The Settlement

[Sissy Little Girl]

Sandra B, Poor Philip will be the maid for his aunt and Tina.  His duties are many and then there is school.  He will have to wear a girl's school uniform.  I guess he will be just one of the girls at this school.

Great chapter and I can't wait for the next. 8) 8) 8) 8) 8) 8) 8) 8) 8)

[dolly bo peep]

Sandra B,

I'm catching up on the last three chapters, and you certainly gave each appropriate titles.

You are really playing into my personal maid, schoolgirl, and forced feminization fantasies.

Will Philip be going by a more appropriately feminine name like Philippa?

I'm looking forward to the session with the beautician and the meeting with Head Mistress Tancred, in addition to the start of maid duty.

[Sandra B]

Chapter 8.  Makeover.

Sally Buttons of Buttons Beauticians arrived promptly at two.  Tina answered the door, and conducted her into the living room, where Philip was waiting, in a state of mild anxiety.  However, first impressions were favourable, on both sides.  Sally was a well-built lady, somewhere between youth and middle age, with a lot of curly blonde hair and a vivacious manner.  Her smile, enhanced by a lot of scarlet lipstick, and accompanied by a widening of her eyes, was infectious.  It was impossible not to return it.  Releasing the large wheeled suitcase she’d been pulling behind her, she shook Philip’s hand vigorously, and pushed him back into the armchair from which he had risen when she entered.
“Philip!  Pleased to make your acquaintance!  Your auntie’s told me such a lot about you.”
“Pleased to meet you too, Sally.  Though I really don’t know what you could expect to achieve…  I mean, I’m not sure what your remit is, to be honest….”
“Remit, darling?  I don’t ‘ave a remit,” she replied with a shrill laugh, “at least I don’t think so.  I’ll check when I get ‘ome!”
Philip felt a bit of a fool.  But Sally put him at his ease.
“Now your aunt says we can use the spare bedroom, so why don’t we go an’ ‘ave a little pow-wow.”
Tina showed them into the big downstairs bedroom, normally reserved for guests who had enjoyed themselves so much, it would have been imprudent for them to attempt the stairs.  Sally shut the door, and sat Philip down on the bed, seating herself beside him in a friendly manner and enveloping him with perfume.
“Now, Philip, I’m gonna level with you.  Your auntie tells me you’re gonna be dressed as a girl for the next few months.”
Philip opened his mouth to speak, but she silenced him with a wave of her hand.
“I don’t need to know the reason, so don’t tell me, please.  It’ll just confuse the issue.  As I understand it, you’re gonna need to look nice, without doing the whole girlie bit.  Right?”
He nodded, uncertainly.
“Okay.  First I need you to take off all your clothes,” she said, pulling on a pair of plastic gloves.  “Oh, don’t look so alarmed.  You can leave your underwear on, for the time being at least.”  Philip looked uncertain.  “Go on, then.”
Philip slowly removed his top, slipped the straps off his shoulders, and dropped his shorts.
“Ooh, nice panties!  I won’t need them off till at least next week.  And the stockings and shoes.  There.  Perfect.  Stand still.”
She stood up herself and walked around him several times.  Then she said, in an undertone, as if speaking to herself,  “yeah, well, nice legs.  We better sort them out first – bit of a giveaway.  The ‘air?…no, that won’t do.  Beard…at least it’s fair.  Can probably get away with that for the time being.  Eyebrows?  Definitely.  Has to be done.”  She was silent for a few seconds.
“You’re gonna be wearing a skirt, right?  So we need to get rid of the leg ‘air.  Good waxing will do it.  Won’t be fun, but there’s no alternative.  Arms are fairly smooth…  I’m gonna ‘ave to do something with yer eyebrows though.  Just pluck ‘em a bit today.  Maybe get rid of 'em later.  ‘Air.   This is a problem, Philip.  You’ve got a man’s ‘air.  Sort of wavy and a bit greasy.  The wigs you can get now are really amazing.  I could cover it up, but…  No, I would never be ‘appy doin’ that.  I’m afraid it’s got to go.”
“Got to go?” asked Philip, alarmed.
“Yep.  Shave it off.  Then a really nice wig, glued on.  Last for weeks before you need to do it again.   Let me see…”
She threw her case on the bed, opened it, and rummaged through it.  “’Ere we are.  This one’s perfect for your shape of face.  Let’s try it, shall we?”
She held up a wig cut in a short, page-boy style, in a light shade of brown, and arranged it on his head.  She turned him to face the mirror.
“Look at that!  Looks great on you.  But it’s too small with all that ‘air in the way.  Come on, sit down, and I’ll sort you out.”
Philip may have had some faint idea of protesting, but if he did it was quashed by Sally’s brusque, efficient manner, and soon he was seated in a bedroom chair with a towel over his shoulders and Sally working away relentlessly with the clippers.  As she worked she expounded her plans.
“So the beard will be okay for the time being if you shave properly every morning.  Next week I’ll have a go with the chemicals.”
“Chemicals?”
“Yes.  Not drugs, silly.  External.  Pity though.  I’ve a friend who could really work the oracle, if you would…”
“Not right now, thanks, Sally…” he put in, hurriedly
“Maybe I’ll talk to your aunt…”
“No!  I mean, I don’t think she really approves of…that sort of thing.  You know, drugs, and so on…”
“Well, we’ll see.  Your eyebrows are going to have a good plucking, and I’ll dye them a bit darker.  I’ll wax your legs, as I said, and finish them with a bit of depilatory.  Actually, I might chuck some on your arms at the same time.  The ‘airs are very light, but it will make a difference.  Next week I’ll do some of the other…areas.  You know, the more sensitive ones.”
Philip shivered.
“Now hold still while I shave your ‘ead,” she ordered, squirting foam onto the remaining stubble.”
In a matter of minutes, Philip was quite bald.  He looked at himself sideways in the mirror.  I look f***ing grotesque, he thought.  But not for long.  Sally dried him with a towel, then with a hairdryer.  She applied some sort of glue to his scalp, left it for two or three minutes, and then stretched on the wig, pressing it down all over until she was satisfied it was properly seated.  After another few minutes she worked her way around him, lifting the hair and rubbing off the excess glue with her finger.  Little rubbery balls of it fell onto his lap.  Finally she was satisfied.
“There.  What do you fink?”
He stared at himself in the mirror.  He was shocked.  He looked completely different.  Like someone else.  He could even have passed for female at a pinch.
“It really suits you.  You’ve got quite fine features.  Quite nice cheekbones.  And a smallish jaw.  Do you like it?  Imagine when you’ve got a bit of makeup as well.”
“It’s…interesting.  Such a difference…”
“Tina’s offered to take care of your makeup.  She knows what to do.  I did make a couple of suggestions.  Pale pink lipstick, definitely.  Reds would be too bright for your complexion.  But a bit of blusher.  You’ve got quite a fair skin.  And I did suggest a few freckles!  You’d look so sweet.  But then, no mascara.  Wouldn’t go.  But I’ll leave that to 'er.  The ‘air’s beautiful though.  Wait till she sees you!”

