The Settlement

[dolly bo peep]

SandraB,

I'm catching up and really enjoying your story.

Now that we know more about the backgrounds and motives of Estella, her daughter Tina, and Christabel, the better we can appreciate what further fates they have in store for Philip as they have their "bit of fun" at his expense.

I'm pretty sure Nikki as Philip's mentor, along with some of her classmates, will fun at Philip's expense.

I'm really looking forward to your fututre chapters.

[Sissy Little Girl]

SandraB, That is messed up.  I thought Tina was Philip's ally.  Turns out, she was just as devious as her mom.  Both Estella and Christabel had bad relationships with men.  Philip is now in the clutches of two devious women and Tina.  Me thinks he will have a hard row to hoe. 8) 8) 8) 8) 8) 8) 8) 8)

[Sandra B]

Chapter 13.  Friendly Persuasion.

As he followed the corridor, clutching his little backpack in his arms, the object of many surprised stares and undisguised mirth, his anxiety increased.  He hesitated at the classroom door.  Miss Waters hadn’t yet arrived.  There was a hubbub of conversation within.  He peered into the room.  He couldn’t see Nikki anywhere.  He wasn’t sure whether to go in, or to wait outside for her.  One of the girls, checking to see whether the teacher had arrived, caught sight of him hovering uncertainly in the corridor, and immediately alerted her friends.  The news spread quickly, the conversation ceased, and was replaced by excited whisperings punctuated by suppressed giggles.  Poor Philip turned bright red once again, and for a moment thought of throwing down his bag and making a run for it.  Fortunately for him, at that moment Miss Waters came round the corner.
“Philip!  Good afternoon.”  She approached.  “You should have gone in and met the girls.  Never mind.  Come on – I’ll introduce you.”
She took him by the arm and led him into the room.  The desks were arranged in four rows of five.  The girls immediately became quiet and resumed their seats.  Miss Waters was young, inexperienced, and rather naĂŻve; it was the strictness of the headmistress that enforced discipline at Caroline Norton.
“Girls!  I’d like you to meet our newest pupil, Philip Timothy.  Philip will be joining us for the rest of the year.  Please embrace him into the class and make him feel at home.”
Philip, cheeks still burning, surveyed the rows of faces, their expressions ranging from shock to amusement.  There was a moment of silence, before a girl in the second row shouted gleefully, “Hello, Philip!” – and then the rest followed.  There were a couple of muted wolf whistles from the back.  Philip forced a smile, fidgeted uncomfortably, and in his confusion dropped his backpack, spilling his pencils onto the floor, and provoking a burst of laughter.  He heard one girl say, “my little sister’s got the same one!”  As he scrabbled to collect his property, Miss Waters addressed her pupils, doing her best to look dangerous.
“Now girls, quiet please.  It’s not funny.  If I have any more stupidity, I’ll be handing out lines.  Yes, Rebecca, I’m talking to you.”
At this point, in sidled Nikki.  She stopped, glanced at Philip, down on his knees at the front of the class, gave a smirk of amusement, and walked casually to her desk next to the corridor.  Miss Waters said nothing.  It appeared Nikki had some sort of protected status.
“Philip,” she continued, quietly, “if you’d like to go and sit next to Nikki….  Then we’ll get on.  Please see me if there’s anything I can help you with.”
Philip made his way over to his desk, at the left-hand end of the second row.  Nikki shifted up against the wall, and he seated himself on her outside, carefully holding down his skirt as he did so.  He could feel a dozen pairs of eyes riveted on him.  He kept his on his desk.  Miss Waters took registration.  There were two afternoon lessons, and that day Philip didn’t have to move to another room.  Nikki left for the last period, however.  He wasn’t sorry to see her go.  She had ignored him completely up till then, playing with her phone most of the time.  Her place was taken by a girl with soft brown eyes and a pleasant face, who introduced herself as Carol and shook his hand.  She behaved towards him with such delightful normality that, by the end of school, he felt much more cheerful, and was reassured he had also made a good friend.

