All PG 13 The Stepford Sissy
A young man is sent to live with his aunt in the picturesque town of Stepford, though its more than he was expecting.
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To call the building he was currently waiting in an airport would be incredibly generous. On the same level of generosity that a wealthy billionaire would give a billion dollars to a local small time charity with the aims of helping them get set up and help as many people out. A building that covered half an acre of land, a few sheds that stored small aircraft and fuel tankers when they were needed. A single runway stretched for half a mile out into a field and even then there was only one plane, and a small line of no more than thirty people waiting to board the short haul flight out to a more populated area of Ireland.

They were on their way out of the area, though Ryan was currently standing in front of the lost baggage claims desk becoming more irritated by the second at the blonde ladys lack of common sense to get off her rounded backside and go and try and find out any more information as to the whereabouts of his missing luggage that didnt turn up on the reclaim belt in the arrivals lounge of the wooden building of the airport. Two bags full of clothing and the very few personal possessions that he had brought over from England. The sixteen year old turned away from the desk before rubbing the bridge of his nose with his thumb and index finger. He was tired from the journey he had to take. First a train from Southampton to London Gatwick, and then from Gatwick to a remote airport six miles outside of a small town called Stepford, located in a rural area of Ireland.


There were a few sounds coming from behind Ryan, the lady at the desk had started to type in a number to her phone, she had started to ask about Ryans luggage. Finally. It had taken them long enough to do It, and hopefully he would gain some answers as to what was happening. Where had his luggage gone off to? He had it with him on the train, through the underground system and he checked it in with the right labels at Gatwick. The idiots at luggage handling had probably misplaced his bags and had it sent on the wrong flight. For all Ryan knew it was probably in China or Afghanistan. Somewhere stupid.


Im going to get a drink. He told the woman at the desk, having enough of standing around and waiting for an answer that wasnt going to come anytime soon. At sixteen Ryan was different from most boys his age. He was scrawny, and slightly effeminate with shoulder length snow white hair, crystal blue eyes and soft facial features. A scar ran across his right cheek after he got into a fight with someone from school three years earlier. He wore somewhat baggy clothing, though that wasnt by choice. The jeans he wore were a size too big for him, and his t shirt was loose as well as the sleeveless hoody that completed his outfit. He had a black messenger bag slung over his shoulder filled with his passport, a few computer game magazines and documentation regarding the six month visa he had gained to spend with his aunt. That meant two months of summer, and four months at the local school he was going to be enrolled in, though Ryan had no idea what to expect from that.

 

The drinks stand in the only real part of the airport had very little in the way of selection. Budget brand cola, water, lemonade and a few bottles of juice. The stand was part of a shop with an equally small selection snacks, magazines and travel essentials such as blindfolds and ear plugs, not that anyone would need them while on a short haul flight. Ryan picked up a bottle of orange juice with the oranges having supposedly been picked in orange groves located in Florida. He paid for it with a one euro and twenty cents for the bottle, and while walking away from the counter his phone started to vibrate in his pocket. He must have forgotten to take it off silent after he entered the airport. With the slightly warm bottle of orange juice, Ryan walked back towards the lost luggage desk before looking at the caller ID. It was his Aunt Helena.

 

Hey Aunt¦ Im a bit annoyed, the airline lost my luggage¦. Both suitcases. Im waiting for them to respond¦ Im at the front entrance if you want to come in. I wish I knew how long it would take¦ all right see you in a bit. Ryan put his phone back in his pocket, the old model barely had any juice left, and he was hoping to get a new one when he returned, that was if things did improve.


Ryan had been sent to stay with his aunt because financially things at home were going bad. His father was a gambling addict who often squandered what little money the family had either at the casino or down at the race tracks. At one point Ryan would had said that there wasnt a problem, but he was merely living in denial of the truth. His father did have an addiction, and that addiction had cost his family everything. It came to a point in which his parents became bankrupt and had to sell most of their possessions to make ends meet. They couldnt take care of Ryan; that was going to be difficult considering the budget. Thankfully it was the helpful suggestion from his Aunt Helena that had helped the young man out. She had offered to take him in for a few months while his parents worked on getting their finances sorted out.


