sissy maid looking to be trained

Poor Christopher. At 23-years-old he still lived with his mother. But she was away for the week, so he thought he would indulge his very secret cross-dressing fetish. He had kept it a very closely guarded secret ever since he was young. Anyway, as his mother was away, he decided to dress up in some secretly bought underwear he had purchased for this very week, and even a special collar and cuffs set and gag. He foolishly locked his wrists in the cuffs that were attached to the collar, confident he could get himself out of them. He was planning to spend an afternoon mincing around the house, and end the day with a long slow pillow hump. But his afternoon interruptedby the sould of car wheels pullingonto the gravel driveway. It was his Auntie Janice. And he knew she would just let herself in. He started panicking, but thought if the cuffs off he could run upstairs before she saw him and get changed. But all too predictably, he couldn't release himself. Instead of running upstairs to his room where he could take his time he remained in the living room, not thinking straight. Then to his horror she rounded the corner and entered the room.

Initially Janice was shocked and stood there in stunned silence with her hand to her mouth. Christopher just stood there like a rabbit in the headlights. On one hand it was a disaster for him, his shameful secret now exposed. On the other, it was a dream come true. He had long fantasized about being a sissy maid for his auntie, and even his mother, but the all too familiar shame of such naughty fantasies would always have him feeling bad about thinking such things, and what his auntie and mother would think of him if they knew. But when he saw her hand lower from her mouth, and saw the growing smirk on her lips he instantly felt an electric jolt of excitement flash through him. And almost instantly, he was erect again. She laughed as she noticed his embarrassingly small 'manhood' barley stretched his knickers. She circled around him like she was circling prey, until finally she spoke. 'Well, well, well. Did I interrupt something?' She said, her voice dripping mocking glee.

'Mmmmph' was all Christopher could manage from behind his gag. Causing more laughter from Janice.

'Tell me, does your mum know about your little hobby?' She asked with a beaming smile. Christopher slowly shook his head.

She giggled and said, 'I didn't think so'. She paused for a second then took out her phone. 'Why don't we change that?' She laughed, then started taking pictures of him, lots of pictures. She spent an inordinate amount of time taking photos after photo, from angles, and close ups of his excited clitty underneath his knickers. Christopher moaned his desperate pleas for her to stop through his gag, which she simply laughed at and teased him further by saying, 'Awww, I'm nearly done sweetie, just a few more'.

After drawing out every bit of humiliation she could from the pictures, Janice moved in close to Christopher, who although was still moaning his pleas through the gag, but at the same time was maddeningly aroused, and was on the verge of squirting his cream in knickers. As she brushed up beside him he looked down at her phone, and to his utter despair she was on the messenger app and was uploading photos ready to send. She then started typing and cheerfully read aloud what she'd written, 'Hey sis, I found Christopher indulging in a little hobby I think you'd be interested in. The poor thing is all a fluster, and I think he is about to have a little accident if he's not careful. What do think I should do? Love Jan'. Christopher was now shaking his head desperately now, trying in vain to get her stop, and desperately hoping she was just teasing him. But of course, she wasn't. And with the most soul crushing of little grins, she held up her phone and so very slowly tapped the send button. This time it was a horrified squeal that Christopher produced from behind his gag, to the absolute delight of Janice, who clapped with glee as real tears of frustration and humiliation ran down his cheeks.

Janice then turned her attention to his less than impressive erection. She moved to the side of of hom and and looked down at slightly stretched knickers, and asked, amid many giggles, 'tell me darling, have you ever been with a woman. Come on be honest'. Christopher looked down and slowly shook his head. Although he had a very strong cross-dressing and sissy fetish, he still held paradoxical strong male desires and hated his underwhelming organ. She laughed as he shook his head in answer to her embarrassing question, and replied amidst many giggles, 'It's probably for the best sweetheart, I mean, we'll, I'm sorry Christopher, it's pathetic!'. She almost fell over laughing, and by this point Christopher was just standing there absorbing the humiliation like a sponge, and trying to process his genuine anger at his auntie's non-stop and very successful attempts at humiliating him. But at the same time he'd never been turned on, and dangerously close now to a full orgasm into his sensual satin knickers. She knew that too, as she could see the spot of pre-cum coming through the glossy surface. And slowly she started moving her hand to his now desperate clitty.

