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11
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on August 12, 2025, 03:40:36 AM »
Chapter 223.

The rest of the afternoon was uneventful work-wise, but Timothy was in high spirits.  As a consequence of his official status as Bobby’s assistant, he had been suffering from a niggling sense of inferiority, a faint resentment.  “I’m as good as ‘im,” he thought.  “Why assistant?  I ain’t assistin’ ‘im.  No – I’m doin’ exackly the same job, an’ just as well!”  However, the discovery that his principal was secretly MĂ©lisande’s little ponyboy had quite restored his confidence.  Every now and then he would chuckle, or shake his head in disbelief, much to Bobby’s irritation, and if he glared at his friend Timothy would simply give him a great big smile in return.  He didn’t need to say anything for Bobby to know exactly what he was thinking.  During one session Bobby instructed him about the use of black polish.
“Remember,make sure to remove every trace of excess, and let it dry for a couple of minutes.  Then seal the leather with a spray lacquer, otherwise it can get on the rider’s clothes.”
“Yes, sir!  Or on a pony’s coat, if he happens to be a little grey one
”
“What?”
“Nothing, sir
”
“And stop calling me sir!”
“Yes, sir
  Oops
”
On another occasion, a lady asked
“Do you ride yourselves, boys?”
Quick as a flash Timothy responded, “No.  My partner has someone else to ride him!”
The lady laughed, appreciating the smart answer but not getting the full joke.  Bobby did, though, and wasn’t amused.  But Timothy simply couldn’t help himself.  It was going to be a while before the novelty wore off


He was still teasing Bobby that evening after work, as they sat in their living-room sharing a pizza.  Bobby, after several hours of ribbing, was in a foul mood and near to breaking-point.  In fact he was at the stage of giving his friend a cuff round the ear, when his phone buzzed.  He snatched it up with a snort of irritation, but as he read the message and saw the attachment all his frustration evaporated.
“Hi Bobby!  We had a great time today.  [heart]  Thank you so much – and specially Timmy!!  And for the video.  Thought you might like it for your records! [laughing emoji, hearts] xxx Bethany”
Bobby forgot about his pizza and sat back in his chair, smiling.  He turned off the sound and played the video, sniggering occasionally.  Timothy stopped chewing and stared at him.
“What you smirkin’ about, ponyboy?  Lookin’ forward to Sunday, are you?”
Bobby kept watching the video.  “Not right now.  This is much more entertaining
”
“Wha’?  Wha’ is it?”
“Just some guy about to pop
   Ooh, there he goes now!  Wow!  What a performance!”
He held up his phone for Timothy to see.  He saw, swore, and made a grab for it.  But Bobby was out of his chair and locked in his bedroom before Timothy could get to him.
“Gimme that phone!” he shouted through the door, rattling the handle.
No reply.
“Bobby!”
“You can have it just as soon as I’ve uploaded this to the cloud
”
“You better not!”
Silence from within.
“Too late!  Okay, I’m coming out.”  He opened the door.  “Shall we watch it together?”
“Shu’ up!”
“Okay.  But you shut up too.  If you go on about you know what any more, I might be inclined to circulate this.  I wonder
  I bet Serena would be very amused
”
“Don’t you dare!”
“Pact?”
Timothy frowned.  “Okay
  Pact.”
“Good.  Are we good again?”
“Guess so
”
And with a yell, he jumped on Bobby, and the two of them wrestled, laughing, on the floor till they were exhausted.


The thing about Diana Murchison and Eleanor Bowditch was that you rarely saw one without the other.  They seemed to do everything in tandem.  So much so, that the staff sometimes got their names mixed up, and talked about “Diana Bowditch” or “Eleanor Murchison”.  There was something in their looks as well, such that they could easily have been mistaken for sisters.  Eleanor was a few inches taller than her friend, however, and though they adopted rather similar, simpering expressions, Eleanor, to her credit, lacked Diana’s sly and calculating glance.
They even shared a house, something which had given rise to quite mistaken notions about their sexuality.  True, they both had a keen and prurient eye, but its gaze rested exclusively on the male of the species.
After their meeting with Cynthia, they had taken themselves off for several coffees and worked out their strategy.
“This is what I think, Eleanor.”
“Yes, Diana?”
“We have two sessions booked.  I suggest we use the first to gain their trust, so that our plans for the second will be easier to put into practice.”
“I agree, dear.  Those pageboy outfits
  Adorable!  How does she think these things up?”
“She’s a woman after our own hearts
”
“Absolutely!  Er
  Did you check the special locker?”
“Oh yes.  Violet gave me a tour, and lent me the key.  There’s everything we need.  Whips, gags, straps
  It’s an Aladdin’s Cave
”
“Excellent!  What fun!  And we have a double session, too
”
“That should give us enough time
  And we can always book them for a home visit.”
“Oh, we must.  Yes.”  Eleanor paused.  “And so
do you think they really are
?”
“Gay?  Ninety percent sure.  No girlfriends
”
“But they’re much too busy
”
“Nonsense.  They’d make time if they really wanted to.  Close friends for years.  Used to go camping together.  Shared a tent.  Scouts, I believe
”
“Timmy still is, isn’t he?”
“Not sure.  Anyway, now they’re living together.  In that cosy little pad Violet furnished.  Stroke of genius, that.  Then there’s the latex
”
“That wasn’t their choice though
”
“Maybe not.  But they adapted so easily.  They look so comfortable in those costumes.”
“That’s true, Diana.  Comfortable is right
  And very sweet
”
Diana licked her lips.  “Very
  Violet told me that Bobby’s really into the pageboy look.  Apparently he was hoping to be a pageboy at some wedding next month.”
“Really?”
“Yes.  When he heard about the outfit he pleaded to be allowed to be pageboy to the bride!”
“Wow!  Did he know what the outfit looks like?”
“Oh yes!  He’s desperate to show it off.  He craves attention, you see.  He’s got such a large streak of vanity.  But it’s quite innocent.  That Burlington girl has him right under her thumb.  You know how?  Not by punishing him, but by praising him.  So I’ve been told.  “Good boy, Bobby – you’ve done really well today.  Here’s two sugar lumps
”  Really!”
“Oh, Diana
  That’s so cute.  What a little darling.  Well, I think we know what we need to do.  If we can make it easier for them to come out, I’ll feel we’ll have helped smooth the path of true love
”
“Yes, Eleanor.  “Yes, Eleanor.  And it will add spice to the Christmas party.  But let’s not tell the girls yet.  Let’s wait and see how things transpire
”
12
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on August 11, 2025, 06:44:49 AM »
Chapter 222.

Bethany and Natasha, having had their fun, decided it was time to go.
“We’ll leave you then, Bobby.  Look after Timmy, won’t you.  And we’ll see you Sunday, yeah?” grinned Natasha.
“Sunday?  I’m not sure if
”
“No.  You’re free.  We checked.  Ellie will explain everything,” said Bethany.  “See you guys, then
”  And they gave little cute waves as they left, as if they had just done nothing more than visit for coffee.
Bobby stood staring after them.  “These women
all of them
they really are
”
“Bobby
” groaned Timothy.  “Can you ‘elp me next door
?  I’m totally knackered, mate
”
“Of course.  Quick, before the next customers arrive.”
He helped Timothy to the apartment, and left him lying face down on his bed. 
“Don’t worry.  I’ll handle the next session.  I’ll be back lunchtime.”
“Fanks, Bobby
”

Bobby returned to the waiting room and cleaned up.  He had just finished when Ellie poked her head in.
“Next two on their way.  Ready?”
“Yeah.  It’s just me.  Tim’s er, not feeling well
”
Ellie somehow kept a straight face and feigned ignorance.  “Really?  What’s up?”
“Oh
nothing much...headache, I think.”
“Right-o.  Well it’s only a couple of the part-timers.  Rubber boots.  You shouldn’t have any problems.”
“Thanks
”

He had them cleaned and polished within forty minutes, and would have liked them to leave.  But the girls, who were around his own age, insisted on hanging around chatting him up, till to get rid of them he had to agree that he and Tim would go out for a drink with them when they had a free evening.  He didn't mind, actually.  The dark one, by the name of May, was rather cute, he thought...  It was nearly twelve by the time he returned to the apartment.

