His Aunt Nicole

[Simonssister]

Chapter 253.

It only remained to ask Phillipa if she was up for the prank.  She didn’t take much persuading.
“What, Candy?  Are you saying we’d get pageboy – I mean pagegirl outfits, just like those two sissies down at the boot parlour?  That’d be great.  I mean, they look stupid, but on a girl…  But what do they cost?”
“Don’t worry.  My aunt’s agreed to pay.  If she didn’t Miss Poole would have picked up the tab.”
“Really?  That’s amazing.  Why…?”
“You’ll find out.  The boys are Miss Poole’s pet project.  And don’t ever tell them how silly they look!  They think they’re so cool.  They’re even doing a wedding next month, and my aunt tells we they’ve been booked for her friend’s party…”
“Yeah?  That’s hilarious!  So what are we going to do to this Tim guy?”
“We’ll find out soon.  Ellie’s going to show us around the boot parlour when the boys aren’t there.  She’s got plans, I gather.  Whatever they are, knowing her, it’s gonna be fun…”

Once she heard the plan Cynthia was only too happy to assist.  She got Ellie to measure up the girls, and send their measurements and shoe sizes, and three days later the first pagegirl uniforms were ready.
“Come round any time, Ellie,” said Cynthia, when Ellie rang her the Tuesday before Tim’s solo session.  “I’ve made Phillipa’s up just like the boys’, in red latex, with red boots – but for the other girl I didn’t have enough red left and I had to use black.  We already had some black thigh boots in her size, anyway.  I hope that’s okay.”
“I’m sure they’ll both be happy, Cynthia.  We’ll pop over lunchtime tomorrow then.”
“Perfect!  See you then dear.”

They arrived just before one.  Ellie opened the door for the girls.  She smiled as she heard their gasps, as they took in the racks of latex, leather and satin outfits which filled the main part of the shop.  She chatted to Cynthia for a while, and eventually had to go and fetch the girls so they could try on their outfits.
“I cut the shorts a centimetre under,” said Cynthia.  “I imagine you’d prefer a tighter rather than a looser fit.  Tricia, could you take the girls to the changing rooms and help them into their costumes?  Thank you.”

Ten minutes later they appeared, Phillipa slightly flushed, Candy’s eyes dancing with evil delight.  Even Ellie was taken aback.
“Wow…  They look so…sexy!  Especially Candy…  Poor Tim…”
“Oh yes…  I’m afraid that was the only top I had left.  It’s a little small on her, but…”
“Don’t apologise, Cynthia!  Candy, really!  You’re such a flirt!”
Cynthia shook her head.  “These outfits on girls work much better than I had imagined…  I’m so pleased.  I didn’t mention it, Ellie, but I’ve already received a few other enquiries from Pitt’s Wood girls.”
“You have?  Who?”
“Oh, there was a Valerie Casement…  Cathy something…  and another…”
“Valerie?  Cheeky bitch.  She never said a word to me.  She must have looked you up.  Well, well.  Seems like the boys may have started a trend.”  She laughed.  “I wonder how it’ll go down with them.”
“Bobby won’t mind.  His dress is almost ready.  It’s going to look great on him.”

[Simonssister]

Chapter 254.

Candy and Phillipa insisted on wearing their new outfits back to the Centre.  It was after two-thirty when they arrived, so Bobby and Tim were working, allowing the girls to show themselves off to their friends – which had Cynthia’s phone ringing off the hook for most of the afternoon!  But everyone was sworn to secrecy – at least for the next few days, until Tim’s special session.

