His Aunt Nicole

[Simonssister]

Chapter 41

Bobby was still in shock, but he quickly recovered, eager to be of service.  That one kiss had taken away any self-consciousness at a stroke.  It was something he could never have dreamed of had he not been cast in the role of Clare’s maid.  Suddenly the uniform and the makeup had ceased to be an embarrassment and instead had proved an asset.  Actually, he reflected subconsciously, he loved the feel of the crisp dress, the fine tights, the clumpy shoes…and especially those beautiful long latex gloves.  Maybe he himself was, well, if not actually pretty, at least feminine – that boy had thought so, after all.
“Mum?  Why don’t you go change.  Bobbi and I will get the table ready.  Take your time.  They won’t be here for at least an hour.  What are you going to wear?”
“Oh, I think just my new white top with black pants and boots.  Nothing fancy.”
“I thought now that we have a maid…”
“Well I don’t need to put on airs.  I will make sure to show them I know how to treat a servant though – so Bobbi, make sure you jump when I tell you to do something, understand.”
“Oh…  Yes miss.  Of course, miss.”
“Good girl.  All right, Clare, I’ll leave the preparations to you.”
The dining table was stowed away in a corner next to the big windows which overlooked the garden.  They carried it into the middle of the room.  Then Clare beckoned Bobby to follow her into the kitchen.
“You need to lay five places.  Mum has three friends coming, Steph, Sam and Lydia.  Mum will sit at the end.  I’ll sort out where the others sit.  Now, for each person, place mat, two knives, two forks, soup spoon and desert spoon.  Put out side plates, two glasses for now – white wine and tumblers for water.  I’ll show you the glasses for red and for bubbly later, though you probably know all that…”
“I know most things, miss.  I often wait on my aunts, whether I’m being a maid or not.”
“Good.  Nice to hear you sounding confident.  So lay the table first, and then we’ll talk about your duties.  While you’re doing that I’ll give Lavinia a call to tell her the good news.”

Bobby got to work.  He no longer had any illusions about Clare, nor about his position in the household.  It had all happened very suddenly, but he understood clearly that his absolute cooperation was required.  For the time being at least he decided he would play the roles expected of him.  The risk of character assassination was too real and plausible to ignore, and the more people that were allowed to share his secrets the greater the danger.  So for the time being he'd do his best.  If he pleased his mistresses he hoped that ultimately he would gain his freedom again. 
Clare went upstairs to her room to make the call.  She dialled Lavinia’s number.
“Hi Lavinia.  He signed.  Yes, isn’t it?  And so far he seems quite willing, rather to my surprise.  At this very moment he’s laying the table for lunch.”…(pause)  “Well I haven’t thought it through.  I mean, it’s still sinking in.  But something very funny happened, I have to tell you.  You know Damien?  Yeah, him.  That’s right.  Him.  He came round, unexpectedly.  We made Bobby – I mean Maid Bobbi – answer the door.  And guess what?  He hit on her!  I’m not joking.  He even gave her his number and made her promise to ring him so he can, what did he say?  Oh, yeah, so he can “do something” for her.  I know what that means.  Bastard!  Well, we’d done her makeup and everything – she really looked the part.  I know…isn’t it?  Don’t worry, I will.  I haven’t thought it through yet, but I’m gonna make such a fool of him, an even bigger one than he already is!  Yeah, course, tell them.  They’d appreciate the joke…”(pause)   â€śNext Saturday?  No, not particularly, why?  Oh, I see.  The same girls he saw yesterday?  No problem…course not.  Yeah?  What did they do?”...(pause)   â€śWhat?  Really?  Really?”  She let out a little scream of laugher.  “Are you serious?   He actually did that?  Every drop?  Oh my god that’s so…  A video?  Send it to me, will you?  I have to see that!  Great!  And listen, Lavinia, let me take him there on Saturday, okay?  Yeah, I need to meet these girls. Yes, absolutely.  Oh, thanks, got it.  I’ll save it for later.  It can go on the flash drive with the others.  I’m starting a collection.  You do?  I know, it is…but it’s fun.  Look, I have to go – mum’s friends will be here in a while and I need make sure the maid knows what to do.  Speak soon, Lavinia.  Bye for now…bye.”
Her eyes were sparkling as she returned to the lounge.  She didn’t, however, let on to Bobby what Lavinia had told her.  Today was all about his new job as the housemaid.  Wendy’s friends had been surprised to receive invitations to lunch and dinner at such short notice, but when they asked what the occasion was, she had simply replied with, “Oh, nothing special – just a few drinks and some good conversation”.
Bobby had laid the table quite as instructed.
“Let me see…  Excellent, Bobbi.  Now, you’ll serve the guests – right side, remember.  Just bring what I tell you to, and mum will tell you which wine to open.  They’re all lined up in the fridge.  Open the bottles in the kitchen, hold them in a napkin to serve, and remember just to half fill the glass.  When you’re not required, stand quietly to one side…  Look, about here, so if you need to go into the kitchen you won’t disturb the table.  Hold your hands neatly at the waist, so…  Lower your eyes.  Always reply with a “madam” or a miss.  You can call me miss.  Be very, very polite.  Try not to spill anything.  Don’t be nervous.  I won’t punish you too severely on your first day.  Okay?”
“Yes miss.”
“Good.  Now let’s have a look at you.  Try and keep your apron straight if you can.  And what’s with these tights?”
“They keep slipping down, miss.”
“They look a mess.  Let’s get them off.  Here, I’ll do your shoes…”
So the tights were discarded.  Clare locked on his pumps again.
“That’s better.  I notice you’ve cooled own a bit.  Just as well.  Try to keep that little thing of your from getting too playful, won’t you?  I don’t want him to distract you from your duties…”
“I’ll try, miss…”
“Good girl.  Now, what else…  Ah, yes.  I don’t expect you to be able to curtsey, though I’m going to teach you, but you can do a little bow.  Try one…   Not bad…  Just from the waist, lean forward about twenty degrees, then back…  That’s it.  Good.”
“Miss…?  What are Miss Wendy’s friends like…?”
“Oh, they’re all nice…easy going and friendly.  You’ll see, anyway.  But be prepared.  They’re bound to bombard you with questions.”
“Oh.”
“Of course!  They have no idea we have a maid.  But I’m sure you’ll charm the pants off them.”
Bobby looked alarmed.
“Yes - maybe literally!” added Clare, with a raise of the eyebrows.

