His Aunt Nicole

[Simonssister]

Chapter 35

After the announcement of the results of the dressage the top three returned to be presented with their certificates and rosettes.  Lavinia was still flushed, a smile of contentment on her face.  She had ended up in third place, but she got the biggest cheer from the crowd.  As the three trotted out of the ground, attendants ran in and began constructing the remaining obstacles for the showjumping, which was up next;  two fences had been left out to allow room for the dressage.  Miss Poole’s hand resumed its former place on his left thigh.  Her fingers gently caressed his skin, in a way that suggested she was imagining she had hold of his rigid member.
The showjumping didn’t help at all.  Pretty lady after pretty lady, so neatly got up, smart jackets, figure-hugging breeches, and worst of all, high, shiny boots.  No, there was no way his erection was going away anytime soon.  Miss Poole seemed to understand, glancing down with satisfaction every now and then, and gripping his bare leg a little more firmly.
“You’re going to have such fun at the committee meeting…” she breathed, as much to herself as to him.
As for Bobby himself, he was mulling the paradoxes of his sexuality.  First paradox: he found females desperately attractive, especially those wearing boots, but seemed unable to do anything – at least, anything conventional – about it.  His desire was so overwhelming, he literally became weak at the knees, and wanted to sink down and worship.  Only then did he feel comfortable and natural, and only then could he satisfy his urges.  And his aunts’ treatment of him had seemed to encourage this desire – no, not to encourage, but to help him realise it.  They understood him better than he did himself.  It was true!  He sighed.  Before all this he had imagined himself dating all sorts of girls, being a real jack-the-lad, but now he was realising his place was rather as a submissive, not a lover but a sort of amusing toy for any woman with the inclination.  Any desire to struggle against this was weakening by the day.  He was unsure as to whether it would be better to fight, or to give in and accept his fate.  Second paradox: related; he was a boy, a boy with very strong sexual feelings, yet when his aunts dressed him as a sissy, whether a girl-maid sissy or a boy sissy, he found it both exciting and…yes, natural.  He felt strangely elated by the feeling of soft latex against his skin, of sweet, juvenile pastel colours, of caressing fabrics…  He sighed.  How did they know he could be seduced by such things?  In the grip of his own natural submissiveness and sissy attire he became virtually helpless…  But not only that, not only did he enjoy the sensation, but he also always wanted to attract the attention of women, and such clothes immediately fulfilled that purpose.  So, third paradox: dressed up he was self-conscious, desperately embarrassed.  His cheeks and ears would burn, he would have terrible butterflies, he would even tremble and stammer – but a part of him, perhaps the dominant part, loved the fact he was the centre of attention!  He feared attention, yet longed for it at the same time!  It was tearing him apart.  That’s why he thought he might eventually lose the will to resist…  Oh, dear, what a mess he was!
He was at such a pitch of arousal for the rest of the day, wanting to ogle all the competitors, that at one point he felt he would have given anything for Miss Poole to take him in hand.  A single touch would have been enough to bring him to a climax.  Her hand touching or stroking his thigh was driving him crazy.  By the end of the show he was simply exhausted.  He had never seen so many beautiful glossy boots in one place.  As the girls accompanied him back to the car park, where his aunts were waiting, all he could think of was getting home and going to bed.
“Here he is,” smiled Sarah.  “Well Bobby, did you enjoy the show?”
“Thanks, girls,” added Lavinia, “thanks for taking him in hand today.  As you saw, he badly needs some proper training.  You’ll continue next weekend, then?”
“Certainly, miss,” grinned Jasmine.  “It was such good fun…”
“Cheer up, darling,” said Nicole.  “You look tired.  Let’s go home to Lavinia’s have something to eat, and then you can have a good sleep before tomorrow.”
“T-tomorrow…?”
“Yes – don’t you remember?  You’re going to be Wendy’s maid for the day.  Oh, and Clare’s too, of course.”
In the turmoil of the day, Bobby had forgotten all about that!  “B-but…”
“Oh, don’t worry, I’ve got a lovely new outfit ready for you at home.  If you’re good, you can have a sneak preview tonight!  Would you like that?  Wendy’s so looking forward to having you.  Yes, and Clare too, of course…”

[Simonssister]

Chapter 36.