The next day Ellie arranged for the afternoon sessions to be put back half an hour, and told the boys to take a long lunchbreak.  Once they were gone, she showed Candy and Phillipa into the waiting room.
“Wow!  This is cool…” said Phillipa.
“Yeah…  There’s room for a lot of customers here…” added Candy.
“In the winter, when there’s lots of muddy boots, they might be queueing up,” remarked Ellie.  “But follow me.  I need to show you a few things…”
She led the way into the parlour itself.  The girls were amazed at how large and well-equipped it was.  Phillipa began to check the cupboards.
“There’s everything in here they could possibly need.  All these brushes!  And creams and polishes!  I’m going to book a session for myself, especially now I have these gorgeous thigh boots!” 
She tried the tall cupboard at the end.
“Oh!  Is this locked?”
“Yes.  But I have the key.  Perhaps you’d like to open it.”  She handed Philippa the little silver key.
The others looked on as she turned it in the lock, Candy frowning slightly, Ellie looking smug.  Phillipa opened the door, and looked inside with an expression of puzzlement.  Candy gasped.  Her face lit up.
“Wow!  Sex toys!”
“Yes, Candy.  Quite a selection, too.”
“Gosh, Ellie!” exclaimed Phillipa.  “Will we be allowed to…”
“Use them?  Of course.  I’ll give you a quick preview right now.  Then you can explore everything for yourselves.  This may be useful – but only after you’ve thoroughly psychologically subdued him…  Taught him who’s the boss – or bosses.  He’s been getting too big for his boots recently – forgive the pun – so bring him down to earth.  But always remember not to damage his self-esteem too much.”
She pulled out a small St. Andrew’s cross, made of leather-covered steel.
“Do you know what this is?  No?  The big ones fix to the wall, and allow you to spreadeagle the subject and secure him by wrists and ankles.  This fixes to the floor.  I’ll show you.”
She positioned the cross flat on the floor, with the centre over a small steel aperture sunk into the tiles.  Then she bolted it in place using a long threaded steel bolt which she turned with an Allen key.
“See these rings at the ends?  You fit the subject with wrist and thigh cuffs – they’re right here – they just strap on – and use four screw links to attach them to the rings.  Then he’s down on all fours and there’s nothing he can do about it.” 
“Would he actually let us do that, Ellie…?”
“Oh, don’t worry Phillipa.  You will have special guest status, and he wouldn’t dare refuse.  He has to obey, or be punished by Miss Poole.  That’s what scares him most.”
“Really?” gasped Phillipa excitedly.  “So he has to do everything we say?  That so cool…”
“So what happens then?” asked Candy.
“He’s at your mercy, darling.  What happens next is up to you.  You can have a dig through the cupboards and see what you can find.  I’ll make sure he’s totally vulnerable.  I’ll set everything up in advance, including two little self-focussing videocams.  All the usual surveillance cameras will be turned off.  I’ll put one on the shelf behind the chairs, facing him, and the other on the cupboards on the left.  There’ll be a third in the waiting room covering the chairs opposite the door, so sit there initially.  This is the controller.  I’ll leave it in the waiting-room.  Turn it on just before the session.  If at any time he makes a fuss, there’s plenty of gags in there you can use to keep him quiet.  The best ones to subdue him are the suc-kable ones.  You’ll see some have a reservoir.  He’s got a very sweet tooth so you can fill them with condensed milk.  That’ll calm him down.  There’s a bottle with a special nozzle or some syringes for filling them.”
“Wow, you’ve thought of everything…” said Candy, thoughtfully.
“Not me – Miss Poole.  Anyway, that’s about it.  I’ll let you in early so you can go through the cupboard and see what you might want to use.  No restrictions.  Be inventive!  Any questions?”
The girls shook their heads.
“Remember, try to gain his trust first of all.  Talk to him – see if you can get him to open up.  He can’t resist pretty girls, especially when there’s no Bobby around to take the lead.”
“He’ll be like putty in our hands,” laughed Candy.
“Leave it to us, Ellie,” smiled Phillipa.  “
“Take your time – you have the whole afternoon – as long as you like.  But whatever you do, have fun!”

[Simonssister]

Chapter 255.

