His Aunt Nicole

[Simonssister]

Chapter 346.

When he finally made it to the canteen he found Bobby waiting for him.
“Where’ve you been, Tim?  I’ve been here for nearly twenty minutes.  And what are you wearing?  Everyone’s staring…”
“I know.  Amazing isn’t it?  I’m sorry – I just went for a walk around the Centre, and I got stopped by so many people – girls, that is – that I quite lost track of time.  I’ve had girls following me about all the morning.  How are you, anyway?”
“I’m fine.  Worked off my feet, though.  They’re talking about an apprentice.  When are you coming back?”
“Not sure…  It’s all up to ESDS.  You’d need to ask Miss Poole…”
Bobby looked at him and frowned slightly.
“You’re different…  You look so confident, somehow.  And you speak properly.  Not that you didn’t, I mean, but…”
“I know.  It’s all the training.  It’s been really hard…”
“It must have been.  So you’re a maid now?  Then why…?”  He pointed at Tim’s outfit.
“I’m a pageboy most of the time – thank goodness.  My first real posting starts Saturday.  I was the pageboy at a wedding…”
“Oh, I’ve seen the pictures, don’t worry.  Didn’t you mind?  You looked so cheerful…”
“Course I was.  It was a very important job.  Everyone loved me.”
“Yeah, right.  They all smiled and laughed, right?”
“Yeah, all the time.  I’m telling you, Bobby, I was a big hit.”
“I could see why – in those little purple latex hotpants…”
“Actually they’re not hotpants, Bobby,” retorted Tim, slightly irritated.  “They’re proper pageboy shorts, and…”
“Whatever.  Look, I’ve got to get back.  I’m only allowed forty minutes for lunch these days.  See you round, pageboy.”
“Oh…  Yeah, see you…”
But Bobby was already gone.

“Tim?”
It was Serena.
“Hi.”
“Shall we make a start, then?”
“Sure.  What’s next?  I really like this outfit.  But maybe tomorrow I could have a white top?  And a jacket of some sort?”
“Sure.  We can arrange that.  Now, this afternoon.  We have some lovely outfits for you.  Some of them were designed by Mrs Brookshaw, too.  I just hope everything fits.”
“Well, everything fitted this morning…”
“Yes, but dresses are different.”
Tim stopped dead.
“Dresses?”
“Dresses.  Of course.  You surely didn’t imagine…  Silly boy.  You can’t be a pageboy all the time, you know.”
“But…”
“I know Robyn asked her aunt to take at least the yellow shorts.  Not sure what else.  But the dresses are cute!  Wait till you see them.”

Doreen sat him down and did his makeup.  The mascara tickled.  She even combed some tint into his hair. 
“There.  You look really pretty.  Hold still while I do your lip gloss.  Pout.  Again. Good,  Press together.  Soon you’ll be doing this for yourself…”
His first outfit was worse than he could have imagined.  A pink and white creation in vinyl and fabric with white stockings.  Not only that, but a lace choker underneath a locking pink leather collar, as if he were some sort of slave, and matching arm and wrist cuffs!  He stood helplessly in the stable while Doreen and Lucille dressed him and locked the collar.
“What’s all this about?” he wailed.  “Cuffs and a collar with a padlock?  Is this woman some sort of pervert or something?”
Lucille laughed.  “It’s just a look, that’s all.  Mind you, I wouldn’t cross any lines if I were you.  Mrs Brookshaw does have a reputation as a bit of a disciplinarian…”
As they ushered him out of the stable he saw two faces he recognised.  It was Josephine and Yvette from the wedding.
“No…  Don’t let them see me…”
But it was too late.  They were waving and calling his name.
“Shit…”

He put on a brave face.  They didn’t make fun of him.  They complimented him on his transformation.
“Tess and Frankie are on their way, Tim.  Don’t change till they get here, will you?”
Then came the photos.  There were even more of those pesky little girls hanging around now.  It was getting embarrassing, especially as he was continually being told to pose like a girl.  When he was a pageboy he welcomed all the attention.  But now…

Tess and Frankie loved him.  They couldn’t stop staring, and taking endless photos.
“When we heard about the shoot we just had to come and watch!  You look even more amazing that at the wedding.”
“Mitzy!  Next dress, please!” called Lucille.
“Mitzy?  Is that you?”
Tim sighed.  “Only when I’m a maid…”
“Mitzy!  That’s such a cute name!”
“Mitzy!  Come on!”