Lavinia recovered the padlock key from Jasmine and released his arms.  He climbed into the back of the car and closed his eyes, while everyone said their goodbyes.  In the event, he fell asleep on the way home, woke up long enough to eat a plate of lasagne, then went to bed, pausing only to discard his bunny top and his bootees.  He dreamt of Magda, encased from head to toe in scarlet latex…
This suited Lavinia well, because she needed to have a private word with Wendy.  She changed her boots for a pair of black leather ankle boots, grabbed her bag, went round and knocked at her door.  Clare opened it, her face lighting up when she saw who it was.
“Lavinia!  Come in.”  She hesitated.  “Are we on for tomorrow, then…?”
“Absolutely.”
Clare was having a year off before university.  She had light brown hair cut in a short bob, and mischievous brown eyes.  She would have been a few inches shorter than Bobby, Lavinia noted, but he would be in no position to push her around, of that she was confident.  She did a little jump of joy.  “Yess!  That’s great.  Come through.  Mum’s in the lounge.”  She ushered Lavinia eagerly along the corridor.  “Mum?  It’s Lavinia!  We’re gonna get our boot boy!  Yippee!”
“Hi Lavinia!  How are you?”
“I’m well, thanks, Wendy.  Feeling pretty good today, actually.  Just thought I’d finalise arrangements for tomorrow.”
“Great!  We were wondering…”  She noticed her breeches, and did a double-take.  “Cool breeches…” she said, thoughtfully.  “Is that what you wear for the show…?”
“Yes.  Like them?  They do get me noticed…”
“Not surprised…”
Wendy was about Lavinia’s age.  She had straight, dark brown, shoulder-length hair, and the same naughty eyes as her daughter.  She and Lavinia moved in different circles – Wendy was some sort of manager for a media company – but she also had a wild side, and though the two had never really been anything more than neighbours, they saw the wickedness in each other and respected it.
“Coffee?”
“Please.”
“I’ll do it, mum.  How do you like it, Lavinia?”
“Warm, white and creamy.”
Clare grinned, and disappeared into the kitchen.
“So…he’s agreed, then.”
“No.  But he’ll be here.”
“Even better.  I like it when they’re a bit rebellious.”
“So do I, up to a point.  But when he c-ums all over my boots and then refuses to clean it off…
“What?”
“Yes – just that.  He was supposed to use it as polish, but he just took his pleasure and then checked out.  I won’t tolerate that, Wendy.”
“I shouldn’t think so!  I didn’t realise…”
“It won’t happen again, don’t worry.  My girls at Pitt’s Wood took him in hand this morning.  Taught him a proper lesson.  So if you could carry on the good work….  Don’t spare the rod…”
“Love to.  You can rely on us.  Especially Clare!  Actually I’ve invited a few friends around this afternoon too.  I thought it might help break down any resistance…”
“I can see you understand perfectly.  Thanks.  Tomorrow, though, I thought we’d go for the maid look.  He gets a bit too full of himself when he’s playing the boot boy – thinks he has super powers or something!  We have a lovely new uniform which Nicole got for him.  Nice little maid’s dress in Alice-blue satin, with a layer of crinoline to keep the skirt bouncy, a rounded white collar, and pretty little short puff sleeves with crisp white cuffs..  We’ll give him white tights and black patent leather pumps with ankle straps and medium block heels – not so he’ll be falling over all the time, but just so he has to take care when he walks and won’t be able to run – or run away!  The ones Nicole’s got have little padlocks at the back so he couldn’t even take them off if he wanted to.”
“Mmm.  Sounds good!”
“You must have guessed girls in boots are one of his weaknesses, but the other is rubber.  Oh, Clare…thank you.  Ah, the smell of coffee!  Where was I?  Oh yes, rubber.  There’s nothing like the feel and smell of latex to bring out his vulnerabilities.  Better than Kryptonite.  All his strength drains away.  I don’t know where it goes.  Into his little coc-k, it seems – that stays nice and firm while the rest of him turns to jelly!  Oh, Clare…sorry…” 
“That’s okay, Lavinia.  I need to hear this as well as mum, so I know how to handle him.”
“Yes, of course.  I sometimes forget you’re grown up now.  It seems only yesterday…”
Clare gave her a look. 
Ah, yes…  Well, you get the picture.  So we like to keep him in rubber pants, and tomorrow we have a nice pair to match his dress, as well as a pair of matching long gloves which will go right up almost to his puff sleeves.  The combination of the two should keep him in a state of desperate arousal all day, which will make your job a lot easier.  He’ll want to comfort himself I’m sure, but of course in front of you – and especially in front of your friends – he won’t be able to.”
“Oh, the poor little frustrated thing!” cried Clare, with laugh.  “Doesn’t he have a girlfriend, then?”
“He likes girls, all right, but I think he gets so embarrassed he finds it easier to let them take the lead – so they soon realise it’s more fun to have him as a plaything.”
“Ooh…yes, that suits me fine.  Especially with that nice firm little coc-k you mentioned…”
“Clare!  Behave yourself!  What about Damien?”
“Huh.  I don’t consider him a proper boyfriend.  I just use him when I want to go out and there’s no-one else.  I’m gonna dump him soon, anyway.  In any case, we’re only talking about Bobby as a plaything.  I can have a boyfriend and a plaything, can’t I?”
The women laughed.
“However,” said Lavinia, getting back to business, “in case he does give you any trouble, I’ve brought a few extra things.”  She rummaged in her bag.  “First of all, restraints.”  She produced two pairs of blue leather cuffs, each pair joined in a steel link.  “Wrist cuffs.  Strap his hands behind his back.  He won’t be able to reach the buckles, so no locks required.  Once they’re on you can also put on ankle cuffs if you wish.  Use the shoe locks to secure them if you think it’s necessary.  There's some fine chain, and padlocks too, in case you need it.  Then – I don’t know how you feel about this.”  She held up two steel staple plates.  These screw to the wall, one at neck height, one just below waist height.  Once they’re in place you can secure him by his collar and his wrist cuffs with a couple of simple screw-links.  If you want me to install them I’ll do it now.  I know the measurements.”
