His Aunt Nicole

[Simonssister]

Chapter 248.

They had passed through a curtain which had fallen into shreds behind them, as through it had never existed.  There was no going back.  Without the prurient impositions of Diana and Eleanor it may never have happened, but that wasn’t important.  They both knew they weren’t really gay, and they jibbed at Eleanor’s whispered “sissy-boys”, though they could understand her justification in saying it.  But they felt no guilt or shame, and when they were finally released from their bondage, and had stretched and exercised for a minute or two, they looked at each other and grinned.
“Wow, Bobby
that were intense, yeah?”
“What a pervert you are, Tim.  I should have realised that four years ago.”
“If I am one, so’s you
”
“Yeah, I know
”

It was on the surface a simple relationship, but after all the years they’d known each other there was a lot more under the surface.  Tim had had a crush on his friend since secondary school, and whereas such childish affection between boys normally fades as the girls grow and become more appealing, in this case Bobby actually possessed more feminine allure than they.  Moreover he depended on Bobby in many ways, for comradeship, for loyalty, for guidance in life.  He respected Bobby’s intellectual powers, and relied on him to help him make the right decisions.  Reciprocally, Bobby liked Tim for his openness, his honesty, his habit of saying what was in his mind, his total lack of filters – the absence of the “persona”.  This he regarded as a rare psychological strength, and it was backed up by Tim’s physical strength.  When they were younger, before Bobby’s pony-work had built and hardened his muscles, Tim had been his protector on several occasions, when others sought to exploit his delicacy.   But there was more to Bobby’s feelings than a mere objective regard for Tim’s masculinity; the feminine element in his psyche also responded emotionally.  Their affection was mutual, as was the inclination to express it physically.

“We’re leaving, boys,” smiled Diana, and she and Eleanor put away the last aids in the special cupboards and locked the doors.  “Full marks for what you did today.  It opens up all sorts of possibilities
”
“We heard something about a dress, Bobby
” remarked Eleanor.
“Yeah,  That a way down the line, though.  Cynthia’s still working on the design, I believe.”
“What do you think about that, Timothy?”
“Yeah, well, if ‘e wants to wear dresses, let ‘im.  Suit ‘im, I reckin
” he said, evasively.
“Hmm
” was Eleanor’s only reply.

They were in a mess.  The parlour was in a mess.  They were wondering how to start, when Ellie arrived.  She took one look at them, and another at the floor, and burst out laughing.
“What’s been going on here?  Boot parlour?  Looks more like a milking parlour!  Look at the state of you two.  And why are your lips swollen like that
?”
The boys looked at the ground.
“Well, never mind,” she said, suspiciously.  “Just go get showered and changed.  I’ll mop up here.  Go on.  Off you go.”
“Thanks, Ellie
”
“Yeah, fanks
”
“Oh, and by the way, Saturday.  Tim, you have one customer in the afternoon, by yourself.”
“By meself?”
“Yes.  Phillipa.  She’s new so it would be intimidating to have both of you together.”
“Why me?  Why not
”
“We drew lots.  You lost.  Don’t look like that, please.  It’ll be Bobby next time.  So Bobby, you’re free.  May wants to take you out somewhere.  She’ll come pick you up at lunchtime.”
“Where does she
”
“No idea.  It’s a surprise, I think.  Okay?”
“Sure
”

When she’d finished  she paid a call on the girls.
“I don’t know what That Murchison woman and her friend had them doing, but they looked like they’d spent a night in a brothel!  I’m telling you, May.  It’s true.  There was c-um all over the fronts of their shorts, all down their legs and all over the floor.  And they both had swollen lips, like they’d been snogging – I mean serious snogging!  So you may want to give them a break from their, you know, education, tonight
”
Jessica and May looked at each other.
“Do you think
?” began Jessica.
“Well they weren’t snogging the ladies, cos I met them earlier when they were coming down the path.  Giggling a lot, but quite unruffled.”
“Then they must have been
”
“They must.  We’ll get it out of them.  That would be so cute
”

