His Aunt Nicole

[Simonssister]

Chapter 260.

Ellie was in no hurry to get back and rescue Tim.  She waited in the canteen for the girls to show up as arranged.  She listened attentively as they related the events of the afternoon, a quiet smile on her face.
“Sounds like you did a great job, girls.  Miss Poole will be very happy.  He’s going to be rather miffed when I get back, I suspect.”
“He’ll be furious, I imagine,” laughed Phillipa.
“No, I don’t think so…” mused Ellie.  “Don’t underestimate the effect that device will have.  I know from experience there’s no better way of subduing a bloke.  Tim will know he has to be ultra-polite and nice to us if he wants it taken off.  He’ll be a pussy until then.”
“Yeah,” said Candy.  “But when it comes off on Saturday morning, imagine the reaction!”
“Ah…  I haven’t told you…”
“Told us…?” began Phillipa.
“The wedding’s postponed.”
“What?” the girls chorused.
“Yes.  Family illness.”
“But…?
“Miss Poole told me but asked me not to tell you.  She wanted you to go ahead as planned.”
“But we thought it was all about saving him for the wedding…” said Candy.
“Maybe that was part of it.  But maybe Miss Poole just wanted to see him punished.  She thought he was getting too full of himself, and needed to be put in his place.”
“Would she really think like that?”
“Oh, yes, Phillipa.  Don’t you ever repeat anything I tell you, okay?  Understood?”
“Yes, Ellie.  Understood.”
“Okay.  Miss Poole.  You must understand what drives her.  She created the boot parlour to make money, of course.  But she also likes the idea of two big boys having to grovel for the female staff.  She loves the idea of their humiliation and submission.  It’s her thing.  She gets all the videos  from the boot parlour sent to her by Evelina.  She thought the pageboy outfits would be really embarrassing for the boys, but then Tim used his to show off.  She wanted to remind him of his place.”
“Wow…  I didn’t realise…”
“So…what about the chastity device?” asked Candy.  “Will you take it off now?”
“Certainly not!  In fact, she wants me to make sure he goes to lunch in the canteen every day this week, so everyone can see his non-existent boyhood!  It’ll be obvious to everyone he’s been seriously emasculated.”
“So how long will he have to…?”
“Probably for a few days.  Miss Poole tells me that Serena’s snapped him up for the whole weekend!”
“Serena?  Oh my god…” gasped Phillipa.
“Quite.  I have to ring her tonight to confirm the booking.  Maybe I’ll find out more.  I’ll tell you if I do.  Imagine being at her beck and call for a whole weekend!  I’d love to be a fly on the wall.”  She checked her watch.  “But I’d better go – it’s late.  Poor Tim will be getting lonely.”  She glanced out of the window.  “Oh, and I think that’s Bobby and May!  Looks like he got his dress!  Must rush…”

[Simonssister]

Chapter 261.

As Ellie made her way between the stable blocks, she could see Bobby in his new dress posing outside the parlour while May snapped away with her phone.  As she got closer she realised just how amazing he looked.  She caught up with them.
“Hi guys…  Bobby, you look incredible!”
“Thank you, Ellie…”
“I mean it.  You’re really a girl!  Tim going to wet his pants when he sees you.”
“Is he in?” asked May.
“Well, sort of…  He’s recovering from a long hard session.  I’m going to go and sort him out, so keep out of the parlour for the time being.  In fact, why don’t you go up to the canteen and have a drink or something to eat, so I can get him cleaned up?  Then I’ll bring him up to meet you – and give him the shock of his life!”
“Okay.  I could do with a coffee at least.  Come on Bobby.”