He screamed a muffled 'no please' through his gag, but she simply giggled as her fingers gently touched his panties and through them his stiff little sausage. He was squealing and shaking his head, trying to get her to stop. But it was futile. She had the bit between her teeth, so to speak, and was determined to humiliate him as much as was possible. She ever so gently stroked his peenie through the smooth satin and said in sweet toned whisper, 'what's the matter sweetheart, don't you like your auntie stroking your cocklette?'.

But this was her misunderstanding, she thought he was so desperate for to stop humiliating him as she was his auntie, what she didn't understand was just how close he was to spurting his cream. She had seen how aroused he was and ashamed he was, and was just starting to question to herself how far she had taken things and was just about to stop her cruel teasing of his clitty. It was then it happened. After only 30 seconds or so of her gently stroking and tickling his lollipop, he stated bucking and spasming and all of a sudden she felt the warmth of his cream the the satin. Jet after jet until it started seeping through the satin and dripping from her hand. She could only look in shock at his sissy juice, now dripping onto the floor.

To be continued.

going to university was his dream - he would get a good degree and get a fantastic job from it. he worked hard, his grades were excellent. he had very little social life - he needed to study, even so everything in the city was so expensive. especially rent.

he tried his best to make sure he never fell behind on the rent. first time it happened his landlady was fine about it. second time - she made him an offer that he could earn some extra time to pay by doing chores around the house.

thus began the slippery slope from being a student to sissy.

the next time he was short with the rent the landlady told him he would have to do his chores dressed as a maid and she would offer his cleaning services to the other guests.

it didn’t take long for the prim and proper maid’s uniform to turn into a sexy one, and from there it didn’t take long for some of the guests to start inspecting his work and saying they would report him if he didn’t let them fondle his legs and arse.

the next step didn’t take too long.

soon he was servicing the guests with his mouth, it wouldn’t be long before he was being bent over and having his ripe virgin back passage stretched

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A true story.

My wife Belinda has a very high-powered job on the trading floor in the City of London.  She dresses for work in beautifully tailored, very expensive power suits – usually a pant suit but sometimes a skirt suit.  She pays £500 for designer high heels and £480 to have her light brown long bob cut and styled regularly at a top London hairdresser near her office building.  She can afford it.  Belinda is paid a lot of money but works very long hours.  She is on the trading floor before 7:00 am most mornings, and often needs to go out and socialise with clients until late in the evening.  Her clients are billionaires and require a personal service in the handling of their very large share portfolios.

As a primary school teacher, I naturally get paid far less, and with all the government interference in state schools my job was becoming increasingly stressful and less rewarding.  So I guess it was logical that when we had children, I would give up my job, which by that time I loathed, and stay at home to look after the children.

When George and Samantha were babies it was okay, although I did find it embarrassing to go to the mother and baby groups with the young mothers.  When the children got to school age, I began to hate being the only man standing at the school gate waiting for the children to come out.  The expressions of the mothers who I caught staring at me, but who looked away when I met their gaze, ranged from mild puzzlement to open hostility and even disgust.  It was so humiliating.  I didn’t feel like a ‘real man’ any more.

I discussed my problems with Belinda, and she listened sympathetically, but the idea that I could go back to teaching and she would give up her extremely lucrative profession was unthinkable – we simply couldn’t manage without her very generous salary, as we had a huge mortgage on our house in St John’s Wood.

My wife didn’t come up with any practical solutions but suggested that I was run down and maybe vitamin pills would help.  She said she’d get some for me.