They went down straight after work.  Sure enough, the boys seemed rather low-key.  Happy, but for them, rather quiet.  May opened the conversation.
“So
  How was work today?  We were really busy.”
“Fine, May
  Yeah, fine, eh Tim?”
“Er, yeah
  Fine
”
“So were you busy?”
“Oh, quite busy
”
“Yeah, sorta quite busy
”
They were getting nowhere.
“I ran into those two women from the committee
what are their names?  Murkyditch and Bowson or something?  Coming from your direction.  Was it them?”
The boys exchanged glances.
“Oh, yeah, I fink so
”
“You think so, Tim?  Don’t you know?”
“Oh, Tim doesn’t know them very well
”
“But they were here before.”
“Were they?  Oh, yes, they were.  Weren’t they, Tim?”
“Guys – cut the crap,” interjected Jessica.  What happened?  Come on, spill it.”
The girls, by means of endearments and threats, they extracted the truth bit by bit.  They even insisted on inspecting the crime scene, and forcing the boys to duplicate their positions.  What the boys didn’t mention was the snogging.
“I always thought those two were perverts,” said Jessica, delighted, “but imagine dreaming up that sort of scenario.”
“It must have been planned for when they were building the place,” said May.  “Which means Miss Poole was also the instigator.  The entire committee must be in on the whole thing!”
“Did they take any photos?”
“Photos and videos,” admitted Bobby, reluctantly.
“Oh my god, they’re all going to be leching over them!” cried May; adding, “wish we could see them
”
“So boys,” said Jessica, slyly, “how did your lips get all swollen, then?”
“What?”
“Ellie told us, when she found you, your lips were swollen.  How come?”
“I
  No they weren’t
  She must have
  I mean, everything was swollen, cos of being in that position
”
“Bobby, tell the truth.  Ellie knows all about snogging – no-one more so.  So admit it.  You snogged each other.  You were forced to, I get it.  But that’s the truth, isn’t it?”
Their faces were enough admission.
“Show us how you did it.”
“Yeah, come on.  We want to judge how good you are.  Don’t be so shy.  Afterwards you can snog us.”
Eventually the boys gave in, and, sitting side by side on the sofa, exchanged some half-hearted pecks. 
“What’s that?” asked Jessica, incredulously.  “Tim – you know how to kiss.  Now kiss Bobby how you did earlier.  Or I’m leaving.”
“Oh, fer fuc-k’s sake
”
He grabbed Bobby in both arms, put a hand behind his head, and gave him a Timothy Painyer one-minute special. 
“Satisfied?” he asked, coming up for air.
“Bobby is, anyway,” remarked May, looking at her boyfriend’s dazed face and tousled hair.

[Simonssister]

Chapter 249.

Saturday lunchtime, the boot parlour.  Bobby in his civvies, Tim in full uniform, butt-plug set to zero – to avoid startling Phillipa – sulking quietly that he had to stay and work whilst Bobby went off having fun.
“Where you goin’ anyway?”
“No idea, Tim.  Some sort of surprise, May said.”
“Well fink of me slavin’ away ‘ere while you’re enjoyin’ yerself, won’t you?”
“The image won’t leave my mind for a second, I promise you.”
“Yeah right.  Now shove off before I kick yer out
”
With which fond farewell, Tim disappeared into the waiting-room on the way to check all his equipment was ready.  A moment later May walked in.
“Ready, Bobby?”
“Yes.  You’re not going to tell me
”
“No.  You’ll find out.  You’ll be happy – I think.”

It was half an hour’s drive.  As they pulled into the estate, Bobby twigged.
“Fantastex!  Why are we here today?”
“Cynthia has something for you.”
“Not my dress?”
“Not the dress.  But a dress, at least.  It’s as much a surprise for Tim as for you.”
“Wow.  That’s cool.  Do you know what it’s like?”
May parked outside the Fantastex building, an unostentatious single-story affair that had years ago been a manufactory of cardboard boxes, and still sported frosted windows along one side.  The front, though, had long clear glass pains and a colourful sign in puffy letters.  They climbed out of the car and entered.
Daphne was on reception as usual, sitting behind a till, on the phone to a customer.
“Yes, Wednesday.  Come early if you can – we get busy after about eleven.  I’ll tell Cynthia about the modifications.  Yes.  Yes.  Thanks, Mrs Cooper.  My pleasure.”
She put down the phone and smiled at them.  “You’re Bobby, aren’t you?”
“Yes.  This is my friend May.”
“Nice to meet you.  Cynthia’s in her office.”  She pointed.  “Follow the wall and you can’t miss her.”

