The Settlement

[Sandra B]

Chapter 28.  Lights.  Camera.  Action!

Sally Buttons made her usual visit Saturday morning.  It was more of a check-up this week.  After she had seen Philip, and ascertained that he was feeling fine, she had a private word with Tina.
“’Ow’s it goin’ then?”
“Fine.  No signs yet.”
“No, there won’t be no enlargement for several weeks at the earliest.  'E’s taking everythink regularly?”
“I’m making sure of that.”
“An’ the other thing?”
“I get the impression he’s fairly overwrought!  I’m going to leave him alone for the time being.  I want to see if he can deal with it himself.”
“Well, darlin’, that up to you.  As long as ‘e’s feelin’ randy, he won’t suspect anythin’ else is ‘appenin’.  Not till it’s too late!”

Cynthia was due to arrive at nine Saturday night, so Philip made sure to get his chores finished by eight-thirty, and change into something less conspicuous.  He couldn’t bear to think about what was going to happen the next day.  He found a simple grey knee-length skirt and maroon roll-neck jumper, and put on tights and brown shoes.  Even so, Cynthia seemed quite surprised when he answered the door.
“Hi Cynthia.  Come in.”
“Hi Philip
Oh, I thought you just wore girls’ clothes for school.  You look nice!”
“Nah.  I wear what I like, when I like,” he lied.
He introduced her to Tina and his aunt, and left them to talk while he went to make them drinks.  It had become automatic now, his habit of being the waitress.  They all sat around chatting.  Cynthia found it fascinating how Philip appeared to be ‘just one of the girls’.  She couldn’t wait to tell all her friends.  In fact, she made up some story about needing a snap of him as a test for the filming, and retired to the toilet to send it to all her contacts.  She needn’t have bothered.  There was better to come.

At bedtime, Philip couldn’t wait to try on his second nightie set, the pink one with mauve flowers.  He was much better behaved that night.  He wore a pair of underpanties under his bloomers to help keep himself in check.  At seven thirty Sunday morning he woke, yawned, and tucking his doll under the covers, got out of bed.  For a minute he had forgotten all about the filming.  He went over to his wardrobe mirror, and admired himself.  The door swung slightly, and he caught sight of the far side of the room.  There, calmly sitting in a chair filming, was Cynthia!  He swung round.
“What the
?  What are you doing here?” he shouted.
Cynthia had a delighted smirk on her face.
“I’m filming you, silly.  Don’t you remember?”
“But
but
you’re not supposed to be in my bedroom!”
“Your aunt suggested it.  She said if the film was to be honest, we should film everything you do.”
All this time Cynthia carried on filming, following Philip with the camera while he paced up and down in agitated frustration.
“But
that’s not what I agreed to
.it’s not fair
.I’m going to the bathroom!  Don’t try and follow me there!”
But she did follow him, all the way to the bathroom door, until he slammed it in her face.
“This is priceless!” Cynthia said to herself, out loud.  “This is going to be some film!”

In his haste to escape into the bathroom, Philip and forgotten to bring clothes with him.  Not that that would have helped, seeing as he was going to have to put on his maid’s outfit.  But he managed to avoid Cynthia by bursting out of the bathroom and running into his bedroom before she’d had a chance start the camera again.  But now, he knew, his real problems would begin.  He had decided that the best he could do was to wear his winter outfit.  But when he looked for it, it was missing.  He paced up and down, not knowing what to do.  Then there was a knock at his door.
“You’re late for work, Philip.”  It was his aunt.  “Is there a problem?”
“I can’t find my winter uniform, aunt.”
“It’s out for cleaning.  Wear the summer one as you usually do.  And hurry, please.  I don’t want to have to punish you in front of Cynthia.”
So there was no choice.  He put it on, with the thickest pair of tights he could find, and his patent leather maid’s shoes.  He thought it best to keep on his underpanties, too.  He took a deep breath, opened the door, and walked out.  Cynthia was ready.  Her eyes widened with amazement, but she focussed on her task.  For the next hour and a half she followed him everywhere, shot him from every angle she could think of, including lots of slow panning from his little headdress to his shoes, and back again.  Oh, she was enjoying this!  When he was eventually allowed to change, his aunt decreed he should wear a little short blue satin frock, ruffled white panties, and white socks.  It was a nice day, windless and quite warm for the time of year, and his aunt sent him into the garden to play, where, she said the light would be better for the filming!
Cynthia would gladly have stayed the whole weekend, but of course Madison arrived before her time, ready to take over.  When Tina showed her into the garden, at first she couldn’t believe what she was seeing, and gripped Cynthia’s hand in inexpressible delight.  At twelve, Cynthia took her memory card, Madison inserted a new one, and the seamless record of Philip’s life continued relentlessly.  Philip was sitting on a plastic sheet, eating a snack which Estella has thoughtfully brought him, so Cynthia told Madison to put the camera on its tripod for a moment.  She drew her friend aside.
“Listen.  I’ve been thinking.  Before you hand in your memory card, download your own copy of everything you’ve filmed, right?  Just in case.  It would be a shame to edit out any of this!”
“Yeah.  Brilliant.  I can’t believe he’s dressed up as a little girl.”
“Wait till you see mine!  He was a maid this morning!”
“What?”
“True.  And he wears a baby doll nightie in bed!”
“Oh, my god.”
“Anyway, gotta go.  Enjoy yourself, Maddy!”
“Oh, don’t worry..."