Ellie had got Timothy up, made him have a shower, and washed and dried his pants.  He was fully recovered – and hungry.
“Come with me to the canteen,” said Ellie.  “I need to update you.”
“Can we change, then?” asked Bobby.
“No.  Miss Poole very clear about that.  When you’re working you keep your uniforms on all day.  You can slip on a jacket if you’re cold.”
“Okay
”  There was no point arguing.  So they put on their official Pitt’s Wood hoodies and accompanied Ellie up to the buildings.  They attracted quite a lot of attention queuing in the canteen, but eventually they got their lunches and got seated.
“So
 Bethany and Natasha,” began Ellie.  “Any problems?”
Bobby looked at her.  How much did she know?  He couldn’t tell.  Timmy blushed and looked down.
“No, no problems.  They got what they wanted.  Said they’d leave us a good review in fact
”
“Oh, good.  Now, this weekend.”
“Yes?”
“Saturday you got a couple of specials
”  She looked at her diary.  Two o’clock and three o’clock.”
“Who are they?”
“Outsiders.  No idea.”
“What about tomorrow?”
“Two specials first thing.  Nine to ten-thirty.  Committee members.  You need to give them particular attention, obviously.”
“Committee members?  Who?”
“You’ll find out.”
“Why won’t you tell us?”
“You don’t need to know.  Just do your work.”
“We’re not slaves, you know
”
Ellie smiled.  “Aren’t you?”  She paused, cheekily.  “So, as I was saying.  Sunday.  Miss Poole wants you here at one.”
“Okay.  Fine.”  That will get me out of being a pony for Charlotte and Amelia, he thought.
“Yes.  Cynthia wants to do a final fitting for your pageboy outfits.  You’ll be wearing them for at least the next two weeks.”
“I see
okay
”
“But before that
” 
Ellie had a particularly evil smile on her lips.
“Yes?  What?”
“Before that
  The junior arena’s closed
  And I understand that two of MĂ©lisande’s best friends are dying to try out Bobby the Pony
”
“No!”
“
and the arena’s the perfect place, don’t you think?”
“No!  That’s not fair!  I won’t
”
“Won’t?”
But Timothy had awoken from his reverie.
“What’s that about Bobby the Pony?  What are you talking about?”
“Oh, Timmy!  Didn’t you know?  Bobby here
”
“Shut up, Ellie!”
“Bobby’s also Bobby the Pony!”
Bobby clapped his hand to his forehead.  Timothy’s mouth opened as he began to take in the significance of Ellie's words.  His forehead puckered.
“Bobby...?  You tellin’ me...‘e’s that pony what that little girl rides?  Is that true, mate?”  A smile was spreading slowly over his face.  “It is, aint it?  It’s you!  I should ‘ave realised, shouln’t I?  That explains everyfing!  No wonder you’re so nice to ‘er!”  He was convulsed with laughter - he could hardly speak for laughing.  “You
an’ ‘er!  What a pair!  Oh my god.  Perfick!  Bleedin’ perfick.  “Oh, mate, the way she whacks you wiv ‘er little stick!  Priceless!”  He took a breath and collected himself. 
“So
  Ellie
  Am I gonna get to watch this as well?”
“If you want
of course.  In that case there’ll be you, me, Miss Poole, Cynthia from Fantastex, oh, the girls’ mothers of course, who you serviced this morning, MĂ©lisande’s mum, Bobby’s aunt
  I think that’s all
”
“I can’t wait
I can’t bleedin’ wait
  Oh, mate!  Why didn’t you tell me?  You didn’t ‘ave to keep it such a secret, y'know, not from me
  Now I know
”
“Okay, you know.  Now shut up sniggering.  And if you tell anyone, I’ll bloody kill you!”
“No, you can’t tell,” said Ellie, “or you’ll be out on your ear.”
“I know, I know.  I don’t wanna tell anyone.  It’s enough.  My best mate Bobby is ‘er little pony.  Bobby, mate, you must tell me all about it – ‘ow it feels being a good little pony, ‘aving you bum whipped and them little spur fings diggin’ in yer ribs
  Do yer like it when
  ‘Ow!”
Bobby had given his friend a good hard kick under the table.  But it only made him laugh louder, till the whole canteen was staring



13
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on August 11, 2025, 04:49:29 AM »
Chapter 221.

They heard some brief words between Serena and the waiting guests, and all at once they started to panic.
“We can’t let ‘em see us like this!” hissed Timothy.  “Who is it, anyway?”
“Dunno, Tim.  Doesn’t matter who it is, if they clock the state of us we’re done.  We’ll get reported to Miss Poole, and you know what that means!”
“’Ave a look!  These things ain’t gonna disappear any time soon, are they?”
Bobby crept to the door and opened it a couple of inches.  Two women, chatting.  He couldn’t see either of their faces at first.  Then suddenly the one farthest away, the dark-haired one, stuck out her head.  He nearly fainted.  Natasha, Amelia’s mother!  So the other one

But Bethany had already turned.
“Bobby!  It’s us!”
Before he could shut the door they were on him.  With a squeal of fear he retreated to the back corner of the room, by the chairs.  He shut his eyes. 
“We’re finished.  I’m finished!” he was saying to himself.  “It’s all over.  Mellie’s gonna go mad at me when they take her friends away!  Oh, god, Ellie
  Why did you have to
”
“Boys!” cried Bethany.  “Surprise!  We’ve tracked you to your lair.  Miss Poole fitted us in.  Isn’t that kind?  And we’ve both put on our best boots.  I hope you’re going to give us a good service.”
Bethany had apparently already embraced Timothy, and now she was approaching him.  Natasha had her arms around Timothy now, and a strange rather pleased expression on her face.  Then Bethany grabbed him and held him close.  He felt his hard coc-k being squashed against her tummy, and waited for the shock and repulsion.  But it never came.  Indeed, she seemed to want to prolong the embrace for as long as possible.
“My turn, Beth
come on.”
Then Natasha took her place.  She had his back to the wall, her cheek next to his, and her hands on his bare waist.  Then she slid one hand behind him, cupped in over his bottom, and pulled him against her, rocking gently from side to side as if they were dancing, making his slippery coc-k slide from side to side in his pants!  If he hadn't been so shocked, he would have c-um on the spot. When he was eventually released, he and Timothy looked at each other in disbelief.  Had they not noticed, or
?
The ladies took their seats side by side in the chairs.  Bobby quickly revised his view of the girls’ mothers.  At the same time it dawned on Timothy that these women were not the straight-laced, family-oriented, virtuous ladies he might, in his innocence of older women, have expected.  It was a valuable first lesson for any young man – that heightened sexuality is not the domain of youth alone.  Such was their composure that Bobby even wondered whether Serena had forewarned them