Ellie let herself in, walked through the waiting-room and opened the parlour door.  She had to giggle, seeing Tim down on all fours, the rubber ball in front of his mouth, his eyes pathetic with that “it’s not fair” expression he sometimes adopted.
“Have a nice time, darling?”
She squatted down and pulled out the plug of his gag.
“Dear, dear.  Still half full?  Finish that up like a good boy and I’ll come and release you.”
Tim frowned and shook his head.
“Up to you, sweetie.”  She noticed the jar of condensed milk and the syringe, and thoughtfully topped up the reservoir.  “There, that’ll be more tasty.  I have to make a phone call.  I’ll come back and check in fifteen minutes.  If it’s empty I’ll let you out.  Oh, and there’s a nice surprise – no, a really nice surprise waiting for you.  So if I were you…”
She patted his head, stood up and left, closing the door behind her.  She threw herself down on the sofa in the living-room, and dialled Serena’s number.
“Serena?  Hi, it’s Ellie.”
“Hi, Ellie…”
“Miss Poole tells me you’ve booked Tim for the whole of next weekend.  I just wanted to confirm so I can put it in the book.”
“That’s right!  I was lucky that wedding thing got put off.”
“Yes…  Okay, that’s done.  Can you pick him up at nine Saturday morning?”
“Will do.”
“Any special requirements?”
“I don’t think so…  You have some masks and gags, right?”
“I’ll put them in.  How do you want him dressed?”
“Naked?  Is that possible?”
Ellie laughed. 
“No, I’m joking.  Actually I’ve already got him a little everyday outfit.  I’ll bring it with me.
“Okay… 
“I’ll come about quarter-to then.  Maybe you can help me get him dressed.”
“Okay…  What is it?  Is it going to fit him?”
“Oh, a simple outfit.  Nothing special.  Yes, I’m sure it’ll fit.  I got his size from that nice lady at Fantastex.”
“Cynthia?”
“That’s right.  Miss Poole recommended her.  She’s making him a couple of things for the rest of the weekend.”
“Is she…?”
“Yes.  My mum’s having a little bash on Saturday.  She’s changing jobs.”
“Your mum?”
“Yes.  I told her all about the boys.  She’s going to book a session some time.  She’s dying to meet Tim.”
“Right…”
“So as I say, she and her work friends are having a little get-together Saturday, then Saturday evening they’re going off for a few days on the coast – Norfolk, I think.  That means I’ll have the house to myself, and I’ll have a few of my mates round when the coast’s clear.”
“So Tim…”
“It’ll be a working weekend.”
“He’ll need his equipment then…”
“Oh, no.  Not that sort of work.  Just general domestic duties.”
Ellie laughed.  “Oh, he’ll like that…  Make a nice change from being on his knees all day…”
“I hope so.  Though I can’t guarantee he won’t be on his knees some of the time,” she added, archly. “Miss Poole is very keen the boys should learn new skills…  Widen their remit.  All that untapped potential…”
“Quite, Serena.  But I must tell you one thing.  He had a long session today with a couple of the girls, and ended up with a chastity device!  I’ll make sure to have that taken off before Saturday.”
“Chastity device?  Really?  No, don’t take it off – leave it on, please…”
“Okay, if you say so…  I’ll let you have the key.”
“Okay.”
“That’s all done, then.  See you Saturday.”

Ellie put down the phone and sat back.  “Fantastex, eh?” she murmured.  “Wonder what she’s getting for him from there.  I could ask Cynthia…  But, no.  That would be unprofessional.  It’ll all come out in the wash, anyway…”  She smiled.  “Well better go sort him out, I suppose…”

[Simonssister]

Chapter 262.

“Keep your head still, Tim!  Let me see…  Good boy!  Finished up your yummy c-ummy treat!  Okay.  Let’s get you out of there…  Goodness!  Is that the strap-on?  Did you really take all that so easily?  Was it nice?”
She unbuckled his gag and prised it gently out of his mouth.
“There…  Does that feel better?  It’s quite big…”
“My jaw flippin’ aches…”
“Oh, it’ll soon wear off.”
She released him from the cross and helped him to his feet.  He groaned and stretched.  Ellie glanced at the front of his shorts.  The usual eye-catching vertical bulge had been replaced by a cute little curled protuberance no thicker than a breakfast sausage, with a neat, slightly pointed, tip.  She couldn’t suppress a giggle.  Tim glared at her.
“It ain’t funny!  Do you ‘ave the key?”
“Sorry, Tim.  Candy kept it.  It wasn’t for me to…”
His eyes filled with tears.  “Please, Ellie…  Can you ask her for it?  I can’t walk around like this…”
“Oh, let’s leave it till tomorrow.  Then I’ll see what I can do.”
“Ask Miss Poole!  Please!”
“Well she’ll have left now.  Tomorrow, okay?”
“All right…”  He sniffed.  “Why did they do all them fings to me…?”
“Oh, don’t make such a fuss!  Don’t tell me you didn’t enjoy it.  I won’t believe you.  Now come on, let’s get you showered and changed.  It’s out of hours now so you can wear civvies.  And there’s a big surprise waiting for you, as I said.”