Half an hour before the session.  Ellie had already set everything up as planned, and smuggled the girls into the waiting-room while Tim was in the shower.  He had emerged wrapped in a towel in a cloud of scent.
“You smell nice!”
“Yeah.  Cool stuff.  It’s Bobby’s.  ‘E won’t mind.”
“I’ve made you a snack.  I’ll get your outfit.”
“Fanks, Ellie.  So… what’s this Phillipa girl like?”
“I told you.  Pretty, and I’ve heard she’s polite and well-mannered as well.  She’s your age.  Your birthday was in September, right?  So she’s only a month younger than you.”
“Right…”
“Pity Bobby’s not here…”
“That’s ‘is loss, ain’t it?  ‘E’s off somewhere doin’ ‘is own fing…”
“Here’s your uniform.  Pop-front today.”  (She hoped he wouldn’t notice the pop-back as well.)  “It’s a long session, so you may need to use the loo…”
He went into his room, and returned five minutes later fully dressed, baseball cap backwards.  “There’s no plug in these…”
“No, Tim.  I didn’t think it would be appropriate, with Phillipa being a newbie and all…”
“Makes a nice change…”
“Why do you wear your cap like that, Tim?” frowned Ellie.  “Do you think it looks cool?”
“Don’t you?”
“I suppose you think she’ll be impressed…”
But Tim was busy admiring himself in the mirror.
“Why is it so long…?
“I imagine her mother paid, and wanted to make sure she got the works.”
“Oh, she’ll get the works, a’ right…”
“Not the famous Timmy chat-up routine, surely…?”
“Why not?  It never fails…”
“If you say so.  But remember you’re here to work, Tim.  With all the time you’ve got, her boots should be gleaming by the time you’re done.”
“No worries, Ellie.  I’m the best at what I does.  She should be ‘ere by now…”
“Oh.  Maybe she sneaked in.  Let’s take a look.”
She crossed the corridor and opened the door.
“Phillipa!  You’re here already.  And you’ve brought a friend.  Hi, Candy.”
Tim’s face fell.
“Candy?”
He knew her only too well – and her connection to Diana Murchison.
“I’m sure you’ll cope, Tim.  You have all afternoon, after all…” said Ellie, slyly.  With which remark she departed.

Candy and Phillipa were sitting apart, with a seat in between them.  They were like two little peas in a pod, Candy in white and black, Phillipa in white and red.  They were both made up, lip gloss, mascara, the lot.  Their shorts and boots were glossy and immaculate, their spandex tops taut over the breasts, Phillipa’s tucked into her shorts, Candy’s cropped, showing her belly button.  For the session both had stitched little red hearts just above the left breast.  They wore matching baseball caps, Candy’s with a letter C on the front, Phillipa’s a letter P.  Candy had a smug expression on her face.  Phillipa was regarding Tim with undisguised delight.
“Come and sit with us, Timmy,” smiled Candy.
“I, er, weren’t expectin’ t-two…” he stammered. 
Candy got up, took him by the wrist, and seated him next to Phillipa.  She resumed her own seat the other side of him.
“Do you like our outfits?”
“We’re pagegirls!” giggled Phillipa.
“B-but I fought we was the only ones…”
“Not any more, Timmy.  You’ve started a fashion.  You’re going to see pagegirls everywhere from now on!”
Tim looked dazed and slightly nervous.
“See we’re wearing our TFC badges?” said Candy.  “We’re the founder members of your fan club, aren’t we Phillipa?”
“Yes.  We think you’re the coolest, Tim.  I sneaked a piccy of your when you were walking up to the offices the other day.  I’ve printed it out and it’s over my bed now.”
Tim began to take interest.  “Really?”
“Yeah.  Listen – could we have a selfie with you right here.  I brought my selfie stick just in case.  Please, Timmy…”
There was no better way of getting in Tim’s good books than by way of his ego.
“Sure.  No probs.”
Phillipa took three snaps with them sitting, another three standing, with the arms around each other.  She was almost bouncing with excitement.
“I’ll get my mum to print these off.  If I did that…would you sign a couple for us, Tim?”
“Course - be a pleasure.”
“Would you mind if we gave some to our friends to put up at home or in the stables?  We wouldn’t if you objected, but…”
“Go ahead,” said Tim, with obvious satisfaction.  “I mean, if they really want ‘em,” he added, with a pretence of modesty.
“Loads of them have asked us,” said Phillipa, putting a hand on his thigh.  “I can’t believe we got a session with you.  There’s a huge waiting-list you know.  But Ellie somehow slipped us in – even ahead of that Serena girl, she said…”
“Serena?  ‘Er?  I fought we’d seen the last of ‘er.  Thank you for savin’ me,” he laughed.  Then he turned to Candy.
“You’re Miss Murchison’s niece, Candy…”  There was a hint of suspicion in his voice.
“I am.  But don’t judge me by that.  We’re not on good terms.  I don’t know what happened at her last session with you – she refuses to tell me.  But if it was anything like I imagine, I apologise on her behalf.”
Tim felt relieved.  “Fanks.  That’s nice of you.  It weren’t anyfing really bad…”
“She can be horrid.  Especially when she’s with that Eleanor.  She should know better at her age than to exploit young men like you.  But she just can’t help herself.”  She sighed.  “But Tim, seriously, you’re so handsome and you have such a great bod.  You have no idea how many girls want a session with you.  Don’t you find it difficult fending them all off?”
“Well, sometimes…  I mean, I ain’t done nuffin’ to earn all this attention, like…”
Tim was feeling better and better every second.