[Sandra B]

Chapter 29.  Rude Boy.

Aunt Estella was busy all the afternoon preparing food for her guests.  She discovered she had run out of smoked paprika, so she sent Philip down to the corner shop to buy some.  Totally resigned to his fate, he didn’t even bother to protest.  Madison followed him all the way, recording not only her subject, but the pointing, stares, and giggles of passers-by.  The lady serving in the shop made the most of his embarrassment.
“My, my, you’re a grown-up little girl, aren’t you, dearie?  Does your mummy know you’re out all by yourself?”
Philip grimaced.
“I’m not by myself, as you can see!” 
He would have done better to keep his mouth shut.
“Ooh, what a sulky child.  And what can I do for you?”
“I want some smoked paprika.”
“Yes
.”  She didn’t move.
“Please,” he sighed.
“That’s better.  Bad manners don’t suit you, darling, being so pretty an’ all, and having such a gorgeous little dress
ooh, and knickers, I see!”
She handed over the jar and took his money.
“Here, darling, have this.”  She handed him a Chupa Chup.  “Pop it in your mouth – it may sweeten you up a bit.”
Philip took the lollipop but declined to thank her.  He turned and headed for the door, Madison following.  The shop lady addressed Madison.
“What a rude little puss!  If she were mine, she’d be over my knee with her knickers round her ankles having her little bottom spanked!”
I’m never going in there again! thought Philip, as they returned to the house.

The afternoon passed slowly.  His aunt and Tina were busy making preparations for the evening, so he was still banished to the garden.  Tina came out with some toys for him to play with, including his doll.  He sat unhappily on his plastic sheet.  Seeing he was going to be sitting there for a while, Madison put the camera on its tripod and sat down opposite him.  It was warm in the sunshine.  He felt himself becoming aroused again.
Why does that keep happening? he thought.  He held down the front of his frock, and picked up his doll to help disguise his erection, holding it in his lap.  Madison hugged herself in delight. 
“Do you love your Dolly, Philip?” she asked, sweetly.
Philip at first declined to answer, but then thought better of it.  What he didn’t want to do was to antagonise any of these girls.  They would be in charge of the editing, after all.
“Yes, Madison.”
“What’s her name?”
“Milly.”
“That’s a pretty name.  Did you name her?”
“Yes.”
At this point Tina came into the garden to check on them.
“How’s it going, Madison?  We’ll be finished soon and you can both come in.”
“Actually we’re fine out here.  Aren’t we, Philip?”  He nodded.
“Would you like something to eat or drink?”
“Yes,” said Philip, “crisps and Fanta.”
Tina ignored him.
“Madison?”
“Thank you.  Anything Philip wants would be fine for me.”
What’s his problem today? thought Tina.  I hate him when he starts behaving like this.
“Are you all right, Philip?  Knickers not too tight or anything?”
He glared at her.
“They shouldn’t be,” laughed Madison.  “They’re big and puffy enough.”
“Well that’s because they’re supposed to be worn over a nappy,” smiled Tina.
“Really?  Gosh, what a pity you don’t
.”
“Well, we do, as a matter of fact
”
“No!” shouted Philip, visibly shaken.  “I won’t!”
Tina raised her eyebrows.  “Won’t?”
“Philip?”  Aunt Estella’s voice cut into the conversation.  “You’ll do as you’re told!”

