Chapter 345.

The leather hotpants fitted him perfectly.  They also suited him perfectly.  It was definitely his favourite outfit of the day.  They did the shoot in one of the new stable blocks that had recently been built on the very western edge of the Centre, where there were fewer riders, and a background of open fields.  He was posing standing on a crate, when one of the stable girls approached.  She had just finished saddling horses for two members, and took a few minutes off her duties to complement him on his outfit.
“Hello.  Are you Tim?”
“Yes.”
“Hi.  I’m Jenny.  I work here.  You cleaned my boots a few weeks ago.  Actually twice.  Do you remember?”
“Oh…  I think I do, but I cleaned so many girls’ boots…”
“I know.  Then you were wearing really smart little red pants.”
“Oh…  Was I…?”
“Yes.  But I think I like these hotpants much better.  They look really good on you.”
“Do they?  They’re not hotpants, actually…”
“They surely are.  They have the braces and everything.  They’re proper hotpants.  You look great.”
“Er…  Thank you.”
“I’m Jenny.”
“Hi Jenny…”
“I have to get back to work now, but…”
“Yeah?”
“Can I ask you something?”
“Sure…”
“Would you go on a date with me?”
“What?”
“Would you go on a date?  My friend wants me to go with her and her boyfriend, but I don’t have a boyfriend.  Would you?  Please?  I think you’re so great.  I thought so the first time I met you.”
“Go on, Tim.  Go with Jenny.  She’s asked you so nicely,” interjected Lucille, delighted.
“But I…  I mean, I don’t know if I’ll be free…  I have work, see…”
“When is it, Jenny?” asked Serena.
“Tomorrow.  Tomorrow evening.”
“Perfect.  You’re free tomorrow evening, Tim.  You don’t go to Mrs Brookshaw’s till Saturday morning.  Yes, Jenny, he can go.  You’ll go with Jenny, won’t you, Tim?”
“I…I…”  Serena gave him a look.  “I guess…”
“Good.  That’s settled then.  Can he meet you at reception, Jenny?”
“Yes!  Great!  Thank you so much!”
“What time?”
“Five-thirty?”
“I’ll drop him off.”
“Tim?  Can you wear…”  She pointed at his hotpants.
“Tim?  You’ll wear your hotpants for Jenny, won’t you?”
“I…”
“My friends will be so jealous…  You’re so amazing…  They all worship you…”
“They do…?”
That did it for Tim.
“Course.  Glad to help.”
This was definitely the coolest outfit of the day so far.  He had, like, completely dazzled this girl, just by being himself.  Yeah, well it was true, all the girls in the Centre were really stuck on him.  He knew that.  Bobby?  Well, Bobby wore dresses!  They would hardly…  Anyway, yeah, he should circulate a bit more.  Like at the wedding.  When he did, he was so popular.  He’d been so busy training, but in future…
“See you tomorrow, Tim!” called Jenny, hurrying off and giving him a little wave.  Prob’ly gonna tell all her friends…
“Good for you, Tim,” said Doreen.  “I’m sure you’ll have a great time.”
“When we’re finished…  Can I wear this outfit through lunch, miss?”
“I can’t see why not…”
“Thanks!”
Great!  He wanted to stroll around the Centre and show it off a bit before he went to the canteen.  So few girls around up there in that remote stable block.

He did, too.  He found that the girls stared everywhere he went.  Many of them smiled and waved.  A few called his name.  Occasionally one would just stare, open-mouthed.  Struck dumb.  Rendered speechless by pure cool.  The hippest guy in town…   

Chapter 343. 

Robyn made her way to the canteen, where her mother was drinking coffee.
“Did you see him?”
“Oh my god, mum.  Make him wear those little yellow hotpants on Saturday, please…  Give him some kitchen duties.   Just for me, yeah?”
“Oh, yellow ones now?  Okay.  I’d like to see that myself.”
“They’re so pretty!  And he’s so proud of them!  I couldn’t help laughing.  Look at this.”
She handed her the phone.
“Well, well…  He’s a treasure, for sure…”
“Look, I have to go.  I’ll come back and pick you up at five, yeah?  Take as many snaps as you can, won’t you?”
“Don’t worry, dear…”

The rest of the morning was dedicated to boy stuff.  There was a fun traditional pageboy outfit with knee-breeches and silk stockings in pale blue, and a pink roller-boy costume.  By this time Pitt’s Wood was filling up, and there was no shortage of spectators.  It soon became impossible to keep them out of the photos, so the ladies simply accepted their presence and pressed on regardless.  As for Tim, he was happiest when playing to an audience, and welcomed all the extra attention.  The titters, giggles and whistles that accompanied the applause every time he appeared in a new outfit he interpreted as a symptom of suppressed admiration.  Lucille remarked to the others that they could really be even more daring in their choices.
“Well, we do have the “sissy pageboy outfit”,” grinned Serena.
“Would he accept that, though,” asked Doreen, doubtfully.
“Let’s try the other vinyl outfit first, then.  I have a feeling he’s up for anything today…”
“He’ll need to be this afternoon.  You’ve got the makeup case, Doreen?” asked Lucille.
Doreen smiled and nodded towards the pile of boxes marked “P.M.”