Excuse me young man, Ive just gotten off the phone with my supervisor! the blonde haired woman called out from the counter of the lost luggage. Ryan had been waiting for that for the past hour and it had better be good news. As soon as he was at the desk the woman started to explain everything.
They had discovered his luggage had been logged on the wrong flight and sent to Australia. It would be a little while before they could get it back though and were deeply sorry. They had an estimated time of at least a week before it could be reclaimed and sent back, pushing its arrival date in Ireland to ten days at the most. Ryan was close to shouting and screaming, throwing a tantrum like a spoilt brat who couldnt get the toy he or she wanted. But he composed himself, resigned to just banging his head on the lost luggage desk. It was a stress relief mechanism he had made up for himself on the build up to his GCSE exams, especially with science. He would sit in class, and when he was being marginalised by his teacher or picked on by the other students Ryan would simply sit at his desk, look on the table and allow his body to drop. The end result would be Ryan hitting the table, and having something less stressful than those around him to focus on.

 

Ryan! a soothing voice could be heard from the entrance of the airport. The few people that were still there looked up and towards the direction of the voice, though quickly turned away. Ryan however didnt. Aunt Helena, his mothers oldest sister and despite living the furthest away, Ryan enjoyed her company and knew Helena more so than those relatives that lived within an hours drive of where he did.


Helena Fairfax was a single woman, unable to have children and with little interest of finding a husband. She had moved from Southampton to Stepford to set up her own business. She owned a clothing store that specialised in outfits from all around the world and in different styles. Mostly for girls, but Ryan had seen online that boys regularly visited the shop so he assumed that there were clothing for males. Helena was a tall and lithe lady of thirty-seven years old. She had long blonde hair that was tied in a ponytail. Her ice blue eyes looked through stylish square rimmed glasses. She wore a pair of jeans, fitted and they emphasised her frame. She also wore a long sleeved t shirt with an Iron Maiden logo on the front. The one thing that Ryan enjoyed was that he could always speak with his aunt about music, movies, computer games and books and the pair of them would have the exact same tastes.

 

Hey Aunt Helena. The two embraced one another in a hug as soon as they were close enough, and with a smile on his face Ryan stepped back, looking to his aunt as she placed both hands on his shoulders, trying to reassure him about the lost luggage situation.


Has there been any developments? Helena asked with a small smile while they walked on towards the desk. There was an envelope placed with a small note, it had his name on it. The blonde woman had picked up an incoming phone call. Ryan explained everything to Helena about the ten day wait for his package. In return she promised him that they would be able to stop by her shop and pick out a new set of clothes for Ryan, what Helena was calling a fashion show.


Then our first stop shall be the shop. It closes in an hour and that means we wont have anyone disturbing us. She promised him with a smile before patting his shoulder and looked to the envelope. Inside was a cheque made out to any bank for a hundred euros. Compensation for the luggage, or at least a small bit of it in Ryans eyes as he slipped it in his bag. Without another word said the pair of them were on their way towards Stepford.

 

-X-

 

The drive wasnt long from the airport into Stepford. In fact it was hardly thirty minutes before signs for Stepford appeared on the sides of the road. Despite being down about his luggage, Ryan was happy to be spending the next six months with his aunt. She was always nice to him, she was kind, gentle, never raised her voice in anger (not that she ever needed to) or treated Ryan like he was little more than an inconvenience. Her door was always open to him so that if he ever wanted to visit her, then he could. All hed have to do was hop on a plane to Ireland and she would pick him up. This had been the first time he had taken her up on that offer. Some had commented on the only reason that Ryan liked his aunt Helena over those that lived in England was because Helena was rich and successful. They were dead wrong about that. Ryan liked Helena because she treated him with respect. Nothing was too much of a problem.

 

Youre quiet. Is something on your mind Ryan? Helena asked from her seat, turning her attention slightly to the left glimpse at Ryan. Excited?

 

A little. He said with honesty before sitting up straight and looking towards Helena. Im also nervous. I dont know anyone other than you here. I¦ well you know what school was like for me. For Ryan, school was a dreadful experience. From his first days in reception all the way towards finishing year 11 he had been bullied and picked on because of how he looked and his size. Yes he looked like a girl, and was small, but it didnt give people the right to treat him like crap.

 

Im pleased to say that Stepford is quite a tolerant place. Gay, straight, lesbian, cross-dresser, lover of all things fetish and all of the above. Everyone is welcome. Said Helena with a smile on her face as they passed the boarders of Stepford.
Ryans gaze was out the window at all times, though he couldnt help but think something looked strange as they crossed over into the town. It might have been his imagination, but something appeared before him but he couldnt fathom what it was. To him it looked like a wall, but an incredibly thin wall no bigger than a quarter of an inch. It was probably less than that, half a quarter of an inch and then it was gone. Maybe Helena was driving too fast. A quick glance at the dashboard put a stop to that train of thought. She was well within the speed limit.