[Sandra B]

Chapter 30.  Terry Time.

“But, aunt
.!”
“No arguments.  There’s not much point in Madison filming you sitting on your bottom in the garden, doing nothing, is there?  Give the poor girl some action!”
“I’ll take him and put a nappy on him,” said Tina.  “Come on Philip.  Come on!  Take my hand and we’ll go upstairs.”
Madison hurriedly took the camera off its tripod and followed.
“Please, Tina, not with her filming.”
“Oh, don’t be such a sissy.  This is a reality movie, remember?  Please don’t make a fuss – you’ll just make it worse for yourself.”
“But Tina,” he whispered, “I’m
my thing’s all
you know!”
“Oh, dear, Philip!  What is your problem lately?  Why didn’t you wear your rubber underpanties?”
“I did.”
“Well that’s all right, then.  They should keep you under control.  You only have to wear a nappy for an hour or so anyway.  Then you’ll need to get ready for this evening.”
What was the point in arguing?  It was already a nightmare.  It could hardly get any worse.  He submitted to lying on Tina’s bed, and having his knickers removed preparatory to being nappied.  He kept his eyes tight shut the whole time.  Tina saw Madison’s mouth drop open when she saw Philip’s bulging latex underpanties – well, it was quite an impressive sight – and she left him uncovered while she searched for the nappy and the pins, allowing Madison to capture the episode at leisure.  At last she returned.
“Okay, baby – bottoms up, please!  Good girl!”
She folded on the thick towelling and pinned it securely at the front.
Philip expected to have his ruffled knickers put back on, but Tina had other ideas. 
“On reflection, I don’t think they’ll fit over that nappy.  Never mind!  I’ve got something even better here.  She went to her bottom drawer and pulled out a cellophane packet.  Philip stared.  Plastic pants!  In different colours!  Where had she got all this stuff?  Had she been intending it for him?  It appeared so, because he saw from the label they were “adult-L”.  She hesitated for a moment, then selected a pair in translucent pink. 
“They don’t match your outfit but they’re the prettiest, I think.  Stand up, please.  Good girl.  Hold up your frock.  Step in carefully – we don’t want to tear them, do we?”
He obeyed, and Tina pulled them up over his bulky nappy.  The elastic waist and legs snapped neatly into place.  She fussed around, tucking in edges of towelling.  Madison gleefully recorded every moment, occasionally panning up to Philip’s burning face.  When Tina was satisfied, she gave him an affectionate pat on the bottom.
“There.  You’ll do.  Now go and show auntie your new panties, there’s a good girl.”
She followed Madison down after him.
“I hope your friends won’t find this too boring.”
Madison simply laughed by way of reply.

[Sandra B]

Chapter 31.  Hot and Saucy.

