke first, or the girls would probably have collapsed.
“Yes.  Timothy, Timmy, Tim?” said Lavinia.  “Actually, let’s go for Timmy.  Then it’ll be Bobby and Timmy, Boot Boys.  That has a nice pretty sound to it, I think.  Yes.  We should have another notice made for the main door of the parlour.
Timothy didn’t much like being called “Timmy”.  It made him sound about six.  But he was in no position to object.
“Okay, that’s settled.  Right, now I’ll take Timmy for lunch in the staff canteen, show him around, and then leave him in your hands for the afternoon.”  She looked around.  “I see you’ve got a good selection of boots.  Were you in the Scouts, Timmy?”
“I am…in the Scouts…”
“Still?  Excellent!  Because you’ll need to be prepared…for anything!”
77
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on June 20, 2025, 04:35:03 AM »
Chapter 192.

Timothy wasn’t even off the premises before he was on the phone to Bobby.  Bobby himself had recently returned from training, and was nursing a very sore right buttock.
“Hello?”
“Bobby!  It’s me.  Guess what?  I’m gonna be your assistant at Pitt’s Wood!”
“What?”
“Yeah, true mate.  I’ve ‘ad an interview, and Miss Poole offered it me, an’ I took it!”
Bobby paused.  How much did he know?
“Okay…so what did she tell you?  What will you be doing?”
“I’ll be working alongside you!  You know, on the boots.”
“I’m not sure it’ll suit you, Tim.  Do you…I mean, do you actually know what’s involved?”
“Yeah.  I know everyfing.  I even know about…your uniform.  Your aunt showed me a picture.”
Bobby was alarmed.  “She did?  Why?  Why would she do that?  Listen, Tim, you can’t tell anyone, all right?”
“Nah, no worries, Bobby.  I know you didn’t ‘ave no choice.  I will, though.  The money’s great, ain’t it?”
“What do you mean, you will?  You’ll have to wear whatever they give you.”
“No, I don’t fink so.  Miss Poole said I’d ‘ave a choice.  Didn’t want me to be uncomfortable.”
“I see…”
Bobby made a wry face.  Poor innocent Tim.  A choice?  Yes, between the humiliating and the outrageous.  He’d been shocked at first, but now he was thinking it might not be such a bad thing to share his embarrassment.  Tim was a good guy, but he couldn’t imagine him being comfortable in anything his aunt had in mind for him.
“Lavinia’s gonna get me some training.  Some of the girls are gonna help.  There are so many cute ones there, ain’t there Bobby?”
“Yes, lots.  Cute in every sense, most of them.”
Timothy didn’t quite get that.  “Yeah…very cute…”

On Sunday he was summoned to Nicole’s to be measured for his outfit, and afterwards to meet Lavinia again to discuss training.  He had been instructed to wear a T-shirt and shorts in preparation for a visit to the stables.  He was nervous, but excited.  However, Cynthia was very reassuring.  She had the look of a kind primary school teacher, and smiled at him through her slightly too large black-rimmed glasses as they shook hands.
“Lovely to meet you, Timothy.  I hope between us we can come up with a suitable outfit for you.”
“She’s too modest, Tim,” laughed Nicole.  “She’s the design genius – I just approve the amazing things she comes up with.  It’s wonderful how she seems able to translate people’s personalities into clothes.  Cynthia – how do you see Tim?  Any first thoughts?”
“Well…  I would say, first off, very masculine, very adult.  Decisive.  Yes, that’s it.  I don’t see any wavering.  I see a strong will…commitment to what he does.  Am I right?”
Timothy basked in the compliments.  He stood very straight and involuntarily flexed his muscles.
“Yes, I think you are.  He made a decision to take this job, and within twenty-four hours he’d been interviewed and accepted.  He’s a hero.  So I would say, bang on, Cynthia.”
The two ladies looked at each other.  There was a silent conversation, undetected by Timothy.  Nicole nodded.  This meant “yes, very masculine, very adult”.  Cynthia winked back.  This meant, “don’t worry, I’ll soon do something about that…”

Cynthia looked him up and down appraisingly.  Right.  Off with your T-shirt, shorts and trainers, please.  Wow, flashy boxers!  Now, stand here.  Nice and straight.  Good.   Arms up…right…feet slightly apart, please…thank you…take a seat and let me check your foot size…”
She knelt down in front of him.
“So you’re going to supply everyfing – even my shoes?”
“Of course.  This is vital.  One wrong note can ruin the whole effect.”
“Er..do you have anyfing particular in mind?”
Cynthia knelt back on her haunches.  “Well, I don’t know.  One thing did occur to me just now, when Nicole called you a hero.  She was right – you and Bobby are both heroes.  In fact, I would say, super-heroes.  So that got me thinking…”
But at this point there was a ring at the bell, which curtailed that line of thought.  Lavinia had arrived.
“Hello Cynthia, Timothy.  How’s it going?”
“Just finishing up, Lavinia.  Then he’s all yours.”
“Great!  Tim, how much time do you have today?”
“I’m not doing anyfing…”
“How about we pop down to Pitt’s Wood.  I can show you the parlour.  It’s all finished.  And I believe we have a boot-cleaning kit for you as well.”
“Yeah!  That would be great!”