May led the way, taking her time and taking in the racks of latex outfits, catsuits, dresses, all sorts of things, with great interest.  They spotted Cynthia sitting at her desk in a utilitarian alcove lined with grey filing cabinets and swatches of latex.  She jumped up when she saw them.
“Bobby!  You made it.  And you must be May.  Nice to meet you.”
“And you, Cynthia.  I’ve heard a lot about you.”
“Good or bad?  Never mind, I don’t care.  Now, Bobby, I understand from May here that you and your colleague Tim are interested in finding you a dress.  Right?”
“Well, yes
  But I thought it was still in the design stage
”
“Oh, it is.  I should say, they are
  But we have so much stock, I’m sure I can find you something for now.  Blue satin, is it?”
“Er
yes
”
“Your choice, or
”
“Tim’s,” grinned May.  “He thinks Bobby’ll look nice in blue satin and white tights.  I think he’s probably right.”
“Me too, Bobby – though you’d look good in anything.  But I’ll tell you what we’re going to do.  As a surprise for Tim, we find you the clothes, yes, but we’ll also give you a complete makeover.  So when you go back to the Centre, you can give him the surprise of his life
”
“Really?”
“Oh yes.  You wait.  I’m as excited as you are.  You’re going to make such a pretty girl.  May?  We’re going to need your advice.  Let’s go into the back and finds the outfit first, then I’ll introduce you to Trish.  She’ll take care of everything else
”

[Simonssister]

Chapter 250.

It took Cynthia less than ten minutes to find a plain blue satin dress which fitted.  The matching panties, tights and shoes were no problem.  May rather coyly mentioned the pink latex panties.
“Oh, naturally he should have some latex,” smiled Cynthia.  I’ll find some him very fine light ones he can wear under the satin ones – okay?”
“Perfect, thank you, Cynthia.  Tim could hardly ask for more.”
“We’ll give him a padded training bra.  He’s coming on, but I guess it’ll be a while yet.  I’ll box up a handbag and some little spandex gloves as well, in case he goes out somewhere posh.  Now, come with me and let’s see what Trish has in mind.”
Trish turned out to be a rather cool-looking young lady with short dyed blonde hair, multiple ear-piercings, dressed in torn jeans and a black vest, and with tattoos of Japanese warriors on both arms.  She looked at Bobby critically.
“Blue satin party dress, puff sleeves, white tights,” said Cynthia, matter-of-factly.
“Traditional,” said Trish.  “Cute.  I get it.”  In that case I’d suggest a tint.  Blonde and blue – too predictable.  Maybe some extensions?  Pale eye shadow, subtle makeup.  I’ll need to see the dress.”
“I’ll have it sent in.”
“Okay.  Let’s go, mate.”
“Can I watch?” asked May.
“Please yourself.”
“Do you mind, Bobby?”
“No.  I’d feel better if you were there.”
So she followed Trish and Bobby through a back door, leaving Cynthia smiling after them. 

The makeover took over an hour.  First Trish found a pair of light brown extensions which she said would suit him, they washed and tinted his hair to match.  She dried his hair and attached the extensions, shaping and pinning and texturizing so his real hair and the extensions looked as one.
“I’m using clip-ins, which I wouldn’t normally do, but I understand he may need to take them off for work.  They’ll still look good, don’t worry.”
She finished with mousse and a big blue ribbon that went perfectly with the party-style of the dress.  Then she did his nails with a pale blue translucent polish, and did his makeup – subtle eye-shadow, mascara and lip-gloss.  She gave him a spray of scent, and he was done.  She gave May a bottle of the same scent.
“Here – pop this in his handbag.  Cynthia’s already put in a little makeup set and a couple of bangles, I see.”
May couldn’t take her eyes off him.  To all intents and purposes, he was a girl.  The tension between his appearance, and the knowledge he was actually a boy, affected her quite profoundly.  She felt a physical pain, in her chest, a sort of yearning – but for what, or why, she couldn’t say. 

They left hand in hand.  As she drove, she kept taking peeps at the happy person sitting next to her. He was ecstatic.  The satin dress was so light and crisp, the feeling of his shiny nails and glossy lips so exciting, he couldn’t stop talking, eulogising about Fantastex, and speculating about what other dresses may be in the pipeline.  He looked so pretty, May considered pulling off into a lay-by and snogging him.  But she didn’t want to muss his perfect makeover, so she resisted the temptation.  “Later,” she thought.  Since Tim would still be working, she stopped at a cafĂ© a couple of miles from the Centre, and they sat there chatting for some time.  The only people that noticed them were a few young guys – who all seemed more interested in Bobby than in her.  “If only they knew,” she thought, with a smile.  “Tim’s gonna have a heart attack!”

When they finally got back to Pitt’s Wood, she took him down the back of the new stable block, so no-one would see them.  Before they went in, she took one photo of him posing outside the boot parlour, beaming with delight.  It was her favourite snap of all time

 

[RibbonBound]

I just wanted to take a moment to sincerely thank you for your incredible story. It’s clear how much heart and effort went into your work, and I’m truly grateful you chose to share it.