Downstairs, Aunt Estella was eulogising about Philip’s appearance.
“He looks so sweet, don’t you think, Madison?”
“Yes, Miss Crowthorne.  I love those little plastic pants.”
“Yes.  I’m so glad they fit.  We weren’t sure
”
“You got them for me, then?”  said Philip, displeased.
“Oh, I know we should have told you, dear.  But we wanted it to be a surprise.”
“Well it was a surprise, all right.  Look Madison, can you stop filming for a minute?  I want to talk to my aunt!”
“No, dear.  Madison is not allowed to stop.  Anything you want to say to me, you can say in front of her.”
“Oh, never mind.  I’m going back into the garden.”
“Don’t forget you need to come in and change at six.  My friends are arriving at seven-thirty.”
Philip didn’t reply, but waddled off, enc-umbered by the thick layers of towelling between his legs, followed by his shadow.  The rest of the afternoon was uneventful.  Philip sat on his plastic mat, in his plastic pants, toying with Milly.  Madison fixed the camera on its tripod and played with her phone.  At six his aunt called him in to get changed.
“Your outfit’s on the chair in your bedroom, dear.  When you’re ready Tina will do your makeup.”
“She can stay outside, this time,” he replied, glancing at Madison.
“Well, I suppose that’s reasonable.  You can’t be expected to undress completely in front of the camera.”
“Thank you, aunt.”
So Madison stayed downstairs.  Philip made his way to his room.  He closed and locked the door behind him.
“God!  Peace at last!”  He sat on the bed and began to undress.  Plastic pants, indeed!  How old did they think he was?  And a nappy!  “They’re all crazy,” he said out loud.
He stripped down to his underpanties.  He was still in a state of semi-tumescence, but at least he was contained.  He touched himself gingerly, making a spasm of pleasure run through his body.  Why am I feeling like this?  he wondered.  It’s bad timing, that’s for sure.  Now, where’s my uniform?
But instead of his summer uniform, there was  a large, posh-looking maroon bag on the chair.  He read the white lettering on the side; "Daring Designs"!  Not again!   Philip approached it suspiciously.  He had a foreboding that his aunt was about to spring yet another surprise on him.  As soon as he peered into the bag his fears were confirmed.  He drew forth the cutest little maid’s costume in shiny black vinyl, with a high white vinyl collar and puff sleeves.  The sleeves and the hem of the skirt were trimmed with white fur.  The skirt was short, and supported on a layer of very stiff polyester tulle, so that it stuck out all round almost like a little shelf, leaving no room for modesty.  The back of the dress, from the waist to the neck, was split, and each side pierced with silver eyelets, through which ran a long black lace.  The collar fastened with a press-stud at the back.  He also noticed that it had shaped breasts, with padding to keep them firm.
“No
please
”
He laid the dress on the bed and delved further into the bag. White hold-ups, also trimmed with fur.  A pair of little white gloves, ditto.  And a headband of white fur too.  Worst of all, a pair of black latex panties, even those trimmed with white fur!  Underneath the chair, a pair of patent leather black pumps with block heels and laces.  He sat back on the bed, and buried his face in his hands.
He didn’t move for some time.  Then he was roused by a soft knock at the door.
“Philip?  How are you getting on?  You’re going to need help with that dress.”
He groaned.  Tina pushed open the door.  “You okay?”
“What is this.  You’re idea?”
“My mum’s actually.  But I think it’s rather fun.  Sort of kitsch, you know.  Don’t take it so seriously.”
“Fun for you.  You don’t have to wear it.”
“Oh, come on.  I heard that you suggested yourself you should dress up as a sexy maid as a joke.”
“Who told you that?”
“Cynthia.  Did you?”
“Yeah, but only cos I knew I was going to have to.  And I didn’t say “sexy” maid, either.” 
“Well, you’re always sexy, anyway.  Let’s get it on you, and you can welcome mum’s guests in style.  Come on.”  She picked up the dress.  “Arms in.  Then I can lace it up.”
He knew there was no point in resisting. 
“Now breathe in deeply,” said Tina.  “I’m going to lace it as tight as possible, but I want you to be able to breathe.”
“Oh, how thoughtful of you.”
Tina fed the lace through the eyelets, then tightened it from the bottom up, pulling in his tummy and fitting his chest like the rind on an orange.  She tied the ends off at the neck.  He looked down at himself, and saw, not without a slight thrill, that he now possessed two quite respectable breasts.  She buttoned the collar.  It fitted closely around his neck, and came up under his chin, forcing him to keep his head erect.  Next she helped him on with his panties, which she lubricated lightly so they slid over his underpanties with ease. 
“There.  Two layers of latex.  That should keep you in check.  Does the fur tickle at all?”
“No.  It’s fine.”
“Okay.  Stockings.  These are guaranteed to stay up.”  She rolled them carefully up his legs.  They came to mid-thigh, leaving an enticing length of bare flesh between the tops and his panties.  Then she sat him down and helped him on with the pumps, which she laced with deft fingers.  Finally she pushed his headband into place, and handed him his gloves.  Then she stood back to admire him.
“How does that feel?  You’re not uncomfortable or anything?” 
“No
”  In fact, he was experiencing complex emotions.  The foreboding and embarrassment at the thought of appearing in front of Aunt Estella’s guests – and Madison, for that matter – was in conflict with a strange feeling of excitement, generated partly by the physical constriction of his outfit, but also by the thrill of feeling truly female, not in mere gender, but in sexuality.
“You look amazing.  Look at yourself in the mirror.”
Philip opened the wardrobe door.  He hadn’t even had his makeup done, but he already looked ninety percent a woman.  Tarty, in an innocent way, of course, but somehow he didn’t mind – he even quite liked it.  He found his breathing quickening, and the pressure in his panties growing.  He turned away.
“Can you
can you do my makeup, please, Tina?”
She looked a little surprised.  “Of course, darling.  Sit down.”
He sat.  She worked at his face with her usual efficiency.
“I’m going to go a little bit over the top this time.  To suit your outfit.”
The touch of her fingers on his face, so light and deft, consolidated his arousal.  If Tina noticed, she didn’t betray the fact.  Soon she had applied the last coating of mascara, and he was ready.
“Come on.  Let’s go surprise them.”