Timothy got dressed, and having said goodbye to Nicole and Cynthia, he followed Lavinia to the door.  She opened it for him, but as he went to step out he found himself face-to-face with two – no, three – young women, two side by side, and another behind. The two side by side were dressed similarly in T-shirts, jeans and boots.  The one behind…  Well, her face – or at least, her eyes and nose, was framed in a black latex hood which covered her whole head and even her mouth.  Aside from that she was wearing some sort of short blue gingham dress.
“Hello…” said one of the two, a black girl with her hair in short braids.  The other, a blonde with a pony tail, smiled, and looked him up and down approvingly.  Timothy just stared, until Lavinia stepped in. 
“Oh…hi girls.  Oh, and Chantal.  You’re here for a session, I can see.  Allow me to introduce Timothy.  Timothy will be joining Bobby at Pitt’s Wood as a second boot boy!  He just landed the job a couple of days ago.  Tim, meet Kaiya and Barbara…and that’s Chantal.”
Timothy managed to stutter, “pl-pleased to meet you…”.  Kaiya’s face lit up.
“Wow!  Well done you!  We’re gonna come and get our boots done, aren’t we, Babs?  Can’t wait!  Haven’t seen Bobby in weeks.  When do you start?”
Timothy, catching sight of her shiny brown thigh boots, swallowed hard.  It suddenly came home to him that this job may be more demanding, in various ways, than he had anticipated.
“Er…Monday the twentieth, I think…”
“Great.  We’ll make a booking.  Well, we’d better get on.  Nicole is waiting.  Come on, puppy.” 
It was then Timothy saw that she was holding the end of a sky-blue leather leash, the other end of which was attached to a collar around Chantal’s neck.  She gave it a tug, and led the way in.  Barbara let them go, and followed.  As she passed Timothy she gave him a wink, and whispered “see you soon, sweetie”.
78
Active Sissy Stories
/ Re: The Second Floor
« Last post by BabyJay on June 16, 2025, 05:07:18 AM »
Poor Leighton, his desire to please Emily will outweigh any misgivings he has. after all what's the harm? when he puts the pretty knickers on who is going to know apart from the two of them. Emily now has him hooked. How long will it take Her to fully transform him into the pretty little feminised sissy pet she wants? Looking forward to next episodes
79
Active Sissy Stories
/ Hommage Ă  Doris Day
« Last post by billykins on June 16, 2025, 04:57:42 AM »
When I was just a little boy,
I asked my mother, what will I be?
Will I be pretty, will I be rich?
Here’s what she said to me.
Que sera, sera,
A sissy you’ll be, you’ll be,
It’s already plain to see,
That you are, you are.

Then I put on my sister’s dress,
And asked my mother, what do you see?
Am I boy, or am I a girl,
Am I a he, or she?
Que sera, sera,
A girl to a tee, I see,
Grow into the real lady,
That you are, you are.

I wanted dresses of my own,
So to my mother, I made this plea;
I love pink satin, taffeta too,
And she replied to me:
Que sera, sera,
The shop closes at three, at three,
So let us hurry, hurry,
In the car, the car.

Now I have children of my own,
Beautiful daughters, one two and three;
They all love dresses, frilly and cute –
But not as much as me.
Que sera, sera,
My mother she was the key,
To living a life so free,
She’s my star, my star.
80
Active Sissy Stories
/ Re: The Second Floor (#23)
« Last post by petticoated on June 15, 2025, 08:46:40 AM »
Leighton swallowed hard. His face was on fire and his smallish fingers were shaking as he examined the shamefully emasculating garment. It was ALL ruffled white lace on the outside. The back thong also was all ruffled white lace. As Leighton turned his attention to the inside lining of the pouch, it was white bridal satin. It had to be. Smooth, cool, and as he knew, unrelentingly arousing. It was deeply and unabashedly effeminate. No man...no real man would ever wear this! But deep down Leighton knew he would be unable to resist putting it on for Emily. Any misplaced far-flung fantasy he may have harbored about finally finding a beautiful Girlfriend in Emily had quickly been extinguished by Her. And yet...he had to be near her. Her Femininity. Her magnificent five-tiered white tulle minidress. Her white lace corset. Her 5-inch open-toed slingback heels. Her makeup. Her long thick jet-black hair. Her incredible beauty. Her Femininity. Her Control. Yes, leighton would do ANYTHING just to be around Emily. Anything. And She knew it. Her own special pretty boi. After all, Emily reasoned, every strong Woman deserved to have Her very own special pretty boi. And leighton was pretty already. Effeminate, for sure. Easily intimidated by powerful Feminine Women. Envious of Their Femininity, especially Their pretty Dresses. As leighton gently held the sissifying confection of cool bridal satin and ruffled white lace, he laid eyes on a small envelope in the box. It was pale pink, with white images of ballerinas in frilly tutus. He knew these images. He had seen them before. As he opened the envelope he removed the card and read the hand-written message: "I hope I got your size right, leighton. small? I thought so. It is pretty, isn't it? It's double-layered bridal satin to give you that tingling sensation. Don't worry, it's leak proof, just in case you get overly excited this evening. I wanted something extra frilly and lacy for my little boi tonight. Now...be a good gurl and put It on for Me. And don't keep Me waiting. By the way, throw your silly male underwear in the pale pink trash bin. You won't be needing them tonight." It was signed, "Em."...
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