[Simonssister]

Chapter 347.

Tim’s day, which had been so fun in the morning, was turning into a nightmare.  As he entered the stable, he saw that underneath the box that was being unpacked were two more!
“How many dresses are there…?”
“Oh, not many,” said Doreen, calmly.  But we need to get through them all this afternoon, so let’s get a move on.  Turn round and let me unzip you…  The next one’s very plain and simple, so I'll need to clean off all that makeup.  It's not appropriate for a little girl.”
“Little girl?  What do you mean?”
“You'll see.  Sit down and pass me the wipes.  Thank you.”

Serena was outside on her phone talking to Connie Brookshaw in a low voice.
“We’re in the new stable complex.  You can’t miss us  - we’re being followed everywhere this afternoon.  Sorry?  Grumpy, I would say.  Yes, he’s not happy at all.  Dresses aren’t really his thing.  I know…hilarious.  I’d better go, anyway.  Half an hour?  Right.  I’ll have him in one of yours.  No, he has no idea.  Just mingle with the fans…”

Serena stayed outside enjoying the air till they reappeared.  Tim was frowning.  Well, not surprising.  He did look an idiot in that little red juvenile outfit.  Of course, once he was up on his dais he did his best to laugh it off.  As usual had an audience, and he didn’t want them to see her wasn't doing all this of his own free will.
“What sort of dress do you call that?” asked a blonde girl, cheekily.
“It’s just a work dress, that’s all…” improvised Tim.
“Looks more like a little girl’s activity outfit,” remarked her curly-haired friend, suppressing a laugh. 
“What’s with the hair-bow?” persisted the other.
“Leave me alone, would you?  I’m modelling all sorts of things today.  Did you see my black leather…”
“Yes, we did!” cried curly.  “So sexy!”
And they burst out laughing.
“Just go away!  Miss, tell them to go away…”
“Sorry, Mitzy.  They have more right than we do to be here.”
“Yes, Mitzy.  We have more right to be here than a silly boy in a little girl’s smock…” said blonde.
“Made of rubber, by the look of it,” added curly,  “and…”
“Hey, Paula!  Come round here!  You can see his panties!”
“Ooh…”

And so it went on.  Eventually they escaped those two particular little horrors by moving into the indoor school.  There were just three riders there, and they were a bit older, so potentially not as annoying.
“Miss, I hate this outfit.  If I have to wear a dress, can it at least be glamorous?  This is like a kid’s dress.  I feel totally stupid.”
“Okay, Tim.  I’ll tell you a secret, shall I?” said Lucille, whispering.
“What?” he replied, sulkily.  But his face said he was interested.
“I wasn’t supposed to tell you, actually.  Mrs Brookshaw ordered this one from the Fantastex catalogue herself.  For a grown boy, she said it was the most embarrassing one she could find.  She also said…”  She lowered her voice.  “She also said, if you were prepared to wear this without complaint, in fact to swagger about in it just as you do in your pageboy shorts, she’d let you wear your shorts for the whole weekend instead of the maid’s outfit she had planned.”
“Really?  Even for her party Saturday night?”
“Even for that.”
“Okay!  Listen, can I still do it, then?  I was being silly.  I apologise, I really do…”
“Well, I suppose…  But you mustn’t tell anyone I told you.”
“I promise!”
“Okay…  Well, let’s have some piccies by the side of the arena, shall we.  Nice poses, mind.  I don’t think those girls will bother you.  Then we’ll have a little parade around the Centre, let all the others get some pretty snaps.  Then we can move on to the more sophisticated styles…”
“Okay.  No probs, Miss Lucille…”
“Good boy!  Here.  I've found another Alice band that matches your dress better...”

