Story: The New Maid

By Emily Ross
emily_ross_98@yahoo.com

Part One - Vicky's Story

I hadn't seen my sister in three years while I had been working in Australia. 
Now here I was knocking on her front door. A maid answered. 'Miss 
Simmons? Come in. Let me take your suitcase. Would you like to go into the 
drawing room? I'll tell Mrs Hardy that you are here.'

'Thank you.' I went into the drawing room and sat down. A minute or so 
later my sister came in. I jumped up and gave her a hug. We kissed each 
other on the cheeks.

'It's been such a long time since I saw you, Vicky. I've got so much to tell 
you. How was the journey?' Liz asked.

'Fine.'

'And now you're coming back here to live. And getting married too. Oh 
we've got so much gossip to catch up on. Please sit down.'

We both sat down and there was a gentle tap on the door. It opened and the 
maid appeared. 'Excuse me, madam, would you like tea?'

'Yes please, Caroline.'

Caroline left and closed the door silently behind her.

'Is she new here?' I asked Liz.

'Caroline?'

'Yes.'

'Sort of new.' 

I looked puzzled. 'Uh?'

She smiled. 'That was Paul.'

'Paul? Your husband?'

Liz smiled. 'Yes, isn't he a doll?'

'But why?'

'I'll explain later. He'll be back in a minute with the tea. I don't want him to 
overhear us talking about him. Tell me about your fiance.'

'His name is Gavin Holden. He's twenty five and he's a journalist. He's 
been working for a big publishing house. Writes for lots of different 
magazines. I've known him for about three years but we only started seeing 
each other seriously last year. Two months ago he got this job here with the 
Enquirer as Assistant Editor. Then he popped the question. 

'Did he get down on bended knee?' 

I ignored her. 'He starts there next month. I've come here ahead of him to 
find us a flat - somewhere to live while we settle in. I've also got to find a 
new job.'

'Yes.' There was a gentle knock at the door and the maid re-appeared 
carrying a tray with teapot, jug, cups, saucers and a plate of biscuits. Was 
this really Liz's husband Paul? I was fascinated as he glided across the room 
and carefully bending his knees put the tray down on the coffee table.

'Shall I pour, madam?' he asked.

'Yes, please, Caroline.'

Caroline picked up the teapot and started to pour the tea. I watched 
transfixed, hoping Liz wouldn't think I was staring. 'Sugar, Miss 
Simmons?' Caroline asked.

'No, thank you.' I was concentrating so much on Caroline's appearance that 
I could hardly get the words out. His feminine, made-up face was quite pretty 
yet I could just recognise Paul's features. His dark hair was formed into a 
short bob. He wore a short black maid's dress with white lace trimmings 
over a white underskirt, that was slightly longer than the dress and flared out 
to give it shape. The maid's uniform was completed by a white apron and a 
lacy white cap. Black nylons covered his shapely long legs finishing in a pair 
of high heeled black shoes. A well manicured hand passed me a cup and 
saucer. If Liz hadn't told me, I would never have guessed that the pretty 
creature now handing her a cup of tea was a man.

'Anything else, madam?'

'No, thank you, Caroline.' The maid curtseyed and left the room. Liz burst 
out laughing.

'Wow,' I said, 'How did you turn your hulk of a husband into a sissy?'

'Six months ago, Paul got made redundant. I'm on a good wage from the 
computer consultancy firm but I told him that as we only had one wage 
coming in we wouldn't be able to afford to keep our old maid, Fiona. You 
remember her, don't you?' 

I nodded.

'Paul asked me who would keep the house tidy, make the bed, dust and 
Hoover. I said that he would have to do it until he got another job as he 
would be home all day. I told him that as I was the breadwinner I was in 
charge and he would have to be the new maid. He asked me if he would have 
to wear the maid's uniform. 

'An old colleague had told me some time ago how she had feminised her 
husband, making him act much more maturely and responsibly and how no 
man could be unfaithful wearing a skirt. So I said yes, he would have to 
dress the part.

'He didn't argue at all but went upstairs, found Fiona's uniform - it was her 
day off - and put it on. He's worn it practically every day since.'

'Does he always call you madam?'