Bethany reclined in her chair and regarded them with approval.  “Stand there boys.  Let’s have a look at you.  Come on, hands behind your backs, like soldiers at ease.  That’s it.  Well, you are a fine pair.  Those uniforms!  So cute.  Don’t you think, Natasha?”
“Absolutely, darling.  What a pair of sweeties!  Let’s have few snaps, shall we?  Right.  Here we go.  Smile, boys!  Bigger smiles!  Pose – pretend your boxers, or athletes – show us your muscles.  And the other ones, Timmy!”  [giggles]  “I know!  Hold hands!  Hold both hands!  Yes...”
“Now, turn around,” said Bethany.  “Right around.  Look over your shoulders and smile.  Amazing!  That’ll be a good one for the album, Natasha, yeah?  Okay, now we want some with us, yes?  Timmy, could you take one of us with Bobby?  Then we’ll have one of us with you.”
They went into the waiting room.  Bethany and Natasha stood either side of Bobby, with their hands first on the lower back, but then migrating to his bottom, where they patted and fondled familiarly, making his throbbing coc-k twitch and ooze, till he could feel his juices slippery under his leg-bands.  Timothy snapped away till they were satisfied - which took some time.  Eventually they released him, and then it was his turn to photograph Timothy in the same situation.  It was clear by now that they weren’t here to get their boots polished, but simply to lech over them, and collect as many photos as they could, for what purpose he preferred not to speculate.  It was twenty to eleven already.  But after five minutes or so he got tired of taking photos, and switched to video.  This proved a prescient move, in view of what occurred next.  He couldn’t see what was happening behind Timothy’s back, but Bethany and Natasha were giggling like schoolgirls and he was wriggling and squirming, struggling to escape from their embrace.  Back in reception, though, they had a perfect view of the women’s straying hands.  By now Ellie and Miss Poole had joined the little audience, and Evelina at least was shocked that two mothers of young children should be capable of such lubricious behaviour.
“Look what she’s doing!  That blonde one!”
“Naughty girl,” murmured Miss Poole, with a slight smile on one corner of her lips.
“But Miss Poole
”
“Boys will be boys, grown ladies will sometimes be naughty schoolgirls.  Don’t worry, I’m sure the boys can cope.  It won’t be the last time, I can tell you
”
From behind, Bethany was sliding two fingers rhythmically back and forth against Timothy’s crotch, whilst her friend alternately fondled, tickled and slapped his bottom.  Timothy resisted valiantly, pressing his thighs together as hard as he could, but to no avail.  The fact was that, despite all his bravado, his experience of women was extremely limited, whilst his attraction to them was disarmingly intense, leaving him little defence against such a concerted two-pronged assault.   A trickle of clear fluid was issuing from the right leg of his trunks, which soon became a drop dancing on a sticky string as he struggled.  Then all of a sudden his resistance collapsed.  He gave a sort of choking sob.
“Oh
oh
  No, please stop
  I’m gonna
ahh
.!”
With a moan his eyes closed, his head fell onto Bethany’s shoulder, and he was overtaken by a shuddering climax.  The trickle of juice on his thigh was overwhelmed by a sudden efflux of c-um, which burst forth and streamed down his leg and over his red superhero boot.  He hung between his tormentors, jerking and gasping helplessly in the intensity of his climax.  The ladies, instead of showing concern, exchanged satisfied glances, and wrapped their arms around him in support – which was just as well, for otherwise he would probably have collapsed.  Bobby, despite feeling slightly guilty about it, never stopped filming.  (Later he was glad he didn't, because it earned them a sizeable tip!)  It was only when his spasms finally subsided, leaving him twitching and gasping, that they helped him to a chair and comforted him.
“Timmy
what happened?” asked Bethany, with feigned innocence, suppressing a giggle.
“Gosh, Timmy,” smiled Natasha, “ now that was worthy of a superhero!  Do you feel better now?”
“Was it that pretty lady in the red boots that got you into such a state?  I wouldn’t be surprised.  And she did warn us you boys were a little, er, tense
”
“I-I’m sorry
” said Timothy, weakly.  “I didn’t mean to
”
“Never mind, Timmy.  Forget about our boots – it’s too late for that now.  We’ll just book another session.  And don’t worry - we’re going to leave you guys a big tip – and the best review.  In fact I’d be surprised if Miss Poole didn’t give you a bonus!” 
And they burst out laughing.
14
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on August 11, 2025, 04:22:51 AM »
Chapter 220.

When the idea of her visiting the boot parlour had been mooted by the stable lasses, Serena had known little about either of the boys beyond the fact that they were rumoured to be pathetic little perverts recruited by Miss Poole either as a joke, or for profit, or possibly to satisfy her own weird tastes.  She didn’t have a high opinion of men, and it would have taken quite an exceptional individual to interest her in anything but a one-night stand, and in any case her idea of good sex always involved her taking complete charge, which no-one she had dated so far had been very keen on; so the idea of humiliating a couple of submissives really appealed.  When it later transpired that the boys had apparently been coerced, and that their employment at Pitt’s Wood may not be entirely voluntary, it merely added spice to the project.  What she hadn’t expected, however, was that she should find herself so aroused by the experience.
Each of the boys was stimulating in a different way.  Bobby was clearly a fetishist whose deepest sexual feelings were attached to latex, leather, boots and servitude.  Timmy was a pretty normal young guy with a vulnerability to pretty women.  Thus she found Bobby fascinating as a potential reciprocation for her own desires, and Timmy as an amusing subsidiary project.  As they laboured innocently at her feet, she was already making plans for their future employment as her own minions.  The concurrence of such thoughts with the sensations produced by the boys’ hands palpating her thighs was making her wish she had put on her dil-do pants after all.  But there was nothing she could do now.  She was determined to keep her excitement a secret – its discovery would mar her façade of cool disinterest and aloofness.  And she was also adamant neither of them would be allowed any sexual release.  No, there would be no orgasms today, however steamed up they got.  She knew just how to handle them.  She would leave them at the end of the session in a state of longing and frustration, thinking about her, dreaming about her, obsessing about her.  Over the coming days or weeks she would scatter a few crumbs of attention, till she had them both feeding out of her hand.  Only then would she be in a position to take total control


Soon the thigh section of her boots had been completed, the moist leather revivified and glowing, and she resumed her seat, spread her legs once again, and instructed them to continue.  Bobby carefully unbuckled her spurs and put them to one side.  Timothy followed suit.  Bobby worked from the toe upwards, saving the most delicious part of his labour, Serena’s tightly-sheathed calves, for last.  He used a little brush to apply cream to the stitching and the heels, and creamed and polished her feet with the greatest care.  Applying the thick white cream reminded him of an incident many months ago at his aunt’s house, which had initiated his whole career to date.  He gulped.  As he moved up onto her ankles, and then her calves, his excitement mounted – to the point where the lightest pressure on his erection, now quivering like a tuning-fork, would have produced an explosive climax.  He bit his lip and fought off the temptation.  His coc-k had never felt so vibrant, and he guessed there must be external physical forces at play.  He had noticed the lube Ellie had used that morning didn’t have the usual pine scent, but a definite fragrance of roses.  He looked sideways at his friend, and noted that his rampant erection was even more impressive than his own, and that his hands were still shaking slightly as he worked.  It was probably as well that they were unaware of Serena’s own state of arousal, or the session may have ended less peacefully than it did