It transpired that Carol was studying two of the same subjects as he, namely Maths and Biology, so they got to see each other quite a lot that first week.  He decided he’d have to confine his relationship with her to school however.  Even if she was just a friend, he knew Tina wouldn’t tolerate another young woman in the house.  In any case, there was no hint of anything more than friendship between them.  But she felt like an ally in a not altogether friendly environment. 
However, as the week progressed things seemed to improve.  Most of the girls in U.1 came to accept him and behave towards him as just another pupil.  Notable amongst the exceptions was Rebecca – the girl that Miss Waters had rebuked – and her friend Valerie.  But he decided to ignore them.  By Friday, despite his domestic duties and demanding routine, he was enjoying his new life.
“Don’t forget Sally will be here in the morning, Philip,” reminded his aunt.
“I haven’t forgotten, aunt.  I think I know what’s in store for me, too.”
Sure enough, Sally Buttons had an appointment with the remainder of Philip’s body hair, which was efficiently removed with a combination of wax, electrolysis, and depilatory preparations.  The process left him feeling like an overpopulated pin-cushion, and he was quite thankful when she reverted to his eyebrows.  After her work was completed for the day, she stood back to admire him.
“That’ll do you for the time bein’, Philip.  You look bloody great!  Don’t it feel nice, bein’ so smooth and pretty?”
“I guess it will, when the pain goes away.”
She looked thoughtful.  “You’ve got potential, you know?  You could make a really attractive girl, you could.  Why don’t you let me…you know…just a low dose.  Something mild, darlin’.  There’s a huge range of stuff out there.  Properly managed, there ain’t no risks…”
“No thank you, Sally.  No.  I like myself the way I am.”
“Well, if you change yer mind…  You needn’t worry about Tina.  I ‘ad a chat to ‘er last week.  She seemed to quite like the idea.  I’ll be over next week, anyway, for a check-up.”
After she had gone, Philip took a long look at himself in the mirror.  It looks weird, he thought.  He stroked his skin.  But it is quite a nice feeling, it’s true.  Sort of clean.  He dressed in his maid’s uniform with more enthusiasm than usual.  He was beginning really to feel the part now.