[Simonssister]

Chapter 256.

There was a few moments silence.  Tim was smiling faintly, and looking into the distance, imagining the whole of the female entourage of the stables worshipping at his feet.  Phillipa thought it was time to jerk him back to reality.
“Do you like our outfits?” she blurted, all of a sudden, gripping his thigh harder and looking up into his face with her big blue eyes. 
“What?  Oh, yeah…  You bofe look tote’ly amazin’!” 
“Really?” said Candy, getting to her feet.  “So you approve.  You’re not annoyed we stole your ideas?”
“No, course I ain’t!  You look gorgeous in ‘em…”
Phillipa rose and took her friend’s hand.  The pair of them sashayed in front of him, their boot heels making seductive little clicking sounds on the tiles.  Tim stared.  Their little shorts clung to their hips, and the spandex tops accentuated their breasts.  He could feel definite stirrings in his own shorts. 
“Which do you like best,” asked Phillipa.  “Candy’s outfit or mine?”
Tim gulped. 
“I-I can’t choose…  The red suits you, Philippa, and the black suits Candy.  Your boots…”  He swallowed, and became confessional.  “Your b-boots are so tall…  They fit your legs so perfec’…   You’re bofe so ‘ot, like…  Them little shorts an’ ‘igh boots wiv just a bit of figh in between…”
He took a deep breath.  The girls smiled and took a pace forward, till his nostrils were full of the scents of new leather and warm latex, and their thighs were in front of his face.  Candy playfully swivelled his baseball cap round so the peak was at the front.
“You look best when you wear it like that…”
“I do…?”
“Yes.  Now feel our boots, Tim.  These are the best quality leather Fantastex had in stock.  Go on…”
He reached out and stroked the leather, first Candy’s, then Phillipa’s.  He was hard now; he could see the bulge out of the lower corner of his eye.
“Feel our shorts, Tim,” said Phillipa, seductively.  “That’s right.  Don’t they fit us well?”
“Y-yes…  Like, really smoove…” he said, weakly.  He was totally in thrall.
The girls resumed their seats.  Phillipa’s hand returned to his thigh, inches from his erection.  She turned her head to his.  He felt her warm breath on his right ear.
“But you’re the smartest out of all of us,” she whispered, “and the sexiest…”.
Candy rested her chin on his shoulder.  Her scent enveloped him.
“Do you know how sexy you are, Tim?  It stands out a mile…”
“Well, six inches at least,” added Phillipa.  And they laughed.
“But seriously,” said Candy, “haven’t you noticed how all the girls ogle you when you go out in your uniform?”
Tim blushed.  “Not really…”
“It’s not true, is it?” she added suddenly.
“What?”
“That you and Bobby…  That you’re gay?”
“Course not!”  Tim snorted with indignation.
“No, I don’t think it can be,” said Phillipa, glancing at the taut latex.
“In which case…  Do you find us attractive?”
His heart was pounding away, his coc-k aching with arousal.  He had no difficulty in replying.
“Yeah.  Bofe of you.  Very, very attractive.”
“Or is it just the outfits?” said Candy.  “What happens if this becomes a trend, and a whole bunch of girls start walking about in cute little pagegirl uniforms?  You know there are others, already.”
