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**Thank you everyone for reading and taking time to vote on Ch. 01. Do please feedback. I hope you like the evolution in Ch. 02. It has taken a lot longer to get going than planned!**
*****
Simon stared at his phone in his office, not quite comprehending. Sally or Aunty as she’d told him to call her had sent him a text.
“Simmy dear, don’t forget your appointment tomorrow after work, I’ve laid out some clothes for you. I’ll arrange make up and a wig too but do please get your hair trimmed really short and shave your legs… and everything in between *giggle* so we can be a bit more adventurous! *kisses & cuddles* Aunty.” Attached was a picture of a very pretty if androgynous girl or maybe boi in a skimpy, slutty, school girl outfit that would clearly reveal all if she bent over just a bit more.
Simon stared feeling an unholy mix of desire and unease. He’d tried not to think about last week after work and the stockings and spanking nor that she’d offered another tryst and, frankly, abjectly failed. That photo was one he’d actually seen online well before. Stared at, obsessed over, copying the coy pose that hinted but did not reveal, imagining himself as her, put the outfit in the shopping cart of the online store so fucking often before chickening out. He’d had all sorts of fantasies even putting whole outfits and accessories together to go with it, a pink jewelled butt plug, spankers, dildos and even a unique white leather strap cock cage. God he’d jacked off to it so often. It was like she’d read his mind…
Simon realised he could pop into the barbers and say he was attending a conference overnight to his wife but what about shaving…well everything…the hint was quite clear. Simon shivered, not sure if he wanted to go that far, having to start avoiding his wife so much. A big move from just ‘working late’. Simon’s hand actually shook… he wanted that outfit. He couldn’t deny he’d been turned on by the session and the little light play spanking and teasing hand job… but he was married!
Simon texted back, somewhat half-heartedly “I’m really sorry Aunty but I’m not sure I’ll be able to make that after all.”
The return text came back pretty fast, “Oh you aren’t going to stand me up are you, Simmy? *pouts* I’ve the uniform, a wig, toys I *know* you’ll love and make up duty on stand-by … and missing that would make you a very naughty school girl indeed! I know you want it, Simmy. Wouldn’t want to tell tales out of school now would we? What would little Miss Prim think? After all, you know playtime will be such fun *winks & giggles*.” This time the attachment was another photo of him from her place last week, wiggling his bottom in stockings, face clearly smiling back over his shoulder at the camera.
Simon’s heart sped up, he.. had that photo on his phone, nowhere else! He’d changed his pin and everything. Okay calm down, she’s just playing, teasing, it’s just a joke but… toys? Simon groaned to himself as he realised he was giving in already. The jokey but nonetheless obvious threat combined with an almost creepily accurate promise of his secret fantasies coming to life made it inevitable.
“Sorry Aunty, I’ll come of course. Didn’t realise you’d made such an effort. Simon.” he texted, reluctant but undeniably excited.
“Don’t be silly, it’s fine, just be there at 6pm for detention, and it’s Sissy Simmy!” came the reply.
Simon felt his cheeks burn as he almost buried his face in his papers on his desk and tried vainly to follow the investment numbers that swan in front of his eyes.
That night he went to the barbers for a ‘summer’ hair cut, close cropped of course. That night his wife just kept talking, almost like she was determined to keep him from the desktop he was so desperate to check up on to see if he could make sense of his creeping suspicions about Aunty and her ability to get into his fantasies.
The next morning, trembling, tried to shave his legs and more intimate areas, surprised at the fumbling awkwardness of it, even with an electric mesh razor, having made noises about being cold and putting on pyjamas the night before as a sort of cover in case he needed it. For some reason this had made his wife giggle. She had patted his cheek “Well get comfy dear, I’ll miss you tomorrow night” as he’d told her he was away at a conference.
The working day was sheer hell. Itchy stubble in his underpants, catching on his suit, battling with the images of the school girl in his mind, wondering what games Aunty had in mind. Focusing on spreadsheets had never normally been a problem but, suddenly, making his bonus was not high on his priorities for once.
At 6pm he knocked on Aunty’s flat, positively trembling, small over night bag in his hand. The door opened and there was Sally, Aunty, in a button up white blouse and black skirt, black pumps and … of course… stockings and suspenders looking every bit the school ma’am of some of his fantasies. He swallowed with an audible gulp when he saw the old fashioned willow cane in her hand.