Forgetting the matter of possibly seeing things that arent there, Ryans eyes found they were drifting to what was in front of them. It was the town of Stepford. It looked like a traditional town. Large buildings that looked at home in an American movie set in the suburbs the houses were painted in multiple pastel colours. Every house was different. Large green lawns and parks were in abundance. This was a far cry from the dreary grey city Ryan had come from. His old home had been run down, riddled with crime and full of violence towards one another. It was a form of hell. Stepford was heaven in comparison. This is amazing. Ryan breathed as Helena drove them on. They passed the city hall, the shopping centres.
One thing that surprised Ryan the most was the clothing choices that people wore. Pastel colours, all bright, nothing dark. It was summer clothes for the summer and that wasnt something seen in most towns or cities. It looked as if he and Helena were the only ones out wearing black, though they hadnt passed the small business area of Stepford just yet and so that could change. When they had stopped at the traffic lights Ryan could see a better picture into the park. Girls wear wearing petticoats underneath dresses, and they were fashioned in the style of fifties America. Men were wearing just as bright colours, though a little more masculine and no one was wearing dresses. While he saw adult males, Ryan was finding it difficult to see any males his age. Running through the park were girls. They wore puffy dresses with large bows, knee length white socks, Mary Jane shoes and they all had ribbons in their brightly coloured hair. This was a far cry from Southampton, though Ryans first reaction was somewhat mixed in terms of what he thought.

 

There are no boys. Ryan pointed out to Helena, who merely glanced out of the window before the lights turned green. She didnt comment on that fact, just continued to drive with a content look on her face. Ryan looked towards her, wondering if she was going to say anything. When she remained quiet though, he took it as a sign and nodded his head before looking on towards the shopping district of the town. Mostly clothes shops, but there were also a mixture of entertainment shops, book stores, toy shops and a few shopping malls. Ryan noticed that a lot of the shops were focusing on dresses and formal fashion. That most of the shoppers were dressed very similarly. Young and old. Again, no boys.

 

Aunt Helena, this place is weird. Said Ryan as he sat in the car, looking out of the front window as Helena turned into a parking lot. There was a private space with her surname on, and she instantly took it without hesitation. With a smile on her face and the engine switched off, she looked to Ryan, patting his shoulder.

 

It will take some getting used to. Stepford is a lot more different than what you are used to back in England, but as long as you give it a chance then youll be fine. Helena reassured him, and Ryan in returned smiled and nodded his head before climbing out of the car. It was a shady area, which Ryan found good considering that it was over thirty degrees in the day. Just a warning Ryan; when we enter the shops there may be boys in there, but whatever they are wearing please do not comment. As I said, Stepford is different from anywhere in England. While it was a warning, Helenas tone of voice wasnt threatening. It was simply stating a fact and Ryan nodded again before following her from the car park.

 

Helenas shop wasnt easy to find. There were a few shops along the same row that dealt in specialist outfits. Bridal, sissy, everyday clothes, school uniform shop and a shop that dealt with numerous designs and outfits for males and females aged from twelve to twenty-five. Helena informed Ryan that the shop was indeed hers. It was called Cute and Elegant, a name she came up with when considering how she was going to market the shop. In the windows were dresses and outfits that Ryan recognised from reading manga and watching anime. Lolita clothes. Skirts, dresses, blouses, capelets and bonnets on offer in various bright colours. Looking through the mannequins, looking into the store Ryan could see girls walking around in similar outfits. They must be customers, that or Helenas workforce, though they looked no older than Ryan did.

 

Come on Ryan, lets introduce you to some of the local kids. Said Helena with a smile on her face as she took Ryans hand and lead him into the store. He could see that the girls were doing their own sort of fashion show.

Little did Ryan know that in good time he would be part of it.

 

x-X-x

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TiresiasRex
I'm glad that you have begun this story, Sissy_Fairy! 

I am a big fan of the original Ira Levin novel and the first film adaptation of his work. The Nicole Kidman "dark comedy" remake was...er...atrocious. 

Before you posted this story you asked potential readers which version they preferred: let me be loud and clear early in the game: I prefer the "Dis" robot/android dopplegangers (maybe "replicants" would be a better word, with a tip of the hat to both Ridley Scott and Philip K. Dick) than the brainwashed women (or, in your case, sissies).

In the first film's conclusion, when our heroine meets her black-eyed (soul-less) copy  in "Dis"'s house on that dark and stormy night...chilling. That image stuck with me for years.