“Oh, yes please!  Right here, I think, on this wall between the two armchairs.  Yes, I would definitely feel more comfortable to know we can secure him properly if we need to.”
“Ooh, mum!  This is so exciting!   He’ll be, like, our prisoner!  Yes, let’s put him there before your friends come round.  Then they’ll be able to have a drink and do anything they want and he won’t be able to do a thing about it!”
“Okay.  I’ll do that in a minute.  Now I’ve also brought his collar.  Here.”  She handed it to Wendy.  It was made of heavy blue leather, about four centimetres wide.  On the front was a steel D-ring and a silver plate engraved with the name “Bobbi” in script, and on the back the buckle was equipped with another D-ring, and a vertical flange of leather about ten centimetres high with a loop at the top.
“Nice…”
“And if you need to silence him – and you probably will – here’s his ball-gag.  Pop that in his mouth, thread the strap through the loop at the back, and buckle it up firmly.  That’s guaranteed to keep him quiet.”
“Gosh, Lavinia, you’ve thought of everything…   And all colour matched, too,” said Wendy.
“Bags I put it on him!” cried Clare.
Lavinia laughed.  “There’s one more thing actually, Clare…”
“Yes?”
“How would you feel about Bobby becoming your slave?”
“What?  My…slave?”
“Just an idea me and the girls had.  We could just imagine you being his mistress, having him at your back and call twenty-four seven.  He would still be answerable to us, but you’re more his age, and you have a distinct aura of dominance.  You’d be able to use him whenever you needed, or whenever you were bored and needed a distraction.”
“Seriously?”
“Yes.  We’d make it “legal”.  Nicole’s his guardian, after all.  She can decide what happens to him.”
“You should, darling!” said Wendy.  “Your very own maid!”
“Well, look…  Here is a contract we’ve drawn up.  Nicole and his mum have officially signed him over to you, and Sarah and I have witnessed it.  It gives you full control.  We’ll also give you all the dirt we have on him so there’s no argument, but the contract may well convince him.  We’ll leave it to you.  Think about it, and if you want to go ahead, play it by ear, and take him for your own.  Then, any time you want some fun, you can summon him – maybe text him a code which will mean, “come now” and give him a location if you’re not at home.  You can work out the details, I’m sure.
“Wow…  Should I?”
“Go for it , darling!”
“Let us know.  You’ll find a training lead amongst the accessories.  Now…what else?  Let me think…   Oh, yes.  He’ll have a nice little white latex apron with frills.  A maid’s head-dress of course – simple plastic Alice-band with white latex frilling…  Maybe a garter, if I can find a suitable one…  Oh, and his pants.  Yes, his pants…  they’re also designed to keep him under control.  They have two retaining bands inside, one right at the base to keep his thing nice and firm, one half way up the shaft, to keep it nice and straight and vertical.”
Clare squealed.  “Oh my god!  I don’t believe it!”  She covered her mouth in excitement.
“Yes…  And in the back…well, there’s a discreet integral plug…  Well, hardly a plug.  A little rubber egg on a stalk which goes…inside, if you see what I mean.”
Chloe stared.  “A butt plug?  Rubber panties with a butt-plug?”
“Yes, Chloe.  It has a remotely-controlled vibrator powered by triple-A batteries housed in the stalk, so it can go for a long time if needed.  Here’s the controller – I may as well give it to you now…”  She handed it to Wendy.  “It’s small enough to go on your key-ring.  See?  Start…stop…each press make it vibrate more, and it shows on the display…one to ten, see?  You may need it as a last resort if he starts playing up.  It should have a salutary effect…”
“Goodness…  You really have thought of everything…”
Clare gaped at the controller.  “Mum…?  I think probably I should look after that…?”
“Hands off, Clare!  You naughty girl!  Do you really think I’d trust you with it?”
“Come on, mum!  I’m better at stuff like that than you…  You know, electronic stuff, Bluetooth and all that!   Why can’t I be in charge of the vibrator?”
“Well, we’ll see.  Don’t press me about it.”
“All I want to press is that button…” grinned Clare.
“Just be patient, darling.”
“But Wendy, just remember not to leave it going too long, or…”  She leant forward and whispered in her ear.
“What?” cried Clare.  “Lavinia?  What happens?”
“Shush, darling.  That was not for your ears,” frowned Wendy.
“Huh.  I can guess, anyway.”  She did an impression of a male climax.  “God, I can’t wait…  Lavinia, can we punish him if he misbehaves?  I mean properly punish him?”
“He’ll be your property.  Or at least, if our little plan works, he will be. So it’s up to you.  If you think he deserves it, why not?”
“Cos I still have that school cane I used when I dressed up as a teacher on Halloween…”
“Well, naughty boys sometimes need a good caning…  Don’t you agree, Wendy?”
“She’s terrible, isn’t she?” said Wendy, indulgently.
“I take after you, mum…”
“Okay,” said Lavinia.  “I think I’ve told you everything you need to know.  I’ll fit the wall staples, and then I’d better get back.  I’ll bring him at, say, nine tomorrow?”
“Make it eight, please, Lavinia.  I can’t wait to see our new maid…” pleaded Clare.  And after Lavinia had done her little bit of DIY, and Clare was showing her out, she added,
“I’m glad Bobby likes boots so much.  Mum bought me a pair for my birthday, and I’ve been looking for an opportunity to wear them.  I think hes gonna like them…”