Aunty grinned with a so sexy mischievous güvenilir bahis twinkle in her eyes, “Don’t worry Simmy, it’s just for show… if you’re a good girl anyway! Now come in, we need to get you ready. Put your bag down.”
She ushered him into the lounge which he was startled to see was set up with a pretty professional looking photo shoot set up and tinkering with the camera was a voluptuous lady. Simon was pretty sure his eyes were bugged out not even processing the fact he suddenly had a third party in the room. She had a plump bottom, a mature thick middle and huge buxom cleavage all amply on display by the black shiny panties and matching shiny black buckle corset with linked suspenders and stockings completed with lace, arm length gloves. She had long curly black hair and deep red lipstick.
In a funny way the obviously fetish look and her overt sexiness put him at ease even as he realised that this was way more than a play session with Aunty.
Aunty grinned as she saw him goggle at her colleague. “Stop drooling Simmy! Nice girls curtsy and say hello politely but we will practice that later. For this evening you’d better call me Aunty S and Maggy here will be Aunty M. Aunties S and M! Aunty M is on make-up and camera duty and will assist me with… any required disciplinary issues.”
“Now we want some pictures of you for before and after show and tell, so go stand in the hot spot and see if you can look masculine for a minute or two!”
Simon, hustled, off balance, complied, obeying the rapid fire instructions from Aunty M on facing front, side and quarter profiles. She had a low husky voice that matched her outfit, every move behind the camera had her hips swaying. She positively oozed sex appeal. A complement and contrast to Aunty S’s comforting approach.
He knew he should go, protest or not let them take photos but he was just in his suit right? It didn’t help his lack of resilience to be the subject of close inspection by the bubbly, active, mature sex goddess in glossy black as Aunty S stood in the background in her school mistress outfit, tapping her cane with a wink every time he looked her way. Without fail, this meant a grinning scold from Aunty M. “Stop blushing Sissy Simmy! At least try and be manly!” she teased, leaving him a squirming mess and quite relieved when the studio lights were turned off.
“Now Sissy Simmy follow me.” Aunty M walked towards the bedroom, luscious bottom swaying, drawing him on more effectively than any leash.
Just before the door she turned, making him almost stumble into her buxom display.
“Now Sissy, behind this door we will begin your transformation so strip down now and let me see the raw material!”
Simon fumbled as he nervously obeyed, the smooth change the Aunties had done from supportive and comforting last week to effortlessly in charge not lost on him but leaving him meekly obeying.
“Pick up your clothes silly sissy and we’ll fold them for you.”
Simon meekly passed them over, not quite realising the implications. Aunty M passed them to Aunty S and, not incidentally, Aunty M open the bedroom with a flourish as his clothes were whisked away.
In front of him laid out on the far side of the big double bed was the very school girl outfit of his masturbatory fantasy. Still an image that made his heart leap into his throat but what burnt an image into his fore brain was, first, the butt plug alongside it. Pink jewelled of course but not exactly exceptional for pictures of sissies he knew but … there next to that was a white leather cock strap chastity cage. Three straps round the shaft, connecting straps that buckled and locked under the balls. In white. Unique, he’d only ever seen one on… Aunty’s Toys adult web store…
Over the blood hammering in his ears he heard Aunty M order him, “Go in and bend over, put your hands wide on the bed and spread your legs, Simmy.”
Aunty S tapped his bare bum with the cane, prodding him forward like a bemused puppet as he obeyed. Aunty S spoke as Aunty M ran her hands over his legs.
“Time to listen Simmy, very carefully. Yes we know all about what you look at online. We’re some of the Aunties of Aunty’s Toys and we know about your fantasies because, well, we supply others just like you. You need a little help though , just a little push because you bought stockings and then got all guilty and sent them back by our customer friendly service. By then, of course. we knew your address and name on your credit card and then everything pretty much follows.”
She giggled, “Uniquely among online intimate clothing suppliers we have a way of making our returns policy very… interest bearing… it comes with free cookies I’m told! Consider us the SWAT team of customer support! Your fantasy will come true Sissy Simmy Sinderella!”
Aunty M chirped, “Not to mention the return on interest for our investors.” If he’d been watching he might have seen Aunty S frown at her. Simon’s inner finance nerd mumbled “return on investment nuur-” eyes bugging out as Aunty M’s searching türkçe bahis hand closed on his balls causing the sudden loss of his words and, indeed, most of his higher brain function.
“One. You are listening Sissy Simmy not talking. Two. I know what I mean. Three. These peanuts, not to mention everything else, are still far too hairy! Aunt S, dear, would you keep Sissy here informed whilst I get my box out.”