“There are?”
“Oh, yes.  Let me see…  There’s Justine…”
“Justine?  Which one’s that, Candy?”
“You know – long sexy gloves…”
“Oh, yes…  Her!  Don’t you dare go looking for her, Tim, or…”
“And there’s Betony…  She’s so pretty, isn’t she?”
“Gorgeous!  And what about…”
“Stop!  That’s enough!”
“Do you think it’ll all be too much for you, darling?” said Candy, archly.  “Naughty boy…”
Tim went to rise.  “Perhaps I should get to work on your boots now…”
The girls grabbed an arm each, and jerked him back into his chair.  The sudden movement was too much for the rubber press-stud.  His fly popped open, and his straining prick in its red latex sheath burst out and stood proud and twitching in full view.  The girls squealed with delight, but made sure to keep a tight hold on Tim’s arms.  Phillipa clapped her hands.
“Ooh!  Look!  You do like us, Tim!”
“You like us a lot,” laughed Candy.
“Oh my god, it’s so big…” murmured Phillipa, biting her lip. 
Candy prodded the shaft gently with one red-painted nail, making Tim squirm with embarrassment. 
“And hard,” she remarked.  She looked up.  “It’s really very impressive, Tim.”
Tim, face burning, didn’t know where to look.  Phillipa plucked up courage, took the head between thumb and fingers and gave it a gentle squeeze.  Tim gasped and wriggled.  Phillipa giggled. 
“Did you feel that, Tim?  Is it really sensitive?”  She slid her hand down and closed her fingers around the shaft.  “Gosh, I can only just get my fingers around it.”
“It’s bigger than Bobby’s, isn’t it?” said Candy.  “We can tell when we see you going to lunch together.”
Tim looked at her aghast.
“I know, we shouldn’t.  But all the girls do it – you know, try to guess the sizes…”
“It must be such fun to play with.  Is it, Tim?” said Phillipa, looking up into his face with the most innocent expression she could muster.
Tim opened his mouth to reply, but managed only an inarticulate stammer.
“He’s embarrassed,” remarked Candy,  “Aren’t you, Tim?  Anyway, Ellie told me…”  She paused, uncertain whether to continue.
“What did she tell you, Candy?” asked Phillipa, eagerly.
“Well…  She told me that the boys play with each other’s.  Is that true, Tim?”
Tim paused.  “N-no…  I mean…”
“It is, isn’t it?” blurted Phillipa.  “Ellie wouldn’t say it if it wasn’t true.  I don’t blame you.  It must be such fun doing it to each other.  Do you c-um when you do that?”
“Of course they do!” laughed Candy.  “That’s all boys want, isn’t it Tim?  They want to c-um and c-um all the time.  They have so much they don’t know what to do with it.  Making you wear these cute red condoms is a great idea.  Otherwise I bet your little shorts would be getting all slimy and sticky all the time.”
She hooked one finger into his fly and pulled it open. 
“Ooh…  It goes right over your balls.  Clever.  Now we know something that none of our friends do!”
Phillipa looked thoughtful.  “So…  When you do it to each other, do you have competitions?  Like who can hold on the longest…or who makes the most c-um?”
“Phillipa…”
“Just tell us!  Please!  Come on.  It’s really interesting!”