Wendy had just descended to the foot of the stairs when the doorbell rang.  She peeped out of the window, and went to open the door.
“Mum!  No.  Use the maid.  That’s what she’s for.”
“Of course, dear. Sorry.  I haven’t got used to it yet.  It’s Sam.”
“Bobbi – answer the door.  Quickly – don’t keep her waiting.”
Bobby hurried to the door, opened it, and smiled.
“Good morning, madam.  Can I help you?”
Sam – a woman in her mid-thirties with long, straight, dyed-blonde hair, black wet-look leggings, black ankle boots and a tight black jumper, looked at him blank-faced, opened her mouth, and managed to say, “pardon”?
“Can I help you?”  He opened the door wider.  “Have you come to see miss Wendy?”
“Yes…  Who are you, sweetie?”
“I’m maid Bobbi.  Please come in.”
She entered sideways, partly to accommodate a large pink carrier and a hefty black handbag with gold accessories on a gold chain, partly to facilitate a closer examination of this unexpected personage.  Wendy greeted her from the lounge door.
“Sam!  Thanks so much for coming at such short notice!  Come through.”  They embraced and kissed.  “How was your drive?”
“Oh, fine, fine, thanks, Wendy.  Clare, darling!  How nice to see you!”  Another embrace, several more loud kisses.  “But…  “  She lowered her voice.  “For a moment I thought I must have come to the wrong house.  You have a maid?  What’s going on?”
“Bobbi’s mine,” grinned Clare.  “I am her official guardian.”
“You employ a maid, Clare?”
“No, Sam – I own her!  She’s mine.  She’s contracted to me as an unpaid servant, through her official guardian, who needed someone to take her on as a domestic.  It only happened today.”
“Is that possible…?”
“Bobbi?  Come here and let me introduce you.  This is Sam.  Sam, Bobbi.”
“Pleased to meet you, madam…”  He did a little bow, as he had been tutored.  Any nervousness he had felt had largely evaporated, and being the centre of attention was resuscitating his erection, which had started to swell again and press against his tummy.
“And to meet you, Bobbi….”  She looked at him closely, and then, with widening eyes, at Clare.
“It’s a boy…?” she mouthed, silently.
“Yes,” laughed Clare. “sometimes.  But at the moment he’s our maid Bobbi.”
“Oh…!” cried Sam, “now it makes sense!  But Bobbi, you’re very pretty, darling.  And your outfit!  Gorgeous!  Do you like having Clare as your mistress?  I bet you do.”
Bobby lapped it up.  Compliments always made him hard.  “Yes, madam, very much.  I hope I can be useful to Miss Clare and miss Wendy, though I’m very inexperienced  as yet…”
“Oh my god, he’s so…  Sorry, I mean, she’s so sweet!”  She kissed him on the cheek, and gave him an affectionate hug.  He heard her little gasp of surprise as his bloated coc-k became sandwiched between their bodies.  She held him just a moment or two longer than would have been appropriate, probably distracted by the shock.
“Goodness…yes…so charming…”  She hesitated, awkwardly.
“Are you all right, Sam?” enquired Wendy.
“Oh, yes, thank you…just a little faint, perhaps,  Quite warm, today.  I’ll just sit down, if that’s…”
“Oh, please.  Sorry, I should have offered you a seat.  Bobbi, get Sam a drink, would you?  Your usual?  I’ve got a fan upstairs somewhere - I’ll just go and find it…”  She hurried off upstairs.
“Thank you…” called Sam after her, weakly.
“Gin and tonic, Bobbi,” said Clare.  “Plenty if ice.  Lemons are in the fruit bowl.  Good girl.”
Bobby was back within two minutes, the glass on a tray.  He stood next to her chair and bent slightly forwards.
“Your drink, madam…”
“Thank you Bobbi…”   Sam took the glass, and placed it on the table to her left.  She turned back, and found herself staring at Bobbi’s bare legs, disappearing under the neatly-stitched hem of his swaying skirt.  Flustered, she blurted, “such a pretty dress!”  Clare seized her chance.
“Isn’t it?  Let me show you what lovely material it is.  Here.”  She positioned herself behind Bobby, so he couldn’t back away from Sam’s chair.  She put her arms round him from behind, so that he had to clutch the tray to his chest, then took hold of the hem of his dress and lifted it slightly as if to show Sam.  “Feel it, Sam…”
“Sam took it in her fingers.  “Oh, such good quality…”
“And there’s one layer of crinoline to keep it light and bouncy…  See?”
She lifted his skirt right up, presenting Sam with a perfect view of his panties.  Within inches of Sam’s nose, Bobby’s tumescent pen-is stood there, straining against its confinement.  The fine, translucent latex was moulded to the shape of his erection; the central band holding the shaft vertical was clearly visible, and the bulging glans with its cleft perfectly outlined.  Seeing Sam’s eyes widen, Bobby squirmed with embarrassment, compressing his thighs and shifting his weight from one foot to the other, which only served to make it slip and slide about against his tummy. 
He was gripping the tray tightly now, and his ears were turning red, but Clare had no mercy. She whispered in his ear.
“Bobbi – here, take your skirt – quickly now.  Hold it right up for Sam and don’t move.”
Obediently, Bobby took the sides of the hem, allowing the tray to lodge between his skirt and his chest.
“Don’t move, right?”
He nodded slowly.  His face was a picture.  The prim, smiling little maid was no more.  His cheeks were burning, his eyes tearful, and his head turned to one side, unable to face the lady whose respect he had hoped to earn.  Clare squatted down by Sam’s knees, and smiled cheekily up at her.
“What do you think?  Beautiful, isn’t it?”
Sam had overcome her initial confusion, and was enjoying the game. “It’s lovely, Clare.  Really very impressive.  Does it often get like this?”
“All the time.  Any excuse.  Watch.”
She extended a finger and gave the head a little push sideways.  Little bubbles chased each other about under the latex.
“Gosh!” exclaimed Sam.
“See how juicy it gets?   Have a go.”
“Can I?”
“Of course.  He’s yours too, today.”
Sam gingerly used a finger to push it back.  The bubbles retraced their course.  Bobby pressed his thighs together even more firmly, but the only effect it had was that his coc-k seemed to quiver, and pushed itself a little further up his tummy.  She gasped, and giggled hysterically.  Bobby emitted a faint whimper. 
“We have to be careful,” grinned Clare.  “It wouldn’t take much….”
They laughed, but Sam seemed unable to take her eyes off it.  Her cheeks were flushed, and she licked her lips thoughtfully.
“Is it difficult for you, Bobbi?  I mean, when it gets…like this?” she asked, without looking up.
“What?  No!” he blurted, sulkily.  He was feeling thoroughly humiliated.
“Don’t be rude!” cried Clare, giving him a slap on the leg. 
“Oh, it’s all right, Clare,” smiled Sam.  “It’s not his fault he’s got such an unruly one.  I don’t know how he keeps his hands off it, to be honest…”  She sighed, and bit her lower lip absent-mindedly.
At that moment Wendy returned, holding the fan.  Bobby felt relieved, and wondered if she’d tell them off.
“Hello?  What are you two up to?”
“Sam’s just admiring Bobbi’s dress.”
Wendy burst out laughing.  “Admiring what?  And are you impressed, Sam?”
Sam looked up and smiled.  “Very impressed.  Nicest one I’ve seen for a long time.  Wouldn’t mind getting my hands on one like that!”
“Looks like you already have!”
To Bobby’s chagrin, they all fell about laughing.  His recent fleeting fantasy of actually becoming a professional housemaid, earning respect and admiration, evaporated under such coarse humour.  Instead he was being used as a mere object of amusement and ridicule, even having his most private parts exposed, casually handled and made fun of!  He couldn’t bear it.  He stamped his foot, dropped his skirt, and clumped off into the kitchen.  The ladies exchanged glances.  Clare rose and went after him.  She found him standing facing the wall.
“Bobbi.  Bobbi!  Turn around.  At once, or I’ll get the cane to you!”
He complied, reluctantly.  He was frowning and his eyes glistened.
“Now listen to me, young lady.  You can’t behave like that.  You’re a servant and you do what you’re told and you do it cheerfully.  Now you need to go and apologise to Sam at once, or I’ll get the cane and I’ll put you across a chair and cane you on your bottom right in front of her.  Choose now.  You have five seconds.  One, two, three…”
“I’m sorry, miss…!”  Tears welled up and trickled down his cheeks.  “I’ll apologise…”
“Right.  Now listen to me.  If you think that’s the greatest indignity you’ll have to suffer, think again.  That was nothing.  If you want to be in service, it goes with the job.  Understand?”
“Yes, miss…”
“Now come here…”
She wrapped her arms round him, patted his back, and gave him a soft kiss on the neck.  He didn’t see it, but her face was contorted with suppressed amusement.  With an effort she recovered her seriousness.
“Now go and make your apology.”
She listened from the kitchen as he abased himself before Sam.
“I’m r-really s-sorry, madam.  I-it’s my first day, and…(sob) I don’t know all the rules yet…”
“There, there, Bobbi.  No offence taken.  Pay attention to your mistress and you’ll soon learn the ropes.  You’re a smart b… I mean, girl.

[Simonssister]

Chapter 42.