I'll be here for your next chapter...and I hope others will be here, too, to enjoy the possibly twisty and horrifying ride! 

Blessings to you, 

Tiresias Rex
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Sissy_Fairy
Hey Tirias, thank you for commenting on my story. 

I've only ever read the novel and seen the remake. I've never watched the movie before so its difficult to really comment on the differences between the three other than you are right; the remake with Nicole Kidman did suck quite badly. Admittedly some of the dark humour was funny, especially Bette Midler's character in the group meetings discussing Christmas.

I'm still debating on whether or not to really go with the robots replacing the sissies or the brainwashed sissies. Part of me says brainwashed as I wouldn't like to live in a town full of robots but that's just me. 

I'm hoping to have the second chapter up by the end of this weekend, sooner if I work while travelling on the train this Friday.
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
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TiresiasRex
...it all depends on whether or not you are trying to recapture the horror element of Levin's novel. If that is the case, then the threat of brainwashing must imply that Ryan (or any other boys) can never return to who they were. They are "gone" after having undergone whatever the "procedure" is. A completely new persona/personality.

If, on the other hand, we want Ryan to become a sissy...and this is (perhaps) a secretly desired state he would like as well...then again, the brainwashing angle may be the better option over the robot replicants.

My two cents worth.
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Sissy_Fairy
You hit the nail on the head with that part. It will be a case of complete brainwashing as once it happens, nothing of the original person remains. It will be a complete change. I never had a thought of Ryan wanting to become a sissy. I've done stories like that in the past and so it will be an unexpected change.
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
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TiresiasRex
Glad to hear my powers as a seer are still in effect (re: the brainwashing). So, I take it you have decided to go for the "horror" angle: and Ryan will RESIST the attempts to change him. Good! I may be the minority voice here (especially given the nature of this site), but, in my humble opinion, there are too many stories of boys quickly "giving in" and submitting to their new sissified roles. There SHOULD be some resistance and youthful rebellion...especially if the "role" is being forced upon them. And therein lies the struggle and the elements of a good story - there needs to be some  tension, some suspense, some struggles (either physically or emotionally/psychically). How long can the character "fight back"? How long can they avoid the "surgery" or nefarious "procedure" before they are transformed into a new persona that they either fear or reject?

I look forward to the new chapters, SF! And thanks for responding to my note!

Walk in Beauty,

T.Rex
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funfayre
One slight problem I forsee with the idea of permanently brainwashing the protagonist is that it would be in Aunt's best interests to get it done asap; then once he's been brainwashed, although you can cover life in Stepford, there's virtually no plot or conflict left (unless the brainwashing is a long-winded process that takes several weeks or months).

Perhaps a more interesting take would be for his Aunt to have genuine interest / affection in him, so alternating periods of temporary brainwashing and lucidity - her aim being to encourage him to lead him into learning the behaviour / mannerisms of a typical Stepford child in public but retaining the ability to speak freely with her in private - all the time with the omnipresent threat of permanent brainwashing (like the other children) if he doesn't sufficiently blend in. That gives a great source of conflict, especially if he only narrowly escapes permanent brainwashing; while also giving his Aunt chance to explain the history of the town, how it works etc. - especially given the apparent presence of adult males. 

Maybe there are a small number of other children who aren't permanently brainwashed but deliberately act that way in public to blend in and avoid arousing suspicion.

Note I deliberately said 'children' - while it's possible all the children are sissified males, it would be more likely for the girls to have been sissified as well to be docile, obedient etc. and not question the way of things. 
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funfayre
Addendum to the penultimate paragraph (since the site's playing up and won't allow me to save an edit to my post above):

Maybe there are a small number of other children who aren't permanently brainwashed but deliberately act that way in public to blend in and avoid arousing suspicion - especially if they've noticed that despite its oddities, Stepford is a quieter, safer and friendlier place than their previous town / village.
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Sissy_Fairy
Hey Tirias, thanks for the comments :3 I completely agree with you regarding to some of the stories on Sissy Kiss that have the main character submit to the changes within a matter of moments. While there will be a gradual change, it will not be a full blown change until the story reaches its natural climax. Of course Ryan will be broken down but it won't be a major break down.

Hopefully I'll have a chapter up later this evening :)
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
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Sissy_Fairy
I've read through your comments, and I must say you have hit the nail on the head with some of the ideas that I have introduced in the second chapter. I'm not going to be posting any of the spoilers and telling you what you've got right in regards to where the story is going to be going and what will be included, I'd like to leave some surprises.