“Look, we don’t do it all the time…”
“No?  But I bet you do it a lot!  Who usually c-ums first?”
“You, I bet…” said Candy.
“No!” cried Tim indignantly.  “Bobby nearly always c-ums first, as a matter of fact!”
He had rather given the game away.
“Oh, really?  Nearly always?  How often, exactly, Tim?”
“Let me go!  Please…” he whimpered, pathetically.
We can ask him later,” said Phillipa, ignoring him.  “Do you do anything else together?”
“Anything else…?”
“Yeah.  You know…”
“I should really make a start…”
“Sit still, Tim.  Answer Phillipa’s question.  Don’t you do anything else?”
Tim was getting more and more uncomfortable.
“No…that’s it.  It was just a couple of times, that’s all…”
“Don’t believe you,” said Candy, sing-song.
“What about…” - Phillipa lowered her voice – “fellatio…?”
“What?”
“You know,” said Candy.  And she mimed the activity.
“No!  No we don’t!”
“Why not?  That’s what boys like best of all, don’t they Candy?”
“Absolutely.  They’ll do anything for it.  If you did it for Bobby, he’d love you forever.  I bet you’d be so good at it, he wouldn’t ever want a girlfriend!”
“Look…   That’s not true, is it?  Why do you keep asking me these silly questions…?” 
There was a pause.
“What’s not true?” said Candy.
“Nothing!”
“That Bobby wouldn’t want a girlfriend if you did that for him?  Don’t be so sure, Tim.  He likes you a lot, you know…”
“Not that much…”
“Oh, he does.  It’s pretty obvious, the way he sticks to you.”
“But we’re not gay, so…”
Candy wasn’t letting him off the hook now.  “I didn’t say you were, Tim.  But if someone’s really important to you, and your desperate not to lose them, you do anything, right?”
“’E is important…”
“Do you think he really loves May?”
“May?  No, I don’t fink so…”
“S’pose she takes him away from you, just cos she’s prepared to give him what you won’t?”
Tim looked thoughtful…and slightly anxious.
“Bobby may be a bloke, but his thoughts and feelings are feminine.  You know it as well as anyone.  He’s dying for that dress Miss Poole’s promised him.  And who’s his favourite person?  You.  It may not be something you want to do for him, but I think your love is what he actually craves above all else.”
“Really…?”  He was seriously confused now.  He wanted out of this conversation.  “Okay, girls…look.  Let me do my job, and then…”
“No,” said Candy, decisively.  “We need to do something for you first.”
“W-what?”
“We don’t want you showing off to all our friends like you’ve been doing.  It’s a vicious circle.  They all stare at you, you get aroused, they stare more.  It’s the older women too.  Miss Carthew nearly got unseated the other day staring at you and not looking where she was going!  It’ll all end in tears unless we, er, deactivate you for a few days.  You need to save yourself for that wedding you're going to.  We can use a chastity device…”
“No!  Please!”
“Or…we can drain you of your, er, interest…”
Tim frowned, but didn’t reply.
“Ah, okay.  It’s that then.  Phillipa?”  She nodded towards the parlour door.  Phillippa, who hadn’t relinquished her hold on his coc-k, tightened her grip and stood up.
“Follow me, Tim.”
Candy opened the door, and Phillipa led him in…