[Simonssister]

Chapter 37

It was agreed Bobby would breakfast at Wendy’s, and Clare insisted he would serve breakfast.
“He needs to know his place right from the off,” she remarked, and added, “I just can’t wait to see him – I mean her – and to start teaching her her duties.  Don’t worry, Lavinia – if you allow us to have her regularly, we’ll train her so well you’ll be able to hire her out for money in a few weeks!  You’ll see!  I promise!”

When Nicole woke him Sunday morning, Bobby was still sleepy – though predictably his little friend was already as alert as the day before.
“Good morning, Bobby.  I see you’re looking forward to your day’s work, then.”
“What?  Oh, no.  For a moment, I’d forgotten.  Why do I have to go round there?  I don’t like either of them.  That girl’s scary…”
“Oh, you think all girls are scary!  She’s nice.  She not that much older than you.  You could even ask her out.  She’s pretty, too.”
“You’re joking, aunt.  I’m not interested in her,” said Bobby, who had been so embarrassed during his one previous meeting with Clare that he couldn’t even remember her face.  “Is she older?  She’s not very tall…”
“You’re tall for your age.  She’s average – well, maybe a bit below average.  But she’s nice-looking and smart.  I bet you get to like her.”
“No way!  She might fancy me, I guess, but in any case I could never go out with a girl who’s that much shorter than me.”
Nicole burst out laughing.  “What?  Whyever not?  What a silly thing to say!  What does that matter?”
Bobby frowned.  “Dunno.  It just does…”
“Well, we’ll see how you feel after you’ve spent the day with her.”
“Do I have to…?”
“Yes, you do!” came a voice from the doorway.  It was Lavinia.  “Now get up and get ready.  Go take a shower – and be quick about it.  You need to be there in…” - she checked her watch – “in forty minutes.”
Bobby didn’t ask exactly what he was going to be wearing – mainly because he wanted to avoid the matter as long as he could.  He soon found out, however, as his costume was laid out on his bed when he returned, wrapped in a towel.
“No….” he whined.
“I told you he’d whine as soon as he saw it,” nodded Lavinia.  “Better cut that out, or…”
He noticed her riding whip was lying on the bed next to his dress, so he resigned himself to his fate. 
His dressing was conducted with seriousness and efficiency, as if they were preparing a prince for his coronation.  Sarah came in to watch, and to record his glamourisation on her phone.  Both of the others had donned surgical gloves.  He knew what that meant.
“Pants on first,” ordered Nicole.  She held them up.  Fine, pale blue latex, a double-thickness waistband and reinforced elasticated leg holes, slightly thickened at the base of the anal plug.  “Step in.  Right, now bend forward…   Good boy.  Little squirt…  Not you, Bobby, the lube…  There.   That comfortable?”
“No!  It’s not! Why do I have to have this?  An’ it’s definitely bigger than the other one!”
“Maybe…a little.  But we’re having to retrain you, remember?  Because of your behaviour.  Now stand up straight and let Lavinia deal with the rest.”
He stood still for Lavinia’s part of the operation, keen to ensure everything was handled carefully.  The loops were made of fine, soft latex, each about three or four centimetres wide.  With the prospect of a difficult day ahead his erection had subsided somewhat, and with Nicole holding open the front of his panties she was able easily to position them.  She stretched the lower one open with the fingers of her right hand and used her left to feed his semi-tumescent member and his balls through the loop.  She slid her fingers out slowly, allowing it to gently tighten around the base.  Then she did the same with the upper loop, which gripped the shaft behind the head.  Bobby went to pull away, but Nicole held onto the waistband.
“Wait!  Don’t be so impatient.  We’re not finished.”
Lavinia picked up the tube of lubricant, squeezed a generous blob onto her fingertips, and smeared it on the tip..  Bobby was most indignant.
“What’s that for?  Do you have to do that?”
“Stop it from chafing in case it becomes dry,” said Nicole – knowing full well there wasn’t much chance of that.  Lavinia smoothed it on until she saw signs of returning arousal, then stripped off her gloves.  Nicole let go of the waistband.
“Ow!”
“Sorry.”
They got his tights on, with a single blue latex garter around his left thigh, and buckled and locked his shoes.
“Do I have to wear these?” he complained, gingerly trying a few steps.
“You’re a maid,” replied Nicole.  “This is what maids wear.”
On went the dress with its crisp skirt and elasticated waist – a modest length, just above the knee – and then the fine white latex apron over the top, apron, bib and shoulder straps trimmed with even finer filling .  While Lavinia tied his apron at the back, Nicole lightly powdered the insides of his light blue gloves, and while she pulled them on, making sure they fitted perfectly over his fingers and arms, and squeezing out any pockets of air, Lavinia carefully buckled on his stout leather collar.
“What’s that thing at the back?  Something’s rubbing against the back of my neck.”
“Nothing.  If you behave, it won’t be needed.”
All that remained was for Sarah to slide on the headpiece, and he was ready.  They still had ten minutes, but Lavinia guessed Wendy and especially Clare wouldn’t mind them being a few minutes early.  Sarah, as being the one least implicated in his transformation, played good aunt.  She kissed and reassured him, took his hand, and, much to his trepidation, led him out of the front door.  A few people stopped to stare, but they were soon at Wendy’s front door.  In response to their ring the door was flung open almost immediately, revealing a delighted Clare. She gasped.
“Bobby!  Er, I mean, Maid Bobbi…  Come in, please.  Mummy, they’re here!”  She ushered them down the hallway.  “Thank you for coming on time!  I’m sorry, I’ve been so excited.  Bobby, you look amazing!”
Despite his embarrassment, Bobby actually felt the faintest thrill of pride at that remark.  Stupid, maybe, but Clare was staring at him with what he took to be such an expression of admiration that he momentarily forgot he was dressed up as a maid in rubber apron, gloves and panties, and strutted as confidently as his shoes would allow after her!  And it was true now he looked at her properly – she was very pretty.  He might have been less full of himself if he had known that the expression he took for admiration was in fact simply the delight in being presented with a new toy which turned out to be even nicer than expected.
While the women had a coffee, Clare took Bobby by the hand and led him into the privacy of the kitchen, where she could give him a thorough examination without being observed.  She started at the top, standing on tiptoe and running her fingers through the ruffles on his latex headpiece.  She was wearing her favourite blue nail polish.
She examined his collar – “such good-quality leather!  Look, it’s the same colour as my nails!  And I love your little plaque, Maid Bobbi!” – tested the D-ring with her finger, stroked his silky latex gloves, plucked at his apron frills, felt the crisp, crinolined skirt – “oh, gosh!  I used to have a dress like this when I was twelve!” - caressed his silky white tights, tugged at his garter, and squatted down played with the little padlocks on his shoes.  Then, with an expression of undisguised glee, she stood up facing him, looked up into his face, and said, coolly,
“Can I have a peek at your panties?”
Bobby blinked, blushed and took a step back.  He bit his lip.  “I-I don’t think…” he began.
The smile faded from Clare’s face.  “Maid Bobbi!  Show me your panties!”
The buss of conversation next door stopped suddenly. Then there was a burst of laughter.
“Do what your mistress tells you, Bobby!” called Lavinia.  “Or I’ll tell her to put you over her knee and spank you!”
“Show me!”
Nervously he lifted his skirt a couple of inches, unconsciously crossing his thighs. 
“Higher.  Right up!”  She slapped his leg, hard.  It stung.  He sobbed, and hoisted it up.  Clare squatted down again, and pulled down the front of his tights.  He flinched.
“Stand still!”  She stared, and giggled.  “Bobbi, you have such cute panties.  And you fill them so nicely…”  She gently prodded each of his balls in turn, then ran her nail slowly up the engorged shaft to the bulge of the glans.  The lube had done its work, and he was again in his usual aroused state.  Clare explored the constriction below the head.  Oh, yes, I see…  This keeps it in place.  How clever.”  She pushed the head gently with one finger,, making it slip sideways and making Bobby gasp.   â€œWhat’s the matter?  Do you want to play with it?  You can if you want, so long as I get to watch…”
“And me!” called Wendy from the lounge.  “I want to see too!”
“No. mum – I think he’s too shy to do it at the moment.  It’s very big and hard, though, and it slides from side to side if I push it, so it must be very juicy.  It’ll have to pop sooner or later…”
“Well come and say goodbye you two.  Lavinia and her friends are about to leave.”
Clare dragged Bobby, frightened and flushed, back into the lounge.  Everyone  had risen from their chairs and his aunts were preparing to leave.  Bobby would have liked to beg them to take him with them, but he knew it would be to no avail.  They contributed to his confusion by insisting on kissing him goodbye, as if they were leaving forever.  His face was a picture.
“You will be back later?”
“Hmm,” said Nicole.  “Probably.  We’ll see.  Maybe we’ll leave you here if Wendy and Clare want to keep you…”
“Ooh, yes please,” said Wendy, enthusiastically.  “Or maybe we could lend him to one of my friends…”
They all laughed, while Bobby stood there helplessly looking seriously distressed.  But before he could think of what to say or do they had left, and he was alone with his new mistresses,,,