Chapter 341.

Despite his anxiety about what sort of person Mrs Brookshaw was, and what demands she would make of him, he slept well that night and was up early Thursday morning.  It was the beginning of December, but fortunately the weather was bright and sunny, and though there was a bite in the air, there was little wind.  He showered, put on his red hot pants pageboy outfit, and presented himself in the breakfast room.  Several of the staff were sitting at the big table.  Cassandra was relaxing in an armchair, sipping coffee.
“Good boy!” she smiled.  “All ready to go, I see.  What would you like for breakfast?”

He opted for cereal and pancakes.  Eating reminded him of lunch.
“Miss?  Will I be taking a packed lunch?”
“Oh, no…  Too much fuss.  We’ll go to the canteen.  You can have whatever you want.  With a bit of luck…”
“Will I see Bobby?”
“That’s what I was going to say.  If we can, we’ll organise it so you’ll be able to see your friend.”
“Great!”
“Oh, and this is for you.  Doreen got it for you.”  She handed him a little pink belt-purse.  “You can keep your money safe, or a tissue.  She put your gloves in there too.”
“Ooh, thanks…”
“Doreen and Lucille will be doing the photography.  Lucille?”
Lucille was sitting opposite him.
“We may ask you to pose, but otherwise you can just be natural.  Anyway, Serena will be in charge of the locations, so just do what she tells you.  There’ll be people you know there, and we’ll have plenty of time.  Also, I’m sure our little shoot will attract an audience.  Other people might be snapping away, but just ignore them, okay?”
“Sure.  Of course.”  He couldn’t suppress a smile of satisfaction.  “So will I have many new outfits?”
“Well, several, I think,” said Cassandra.  “Most of the pageboy things may be just variations of the original.  But don’t be disappointed.  We have to give our clients a choice of styles and colours, naturally.  Then some will want one outfit for when you’re working around the house, another for parties, another for going out, and so on.  Miss Brookshaw was primarily thinking of you as her maid, but when I showed her a photo of you as a pageboy she was so impressed, and amazed at your versatility.”
“I think I prefer being a pageboy…”
Cassandra laughed.  “I’d noticed.  You love those swanky shorts, don’t you?”
Tim grinned.  Yes, He rather be a pageboy any day than dressed as a girl.  The female attention was addictive.
“Well he does look so cool in them,” remarked Lucille, with a romantic sigh.  “Such a heartthrob!”
Tim liked that.  He bestowed on her what he imagined was a devastating smile.  He simply couldn’t help being such a babe magnet…
“Well thank goodness it’s a nice day,” smiled Cassandra, looking out of the window.  “Mild too, for the time of year.”  She looked at her watch.  “You guys should get going soon.  Let me know how things go, won’t you?”
“Yes, mum,” said Serena.  She exchanged glances with Cassandra.  What they weren’t telling him was that Connie Brookshaw was going to pay them a visit, probably sometime in the afternoon, when he would be modelling a couple of her creations.  He’d never met her, nor seen a picture, so she would pose as a horsey visitor.  But she wanted to see her new maid in the flesh.

To Tim’s disappointment, Serena wasn’t taking the Porsche.  Instead the four of them were going in Lucille’s estate, into which the various outfits and props had already been loaded. 
“Oh, sorry Tim,” said Serena, with mock sympathy, “I know you love my car…”
“Work hard and you might have one of your own one day,” remarked Doreen.
“No, I just like this one,” said Tim, sadly.
“Okay – pretend it is yours,” laughed Lucille.  “Go on – I’ll take a quick snap.”