'Oh yes, that's part of our agreement. Between eleven in the morning and 
seven at night he has to act as my maid. He must call me madam and curtsey 
or I will punish him.' I wondered what form this punishment took but didn't 
dare ask. 'When he is off duty, he can dress as he pleases and calls me Liz.''

'Does he dress as Paul or Caroline when off duty?' I asked curious.

'At first, after he'd finished his daily duties he used to dress as Paul, but now 
his hair and finger-nails are much longer, he is always Caroline. I think he 
likes it better that way. And I do too.' She smiled. 'Of course, he's stopped 
looking for a new job, I think he likes this one more.'

'Isn't it humiliating for him, dressing like that and being servile?'

'Nonsense. He loves it. Remember he first suggested it and I'm sure he likes 
dressing like that. He's never complained. Within a week of becoming 
Caroline, he'd taken up the hem on his uniform. It used to come down to 
Fiona's calves. Not on Caroline. He loves short skirts and dresses. This 
arrangement suits us both. He can dress to fulfil his fantasies and I get all the 
jobs done around the house.'

'Is he a good maid?'

'Excellent. Meticulous in what he does. But then he knows he'll be punished 
if his standards fall below the highest.' Again I was curious about the 
punishments but didn't dare ask.

'And what about sex?' I asked. 'He is still your husband. Do you still sleep 
together?'

'Of course, why not? He may wear lacy lingerie in bed but underneath he is a 
hundred per cent man. In fact our sex life is better than ever. Caroline has his 
own bedroom where she keeps his clothes but he nearly always sleeps in my 
bed.'

There was a polite knock at the door again and Caroline came in to collect the 
tea cups. Once more he curtsied and then bent down carefully to remain 
decent as he picked up the tray.

'I can't get over how feminine he is,' I remarked when he had gone. 'And 
pretty.'

'I know, but we had to work hard to get the right effect. I had to teach him 
about deportment, how to sit, do make-up, wear heels, everything about 
being a woman.'

'Well. It's certainly paid off. He's beautiful.'

'Why, thank you,' said my sister modestly. 'And soon you'll find out what a 
good cook he is.'

He was a good cook too, preparing a lovely meal ready on the dot of six 
o'clock and acting as waitress for Liz and me. Liz explained that she always 
ate at six to give Caroline time to clear away and wash up before going off 
duty.

'Caroline,' Liz said, during the meal, 'I've got to go out this evening to visit 
a client at seven o'clock. I don't know when I'll be back but while I'm out, I 
want you to look after Miss Simmons and tend to her every need.'

Caroline curtsied. 'Yes, madam.' 

After the meal Liz got changed and slipped out about ten to seven. I was in 
the living room reading a magazine and I heard Caroline's high heels clicking 
up the stairs about seven. I found the magazine very interesting and soon 
completely forgot about Caroline, who must have been upstairs nearly an 
hour. Then the door opened and he came in.

I caught my breath as in the doorway I glimpsed the most beautiful woman 
I'd ever seen - my brother-in-law. Gone was the servile attitude of no eye-
contact and no smile. Here was a confident, attractive, out-going young 
woman, who walked over towards me. His eyes sparkled, his hair shone. 
Liz was right - he did enjoy it and no wonder.

He wore a black stretchy mini-skirt that barely covered his bottom and a short 
top that just reached his waist, revealing a flash of flesh as he walked and the 
twinkle of a pierced belly button. Dangling from his wrists were several 
bracelets and around his neck a beautiful necklace. His make-up was less 
subdued and more accentuated than before but classy. There was a whiff of 
expensive perfume. 

On his legs he wore flesh coloured tights - they couldn't have been stockings 
with that skirt, an ankle bracelet and some very high heels on his feet. Had 
there been any man present (other than my brother-in-law, of course) they 
could not have been anything other than strongly attracted to this vision. 
Everything about him, his appearance, his mannerisms, his movements and 
his voice were feminine.

He was stunning. I've always thought of myself as totally heterosexual but 
here was the exception that proved the rule. I was aroused by Caroline's 
beauty and found him very attractive, particularly when I thought about what 
was hidden underneath that tiny skirt.

'How do I look?' he asked as he sat down next to me on the sofa.