[Simonssister]

Chapter 38

Wendy smiled a smug smile and looked at Bobby.
“Well, darling, now don’t you look pretty?  But I think your aunties have forgotten something.  Don’t you agree, Clare?”
“Yes, mum.  They’ve sent him out without makeup.”
“Exactly.  If it were just us I wouldn’t care.  You’d be able to carry out your chores just as well without it.  But my friends will be over after lunch, and they’ll expect their maid to be perfect in every way.  So come and sit down and let us make you pretty.”
It didn’t take long.  Wendy plucked his eyebrows  and scrubbed his face, then allowed Clare to take over, while she went off to find some earrings.  Clare redrew his eyebrows, applied foundation, blusher, and some subtle blue eyeshadow, and finished off with peach lip gloss.  Wendy returned with a pair of silver screw-on earrings with dangly silver chains, and did them up so tight it made Bobby’s eyes water. 
“That’s better!  You look gorgeous, sweetie.  Now, clear the cups away, make us some breakfast, and while we’re eating you can wash up.  You can have yours when all the washing up is done and put away.”
“But…”
“No buts.  Get on, or I’ll have to punish you.  You’ll find a tray on the kitchen counter.  Take the cups out first, then cook us some pancakes.  I assume you don’t know how to make pancakes, so you’ll find a packet of ready-made ones next to the fridge.  Read the instructions.”
“Yes, and get me some orange juice,” added Clare.  It’s in the fridge.  And bring in the chocolate sauce.  Hurry up, please.  Don’t forget plates and forks.”
“She’s got a lot to learn,” sighed Wendy.
“Yes, mum, but if we have her regularly we can teach her.  If I punish her for every mistake, she’ll soon learn to take care.”
“Oh…  And how are you proposing to punish her exactly?”
Bobby had returned with plates and forks, and dumped them on the table with a sour look on his face.  Clare turned and slapped his leg as hard as she could.
“Ouch!  What was that for?”
“Put them out nicely, idiot!  Yes, and the forks by the side.  You’re a servant now, and you’d better learn to do things right.  Don’t you dare scowl like that!  Right.  I got a present for you.  I thought you might need it.  Go to the bottom drawer in the chest…  Yes, there.  Well, open it.  What do you see lying on top?”
Bobby hesitated.  “A…a cane?”
“A cane, what?”
“What?  Oh…a cane, er, miss Clare…”
“Good.  That’s better.  You’re learning.  Bring it here, maid.”
Nervously, he brought it over.
“Turn around.  Turn around!”
Smack!  Right across the backs of his calves.  Bobby yelped, jumped, and nearly fell.
“That’s what it’s for.  Understand?”  Clare had a vicious smile on her face.  “Understand?”
Bobby had tears in his eyes.  “Yes miss, yes, I understand.  Please, I have to go and cook the pancakes…”
“Yes, go.  Hurry up.  You’d better cook them properly, or…”
“I will, miss…”
Bobby retreated into the kitchen.  Clare placed the cane on the adjacent chair.
“You were serious about punishing him, I see.”
“Of course.  If we’re going to have a maid, she needs to learn her lessons.  Why don’t you give me that remote now?”
Wendy sighed.  “Well, you seem to enjoy being in charge.  Here, take it.  But use it sparingly.  Remember what Lavinia said…   Ah, here come our pancakes…”

[Simonssister]