[Sissy Little Girl]

Sandra B, Philip is really in a mess right now.  He is about to be shown off to Estella's friends and Madison will be filming the whole thing.  I can't wait to see what the edited film is going to be. 

Great job.  ;D ;D ;D ;D ;D ;D ;D ;D ;D ;D ;D ;D 

[Sandra B]

Chapter 32.  Maid Dismayed.

Madison was chatting to Estella in the lounge.  It was nearing the end of her shift, and she couldn’t wait to get out of the house and get on her phone.  However, Estella had taken a liking to her, and was keen for her to see Philip’s “fancy” maid’s outfit before she left.
“Ah, here he is!” she exclaimed as Tina pushed him into the room.  “Oh, Philip, that so suits you, darling!  Don’t you think so, Madison?”
The sight of Philip made Madison forget her commission.  She stood there, dumbstruck, the camera hanging from her hand.  She goggled at him for a brief second, then gave a little scream of surprise, and dissolved in laughter.  Then, remembering herself, she took a step back, raised the video camera, and recorded the moment.
“What’s so f***ing hilarious?” spat Philip, turning red, finally driven to distraction by the relentless attention of the camera lens.  “If anything’s funny it’s not me – it’s these stupid outfits I’m being made to wear by her – and her!”  He pointed accusingly, first at his aunt, then his cousin.  It was the first serious outburst of rebellion his aunt had witnessed.  She was affronted, almost speechless.
“Why, you
.you little ingrate!  How dare you?  Do you have any idea how much I’ve spent of your clothes?  How many hours I’ve devoted to your betterment?  And you have the impudence to accuse us
. “  She put her hands on her hips.  “And pour out all that foul-mouthed invective in front of your schoolmate, who’s spent the whole day working on your project while you lounge around being waited on?”
Philip could see Madison still shaking with laughter behind the lens.  His aunt continued.
“If my friends weren’t arriving any minute, I’d wash your mouth out with soap and water, young man, and then put your over my knee and give you such a spanking
”
Oh, yes, please do that, thought Madison. 
Philip stood there, furious but impotent.  He knew his aunt kept a leather paddle hanging behind the door of the broom cupboard.  He had seen and registered it, and it had sent a shiver down his spine.  He was afraid that one day she might really use it.  He suffered a brief internal struggle, but then gave way to the inevitable.
“I’m s-sorry, aunt
  I didn’t mean
  I’m sorry I swore
”
“Well, I suggest you apologise to Madison, first of all.”
“I’m sorry, Maddy
”
Madison kept on filming, smiling quietly all the time.  Momentarily she zoomed in on his face, then returned to a full-length view.  Just stop filming me for a moment, for god’s sake, he wanted to scream.  For the first time since he entered the room he suddenly remembered that his panties were on full view, and that his erection hadn’t yet subsided.  Instinctively, he reached down and took it in his hand, wanting to check its visibility and, if possible, subdue it a little.  Immediately realising every moment was being recorded, he quickly released it again, blushed an even deeper shade of red, and starting shifting from one leg to the other in his confusion. Finally, he folded his arms and tried, with a notable lack of success, to look casual.
Inwardly Madison squealed with delight.  The perfect little vignette to end her session.  She decided to torture him a little more.
“Oh, that’s all right, Philip.  I’m just trying to do my job, you know
”  She assumed an expression of virtuous sadness.  “I hate it when you swear
”
“I’m really, really sorry.  I’ll make it up to you
”  You already have, she thought.  Wait till I turn that into a still!  “I know you’ve worked very hard today.  I
”
But here he was interrupted by a ring at the bell.  Aunt Estella looked at her watch. 
“Oh, it’s only seven.  That must be
Freida and Janie, is it?”
“That’s right, Miss Crowthorne.”
“I’ll get it,” said Tina.
“No!  Tina!”  Tina stopped in the doorway.  “Let the maid answer the door.”
“Of course, mummy.  Sorry.”