It was a quick drive – there wasn’t much on the road that morning – and by eight they were in reception.  Miss Poole came out to greet them.
“You’re here nice and early.  It’s a lovely day for it.  Tim, you look so smart today.  Love the new red shorts.  Are you looking forward to it?”
Tim nodded enthusiastically.
“He’s in his element,” said Serena, with a wink.  “Aren’t you, Master Painter?”
Tim looked puzzled, and everyone laughed.
“Ah, yes,” quipped Miss Poole.  “The TFC’s going to be out in force today…”
“TFC…?” repeated Doreen.
“The Tim Fan Club, dear.  Really, you should make it official.  Would you like that, Tim?”
He looked startled.  “My own fan club?  Really…?”
Everyone laughed again.
“I think Miss Poole was joking, Tim,” said Lucille.
“Was I?  I’m not sure.  You realise, Tim, that since the wedding your image is all over social media?  Why doesn’t one of you ladies work with his Facebook profile, or get him on TikTok or something, so he can show off all his outfits more widely?  I’m surprised you hadn’t thought of it.  Would you like that, Tim?  Yes, of course you would.  I’ll talk to Cassandra.  We could link it to ESDS.  It would be good for Tim and good for us.”
“It’s an idea…” said Serena, thoughtfully.
“Anyway, you should get on.  Where are you going to start?”
“We thought around the new stables, said Serena.  We’ll head up there and take a couple of test photos to see what they look like.”

Ten minutes later Tim, watched closely by a couple of girls who had come to saddle their ponies, but had been distracted by his appearance, was posing in one of the upper paddocks, one foot on a mounting block, looking like some sort of pioneer.  To tell the truth, had he worn that one outfit all day he would have attracted all the attention he could have wished for.  But there were plenty of others in the back of Lucille’s car…   

i very much enjoy this story (and your other stories).  The slow acceptance of the soft comforts and pretty delights of being treated as a baby girl …. sigh!

Chapter 3

Andy felt a chill run through his body and it triggered an involuntary spurt of urine to further soak his nappies. Olivia smiled at him like a doting mother. “That’s a good baby, you will soon get used to wetting your nappy without a second thought”.

He sat up and looked round her bedroom and was shocked to see that on the top of a chest of drawers was a huge stack of terry nappies, which he estimated to be over two dozen. They looked like regular nappies but clearly bigger, because another pile of smaller nappies were piled alongside. He was later to find out that the baby size diapers were for use as stuffers. One of the drawers was open and it was full of plastic pants in various colours, some with vivid nursery prints of rattles, teddies, unicorns and other juvenile subjects, then others that were pastel colours trimmed with lace, bows and other sissyish trimmings.

On the floor was a large white bucket with a close fitting lid. It proclaimed “Andy’s wet nappies” but worryingly there was a similar pink bucket next to it for soiled nappies. There were unopened packets scattered all over the floor, bibs, mittens, dummies, baby bottles. Piled up in one corner were what he assumed were disposable nappies with varying levels of absorption. This was clearly a plan that had not reached completion, since nothing had been properly sorted. A travel rail along one wall had a dozen or more hangers with what looked like body suits and sun dresses.

Olivia pulled back the bed clothes and looked lovingly at Andy as he suc-ked his dummy with his cute pink trimmed bib that declared ‘Mummy’s Baby’ and was looking decidedly soggy. Best of all was his puffy clear plastic pants that showed a wet, grey-yellow towelling nappy that clung to him tightly.

She applied a cuff to his other ankle and shuffled off his pants and nappy over first one foot and then the other, replacing the cuff after each action. Andy sat on her bed naked and confused. She told him to lift up as she slipped a new nappy under him and fastened it tightly with pink tipped safety pins. She completed his protection with a pair of snap popper plastic pants.

Andy continued to suc-k on his dummy, he could not work out why he was so attached to it. There was something inside of him that had snapped on that first night with some strange drug. Olivia had clearly gone mad, there was no way he was going to cooperate and no possible way that she could bend him to her will.

Olivia disappeared without a word and Andy felt anxious. He pulled the covers over himself and gave a small shiver. His bladder was beginning to fill again and he was anxious to get free so that he could use a proper toilet. He sat up and lent forward to examine the cuff, in addition to a buckle there was a secure padlock. He had no chance of releasing it and would have to wait for another opportunity.

Olivia was returning and he returned to a prone position, trying to look innocent as if all was normal. In her hands was a tray containing a baby’s bottle on one side and shaving paraphernalia on the other. He felt his face, it was a bit rough, but not that bad, as his beard was very light and not enough to even grow a decent moustache. “No silly! I need to shave your nappy area or you will get a rash. Little babies do not have hair down there, unlike their mummies who have lots”! She lifted her nightgown to show him her luxurious growth and a dim memory slowly came back to him. Andy started to struggle, but being secured by both his feet he could only move his upper torso. Olivia looked annoyed, grappled his dummy and tore it from his mouth. Andy looked shocked but before he could do or say anything she had replaced the dummy with the teat of the feeding bottle. As the first drops of milk passed his tongue, he began to suc-k and realised that he had been duped again. His mind started to drift, he felt compliant, woolly and open to suggestions but he also became limp and floppy, totally lacking coordination.