Chapter 39

Fortunately for Bobby, he had cooked these pancakes many times before for himself, so they were perfectly done, not burnt as Clare had thought they might be.  Which she felt was a pity, since for such a misdemeanour a good caning would have been fully justified.  She was keen to establish her proprietorship early on – she really fancied the idea of having him as a slave.  Her experiences with boys so far had not been rewarding, and she felt that if she could  revenge herself on them as a whole she would feel a lot better.  This ambition was shared with several of her friends, who would only be too delighted to discover they had an oversexed and defenceless member of the species available for abuse.  But further opportunities for punishment and humiliation were soon to present themselves.
Clare had him stand behind her chair like a domestic whilst she ate, opposite her mother.
“So, Bobbi,” said Wendy, as she finished the last mouthful, “how are your other duties coming along?”
“O-other duties, miss?”
“Your boot cleaning duties.”
“Oh…that…”
“Yes, that.  Was your aunt Lavinia happy with your work Friday evening?”
“F-Friday?  Oh, yes…Friday.  Well, I, er…did my best, I hope…”
“Really?  I’m pleased to hear that.  I’m sure Lavinia will confirm your account…”
Bobby panicked.  “W-well, miss…to tell the truth…it wasn’t my greatest er, performance ever…  I’d rather you didn’t remind her…if that’s all right…”
“Oh, I see.  You’re too modest, I’m sure.  I think we’d better see for ourselves, don’t you, Clare?” she added, with a wink.
“That’s a good idea.  Bobbi?  You can clear the table now, and do the washing up.  Then I’ll test you to see what sort of boot boy you really are.  When you’ve done you’ll find the boot cleaning stuff in a wooden box in the cupboard next to the sink.  Bring it into the lounge.  I’ll go and get ready.”
The reason Clare hadn’t yet worn her new boots was that they were strictly club style, and she and her friends hadn’t gone clubbing for a few weeks now.  She went up to her bedroom, retrieved them from the bottom of the wardrobe, and lay them on the bed.  They’d been quite expensive, but then they were her first pair of grown-up boots, and they’d been custom-made.  And grown-up they undeniably were!  Thigh-length with a three-inch block heel, fine, smooth black leather lined with what looked like pinky-purple satin, with two lapped back zips, so zipped up they disappeared under soft leather flaps.  Each zip zipped from bottom to top, the lower one from the ankle to the crook of the knee, leaving the thigh section open at the back, and free at the front.  That had its own zip, which closed the top of the boot firmly around the lower thigh.  Both zips, once closed, were secured in place by a little flange that locked into the teeth.
She experienced a frisson of excitement as she ran her fingers over the silky leather.  “If these don’t do the trick, nothing will…” she murmured.  As to the nature of the “trick”, the little laugh which followed the statement suggested she had a plan.  But she was already preoccupied by what should accompany her footwear.  It didn’t take long to make a decision.  A sparkly blue spandex dress, stretchy and figure-hugging, long in the sleeves and short in the body, black fishnet tights, and silver satin panties.  She slipped her legs into the boots, and zipped them up to the knee.  She refreshed her makeup, applied a few dabs and squirts of her sexiest scent, slipped on a couple of cheap plastic bangles, and headed off downstairs.
Bobbi was standing obediently by an armchair, the box of boot-cleaning materials at his feet.  Wendy was relaxing opposite, in the other armchair, sipping a coffee, an expectant smile of her face.  When Clare walked into the room amidst a cloud of perfume, Bobby’s mouth fell open.  He gaped and his knees started to tremble.  Clare stopped and did a little pose.
“What do you think?  Like them?  Well?”
An inarticulate sound emerged from Bobby’s open mouth.  Then he started to stammer.
“I-I-I…v-very n-nice, yes…I mean…er…”
“Is that all you have to say?  Well, let’s get on.  First of all, come here and do my thigh zips.  Come on!  Don’t just stand there like you’ve wet your knickers!”
Bobby collected himself.  He approached Clare, who simply lowered her eyes, indicating he should kneel.  He dropped to his knees, she gave a quick smile of satisfaction, then spun round.
“Zip them up, then.  And make sure you press in the pulls till they click, and make sure the flaps are properly closed and neat.  Understand?”
“Y-yes, miss…”
The zips were heavy-duty and quite stiff.  He had to place his left hand against Clare’s knee while he pulled up first one and then the other, until the flaps closed firmly around Clare’s thigh. His rubber glove adhered to the leather.  Being made-to-measure, the boots fitted her legs, which were slim but strong, like the rind on an orange.  He clicked in the pulls and smoothed the flaps so the zips disappeared under the leather.  His face was inches from her thigh.  He caught a glimpse of her silver panties under the hem or her dress.  His heart began to pound.  He was breathing heavily.
“Goodness, what a fuss.  Now…”
She left him kneeling there and took her seat in the armchair.
“Right, now…  What are you doing?  Come here idiot!  For goodness’ sake…servants these days…”
“She’s inexperienced,” smiled Wendy, enjoying every second.  “Give her a few weeks…”
“Pass me my cane, mum.  Thanks.”
Bobby had scrambled to his feet, and was standing in front of her, about to kneel again.
“Wait!”  She ran the cane up and down his leg, and gave his calf a little flick, making him jump and squeal.  She smiled.  She was realising how much she enjoyed using it.
“Lift up your skirt!”
“Lift up your skirt!”
Nervously he took hold of the hem and raised it.
“Higher.” 
She contemplated the bulge under his tights.  It looked uncomfortably, satisfactorily swollen, like a well-filled sausage.  The retaining loop was doing its job, holding it firm and keeping it erect.  She ran the tip of the cane up it from his balls to the head, making him flinch.  She prodded it a couple of times, enjoying his fearful whimpers.
