His Aunt Nicole

[Simonssister]

Chapter 103.

Danielle’s decisive action prevented the day descending into one of those chaotic hen parties which often lead to all sorts of unexpected fall-out.  Her performance, leisurely and composed yet imaginative and thrilling, left Bobby, after a noisy, shuddering climax, collapsed on Tracey’s lap, dazed and gasping.  As the applause died down, she held him tight, stroking his hair and his cheek, murmuring motherly reassurance, till his erection had subsided - then deftly popped it back inside his leotard and zipped him up.  After a few minutes he was able to resume his duties, and his unruly member gave him no more trouble that day.  The wine flowed so freely, however, that it is doubtful that, even if it had, any of the ladies would have been in a state to exploit it.  But Zeta’s video of the episode appeared to have been freely shared, because every time he approached to top up glasses, phones were covered or placed down amidst embarrassed giggling.  Still, what did he care?  That was nothing to the humiliation  he had suffered earlier in the day, and which she had also filmed, the memory of which sent a cold shiver down his spine… 

The party broke up around eight.  Cars were left in the car park for collection the next day, and four cabs were sufficient to ferry the semi-conscious guests and the two maids home.  Miss Poole and Bobby himself slept at the centre that night.
However, before the drinks had taken their fill effect, Nicole had got together with Magda and Clarissa and made plans for the summer.
“Bobby’s going to be busy for the next three weeks,” explained Nicole, “and I want to give him every chance to do himself justice in his exams.  And after they finish, he’s going off camping for a week or two with his mates – so he won’t be available until, what, the end of July probably.  But that gives us loads of time to plan.  Let’s arrange our first meeting in, say, a week’s time.  I’ll talk to Lavinia and Sarah and get Sarah to draw up an agenda.  She’s good at that sort of thing.”
“What about my Zeta?” asked Magda. 
“And the girls,” added Clarissa.  “They’re full of ideas, and they seem to have developed quite a close relationship with Bobby.  They could be very helpful.”
“I agree.  Why don’t we enrol them as associate members.  We should have the first meeting just with the five of us, and then bring them in when we’ve decided their roles?”
“Yes, that’s good,” said Magda.
“I agree,” said Clarissa.
“Right.  I’ll be in touch.  Let’s meet at  my place.  I can show you some of my resources.”
“Resources?”
“You’ll see…”

But thinking the matter over as she lay in bed that night, Nicole decided that of all her friends, the only ones to whom she was inclined to reveal her secrets were those girls Barbara and Kaiya.  For some time she’d been thinking about employing some assistants to help with her increasing clientele, and also to spice up her act a bit.  She recognised what great assets their youth and good looks might be, and their playful, upbeat personalities convinced her that her profession was just the sort of thing they might be into!

[Simonssister]

Chapter 104.

