PG Her first Sissy
Kat becomes a hostess for gentlemen with certain festishes
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 Her first Sissy

Chapter One

Kat was normally a bold and confident woman, but this was beyond her experience and well outside her comfort zone.

Kat was currently dressed in nothing more than a red and black Basque, a black satin thong, fishnets and suspenders and was perched on a pair of impossibly high heels.  She was also wearing full make up and a blonde wig.  In her right hand, she held a riding crop.

Kat felt utterly ridiculous!  How the hell did I get into this? She asked herself for about the billionth time.

Katherine Sprocket (Kat to her family and friends) had not had an easy life.  Born in Liverpool, her father had been injured in an accident at the factory where he had worked and her mother had had to become the family breadwinner. Kat had to look after her sick father, plus three younger sisters, and go to school.  Kat did have some things going for her though.  She was ferociously clever and hard-working and was not scared of anyone or anything.

At the age of ten, she managed to win the coveted scholarship to the Higham Academy for Girls.  There was only one scholarship available annually, and Kat was competing with other girls who were two or three years older than her, yet she came top. From Higham, Kat never looked back.  She was given a private education at no cost, became Head Girl and Captain of the Football Team, and from there went to Oxford Uni, where she was now a student, studying medicine to fulfil her dream of becoming a Doctor.

The costs had been high though, and in spite of trying to rein in her expenses, she was massively in debt.  One of the girls on the same course as her, Mel Appleford, told her about becoming a “hostess”, which entailed meeting male clients and taking care of their needs.

Kat didn’t like the sound of this at all.  It sounded like being a sex worker, with all of the seediness and squalor that implied, but Mel assured her it was all harmless.  There would be no sexual contact with the clients.  Moreover, the money was good.  Hundreds of pounds for about an hour’s work per client.

Kat wasn’t happy, but when she looked at all her bills again, she realised she had to do something. Prom was coming up and she needed a new gown, and shoes, and those did not grow on trees. So, reluctantly, she asked Mel how to get into the “hostess” business.  Mel took her along to a non-descript looking building in a street that was almost lifeless compared to the hustle and bustle of Oxford’s main thoroughfares.

Mel and Kat were admitted to the building via an intercom system and Kat was introduced to the Madam of the establishment, Mistress Fanny, a middle-aged woman who looked Kat up and down and beckoned her to follow her to her office.

The office was surprisingly business-like. Desk, chairs, computers, printers and an old-fashioned Bakelite telephone.  Mistress Fanny, dressed like a modern businesswoman in a pant suit and low heels, gestured for Kat to take a chair whilst she settled into her own throne-like seat.

Mistress Fanny asked Kat to talk about herself and why she was considering becoming a “hostess”. Kat gave her a very brief resume of her life to date and said in all honesty she desperately needed the money.  Mistress Fanny seemed satisfied.

Mistress Fanny explained that her business was to entertain men and allow them to fully explore their wildest fantasies.  The business was generated by online advertisements and a website, and also by telephone.

The service was very exclusive.  To become a client, a man had to register on the website, provide proof of his identity and submit to an interview with Mistress Fanny, who alone had the power to grant or refuse membership and membership could be withdrawn at any time for misbehaviour or other offences.

The business did not offer any sexual services whatsoever and the clients had to sign a contract that confirmed that they understood that.  The clients explored their fantasies through role-play, and that was where Kat would come into the picture.

All of their clients, without exception, were not just into cross-dressing, but into becoming maids, schoolgirls, little girls and even babies.  As hostess, Kat would be given a client profile with their particular fetish and take it from there.  She would order an appropriate outfit from the business’s stock of costumes and then role play with the client.

Mistress Fanny had begun the business over twenty years ago and now had well over five hundred clients on her books, and the profits were massive.  As well as having to pay a hefty subscription each month, the clients were charged well over the odds.  They were terrified that if their wives or girlfriends ever found out about their little secret they would be divorced or dumped quicker than a hot spud, so they were willing to shell out.

Mistress Fanny went on to explain that Kat would normally have to wear just a Basque and stockings but depending on the role-play could change into a stern schoolmistress, nanny or governess.  Mistress Fanny asked if Kat was still interested in the role.

Kat was frankly stunned by what she had just been told.  That grown men would actually want to be maids and schoolgirls baffled her.  Kat had been and was a tomboy.  Femininity was of course part of who she was, and it was instilled in all girls from birth, but that a MAN would want to become feminine……Kat shook her head in wonder.