But all good things come to an end, and they were awaken from their erotic reveries by Serena’s voice.
“Goodness, look at the time.  Are you finished, boys?”
“I’m almost finished,” said Bobby – which was true in every sense – as he rebuckled the last spur, which he had polished till it gleamed.
“I’m leaving a little tip on the side here,” she said, taking some notes out of her purse and slipping them under the protector box.  “You’d better split it equally - you were both equally proficient, and equally cute!  But I really don’t want to lose touch with you guys before by next appointment.  Could one of you let me have a phone number
”
Timothy leapt to his feet, oblivious of the blunt protuberance straining at the front of his little yellow pants, as if eager to attain the object of its veneration.  “Of course, madam
miss
”
“Oh, thank you, Timmy.  Let me call you
  Put it into my phone, would you
  So
  I think I can hear it ringing somewhere.  Great.  Now we can keep in touch.  But I really have to go.  I believe I can hear your next visitors in the waiting-room.”
She opened the door a crack and peeped out.  “Yes.  Two pretty ladies.  Lucky boys.  Come here.”
To their absolute astonishment and delight, she bestowed a little warm kiss, sticky with lipstick, on each boy’s cheek!
“Don’t forget me, will you?”
“No miss!”
“Of course not, Miss Egerton!”
And with a little mischievous wave, she slipped out.
15
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on August 11, 2025, 04:16:16 AM »
Chapter 219.

When the boys entered the waiting-room, they really had no idea what to expect.  They had both constructed an image of Serena Egerton in their minds, but nothing could prepare them for the actuality.  For Evelina, Gabby and Jasmine, watching proceedings in reception on CCTV, their reaction elicited screams of hilarity.  On their entry, Serena had risen from the chair in which she had been sitting. 
“Good morning, boys.  I’m Serena
”
Bobby was struck dumb.  He stood there, staring, his mouth opening and closing with the desire, but not the will, to respond.  Whatever he was expecting, it was not this – a stunningly pretty young woman, clad from – if not head, at least neck – to toe (so he assumed) in a perfectly-fitting catsuit of glossy black latex, wearing the most breathtaking boots he had ever seen, in his favourite soft red leather, with heels, and fetishistically peaked tops hugging her legs with tailored perfection!  They were not really riding boots, yet she had chosen to wear a pair of little silver spurs strapped to her ankles, which for Bobby was the coup de grĂące.  She had apparently been listening to music – her headphones were now around her neck.  He gulped and tried to recover himself.
“I
I
  that’s to say
h-happy to m-make your
”
He stammered on helplessly.  But Timothy was if anything in a worse state.  All his bravado had evaporated in that first second.  He was seized with fright, and actually took a pace backwards and laid a hand on the door handle.  But he couldn’t have escaped had he tried, Ellie having locked the door – just as a precaution.  He had rehearsed a variety of patronising chat-up lines, suitable for the sort of girl he stupidly imagined he would be dealing with – one who had dedicated her lives to ponies and horses, and had even less worldly experience than he himself.  Even from his brief acquaintance with Pitt’s Wood he should have known better, but his egotism had got in the way.  Confronted with a patently worldly young woman, with a flirtatious expression and disarming looks, wearing just about the sexiest outfit he had ever seen, he simply deflated like an untied balloon, and actually experienced his first ever panic attack!  He started to tremble.  The colour first drained from his face, then, under Serena’s amused gaze, he tuned bright red.
“So you are Bobby
” continued Serena, pointing a latex-sheathed finger.
“Y-yes, m-miss
”
“So this must be Timmy
”
Timothy being unable to reply, Bobby came to his rescue.  He licked his dry lips.
“Y-yes, M-miss Egerton.  Timmy
  Yes
”
“Well you’re both much more handsome than I’d realised.  I only got a glimpse of you at the show, and I was in the back row, so
  And what sweet outfits!  May I
?”
She advanced on the terrified boys and plucked at their latex trunks with professional interest.
“This is excellent quality!  Quite as good as mine – feel.”
She held out an arm.  Bobby looked alarmed.
“Go on.”
Now she was closer he could smell the heady scent of warm latex, and the sweetness of boot leather.  He touched her arm quickly, his heart missing a beat.  He felt dizzy, and he could hardly breathe. 
“Are you all right, Bobby?  Why don’t we go into the parlour?”
“Y-yes
okay
”
As he moved towards the door, she gave him a little pat on the bottom.  Then she took Timothy’s hand, as if he were a child, and led him after Bobby.
“Love your costume, Timmy.  Do you like the idea of being a superhero?  I have a kid brother, and he’s got a Superman outfit, but it’s not a patch on this.  Not from where I stand, anyway.  Latex is so cool, don’t you agree?  I wear latex as much as possible.  I love the way it hugs my body.  It’s great for riding, ‘specially if it’s raining.”  She looked into his face.  “Don’t be shy, Timmy.  I don’t bite, you know – not unless you do something you shouldn’t,” she added, with a wink.

Timmy looked dazed.  Serena got them both inside, closed the door, and seated herself in one of the chairs.
“Mmm, this is very comfortable.  I won’t want to get up.”
The boys stood awkwardly in front of her, not knowing what to say or do.  She looked from one to the other.
“I feel totally spoiled.  Two gorgeous guys, in cute little latex outfits, both trained boot boys, and all I have to do is relax in this nice chair while you dedicate the next hour of so of your lives to pampering me.”
The boys looked at each other, desperately trying to work out what they should do next.  To make matters worse, they were both conscious of a growing arousal.  “Shit!  Not now, please
” thought Bobby.  Serena decided she would have to take the lead.
“So what I suggest is that you attend to one boot each, and I’ll give a reward to the one I think has done the best job.  Bobby, what creams and polishes do you have?”
Bobby roused himself from his inertia.
“Oh
yes.  W-well, we have a range.  But to judge from the quality of the leather
” – he took a deep breath, trying to calm himself – “
which is, well, amazing
  I would use the white leather cream.”
“Yes, you know your stuff, I see.  I use that myself.  But I won’t have to any more, will I?  Now I’ve got you guys, I mean.  I’ll have to arrange for you to visit me at home for some private sessions, yeah?”
Bobby gasped.  Timothy shivered.  But they both nodded eagerly.  Bobby, aware of growing pressure in his pants, quickly put on his knee-pads and dropped to his knees.
“Would you mind lifting your legs a second, Miss Egerton?  Thank you.”
He folded up the foot-rest and used the side-lever to adjust the height of the chair, until her heels were comfortably on the ground.
“There.  Timmy, come on
knee-pads
”
Timothy, flustered, fumbled with his knee-pads.  Serena stole a surreptitious glance at his trunks.  Yes, it looked as though Ellie had done her work, all right.  This was going to be fun
  She spread her legs wide, giving the boys plenty of room to work, and disconcerting them even more.  She was feeling horny now.  They were such cuties, and pretty soon that lube should be taking effect
  Well, she was happy to wait for developments.  She put her headphones back on and leant back in the chair.