The inaugural meeting of the new, enlarged, Ladies in Boots took place while Bobby was in the middle of his exams.  One Friday morning, Nicole, Lavinia, Sarah, Clarissa, Magda, Zeta, Kaiya and Barbara gathered at Nicole’s house for an open discussion of strategies and goals.  Nicole had brought more chairs into the lounge and they sat in a circle, sipping coffees and soft drinks, with Lavinia with her pen poised over a pad ready to make notes.
“Thank you all so much for coming,” smiled Nicole, looking around.
“Thank you for inviting us, too, Nicole,” piped up Kaiya. 
“No need for thanks, darling.  You two are just what we need.  Fresh blood and fresh ideas.  Now I know it seems a big meeting for one little boy…”
“Maybe we can recruit another one some time,” murmured Clarissa, hopefully.
“Not so little any more,” grinned Sarah.  “He’ll be seventeen in a few weeks.”
“But he still behaves like a little boy…” remarked Lavinia.  “That’s what makes him so cute…”
“That and his pretty looks,” laughed Magda.
“Yes!” cried Barbara, enthusiastically.  “He’s so pretty!  He has a face like a girl!”
“It’s true,” nodded Zeta.
“He could be a girl,” put in Kaiya, thoughtfully.
“Apart from…”
“Yes, of course, Babs, apart from…that.  But I’ve been thinking.  You really don’t exploit his good looks, Nicole.  When he was all made up and in that amazing outfit at Miss Murchison’s party he could easily have been mistaken for a female.  He’d look so cute in a pretty dress, don’t you think?”
“She’s right – we should pursue that idea,” said Lavinia.  “I’ll jot it down.  Mind you, we’d have to suppress his natural…er, talents…”
“That’s easily dealt with, Lavvy,” said Nicole.  “I’ve got a whole range of devices available, as you know.  It’s a good idea.  He needs to get used to exercising a bit of self-control.  And I do wonder sometimes…would he be happier in a more female persona?”
“When’s his dressage performance?” asked Sarah.
“Middle of October,” said Nicole.  “After he comes back from his hols he can hang out with his mates for a couple of weeks before he goes back into training.  So if it suits you, Clarissa, he’ll move to yours around, say, the middle of August?”
“Yes.  Mélisande’s expecting him.  She’s very excited.  She’s been cleaning out his little stable.  We’ve ordered lots of nice fresh hay, and I’ve fixed a new tethering ring low down on the wall.  I keep reminding her it’s supposed to be a secret but she’s itching to tell her friends.”
“Oh dear.  Never mind.  We’ll worry about that later.  So, after the dressage show he’ll be at our disposal.  Well, technically of course Mélisande will still be in charge, but I presume she won’t be countermanding our plans, Clarissa?”
“I think my daughter will be happy for us to take charge,” laughed Clarissa.  “Though she may start to assert her rights in a few years.  I imagine the idea of having a good strong man at her beck and call when she sixteen or seventeen may be appealing.”
“She’s growing fast, isn’t she?” said Magda.  “By next year I think she may be too big for him.…”
“I’m on that already,” grinned Nicole.  “My friends at Fantastex are working on adjustable leg extensions that can be used increase his height gradually by anything up to nearly a foot.  So once we get those fitted he’ll be able to accommodate pretty much any height of rider.  Of course, he’s going to have to get used to them, but it’ll mean he’ll be able to move faster, and pretty much any of the girls at Pitt’s Wood will be able to ride him.”
“Oh my god, Niccy, you’re priceless!” cried Lavinia.  “So it looks like Mélisande can never outgrow him.  She’ll be happy.  But I’m not so sure about Bobby…  You haven’t told him?”
“No.  It’ll be a special surprise.  Maybe his Christmas present…”  She sniggered.  “Now, any other ideas?   What about his boot boy services?  I’ve discussed this with Miss Poole and she wants to provide him with a private room at the Centre and offer bookings to private clients only.”
“Okay…  So what would he be doing, exactly…?” asked Sarah.
“At the moment his duties would be cleaning boots, period.  No hanky-panky.  I’d have him firmly locked up, as well.  That would be a necessity – you know how he reacts to boots.  As to how we dressed him…  Well, we could be as creative as we wanted.  I’m sure Barbara and Kaiya have some ideas.  His customers would pay a small fee, and he’d get, I don’t know, maybe ten or twenty percent.  The rest would go to the Centre.  All very respectable, but excellent obedience training.  That must be our strategy, I think.  By the time he’s eighteen I want him responding to instructions without thinking.  Then we can start experimenting.”
“Good thinking, Nicole,” said Magda.  “He’s a natural submissive.  All we’re doing is giving him what his heart desires, showing him the ways in which he can express his personality.  Right?”
“It’s true,” said Sarah.  “He respects girls and women, but he admires them so much he never wants to take the initiative.  His idea of a relationship is serving them in any way he can, responding to their needs and whims.  That’s when he seems most fulfilled.”
“Yes, and it’s the same with sex,” added Nicole.  “He has no desire to make love to a girl.  He at his happiest when they use him as their sex toy.  Remember Phoebe?  When I caught her pounding him with a strap-on in his stable, he was in heaven!  He’s very confident in other ways – intellectually in particular – but in this area he’s definitely, I don’t quite know how to put it…actively passive!”
“Yes!” cried Clarissa.  “The other day…”  He voice trailed off and she turned bright red.  Everyone looked at her.
“Yes?  Go on,” smiled Lavinia.
“Er…no, nothing…”
“Come on, spill it, Clarissa…”
“It was nothing…er…it was just, you know, one day when he was cleaning by boots…”
“Yes?”
“Well, I just happened to put my foot in the wrong place, and…”
“You naughty girl!” laughed Nicole.  “You made my nephew…c-um?”
“I hardly did anything!  Honestly!  All of a sudden he just went off like a firework!”
“Well, you’d better get used to it, sweetie.”
“What?  What do you mean?”
“Let’s talk about it later, okay?”
“Okay…if you say so…”