Monday started off a good day.  He was with Carol for two double lessons.  That chatted quietly, and helped each other with their work.  She suggested he join the drama group, of which she was a member.  He promised to give it a try.  He was already reviewing all the societies to see which ones he might like to get involved in.  So it was in quite a cheerful frame of mind that he crossed the playground that afternoon after school had finished, and headed for the gate.  He could see a little knot of four girls gathered there.  And wasn’t that Nikki, walking away?  Yes.  What was she doing with them?  They seemed to be looking in his direction.  That was Rebecca and Valerie.  The others he thought were from the lower year.  He tried to ignore them, but as he came level, one of them called out to him.
“Oi!  You!  Philip!”
He stopped and turned to them.  The one who had addressed him, a smallish girl with an impish face and spiteful-looking eyes, he didn’t recognise.  The fourth, a blonde with a single long plait and ice-blue eyes, was also a stranger.  Rebecca and Valerie stood behind them, malicious smiles on their faces.
“Yes?”
Then Rebecca spoke.  She was a solid girl, with brown hair, a round face, and full lips.  In class, she sat right at the back, next to Valerie.
“’Oo d’you fink you are?”
“I’m sorry?”
“Why are you ‘ere?  What you doin’ in a girls’ school?  And in a girl’s uniform?”
“I understood it’s not just a girls’ school.  Boys can come here too.”
“Ooh, you “understood”, did you?  Posh little twat!”
“I’m not posh.  If you don’t like the way I speak, that’s your problem.  I didn’t ask you to speak to me.”
Then the blonde piped up.
“You don’t have a right to dress like us.  You should wear boys’ clothes.  You look stupid.”
“Who are you?”
“I’m Freida.  L.1.  All my friends think you’re just a big sissy.  You better watch out, kid.”
“Philip laughed.  “Who are you calling “kid”?  You’re a year younger than me.  I don’t give a crap what you or any of your friends think.”
He went to pass on, but the girl who had first spoken jumped in front of him.
“You don’t get it, do you?  We’ve had a meeting, see?  Any new kid at this school has to be vetted by us before they get to flounce around like they’ve bin here all their lives.  You come here, pretending to be like us, but the truth is you’re just a sissy, and you’ve got less right to be here than any of us.  If you’ve really got balls – and I doubt it – prove it.  Instead of hiding behind all that makeup and that long skirt, wear your summer one, like us.  And your socks.  I bet you won’t, cos you’re a wimp.”
“Yeah,” chorused the others, gleefully.
Philip frowned.  “I’ll wear what I want.  It’s all part of the uniform.” 
“You’re scared, aren’t you?  Wimp!  We’ll get you if you don’t, anyway.  You won’t be so coc-ky then!”  And giving Philip a shove, she led her friends away along the road.
Philip stared after them.  “Idiots,” he murmured, though he was feeling slightly anxious.  “What can they do…?”
He felt a touch on his shoulder.  It was a tall girl who he’d noticed in U.2.
“Hi.  I heard all that.  Don’t worry.  Which way are you going?”
“Oh…I was going to walk…  It’s that way, back towards Dayton.”
“Can I walk with you part of the way?”
“Sure.”
“I’m Olivia.  You’re Philip, aren’t you?”  Philip nodded.  They started walking side by side.
“Who was that short girl?  The ringleader?”
“That was Sadie.  L.1.  She and her little gang like to terrorise freshers, that’s all.  I don’t know how they get away with it.”
Philip looked across at her.  He noticed she was wearing a little red lapel badge.
“You’re a prefect?”
“I am.”
“How many prefects are there?
“Four.  Not many.  We’re supposed to keep an eye on stuff like this, but whenever we do report something – or someone – nothing seems to get done about it.  There’s a little gang of them, about six or eight.  They get away with murder.  If you don’t do what they say, you’ll find they’ll get you somehow.  Glue on your seat, paint in your desk all over your stuff, things like that.  One girl who defied them got stripped down to her panties and socks and chained to the school railings earlier this year.  She refused to say who did it.”
“Why?”
“I’m not sure. I don’t think she even told her parents.  It all just blew over.  I get the impression the head doesn’t want to know, or she’s protecting the perpetrators, or something.  It’s strange.  Even us prefects feel we’re purely a token presence.”
“So what do you think I should do?”
“You want my honest opinion?”
“Yes.”
“I’d like to tell you to report it.  But honestly, it’s only a little thing.  Maybe just do it, and hope they’ll leave you alone.  At least, till you’re feeling a bit more confident and you’ve made some more friends – got some backup.”
“Okay, Olivia.  Thanks for your advice.”
“No problem.  I have to go this way.  See you tomorrow.”
“Yeah.  In my little skirt!  Maybe!”
They laughed and parted.

[Sandra B]

Chapter 14.  Rubber Solution.

Philip’s amusement soon faded, however, and he walked thoughtfully back to his aunt’s house.  He didn’t fancy wearing that skirt at all.  He would only attract more attention.  And suppose it was windy?  It wouldn’t have been so bad if he were a girl, but his little panties were patently unsuitable for an adolescent male.  On the other hand, he felt much more confident now that Sally had done her work.  He still had a frown on his face when Tina admitted him.
“Hello, Philip?  How was your day?”
“Part of it was okay…  Where’s your mum?”
“She’s out.  Shouldn’t be back till late.  Would you like something to eat?”
“Yes, please.  I’m starving.”
“Don’t worry.  Let’s have some pasta and salad.  And a glass of wine?”
“That would be lovely!”