The situation with Timmy being teased by the idea of Bobby in a dress, chapter 243, was one of the hottest things I've ever read.  All the details about the outfits, like the little crotch loops and plugs and their effect on the boys is incredible.  Your creativity with the outfits is just mind-bending!  But where you're taking the story now, with Bobby in his little blue dress...

I’m already looking forward to whatever you write next.

[Simonssister]

Thanks, RibbonBound - that means a lot.  I hope future developments prove equally interesting!

[Simonssister]

Chapter 251.

Things had been going so well in the boot parlour, but there were a couple of setbacks looming.  The worst thing was that Miss Poole had received a phone call from Deborah’s groom explaining the wedding had been put back three weeks, owing to the bride’s mother, who lived in New Zealand, being ill.  She hadn’t told the boys yet, but she knew they were all hyped up for the 8th, and now they would have to wait till the 29th.  Well, it couldn’t be helped.  Then there was the MĂ©lisande issue.  Clarissa had called in a couple of days ago.
“Sorry to arrive unannounced, Violet, but I wanted q quick word about Bobby.”
“Any time, Clarissa.  Is there a problem?”
“Well, not with Bobby.  But Mellie’s pestering me all the time.  She hasn’t been able to ride him since the dressage event – that’s two whole weeks now.  A couple of times she’s come to the Centre hoping to see him, but he’s either working or with that girl May.  She’s getting quite frustrated.”
“Oh, poor thing.  Yes, I understand.”
“And she mentioned that you had promised she and her friends could organise some pony rides with him as the pony.  She was wondering if that was still on offer
”
“Oh, dear.  It’s true, I did say that.  It’s just that he’s been so busy.  Demand for the boys’ services has been so much greater than any of us imagined.  It’s a roaring success, and over the winter I think it can only get busier
”
“I see
”
“However
  I’ve just been told that the wedding next weekend has been postponed.  We’ve made no bookings, so why don’t I release Bobby for the whole weekend?  Tim can go solo.  Then MĂ©lisande can have him to ride all Saturday, and maybe they could do the pony rides on Sunday.”
“Really?  She’d be ecstatic.”
“I’ll let him know.  He’ll be disappointed about the wedding, of course, but maybe this can make up for it.  I’m sure he’s dying to get back in his pony suit.”
“I hope so.  It’ll be hard work, I guess, on the Sunday
”
“Yes
  In fact
  Don’t say anything about this, will you?  In fact I’ve been considering ponifying Timmy as well.  He’s bigger than Bobby, so he could carry the heavier ones.”  She sniggered.  “I know some of the stable girls would love to get on his back
”
And they giggled like a couple of schoolgirls.

Miss Poole was also being pestered - by Serena, who wanted either another long session or a private booking at her home.  But the boys had been booked up solid, and though Serena had Tim’s phone number, she knew she might get banned if she called him direct.  After Clarissa had left, it occurred to her the wedding postponement could be used to kill two birds with one stone.  So she got straight on the phone.
“Serena dear, it’s Violet Poole.”
“Oh!  Hello, Miss Poole.”
“I’ve got good news and bad news.  We’ve had a change of plan for next weekend.  The wedding I told you about is off.  The bad news is that Bobby’s otherwise engaged the whole weekend.  The good news is that Timmy’s free the whole weekend.  I don’t know what your plans are
”
“The whole weekend?”
“Well, yes
”
“Then that's a booking.  What time can I collect him?”
“Well, er
  You want him both days
?”
“Absolutely.”
“Well, great
  That takes care of both of them.  I’ll tell Ellie to have him ready at nine Saturday, and you should return him Sunday evening.”
“Thank you, Miss Poole.  I’ve really been missing them.  I can make up for lost time now.”
“I see
  Is there anything else?”
“If Ellie could pack spare outfits
and accessories
”
“I understand.  It shall be done.  I’ll ask Evelina to make the booking.  Excellent.  Thank you, Serena.  I hope you have an enjoyable weekend
”

[Simonssister]

Chapter 252.