Steph and Lydia arrived together.  The animated conversation they were having outside the front door ceased abruptly when they clapped eyes on Bobby.  He had recovered from his strop, and  taken Clare’s advice to heart.  Being a real maid wasn’t the easiest job.
“Please come in, ladies…  Welcome.  May I take your coats?”
“Oh, thank you, miss!” responded Lydia with exaggerated politeness.  “What a charming maid you have, Wendy…”
“How are you, girls?”
As Bobby headed off to the spare room with the coats, Lydia took Wendy’s arm.
“Who’s that cutie, darling?”
Lydia had brown eyes and studiedly tousled black hair.  She wore a loose orange jumper, short black pleated skirt and calf-length boots.
“She’s not really your maid, is she?” added Steph, the taller of the two.  She had auburn hair, piercing blue eyes, and a slightly Roman nose, and wore a long blue dress, boots and a lot of jewellery.  “It’s one of your friends, Clare, dressed up.  Right?”
“Not quite, Steph.  No, it’s really our maid.  Well, to be precise, my maid.  Here, I’ll even show you the contract.”
The processed into the lounge.  Sam was still sitting sipping her drink.
“Hi girls!”
“Hi Sam.”
“Hi Sam.  You’ve met the maid, then…”
“Yes, we’re already good friends, in fact,” laughed Sam.
Wendy retrieved the contract and passed it to Clare, who handed it to Steph.  Steph ran her eyes over it.  “Bobby?  She’s a boy?”
“I thought it was!” cried Lydia.  “But I didn’t want to say in case I was wrong.”
“How…  I mean, how come you have a boy, dressed as a maid, and he really is your maid….?
“It’s a long story.”
“I mean, does he want to be?”
“Shh.”
Bobby returned, head down, and went and stood quietly by the door, awaiting instructions.
“Bobbi,” said Clare, “ask the ladies if they’d like a drink and attend to them, please.”
“Yes, miss.  Er, ladies, can I get you drinks?”
“Oh, thank you Bobbi,” smiled Lydia.  “A glass of white wine, please, and here – put this bottle in the fridge while you’re there.”
“I’ll have a gin and lime,” added Steph.
“Yes, madam.  I’ll bring some snacks too.  Excuse me.” 
He took the bottle and disappeared into the kitchen.  The ladies sat down.
“He’s so sweet!” whispered Steph.  “Clare, you’re so lucky!  Is he going to live in, or what?”
“Maybe eventually.  I’m going to train him up whenever I have him.”
“He has other talents, too,” added Wendy.
“Such as?”
“He’s learning to be a boot boy.  You know, cleaning and polishing ladies boots.”
“He can do mine anytime,” cried Lydia.
“I’m sure he love to…”
“I love his outfit,” said Steph, in a low voice.  “All that rubber…  I mean, the gloves alone are so sexy…”
“Wait till you see his panties, darling,” smiled Wendy.
“Yeah,” grinned Sam.  “I’ve had a sneak preview and I can tell you, there’s quite a lot to see!”
“Meaning…?”
“Later, Steph…”
“And the collar,” said Lydia.  “Like a pet…  I mean, you could put him on a leash and take him for a walk…”
“Clare’s already had him on a leash, haven’t you dear?” said Wendy, with a laugh.
“Yup.  But I haven’t taken him for a walk, yet.  I shall, though…”
“Shh..  I think he’s coming back,” whispered Wendy.  “Treat him as if he’s a girl, though, please…”

Bobby came in with the drinks and three bowls of snacks on a tray.  As he bent forward to hand Lydia her wine, Steph got a brief glimpse of his latex panties.  Her face lit up, and she gave Wendy a thumbs-up.  He turned, and she quickly became serious again.
“Thank you, Bobbi,” she said, as she took her gin.
He put the bowls down on the coffee table, and turned.
“Can I get anyone else something?”
“Yes, Bobbi,” said Clare, curtly.  “Sam, another?  Yes, and mum and I will have wine.”
“Yes, miss Clare.”

Clare had had an idea.  Bobby was being annoyingly perfect, and what she wanted was an opportunity to assert her authority in front of her mother’s friends.  She fingered the remote which he had tucked in the top of her boot.  She waited till he was handing Sam her drink, then gave it a touch.  Bobby jumped.  Though Sam managed to take her drink before it got spilled, both glasses of wine toppled over on the tray, which overflowed, spilling cold wine straight onto Sam’s lap!  She screamed and jumped up, as Bobby staggered back, trying to keep the tray level.
“Bobbi!” cried Clare, feigning surprise.  “What the hell…?”
“I’m sorry, I’m sorry…” he whimpered.  “I’ll get a cloth.”
He dumped the tray on the floor and ran to the kitchen, returning instantly with a cloth.  He fell to his knees and started mopping at Sam’s leggings.  She had put her drink down on the side table, and was dabbing her jumper with a tissue.  She was angry and didn’t mince her words.
“You careless little bitch!  Look what you’ve done!  These leggings are brand new!  Why did you do that?”
He could hardly explain…  “I’m sorry, madam…”
“Get your hands off me!  Are you trying to grope me or something?”
Wendy and the others were trying to keep straight faces.  Lydia had grabbed a box of tissues from the dining table, and was helping her friend get dried off.  For Clare things had worked out even better than she had hoped.  Now she was fully justified in disciplining her maid in front of everyone.  She rose, fetched her cane from the dresser, and placed her hands on her hips.  Bobby was still on his knees.  She adopted the tone injured patience, like a teacher with a habitually misbehaving child.
“Right, young lady.  Get up – quickly – and go and stand in the corner till I’m ready for you.  Go on.  Really, you have a long way to go, Bobbi, you really do.  And I can see you’re going to need constant reminders.”
“Training a maid from scratch isn’t an easy task, is it dear?” suggested Wendy.
“Indeed not, mother.  I doubt this one little cane will be enough.  Perhaps I should ask Lavinia for a good stout riding crop…”