It was after taking the pills for about six months that I started to notice the changes.  My breasts seem to be getting enlarged and my nipples were feeling tender, and the distribution of my body fat seemed to be altering. My hips were widening, and I was putting on weight on my thighs.  My wife at first assured me that it was probably just lack of exercise.  I didn’t do much physically beyond ALL the housework, cleaning, doing the shopping and walking twice every day to the school gate.  (Actually, that sounds like quite a lot of exercise and hard work, as many stay-at-home mothers still know.)  She suggested maybe I should take up jogging on join a local gym.  I had no enthusiasm to do either.

Belinda could see how unhappy I was.  Finally, she announced: “I am going to suggest something that might sound silly, but will you give it a try for me?  Let’s call it a sort of experiment.”  She went upstairs and brought down a package tied up in pink wrapping paper and a pink bow. “I want you to go upstairs and put on what’s in the package and also the clothes I have laid out on the bed for you.  I went shopping up Oxford Street in my lunch break.”

I took the package and went upstairs to our bedroom.  On the bed were laid out a black mini skirt and a cream silk blouse, and a pair of sheer black tights.  I opened the package. Inside I found a pair of black lacy panties and a matching bra. I looked and looked at the female clothing in astonishment.  What on earth was Belinda playing at?  I sat on the bed and burst into tears.

Belinda came into the bedroom, sat down next to me, putting her arm round my shoulders.

“Come on, love, this is just something I want you to try.  Let me help you.”  I undressed and Belinda helped me into the bra and did it up at the back for me.  My new breasts seemed to fit snugly into the bra cups.  I slid the silk panties up my legs and rolled on the tights, after my wife had explained how to do it, then stepped into the mini skirt, put on the blouse, and she helped me do up the buttons, as my fingers felt clumsy.  Belinda sprayed some of her Dior scent behind my ears, then went to the wardrobe and produced a pair of Jimmy Choo black high-heeled court shoes.

“Sit down on the dressing table stool, love,” coaxed my wife, tapping the fluffy faux fur top of the stool with her hand.  She combed back my hair, which had grown quite long, as I hadn’t had time to get it cut for quite a while. She put it into a pony tail with a black elastic scrunchie. “I’m going to make up your face,” she said.  She explained what she was doing, applying foundation, eye makeup to my lids, and outlining my eyes with a black pencil.  “This is called kohl, it’s an eyeliner,” she said. She applied mascara to my lashes and lipstick in a shade of lustrous red to my lips and completed my makeup with a touch of blusher to my cheeks. Then she removed the scrunchie and brushed out my blonde hair, which had grown to near shoulder-length.

“Slip on the shoes,” she said. I put on the black stiletto court shoes.  It felt very strange, wearing high heels.  Belinda opened the wardrobe door, which had a full length mirror on the inside. “Have a look,” she said. I stood in front of the mirror, and saw an attractive blonde woman looking back at me.

“What have you done to me?”  I felt tears again brimming in my eyes.  I wasn’t sure whether it was from shame, humiliation – or a strange emotion I couldn’t clearly identify.  Was I a bit turned on and at the same time almost grateful for what my wife had done to me?  How could that be? I was a man, wasn’t I?

“What do you think of yourself, dressed like this?  You make a very pretty girl!”

I didn’t know how to respond. I felt confused but also strangely  - excited? I was reluctant to admit it to myself, as if I had crossed some forbidden barrier that should not, ever, be opened to those born into the male sex.

“Stay like it for now, love.  Come downstairs and let’s watch something on Netflix.”  I found it quite hard to go down the stairs in high heels, but managed it somehow without falling headlong.

I sat down on the sofa and looked down at my nylon-clad legs in the mini skirt.

“Can I do your nails?” Belinda asked.  Before I could reply, she produced some red nail varnish from her handbag, took my hand, and proceeded to paint my nails.

We watched a science fiction film, then went up to bed.  On the bed there was a baby-doll nightie of burgundy silk. “That’s for you tonight,” she said.  “Will you put it on for me?”

We had the best sex that night for a long time. Gentle, passionate. We both orgasmed repeatedly.

The next morning was Saturday.  We took the children for a sleepover at grandma’s. Belinda announced: “We’re going shopping.  Will you wear again the mini skirt and blouse?”