Its almost as if we're on the same wave length. I love it!
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
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Sissy_Fairy

Sitting behind the counter of the shop with her nose in the latest catalogue of designs coming from Japan was a young girl around the age of eighteen. She had long flowing raven black hair, soft pale skin, bright green eyes and an almost infectious smile. Her lips were painted purple, and her cheeks were covered in slight blush. She wore a black and white dress, Lolita in style and with short sleeve blouse underneath that. A choker was wrapped around her neck made of lace in a striped pattern that matched the dress, and a headband with a bow that was just above her left ear. Her hands were covered in black lace gloves, purple nail polish coated her nails. Although they couldnt be seen, she wore striped stockings, again black and white and a pair of black Mary-Jane shoes. She was humming to herself, the music played through the shop was comforting, and very relaxing. It was one of her own CDs. She only took her nose out of the book when one of the customers that was looking at the row of dresses asked her a question.

 

Sorry Nicki, but that is it in terms of the dress sizes. Im afraid that the company that supplies our outfits have stopped producing that line. She responded in a calm voice and she chuckled shortly after hearing the groan coming from Nicki. When Helena returns well find out if she has managed to find another supplier. The dress she had been talking about was a mint green long sleeved dress with a lace back design. The girl was about to go back to looking through the catalogue when the door was opened. The bell on top of the door rang, the girl looked up, and most of the customers either looked over their shoulders or stopped what they were doing to see who was coming in. There were some looks of excitement as they saw the owner herself and a young boy follow her within the shop, closing the door behind him.

 

Miss Helena. I didnt think you would be back until tomorrow. The girl behind the counter said with a broad smile before closing the catalogue and stepping out from behind the counter.

 

I know. Unfortunately there were problems with the airline losing my nephews luggage. Helena responded before looking back to the white haired boy and bringing him forward. Lucy, Id like you to meet my nephew Ryan. Hes going to be here over the summer.

 

Hello. He said meekly. Ryan was clearly not well with strangers. Lucy had heard as much when she was talking to Helena about the latest addition to Stepford. He was cute in a shy sort of way. Lucy had watched many anime and read a lot of manga to see that it was going to take a lot to bring him out of his shell.

 

Hey there, welcome to Stepford. Lucy responded, curtseying in a somewhat clumsier than normal manner than what could be done, but it looked as if Ryan didnt notice it. He gave her a small smile and nodded his thanks. So Im guessing youre shopping for Ryan then. Lucy commented before looking towards one of the changing rooms. A customer had come out holding three dresses in his hand. Lucy still found it amazing that boys loved coming in the shop and wearing girls clothing, but she knew that was the way with Stepford. She had been in Stepford for two years and while she still wasnt used to some of the customs she was open to the idea that some boys liked to cross-dress. Oddly enough more boys did in Stepford than in other places.

She helped the boy with the dresses and took the one he wanted to purchase while putting the other away to be stored back on the clothing rail.

 

Im going to take Ryan in the back store and sort him some clothes out for the next few days before I can take him shopping properly. Helena stated with a smile on her face before placing both hands on the boys shoulders and walking him through the shop. Some of the customers were saying hello, and Ryan was returning the gesture by saying hello and introducing himself. Lucy thought he looked cute and was interested in getting to know him more in the future. You can hold down the fort for the last hour right?

 

Yeah of course. Ill shout if it gets busy. Lucy responded while ringing up the dress and getting a large bag to put it in. She saw the others walk into the back office and storage area, shutting the door behind them.

 

-X-

 

Ryans first impressions of the shop were mixed as soon as he entered the shop. It was light, airy, quaint and cute. Good music was always a boost. He recognised the sounds of Within Temptation playing through the speaker system as soon as he had a chance to listen to it. What made Ryan curious was the fact that looking around there were mostly dresses and blouses. No trousers or t shirts or jumpers. Cardigans were present as well as leggings and many pairs of boots and shoes. While the latter three were generally considered unisex the designs were made for girls more than boys. Maybe there were other parts of the shop though; Ryan was looking at the front area of the shop. Seeing the girl with black hair, Ryan did actually think she was cute dressed in what she was wearing, but he wasnt brave enough to say it and the introduction and just saying hello was more than enough for him. Even some of the customers, despite being young, some looking his age, others younger and older were being nice to him and actually saying hello. It was a welcome change in Ryans mind though. He was used to the fact that in England a lot of the customers were very rude. If you entered a shop the staff would say hello, but the other customers would look at you with indifference.
Walking around, saying hello to everyone Ryan had a chance to look at the rest of the store though he still found next to no signs of any clothing that looked even remotely styled for boys. Joining Helena at the counter, Ryan had the chance to overhear the last part of their conversation before walking through into the back of the shop.