[Simonssister]

Chapter 257.


Tim never had a chance.  Phillipa maintained her grip on his boyhood, knowing that the welfare of that appendage was Tim’s greatest concern, and that he would do nothing to prejudice it.  He noticed the addition to the floor at once.
“W-what’s this fing?”
“Think of it as your quiet place, Tim,” said Candy, “a place for little boys who’ve got a bit over-excited and need some time out.  Now, before we introduce you to it, let me get you ready.”
She opened the tall cupboard.  The appropriate accessories were ready to hand.
“We’ll put your knee-protectors on first, so you’ll be comfortable…  There we go.  Now thigh straps…so…  Wrist cuffs…  Good.  Now if you like to go down on all fours…”
A gentle tug from Phillipa was all that was required and Tim went down as obediently as a trained dog.  The girls attached his wrists and knees to the four ends of the cross, and stood up to survey their work.
“Comfortable?”
“Why am I ‘ere…?”
Candy looked at Phillipa.  “Shall I explain it to him?  Okay.  First reason, you can’t go on living in such frustration, Tim.  Look how you are today, just through being close to us.  It’s not fair on you.  I don’t know what satisfaction you get from Bobby or Jessica, but it’s clearly not enough.  Second, we’re tired of you swaggering about outside showing off that erection of yours.  Yes, it’s impressive, but it’s sowing dissatisfaction and jealousy amongst the staff.  Moreover you have a wedding next weekend, and you need to save all your potency for then.  So we’ve decided to help you.”
She reached into the cupboard and pulled out a strap-on - black straps and grey rubber dil-do - and held it in front of his face.
“It’s my turn first with this.  You’ll find it much more pleasurable if you go with it instead of trying to resist.  Either way it’ll be a new experience, I’m sure.”
Phillipa buckled it on for her.  Broad straps around the hips, a slightly narrower one through the crotch.  The dil-do, the smooth shaft tapering slightly towards the slightly thicker, blunt head, quivered as Phillipa tightened the buckles.
“Tight as you like, Phillipa…  That’s it…”
She showed Tim.  He whimpered.
“Please…”
“Oh, you’re begging for it…”
“No…   Please don’t…”
“Phillipa?  Got that gag?”
“Right here Candy.”
The gag was made of cream latex, a pen-is head one side complete with a tiny central hole, a ball, about the size of a squash ball, the other.  At the junction a soft plastic ring with straps attached.  Phillipa pushed the pen-is head unceremoniously between his lips, and buckled it up tight at the back of his neck.  The ball had a small rubber plug at the top.  She pulled it out and used a syringe to fill the ball with condensed milk from a jar.  She replaced the plug.
“There.  I know you like very sweet things.  Enjoy.  You may have to suc-k hard to get what you want, but it’ll be good practice, don’t you think?”  She giggled.
With Tim effectively silenced, the girls could proceed.  They also put on knee-protectors, and while Phillipa knelt down at Tim’s side, Candy rolled a condom over the dil-do, picked up a squeezy bottle of lubricant, and took her place behind him.  Phillipa activated the cameras, and they were ready to begin.

[Simonssister]

Chapter 258.

While Phillipa pulled on a pair of fine transparent latex gloves and knelt down at Tim’s side, Candy popped open the rear flap of his modified shorts.  He moaned, squirmed and tried to pull away, but his bonds held him fast.  He could only rotate his bottom, trying to make her task more difficult, but it only emphasized his helplessness.
“How cute!  Are you impatient for your little dil-do, darling?  Don’t worry – I’m just lubricating it for entry.”  The grey shaft was gleaming with lube.  She put down the bottle and pushed the head gently but firmly between his buttocks.  His attempt to repel it by squeezing them together was quite ineffectual.  The head slipped through easily - there was a moment’s pause as it encountered its goal - Candy pushed a little harder, the head penetrated slowly, and the, with a sudden rush, it was in, eliciting a shocked squeak from its unwilling recipient.
Candy sighed with satisfaction. 
“I’m in, Phillipa.  We should go slowly at first.”
“I am,” said Phillipa, who had already begun massaging Tim’s coc-k, pointing at the floor at forty-five degrees to his belly, as fat and red in its latex skin as a large bratwurst, and twitching with arousal. 
“Squeeze, pull, relax…squeeze, pull relax…  Is that about right, Candy?”
“Perfect, Phillipa.  You have such a good sense of rhythm.  I’ll keep time with my thrusts…  He’s really taking this well…  It’s sliding back and forth so easily…and look - it’s going right in up to the hilt!”
At first, Tim was emitting a faint, continuous whine.  But after a couple of minutes it faded away, and was replaced by a grunt at every thrust.
“I think he’s getting the idea,” she murmured.  “He’s definitely working with me now…  Pushing back as I thrust…”  She raised her voice.  “Good boy!  There, don’t tell me this isn’t the best thing you’ve ever felt…”
“Candy, he’s making so much juice.  The teat’s already quite full.  It’s swinging backwards and forwards as I milk him!”
“Soon perhaps we’ll get some cream to go with it…  Just carry on at the same pace, and let’s see what…”
But she didn’t get to finish her sentence.  Tim gave a sort of choking sob, and then his helpless torso was racked with climactic spasms.
“Don’t stop!” cried Candy, maintaining the steady back and forth rhythm.  “Keep milking!”
Phillipa gasped – she could feel the violence of Tim’s orgasm under her fingers, the sperm being pumped out in great spurts.
“Gosh!  It’s so powerful!”
Her eyes widened as she watched the spherical teat inflating, filling with c-um, in front of her face.
“There’s so much…”