Madison followed Philip along the corridor.  He bit his lip with a mixture of annoyance and embarrassment.  It wouldn’t have been so bad if he wasn’t feeling so aroused.  Why was he like this recently?  Was it
was it that wearing this sort of outfit actually made him feel
sexy?  If he had known the real reason, he would have been more than just annoyed

“Wait a minute, Philip.  Before you open the door
”
Madison positioned herself to one side, so that she could film her friends’ faces when they saw him. 
“Okay.  Go ahead.”
Bracing himself, he yanked open the front door.  There were Freida and Janie, side by side, both dressed as for a party.  He saw them stare, and he saw realisation slowly dawn.  They made no attempt to come in.
“Oh
my
god!”  said Janie, from behind her hand.  Freida’s mouth opened in delight, but she seemed struck dumb.  She ran her eyes up and down him, taking in every detail.  Then she smiled evilly.
“Love the fur trimming, Philip.  Have you ever seen an outfit like that, Janie?”
“Never.  Cynthia  promised us a surprise, Philip.  She didn’t tell us
”
“Are you coming in, or what?” he responded, irritated.
“Oh, don’t rush us, Philip,” said Freida.  “After all, I can see you’ve really gone out of your way to impress us, haven’t you?”
Philip could only grunt in reply.  The girls condescended to come in.  Like the dutiful maid he was, Philip took their coats and put them in the bedroom.  Then he led them into the lounge, where Aunt Estella and Tina were waiting.
“Welcome, girls!  I’m Philip’s aunt, Estella.  This is my daughter, Tina.  I hope you’re going to enjoy your stay.”
“Thank you, Miss Crowthorne.  I’m sure we will,” returned Freida, with a meaningful look.  “Philip, you look absolutely gorgeous!”
“He does, doesn’t he?” agreed Tina.  “I’d love to stay and be waited on by him.  But I’m meeting my friends for a drink.  I’ll see you all later.  Have fun, Philip!”
Philip ignored the remark.  For the first time he didn’t feel sorry Tina was not going to be around.  Lately, she seemed to be more interested in teasing him than supporting him.  One less, anyway, he thought, as she went out of the door.
“Now, you know I have three friends arriving soon for dinner?” said Aunt Estella.  “I’ve made enough for all of us, but I hope you won’t mind eating in the kitchen.  Of course, Philip will be your maid as well, so he will serve you with whatever you want.”
“Thank you, Miss Crowthorne,” said Janie, “that’s very thoughtful.  We shall probably have to take it in turns to eat, while the other does the filming.  In fact, we should take over now, shouldn’t we?”
“Here you go,” said Madison, extracting her memory card and handing over the camera.  “Good luck.”

Janie soon had the camera ready, and commenced the new session. While Madison said her goodbyes, Freida took the opportunity to examine Philip’s outfit, stroking the fur and running her fingers over the vinyl.  He had to stand there and submit to her scrutiny, while his aunt looked on severely.
“And no more outbursts this evening, young man.  Or it’ll be the worse for you.  Understood?”
“Yes, aunt,” he sighed.
 She squatted down, ostensibly to admire his stockings, but really to sneak a close look at his panties.  She noted with satisfaction the elongated bulge in the taut latex.  She stood up. “You really like your maid’s costume, don’t you, Philip?”
He was only too aware of Estella’s baleful gaze.  “Yes, Freida.  Thank you.”
“It’s very pretty, isn’t it?”
“Yes.”
“He does have others, Freida.  But I thought my friends would appreciate one of his fancy ones.”
“One of my
?” queried Philip, looking at her a little alarmed.
“Oh, yes.  Didn’t I tell you, darling?  You have another one, just the same but in pink.  I didn’t know which one to choose, so I bought both.  But don’t worry, we’ll find an opportunity for you to wear it soon.  You’ll love that just as much, I’m sure.  Won’t you?”
“Yes, aunt.  Thank you, aunt.”
“Good boy.  Now if you’d like to bring in the wine and the sherry, my guests are due any minute.  Oh.  That must be them now.  Answer the door first, please.  Then you may serve the drinks.”   

[Sandra B]

Chapter 33.  Mary and Jill.