The remainder of the session was devoted to waxing – “don’t scream too loud, Philip – they’ll fink I’m torturing you” – to a manicure, to the endless plucking of his eyebrows, and the applications of depilatory cream.  By four thirty she was finished for the day.
“I can’t do any more this week.  But you’ll pass for a few days.”
“Thank you, Sally.  You’ve done a great job with some sub-standard material.”
“Not at all, darling!  You look smashin’!  ‘Ere, give us a smacker!”
And to his surprise, she placed an enthusiastic kiss on his lips.
After she’d left the room, Philip was left sitting there feeling slightly dazed, wearing his pink panties and nothing else.  He could hear the low buzz of conversation from the lounge,  interspersed with occasional peals of ribald laughter from Sally.  He occupied himself for some time by admiring his reflection.  Well, he thought, obviously this experience is something I would never have chosen myself, but I don’t have any choice, do I?  So I might as well go for it.  I mean, there’s no point complaining, is there?  I’d just make it worse for myself, and for mum...   Thoughtfully, he stroked his smooth, hairless thighs.  I wonder if Tina would like to practice with the makeup this evening?  I mean, I’d hate to have her mess it up in the morning when I have to go see that headteacher.  Maybe I should suggest it…
But he didn’t have to.  After he had dressed, he made his way gingerly back to the lounge.  Sally had left, and Aunt Estella and Tina were waiting expectantly for his appearance.  They seemed impressed by the transformation.
“Wow!  Philip!” exclaimed Tina.  “I love the hair!  You look completely different!  You could easily be…”  She didn’t finish her observation, but simply stared at him with a strange, fascinated expression on her face.
“Excellent,” said Aunt Estella, with a grim smile.  “Better than I could have hoped…  Tina, darling, why don’t you give him a little makeup, and then maybe he could try on his new school uniform.  I think Christabel is definitely going to be impressed!”

[sissyboy1212]

Great chapter. Can you ask Aunt Estella to book a personal appointment with Sally Buttons for me as well? Maybe she'd like two maids?

Love your story.

[Sissy Little Girl]

Sandra B, you are pushing all of the buttons; even Sally Buttons. Philip is finding out that being a girl requires lots of work to make yourself pretty.  That wig sounds like it is to die for and it is glued on.  I almost got a human hair wig that glued on; but, I chickened out.  Now Tina will get to do her work on Philip's makeup.  Another GREAT chapter.  I can't wait for the next one. 8) 8) 8) 8) 8) 8) 8) 8)

[Sandra B]

Chapter 9.  The Whole Shebang.