She waited patiently for Sam to restore herself to some sort of order, and for everyone to be supplied with fresh drinks.  She wanted to keep Bobby on tenterhooks as long as she could.  Then she had everyone seat themselves in a row, on the sofa and in the armchairs, so they could witness the maid’s chastisement in comfort.  She was looking forward to it – not just to demonstrating her authority, but to the process itself.  She had experienced a thrill of pleasure the last time she had given him a stroke of the cane, and the thought of making him squirm with pain had already got her mildly aroused.  At the last minute she decided that, if she was going to cane him, she should make it into a proper demonstration.  So she fetched his accessories from the drawer.
The audience watched with interest as she buckled on his wrist cuffs, with his arms in front of him, then his ankle cuffs.
“M-miss Clare…please…You know I couldn’t help it…”
“Quiet!  Not another word.  I can see I’m going to have to teach you a proper lesson…”
She picked up the gag.  “Open your mouth.  Do it!”  She thrust in the ball, threaded the strap through the back loop, and buckled it up tight.  “There…that’s better…”
His shiny peach lips had been forced into a nice round “O” around the blue rubber ball, and his eyes had become round and scared in sympathy.  Clare pushed another armchair into the middle of the room, and made him bend over the back.  She padlocked one end a length of fine chain to the link on his wrist cuffs, and skated the rest under the chair.  Then she went round behind, pulled it taut, and padlocked it to the link on his ankle cuffs.  She stood up and regarded him with satisfaction.  He was bent right over, unable to move or to speak.  His skirt was sticking up revealing his tight little rubber panties.  Lydia was the first to notice the faint ring in the rubber on the seat of his panties, where the stalk of the plug was attached.  She turned her head and whispered “butt plug” to Steph, who peered and nodded back.  Clare smiled.  She tucked Bobby’s skirt under the apron ties to keep it out of the way.  Her audience looked on expectantly.
“You look like a real dominatrix, Clare,” observed Steph.  “What with those boots and tights and everything.”
“You look hot,” added Lydia.
“Darling,” said Wendy, “where are your leather riding gloves?”
“Good idea, mum.  I’ll get them. They’re in the hall.”
She slipped out, and came back pulling on a pair of short, fine, black leather gloves. 
“That’s better.  Would you like a drink before you start?”
“Oh, thanks, mum.”
“Peach vodka?”
“Great.”
“How many strokes do you think he deserves?” asked Lydia.
“Good question.”  She bent over and patted his cheek.  “How many do you deserve, Bobbi?  Six?  Twelve?  More?”
Bobby made protesting noises and shook his head as well as he could.
“Sam, you’re the injured party.  How many?”
Sam eyed the cane with anticipation.  “Can I help?”
“Of course!  Let’s see how it goes, shall we.  “Oh, thanks, mum…”
Wendy had brought her drink.  Clare sipped it and smiled.  “Mmm…  So refreshing…”
Bobby fidgeted.  Clare put down the drink and swished the cane.  He tensed.  Sam giggled.
“Ready, everyone?” asked Clare, looking at the ladies.
“Can we film it?”
“Please do,” said Wendy.  “Our maid’s first proper punishment.  The first of many, I think…”
Clare compressed her lips.  She stood opposite the onlookers.  She raised her arm, tested the trajectory a couple of time, then brought it down as hard as she could on his bottom!
Bobby emitted an audible squeak and jerked violently.  But the armchair was an old, solidly-constructed one, and it didn’t move an inch.  As Bobby subsided into muffled whimpers, Clare put down the cane, pulled on the chain to test its tightness, then knelt down behind Bobby’s trembling legs, undid the padlock, shortened it by a few links, and resecured it.  Then she resumed her position, and laid the second stroke as close as she could to the first.  His whole body shuddered, and a strange sound, a desperate, high-pitched, series of drawn-out sobs, came from somewhere at the back off his throat.  Sam was nodding with grim satisfaction, Wendy looked on with an expression of approval, even pride in her daughter’s strictness, while Steph and Lydia continued to film with fascinated attention.  Clare herself was savouring every second.  It her mind she was repaying all the rejections and insults she had received from boys in recent years.  She was relishing the feeling of absolute power, physical now as well as psychological.  Her cheeks were flushed, she was breathing hard, and the whole situation – the helplessness of her victim, the ladies’ rapt attention, her outfit, and the feeling of her new high boots gripping her thighs – were contriving to heighten her sexual arousal: she could feel her nipples stiff against the lining of her dress – she wore no bra – and her panties were moist with excitement.  At the same time, however, she was feeling frustrated; if it hadn’t been for her audience she would have interpolated the strokes of the cane with strokes of her pussy!  She prepared to deliver another, running the end of the cane slowly up Bobby’s bare legs, making him shiver with fear. 
The third stroke brought forth a chorus of even louder sobs, and violent squirming of the posterior.  Clare thought she should check the status of his erection, and casually slipped her hand between the back of the chair and the front of Bobby’s panties.  The loops were still holding it firmly in place, but it was soft and squishy now, and squelched faintly as she fondled it.  She played with it until she felt it beginning to swell again, then removed her hand and caressed his burning bottom, making him wince.  She laughed.  No pleasure for him today.  Why should he enjoy himself when she was forced to be chaste?  Then she had an idea.
“I’m just going to get a drink of water.  Sam?  Want to have a go?”
“Yes please!”  She jumped up, and Clare handed her the cane.
“Wait a second – I’ll be right back.”
She went into the kitchen.  Her mother was preparing some sort of dish for dinner, and she had remembered there was bag of baby courgettes on the counter.  Quickly she selected a nicely-shaped one, washed and dried it, and with a “Won’t be a sec!” to Sam, pulled down the front of her tights and panties, and pushed it, blunt end first, into her pussy!
It slipped in so easily, and felt so good!  She pulled up her panties and tights, too a deep breath, and returned to the lounge.  It moved inside her as he walked, disseminating such pleasant sensations that she couldn’t suppress a gasp of delight.
“Are you all right, darling?  You look flushed.”
“Fine, mum.  Hot work, caning naughty maids!”
“Yes, your ears are bright red…”
“Oh, really…?”  She touched one ear awkwardly, but couldn’t think of anything to say.
“So…Clare…  Do you mind if I….?”
“Oh, Sam…  No, of course not…  Just a second….”
Clare noticed his saliva was dripping from the ball gag, so she mopped it up with a tissue and put a cloth under it.  The she sat down in Sam’s chair to watch her efforts.
Sam’s first stroke missed Bobby’s bottom, and landed across his thighs, making him moan with pain, and raising a read weal on his flesh.
“Ooops…”  Sam looked up guiltily.
“Don’t worry,”  Clare reassured her.  Legs are legitimate targets, anyway.  Try again.”
The next stroke landed fair and square across his buttocks.  Bobby quivered and sobbed.
“Bullseye!  Well done!”
Clare was enjoying watching.  She pressed her behind into the cushion, forcing the courgette in as far as it would go, and discovered that by rocking gently back and forth she could make it feel as if it were gently fuc-king her.  By the time she had watched Sam deliver, albeit rather hesitantly, another three strokes, her panties were wet and she was on the verge of orgasm.  She rose.
“Let me continue, Sam.  How many’s that?  My three, your five…eight.  Another four would be fair.”
She took the cane, strode forward, and delivered a stinging blow, making Bobby do an odd little static dance, accompanied by a series of little pleading whinnies.  She bit her lip and, squeezing her buttocks together as hard as she could  to drive the courgette deep inside, thrashed him again and again until a wave of indescribable ecstasy exploded inside her.  With a cry, she dropped the cane and sank gasping to the floor, and sat there shuddering with pleasure until her climax was spent.

[Simonssister]

Chapter 43

When her mind finally cleared, she could hear Bobby still snivelling.  She looked at the ladies.  They were staring at her in astonishment.  There was no way she could have concealed or excused the fact she had just c-um, and c-um hard.  She smiled sheepishly, and pulled herself to her feet.  She needed to change.
“Excuse me.  I’ll be back.  The padlock key’s on the table.  You should let him up now.  I think he’s got the message.”
No-one replied.  Steph and Lydia exchanged surprised looks.  Sam looked in a state of shock.  Wendy simply said, “Goodness,” picked up the key, and began to free Bobby.  Her friends conducted a whispered conversation.
“She had an orgasm – right?”
“Definitely!”
“That’s so…sexy!”
“Seriously kinky.  Just from caning the maid…”
“You were right, Steph…  You know, about her being like a dominatrix.  Imagine getting so aroused just through thrashing someone…”
“She should do it professionally if she enjoys it that much…”
“She should…”
“Poor Bobbi…  How many strokes was that?”
“She must have hit him seven or eight times at the end…”
“Wow.  Is he all right, Wendy?”
Bobby had been released and was standing there rubbing his bottom.  “Oww…  That hurts…” he said, slowly.
They burst out laughing, partly from relief.  He obviously wasn’t seriously hurt.
“I think the rubber panties helped,” remarked Lydia.
“I’ll get you some cold cream, darling,” said Wendy, hurrying off upstairs.  She returned with a large white pot, a towel, a packet of baby wipes, and a box of surgical gloves.  Lydia took charge.  She made him kneel, and despite his protests eased down his panties until his coc-k slipped out of its upper retaining loop, after which she gave him a good wipe over, coc-k and all, just as if he were a baby, and made him lie face down on the towel.  His bottom was criss-crossed with red stripes.  She took a scoop of cold cream and massaged it gently into his skin, making him squirm, not with pain now, but with relief.  Soon they were all helping, taking it in turns.  Steph noticed the marks of the cane extended to the sides of his buttocks, and despite spirited resistance the ladies turned him over and extended their attention to his flanks, and then his tummy.  The inevitable result was that his erection began to grow until it was standing there, proud and straight, before their eyes.  A moment’s discussion resulted in the unanimous opinion that it too would benefit from a gentle application of cold cream, with the result that when Clare returned to the lounge she found her maid surrounded by a circle of women attending to its welfare, with minimal resistance from its owner.
“Excuse me!  What do you think you’re doing?”
“Oh, er…Clare!  There you are,” began Lydia.  “We were…er…yes, we were just trying to cool him off…”
A large bead of pre-c-um oozed from the tip and trickled down the shaft.
“That’s enough.  He c-ums when I say so, and only when I say so.”
The ladies looked disappointed.
Clare knelt, wiped it clean with a baby wipe, produced a condom, and rolled it on.  It was long, with a narrow reinforced lip, which she snapped into place behind his balls.
“That’ll keep his juices under control.  Now…”
She slid his panties up, feeding his stiff coc-k through its shaft loop, and adjusted the waistband.  She unpinned the back of his skirt.
“Now get up, Bobbi, and stand in your place.  It’s time for you to serve us lunch.  I hope you’ve learned your lesson, and you’ll be a little more careful from now on.”  She unbuckled his ball gag and popped it out of his mouth.  “There.  Now be polite, and careful, is that clear?”  He nodded, unhappily.  “Good.  I don’t think a second caning so soon after the first would be as easy to bear.  Ladies, let us be seated.”