“Good.  Now down on your knees.  See that black tube with the sponge?  That’s the cream for my boots.  Do the left one first,  Don’t miss any part.  Then the right one.  Then go back and polish them with those cloths.  Get it?”
“Yes, miss!”  Bobby fumbled with the tube, eliciting an impatient sigh from his mistress, but eventually calmed down enough to start applying the cream.  He was really very meticulous, and despite his fluttering heart he even managed to work around the top of Clare’s boots without getting a speck on he tights.  For the backs she obligingly stood up and bent forward with her hands on the back of the chair, presenting him with a perfect view of her panties, which he was forced to ignore with clenched teeth, for fear of losing his cool altogether.
The polishing process was a lot easier.  The smooth areas, the pointed toes, the heels and the legs, he could simply polish with a cloth until they glowed with a soft sheen.  The scent of new leather filled his nostrils and made his coc-k throb and ooze.  The slight wrinkles around the ankles he brushed gently first, and for the stitching around the soles he first used a special little fine wire brush.  Eventually he leaned back, cheeks and ears burning, shaking with relieved concentration.  Clare smiled down on him.
“Good girl…  I’m really impressed…”  She winked at Wendy.  “Mum..?  Do you have the…you know…”
Wendy reached down beside her chair, picked up a short blue leather leash, and tossed it to her daughter.  Clare caught it, clipped the end to Bobby’s collar, and wound the other end around her hand.  Then she slowly pulled her towards her, until his knees were up against the base of the armchair, his chin was resting on the armchair seat between her thighs, and the head of his bursting pen-is was pressed hard against the tight waistband of his panties, and beginning to force its way between it and his slippery tummy.  She closed her thighs so that his face was trapped between the tops of her boots.  He found himself staring straight up her skirt.
“Do you like that?”
Bobby’s only reply was to start choking.  Clare gave a couple of salutary tugs on his leash.
“Stop that.  Take your eyes off my panties and look at me.  Now, I have a question for you.  Think carefully before you answer.  Do you like being my maid and my boot boy?”
“Y-yes, miss,” answered Bobby, unhesitatingly, desperate to be released, since the head of his coc-k had now slipped out of his panties, and was digging into his navel and dribbling juice down the front of his tights.
“Don’t feel pressured.  I won’t be angry if you say no.”
“No, miss.  I really do!” 
Clare was breathtakingly pretty, especially in those amazing boots.  At that moment, despite his discomfort, he really would have done anything for her.
“Right…  So, would you like to have me as your mistress…permanently?”
He stared up at her – as much as he could, with his head locked between her thighs.  What was she suggesting?
“P-permanently…”
“Yes.  Full-time.  I mean, you wouldn’t be required to attend me full-time, but you’d always be at my disposal.  And you’d have to be loyal to me, above all others – including your aunts.”
“But…  But they’d never agree.  They’d never…”
“They already have.  Mum?  Show him the contract.”
Wendy rose from her chair, took a sheet of paper from the dresser, and squatted down beside him.
“I’ll read it to you.”
“Thanks mum.”
“Right.  Here we go.  “I, Rosemary Tucker, and my sister Nicole etc. etc. of number twelve etc etc. hereby qualify our guardianship of our son and nephew, Bobby Tucker, in accordance with the following provisions.  Whereas our close friend Lavinia’s close and trusted friends Wendy and Clare Hunter have undertaken temporary custody of the said Bobby Tucker, and whereas the said Clare Hunter has expressed an interest in adopting Bobby in the relationship as mistress and servant, and whereas we regard Clare as a person well-qualified to take charge of and instruct Bobby in all aspects of behaviour and all duties of boot boy and maid, we hereby cede to Clare on her subscribing below in the place indicated primary guardianship and control of Bobby either until she shall withdraw from same or until we are minded to cancel this deed.”  It’s dated and signed by your mother and Nicole, and counter-signed by Lavinia and Sarah.  There are two blank spaces left, one for Clare and one for you.  So Bobby, Clare is ready to sign, and you need to think very carefully about whether you want to do the same.”
Clare opened her legs slightly and let out a few inches of leash.  Bobby drew back slightly, and gave a sigh of relief as his coc-k slipped back inside his panties.  The decision was an easy one.  He realised he fancied Clare desperately, and this agreement would allow him to spend more time with her.  He felt confident that once she got to know him she would be a lot more affectionate.  Who knows, he could end up being, not her slave, but her boyfriend!  Then he’d make her wear her boots every time they dated!  And he’d also liberate himself from the three aunts – so in his deluded state he thought – and no longer have to fear humiliation at the hands of those horrid stable girls!  So Wendy found a pen, Clare signed, and he signed, and it was done.  As he handed the paper back to Wendy, he looked at Clare with a propitiating and hopeful smile.  But as he saw the gleam in her eyes, it faded, and he became uncertain.
“Er, Miss Clare…what will my duties be..,.?”
She regarded him with a look of detached indifference.  “Your duties?  There’s only one, really.  Obedience, total obedience, humble obedience.  In case you forget…  Turn around.”
“Wh…?”  He was about to query the instruction, but her expression stopped him.  She put a hand on his shoulder and turned him round.
“Hold up your skirt.”
His hesitation was momentary.  Then, crack!  A single hard stroke of the cane across his bottom, eliciting a yelp of pain.  He swung round, eyes filling with tears.  Clare laughed.
“Now do you get it?  Right.  We need to prepare for the rest of the day.  Mum?  Restraints, I think.”
Wendy was folding up the contract, which she locked in a drawer.
“Yes, darling.”
It dawned upon him he had made a terrible mistake.  But it was too late.