There were two parts to the area they had just walked into. To Ryans left was a large office which he guessed his Aunt Helena used when she needed to get paper work done. Next to that was a staff room and a mini kitchen with a table and a few chairs as well as a toilet to the side of that. The rest of the area he now stood in was large space with multiple boxes stacked up. Some were full of catalogues, others were the stock orders that were waiting to be put out on the shelves and clothing rails out in the shop. The walls were covered in posters of various movies, anime series, manga series and different bands. Ryan could recognise a few of them. Bleach, Naruto, Digimon and Pokemon were some of them. Iron Maiden and Within Temptation as well as Nightwish and Lacuna Coil. There were a few posters that Ryan didnt recognise. He knew that they were bands from Asia judging by the writing. Imported. Helena must have got them in straight from her last holiday the previous year.

 

If you take a seat Ryan Ill be with you in a moment. I need to check to see if there are any messages. Would you like a drink? Helena asked as she made her way to the office.

Ryan was looking at some of the books on a desk that was against the wall. He turned his head and looked over his shoulder before nodding. Yes please. When Helena went off to the office Ryan sat down at the desk and relaxed, looking around at where he was. It hadnt started out as a good day so Ryan hoped it would end on a good note.

It was a few moments until Helena returned. She had a glass of what appeared to be orange juice in her hand and she had a smile on her face. Here we are. I remember you like your juice strong, but not too strong that it tastes horrible. She said while handing him the drink and sitting down on a sturdy crate opposite him. I have some good news, weve been invited to dinner tonight. Mayor Swanson is a good friend of mine and shed like to meet you.

 

Me? Ryan asked, amazed that anyone would like to meet him. His lack of confidence had given him the impression that no one would ever want to come and meet him. It was a bit difficult for him to even contemplate the idea of being interesting enough. Why me?

 

Well I was speaking to her about the fact that youre staying with me. Helena continued before relaxing against the table, leaning her arm on it before continuing. You see Stepford is a little strict. It has a system, much like the Visa and Green Card system that some countries such as the US uses. You have to apply to live in Stepford and have a character reference given by someone who already lives here. That or you have to be invited here.

 

How did you get in? Ryan asked before taking a gulp of his drink, hoping he didnt sound rude with his question.

 

I went to university with Mayor Swanson. As you know I studied business at Oxford University, and Elizabeth Swanson studied politics. We met at the first mixer of our year and became really good friends. At the time I had never heard of Stepford. She just said she lived in Ireland. Three years passed, and she and I went our separate ways. I returned to Southampton, she returned here but we still kept in touch. When she found I was looking to set up a business, she invited me to Stepford, offering me the chance to shine. Im glad I took her offer up. I dont think business would have been this good in Southampton, or anywhere in England for that matter.

Ryan listened to everything Helena had to say about her past, and how she arrived at Stepford. It was quite interesting. He knew his aunt went to Oxford but he never knew she met anyone that had such an important job as being the mayor. It also explained why she moved a few years ago to set up her clothes shop. He had finished his drink before speaking again, placing the empty glass on the desk.

 

So just everyday clothes and something formal will be on the list then. Ryan guessed with a small smile, though he was a little nervous seeing as he still hadnt found something that would be suitable for him. Looking at some of the boxes that were marked stock, some of them had exactly what they would be within the boxes. Again dresses and blouses, skirts and tops. A few corsets here and there as well.

 

Exactly. I have tomorrow off as well so well go shopping. Said Helena as she got up off the crate and dusted herself off. She reached across the desk and picked up the shipping notes that had come in from the past deliveries. She had two days worth to go through and at a quick glance, she had a curious look on her face before shaking her head.

 

Ryan didnt take it as a good sign. The knot in his stomach was paying testament to that.

 

Wait here for two seconds honey. Helena requested before getting up and rushing over towards the door that lead out onto the shop. A few moments passed and she let out a small sigh while walking back over towards Ryan. The knot in his stomach increased. I have some bad news Ryan. Unfortunately the male Lolita range we ordered in still hasnt come through. Apparently they phoned, sent an email to me explaining what has happened to the order, but I checked the work emails while out at the counter and there was nothing. I havent received a message and while Lucy did write down the number I cant get hold of them until tomorrow. And I have to phone early.

 

So whats going to happen? Ryan asked, nervous and a little worried.