[Simonssister]

 Chapter 44

They ate a cold lunch, and drank freely, and soon any lingering reticence had been washed away.  Wendy sat at the head of the table.  On her right were Steph and Sam, in that order, and on her left, Lydia and Clare.  The conversation flowed as easily as the wine, and the ladies began to take liberties with the maid.  Bobby was pouring Sam a glass of Chablis when he felt her hand on the back of his thigh.  She stroked it softly.
“How’s your bottom, now, Bobbi?  Is it still sore?” she enquired in an undertone.
“Only a little, madam.”
“Ooh, good.  Nothing like cold cream, is there?”  She lowered her voice further.  “Pity your mistress came back when she did.  We were going to give you…” – here he hand travelled up his leg, and her fingers pushed between his upper thighs – “…a little treat!”   She kept Clare in view out of the corner of her eye in case she noticed, but she was chatting to Lydia and showed no apparent interest. So Sam turned her hand upwards and gentle cupped his balls.  Bobby flinched, but obeyed Clare’s instructions not to react.  He was a maid, and a maid must be ready for anything. 
Clare of course was fully aware of what was going on right opposite her, but this was much more what she had had in mind.  She knew that once her mum’s friends had had a few drinks they’d be tempted to tease the maid, and she wanted to see how far they’d be prepared to go and how far Bobby’s enforced self-discipline would stretch.  It would be great training for him, and great fun for her.
Sam’s wandering hand was also visible to Steph.  She was getting jealous, so she said loudly,
“Bobbi?  Bring me a clean glass and some red, please.”
Bobby was relieved to have another order which allowed him to tear himself away from Sam.  But it was out of the frying pan into the fire, because when he returned and stood by Steph, preparing to pour her wine, she “accidentally” dropped a fork, and in bending over to pick it up contrived to slide her hand up the front of his skirt and fondle his coc-k, which, to her great satisfaction, (and probably largely thanks to Sam’s fingerings), turned out to be satisfyingly firm and plump.  She had time to give it an affectionate squeeze before she resumed her seat.
“Drop something, Steph?” said Clare, breaking off in the middle of her conversation with Lydia.
“Oh, er…yes…just my fork…” she replied, colouring slightly.
“In future let the maid get it.  It’s her job, not the guest’s.  Bobbi – get Steph a clean fork at once.”
“Yes, miss.”
“And would you bring me some more olives, Bobbi?” put in Lydia, who wanted her turn at groping the maid.  When he returned, she deliberately leaned towards Clare, so Bobby would have to go to the other side, where she could fleetingly slip her hand us his skirt.  Without making it obvious what she was doing she was only able to touch his rear; but that was fine, because what interested her was the little circular area in the seat of his panties.  She located it, and gave it a press.
Bobby squeaked and jerked upright, nearly dropping the little dish of olives.  Fortunately for him he managed to recover himself, and placed it on the table.  Everyone had stopped talking and stared at him.
“Bobbi!” snapped Clare, “what’s that for?  One more strange noise out of you and you’ll be straight over the back of that chair again!”
“Ooh, yes please…” remarked Steph quietly, with a naughty grin.
Clare was secretly happy.  She fingered the remote.  One touch on that and he would squeak like a trapped rat, and then she could do, well, pretty much anything she liked to him…  She took another gulp of wine.  She was beginning to feel a little tipsy.  “You’d better look out, Bobby,” she said to herself.  And then to Bobby, “Go on – back to your place.  We’ll call you when we need you.”

Sam had opened up a new topic of conversation.
“A friend of mine just told me something incredible.  No, but it’s true.  She doesn’t tell lies.  She found out by pure accident her bloke was hitting on some young girl from his work.  So she started checking his phone.  He was going to some conference, and he saw she was going to, and they planned to do it while they were there.  Her first instinct was to wreck his place and dump him, but then she saw something online…  And it gave her a much better idea…”
“Which was?”
“She got one of those chastity devices?  Know what I mean?  Like a little cage you put on a guy’s coc-k?”
“Yes, Steph, we know what a chastity device is…”
“Oh, shut up, Sam…  Anyway, the night before he was due to leave, she goes down in the bed – he was used to her going down on him in the middle of the night – she goes down, and manages to get this thing on him, and locks it, and then she gets up and fuc-ks off home!”
“And what happened?”
“He rang her at six the next morning going berserk!  He threatened, then begged and pleaded.  She had some fun with him, then finally agreed to bring the key to him at lunchtime – they were due to leave at two – if he would confess and promise in writing never to contact her again.  Of course he was so relieved.  But she went in the middle of the morning, walked into his open plan office, and, holding up the key on a big red ribbon, called out to the girl, “Here’s the key to David’s chastity device.  Enjoy.  But keep him locked up when you’re not with him – he absolutely can’t be trusted, you know.”  She tossed it over and walked out.”
“And did she unlock him?”
“Apparently she took the key, went to the loo, and flushed it away.  It would have been too humiliating to go with him after that!  What happened to him, I don’t know…”
“Brilliant!”
Clare smiled mischievously.  “That’s interesting.  Don’t you think…  Maybe it would be the perfect solution.”
“For what?” asked Wendy.
“As a training tool…for a boy maid who needs keeping in check.”  She looked slyly at Bobby, whose eyes had widened with alarm.  “Think about it.  One, he wouldn’t get distracted if he were amongst girls or ladies.  Two, they wouldn’t be so inclined to interfere with him – he’d just be a maid to serve them, a sexless being in a dress.  Three, it would be the ultimate control aid.  If he did his job well, it could be removed occasionally to allow him…some relief.  If he screwed up, it also would remain…(she laughed)… screwed up!”
All eyes turned towards Bobby.  He looked most uncomfortable.  He didn't say anything, but thanks to Nicole he had already experienced that particular form of pleasure deprivation.
“If you’re thinking about Bobbi, I think it would be a shame,” said Lydia.  She’s so nice just as she is…”
“Maybe Lydia…if you want a quick grope…  But in certain situations…  For instance, I haven’t told you this, but my so-called boyfriend – he isn’t really, by the way – he called here and started hitting on Bobby.”
“What?  You’re joking…”
“No.  With him it’s literally “anything in a skirt”.  He wants his family to “employ” her – code for him having sex with her basically, or at least abusing her somehow.”
“He thinks he’s a girl?” gasped Sam
“Yup.  Fooled him easy.”
“So…what are you going to do?” said Lydia, excited.
“He wants her to ring him this week.  So she will…  And I’m thinking we’ll pretend she’s alone in the house, and see what transpires…”
“No, miss…please…”
“Shush, Bobbi!  What have I told you about not speaking until you’re spoken to?”
“But…”
“Where’s that cane…?”
Bobby shut his mouth tight.
Lydia looked thoughtful.  A smile spread slowly over her face.  “Suppose…he tries something…?”
“Well, he’ll be disappointed, won’t he?”
“And extremely embarrassed!”
“Quite.  I’d be so happy to see that, after the way he’s treated me.  Such a condescending bastard.  I just have to work out the details…”

[Simonssister]