“Indeed. So Sissy, your fantasies will come true, just as a few other peoples will too in the process to make it all fair and profitable. No one will be harmed, hurt, no one will object, you keep you real life, job, privacy and Miss Prim apart from a few evenings and the odd Sunday afternoon tea party. Aunty’s Toys guaranteed!”
Aunty M began unpacking a box from under the bed in front of him, setting up around the room. Make up, lipsticks, beauty tools, some form of pot device she plugged into the wall, a range of wigs and, with a giggle, in front of his eyes she placed nipple clamps, various forms of vibrators, spanking paddles and finally a harness and series of fitting dildos ordered in size and colour going from pale pink and small to dark near black and huge.
She ran her finger over them , starting with the small four incher “Good Sissy,” then the six incher “Naughty Sissy,” then the eight inch, “Disobedient Sissy” and then, pausing and saying very clearly, tapping the dark ten inch veined dildo “I call this one the ‘Squealer’ so you will keep our secrets, right Sissy?”
Aunty S tapped his balls lightly with the cane “You may answer and choose Simmy dear.”
“G.. yes.. good Sissy I’ll be good, not tell, oh god,” as his body shook, struggling to breath, mind reeling even as the light touch seemed to electrify him.
Aunty S and M smiled at him, suddenly soft smiles as they both hugged him, warm and soft.
“There, see, Sissy Simmy, no need to fear. Aunty M here is going to work on making you pretty whilst I get a few things ready in the other room.”
Aunty M gave him a hug, tension and fear turning into heady sexuality once more as she kissed his cheek, nibbled his ear, curves against him, running her finger between his bottom cheeks “Now, no moving, Sissy. We’ll pretty up that display! Later we will give you some gadgets and creams to make this easy but those take time.” She poured what looked like little white balls into the melting pot “But waxing is fast and will … set the mood … ” she giggled again, tapping the cock cage “not to mention making fitting easier.”
Aunty M it turned out was experienced, professional and quick when it came to waxing, using a pre-cooling gel of some sort. It was intimate, humiliating with flashes of lancing pain as the hot strips came off. After the first scream, Simon accepted the offer of a bit to bite on, embarrassed as she teased him. “It’s OK sissy, no need to be manly any more tonight.”
She kept talking , stroking, encouraging.
“Ready Simmy?”
“Good girl.”
“So much prettier.”
“Brave girl.”
Each strip of wax eroding Simon for the evening, becoming Simmy.
Soon Simmy’s legs were done leaving the root of Simmy’s shaft, balls and bottom. She had Simmy turn and lay on her back for her shaft and balls, making it quick even as Simmy clenched his teeth, eyes watering. A gentle, intimate application of soothing gel and she slipped over the cock cage and fastened it under her now hairless balls with just the buckle, no lock.
“Back in position now, sweety.”
It felt … excitingly obscene as the wax oozed into her bottom before being covered with cloth strips. Then a brief flash as her world once again turned into pain momentarily.
“Such a sweet bottom now!” That was followed by an intimate, verging on the obscence, kiss that made Simmy blush and squeal for very different reasons! Aunty M kept up kissing her now smooth skin, especially her bottom and hairless balls as Aunty M slathered on cream, cooling slightly numbing the after shock. The close erotic caress and whispered nothings and murmuring allowing Simmy to recover quickly and start feel the restrictions of the tightening supple leather around her stiffening little cock.
“Quiet now, pretty one.”
Still bent over the bed Simmy whimpered as Aunty M picked up a tub of lubricant and the butt plug. Using her fingers to spread the lube around Simmy’s bottom she slowly … god so slowly … pushed the small cold metal jewelled plug into Simmy’s tight virgin bottom. Simmy first whimpered as she felt her so exposed hairless bottom stretched open and then gasp as the tight ring of muscle gripped the shaft of the small but heavy plug.
Aunty planted a smacker of a kiss on Simmy’s bum, leaving a clear red lipstick mark.
“Mmm that does look like a pretty girl’s bottom now!” Aunty M giggled. “If slutty! Now sweet sissy Simmy, I think you should have a moment alone to get into your uniform. Knock on the door when you want me to do your make up.
Aunty M joined Aunty S in a side room. Simmy would have been rather startled at the banked güvenilir bahis siteleri monitors and the exchange between the two as they started filling in forms and comments.
“Careful Maggy, go off script too much and you might end up entertainment at Aunty T’s party too.”