[Simonssister]

Chapter 105.

“We need to address his role as a visiting plaything,” said Sarah.  “Not only as a hired maid or pageboy or whatever, but as a surprise present for birthdays and so on.  I see these as two quite separate functions.  In the first case he will need to be dressed and presented to order.  We should offer the customer the biggest possible range of characters and costumes, priced according to cost and complexity of preparation.  In the second case I would hope the person ordering would allow us some extra leeway.  After all, we need to have some fun as well, and it would be nice to be able to use our imaginations in getting him ready.  What do you think?”
“Could we help?  Please…” begged Barbara.  “I’ve been fantasizing about dressing him up as a big doll and putting him in a box with a cellophane front tied up with a bow…  Maybe a Barbie doll…”
“In a bikini!” added Kaiya.
“Yes!  Or a cute little girl doll in a short gingham dress and pretty panties!”
“Or a baby in a big puffy diaper with a giant pacifier!”
“…who wets himself and has to be changed…”
“Or even…  all trussed up in bondage gear with a rubber hood and a gag and…”
“...and a collar and lead and a butt-plug and…”
“Girls!  Girls…  That’s enough.  I can see you’re brimming with ideas”, laughed Nicole.  Yes, I think we should try out all of those, and more.  But perhaps we should work our way up to the more extreme things?  Unless specifically requested, of course.”
“Yes, Nicole, I agree,” said Lavinia.  “But I think the girls have definitely hit on his potential as a female.  I wonder how he feels about it.  I think you should have a conversation with him, darling.  In general terms, of course.  Casually bring up the topic of transitioning…   See what his thoughts are.  Who knows, maybe it would be something that he’d like to explore.  Sometimes I think his pen-is becomes an embarrassment for him, especially as he has so little control over it.”
“Oh, but Lavvy, Bobby without his lovely coc-k?  No, I can’t imagine such a thing.  Everyone loves it, it’s so cute and so unruly.  That’s its charm – it controls him, not vice versa.”
“Silly!  I’m not talking about a sex change!  But…well, don’t you think it would be nice if he had some little boobs too?  Then he could wear a bra, and all those pretty girly outfits that Barbara and Kaiya get to wear, and have his hair styled, and wear pretty makeup…”
“Yes,” blurted Kaiya, “and we’d look after him, and help him with all that girl stuff, and take him out with us…”
“…and pick up some nice boys!” laughed Barbara.
“Yes.  And why not?  I bet he’d be well into that, too.  Don’t you think so, Nicole?”
Nicole laughed.  “Well, since you mention it, no, I don’t think he’d be averse, after what my friend Clare told me…  No, don’t ask me to go into details.  So…it seems we have lots of ideas.  Are we going to put any of them into practice before the dressage show?”
“Why not?” said Lavinia.  “Maybe a trial run or two.  Why don’t we tell Violet he’ll be available for a couple of days in at the end of August or the beginning of September, before college starts?  Would that be okay with you, Clarissa?  And with Mélisande, of course?”
“I’m sure it wouldn’t be a problem.”
“I’ll talk to Violet,” offered Magda.  “I’m sure she can have his premises ready by then.  She’s earmarked one of the disused stables, and it’s already being renovated.  And I believe she has friends lining up for his services, not least those party animals you met before!”
“Poor Bobby,” murmured Zeta, with feigned pity.
“Great.  Then when we know what he’s in for, we can settle the details, and talk costumes,” said Nicole, briskly.  “Now, girls, how about some lunch?”