 

Well for this afternoon you can wear what you have on. But for tonight, and tomorrow while shopping well have to find you something to wear from our current stock¦

 

Which is all designed for girls clothing. Ryan finished with a sigh before hanging his head and slumping his shoulders. It wasnt going exactly as he wanted. The day had gone from good to bad to indifferent and what could possibly be a social nightmare if anyone back at home would see him in Stepford wearing skirts and dresses. The Brightside was that it would only be for one night and a morning, so maybe it wouldnt be too bad. If some of the boys in the shop were wearing dresses and walking outside then perhaps he would be able to see it through until the morning. Letting out a small chuckle Ryan looked to his aunt, a small smile gracing his face. I guess I can endure it for an evening.

 

Thats very good to hear Ryan. Youre taking this in your stride. Well also get you a nightgown and some extra underwear while were at it. Theres no way Im letting you sleep in your underwear tonight and wear it again tomorrow. Helena stated and Ryan gave a nod of understanding. Helena had always been thorough in her hygiene. According to his parents they said she had an obsessive compulsive disorder when it came to cleanliness but so far Ryan had seen nothing to back that theory up. He knew that someone who sat on a crate without giving it a clean first did not have OCD. Come on, lets get you ready. Helena said before reaching to the top shelf of the desk, taking a folder marked staff requisitions. Within were numerous pages marked since Helena had opened her store. All the clothing that had been given to staff was marked down and the expenses that might come from them. It was only full by a quarter but Helena was thankful for that. Some of the dresses werent cheap. Okay, so well need a dress and shoes for tonight, not to mention stockings and accessories. A nightgown and some underwear for general use. Tomorrow well go with a blouse, a skirt, pair of boots and some stockings again and maybe a jacket for you to wear in case the weather goes cold. Helena listed the appropriate items in the book using the pen that was against the spine before putting it down.

Ryan remained silent through all of that. Unsure of what to say or whether he should say anything. Most of it would be inappropriate and he didnt like the idea of wearing a dress. He had agreed to it though and that was something he couldnt get out of now. It was happening whether he liked it or not. Helena got up and went to the back of the storage area, taking out a few boxes before looking up at the rows of shoes.

 

What size shoes do you wear Ryan?

 

Size 6. Ryan responded, ashamed of his small feet. Another aspect of his appearance that many bullies picked up on during his time at school, and something Ryan often hated hearing. He got up from the chair and walked over towards the stack of boxes that Helena was looking at. They were all in Japanese, and Ryan was amazed Helena could read it all. The only way he knew what size they would be was for the number six printed on the front label of the box. I have a question Aunt Helena.

 

Whats up Ryan?

 

How often do you get boys in the shop trying on dresses?

 

Quite often actually. Helena responded with a smile on her face before taking a few boxes of shoes down from the shelves and setting them to one side. There were four in total, stacked on top of one another and Ryan saw on the top lid the image of a pair of heeled lace boots made from what appeared to be black leather. I was quite amazed when coming to Stepford; both boys and girls wanting to come into the shop and try on dresses when I first opened.  Helena responded before walking to a clothing rail of dresses and started to shift through them. She glanced between the dresses and Ryan, trying to guess his size before looking back to a dress she had a hand on. It was pink, made from satin with puffed sleeves. The bodice was decorated with flowers on the front and the skirt went all the way down to reach just past the ankles. The hem of which had a long line of ruffled white lace. This should fit you. Helena muttered, more to herself than to Ryan before nodding her head and turning to face him. You should try this on. Go out onto the shop floor and use the changing rooms.

 

Wait¦ Im sorry Aunt I cant do that. Said Ryan, nervous at the prospect of changing and being seen by the customers. He knew that he shouldnt be so nervous seeing as the other boys were wearing dresses, but he couldnt do it. He isnt as brave as they are.

 

Theres nothing to worry about Ryan. I know youre nervous, and considering what youve been through I cant blame you for it. Helena said in a reassuring tone of voice before placing both hands on his shoulders. Remember what I told you about Stepford being different? Well it is true. Youre amongst friends. I didnt tell you this because I didnt know how you react, but seeing as you were quite polite to some of the boys in dresses out on shop then I know youll be fine. Stepford has the highest number of boys who cross-dress than anywhere in Europe. Probably the world. Stepford was created to help people be accepted for who they are and who they want to be. One of the laws of Stepford is that no one is victimised, everyone is welcome. Treat all as equals. The words were softly spoken, and they did the trick. Ryan was feeling a little more confident.