Philip was full of foreboding as he approached the front door.  He had no idea which friends his aunt had invited, except that there were three of them.  But when he opened the door, there was only one.
“Philip, dear.  You look lovely!  May I come in?”
“Miss Tancred.  I-I’m sorry, I didn’t realise
”
“Well, well, we’re not at school now, are we.  You needn’t look so frightened.”
“No, miss
er, madam
I was just surprised, that’s all.”
“Please, Philip,” said Christabel, giving Philip her coat and scarf as she passed into the corridor, ““miss” is absolutely fine.  You needn’t be formal with me.”
“No, miss.  Sorry, miss.”
“I must say you look absolutely splendid in that little outfit.  Estella has such good taste, don’t you think?  You needn’t show me through.  I’ve been here enough times in the past.”
Philip went into the bedroom and laid Christabel’s coat and scarf on the bed.  He felt unnerved by her arrival.  Now there was the head as well as the two girls to witness his discomfiture.  But he pulled himself together, and prepared to return to the lounge.  Before he could move, however, there was another ring at the bell.  He hurried to answer the door.  The remaining two guests had arrived together.
“Hello, sweetie.  Can we come in?” said the first, the shorter of the two, with an innocent smile.
“You must be Philip,” said the other, taking him in at a glance, “Estella told us she had a new maid, but she didn’t warn us how pretty she was
”
“Of course.  This way please.  If you’d care to give me your coats
”
The two guests were quite dissimilar.  They were both, thought Philip, late thirties.  Probably they were more friends “from the old days”.  One was buxom and motherly-looking, with slightly prominent china-blue eyes, untidy hair,  and a permanently sympathetic expression on her face, as if condoling with the world in general.  She wore a blouse and narrow skirt, both apparently a size too small for her.  The other looked more sophisticated, in a cheap sort of way.  Taller and slim, small brown eyes, a hint of fake tan, bronze-coloured hair out of one of those women’s magazines that you find in doctors’ waiting-rooms, black wet-look leggings, black knee boots with stiletto heels which she appeared to be having difficulty balancing on, and a short, tight black jumper.  Philip dumped the coats and followed them into the room.
“Mary, darling!  How are you?  Jill!  Lovely to see you.”
“Christabel!  Estella!”
“Jill!  Mary, sweetie!”
It was clear they all knew each other, anyway.  Maybe they’ll just concentrate on each other, get slowly pissed, and leave me alone, thought Philip, as he went to get the drinks.  As he was in the kitchen loading the bottles onto a tray, he could hear Estella introducing Freida and Janie to her guests.  He expected the girls to be a little embarrassed by the presence of their headmistress, so he was surprised when he heard Freida chatting to her as if she were an old friend.  It was a little odd, he thought.  When he returned they were all seated around the table laughing, and to his surprise his aunt ordered him to bring two more glasses for the girls.  Well, at least they’d stopped filming for a bit.  But that was not to last.