Kat was mightily relieved that there would be no sexual contact and that Mistress Fanny seemed to have all her bases covered in terms of vetting the clients, and although she had some misgivings, she thought of her overdraft and maxed out credit cards and so said yes.

To protect her own identity, Kat adopted a new persona, Tiffany, and wore a long blonde wig (her natural hair colour was brown and it was worn short) and lots of make-up.  After shadowing a few of the other girls for a couple of weeks and learning her trade, Kat, or rather Tiffany, was as ready as she would ever be.

Chapter Two

Chris paced nervously.  This had been a big mistake.  He should never have come! He should never have given into his deepest desires and signed up to that website.  If his parents ever found out…..

Chris had been born the Honourable Christopher Henry Albert Chisholm, the only child of the Earl and Countess of Crayford.  To say that his parents were wealthy was an understatement.  They were obscenely wealthy, with a fortune that totalled millions and millions of pounds.

Chris had benefited from this of course. Private schools, private tutors, exotic holidays, an expensive wardrobe, a new top of the range sports car, and a monthly allowance that allowed him to live like a prince.

The only problem was that Chris would much rather be a princess!

For all of the privileges that he had enjoyed, one thing had been missing.  Affection.  His father, the head of a sprawling corporation, was much too busy with his own affairs to spend any time with his son, whilst his mother was the matriarch of the county set. Endless parties, soirees and tea with her ladies to put the world to rights in her little part of the world.  She had no time for her son either.

At home, the only attention he ever got was from the maids, Patricia. She had started as a young girl before Chris had been born, and become his unofficial nanny until he went to school. Patricia always looked very smart in her maid’s uniform and he always liked her better when she was wearing it, which was nearly all of the time of course.

In fact, Chris secretly wished he could wear a maid’s uniform too.  It was smart and pretty, but of course, boys were not allowed to become maids, especially when they were the heir to an Earldom and an unimaginable fortune.

Having no sisters and his mother’s wardrobe being totally out of bounds to him (she kept her room door locked), Chris had had no chance to dress up as a girl.  He supposed he could have pinched items from Patricia but he had too much respect for her to do that.  She was his only friend when he was home.

He tried, in vain, to land female roles in the school play, but he was not considered to be a good enough actor to play Juliet or Lady Macbeth.  In fact, he was banished to being a stage hand in school productions, much to his disappointment, and had to watch from the side-lines as another boy swanned about in a period gown and lapped up the kudos.

Now Chris was at university, studying Chemistry.  He had a girlfriend from the same “set” as him, a Lady Portia Dupont.  He had no idea why they were together.  She was stuck up and self-obsessed, and Chris was laid back and obsessed with exploring his own femininity, and not really interested in her.  He dared not allow Portia to know his secret.  Her family knew his family and Portia couldn’t keep a secret to save her life.

So, when Chris found a website called “Wonderland Transformations – where boys can become girls”, he seized upon it like a drowning man would seize upon a lifejacket.  The rules were pretty strict and Chris had to have an interview with a fierce looking woman and sign a contract saying he would abide by the rules at all times.  It was expensive too, although that was not a problem.  In fact. Chris’s allowance had just been increased following his 21st birthday so Chris would not miss this particular item of expenditure – it was almost like a birthday present from good old Dad.

As far as he could discern, Wonderland offered him what he wanted and what he wanted was to become a maid.  Like Patricia.

This was what he had wanted his entire life, so why was he so frightened?

Chapter Three

Kat studied the client profile she had just been given very carefully.

The client was aged 21. The same age as her.  He was five feet and eight inches tall in his socks, he had wavy blond hair and blue eyes.  There was a photo attached that confirmed the last two details.  He was clean shaven and had an upper class look about him.  Someone who had never had to worry about money in his life.  He looked vaguely familiar.  His current occupation was student and it was then that Kat realised why he was familiar.  She had seen him around the uni campus with some stuck up looking cow, another aristo. Kat was doubly glad that she was unrecognisable under the wig and heavy make-up.

So much for the basic facts, what Kat needed to know was what this Chris wanted.  

Under the heading “client expectations”, Kat read:

Maid Training and service.  The client wishes to experience being a maid servant.  He wants to dress fully as a maid and be ordered about by the lady of the house.  He will be meek and submissive. As the lady of the house, you are to teach your maid her duties, instruct her and discipline her for any mistakes or infractions.

Costumes: The client will wear a complete maid’s outfit and the lady of the house will be dressed as a lady in the late Victorian period.