Philip followed Tina upstairs to the bedroom, and she laid out his uniform on the bed, all except the jacket, which she left on its hanger on the front of the wardrobe.   It was royal blue, with a red and gold school crest on the breast pocket.  The skirts were royal blue and light blue tartan.  There was a winter uniform and a summer uniform, the main difference being that the skirt of the former was fully-lined, pleated, and knee-length, whilst the other was half-lined, unpleated, and mid-thigh, and looked more like a little kilt.  He thanked his stars it was winter, and hoped it would stay cool until July.  There was a white blouse, and also an optional V-necked jersey in maroon wool for especially cold days.  The school tie had maroon and blue diagonal stripes, and the school scarf maroon and blue longitudinal stripes.  There was a choice of white socks or white tights, worn with black leather shoes of the usual school pattern.  Tina turned her attention to his makeup.  He sat in the chair in front of the dressing-table mirror, and she bent over him.  On went the slightest tinge of blusher, to make his pale skin look warmer, and, of course, she couldn’t resist the temptation to experiment with the freckle pencil Sally had left her.  Her black hair was down now – before she had had it tied back – and it hung a few inches from his face.  He could see the individual strands, quite coarse, and slightly wavy.  A vision of playing with her all those years ago flashed into his consciousness, of grabbing a handful of that strong, wiry hair, while they rolled about on the springy lawn in hysterical delight.  His gaze moved to her face, wonderingly, as if he expected to see the same girlish features.  She felt it, without shifting her attention from her task.
“What are you looking at?” she smiled, in a playful tone, which nevertheless conveyed her pleasure at his attention.  He lowered his eyes in mute admission.  It brought home to him his deepest feelings for her, which up to now had been largely unrealised.  He sighed faintly.
“In the morning I’ll do this again, and your nails, too.  Pink, like the lips.  Is that okay?”
She finished with a touch of pink lipstick – “gloss for you tomorrow, Philip.  You need to impress Miss Tancred” – and left him to dress.  He discarded his T-shirt and shorts, and considered the uniform.  He decided on the tights – it was cold, and in any case they seemed a bit more grown up.  Then on with the cool, slippery blouse, the winter skirt, which he fastened without fumbling, as if he did it every day, and then the tie.  He was smiling as he tied the tie.  He knew he always looked good in a tie.  That was, indeed, just about the farthest reach of his vanity, though it was hardly worthy of the name.  Finally, the jumper, which he pulled down loosely over the waistline of the skirt.   He slipped on the shiny black shoes, and, taking the jacket off the hanger and putting over his arm, headed downstairs again.
His entry left his aunt and Tina temporarily speechless.  Then his aunt said, with unusual warmth,
“Philip?  You look wonderful.  A real schoolgirl.  And a pretty one!”
“You do look incredible, Philip,” added Tina.  “Gorgeous, in fact!”
“Wasn’t I gorgeous before?” he joked, but feeling inwardly proud.
“Put on the jacket, dear.”
He slipped it on, and did up one button.  He stood there awkwardly, his arms by his side.  He missed having trouser pockets.  The skirt did have a little pocket, big enough for a few coins or a train ticket, but nothing he could thrust his hands into and look casual.  Nevertheless he was enjoying that strange feeling of being smartly dressed – something he hadn’t experienced for some time.
Aunt Estella looked at him critically.  The she allowed herself a rare little smile.
“You’ll do.  You can change back now.  Tina will need to make you up again in the morning, so you can forget your maid’s duties this once.  She’ll give us a lift to the school when she leaves for work.  We may be a bit early, but it won’t matter.  Christabel has said one of the teachers can show us round before the meeting.”
“Okay, aunt.  Thanks.” 
He made his way back upstairs.  He didn’t know why, but he had experienced a brief moment of pride at gaining his aunt’s approval.  Perhaps because generally it was so difficult to earn.  Nevertheless, the idea made him feel slightly uncomfortable.  He reminded himself of what she had done to his family, and what she was doing to him.  He was certainly not going to start colluding with her now.