Bobby opened a new packet of card leg-protectors, put it down between them, and went to insert one down between the top of Serena’s right boot and her thigh.  His erection was bigger now, and impossible to disguise.  He hoped Serena wouldn’t look down - but where else would she look?  He felt he was now mentally calmer, but his body wasn’t obeying his mind.  He had to lean right forward to wrap the strip around her thigh – it was barely long enough.  Serena lifted her thigh slightly to help him.  There was a discreet zip at the back, running from the crook of the knee to the thigh, and he had to unzip the top couple of inches to enable him to get it in.  As he zipped it up again, he was able to appreciate the quality of the leather – so fine and supple than it even had a degree of stretch, which allowed it to fit her legs so snugly.   Before he had got it fully in place, she lowered her leg and slid her foot forward a few inches between his thighs, so that her shin came into contact with the front of his pants.  He gasped and blushed scarlet.
“Oops, sorry, Bobby,” she smirked, making no attempt whatever to withdraw her leg.
He could hardly stop what he was doing, so he was forced to complete the difficult operation with his hardening erection pressed firmly against her leg.  Out of the corner of his eye he could see Timothy was having the very same problem.  His hands were shaking so much he could hardly hold the strip of card, and Serena, apparently intent on making things worse, was tapping her foot in rhythm with the music!
Finally Timothy got it partially in place, and was able to pull back slightly.  But Serena had no intention of letting either of them off the hook.  She thrust her feet further forward between their thighs.
“Here - why don’t you sit on my feet?  It’ll help you reach the tops, and then you can work your way down.”  But seeing how pathetically nervous they were, she relented somewhat.  “I know, why don’t I stand then while you attend to my thighs?  Then I can sit down again while you do the rest.  Okay?”
They nodded, relieved.  She stood up and planted her feet wide apart.  Back in reception the girls were squirming with delight.
“Off you go, then.  Work the cream in thoroughly, won’t you?  Nice gentle circular movements.”
“Yes, miss,” replied Bobby.  We know what to do.  I’ve been cleaning my aunt’s boots for years.”
“Really?  What a good boy.  I think maybe I should kidnap you and keep you as my personal boot boy.  Would you like that?”  She raised an eyebrow, and glanced at his bulging pants.  “You look as though you might
”
Bobby blushed again, and to avoid further conversation got quickly to work.  She smiled down at them fondly, kneeling at her feet in their aroused state, dutifully servicing her boots.  She took out her phone and began filming.  The feeling of their fingertips on her thighs as they carefully massaged the white cream into the soft leather was highly erotic. She took a deep breath.
“Take your time boys
  We’ve still got nearly an hour.  That’s it, Timmy, take care with the zip flap.  That’s right
  Good boy.
They did indeed take their time, much to her satisfaction.  As they did their work, they both began to relax a little.  Bobby used the task as an excuse to get his face close to her thigh, the muscles taut and firm under the fine latex, the scent filling his nostrils and making his coc-k ache with longing.  Timothy had decided that his erection bespoke an instinctive empathy between he and Serena, and indicated an inevitable future relationship.  He no longer tried so hard to conceal it, but rather hoped she would take it as an indicator of his unusual masculinity

16
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on August 11, 2025, 03:58:51 AM »
Chapter 218.

We’ll leave the boys’ reaction to the reader’s imagination for a brief moment, to catch up on developments elsewhere.
The previous day, Wednesday, Charlotte and Amelia’s visit to the tack shop, with their mothers, MĂ©lisande and Clarissa, had realised the first element of their dreams.  MĂ©lisande had helped them select boots, breeches, shirts, T-shirts, waistcoats, jackets and helmets.  And Clarissa had made their happiness complete with gifts of whips, spurs, and Pony Club ties.
“You should definitely be enrolled in the Pony Club, girls,” she smiled.  “If you train hard, in a few weeks you’ll be able to enter competitions.  It’s great fun.  I’ll help you with the applications when we get home.”
“Thank you so much, Mrs Burlington!” cried Charlotte.
“Yes, thank you.  We’ll work really hard – we promise!” said Amelia, assuming a determined expression.
Charlotte turned to MĂ©lisande.  “Will we be able to wear these to Pitt’s Wood at the weekend?”
“Of course, Charlie.  We can all go and I’ll introduce you to the ponies.  They’re so funny!  Especially some of them
Freddie for instance
”
“Yes,” interrupted Clarissa, “and we’ll get you signed up as official members, which means you’ll get a badge and ID and you can go there any time, even if you just want to get a drink in the cafeteria or wander around.”
“It’s gonna be so great
” sighed Charlotte.  “Like a whole new life
”
Amelia’s eyes were sparkling.  “Mellie
?  On Sunday
  Will we get to
you know?”
“Bobby?”  She looked at her mother.  “Mum?  Sunday?”
“Unless he’s too exhausted.  He must be finding it hard.  His first week in a full-time job.  That’s a point, actually
  He may even be working part of Saturday.  It’s in his contract.  So you might even see him then.”
“I hope he won’t be exhausted
” murmured Amelia.

That evening, after Bobby had appeared in front of the committee for his fitting, Diana Murchison approached Cynthia and introduced herself and Eleanor.
“You do an amazing job, Cynthia.  These outfits you’ve designed – so beautiful, and so imaginative!  And always perfectly tailored.”
“Well, I just love coming up with ideas.  But it’s my wonderful staff that perfect them and produce the finished product.  I’m glad you like them.”
“Nicole tells me that the next ones are virtually ready
”
“Yes.  The pageboys.  I had to make one for Bobby, anyway, as he’s pageboy at a wedding next month.  So I thought we might as well test them out here.”
“I was wondering how long the boys will be wearing them
”
“Oh, at least two weeks, starting next Monday.  There are new concepts in the pipeline but we're nowhere near finalising them.  Why do you ask?”
“Well, Eleanor and I have a session booked this Friday, and there’s been a cancellation on the twenty-fourth which we’re going to book as well, so we were thinking
”
“Oh yes, they’ll be pageboys that week, definitely.  I do hope you approve.”
“Er
what are they like
if it’s not being nosey
”
“Not at all.  Well, I’ll tell you what I was aiming for
”  Her enthusiasm and desire to talk about her creations was obvious.  Diana looked sideways at Eleanor and briefly raised her eyebrows.  “I thought, “now what do I want?”  Well, first, smartness.  So short, nicely-fitting boy shorts in lovely shiny red latex, coupled with plain cream or white spandex shirts with high necks and long sleeves, and a red vinyl baseball cap.  Maybe a choker, plain red ribbon.  Second
  Well, you know the boys.  They’re grown-up now.  And grown boys have a habit of being a bit too macho, always swaggering around showing off, right?  So maybe for sessions we’ll have them made-up with sparkly eye-shadow, white mascara, and pink lipstick, and little round pink circles on their cheeks.  Optional extras, pink ball-gags.  Ball-gags and wrist cuffs and all sorts of accessories, straps and belts and correctional things, are already available for special customers in the locked cabinet, anyway.”
“Oh, that outfit sounds really nice!  Don’t you think so, Eleanor?”
“Absolutely!”
“The shorts come with a pink leather belt, and pink latex frilling at the legs – the combination of red and pink is meant to hint at some sort of sexual ambiguity, you see.”
“How subtle!” simpered Eleanor.
“They’ll wear pink latex gloves, frilled at the wrists, and simple white girly socks, knee or ankle length it doesn’t much matter – either provides further emasculation – and red or pink patent Mary Janes, to go with their shiny caps.”
“They’re going to look stunning!” smiled Diana.  “I can’t wait
”
“And of course, ladies, there’ll be the internal fittings.”
“Internal
?”
“It comes back to that first principle – smartness.  Boys are awkward, unruly – that’s their nature.  So their boy things need discipline just as much as they themselves.  Their shorts will be fitted with the usual internal loops.  That’s to say, one in the crotch and one in the front, welded to the central seam.  The lower one will encircle the base, behind the balls.  It’s function will be twofold: to lift and separate, keeping everything nicely symmetrical, and to maintain erection.  Once erection is established, the upper loop will prevent any untidy deviation, and keep it nicely vertical.  Then we have the butt-plug
”
“The
b-butt-plug
?”
But Cynthia didn’t hear.  She was expatiating on her favourite topic, using her fingers to illustrate the mechanics.  The lecture continued.
“The butt-plug has three functions.  One.  To help maintain erection.  Two.  To correct posture.  Three.  To remind the wearer of his subordinate status.  We have designed a new plug, attached to the back seam of the shorts by a thin flexible rubber stalk, at the end of which is a vibrator about the size and shape of half a sausage, containing a rechargeable cell power source, sheathed in rubber and covered with short, flexible rubber buds.  The vibe has no external controller – it’s auto-initiated by two electrodes connected by the body’s moisture, and simply pulses, keeping the wearer conscious of its presence.  The pulses vary randomly in speed and intensity, to remind him of his lack of control.”
Cynthia took a breath, and looked at her listeners.
“Do you understand?”
“Oh, we understand perfectly, Cynthia!  Thank you so much for explaining everything so clearly!” said Diana, delightedly.  The outfits sound perfect for those two.  You really have thought of everything.
“Well, thank you
  We do our best
  Ah, Miss Poole.  I’ve just been telling your colleagues about the new outfits
”
“So impressive,” remarked Eleanor.
“Isn’t she,” smiled Miss Poole, archly.  “And I believe you already have some new ideas, Cynthia?”
“Oh, yes.  Bobby’s dress
”
“Let’s talk about that later.  Now, the only other people you don’t know are Magda and her friend Zeta.  Come with me and I’ll introduce you.”
And taking her arm, she led Cynthia away, leaving Diana and Eleanor in an ecstasy of anticipation.
17
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on August 04, 2025, 06:10:38 PM »
Chapter 217.