Chapter 45

Bobby was in great demand, mainly as a wine waiter.  He held the chilled bottles in a napkin, and kept the opened ones in ice buckets to keep them cold.  The covert fondling was becoming unashamed groping, and when Sam shouted  “Bobbi!  Show us your panties!” there was a chorus of approval.  Bobby, flustered, headed back into the kitchen on the pretence of putting wine into the fridge.
“Clare… sweetie…  Make him show us his little panties, won’t you?  I wanna see how that nice little coc-k of his is getting along…  Maybe it’s lonely…” slurred Steph.
“Yeah, come on, Clare…  where’s the floor show…?”
Clare herself didn’t usually drink so much wine, and she was feeling receptive to the girls’ requests, especially as she wanted to try out the anal vibrator.
“Okay, girls…  Tell you what…  I agree, but….”  (Shouts of “hooray!”)  “But…  No touching.  No touchy.  Geddit?”  (“Nooo…!”)  “Yes!  But I’m gonna show you…our special…er, housemaid dock…yeah, that’s it….  Wait…  Bobby?   Come here…  Now! “
Bobby appeared in the doorway, frowning.
“What, miss?”
“What?  How dare you!”
“But, miss…”
“Silence!”
“Miss.  I haven’t had anything to eat or drink apart from a couple of snacks.  Even a maid has to be fed…”
Everyone fell silent.
“You haven’t…”  Clare realised it was true.  In her normal state she would have sent him back into the kitchen to make himself a plate of food.  But she was drunk, give or take a glass, and she suddenly became so emotional Bobby at first thought she was being sarcastic.
“Oh my god, I didn’t realise…  I’m so sorry.  Mum…”
“I’ll make him some food.  You stay there…”
“You poor thing…”  Clare had her arm round him now.  Mum will be back in a moment.  Come here, sweetie.”
She sat back down and actually pulled him onto her lap, and started feeding him from her own plate as if he were a child!  Then Wendy came back with more food, and Lydia poured him a glass of wine, and…  Well, for the next ten minutes everyone just sat around watching him stuff his face.  It was during that ten minutes that Clare recollected what she was about to do.  So as soon as he was finished, she got him to his feet and set about cuffing his hands behind his back. That done, she and Wendy half led, half dragged him to the wall behind Sam and Steph, and with Wendy’s help attached his wrist cuffs and his collar to the staples.  The ladies looked on with approval.  His mistress had treated him nicely, and now he would repay her by being the butt of their jokes!  With a satisfied smile she wiped his face with a baby wipe, then picked up the big safety pin she had used for his spanking, and pinned the front of his skirt to the middle of his chest.
“There, ladies.  Bobbi’s panties, ready for inspection.”  She stood back.  “Ooh, what were you doing in the kitchen, you naughty boy…?”
His engorged member was straining against the latex, bulging either side of the shaft loop.  The glans was swollen and nudging at the waistband.  In his embarrassment he shifted from one foot to the other, and if he was doing a little walk that took him nowhere, and as he did so the head twitched and slid a little from side to side.  The ladies just stood and started.
“C-can I have a quick feel, Clare,” asked Lydia.
“You know what I said…” she murmured, distractedly.  Then, “oh go on, then…but be very gentle…”
Lydia approached and, with her eyes on Bobby’s face, took the head between finger and thumb.  He squirmed.
“No!  Don’t do that!” he cried.
“Clare, darling,” said Wendy, “I think you should…you know…”  She made a gesture towards her mouth.
“Oh, his gag.  Of course…”
“Oh my god, Clare, it’s so hard…and so hot.”
“Let me get this on him…”
“No!  Mmmff….”
“That’s better.  Now…  Lydia, darling, I think you’d better let go, now…thank you.”
They pulled out their chairs and arranged them in a curved row to get a good view, and sat there in relative silence for a while, sipping their drinks.
“It’s certainly impressive,” said Steph.  “And I’ve seen a few…”
“I bet you have,” laughed Sam.
Lydia licked her lips.  “Can you imagine…what it would feel like…”
“That's enough, Lydia…” said Wendy.

Clare was smiling excitedly now.  She positioned herself by Bobby’s side and turned to face the ladies.  In her thigh boots and fishnets she looked like a ring-mistress introducing the next act.  She had picked up her cane and used it as a pointer.
“Ladies.  Allow me to introduce once again our new maid, Bobbi.  But as you now know, Bobbi has a secret identity as a boy, Bobby Tucker.  Bobby the boy now stands before you.  As you can see, his boyhood stands before you as well.”
As she said this, she prodded it carefully with the end of her cane.
“Now, you can see pretty much all there is to see, right?  Here are those pretty pastel blue panties you’ve all been demanding to see.  The latex is so fine it’s almost see-through – you can even see the pink tinge of the condom I put on him earlier.  However, there’s one thing you can’t see.  These are no ordinary maid’s panties.  Bobby’s outfits are supplied by his aunt Nicole, and manufactured by Fantastex.  These panties have a special built-in accessory…”
Bobby was frowning shaking his head vigorously.
“As I was saying, a built-in accessory – an anal vibrator, a little vibrating egg on a stalk, which can be activated by this simple remote control.”
She slipped it out of the top of her boot and held it up for them to see.
The ladies goggled, delighted.
“It’s actually…inside him?” gasped Lydia, her face breaking into a huge grin.
“Yes.  Right inside.”
“Are you going to demonstrate it, Clare?” piped up Sam, eagerly.
“Shortly, yes.  Bobbi, please stop fidgeting like that.  It won’t do you any good.”
“What’ll happen when you turn it on?” asked Steph.
“I have no idea.  I’m as fascinated as you to see the effect.  There are ten levels of vibration.  Shall we try it on one and see if anything happens?”
“Do it!” they cried in chorus.
Clare clicked the dial round to one and pressed start.  Bobby had been squirming against his bonds, but immediately he froze and stiffened.
“He can feel it, see?” said Steph.  “Try the next one.”
Clare clicked the dial onto two.  At once Bobby began to tug at his tethers.  He made a weird protesting noise, and glared at them impotently.
“I don’t think he likes it much,” suggested Sam.  “Stick it up to five and see what happens.”
Clare took another gulp of wine.  “Yeah.  If he doesn’t like it, too bad.  He’s just the fuc-king maid, after all.  Here we go…three, four, five…”
Bobby started squeaking frantically, and pressing his thighs together, first one way, then the other, until he actually managed to cross his legs completely.  They all laughed at his discomfiture – and then Lydia cried, “Look!  I can see it vibrating!  His coc-k!  See?”
They left their chairs and surged forward, squatting or sitting on the floor around their victim.  It was true!  The vibrator was only on five, and that big coc-k was vibrating so fast it was almost a blur!  And Bobby himself?  He was going crazy!  There were tears in his eyes and his legs were no longer crossed, but he was almost dancing!
“Turn it off!  Turn it off!  Just for a moment!” cried Sam.
Clare clicked the off button.   Bobby hung there, eyes half-closed, chest heaving.
“Wow!  What must that feel like…?” said Steph.
“Awesome!” added Lydia.
“Why did you tell me to turn it off, Sam?” asked Clare.  “It was pretty cool, what was happening there…”
“Because…  Don’t you see?  A few seconds more and he would have c-um.  Let’s do it again, but slowly, so we can enjoy it.  Why don’t you let me have a go?”
“Well, okay, if you think you know best.”
“I do.  Wait and see.”
So Sam took over.  She started off slowly.  Even at low vibes they could feel it in Bobby’s coc-k.  They took turns to touch it while Sam turned the power up and down.  After a few minutes she’d worked it up to four, which seemed to be the highest level he could bear without c-umming.  She then turned it down to three to lull him into a sense of security.
“Right.  How’s about we make it pop, girls?” she whispered.  “You ready?”
They all nodded excitedly.
“Okay…  Here we go!”
She switched it suddenly to eight.  Bobby started struggling frantically.  He lasted about ten seconds, and then…
It was some orgasm - a jerking, choking, straining, whimpering, shuddering explosion which lasted for the best part of a minute.  They watched fascinated as wad after wad of sperm erupted from the tip of his spasming pen-is and filled the condom, making a plump little bubble under the latex.  As it subsided, he head fell forward and he sighed deeply through his nose.
They had all been either kneeling or on all fours, getting as close to the action as they could.  Now they settled back and sat on the floor, looking at each other.
“That was amazing…!” cried Steph.
“Awesome!” said Lydia, again.
“Cool” remarked Clare.
“Let’s check it out,” said Sam, getting to her feet.  “Steph?  Hold this.”
She had pulled out the waistband of Bobby’s panties.  Steph got up and held it open, while Sam reached inside.  She stretched the end of the condom and pinched it to make sure none of the precious sperm escaped, then drew it slowly off the shaft, after which Steph allow the waistband to snap back into place.  Sam held it up.
“That’s a pretty good yield, don’t you think?  That’s the key.  Keep him aroused for as long as possible, then a really thorough milking and a good long climax.” 
Lydia closed her fingers around the filled condom and palpated it, making the fluid squelch and bubble inside.  “It’s still warm.  And so creamy,” she mused.
“Let’s make a sauce!” cried Steph.  For our pudding!  For our sticky choccy pots!”
“Let’s!”
They went into the kitchen, found a tumbler, and, lowering the filled end of the condom inside, rolled the mouth over the lip.  After some discussion they added a white of egg, a spoonful of double cream, and a little blob of condensed milk for sweetness.  They tied it off and took turns to squidge it in their hands till the contents were thick and white and creamy.  Then they took their choccy pots and headed back to the lounge.  They showed their new sauce to Bobby, then Clare used a pin to pierce the teat, and they took it in turns to squirt the sauce onto their desserts.  It was delicious!
“It’s so useful to have your own milk cow,” remarked Steph, licking sticky sauce mixed with chocolate off her lips.
“This is better than cream,” said Wendy, stirring it into the chocolate and making white swirls.  “I wish we had more.”
“Oh, I’m sure there’s lots more in there,” grinned Sam, giving Bobby’s balls a prod.  Let’s give him half an hour and try again.”
“Yes.  And don’t worry, Bobby.  There’ll be plenty for you, too!”