Thirty minutes later they were heading up the hill towards the offices, and the canteen.  Tim was wearing jeans and a T-shirt.  As they approached the top of the path Ellie caught sight of May waving from the canteen window, and she waved back.
“Is that Bobby?” asked Tim, peering.
“Bobby and May.”
“Where’s ‘e bin all afternoon.  Does ‘e know what I’ve bin frough?”

At the canteen door Ellie stood aside to let Tim go first.  He was half way to their table when he stopped dead, and his mouth fell open.
“What’s up, Tim?” asked Ellie, innocently.
“B-Bobby…?”
“Hi Tim!”
“Is that…you?”
“Yes, idiot.  Who do you think…”
“You look…fuc-king incredible…”
Ellie took him by the shoulders, marched him over to the table, and sat him down opposite his friend.  For some time he could do nothing but stare.
“See?  I got the dress.  And a makeover.  Do you like it?”
“It’s like my dream…  I mean, I can’t believe…  You look so…  Your ‘air…”
“It’s extensions.  I can’t stay like this.  But now I know I can really look like…almost be…a girl.  It’s an amazing feeling, Tim.”
“For me, too…”
Ellie and May exchanged glances.  Seemed like they were both happy now…

[Simonssister]

Chapter 263.

Later that evening Bobby and Tim and May and Jessica went out to eat at a local restaurant.  Bobby in his new persona.  It was to be the first of many such forays.  On that first outing Bobby attracted attention, all right – all from young guys.  Whenever this happened Tim, who spent most of the evening staring at his friend adoringly, became ridiculously jealous, and found himself holding Bobby’s hand, or putting his arm around him protectively, much to the amusement of the girls.  As for Bobby, he exploited Tim’s feelings continually, driving him to distraction by flirting with every other male he encountered.  He had finally realised the overwhelming power of being a pretty girl, and practised his sly glances and mascaraed flutterings at every opportunity…

The boys were fully booked the following week, and slightly downcast at the news the wedding had had to be delayed.  Tim’s lunchtime appearances in his emasculated state engendered general mirth, several memes, and for Tim himself, severe embarrassment.  Ellie told him he had a weekend booking, perhaps trying to cheer him up, but pretended ignorance of the booker, whilst Bobby found out his fate from Mélisande by text first thing Monday morning.  Her text began with emojis of a pony and a heart, followed by the news that “on Saturday me and mummy will meet you in stable 13 at 6am”, and promising him a proportion of the take from the pony rides on Sunday at the rate of “20p a ride!!  The rest will go to charity – but maybe you’d like to donate your 20ps as well???”  Bobby sighed. 
“Ellie?  Is this true?  Do I really have to do pony rides on Sunday?”
“Oh yes.  Miss Poole wants to make it a regular thing.  There’s a lot of interest, especially since she announced the idea in the monthly newsletter.  Ever since the show people are speculating on the identity of the boy dressage pony.  Now they have the opportunity to come and actually ride him!”
“But…suppose they find out it’s me…”
“Don’t worry.  You’ll be masked up, so no-one will know.”
“Mélisande’s gonna be riding me all Saturday, then I’ve got to give rides to a bunch of kids Sunday…  It’s too much…”
“Oh, not only kids, Bobby.  Miss Poole set the maximum weight at fifty-five kilos.  Why, I’m on about fifty…  Maybe I’ll come an have my fifty pence worth too…”
“What?  Fifty-five kilos?  That means most of the girls here…”
“Quite.  You’ll have a busy day…”