That evening, after the party, (which will be described in a succeeding chapter), was over, Wendy, who had been reading a lot of Edgar Allen Poe recently, wrote the following pastiche.




As he knelt there on the floor,
Wond’ring what she had in store,
Contemplating dash for door –
Quoth the maiden, “Nevermore”.

Her hand felt like a tiger’s claw.
Fear at his vitals ‘gan to gnaw,
Would she his freedom e’er restore?
Quoth the maiden, “Nevermore”.

Never had he felt before
Like a woman’s helpless whore.
She would free him, he was sure.
Quoth the maiden, “Nevermore”.

“You cannot, Clare, my pleas ignore –
My pledge has not the force of law -
Let me my promise now withdraw –”
Quoth the maiden, “Nevermore”.

At last he understood the score –
He gan to weep, to weep full sore,
To plead, to beg, and to implore –
Laughed the maiden, “Nevermore”.

“Now you’re mine, both flesh and core,
Well or sick, rich or poor,
Like a serf in days of yore,
You’re my slave, for ever more!”

[ace]

Great update simon's sister, who'd have thought Edgar Allen Poe would be getting a mention on Betty's site .... ;-)

[Simonssister]

Chapter 40

They were about to put on his cuffs when there was a ring at the bell. 
“Who’s that?  I said not before twelve.  I’ll go…”
“Mum!  No.  Wait a second.”
She walked quickly to one of the front windows and peeped out.
“fuc-k!  It’s fuc-king Damien!”  A moment’s hesitation.  “Bobby – you go.  Don’t get talking – pretend you don’t speak English, or something.  Quickly now!”
Bobby, not entirely sorry to have had his bondage delayed, made his way nervously to the door.  He opened it, but not too wide.  Clare and Wendy watched from the lounge door.
A young man in glasses, stocky, with a slightly irritated expression on his face.  Jeans and leather jacket.  Faint air of self-importance.  He peered at Bobby, puzzled, and looked around as if to check he was in the right place.
“I want to see Clare.  Who are you?” he added, rudely.
“I-I, er, new maid…” answered Bobby, with an unidentifiable eastern European accent.
“Maid?  They’ve got a maid now?  Ha!  Haha!”
He stared at her, and pushed the door open further so he could get a better look.  He blinked.  He seemed to have forgotten about Clare for the moment.
“How long have you been their maid, darling?”
“Er, long …?”  As if he didn’t understand.
“Never mind.  What’s your name, sweetie?”  He was looking her over now, like a farmer inspecting a prospective purchase of livestock.
Here Bobby heard a suppressed snort of laughter from the area of the lounge door.  He lowered his head shyly.
“Bobbi, sir…”
“Bobbi?  That’s cute.  Please tell Clare – I mean,” (with a leer), “your mistress…that Damien Stern is here to see her…”
Bobby, uncertain what to do next, left the door ajar and hurried as fast as his heels would allow him back to the lounge.  Damien took the opportunity to stick his head inside and observe her retreat, which he did with a smug smile.
To his surprise Bobby found both Wendy and Clare lying on the ground apparently helpless with silent mirth.  He approached Clare.
“Clare!  It’s that guy.  Damien something…”
“Oh, god…  I know.  Shit, you’ve left the twat there with the door open…”
She was scrambling to her feet when “the twat” in question appeared in the doorway.
“Oh…Damien!  I wasn’t expecting you…  Mum, it’s Damien…”
Wendy had just managed to get to her knees.
“Damien…  Hi…”
“Why are you both down there…?”
“We, er, dropped some, er…
“Yes,” interrupted Wendy, seeing Clare lost for ideas, “we dropped some er, curtain hooks.  Need to clean the kitchen curtains…  How nice to see you…”
“Well, I came because Clare was supposed to ring me.”  He turned to her.  “Why haven’t you?  We discussed going to the club last night.  I didn’t hear a word, so…”
“I’m really sorry, Damien.  I’ve been distracted with…oh, yes, with our new maid.  She needs to be told so many things…so many…she’s new, you see, and…”
“Yes, I gathered that much.  I had no idea you were getting a maid…”
“Well, we may not…  I mean, it’s just a trial, sort of thing.  Friend of a daughter – I mean, daughter of a friend, who needs to make a bit of extra cash to…er, to pay for her, er…”
“Tuition,” blurted Wendy.  “Yes, music tuition.  She learning the pian…”
“Violin!”  interrupted Clare.  “And piano.  Very musical er…girl.”
They lapsed into an awkward silence.
Damien turned to Bobby, who had retreated into a corner and was standing, hands clasped in front of him, head slightly bowed, as he supposed maids were supposed to stand when awaiting instructions.
“Well, er, Bobbi, is it?  Nice to meet you.  That’s a very…pretty outfit.  Quite, er traditional, if I may say so,” he added, portentously.  He squinted at her latex-clad arms.   â€œI like your gloves…very good in the kitchen, I’m sure.”
Bobby, not knowing what else he should do, attempted a curtsey.  He flashed a look at Clare, appealing for help, but none was forthcoming.  She was more interested to see how things developed.
“Oh, don’t be shy, dear.”  Damien took a step closer, and then, yes, he actually took Bobby by the chin, and lifted his head, for all the world like an eighteenth century landowner patronising one of his female servants with a view to a little bit of casual sex!  That was exactly what Clare hated about him.  She hadn’t seen it at the beginning.  Pompous, privileged – son of an equally pompous barrister – misogynistic, and condescending.  He obviously fancied Bobbi, and knowing him, he had filed her away for a future peccadillo.   Perfect.  Well, fuc-k him.  What a great parting present this could be.
“I’m really sorry, Damien.  Mum’s having a party in an hour or so, and we really have to get ready, and Bobbi needs to know what she’s doing.  Can I ring you in the week?  I’m so sorry I didn’t explain, but…”
Damien waved her apology airily aside.
“No probs, Clare.  At least I got to see you…and the very pretty addition to your household,” he added, bestowing a seductive leer upon Bobby.  “I shall depart, then…”
Clare took Bobby by the hand.  “Please see mister Stern out, Bobbi…and play up to him, all right,?” she whispered in his ear.
Bobby led Damien down the corridor.  He seemed in no hurry.  At the door he turned…
“You know, I’m very impressed.  If you don’t end up as a full-time maid here, well…  I believe my family may well have a position vacant…  Here, let me give you my card…  Would you ring me…?  Would you?  In the next day or so?  Promise?”
“P-promise…?”  He looked up at him with big, frightened eyes.
“Yes.  This week, yes?”  He made a phone sign with his hand.  “Good girl.  I’m sure we can do something for you…”

When Bobby returned to the lounge something unexpected happened, albeit something very brief, which made all the bad things that day pale into insignificance.  Clare took him in her arms, hugged him, and gave him a good, hard kiss on the lips.
“fuc-king brilliant, Bobby.  I fuc-king love you!  Give me that card.  What’s this…”Legal Assistant”.  Yeah right.  Cleans his old man’s shoes.”  She turned to Wendy.  “What a wanker!  I’ll have him by the balls, mum, I will, with luck!  Anyway, fuc-k him.  Let’s get ready.  Bobbi?  Help me with the table.  Mum’s friends will be here soon.”