 

Okay¦ but you have to come out with me. Ryan stated and Helena chuckled and nodded her agreement before taking the dress from the hangar and holding it over her arm. Ryan lead her out from the storage area and into the shop floor.
The store was empty at that point. Lucy had taken a brush and was going across the floor, clearing up the dust and the small bits of dirt that had trailed in from the outside. She was humming along to the music again. Sweeping around the changing rooms she smiled when seeing Helena and Ryan walking towards her.

 

Has everyone left? Helena asked with a smile on her face, she noticed that some of the changing room booths had been left shut.

 

Yeah. Joel and Alexis were the last to leave. Joel brought the white dress by the way, along with the boots and the socks. Lucy told them while Helena opened one of the booths and placed the dress on the chair before stepping out and looking to Ryan, signalling for him to enter.

 

Thats good. He came in yesterday and tried the dress on. He looked good in it. Helena stated with a smile before looking at her wrist watch and nodded her head. Fifteen minutes. Lucy do you want to start locking up the shop. We wont have any more customers in from now and closing time.

 

Sure thing. Being honest I was going to lock up early if we were empty around this time. Im going out with friends tonight and wanted to get home and get ready. Lucy admitted before walking towards the front door and closing it shut, sliding the top bolt across and then the bottom, spinning the sign over and showing the rest of Stepford that they were closed for the evening.

In the changing room; Ryan had stripped down to just his underwear and was unzipping the dress. He had to admit the touch of the fabric felt good against his skin and he slid it up over his head before letting it tumble down his body. He slid his arms through the sleeves and started to shift it around so his head came out from the bodice. Despite being made for a girl it did fit him well, though Ryan put that down to the fact he already looked like a girl so when it came to wearing girls clothing that wasnt going to prove any difficulty.

Hows it going in there Ryan? Helena asked through the door of the changing room.

Could you come and zip the back up? Ryan called back before opening the door and walking out. He held the dress up against his chest to keep it from falling, and turned around so Helena could do what was asked of her. Ryan heard the zip as it was slid up his back, and when it was all the way at the top the dress fitted his body like a glove. Not too tight, nor was it loose enough that it moved around when he walked along. He could hear Helena giggle to herself at the sight of her nephew in a dress and he turned, seeing Helena give a small nod of approval.

 

You look so cute Ryan. It really suits you. Helena commented, causing Ryans cheeks to turn red as he took a deep breath, seeing himself in the mirror. With make-up and some styling to his hair he really would look like a girl. It didnt really give him a lot of confidence, but he wasnt going to voice his comments. Helena was happy, and the dress would be worn for one night and then it was gone. What was the worst that could happen? Now, lets get you undressed and well try on the outfit for tomorrow morning. Helena suggested before walking towards the outfit she had brought out. It was a powder blue lace skirt that reached down to the knees, a petticoat to go underneath and a white long sleeve blouse with lace cuffs and a Peter Pan collar. A ribbon necktie and a bow to go in his hair along with white stockings, a pair of heeled boots of faux white leather and a capelet in a powder blue that matched the skirt.

 

This is going to be a long afternoon. Ryan muttered to himself before walking back towards the changing room.

 

You know hes kinda cute. He heard Lucy comment as he started to move his body around to get undressed.

A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
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Sissy_Fairy
I'm quite amazed that I was unable to post it all in the same post. They really need to extend the amount of characters available per post. Six thousand characters too long. Oh well such is life.

I hope you enjoy chapter 2 :) I'll see if I can find a visual example of the outfits worn by Ryan.
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
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22 replies are left.
krystalasbaby
I enjoyed the beginning of your story, hoping for more soon please
krystala's sissy baby
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sissydina218
  love the way your story is started, really can't wait to find out what on the other side of the door. I really want to see how ryan becomes a sissy and how or if he enjoys it. thanks and keep up the great work
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Sissy_Fairy
Thanks :3 I should have more up soon.
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
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Sissy_Fairy
I think you'll enjoy it. I've got something planned for the shop and something that will give Ryan an interesting first look at Stepford. 
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
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sissieann
I like this town do they have any Sissy that are treated as babies????
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Sissy_Fairy
Posted by sissieann
I like this town do they have any Sissy that are treated as babies????

Oh they certainly will have :3 That will come soon in the next few chapters.
A sissy of satin, but not frills. A sissy of length, and not thrills. A sissy that is a princess, and not a baby.

I am the first of each. Long satin gowns that turn me into the Sissy Princess I wish to be.
Reply
Quote
 
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