In any big riding centre, where most of the manual work is done by teenage girls, there is a strong ‘work hard – play hard’ ethic.  After a day struggling with recalcitrant horses, mucking out, running back and forth with tack, and servicing the demands of impatient and sometimes downright rude riders – especially the privileged types, many of whom had never done a serious day’s labour in their cossetted lives – nothing short of a wild evening is enough to prepare for the next day.  Serena Egerton had come from quite a deprived background, and had made her mark by a combination of hard work, persistence, and a natural empathy with horses.  With a full-time job on top of her riding and baseball careers she was kept pretty busy.  But she still identified with the social life of the stable lass, and whenever she could she kept the company of the stable staff during and after work hours, joking around in the stables, or clubbing in town.

It was at a local bar one evening when Serena was drinking with four of the stable girls, Jasmine, Ellie, Betony and Imelda, and Phoebe from Fleetford, that the conversation turned to Bobby.  This was before the big show, when the boot parlour was still in process of construction.
“Have you ever heard such a thing?” Imelda was saying.  “Who is this guy?  He’s actually gonna be employed to do nothing but service riding boots?  Must be some sort of pervert or something.  Do we really want a bloke like that living amongst us?”
Jasmine, Ellie and Phoebe looked at each other.  Phoebe knew all about Bobby the Pony, of course, but had been sworn to secrecy.  She would quite happily have outed him, but it was much more fun to hold onto the secret and watch him steadily descending into permanent pony bondage.  She was sure that soon, escape would be impossible.  Then she intended to approach MĂ©lisande and demand, on the basis of her former relationship with him, her share of the riding rights. 
“We know the guy,” she said, blandly.  “Yes, he is a pervert, but a nice one and quite harmless.  Oh, and quite cute, too.  I can assure you that if this boot parlour thing comes to fruition, there’ll be some fun to be had.”
“That’s right,” said Jasmine.  “Miss Poole is set on it, so I’m sure it’s gonna happen.  She knows what she’s doing.  It must have potential to make the Centre some money, or she wouldn’t be investing in it.”
“True, but I’ve always thought old Pooley was a bit of a pervert herself,” grinned Betony.  “There are rumours she once whipped a stable boy for misbehaviour.”
“They’re true,” said Serena.  “I witnessed it.  Maybe she is.  It makes it all the more fascinating.”

A few weeks later things became clearer, and then, with Bobby and Timmy’s appearance at the October show, all doubts were dispelled.  The girls met up again that very evening.  Ellie bought a round of drinks.
“Oh my god, you guys are so lucky, you know that?”
“Why?”
“Guess who’s been appointed official Supervisor of Boot Boys?”
“Official what?” said Imelda, making a face.
“Supervisor of Boot Boys – the person in charge of those two kinky guys!  Me, idiot.  On Friday.  Not only that, but
”
“We saw that Timmy one whipped by Miss Poole,” added Jasmine, unable to contain the intelligence any longer.  “Actually, we helped, didn’t we, Ellie?  We held him down while she gave him twelve strokes of her dressage whip.”
“You
saw that
?”
“Yes!  It’s true what they say!  Anyway, apparently they’re both under contract, with very strict terms, and they can’t get out of it for at least a year!”
There was a brief, disbelieving silence.  Then Ellie began to fill in the details.  Eventually everybody took it on board. 
“So
” said Betony, thoughtfully, “are those two really into boot slavery, or
”
“Bobby definitely,” said Ellie.  “He can’t help himself.  Not only that
”
Jasmine gave her a look.
“Ah, yes
  I was going to say, he’s totally into latex, too.  A real fetishist.  Miss Poole’s working with a company called Fantastex, who are going to make all their outfits.  I can see what she’s up to now.  The main thing isn’t to provide a service for the staff and members – though that will be useful – but to attract visitors who’ll be asked to pay through the nose for the service and be expected to give tips – depending on what sort of “entertainment” they get.  There are so many bored women in this area, desperate for some sort of thrill, and Miss Poole is providing it, by allowing them, for the duration of the session, to become strict mistresses of two cute young guys in sexy outfits, trained to be obedient and submissive, down on their knees like real slave-boys.”
“Yes,” said Jasmine, “and the customers don’t have to be guilty about it – they can rightfully claim it’s a purely cosmetic service, like getting their hair or their nails done.  Meanwhile what actually goes on behind the door of the parlour – well, who can say?”
“And it will be good publicity, and some of those who come for the boot parlour may well decide to join and take up horseriding.  It’s brilliant.”
Serena was fascinated.  “Wow.  Bobby’s the cute blond one, right?  I already want to book a slot.  You know how much I’m into leather and latex, Ellie.  I need to see these two – especially Bobby.  He sounds very interesting.”
“You should book a session and go wearing one of your latex catsuits,” laughed Imelda.  “If it’s true he into that stuff, it'll drive him wild!”
“Hey
yes!” cried Jasmine.  “Why don’t you?  He’s really into boots.  I think that’s what gave Pooley the idea in the first place.  Wear a pair of your sexy thigh-boots too!  I’d love to see his reaction.”
“Do you want me to book you in, Serena?” said Ellie.  “I can ask Miss Poole when I see her Monday.  They’re booked up weeks ahead, but I’m sure she’ll let me fit you in.”
“Oh, god, yes – can you?  I’m feeling sexy just thinking about it.  I’ve got these great new red leather thigh boots I haven’t dared to wear yet.  A boot fetishist’s dream!  If it’s true, then
”
“Leave it with me, darling
”  Then suddenly her eyes danced.  “Oh, and Serena -  I’ll tell you what else I can do.  It’s rather naughty, but
”


The girls were in early Thursday morning.  Serena had two horses in livery at Pitt’s Wood, and she got dressed up in her finery at the back of one of the stables, then posed outside for a photoshoot, before being smuggled into the boot parlour waiting room.  Ellie, without telling anyone, had decided to spice things up with a squirt of two of pink lube in the front of the boys’ trunks.  She wasn’t sure how long it would take for their bodies to react, but she didn’t want it happening prematurely, so she held them back as long as she could.
“Come on Ellie,” said Timothy, from outside the washroom.  “It’s ‘alf eight.  We need to get changed.  Serena could be ‘ere any minute.”
“What’s the hurry?  This is the first time you’ve been so eager to start.  There’s half an hour yet.”
“Yeah – but today’s different.  I need to have as long as possible with this woman.  I’ve got a lot of stuff to say to ‘er.”
“Oh, really?  What, you planning to send her to sleep or something?  Don’t make me laugh.  I’ll bring them in as soon as they’re ready.”
She held them off till a quarter to eight.  Then handed their outfits in at the door.
“Okay.  Actually you’d better hurry.  It seems she’s here already.”
“What?  I told you so, didn’t I?  Bobby, quick!  She’s ’ere!”