'Fine,' I said. I felt distinctly in his shadow. He was better than fine. He was 
perfect.

'I know what you're thinking,' Caroline said. 'How can I put up with the 
humiliation; dressing as a maid, doing the cleaning and ironing, calling my 
wife madam, curtseying to her and answering to her every whim?'

'I had wondered,' I said.

'It is humiliating, but it's part of the fun,' he went on, 'I don't know why I 
like it but the repression of being a maid makes the freedom of dressing like 
this all the more enjoyable. Look at me now. Tell me, do you find me 
attractive?'

I confessed that I did.

'As a man or a woman.'

'I don't know. I only know that I want to kiss you,' I said. Our mouths met 
in a lingering kiss. I put my hand automatically on his uncovered nyloned 
thigh. He lifted the hem of my knee length skirt and started stroking my 
thighs, quickly progressing to the bare flesh above my stockings. I had 
started wearing suspenders and stockings at Gavin's insistence recently - 
something I might regret with the return to the English climate - and I hoped 
that Caroline did not think that I was too much of a slut. 

But I was past caring. Caroline was feeling me between my legs and I had 
lifted his skirt - not that I had to lift it much. I felt down his tights and had 
found the tapes that held his penis in place between his legs. I loosened the 
tapes and his manhood burst free, erect and hard. I had to have him inside my 
body.

The kiss ended and we stared into each other's eyes. He was so pretty. I 
moved so that I was kneeling across him on the sofa. I pulled my loose silk 
panties to one side and forced his penis into me. We started kissing again. 

Now I enjoyed sex with Gavin, but the pleasure now was like the pleasure 
with Gavin to the power eight. He was so hard, so big. 

What was I doing? I was fucking my sister's husband. She might come back 
at any minute and find us. Only an hour or so ago she told me no man could 
be unfaithful wearing a skirt and here was her husband being unfaithful with 
me in the shortest skirt I'd ever seen. 

The fear of being caught made it all the more exciting. It did occur to me that 
perhaps Liz had deliberately left me here alone with Caroline so that I could 
learn the benefits of a sissy-husband. And what benefits? I was in ecstasy 
and suddenly I was coming and so was Caroline writhing deep inside me, 
coming, coming, coming. 

This was the best orgasm I had ever had. I knew then that I had to turn my 
future husband into a sissy-maid, too.

'That was fantastic,' I said, 'I can see now why Liz likes you dressed up like 
that. Do you think my fiance would like to dress like that too?' I asked him 
when we had got our breath back.

'Of course, most men are sissies at heart. I bet your fiance is the same. The 
hard part is to get them into women's clothes in the first place. Then they find 
out how good it is.'

'Could you help me do it to Gavin?'

'I'll try. Now we had better get ourselves tidied up before Liz gets home.'

I stood up and adjusted my stockings. Caroline pulled up his panties and 
tights and taking a mirror and lipstick from his handbag soon had his make-
up as good as new. I checked mine was OK. "Not a word about this to your 
mistress."

"No."

We talked about how I should go about finding somewhere to live. Of 
course, Liz didn't get back till quite late. If she had meant to give us the 
opportunity she was giving us plenty of time.

The next morning, the maid woke me with a cup of tea and a curtsey around 
nine o'clock. Funny, I thought, Liz said she didn't start work till eleven.

'Mrs Hardy said I should wake you up at nine. She's left for work an hour 
ago, but she said I had to get you up so you could go flat-hunting.' She 
handed me the tea.. 'Mrs Hardy said I was to give you any help you needed.'

'Thank you,' I said. 'You can be my flat-hunting guide.' He looked so 
pretty. I couldn't resist. 'Caroline, I love a man in uniform, would you like to 
get into bed with me?'

'Oh no, madam,' he replied. 'I've got to clear up the breakfast, make the 
beds and do all the cleaning, before we go out. There won't be time.'

'Nonsense, we can make time,' I replied and then as an experiment I said, 
'Caroline, I order you to get into bed with me.'

Caroline was always obedient and today was no exception. He kicked off his 
high heeled shoes and slipped in next to me under the duvet. 'Yes, madam,' 
he said demurely.