Ever since the boys had first appeared in their pageboy outfits, the community of stable girls had been buzzing with excitement.  Nicole had had an idea that MĂ©lisande and her friends might like to form a fan club, but the stable girls got there first.  Some of them had got their hands on a packet of the special “Bobby Boot Boy” woven badges Cynthia had produced, but soon others had obtained a rival product consisting of a red heart with the letters “TFC” – Timmy’s Fan Club – embroidered in the middle.  Many wore both side by side.  The strategy behind these expressions of adulation was simple – to convince the boys that in the new outfits they were god’s gift to women, and to ensure they never doubted their own sex-appeal.  They had become pageboy idols!  Moreover the girls always made sure to stare when they appeared in the Centre, and bestow gasps of admiration and yearning.  For Bobby this was merely pleasing, if slightly embarrassing, but for Tim it was confirmation of his celebrity status, and he took every opportunity that presented itself to swagger about the stables like some sort of male model, showing off his little glossy shorts – and their contents - and telling everyone how exclusive their outfits were.

But whilst they were entertained, the girls were also a little bit jealous.  Pageboys?  What about pagegirls?  These outfits were too cute to be restricted to males.  Why couldn’t they get some for themselves?  First off it would be a great way of putting Tim in his place.  But quite aside from that, the whole pageboy-pagegirl look was undeniably sexy.  So soon afterwards a dozen or so of them had held an impromptu meeting in one of the stables.
“God, I’d love to turn up in front of my boyfriend wearing something like that,” remarked Candy.  “I reckon his eyes would just about fall out.”
Candy was actually Diana Murchison’s niece.  She was a year older than the boys, but with her dark hair in pigtails and her naughty eyes she looked like a character out of St. Trinian’s.  She had received an evasive and totally fictitious account of her aunt’s and Eleanor’s most recent visit to the boot parlour, which had annoyed her.  “I’m not a kid, auntie,” she had complained.  “I’ve heard rumours
”  But she got nowhere. 
“Yeah, I bet,” May replied.  “The thing is, when the boys wear them they look awfully sissy – though they don’t realise it – but on girls they’d be sexy and powerful.  You know how blokes are when confronted with a woman in latex.  They get all nervous and sheepish.  Did you see the stable lads when Serena turned up in her latex catsuit that day?  They couldn’t stop staring at her but when she asked Reggie – you know, the macho one – to saddle Porter, he nearly wet himself!”
“I remember!” laughed Jessica.  “Mind you, she was carrying that special dressage whip of hers.  Ellie?  Can you ask Cynthia about this?  I bet the shorts are expensive – and we’d need boots too, to complete the outfit.”
“I can
  But I think you’d be talking about a hundred plus if they were made-to measure.  It’s possible she has some off the peg, which would be much cheaper.”
“First of all we should focus on pranking the boys,” said May.  “Choose a couple of willing girls, buy them outfits, and send them for a session.  I’d love to see the reaction.”
“Confusion, most likely,” laughed Deborah.  “What do you think, Jasmine?”
Jasmine was Ellie’s closest friend, and always received updates on what was going on in the boot parlour.
“What do I think?  First of all, I think we ought to isolate Tim.  He relies on Bobby so much for moral support.  By himself he’s a bit of a wimp.  And such an awful show-off!  And the way he swaggers around in front of the younger girls, like he’s some sort of film star!  He needs taking down a peg or two.”
“I agree,” said Ellie.  “Of course, I’ve got those videos of him and Bobby, but they’re wearing masks, and in any case I wouldn’t compromise Bobby.  Yes, we need something on him alone
”
“Can we organise that, Ellie?” asked Valerie.
“No problem.  I’ll find an opportunity.  Bobby has to go to Cynthia’s about his dress soon.”
“Good.  Then if we can get two outfits we can book a nice long session with Tim all by himself!”
“I could go,” said Candy.  “I know my aunt would pay for the outfit as well.  For two if I asked nicely.”
“Would she?  That’d be great,” said Jasmine.  “Who’d be good to send with you?”
“I could take Phillipa
”
“The new girl?”
“Yeah.  I know her from school.  She looks innocent, but she was always up to mischief, always playing tricks on the teachers, but so studious and serious in class they never realised she was the perpetrator.  We can both wear TFC badges too – he’ll love that!”
“She sounds perfect,” laughed Ellie.  “She’s cute, too.  I’ve got to see Cynthia later this week.  Why don’t I ask her about it, and if she can help I’ll take the pair of you with me
?”
“Great!”
“Wednesday okay?”
“Fine.”
“But what would they do?” asked Colette.  “I mean, we need some sort of plan.  Just getting a boot service isn’t gonna cut it, is it?”
“Oh, don’t you worry, Collette,” grinned Ellie.  “You have no idea what I’ve got tucked away in the locked cupboards in the boot parlour.  I’ve already got several ideas that are going to make your hair stand on end – as long as Candy’s up for it?  Are you, sweetie?”
“I’m up for anything, Ellie – the naughtier the better!”