They were dressed in five minutes flat, in the corridor pulling on their gloves and hats.
“Ready?  Okay.”  She opened the waiting-room door, and with a smirk, ushered them in.
18
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on August 04, 2025, 06:40:12 AM »
Chapter 216.

Over the next couple of days it was more of the same – half-hour sessions, two girls a session, nearly all stable lasses, varying ages, plus a couple of others, including Gabby from reception, desperate to see Timothy in the flesh.  Anyone of seventeen or so or older got the benefit of Timothy’s cheesy chat-up lines, which were always received with good humour – it was impossible to take offence at such a display of innocence from a guy showing off in a two-piece latex superhero costume which he clearly believed made him irresistible to women.  Their reactions he interpreted as success, though, as he told Bobby, he was holding back for his main goal, Serena Egerton – whom he referred to familiarly as “Serena”, as if they were old friends - or even already lovers.

The boys stayed in their apartment all that week.  Indeed, they found they were too tired at the end of the day to do anything else.  In any case, it was thrilling to have their own place, where they could relax, drink, play computer games or just watch television.  Timothy kept his bedroom tidy and fresh, ready for his first conquest.  Bobby was often so tired that first week that a couple of times he crashed out on his bed straight after supper, and woke early in the morning still in his uniform, with the result that Ellie had to rush to get it washed, dried and ready before nine.  But on Wednesday night Ellie brought him a message from Miss Poole, to the effect that he was to come to the committee room at eight that evening, to allow Cynthia to check the fitting of his new superhero costume. 
When he arrived, he found not only Cynthia and Miss Poole, but a small audience of Nicole, Lavinia, Clarissa, Diana Murchison and Eleanor Bowditch, Magda and Zeta.  Cynthia took him into a side room and got him into his uniform, which was a purple two-piece much like Timothy’s, with pink boots.  It fitted perfectly, and felt light and comfortable.  He looked at himself in the mirror,
“You’ll have a pink cap and pink gloves, but I just wanted to see I had got the measurements correct,” said Cynthia.  “It looks great on you, doesn’t it?”
“Yes.  It feels good, too.  Tim will probably accuse me of stealing his thunder, though.  He thinks he looks so great in his.”
“Let’s go and show the others.  I’ll put your cape on for the time being, but of course you’ll work without it.”
She led him back in, to an admiring murmur of approval from the ladies.  He stood before them and turned through a full circle like a fashion model.  He faced his audience so they could take a few snaps.
“Excellent, Bobby,” said Miss Poole.  Wear this for the rest of the week, then next week I think Cynthia has new outfits for both of you, is that right?”
“Yes, Miss Poole.  Identical pageboys next week, based on the outfit Bobby will wear to the wedding next month.”
“Yes.  But these two-piece creations will remain in your wardrobe, of course.  I like them for their simplicity, and the way they show off your bodies.  You’re both commendably fit.”
“We both work out, Miss Poole,” said Bobby.  “Though we haven’t done much this week.  It’s been so busy.”
“Yes, I understand of course.  But things will get easier as the days go by.  Just make sure you keep up your exercise routine.  I’m adding some new pieces of equipment to the gym, but please tell me if there’s anything else that you’d find useful.”
Zeta grabbed her camera, hopped off her chair, and knelt behind him.
“Bobby?  Turn and face me.  I need to take one good piccy in case we need it for promotional stuff.”
“Okay.”  He turned his back on the committee members, and she took one photo.  She checked it.  “That’s good.  I’ll distribute this by email to everyone.”
“Thank you Zeta.  Thank you Bobby.  Please go and change, and I’ll send your uniform to Ellie so she can get it ready for tomorrow.  You’ll have Serena first thing, then
” - she consulted her diary – “then it’s Natasha and Bethany?  Is that right, Nicole?”
“Correct, Violet.”
Bobby’s face fell.  “Natasha and
”
“Yes, Bobby.” said Nicole.   â€œThey know all about you now, of course, so naturally they deserve a session.”
“Oh
”
“Off you go, then.”

Bobby was not so happy when he returned to his rooms.
“What’s up?” asked Timothy, concerned.  “What happened?”
“Oh, nothing really.  Got my new outfit.  Like yours, but purple.  But tomorrow, after Serena Egerton, we’ve got a special.  Two of Mellie’s friends’ mothers.”
“Is that
bad?”
“Oh, not for you.  But
you know.  How do you think I feel?  The mothers of two of her bratty little friends
  And I have to kneel down and polish their boots and call them madam and stuff?  How would you feel?  Suppose they take photos – no, they will definitely take photos – and then go showing them to all their friends, and then they’ll want to book sessions too
”
“Oh, poor little Bobby!” laughed Timothy.  “Serves you right.  You shouldn’t ‘ave got so pally wiv that MĂ©lisande girl.  I mean, why are you ‘er friend in the first place?  ‘As she got some sort of ‘old over you or what?  I never got that
”
“Oh, shut up, Tim.  I’m tired.  I’m going to bed to read.  Good night.”
19
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on August 04, 2025, 06:33:09 AM »
Chapter 215.

Trixie and Grace were no different from any other teenage girls.  If there was the faintest chance they might come into contact with - or even flit through the field of vision of - any eligible boy,  their first thought was that they had to be, first, immaculately turned out, and second, if any interest was shown in them, cool, aloof and detached.  In this case, however, the second requirement didn’t really apply; these particular boys were not “eligible” in any way; not prospective admirers, but amusing curiosities capable of yielding infinite degrees of gossip and entertainment.  So whilst they had taken pains over their makeup and put on their best breeches and boots, it was not, as Timothy imagined, out of regard for he and Bobby, but as a subterfuge to flatter them, with the aim of gathering information and spicy chatter to pass onto their friends!
Bobby, thoroughly familiar with the riding scene, and with the culture of Pitt’s Wood, knew this perfectly well; but he was quite happy for his friend to make a fool of himself – which he did right from the beginning.
Trixie began by dispelling any self-consciousness Timothy may have had.
“Timmy!” she gasped, turning her big innocent eyes on him, “you’re so tall!  I didn’t realise when I saw you in the arena.  D’you know me an’ Grace were next in the queue Saturday?  We were so disappointed we just missed you.  But this makes up for everything!”
“Oh
er, yeah
  Sorry about that.  Got called away
Miss Poole, you know
  ‘ad to attend to some business for ‘er
”
“Gosh, I understand completely.  It must be so great to work for her directly.  We’re all a teensy bit scared of her, you know.  She’s so strict!”
She didn’t have to tell Timothy that.  He knew only too well.
“Strict but fair,” countered Timothy, as if he and she went way back. 
But Trixie was already admiring his uniform.
“Your uniform is amazing!  ‘Specially now I can see it close up.  Did you choose it yourself?”
Timothy was beginning to relax.  “Nah.  We ‘ave our own dresser.  Big clothes company.  What’s it called, Bobby?”
“Fantastex”
“Fantastex, yeah.  They’re gonna make all our outfits.  This is just the first one.  Next week we’ll ‘ave somefink new.”
“It’s so
gorgeous
” said Trixie thoughtfully, reaching out familiarly and running her fingers down the side of his yellow pants.  “Latex is like, mega expensive, isn’t it?”
“Mega.  If you wanted to buy this stuff, it’d be, like, hundreds of pounds
”
“Really?  Gosh
”
Grace decided it was time to get in on the act.  She could see by the expression on Bobby’s face he wasn’t taken in.  So she added her flattery to her friend’s.
“That’s right.  Latex is like, haute couture, innit?  Bobby’s outfit is cool, but it’s not pure latex, like yours.  My mum knows about this stuff.  She’s booked a session but she has to wait for weeks.  She’s so jealous I’m getting to see you guys straight away.”
“Oh
I’m sorry
”
“S’not your fault, Timmy.  But maybe we could have some piccies to show her?”
“Oh
sure.  Of course.”