After supper they sat on the sofa sipping their wine.  Tina was wearing a little figure-hugging black dress.  But Philip was still worried about the next day.  He thought he’d confide in her.
“Tina?  Look, I’ve got a bit of a problem.  You know my school uniform?”
“Yes, darling.”
“What do you think of the little summer skirt?”
“I think it’s sweet.  Why?”
“I mean, what do you think it looks like on me?  I may have to wear it to school tomorrow, and I’m a bit…you know…”
“What, shy?  Don’t be silly, Philip.  It looks great on you.  Go put it on now and let me see.”
So Philip repaired to his room, took off his tights, and changed into his summer skirt.  Maybe it wasn’t that bad.  But he really needed some slightly more robust panties.  He returned downstairs.
“Darling, it looks lovely!  What are you worried about?” 
To be fair to Tina, she had little idea of what was going on at Caroline Norton.  As far as she was concerned, Christabel Tancred was a nice woman, a little mischievous, perhaps, but with a heart of gold.  Probably she thought Philip should make an effort to fit in a bit more, be “one of the girls”.  So Tina decided to give him some encouragement.
“There’s nothing wrong with it.  If you’re dubious about it, why not wear your winter skirt tomorrow, and take the little one with you, just in case you feel like changing.  In fact, that’s probably a good idea, because I’m going in late tomorrow, so I won’t be able to give you a lift.”
“But what about my panties?  They’re not really functional, if you know what I mean…”
“Talk to mum when she gets in.  Now come here.”
He resumed his place next to her on the sofa.  God, he’s irresistible in that little skirt, she thought.  He better not get too friendly with any of those bitches at school…
She put her arms round him and began planting soft, light kisses on his cheeks and lips.  After a short while, Philip forgot all his anxiety, and gave her a practical demonstration of the inadequacy of those little satin panties.  Tina was still sceptical, however, and decided to find out for herself.  Philip had just to the point where he pushed her down full-length on the sofa, and squeezed up beside her, when they heard the sound of a key in the front door!  They had to make a sudden desperate  change of position, and when Estella walked into the room they were both sitting bolt upright with flushed faces, pretending to have a conversation about pasta sauce.
“Hello, you two.  My friend had to leave early, so here I am.  Philip, how was your day, then?  Oh, I thought you wore your winter skirt today,” she added, suddenly noticing.
Philip was gripping the hem tightly, trying to think of serious, boring things.  The presence of his aunt helped.  No-one could be less stimulating than she.
“Yeah, okay.”  I might as well ask her now, he thought.  “Aunt, I need your advice.”
“Yes, dear?”
“Can we go upstairs?”
“Of course.”
She followed him up the stairs and into his bedroom.
“Well?”
“I was thinking of wearing this skirt tomorrow, for a change.  Maybe not all day.  Maybe I’ll just take it and change there if I feel like it.”
“I see…”  Her expression was one of utter innocence.  There wasn’t the slightest hint that, an hour earlier, she had received a cryptic text from Christabel Tancred: “Subject confronted.  Ultimatum issued. Expect developments.” 
“So is there a problem?”
“Yes, aunt.  There is.  I can’t wear it with these flimsy little panties.  Can you imagine what I’d look like?”
Clearly she could imagine only too well.  “Oh, dear.  I see what you mean.  Yes.  But haven’t you found your under-panties?  They’re in your drawer, at the back.”
“Under-panties?”
“Yes.  I’m, sorry, I should have shown you.  Here.”
Aunt Estella pulled his underwear drawer right open, and extracted a cellophane pack from the back.  It contained a selection of variously coloured little panties, in colours matching his satin ones.  Philip could see pink, yellow, and pale blue.  She tore it open, took out a pair, and passed them to him. 
“They’re very fine, strong latex, with tight leg bands. You’re supposed to be wearing them under the girls’ panties.  They’re designed to keep you under control and flatten out the contours.  Match the colours up and they’re completely undetectable.”
“I see.  They look quite small.”
“Don’t worry, they’re your size.  They’ll be fine.  If you use this stuff” – she produced a tube from the back of the drawer – “you’ll find they slip on very easily.  Here, let me show you.”
She laid a pair of yellow ones on the bed, and squeezed a bead of clear lubricating gel inside.  Then she placed her hand on them and rotated it until the inside was evenly coated. 
“There.  I’ll go outside while you try them.”
Left to himself, Philip stripped off his clothes and stepped into the panties.  They slid on with surprising ease, and snapped firmly into place.  They felt quite comfortable.  He tried a pair of his stretchy, satiny panties over the top.  Great!  The under-panties were quite invisible, but did their job well, smoothing out the inappropriate contours.  He felt more confident already.  Now he’d be able to wear his short skirt without worrying!
“Thanks, auntie!  He called to her.  That’s the answer.  Look, I’m going to put on my maid’s uniform now and do my work.”
“Good boy.  So what I suggest is, take your under-panties and gel with you  tomorrow, and your summer skirt.  If you want to, you can change at school.  Or just keep your winter skirt on if you prefer.”
“Thanks, I will.”
“If you give them to me now, I’ll put them in a plastic bag and pack them in your backpack with your lunch.”
“Okay.  Great!  I’ll pass them out to you.  I’ll go for yellow, I think.”
So he gave his aunt his under-panties, panties, gel, and summer skirt to pack for him.  That’s great, he thought.  I’ll play it by ear tomorrow.  If I can avoid wearing the summer skirt, I will.  But it’s there if the worst comes to the worst.  Auntie was being very helpful for once.  She does seem much nicer to me these days.  But it’s a pity about Tina.  If only we’d had another half hour!  As it is, I’m feeling, well…  I hope I’ll be able to sleep tonight.  But he had his chores to do, and he was soon in his maid’s costume, collecting up the washing.