After about ten minutes the girls stood up and got the camera working.  The four women sat one at each side of the table, sipping their drinks and reminiscing.  Philip, as he had been instructed, stood to one side awaiting orders.  He listened to the conversation with interest.  He gleaned that Mary had indeed been an old college friend of his aunt’s, whilst Jill was a more recent acquisition.  They were talking about things he didn’t quite understand.  On several occasions, Jill mentioned her “trainees”, and Mary her “babies”.  Christabel must have noticed the puzzlement on his face.
“I think your little maid is curious about our conversation, Estella.  Are you, Philip?”
“N-no, miss,” he stammered, “not at all.  I was thinking about something else.”
“Little liar,” laughed Jill.  “Shall we enlighten her, Stella?”
“Philip, dear.  Ask my guests anything you like.  Go on.  Were you interested in Mary’s babies?”
“Well, I did wonder how many
”
“I have five at the moment,” said Mary.  “Though I could always cope with more.”
“Are they all yours?”
“No, silly.  I just look after them.”
“Oh, I see.  A sort of crĂȘche.”
“Sort of.”
“Are they all little?”
“Quite little.  The youngest is fourteen, the eldest
he must be nearly twenty-eight now.”
“What?” exclaimed Philip, frowning.  “How
?”
The women all laughed at his confusion.  Estella explained.
“My friend Mary looks after grown-up babies, Philip.  They get brought to her by wives, sisters, aunts
  Naughty boys who need subduing and retraining.  After a few months with her they emerge much more compliant.”
“And happier, too,” added Mary.  “Some of them elect to remain as babies.”
“I’ve never heard of anything like that,” said Philip, amazed.  “I mean, do they choose to go to you in the first place?”
“Oh, no,” laughed Mary, “they don’t choose.  Usually they have done something naughty, and submit rather than be exposed.  Occasionally they have to be brought to me by force, but that’s rare.  Once I have them they’re put in restraints for the first month, sometimes longer, until they become completely conditioned.  You’d be amazed how easily some of them can be persuaded to regress.”
“I see.  I can’t imagine how
what you
.”
“You’re going to have the chance to find out first hand, Philip,” interjected his aunt.  “I’ve booked you a month with Mary in the summer holidays.”
Philip stared at her, and then at Mary, in alarm.  “No
I don’t need
I haven’t been naughty
and I’m going to be a really good maid, aunt, you’ll see!”
He heard the girls spluttering with mirth.  He turned to them.  “Shut up, you two!”
“You see,” sighed Estella.  “He has these little outbursts of rudeness.  I hope you’ll  be able to cure him, Mary.  Will a month be enough?”
“Oh, I think so, dear.  I’ll give him the intensive course.”
“Thank you.  You’re so kind to me.”
Philip was incoherent with fear.
“Aunt, please
.  Listen, I’m gonna be so good!  What do you want me to do?  Anything!”
“I want you to go see Mary, darling.  That’s what I want.  And that’s what’s going to happen.”
He advanced to the table and confronted his aunt.  “I’m f***ing not!  It’s too much!  You can’t make me!”
Aunt Estella didn’t reply.  She gave him a long, withering stare, then rose from her chair, and left the room.
“W-where’s she going?” asked Philip, nervously, suddenly repenting his boldness.
“Philip, that was a mistake,” said Christabel, resignedly.
The words were hardly out of her mouth when his aunt returned.  The leather paddle was in her hand.
“Aunt.  No.  I’m sorry
”
“I warned you, Philip.  Ladies?  I’m going to need a little help here.”
The three of them rose.  Philip backed away, but they surrounded him.  They dragged him, struggling and protesting, to the sofa.
“Over the back, I think,” said Estella, calmly.  “I’ll be able to get a better swing like that.”
He was bent over the back of the sofa.  Mary and Christabel sat down on it and held his arms.  Jill sat on the floor and wrapped her legs around his ankles.  His little stiff skirt stood up straight, leaving his bottom unprotected.  Freida and Janie were almost hysterical with delight.  They could never have imagined anything as wonderful as this!  They positioned themselves to the side, where they had a perfect view of proceedings.  Poor Philip was already beginning to sob and plead.  But his aunt was unrelenting.
“The first ten with your panties on, to warm you up.  The second ten
.”
“No, aunt, please, please
.!”
The first blow landed.  Philip screamed.  The broad leather paddle made a loud crack as it connected with his bottom, sending a wave of pain through his body.  Pain that didn’t subside, but grew steadily with each stroke.  He ceased to struggle, trying to focus on counting the strokes, but each successive one drew from him a yelp or a howl of agony.  When the first ten were done, Estella allowed him to rest for a minute.  Then she unceremoniously pulled down his panties and his underpanties, revealing a pair of glowing buttocks trembling with apprehension.  Freida now had the camera, and she zoomed in for a few seconds before returning to a wide view.  Philip was squirming with pain and mortification.  Estella resumed.  She placed the blows alternately on one buttock then the other.  She took her time, allowing the pain to develop after each stroke before applying the next.  Philip was sobbing helplessly.  Through blurred eyes he could see his tears dropping onto Mary’s skirt, making little wet stains.  His bottom became a livid red, the shape of the paddle clearly demarked on his pale flesh.  When it was finally over, and the ladies released him, he sank to his knees on the floor, eyes tight shut.  Estella left the room to replace the paddle, and returned with a jar of cold cream.
“Mary?  Maybe you’d like to do this?  You have the most experience
”
“Love to, Stella.  Come here young man.”  Christabel helped him around to the front of the sofa.  Mary spread a towel on her lap, and Philip was instructed lie face down on it.  He turned his head and opened his eyes.  The first thing he saw was the delighted faces of Janie and Freida, either side of the camera lens.  With a groan, he turned his head back the other way.  As Mary’s expert hands began to apply the cream, with unexpected gentleness, he sighed with relief.  He had learned his lesson.  No more swearing.  No more outbursts.  No, he was going to be a model maid from now on.  Maybe
maybe Aunt Estella would take pity on him, and let him off the trip to Mary’s place.  Though she could hardly be any worse.  But his cogitations were interrupted by his aunt's icy voice.
“When you’re done, panties back on and serve the starter please, Philip.”