With full bookings the week sped by.  The boys were in pessimistic mood Friday evening, and went to bed early in anticipation of a difficult weekend…

Saturday morning.  Bobby was up with the lark, and had left before Tim was awake.  Ellie roused him at eight.  He blinked at her with sleepy eyes.
“So…who is it?”
“Who is it?”
“You know what I mean!  Whose booked me out for the whole weekend?”
“Oh, well…  Actually it’s, er…Serena.”
“What?”  He leapt out of bed.  “Why didn’t you tell me?  What does she want wiv me?”
“Tim…calm down.  I have no idea.”  She stifled a laugh.  “Well, actually, I think she wants to introduce you to  her mother…”
“Tim stared.  “’Er muvver?”
“Yes.  Don’t ask me why…  Oh, that’s the door.  That maybe her now.  Early…”
“I’ll get dressed…”
“Don’t bother.  She said she’s bringing your clothes with her.”
“What?”

It was indeed Serena, in jeans, ankle boots and a tweed jacket, and accompanied by two other women in their twenties.
“Hi Ellie.  We’ve come for the boy.  I’ve brought reinforcements just in case he tries to resist.  These are my mum’s work colleagues, Carly and Doreen.  Ladies, this is Ellie, the boys’ manager.”
Greetings having been exchanged, Serena looked around.
“So where is he?”
“You’re early.  He’s only just woken up, and it sounds like he’s in the shower.”
“Perfect.  Here’s his outfit.  Will he put it on without any argument, do you think?”  She handed Ellie a big pink carrier bag.
“He’ll do what I tell him.  Take a seat, ladies.  Make yourself coffee.  I’ll be back in a few minutes.”

She went back into Tim’s bed room and unpacked the bag onto his bed.  A little pink skirt, a Hello Kitty T-shirt, white socks, pink trainers, and a girl’s bomber jacket.  And a couple of pairs of stretchy satin panties, one pink and one yellow, with little bows on the waist.  She chose the pink ones, to match his skirt, and zipped the other pair into his jacket pocket.  She smiled, and waited for him to emerge.

He wasn’t happy, but he knew he had no choice.  Ten minutes later he was standing in front of the three visitors, being inspected.
“You’re a cute one,” remarked Doreen, surveying him with an experienced eye.
“You better watch ‘er,” laughed Doreen, pinching his cheek.  “Bit of a cradle-snatcher, ‘er.”
“Thanks a million, Ellie,” said Serena.  “We’d better get going.  Tim’s got an appointment at nine-thirty, and I need to get home and make the food for lunch.  “See you in a couple of days.”

The three woman marched him up to the car park.  Tim kept his eyes fixed firmly on the ground, but he could hear the gasps and giggles as he passed by the stables.  Would he ever live it down?  His worst nightmare – dressed as a girl.  For Bobby, fair enough.  For an alpha male like him…  Disaster!

Serena drove an orange Porsche.  Doreen sat in the front, Tim and Carly in the back. 
“So Tim – do you like your outfit?  How does it feel?”
He knew better than to object.  If he wanted to survive the weekend, he’d have to pretend compliance. 
“Okay…”
“You look really nice…”
She drove into town, and stopped just off the high street.
“Okay, off you go,” she said.
“Where are we goin’?” whimpered Tim, as her friends got out and pulled him from his seat.
“Your nails are a disgrace.  Before I introduce you to my mum, you’re going to have them sorted out.  Girls – see you back at the house, yeah?”

For Tim, it was a walk of shame, through the middle of town, busy with shoppers.  The women walked side by side and made him walk ahead of them.
“Good boy.  It’s only a few minutes’ walk,” said Carly, in a motherly tone.  “Sahana’s is the best nail salon in town.  Serena said you can choose the colour too – so long as it’s bright and glittery!”    Of course few people actually noticed the boy neatly dressed as a girl.  But for Tim, it was a big ordeal – so much so, that when they finally arrived at Sahana’s, he was actually relieved…

[sissyboy1212]

Another nice series of chapters. I admire how prolific you are and appreciate the care you put into your writing. You’ve definitely created an exciting world of characters with this imaginative story.