[Sandra B]

Chapter 15.  A Friendly Dragon.

Aunt Estella was in a very good mood that night.  She opened another bottle of wine and suggested they all sit down and have a drink.
“I’d love to, aunt, but I have to put the washing in the dryer and do some ironing, replied Philip, smoothing down his apron.  He looks so cute as a maid, thought Estella, with his hair tied up with a scarf, even in the long dress.  She was looking forward to the warmer weather, when he’d have to wear the prettier short one.  And the fancy one…!  But there’ll be plenty of time for that, she thought.
“Nonsense, Philip.  You deserve to relax.  Have a drink and tell me all about your day.  I’ll deal with the washing for one night.  You should get an early night.  You must be tired.”
Philip could hardly believe his ears.  But he was tired.  So he sat and described the events of the day – carefully omitting the episode with the four bossy girls.  He did, however, mention Nikki.
“She’s supposed to be my ‘mentor’.  But she seems very strange.  She doesn’t say much, and she’s not very friendly.  Whereas the girl I met tonight – Olivia – is really nice.  Pity it couldn’t be her.”
“Oh, really,” said Tina, with more than a hint of jealousy, “what makes her so “nice”, then?”
“Well, no, that’s not the right word.  Just “normal”, I suppose.  She’s a prefect.”
“I always hated prefects when I was there.  Me and my friends…”
“Yes?”
“Oh, nothing.  So what’s this Miss Waters like?”
“Nice.  She’s very young, but the girls like her.”
“Lucky them.  I had Miss Sangster as a form teacher both years.  It’s lucky corporal punishment was made illegal.  In fact, I think she love to get back to the old days when teachers could thrash pupils for the slightest thing.”
“Christabel doesn’t think it was such a bad thing.  She says the children were much more respectful then.”
“Course they were, mum, or they knew they’d get a good beating!”
“Well…”  A slightly nostalgic look came over her mother’s face.
“Anyway,” interjected Philip, “I will go to bed if that’s all right with you, aunt.  I’ll get up extra early to do my morning chores.”
“Good boy.  Goodnight, dear.”
“Night, aunt.  Night, Tina.”

The wine helped Philip get to sleep, and he didn’t hear Tina’s whispered “good night, darling,” as she passed his door.  But his aunt, after she had finished sorting out the washing, didn’t come to bed for another hour and a half.  Instead she got out her sewing machine.  She had a couple of minor alterations to do.

[CuddleBunns]

Sandra B, I am absolutely loving the conspiratorial aspects to this story so far. I'm getting the sense that absolutely anyone could potentially be in on the plot to feminize and humiliate Phillip, and the breadcrumbs you are leaving as to what could be happening behind the scenes have me very intrigued. Bravo! Thank you for this incredible story, I look forward to reading more.

[Sandra B]

Chapter 16.  Capitulation and Remorse.

Philip walked briskly to school that morning.  The weather was a little warmer than it had been recently.  He entered the playground at ten to nine, and looked around.  He breathed a sigh of relief.  No sign of the Gang of Four, as he had decided to call them.  He joined a small group of girls from his class.
“Philip.  What do you think of this English thing?  I think it’s a waste of time.”
Miss Tancred had decreed that, starting the following week, all pupils would have an extra thirty minutes of English tuition after the first afternoon period, replacing their afternoon break.  The focus would be on reading aloud.  She had been so disgusted by what she saw as the degeneration of the spoken language amongst her students, that she was determined to try to instil some literacy into them, whatever subjects they were otherwise studying.
“Well,” said Philip, “I can see where’s she’s coming from.  And to be honest, the afternoon break was a waste of time in itself.  All we do is sit around eating sweets.  I would have preferred scrapping it altogether and leaving half an hour earlier.”
“Yeah!  We should suggest that!” exclaimed Paula.
“Don’t bother, Paula.  You know what the answer would be,” returned one of the others.