After the meeting wound up later that afternoon, Nicole asked Clarissa to stay a bit.  Clarissa had been thinking about what Nicole had said, and was looking slightly apprehensive.  Nicole made coffee and they sat down at the kitchen table.
“So, darling…about Bobby.”
“Nicole, you know I’m not very good with boys.  Having one perfect little daughter…I really haven’t had much - or anything really - to do with them…”
“Don’t worry.  You’ll be fine.  Just follow my instructions.  What I’m saying is, since he’ll be in close contact with your daughter” – she grinned – “or at least, with her riding whip! – it’s important he’s kept contained and controlled.  He has physical needs like any other boy of his age.  If he’s going to be spending a lot of time in his pony suit, he won’t be able to do anything about them himself, and you don’t want them boiling over when she’s on his back, now do you?”
“Certainly not!  Goodness!  The very thought…  Nicole, just tell me what I need to do and I’ll do it!  Whatever ‘s necessary.  I would hate to think of Mélisande…”
“Quite.  It’s very simple.  His groom at Pitt’s Wood used to take care of it, but now you’re going to be his groom, at least for his more personal needs, so it’ll be your responsibility.  All you need to do is relieve the pressure every now and then – every couple of days should be enough, but you can play it by ear.  You’ve already discovered how easily he can be popped.  I suggest first thing in the morning – that’s the most critical time, especially if they’ve had torrid dreams.  Also, Mélisande should still be asleep.  If you make it part of the routine, say after toileting, he’ll soon get used to it.  Tether him so he doesn’t try to move around, take it out, and drain off all that excess sperm.”
“You mean…with my hands?”
“Yes.  What else?  I’ve made up a pack with everything you’ll need: gloves, apron, pots, condoms, lube.  When you’ve done, remember to put on one of the heavy red condoms before you pop it back in its pouch.”
“I was never very good at stuff like that…”
Nicole laughed.  “It’s easy.  Once he’s aroused it’ll almost happen spontaneously.  Your people were farmers, weren’t they?  It’s no different from milking a cow.”
“No, I guess not.  Well I certainly know how to do that.”
“Good.  You’ll find it’ll help to pop his tail in first.  That usually gets him going.  Slide it in and out a few times, and maybe give it an extra pump.  And I’ll let you into a secret – it has a remote control vibrator.  Turn that on.  I’ll let you have the app.  Just make sure to turn it off before Mélisande gets on his back!  Otherwise he has a tendency to buck and kick!”
“Really?  How cute!  I might even have a bit of fun with him when she’s not around!” 
“Clarissa!”
“Only joking, of course.  But thank you so for explaining everything, Nicole.  Given his age and so on I suppose maybe I had been a little concerned about Mélisande riding him off into the fields alone - not that he can do a thing all trussed up in that heavy pony suit!  But I feel a lot happier now I know how to deal with him.  Don’t worry, I’ll make sure to keep him nice and quiet and docile!”
“You can always ring me for advice or extra equipment.  In case you want absolute security, I’ll put in a couple of chastity devices, complete with their own fitted rubber sheaths.  Now, that app…”

[Simonssister]

Chapter 106.