Although Kat had never had a maid, during her shadowing period she had seen enough male maids to understand what she needed to do. Male maids were the most popular fantasy of the clientele.  Powerful, rich men seemed to have a need for becoming servile maids.

On her PC, Kat ordered a Victorian maidservants uniform, complete with petticoats and undergarments, and a Victorian ladies’ costume, also with petticoats and undergarments.  Kat had never worn a corset or petticoats, so this would be a new experience for her too.

The costume department had both Kat’s measurements and those of her client and it held stock in any size, so Kat did not have to worry about the clothes being the wrong size, and the costumiers were extremely efficient.  The clothes would arrive in about fifteen minutes. 

In the meantime, Kat had to go and meet her client, her very first client, wearing almost nothing at all and as nervous as hell.

Kat had been told that the client had arrived five minutes earlier and that he was awaiting her in reception. Reception was a professional looking business area. Anyone who was not aware of the true nature of the business would assume that it was just a normal business selling insurance or double-glazing.

Kat took the lift down two floors and stepped out into the reception area.  It was busy.  Apart from the two girls in business skirts, blouses and heels manning the desk, there were about half a dozen clients waiting for their hostesses.  Kat could feel twelve male eyes taking in her shapely, scantily clad body.  Inwardly, she shuddered.  She did not want to be a sex object.

Ignoring the other men as much as possible, she made a beeline for her client, Chris.  Chris was wearing a white shirt and slacks.  He was quite handsome, Kat decided, although a little shorter than she liked. Kat liked tall guys, the taller the better!  He also looked scared out of his wits.

Kat approached him and extended a hand “Hi Chris, welcome to Wonderland. I’m your hostess, Kat, and I’ll take good care of you during your appointment”.

Kat had tried to sound as friendly and welcoming as she had been trained, but Chris was scared, and flustered and looked ready to bolt for the exit. He took her hand and shook it limply.  He was trembling badly and seemed to want to say something, but no words would come out.

The poor thing is petrified!  Kat instantly felt sorry for him, but decided to take charge of the situation.  She still had his hand, so she almost dragged him to the lift.  Chris seemed to want to protest, to pull away and make a run for it, but Kat didn’t give the chance.  She guided him into the lift and they rode it to Kat’s room.

Still holding his hand, Kat steered Chris into the room.  As she had hoped, the costumes had been delivered.  A maid’s uniform and a Victorian ladies’ outfit were hanging in the wardrobe.

When he saw the maid’s uniform, the holy grail he had been questing for his whole life, Chris let go of Kat’s hand and plucked the outfit out of the wardrobe.  It was love at first sight, Kat realised.  Kat was less enamoured of the outfit she would have to wear. Corsetry, petticoats and a heavy dress.  She would ironically be more uncomfortable than her maid.

Kat spoke to Chris “Girl! You will get into your uniform this instant!” she snapped.

To Kat’s surprise, far from being offended, Chris seemed to be pathetically grateful to be told what to do.  He peeled off his male clothing in double quick time and in a few seconds was naked.  He stepped into his frilly bloomers, pulled thick black stockings up his legs, donned a cotton chemise and then the maid’s dress, cap, frilled apron and clunky black shoes with small heels.

Kat was secretly impressed as how quickly and how naturally, Chris donned his maid’s uniform, but had to remain the stern mistress.  She pointed to the pile of discarded male clothes “Put those things outside the door” she ordered him.

“Yes, Ok” Chris said, beginning to gather the clothes.

“Yes what?” Kat demanded.

“Yes, yes mistress” Chris answered.

“Better. You will address me as mistress from now on, understood?”

“Yes, mistress”.  Chris placed the male clothes outside the door and closed it, and then turned to face Kat, waiting for further orders.

Kat made him wait.  She stripped off her Basque, her thong, her stockings and her shoes.  Her feet and her bum were aching and she was glad to escape from having a thong riding up her bum and the torture of perching on six inch stilettos.  She was naked before him.

“One of your duties as my maid is to help me dress. So, help me dress!” Kat ordered him.

Chris helped her into her clothes.  Bloomers and chemise, then being laced into her corset, then layers of lacy petticoats and then the green and gold dress.  Kat could feel Chris’s mounting excitement as he helped her into each item of clothing.

Being a maid was not just a service, Kat realised, but a privilege.  No-one other than the maid of a lady could ever see her naked, or in any state of undress.  Only the lady and her maid knew what she wore beneath her voluminous skirts and petticoats.  It was a shared secret and deeply intimate.