[Simonssister]

Thanks, sissyboy...

[Simonssister]

Chapter 264.

Tim had only a five-minute wait before he was called and seated in the middle of a row of ladies being attended to.  Naturally, he attracted a deal of attention, but for some reason on this occasion he didn’t seem to appreciate it.  His hands were examined by a smiling Asian lady called Koro – at least, that was what her name sounded like – who began by massaging some sort of lotion into them, and followed up with a through manicure to cuticles and free edges.  But it was clear he was going to need falsies if he were to impress Serena’s mother, and after some discussion between the manicurist and his chaperones, it was decided the most appropriate style would be medium-length rainbow-coloured ones which could be obtained off the peg.  A suitably-sized set were found, and glued securely over his own nails, with the instruction that he should not try to remove them for a least a week!

Whilst the process was going on, Tim found himself experiencing some confusing emotions.  On the one hand he felt embarrassed at the assault on his manhood, yet the manicurist was pretty and spoke to him so respectfully – calling him “Mister Timothy” – that he felt rather flattered, and also slightly excited by the transformation his rather ordinary hands were undergoing, and by the way she squeezed each finger between hers after each application.  Also, he was getting admiring looks and congratulatory encouragement from the other customers and even the owner!  His vulnerability to compliments and praise, especially from women, was already weakening his defences.  His cheeks, which a few minutes ago had been burning with embarrassment, were now, as he surveyed his beautiful new nails, flushed with pride.
“Shall we go show Serena?” said Carly, gently.  “She’s not going to believe how amazing they are…”
“Yeah, okay, Carly.  Let’s go.  Fank you very much, miss!”
His self-consciousness had almost evaporated as they walked back down the street and climbed into a cab.  Serena’s house was outside town, just off a country lane.  As they went along, Carly kept up the propaganda.
“I think Serena’s got you a few more surprises – though I don’t know exactly what they are.  I know she’s found some special clothes – much nicer than these.”
“Yeah?”
He wasn’t sure if that was good or bad.  But surely it couldn’t be bad, having all this attention lavished on him.
“Serena picked you especially…”
“She did?”
“Oh, yes.  She told her mum you were the handsomest of the two boot boys.”
Tim smiled.
“That you would look good in anything…”
“Really?”
“Oh, yes.  And you know her mum used to be a fashion designer.”
“Did she?”
“Yes.  And she said, “dress him and bring him to me.  I’ll be the judge.”  So if she likes the finished product, Serena’s going to get brownie points – and I’ll expect you’ll get a bonus.  Maybe even a fashion show of your own.”
“Wow!”  Tim said this because Carly seemed quite excited about it all – though he really had no idea what might be involved.  And he was beginning to like Carly a lot.  She smelt nice, and cuddled him a lot, which made him feel special.

Doreen instructed the driver to take them up the drive to the front door.  Serena was waiting.
“Come in, quick.  Mum’s in the back.  Tim, in here…”
She ushered him into a big, rather fussy bedroom.
“You can change in here.”
She gasped.  “Your nails!  Gosh!  So cool!  Do you like them?”
“Yeah…  Reck’n they did a good job, eh?”
“They suit you.  Now listen.  I want you to make a good impression on my mum.  I’ve got you a couple of outfits.  Mum’s only here today, so if you could look glamorous…  Well, I’d be grateful.  She knows all about fashion, about what clothes suit what person, but she’s suspicious of young women.  When she was in the business…  Well, they let her down too many times.  She likes good-looking men, and you have the right looks to wear any sort of clothes,”  She put her hand on his arm.  “Would you do it for me?  We’ll make you look incredible, I promise…”
She looked at him seriously, straight in the eye.  Her own were as blue as the sea in summer.
“Yeah, sure, Serena…for you…”
She suddenly became alert and efficient.
“Right.  I’ll get the girls to dress you now.”  She opened the door.  “Carly?  Doreen?  He’s ready…”