It was the second half of August.  The exams were a distant memory, Bobby was back from his camping trip, tanned and relaxed.  The sun had brought out his freckles, and lightened his hair and eyelashes even more.  There was a trace of down on his upper lip.  Nicole observed him approvingly.  He was off to Clarissa’s in a few days.  He was resigned to it, but as yet ignorant of certain other plans that had been made for him.
In ten days it was Eleanor Bowditch’s fifty-fifth birthday.  She was having a little gathering of friends at her house, that was all, but ever since Diana’s party she had been bothering Nicole about Bobby, and eventually Nicole had agreed to send him along – “but he’s not going to be dressed up like a tart like he was before, for you and your friends to grope”
“Oh, of course, Nicole, I didn’t expect…”
“As long as you understand.  You can have him, but it’s strictly “no-touchy” – okay?”
“Yes, yes – absolutely.  I’d just like to have him around, that’s all.  Such a charming boy…”
No, Nicole had other ideas.  She had taken on board what the girls had said at the meeting, and the more she looked at Bobby, the more she thought what a beautiful girl he would make.  To that end, she had ordered a pretty, rather juvenile costume for him, consisting of a sheer white mesh top with a round neck and little short puff sleeves, a pink faux leather pleated miniskirt, sheer white knee-length stockings, and pink Mary Janes.  Underneath, a white training bra and white spandex panties.  For accessories, sheer white bridal gloves with elasticated, frilled wristbands, a pink satin drop pearl choker, and a little white satin shoulder purse just big enough to hold a lipstick, a compact, and a couple of tissues.  What a change from his usual outfits!  The opposite end of the spectrum.  But everyone had agreed it seemed somehow perfect for him.  However, he was going to need some firm control, so that the cute, innocent persona didn’t get tarnished.  So Fantastex had come up with a special harness which would be worn under his panties.  It was essentially a tight white rubber thong with a small lipped aperture at the front to accommodate a chastity device.  The device itself was made of pink plastic and designed to accommodate everything: a little coc-k-tube curled over a balls-retainer, made to be as compact as possible.  Nicole had doubted he would fit in it, but Cynthia had assured her that it was based on the latest measurements which had been taken only a few weeks before.  However, despite trying various strategies, they had been unable to devise a method of concealing it inside his panties without it looking ridiculous, so in the end the panties had been modified with a small circular elasticated hole so that the device could project freely.  Then, in order to make it less conspicuous and to guard against any leaks, Fantastex had come up with a fine white latex sheath that fitted closely over the whole thing, the mouth gripping firmly behind the lip of the thong aperture, so it was all firm and neat and there was no flesh showing.  When Cynthia showed Nicole the finished articles she was delighted.
“Cynthia, you’re a genius!  Even if his skirt does occasionally bounce up – and being leather that shouldn’t happen too often – then all you can see is white satin and white latex!  That intrusive thing of his will for once be nicely tucked away and behaving itself.”
“Well, I don’t know if it will be behaving…  But let’s say even if it’s misbehaving no-one but its owner will know!”
“And I see you’ve added the deportment control,” she smiled, flicking the butt-plug attached to the back of the thong.  “This is an interesting one…”
“Yes.  We call it the “flower”, because it’s similar to a flower on a stalk, even down to the little petals at the end. The back string will disappear between his buttocks, so the flower will be deep inside, and the petals will tickle as he moves, reminding him to maintain a ladylike posture and a graceful gait.”
“And you said you had one other suggestion…?”
“Ah, yes.  Just something cosmetic you might like to try.”  She produced a little gold tube.
“Lipstick?”
“No…  Nipple-stick!”  She removed the cap, revealing a colourless waxy stick.  “Treat his nipples with this at the beginning of the day.  It stimulates the nipples, making them swell and harden.  It may be a bit itchy at first, but it’s ideal if he’s in girl mode.  If possible it should be renewed every four hours.”
“That’s so cool!  Why don’t I know about this?”
“Actually it’s new on the market.  Applied to a woman it can be immensely powerful, even inducing orgasm.  For a bloke?  Well, I don’t know.  No-one’s ever tried it to my knowledge.”
“Bobby’s going to be the first!”
“Okay…  Maybe go easy until you know how he’s going to react…”
“Oh, don’t worry, Cynthia.  You know me…”
“No comment, Nicole…”

[Sandra B]

Nicole is very unfair to her poor nephew.