[Simonssister]

Chapter 46

As indeed there was!  Bobby spent the afternoon tethered to the wall, providing hours of harmless fun – not to mention exotic coc-ktails - for his mistresses, until it was time for him to serve dinner.  After he had attended to them, cleared away and washed up, he took his in the kitchen, like a real Victorian housemaid, and afterwards, completely drained, fell asleep with his head the kitchen table.  The ladies took pity on him, and left him to slumber, while Clare expatiated of her plans for the week.
“I’ve been thinking, ladies, about Damien.  I want to strike while the iron’s hot.  So this is my plan.  Bobby will ring him as soon as possible – tomorrow, maybe.  He’ll say that Wendy and I will be out one evening this week, if he wants to discuss terms.  We’ll get his room ready – the spare room next to my bedroom.  We’ll clear it out, spruce it up at bit, and put up a few posters.  Bobby will lure him up there.  I’ve already spoken to my friend Frederica – she a techie – and she’s come round and install a couple of concealed videocams we can monitor from my bedroom.  Mum and I will be hidden there.  Then we’ll see what transpires…”
“Ooh, how exciting!” squealed Sam.  “Could we…?”
“Sorry, Sam.  As much as I’d love to have you along, I would be afraid you might accidentally give the game away.  But don’t worry, you’ll definitely get to see the footage if anything funny happens.”
“And…do you think it could…?”
“If Damien doesn’t realise his mistake, I’m sure he’ll make a move of some sort.  Probably he’ll try to steal a kiss at least…”
“But what about Bobby?  I mean, he’ll just run, won’t he?”
“Don’t worry about him.  I’m going to instruct him to go along with whatever happens.  He’s very firmly under my thumb, darling.  He knows anything short of absolute obedience is liable to result in some very painful, not to mention very public, consequences for him.  His aunt Nicole kindly provided me with several of her videos she’s taken of him over the weeks.  The very first one would be enough to keep him in line.”
“Really?”
“Oh yes.  He’s all done up in this cute boot boy outfit, little pink rubber pants, the lot.  Then he stands there all shy and sweet and blushing, and proceeds to play with himself until he explodes in this amazing spectacular climax!  It’s true!  I’ll show it to you in a minute.  He must have been so wound up he couldn’t help himself -  but he must have regretted it the moment he came down to earth again.  He wouldn’t have any of his friends see that for anything in the world.  And there’s others, too….  Rest assured that maid Bobbi will play her part willingly and enthusiastically.”
“Wow…  You really do own him, then, Clare…” remarked Lydia.
“I do…me and his aunts…yes.  You know…what we’re doing is not just a case of us imposing our will on him.  No, we’re also exploiting his deepest feelings, bringing them to the surface.  Why do you think he gets in such an aroused state?  He’s a slave, all right, but not just to me or to Nicole and the others.  He’s also a slave to his fetishes.  He may want to escape them, but in the end they are stronger than his conscious desire to resist.  And the more they surface, the weaker that resistance becomes…”
“Good!” laughed Lydia.  “I love how pretty he looks in his little maid’s outfit.”
“Cute and sexy…” added Steph.
“Oh, I’ve been told he has another one in pink, as well as boot boy outfits.  In fact he’s building up quite a wardrobe.  He’ll need it though.  Lavinia tells me he’s got a couple of engagements coming up in the next week or so.  His aunts and I are planning to keep training him until he’s good enough to go professional.”
“Could he do that?” exclaimed Sam with astonishment.
“Why not?  Think of all the ladies who’d give anything to have a cute little femboy maid waiting on them, even if only for a few days…”
“That’s right!  I’d hire him quick as a flash,” said Lydia.
“I bet you would,” laughed Steph.  “But if he were working for you, you’d need to make sure he had a good kneeling mat or a set of knee pads!”
“I really have no idea what you’re implying, Stephanie…”
“I know what you like…”
“Is he still asleep?” asked Sam.
“Yes.  Lavinia’s happy for him to stay the night.  Would you help me carry him up to bed…?”

Bobby slept like a log, and woke up feeling fresh and rested at six-thirty.  He was surprised to find his school clothes folded neatly on the chair.  He took a shower, dressed, and when he came down he found Nicole and Lavinia sitting at the kitchen table with Wendy and Clare, drinking coffee. 
“Good morning, Bobby.  How are you feeling?”
“Fine, thank you, auntie.”
“I’m going to run you to school.  Have some breakfast.  Wendy’s offered to cook for you, or you can have cereal, or whatever you want.  Take your time.  You have an hour before we need to leave.”
Clare and his aunts repaired to the lounge while Wendy made him sit and started preparing some scrambled eggs and toast.  He could hear the others talking in undertones - about him, no doubt – but he was more interested in eating than paying attention.
“So did your mum’s friends enjoy themselves?” asked Nicole.
“They had a great time.  And to be honest, I think Bobby did too.  Thank you both for letting me take him on.  I’m going to do my best to be a good mistress.”
“I’m sure you will be, Clare,” said Lavinia.  “Make sure you enjoy yourself, too, won’t you?”
“Don’t worry.  I love it.”
“And in due course,” said Nicole cryptically, “I’m going to show you a certain facility I have, which contains lots of useful and interesting equipment.”
“Really…?”
“Yes.  You’ll be able to use it for more intense training sessions.  But it’s a secret place that few know about.  So have patience.”  She smiled.  “Now, this week.  Let us know when that guy…Damien?”
“Damien, yes.”
“Let us know when that’s coming off.  Get some good video.  It make all come to nothing, I realise that…”
“Yes.  Fingers crossed, anyway.”
“Then Saturday it’s Pitt’s Wood…  Are you still okay to take him?”
“Oh, yes.  I must meet those girls.”
“Great.  At some point I’m going to take him to Fleetwood, where I usually ride.  I have a friend there, Fiona, who’s dying to meet him.  Lavinia?”
“Yes, about Saturday.  Jasmine has asked me for some equipment.  Nicole’s going to put that together, and I’ll drop it off to you and explain what’s it’s for.”
“Sounds interesting…”
“Nothing complicated.  Just basic stuff, eh Nicole?”
“Yes, as Lavinia says, nothing special.  Then if you want to keep him Sunday you can – it’s up to you.  The following week there’s a committee meeting at Pitt’s Wood…  What day is that, Lavvy?”
“Friday.  We’re working on a new outfit for that.  Something that should appeal to Miss Poole.  She’s the committee chair, and she was quite taken by Bobby when she met him recently.”
Clare nodded excitedly.  This was fun!
“But Clare…” said Nicole, quietly, “we want him hot and ready for the weekend, so we’re going to fit his, you know, his device, before we leave this morning.”  She took it out of her bag and placed it on the table.
“Ooh!  We were just talking about these yesterday!”  She picked it up and turned it over in her hand.  A little curved tube of pink plastic attached to a ring.  “How clever!  Will he fit inside this, though?  And can he not escape somehow?”
“Oh he’ll go in.  He’ll shrink when he sees it!”  She laughed.  “He’s worn it before.  We measured him for it.  The ring is rubber-covered steel.  The tube is unbreakable.  There’s no escape once we lock it with this little key.”  She held up a tiny right-angled silver key.  “It’s probably for the best with that Damien guy taking an interest.  If he tries to grope him he’ll be very disappointed!”