‘

I’ll look ridiculous. Everyone will know I’m a man.”

“I don’t think so – you pass very well as a woman.  No-one will think anything other than that you are a very attractive woman.”

“I don’t know - ”

“Try it, for me.”

So off we went to Covent Garden, where we had a coffee in one of the up-market coffee shops.  “To give you confidence,” Belinda explained. Then we hit Oxford Street and the stores.  Belinda helped choose skirts, dresses, shoes, lacy underwear, including even a silky suspender belt and sheer stockings; more nighties, coats, handbags – a complete female wardrobe - for me.  I even went in the ladies’ changing rooms to try on some of the clothing for size. The shop assistant who gave me a token for the number of items I was trying on did not give me a second look.

After our shopping, we went for a drink and something to eat in Blame Gloria, a swanky basement cocktail bar. Belinda looked across the table at me, as we drank Porn Star martinis.

“Would you like to stay like this forever – be my girl?”

I didn’t reply.

I gulped down a lump of the ice and used the straw to suck up a big slug of my drink, feeling immediately the heady hit of the vanilla-infused Eristoff vodka and passion fruit liqueur.

When the children came back from grandma’s on Sunday, I was still fully dressed as a woman.  Belinda brought me into the living room.  George and Samantha stared at me in amazement.

“This is your new Pa,” my wife explained – “she’s no longer called Alan.  Her name is Alice now, but she is still your father, and you can still call her Pa – or Alice, if you prefer.  She is going to be a woman from now on.”

That’s news to me, I thought.

It is amazing how accepting children of nine and seven can be.  It is amazing how accepting I was.

“Okay,” said George.

“No problem,” said Samantha, with all the maturity of a confident nine year old.  “We know all about transgender people. There’s a trans boy in my class, who always come to school dressed as a girl. Her name is Kylie. She has long hair and plays with me and the other girls on the playground. “

“Can we go and play on the X-Box now?” asked George.

The kids hurried off into the study to play on the X-Box.

“I don’t remember saying I was agreeing to be a woman from now on,” I said.

“I love you more than ever as a woman,” replied my Belinda. “Give it a go for me, love. There’s some advantages, you know.  For one thing it will be much easier for you, standing with the other women at the school gate, for example. And it will be much easier for me to have a wife to take care of things at home, as I work such long hours.”

Well reader, you have probably guessed the rest. Belinda took me to Marbella to have facial feminisation surgery.  Dr. Luis Capital and Dr. Daniel Simon performed the feminine brow sculpturing, lip lift, and liposuction under my jaw, while a German plastic surgeon whose name I forget carried out my nose job. The nurses at the Marbella clinic were wonderful, and I was also looked after by Lilia Koss, a very friendly and supportive American lady who worked as English-speaking liaison for the Facial Team.  Lilia was married to a Spanish guy. They lived in a little Andalusian village a few miles from Marbella.

After the FFS there was no turning back. I continued with the female hormones (I had already guessed they weren’t ‘vitamins’).  My wife urged me to complete my feminisation.  She persuaded me to visit our GP, who referred me to the NHS Gender Identity Service at Charing Cross Hospital.  

I arrived at the first meeting fully dressed as a woman (I had been living full time as a woman for over nine months), so it was no surprise that I was diagnosed as having gender dysphoria. They assumed I would continue with the female hormone treatment, prescribing Estradiol – 4 mg a day – which was free on the NHS, although we could have afforded to pay for it privately of course.  

It was understood that there was no doubt that I would proceed to full sex reassignment surgery.  I didn’t seem to have much say in it - I just went along with it all. I concluded that as my wife had been able to feminise me so easily, I really must have gender dysphoria, although it’s not a term I care for much. I must have wanted to change my gender, deep down.  The subconscious is a funny thing.  Sometimes we don’t even recognise our own deepest yearnings.  Had I always wanted to be a girl?  Did the fact that my mother had sometimes dressed me up in my sister’s clothes have anything to do with it or was I born this way?  Who knows?