Maggy grinned, “I’ve been worse Sally! Aunty S&M indeed! Who’d have thought the nerds were right, the shy ones that don’t buy much and get embarrassed are the easiest to recruit.”
Sally chuckled, “I thought it was common knowledge to look out for the quiet ones! Who needs algorithms! Still I guess what Simmy does next is the next checkpoint on the list.”
Sally looked at one of the feedback requests on the monitor, “and which one of our smart alec nerds came up with adding liquid viagra AND rohypnol to the anal lube?”
They both turned to the monitors showing Simmy curled up in a ball on the bed, slowly stretching out a hand to stroke the white girly stockings lying on the bed.
Simmy sat for a while shaking slightly. He… she wasn’t locked or cuffed or particularly ill treated but she did have a restraining unlocked cock strap and metal butt plug slowly warming up in her bottom. Along with the thorough hair removal she felt…transformed. Rattled, suggestible and… well the worse had happened really hadn’t it? Whatever happened she’d somehow explain it to her wife and the Aunties had promised…
Simmy shivered as she started to roll the smooth silky stocking up her smooth hairless leg, not even stubble to detract from the sybaritic pleasure of sheer silk on skin, sissy little cock , recovered, pushing against the binding white straps.
“Gotcha!” murmured Sally watching in the other room, adding some information to one of the screens in front her. “Lets get ready”.
Soon Simmy had on both stockings, a padded bra adding small breasts to her slim figure, a little skimpy white button up blouse showing her midriff and a slutty short tartan skirt barely hiding her strap cage and butt plug and showing the wide white garters linking her stockings to the sexy garter belt underneath.
Aunty M knocked, “Ready dear, can I come in?”
“Yes Aunty.”
Maggie smiled delightedly, “My don’t you look good enough to eat already? Lets see what I can do to help you, pretty Simmy, get ready for school. Such a good girl. One thing Simmy though, at school it’s Miss S and Miss M right? Can’t be too informal with the students!”
She winked and playfully nudged Simmy who couldn’t help but giggle “yes, Miss M!”
Maggie had Simmy sit still as she put on a blond bob wig and started on face and eye make up, not too much nor too heavy and clearly treating this as a lesson. Last she added a liquid lipstick “I like this one, not for photos so much but it goes on thick and lets you leave kiss marks on everything.” This was followed by an unashamedly lewd wink as she picked up the strap on harness and the smallest dildo and placed it by her.
“Especially Good Sissy!” Simmy squirmed, face blushing at the blatant implication.
“Now shoes dear.” Maggie reached under the bed and brought out strappy white shoes with a modest two inch kitten heel. They fastened with a click. Simmy’s eyes went wide as she realised they had a locking latch rather than a buckle. Maggie giggled at Simmy’s look and leaned into to kiss her red lips softly, making Simmy melt and her sissy cock pulse in the tight straps. “No worries now pretty Sissy Simmy, just a little something to keep them on you. Now practice walking a little before we go out.”
Simmy tottered round the room, grateful the shoes were no higher. Even then she felt quite peculiar as it felt like her little bottom was thrust out as she walked, unused to the even smallest lady’s heel.
Maggie clapped, “Mmm sexy sissy Simmy! My new naughty school girl will get the detention she deserves! There’s a mirror in the hall sweet heart.” She gestured , letting Simmy step out back into the rest of the flat under her own power, following the artful script , letting Simmy feel the illusion of making choice after choice.
Simmy gasped at the willowy but decidedly slutty school girl in the mirror. Far from perfect but such a transformation for the first time. Aunty… Miss M was clearly a wizard with the make up and Simmy wondered if she’d remember all the tricks. She moved, turning her hips posing in the mirror, her motion suddenly making herself so aware of the butt plug in turn making her cock throb against the straps. Simmy let out a gasp and blushed, even as she saw Miss M wink at her. “Yes dear, we will play so nicely with our new sissy toy.” Miss M pointed to the lounge.
Simmy tottered in to find the photo shoot set up had been turned back on but this time instead of a clear area there was a teachers desk with draws and a chaise longue to one side.
In front stood a sexy Miss S, bending her cane and pretty much failing to frown as her smile broke through. “Oh you are a pretty Sissy! So pretty and sexy and so brave. I’m so happy you want to play with us dearest!” She hugged Simmy to her, kissing her deeply, possessively, leaving Simmy reeling. Sally made a show of pulling her self together after laying on the praise so thickly as she turned to the ensure the camera caught them both as Maggie took over camera duties.
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