Lucille turned to the others and winked.
“Did Mrs Brookshaw really say that?” Doreen asked Serena.
Serena laughed.  “No,” she whispered.  “She wants him in his shorts the whole weekend anyway.  Thinks her guests would prefer it.  And Robyn, of course.  Anyway she’ll be here any minute.  With luck she’ll get to see just what a sweet, obedient little boy Tim is!”

[Simonssister]

Chapter 348.

Serena took him the long route back to the changing stable.  Most of the way, despite the pointing and suppressed laughter from those he passed, the walk wasn’t too challenging.  Until he turned a corner and ran straight into the junior showjumping team, on their way to saddle their horses.  After the initial gasps of surprise, they surrounded him, bombarding him with questions.
“You’re Tim, aren’t you?  I saw a video of you being a pageboy!  Why are you wearing a little girl’s dress?  Where are you going?”
One grabbed his skirt from behind.
“It’s rubber!  Look…  It’s all stretchy!  Why is your dress made of rubber?  Are you going to wear it for cleaning boots?”
“If you are, I’m booking a session!”
“Me too!”
“And me!”
Serena stood back and let them get on with it.  Tim glared at her.  Standing there killing herself with laughter.  He made to walk away, but the girls weren’t having any of it.
“Tim, can I take a picture?”
“Looks like you already are…”
“You don’t mind, do you.  You look so cute…”
Foolishly, he tried to explain. 
“Look, we have a very important photo shoot today…”
(Excitedly)  “Are you going to wear your pageboy outfit?”
“I’m afraid he posed in that this morning.  I’m sorry you missed it,” put in Serena, walking up and taking Tim by the shoulders, to prevent him running off.
A chorus of disappointed ohs…
“But he’ll be modelling dresses all afternoon.  We’ll be by the new stables.  Come and watch if you can.  Anyway, I can give you some piccies from this morning if you like…”
“Miss!  No…”
“Yes please, miss.  Thank you, miss!”
Serena obligingly transferred a string of the best images to one of the girls.  Once she had them, the others crowded around, and Tim was temporarily ignored. 
“Right.  Shall we go, Tim?”
“Why did you do that?”
“Well it worked, didn’t it?”
“Bye Tim!”
“Bye, Tim…  See you later…”

Tim sighed.  He hurried back, Serena following.  On the way he passed a woman in riding breeches who looked at him as though she knew him.  But he certainly didn’t know her.  If he had turned around a second later, he would have seen her exchange glances with Serena.  Connie Brookshaw had arrived. 

Back in the stable, Lucille was unpacking a pretty yellow dress.  Doreen tied a protective plastic bib around his neck, sat him down, and began to work on his makeup.
“You need to look your best for this one.  Look at that dress!  You’re a lucky boy, Tim.”
Tim looked at it and felt sick.  Yellow latex with matching panties and crinolines.  White stockings with yellow bows!  Ugh.  But anything was better than what he was wearing.  He shook his head.  Now those pictures of him would be all over Pitt’s Wood.  What would Jessica think?  It had been a while since he had seen her, and now he didn’t particularly want to run into her and have to explain everything.  And Ellie.  Oh, she’d have a good laugh, she would!  His face burned with embarrassment.

Doreen did a great job.  Then he was finally allowed to get out of his juvenile attire and put on the dress.  Then the walk back up to the new stables, for which he was at least allowed to wear his trainers.  Then putting on his heels, being helped up onto the wooden platform, and standing there wobbling while another group of giggling girl riders looked on gleefully, revelling in his obvious discomfort.  Lucille, clearly enjoying every minute as well, had decided that the presence of one or two of the better turned-out riders enhanced the authenticity of her photos.  On this occasion she encouraged them to stand close by, and apparently had no problem with them asking him stupid questions.
“Hi.  What does it feel like…”
“…for a boy…wearing such a pretty dress…?”
“Do you have girl panties underneath?  Do you?”
“Yes, he does actually.  Tell them, Tim.  Go on.”
“Y-yes…  I…”
“As a matter of fact…”
Tim looked at Lucille, alarmed.
“…he has pretty yellow latex ones to match his dress…  Don’t you, darling?”
The girls gasped in disbelief - then collapsed with mirth.  How could she be so cruel?  But she, and the other two, had decided that if they had to work all day, they were going to have some fun at his expense.  And it was not over yet.