The girls seemed to know exactly what they wanted, as if they had planned it all out in advance.  They took him out into the waiting room.  First they had him full length, then posing with his foot on a chair, making a peace sign; then looking macho, with his thumbs tucked into his belt; then hands on hips, and after that lying along the row of chairs, head propped on his hand.  Then Grace handed her phone to Bobby, and he took photos each of them with their arms around him; then one on each side, holding him tight, his hands on their backs.  Then they slid down, kneeling either side and embracing his legs, their heads resting against his flanks.  And finally, Grace fetched a cloth from the parlour, and Bobby took videos of Timothy kneeling and polishing their boots while they sat side by side in the waiting room chairs!

“Er, I think we should get on,” said Bobby, checking his watch.  “Not that your boots look like they need much work
”
Indeed, the session was fairly perfunctory – a little waxing and polishing, and they were done.  But it was fairly obvious to Bobby they hadn’t been there for boot-cleaning at all.  As they scurried off, giggling and whooping, Timothy agreed.  But his take on it wasn’t quite the same as his friend’s.
“I told you we would be celebrities, didn’t I?   Mind you, it was mainly me they came to see, right?  Sorry, Bobby, I didn’t mean to steal your funder.”
“No offence taken, Tim.”
“I reckon they’re all gonna be like that.  Next week we’re getting some of the older girl grooms, right?  I’ll show you how you ‘ow you chat ‘em up, okay?”
Bobby sighed.  “Sure, you go ahead, Tim.  I’m just here to do the job and earn a bit of dosh.”
“Yeah, well, you never were into girls that much, was you?  Fine.  You can leave ‘em to me.”

The rest of the day wasn’t much different.  Lot’s of excitement and giggling from the customers, lots of swaggering from Timothy.  But at least there was some real work to do, and the girls all left with shinier boots than those in which they had arrived.  There were two older girls - members, Bobby thought - expensive boots and leather breeches - who couldn't stop laughing.  One of them had very muddy boots, despite the fact it was a dry day.  She must have gone out of her way to find a muddy puddle.  But he wasn't fazed.  He cleaned them up and polished them till they shone.  She was definitely impressed, and even gave him a decent tip.  Yeah, he was pretty cool...
The boys got through dozens of strips of thin card.  To avoid getting polish on the girls’ breeches, these strips were folded around the legs and slid down into the tops of the boots.  Simple but effective.  It had been their first day.  It had gone well.  They were tired and slightly dishevelled, but proud of what they had achieved.  After the last customers had departed, they had a visit from Miss Poole.
“Well done, boys!  I’ve interviewed most of the girls you’ve serviced today, and I can report they all gave you five stars.  That’s terrific!  I’m sorry you won’t have received any tips as yet, but they will come.  You will probably have seen you have two specials this week, Thursday and Friday mornings, as well as staff.  Oh, and there’s a revision to Thursday which isn’t in your schedule – first session, nine o’clock to ten, substitute Miss Serena Egerton.  Do you know her?”
Bobby had heard the name somewhere, but couldn’t place the individual.
“Who is she, exactly?”
“She’s a member.  Local.  Rides here regularly.  County level dressage and showjumping.  Plays baseball too in the southern league.  Very fit.  You can wipe that smile off your face, Timmy.  She’s only interested in two things, horses and baseball.   Not boys.  Always immaculately turned out.  Wears some eye-catching outfits in both disciplines.  Never know what she’ll turn up in.  Tall, willowy.  Long blonde hair.  Twenty-ish.  You may have seen her about.”
“Don’t think so
”
“Anyway, she’s very nice.  Give her the celebrity treatment, all right?”
“Of course.”
“And Cynthia will give you your other uniform, Bobby.  It’s like Timmy’s, so you’ll look more of a team.  Okay?”
“Yes, Miss Poole.  Thank you.  Er...  Miss Egerton...  Will she be by herself, then?”
“Yes, all on her ownsome.  But I'm sure you'll find her enough of a challenge...”  She smiled knowingly.  “Okay, then, must rush.  And well done again, boys!” 
She swept out.  Timothy’s face lit up.
“She sounds cool!  Long blonde hair?  Twenty-ish?  Sounds just my type.”
“Forget it.  You heard what she said, Tim.  She’s only into sports, not guys.”
“Okay, Bobby.  We’ll see, won’t we?  You wait.  Watch and learn.   I’ll show you ‘ow it’s done
”

20
Active Sissy Stories
/ Re: The Second Floor (#38)
« Last post by petticoated on August 02, 2025, 02:21:15 AM »
Leighton was STUNNED by this sudden turn of events. And when he heard Emily refer to him as Her "soon to be boyfriend..." OMG! "Oh, Em!" Dorian exclaimed, laughing, "he's not nearly ~Effeminate~ enough!" "Yet," Emily quickly responded. The two of Them were laughing together at the fear that was now clearly obvious on leighton's Pretty little sissy face, his painted Red lips a sign of things to come. "Allen," Dorian condescendingly addressed him(?) by the masculine pronoun. "Should you accept My generous offer of employment this evening, I will be wearing my light blue Boucle Miniskirted Skirt Suit for an important upper management meeting tomorrow. Additionally, you will choose a matching light blue lacy bra, panty, and garter set and white stockings for Me to wear before you retire for the evening...after the four of us have some fun. Find the ~Laciest~ set I have. Understand...sissy?" Allen(soon-to-be full time Allison) attempted yet another imperfect curtsy, responding in a higher than normal (for a male, anyway) pitch Feminine (Feminized) voice, "Yes, Mistress." "Good gurl," adding, "Only one of us is permitted to wear blue, sissyboi. Just like only one of Us in Our ~Blossoming~ New Relationship wears the ~Pants.~ By the way, Allison, should you accept My ~unconditional~ offer of employment this evening, you will begin sleeping in the Maids Quarters this evening. In your Lingerie chest, choose your ~Laciest~ Bra, Panty, and Garter Belt. In Pale Pink. Your ~Bras~ are all padded...for now." Seeing the look of shame on Allison's face at the mention of wearing a ~Bra,~ Dorian laughed. "Don't worry your pretty little head about having to wear padded ~Bras.~ That's only temporary. Because every morning, starting tomorrow morning, I will Personally place a super strong hormone patch to your cute little bottom," Dorian laughed. " Now, Allison, let's get you into your very own brand new ~Cinderella~ Petticoat so We can work on your ~Curtsy.~"...
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