They chatted away until it was nearly time to leave, then Nicole and Lavinia made Bobby lie on the sofa while they fitted his device, Wendy and Clare looking on with interest.  Bobby was deeply embarrassed, and blushed and shut his eyes tight during the operation.  Once it was over he quickly got dressed.  He sheepishly accepted goodbye kisses from Clare and Wendy.  Clare slipped a phone into his hand.
“This is Bobbi’s phone,” she said.  “She’ll need her own phone to call Damien – you can’t very well use yours!”
“See you in a day or two, Bobby!” she called, as he was led out to the car.

[Simonssister]

Chapter 47

The consciousness of being so neatly and helplessly locked away didn’t help his confidence.  He several times imagined his schoolmates had divined his plight.  And when he was approached at break by Chrissy and Kaitlyn, both of them smiling knowingly, a shudder went through him.  Had Sarah told her daughter?  Why else would she be smirking like that?  He tried vainly to collect himself.
“Hi Bobby?  And how are you?”  (That “and” seemed to bespeak some secret knowledge.)
“M-me?  I-I’m good…   Yeah…great, actually.”
“Oh, we’re so pleased to hear that,” said Kaitlyn, with a note of sarcasm,  “cos we were a bit worried about you…”
“W-worried?  About…m-me?”
“Yeah,” resumed Chrissy.  “Cos when we saw you the other day…”
“You s-saw me?”
“Yes,” said Kaitlyn, “with your aunt…”
“And we could have sworn…”
“You were on a sort of lead…  Or something…”
Bobby turned bright red.  He thought for a moment he was going to faint.
“That was you, wasn’t it?”
“Me?  Oh…”  There was no point denying it.  He must think of an explanation.  He’d bluff it out.  He managed an awkward laugh.  “Oh, yeah…that…  Yeah…  I was practising, like…trying out some stupid outfits for…for Halloween, yeah…”
“That’s a long way off, Bobby?  Why now?”
“Well…”
“And what outfit was that, anyway?  Why those little red pants…?  Were they rubber ones, by the way?”
By now Bobby was hyperventilating, his ears were burning, and a cold sweat had broken out on his forehead.  He started stammering inarticulately.
“I-I…  It’s p-perfectly simple…let me explain…  Er, y-you see…”
At that moment the bell went for the end of break.  Relief.  Not.
“We’ll talk about it after school, Bobby.  Meet us in the park by the cafĂ©.  Straight from school.  Don’t be late.”
“I-I have a…”
“Let’s stop messing around.  We know everything.  Unless you want this all over the school, be there.”  She held up her phone, with one of Sarah’s videos playing, of Bobby in his boot boy outfit.  “Oh, and if you ever let on to my mum I nicked this off her phone, the same will happen.  Okay?”
And with triumphant grins, the girls turned and walked away, leaving Bobby standing there, speechless and devastated.

He stayed in the school buildings for the rest of the day, tormented by the thought his fame seemed to be spreading wider by the day, and terrified what the girls’ next move would be.  But at the end of school he was one of the first out of the gates, and he ran to the park, eager to show his willingness to cooperate with whatever plans they had for him.  He consoled himself somewhat with the knowledge that the real evidence they held had been obtained illicitly, and that Sarah would be furious if she found out.  Maybe there was a ray of hope…

Somehow they were already there.  They must have got out early.  He could see the two uniformed figures sitting on the steps of the cafĂ©, engaged in conversation, Chrissy playing with her long brown hair, Kaitlyn’s pigtails dancing as she was apparently convulsed with laughter.  He approached, trembling, cheeks burning.
“Bobby!  You came!  Oh, and you’re here,” Chrissy added, with a guffaw.  And they both rocked with laughter.  “Go and buy us coffees.  I’ll have a latte, Kaitlyn wants a white Americano, and get one for yourself.  Then we can sit down at a table and talk.”
No money was offered, and Bobby scurried off, keen to propitiate them.  When he returned he found them seated at one of the outside tables.  A lot of the students went to the park after school, and he checked nervously in case someone looked likely to interrupt them, or overhear.
“M-maybe we should go and sit on the grass…?”
“No.  We like it here.  Now…  What shall I call you?  Boot Boy Bobby or Maid Bobbi?  I think I’ll call you Boot Boy – I love those little rubber shorts so much…”
“Yes, Boot Boy,” smiled Kaitlyn.  “They suit you so well…  Those little frills are so cute…and they fit you perfectly – hug every contour…”
She winked meaningfully.  Chrissy had a mouthful of coffee, and she spluttered and nearly choked with mirth.
Bobby looked disconsolately at the ground.  “What do you want?”
“Ah.  That’s a good question, Boot Boy.  Well, first of all, we want to see you in both your outfits.  All your outfits, I should say.  I bet there’s more.”
“That’s impossible.  I don’t have them.  My aunt keeps them somewhere.”
“Where?  Oh, in her dungeon, maybe…”
A chill ran through Bobby.  He raised his head and stared at Chrissy.  He couldn’t conceal his shock.
“What did you say?”
“Oh, nothing…”  Chrissy realised that her over-confidence had led her to make a stupid error. 
“What do you know about my aunt?  Have you been spying on her?  If you tell anyone anything about her, you’ll be in big trouble.  Your mum…”
“I won’t say anything!  Don’t worry!”
“You’d better not!  Tell me how you know that.  Tell me!”
Chrissy was now completely on the back foot.  Kaitlyn stepped in.
“We came to visit you.  We couldn’t get a reply, so we went round the back to see if anyone was there, and on the way back we saw a grill and some light…  So we looked in…  We weren’t spying at all!  It was accidental….”
“Huh!  We’ll see what my aunt thinks, shall we?”  He thought he had the upper hand now, enough to spoil their plans.  But Chrissy was a tough cookie, and she was equal to it.
“Okay let’s do that.  You’re headed back to your aunt’s, right?  We’ll come with you!” 
She wasn’t sure whether Bobby’s was an empty threat, but there was no way she was going to let him tell Nicole some tale.  She reckoned her own powers of persuasion were superior to his.  And if all else failed, there was always tears!
He looked alarmed.  She had called his bluff.  Now what did he do?
“W-well, she probably isn’t in at the moment…”
“We’ll go and see, shall we?”
He demurred.  “Anyway, I have to go to the shops…”
“We’ll come with you,” said Kaitlyn.  “Then we can all go to your aunt’s together.”
“Or we’ll go to your aunt’s and wait for you to return,” added Chrissy.
“No!”
He was stymied.  Reluctantly he allowed himself to be accompanied to the bus.  He was trying desperately to see a way out, but he was too anxious and confused to think clearly.  All he could do was to hope his aunt gave them a good ticking off.  When she discovered Chrissy had hacked her mum’s phone, surely she’d do her nut…  Wouldn’t she?