[Simonssister]

Chapter 349.

As they returned to the stable, Tim was in a huff.
“Stupid brats,” he muttered.
“What, those two nice girls?” asked Lucille, tongue in cheek.
“Nice?  Asking all those silly questions…”
“We thought they were rather fun.  There was some sort of chemistry going on between the three of you…”
“Yeah…  I was thinking about poisoning them…”
“So I asked them to hang around for the next session.”
“What?”
Serena snorted with laughter.
“Miss…that’s not fair…come on…”
“But this one’s so pretty…my favourite actually.  You’re going to look amazing…”

It was a beautiful dress.  Even Tim realised that.  When he clocked himself in the full-length he did a double-take.  If he had met a girl looking like he did, he might well have fallen for her on the spot.  The conflicting emotions of embarrassment and excitement were tying him in knots.
“So what do you think?” asked Doreen, watching his confused expression with interest.
“I…  You know…  It’s a dress, isn’t it…”
His voice trailed off, but he couldn’t take his eyes of himself.  Beautiful white latex with pink flowers, not glossy but with a seductive sheen, like the finest satin.  Crinolines, a white ruff collar, white stockings with pink bows.  The dress fitted to perfection – more, it seemed to shape his body into female lines.  He touched the latex.  How did they even make this?  It must be fearfully expensive.  And it was made specifically for him.  They must think he was worth it.  He experienced a little shiver of pride and excitement – and, it must be said, a slight pressure in the little soft latex panties hidden away under the mass of crinolines.  He gulped, and took a few deep breaths.  Momentarily he understood completely how Bobby must feel in his dresses.  Suddenly his cheeks were burning.  Quickly he turned away.
Doreen was looking at him with a little smile.  Was she reading his mind?
“See?  You have to admit you look quite something.  Now sit down here and let me touch up your face.”

Five minutes later he was on his rostrum.  The two brats had waited, but he could see that their mirth was tempered with admiration.  Lucille let them feel the material.
“Gosh, miss, that must have cost a fortune!  I wish I could afford a dress like that…” said the ginger-haired girl.
Her friend turned to her, laughing.
“Caroline, what are you saying?  You’d never wear anything like that.  You refused all those dresses you mum got you.  You hate dresses!”  She turned to Lucille.  “She only dresses up for riding.  Otherwise it’s jeans and T-shirts.  She doesn’t even dress up when we go clubbing.”
“No, but Faith – remember I went through like a goth period…  I liked dresses then…”
“Yeah, but your mum didn’t let you wear goth dresses, did she?”
“I’m older now…  What I meant is…  I mean, this is latex!  Latex is cool.”
“Black latex…”
“No, black latex is yesterday.  It’s been so overdone.  Imagine white latex, like this.  Sort of innocence and sex fused together…”  Her eyes shone.
“I think Caroline’s got a point,” said Serena.  “Caroline, let me have your number.  When I have a moment, I’ll see if our supplier has anything off the peg you might like…”
“Wow, would you?  Thank you so much…”

The photo-session proceeded.  Whether it was the dress, or Tim’s ill-disguised impatience, but this session seemed to have attracted a bigger crowd.  And at the back Tim caught sight of that woman he had passed earlier, again looking at him with a sort of proprietorial smirk.  That should have been a clue.  They were about to return, when the woman in question approached.
“I wonder…  That’s such a beautiful dress…  Do you think I might get a few snaps for myself somewhere slightly less busy?  So many girls – and horses!”
Serena stepped forward.
“Of course, madam.  We can do that.”  She gave Mrs Brookshaw a secret wink.  “Let’s move to the passage between the stables over there.”
And so Connie Brookshaw had a photo-session all of her own.  Which was only fair, given that she had designed the dress…