So, I accepted my fate.  I went down to the private Nuffield Health Hospital in Brighton, and stayed there for ten days, to have the sex reassignment (or gender reassignment – or ‘gender confirmation’) surgery.  (I never know whether it is correct to call it SRS or GRS or ‘Gender Confirmation Surgery’, as they seem to prefer in the U.S.)  The surgeon was one of the top U.K. consultants for sex change surgery – Mr. Thomas.  He was very kind, as were the nurses.  Of course I had to wear a catheter for the first five day after the surgery, then the day came for the plaster bandage to be removed.

“There we are dear,” announced the nurse, ‘you’re a girl!”  The nurse was called Tracey, a pretty, slightly over-weight, brunette girl who had been caring for sex reassignment cases for several years. The catheter was removed and I peed for the first time sitting down.  “That’s the way you will always be peeing in future!” announced Tracey, with something akin to glee.

Belinda and the children stayed in a hotel nearby and came to visit every day. Unusually in view of her high-powered job, my wife had taken time off to be with me while I was undergoing the surgery.

I was naturally a bit sore ‘down below’ for several weeks, but it was surprising how fast things heeled up and looked ‘normal’ down there.  After three months, you really wouldn’t have been able to tell my new vagina from any other woman’s.

Belinda delighted in seeing me in my panties and bra when I was getting dressed, particularly how femininely smooth and flat my crotch looked now, and how well my boobs had come on, although she still urged me to have implants to make my chest a bit bigger. Eventually I gave in and now can easily fill a D-cup.

Well dear reader, that’s the end of this part of my story.  

I am not sure why you are reading this, which is all true, and as it happened. Perhaps you are a poor male who wishes it could happen to him?  Even without a beautiful wife like Belinda to feminise you completely, it can still happen to you if you really want it enough.  

Do you?

© 2019 Amber Goth & Kate Lesley

(Some of my readers may be wondering - did this really happen?  Yes, it did.  Most of it, and particularly the details of the facial feminisation surgery, sex change surgery, female hormone treatment - I have personal experience of - it really happened to me.)

If you enjoyed this story, you will certainly love my book of classic transgender fantasy stories, available from Amazon:

Kindle version: How Stephen became Stephanie and other Transgender Tales

Paperback version: How Stephen became Stephanie and other Transgender Tales

Reviews on Amazon

best trans fiction ever

This book is a collection of beautifully written stories exploring transgender themes. Here you can read the fictional accounts of ‘boy meets girl and boy wants to become girl and find true happiness and fulfilment. Then sheer pleasure as you are transported to the primeval forests of thirteen hundred years ago in ‘The Lady of the Lake’. Then hold onto your seats, just try 'Virtual Reality Woman’ which takes you to another dimension. All the stories are set in a variety of situations and the descriptions give real focus and depth. I would recommend this amazing book to anyone trans, also partners, wives or friends who would enjoy these stories.

Nice collection

A very nice variety of stories. The writer has a very human view on gender transition and the cover picture is fascinating. Loved everything in that book.

Looks good

I have bought this book for my 17 year old son who recently told me that he was a transgender and has hidden it until now. This book looks great and I hope he finds comfort with it. I love Transgender people, they are normal just like me and I have a lot of respect for them. This book looks very good. :)

Five Stars

Interesting reading

If you would like to read these original stories, illustrated with breathtaking colour photos and artwork, you can download the original classic FFG Transgender magazines:  http://www.tgfiction.co.uk/

    Jeff didn’t want to do this, it was the last thing he wanted, but after he was evicted from his house he had little choice in the matter. He approached the near mansion of his ex, a slightly bitter and dominant woman named Madeline, of course she knew he had fallen on hard times, she always kept tabs on him and when he was in his hour of need she offered him a job as their home’s cleaner.

    Of course Jeff denied the pity job, not even wanting to see Madeline anymore, let alone work for her, but he was officially homeless now and had nowhere else to go. He waited outside of the mansion for nearly three hours, but eventually he couldn’t wait anymore he approached the front door, slowly knocking three times in a row. He was completely unaware that this was the last time he’d ever see outside of the house again.