Kat had relaxed and so thankfully had Chris.  They were now both very comfortable in their new positions.  Starting to really get into her role now, Kat ordered her maid to sweep the floor.  Chris eagerly picked up a small hand broom and dustpan and set to work.  Kat sat back and enjoyed watching his skirted posterior wiggle as he worked, then something occurred to her.

“I say, girl” she addressed the maid, putting on a posh voice.

Chris looked up, his face slightly flushed from his exertions “Yes, Mistress?”

“I can’t keep calling you girl, even though you are one. What is your name?”

“Uhh…Chris mistress”

“No, you silly goose! That’s a boy’s name.  You’re not a boy, are you?”

“No, mistress” Chris asserted.

“Right.  Now we’ve got that sorted out, what is your name? Christine? Christina?”

“Patricia” Chris said “My name is Patricia”.

“Patricia. Right. No-one told you to stop working by the way!”. Patricia began sweeping furiously.

Things were going splendidly, Kat decided.  Patricia seemed very happy and Kat was even enjoying herself.  It was not every day you got to be a lady and have a maid dress you and attend to your every need, not matter how small.  Kat rather liked it.

Kat made Patricia serve her tea and then go and clean the ladies toilets from top to bottom. Patricia was very obliging.  The tea was perfect and the toilets were spotless.


Unfortunately, the same could not be said for Patricia.  Her frilled apron was creased and stained from her exertions and she was sweating.

Kat toyed with the idea of punishing her maid, but they were out of time. Chris’s appointment was over and Kat had another client due in twenty minutes.

“That’s all for now Patricia.  Go and get changed out of those filthy things”.

Patricia bobbed a small curtsey “Yes mistress. Thank you, mistress!”

Kat watched with amusement as the maid transformed back into a young man and said his goodbyes.  He seemed happier and more confident. Kat was sure he would return.  He made a great little maid.

And he was rather cute!

Chapter Four

Chris did return. Quite often.  He became Kat’s most regular and important client and she had earned a bucket load of money from Chris alone, let alone the other clients.

Chris was also Kat’s favourite client.  The other men she had to entertain were mostly middle-aged gentlemen who wanted to relive their schooldays, but as schoolgirls in short skirts and wishing to be spanked.  Maids were a popular fetish, and one of her clients wanted to be a baby.  It was a sight to see a 60 year old man in a nappy and a bonnet and sucking a dummy, but that was what he wanted.

Kat looked after these men but she had no affinity for them as she did with Chris.  After a few months of having Patricia waiting on her hand and foot, Kat sensed that both she and Chris were becoming slightly bored by the routine, so Kat made the bold decision to make some changes.

Instead of ordering the maid outfit, Kat ordered something else, and she ordered a different costume for herself too.  Normally, hostesses were not supposed to deviate from the client profile, but Kat knew Chris pretty well by now and gauged he was ready for this change.

So, when Chris arrived ready to become Patricia the maid, he was confronted by a completely different outfit.

Hanging in the wardrobe was the outfit of a small girl of around seven years old. A white dress with a royal blue sash around the middle, lace petticoats, frilled ankle socks and shiny black mary-janes.

Plus the knickers, which were a sight to behold.  They were pink rumba panties, with lashings of white lace and pink bows.

Chris looked at the ensemble in astonishment “What’s this?”

“Your new clothes.  I don’t want you as a maid any more Patricia, I want you to be my daughter. Can you do that?”

Chris was stunned by the new clothes, but he nodded.

“Good girl, Patricia.  Let’s get you into your clothes”

A few minutes later, Patricia was wearing her pretty dress, petticoats, ankle socks and shoes.  The outfit was very different from the maid uniform. For one thing, Patricia’s legs were bare, and for another, her frilly knickers peeked out from beneath the skirts of her dress.

It must be very disconcerting for a boy to have his legs and knickers on show Kat decided.

Kat was wearing the dress of a housewife from around the 1950’s with a girdle and apron.  Very motherly.

“Now then, Patricia, do you like your new clothes?”

Patricia’s head was down and she seemed unhappy.

“Look up, Patricia! Hold your head high and look at yourself in the mirror.  You are a very pretty little girl and very adorable”.

Patricia did as she was told and she could see what her mummy saying was right.  She looked beautiful in her dress and she liked seeing the frills of her own knickers.

“Mummy, I look lovely!”

“Yes, Patricia, you do. Now, go and play with your dolls like a good little girl”.