He sat down at the dressing-table and looked at himself in the mirror.  This was ridiculous!  A few days ago things had been…normal.  All right, there were problems.  Big problems.  But now…  He shook his head in a gesture of mild irritation.
There was a soft knock at the door.
“Come in.”
It was Tina.
“Philip…hi.  Are you okay?”
“Yes.  Fine.  Why not?”
She slipped around the door, and closed it quietly behind her.
“Can we talk for a minute?”
“Course.  Sit down.”  She seated herself gracefully on the bed.  He turned to face her.
“I know this must be difficult for you….”
“Not really,” he said, offhand.  “Anyway, I don’t have a choice.”
“Well, no, I suppose not.  I just wanted to say…you know, I really admire how you’re dealing with this.  I mean, I know my mother can be…”
“A bit of a cow?"  he said. flippantly.  And then added, quickly, "no, I’m sorry, I didn’t mean that…”
“No, really, it’s all right.  I wouldn’t blame you if you did think that.  She can be very…demanding.”  She paused.  “I just wanted to say…well, I wanted to tell you how great I think you’ve been about all this.  I didn’t know what to expect when I heard you were coming to stay.  I mean, it had been such a long time.  But as soon as I saw you, it all came flooding back.  I feel like we’re already really good friends, and that we can be even better friends in the future…”
“I feel the same about you, Tina.  I should have told you, but I’ve been so distracted with…everything.”
“Of course…”
“You know, I had a bit of a thing about you, back then.  You’ve no idea how I used to look forward to coming over.  I was devastated when our mothers fell out.  I was pining for you for ages.  Even now…all those lost years…”
“I felt just the same, Philip.  And I want you to know, what you’re having to do now…it doesn’t make any difference to me.  In fact, I suppose I should confess something.  You know I’ve never had a boyfriend?  Not a proper boyfriend, anyway.”
“Your mum said something during the drive here…”
“I have had a girlfriend, though.”  Philip looked surprised.  “It was nothing, really.  I was sixteen.  She was eighteen.  A sort of crush.  But it made me realise…I’m probably not into men, that much.  Or so I thought, till I saw you in that uniform, with your hair and everything.  Suddenly I just wanted to hold you, to put my arms round you and hug you,  so much….  Is that terrible?  Or just stupid?”
Philip stared at her.  Something was happening inside his chest, something between pain and ecstasy.  He kept his cool, though.  He had rehearsed the romantic encounter in his fantasies, so he knew just what to do.  What he thought he should do, anyway.  He slipped off the chair and sat down beside her.  He took one of her hands in his.  He looked into her eyes.
“Neither, Tina.  Do you…  I mean, do you think you could…like me?”
“Oh, yes, Philip.  Very much.  You are just the sort of person  I could like…  I do like  – a guy who has no need to be all big and macho, but has real strength of character.  I may be wrong, but I think as you are now” - she drew her head back slightly to take him all in – “as you are now,  is much more like to the real you.  Do you think…that could be true?”   
“Oh, yes…yes, I think, maybe, it is…”
“You probably think I’m some sort of pervert, don’t you, liking you in women’s clothes?  I don’t blame you.  And it’s not fair to you…”
“No, no.  Tina.  I don’t think you’re a pervert.  Course not.  It doesn’t matter to me at all.  For you, I’d be happy to wear whatever you liked!  As a matter of fact, I think, I probably feel much happier dressed like this.  More…free.  Sort of, at peace.”  She looked at him dubiously.  “It’s true, I do!”
The doubt faded from her expression, melting into affection and pleasure.  “Do you really…?  That would be so…wonderful, Philip.”  She smiled.  “You’re so kind to me,”  she added, in a tone of what seemed genuine gratitude.  She returned his serious gaze, her eyes flitting from his eyes to his lips and back again.  She leant towards his face.  He had actually closed his eyes, waiting for their lips to connect, when there was a sharp rapping at the door.  Tina jumped up quickly.
“Tina?  What are you doing in there?  Let Philip get changed and come downstairs at once!  I need to discuss plans for the week.  Well?”
“Coming, mother!  I have to go, darling.  We’ll talk again.”  And she hurried out of the room.

Philip sat there dazed and blinking, his mind in a whirl.  He had been cheated of her kiss, but he wasn’t disappointed.  He felt honoured…blessed.  She’s so great!  So honest, and loving, and… warm!  And so pretty!  Her hair…  I never really thought…  Of course I’ll wear girls’ clothes, if that’s what she wants…  I’d dress up as a clown if she asked me to.  I mean, I’m gonna have to anyway for the next few months.  And in any case, I don’t mind it at all.  It’s sort of fun in a way.  Even a little thrilling…

Mother and daughter returned downstairs.  They went into the kitchen to make coffee and think about supper.  Strangely, all Aunt Estella’s frowning irritation seemed at once to have vanished, and been replaced by a faint smile of satisfaction; while Tina’s own agitation had also quite dissipated.  She even gave her mother a playful nudge as they jostled each other for the coffee jar.

[Sissy Little Girl]

Sandra B, That was a hot chapter.  Philip, in his new school uniform was making me feel all warm inside.  I wish it was me in that uniform and not Philip.  Tina is a flirt.  She likes Philip more now that he is dressed like a girl.  Keep these chapters up like this and you will light a fuse in me.
 ;D ;D ;D ;D ;D ;D ;D ;D ;D ;D