The bell rang, and they filed into class.  As he entered the classroom, who was coming out but Sadie and Freida!  They said nothing, but gave him a dirty look.  Out of the corner of his eye, Philip could see Rebecca and Valerie looking at him and whispering.  The four of them must have been in here hatching some plan.  Nikki wasn't there yet.  He sat down and opened his desk.  Lying across his books was a condom filled with something which on closer examination appeared to be golden syrup.  There was also a note.
“Last warning.  Next time we’ll burst it.”
Little bitches!  He looked around.  Sure enough, Rebecca and Valerie were smirking at him.  Valerie stuck out her tongue.  He sat there, silently fuming.  Then Nikki arrived, and he got up to let her in.
“Problems, Philip?” she asked, innocently, but with a smile on her face.
“No.  Nothing.”
“Cool.”
He was distracted through first period, wondering what he should do.  He thought of calling their bluff.  But he didn’t doubt they were prepared to do it if they didn’t get their way.  Suppose they put another one there at lunchtime, and this time they did burst it?  His stuff would be ruined.  And he’d never be able to pin it on them.  I hate them!  But by the time break was approaching, he decided that discretion was the better part of valour.  As the bell went, he went over to Rebecca and Valerie, and dumped the gloopy condom on Rebecca's desk.
“Okay.  I got the message.  You can tell your friends I’ll be wearing by summer skirt this afternoon.  Perhaps then you’ll leave me alone.”
“You will?  How nice of you!  But there’d better be no mistakes, or else….”
“There won’t.  I’ll change in the toilets before registration.”
“I’ll tell Sadie and Freida.  We may follow you just to check you’re not cheating.”
“You can if you want.  Don’t worry about me.  I don’t know what all the fuss is about.  I was going to wear it anyway, now the weather’s warmer.”
“Got your socks with you, I hope?”
“Course.”
“There’s a good boy…”
“Shut up, Rebecca!”
“What did you say?”
“Nothing.  Er, sorry.   You’ll tell the others, then.”
“Oh, yes.  Right now.  See you later, impersonator!”

Philip made his way outside, fuming.  What right have they got….?  Gang of little bitches…  I’m not gonna be their lapdog…  No way… . Then he sighed.  I hope, after I've changed, that’ll be it.
It took the whole of break before he began to calm down, mainly because the next period he was in L.1’s classroom with Carol.  She was waiting for him, already seated.
“Hi Philip.  You okay?  You look a bit worried.”
“No, not really.  I’m fine.  It’s warm today, isn’t it?  I think I might wear my summer skirt this afternoon.”
She puckered her brow.  “Yes?  Okay….  You’ve brought it with you, have you?”
“Yes.”
“Any other reason?”
“No….  Yes.  Yes, I’ve been threatened by the f***ing school mafia.  Rebecca and Sadie and that lot.”   
“Oh, I see.”  She looked down and smothered a smile.  Philip stared at her.
“What are you laughing at?  It’s no joke!”
“Philip, sorry.  I wasn’t laughing.  It’s just…I don’t know, I didn’t think you’d be frightened of a few pathetic delinquents like them…”
“Well, I’m not frightened…”
“Yes you are…aren’t you?”
“They’ve threatened to mess up all my stuff.  They won’t leave me alone, I know.”
“If you give in to them, they’ll never leave you alone.  But if you show them you can’t be intimidated, they’ll eventually get bored and find someone else to terrorise.  Don’t you see?”
Philip felt more confused than ever.  “But…”
“Yes?”
“One of the prefects advised me to go along with them.  She said…she said she thought it would be the best thing…”
“Who?”
“Er, Olivia.”
“Olivia.”
“Yes.”
“She’s one of them.  Didn’t you know?”
“She is?  I don’t believe it!”
“Believe it.  You’ve been well stitched up, you have.”
At that moment, Miss Sangster entered the room, and everyone immediately stopped talking and sat up straight, assuming willing, expectant expressions.  Philip’s mind was in a whirl.  What an idiot he’d been!  Right.  That was it.  No way he was wearing it, now.  No way!