Kat had arranged for some dolls and other girls’ toys to be delivered. Patricia tottered over to them and began playing with them, giving them names and talking to them, just as any normal little girl would.

Kat was both surprised and impressed as how quickly Patricia slipped into her new role.  Presently, she went and joined her.  After years spent looking after her sisters, Kat knew how to play with little girls. Patricia was ecstatically happy, especially when Kat took her on her knee and kissed and cuddled her darling little daughter.

By the next appointment, Chris had changed his preference from maid to little girl.  Kat got Patricia more elaborate and ever frillier dresses, tied ribbons in her hair and spanked her with a hairbrush when she was naughty.  Patricia sometimes played up deliberately for a spanking.

Patricia became the perfect little girl and Kat wondered how far she could take this.  Could she enrol her in ballet lessons? Make her a bridesmaid or a flower girl?  Patricia was open to anything Kat suggested and was a natural as a little girl.   Patricia gushed girlishly and even moved like a girl.  She liked her hair ribbons and pretty dresses.

Kat thought he was the most adorable girl in the world.

Chapter Five

More time passed, and the mother-daughter relationship between Kat and Patricia became deeper.

Which was a problem, because Kat would have to give up being a hostess very soon.  It was her final year at uni and with final exams looming, Kat needed to concentrate full time on her studies. Plus she had to find a job for afterwards.  Thanks to the hostess job, she had virtually cleared all of her debts, so there was no financial need for Kat to continue as a hostess.

But what would happen to Patricia?  If Kat left, another girl would have to become her “mother”.

On Chris’s next visit, dressed as Patricia again, Kat sat her down and explained that she would have to leave.  Patricia was distraught “You can’t leave! You’re my mummy!”

“I am sorry, Patricia, but I have to leave.  You have a dream to be a girl right? But I also have a dream, to be a Doctor and help people. Do you understand?”

Patricia nodded.

Kat patted her on the head “Good girl”.

All seemed to be well and Kat and Patricia parted on good terms.

Then, twelve hours later, Kat was woken by a call from Mistress Fanny. Patricia was in hospital, having tried to cut her own wrists.  Thankfully, one of Chris’s roommates had stopped him.  Kat went to visit him in hospital, but he seemed sullen and uncommunicative as if he considered that Kat had betrayed him.

Kat felt ashamed of herself.

Wondering what to do about the situation, Kat went online and searched.  It took her some time but…eureka!

Dr Katherine Sprockett, as she now was, finished her last shift for the week, got into her car, and drove for almost four hours until she reached a large country house in the middle of nowhere.

The large sign outside read “The Princessa Academy for Girls”.

Kat’s car made it up the long driveway until it reached the main house, which dated from the 18th century, where she was met by the Headmistress of the Academy, a Miss Jeffers, and taken inside.

Kat looked around.  The place resembled the same girls’ school where she had been educated, but with one crucial difference.  None of the pupils here were girls.  Sure, they looked exactly like girls, with their long hair, delicate complexions and skirts, but all of them were genetic males.

Kat had found the place on the internet.  Princessa was in fact a code name for a government social project.  The ministry of Education were so concerned by the fact that boys were falling so far behind girls at all levels of education that they sanctioned this experiment.

Taking troublesome boys of all ages, they were sent to Princessa and educated as schoolgirls.  Miss Jeffers said that although many boys resisted at first, they eventually submitted, and the experiment was a great success. The behaviour and exam results of the boys was markedly improved as a result of feminisation.  After a few years, those judged to have improved sufficiently were released and allowed to be boys again.  Funnily enough, some of the boys chose to remain as girls!

Kat could see the success of the experiment for herself.  All of the pupils she met were courteous and polite and focused on their studies. Perfect young ladies in fact.  Most of the “girls” had been unruly, disruptive and violent before being sent here. Crime would fall and the boys would become useful and productive members of society as a result of a little petticoating.

The pupils were of all ages from leggy sixth-formers in their short skirts right down to toddlers in their gingham uniforms. 

But there was one very special pupil, who had committed no offence, but who was happy as a little girl, and it was this girl that Kat had come to see, as she did once a month.

Patricia, dressed in a very lovely frock and with her ribboned hair in ringlets, was playing with her friends.  Boys of between six and eight dressed in a similar way to Patricia, and very docile and submissive towards Patricia.

When Patricia saw Kat, she screamed with joy and threw herself into Kat’s arms.

Kat felt blessed to know this little girl.

The End



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A very nice story 
really enjoyed your story. 
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