Slowly Tim subsided, amidst little satisfied moans.
“Sounds like he enjoyed that,” smirked Candy.
“Look how much c-um he made!”
Candy peered round.  The teat was hanging down, heavy with Tim’s first ejaculation.  Phillipa squeezed it.
“It’s all squidgy and warm!” she giggled.
“Give him a minute or two, yeah, and we’ll see what he’s got left…  Do you want a go with the strap-on?”
“Maybe one go…  But I like doing this.  It feels so cool when he pops…”

[Simonssister]

Chapter 259.

The girls had a plan, but in any case, it was fun having such complete control over such a big guy, and showing him what real sex was like.  So they continued their work with diligence and discipline, until Tim had experienced three more shuddering climaxes, and the teat on the sheath was as large as a ping-pong ball, and hanging down almost to the floor.  Then Candy finally carefully withdrew, and closed the rear flap.  Tim slumped – as much as he could in his shackles, and sighed faintly.  They were almost finished with him.  But not quite.  The plan, cooked up with Ellie and sanctioned by a higher disciplinary authority, had a pre-arranged endgame. 
Candy divested herself of the strap-on, and retrieved a little plastic box from the cupboard.  Simultaneously Phillipa was removing the long sheath from Tim’s dangling and much shrunken member, carefully so as not to spill any of its precious contents.  She clipped the neck and laid it aside, then cleaned Tim meticulously with baby wipes.

“I’m sorry, Tim,” Candy was saying, holding a shiny steel chastity device, slightly curved, with a pen-is-shaped head, in front of his nose, “but this was the only way we were ever going to get this on you.”
Tim was trying to speak but the only sounds he was making were inarticulate whines of protest.  Ignoring them, Candy knelt next to Phillipa and prepared to fit the device.
“Think yourself lucky.  We did consider a flat one, which would have totally feminised you, but decided for you it would have been impractical.  This one isn’t very long, but at least it’s the right shape, so in your latex shorts you’ll look as though you have a pen-is, though rather a little one.  Now…base ring…good…let’s get you in…lucky it’s shrunk so well…tight squeeze…  There!  Done.  Lock it…  I have the only key, Tim, so you won’t be getting out till I decide…   When, did you say?  Well, just before the wedding next Saturday.  Your little coc-k will be so happy to get released it’ll go wild – especially at the reception, with all those girls chatting you up.  Can’t wait to see the wedding photos!”

She pushed the device into his shorts and closed the front.  Tim was struggling now, but there was no way the girls were going to release him.
“Ellie will let you out in an hour or so,” said Phillipa. 
She moved round to his head and unplugged the reservoir of his gag.
“Good boy!  You must have been suc-king hard – it’s nearly empty.  Don’t fret.  I’ve got something even more delicious for you!” 
And she began to syringe his c-um out of the condom and into the reservoir.  When it was full she re-plugged it and gave it a squeeze, filling his mouth.  His eyes widened.
“Nice?  There’s just enough left to top it up…  She syringed up the rest, and injected it into the gag.  There!  Full again.  Happy suc-king.  See you around, then…”
And the girls simply walked out, discussing the club they were off to that evening…