We were soon hugging. He was putting his hands up my nightie and I was 
feeling up his dress. He was wearing stockings and no panties. Was he 
expecting this? Once more the sex was better than ever and the orgasm 
wonderful.

'Oh, Caroline,' I said as we cuddled and recovered our breath. 'Promise me 
that you'll help me turn my fiancee into a sissy maid.'

'Yes, madam.'

We found a lovely flat about a mile away from my sister's house and I paid a 
deposit on the spot. I couldn't wait to move in with Gavin. That evening 
when Caroline was clearing away the dinner I said to my sister, 'Liz, I've 
been so impressed by Caroline, that I'd like to turn my Gavin into a sissy. 
Will you help me?'  I couldn't tell her the real reason, of course, although I 
still wonder if she suspected or even knew.

Liz gave me a hug. 'Yes, yes, yes. I hoped you'd feel like this. I just never 
guessed it would happen so quickly. Now let's draw up a plan.'

Part Two - Gavin's Story

About a month after I had started working for the Enquirer, Vicky's sister Liz 
invited us to her place for Sunday lunch.  Vicky had started work with the 
same computer consultancy firm as her sister, who had evidently put in a 
good word for her.

Although I had met Vicky before, this was the first time I had been to her 
house. I was impressed by its size. We parked on the drive and a maid 
answered the door. They must earn a lot of money,  I thought to myself. 
Either Liz is on a big salary or her husband, Paul, is rolling in it.

There was no sign of Paul. We had lunch, cooked and served by the maid 
who was very attractive in a short black uniform dress and high heels. The 
three of us were just enjoying a cup of coffee when the phone rang. The maid 
answered it and handed the phone to Liz who spoke for a few minutes.

'Shit,' she said when she put the phone down, 'the system has crashed at 
Helium Metals.'

I had heard a bit about this system from Vicky. It was a huge contract that she 
had had a small involvement in.

'What have you got to do?' asked my fiancee.

'I've got to go and try to get it started again.'

'Now?'

'Yes. It's got to be working for tomorrow morning.'

'Could I help?' Vicky offered.

'Well, thank you, Vicky,' Liz replied, 'it would be good to have some moral 
support and someone I could discuss recovery strategies with. Are you sure 
you won't mind? What about Gavin?'

'Oh, I don't mind,' I said, 'I'm sure I could find a few things to do here until 
you get back.' I already had one idea.

So Liz and Vicky said goodbye, leaving in my car. Liz and I had both 
consumed a lot of wine over lunch so Liz had to drive. As she left Liz told 
her maid, Caroline, to do anything to please me as they would be some time. 
That idea was beginning to develop.

I settled down in the living room watching a video. After half an hour 
Caroline who had by now cleared away and washed up the lunch came in. 

'Can I get you anything, Mr Holden?' she asked.

'Why not come and sit next to me on the sofa?'

Sitting obediently next to me, Caroline's dress rode up revealing a bewitching 
stocking top and suspender. This is my lucky day, I thought to myself.

'Hold my hand,' I said. Caroline took one of my hands in beautifully 
manicured fingers. I put my other arm around the maid's shoulders.

'Kiss me,' I said and our lips and tongues met in a delicious long French 
kiss. I was in heaven. My penis was fully aroused and I felt Caroline's firm 
breasts through the material of the maid's dress.

Caroline undid my flies and was feeling my manhood. I reciprocated by 
putting my hand up Caroline's little dress, feeling stocking tops, suspenders, 
bare thighs and between the maid's legs was...

'Oh my god,' I jumped up from the sofa. 'You're a man.'

'Yes,' said Caroline calmly, 'I thought you knew.'

'How could I know? You're so ... so ..."

'Feminine?'

'Yes and attractive.'

'Well don't get upset,' Caroline urged.

'But I've been kissing and feeling a man.'

'Sit down,' said Caroline, 'calm down and I'll tell you what we're going to 
do next.'

I sat down and took a few deep breaths. 'You've been very naughty, Mr 
Holden,' he said, 'so I've got to punish you. You've been kissing a man. 
The punishment is to dress as a maid for one hour.'

'What like you?'

'Exactly like me,' he said.

'But I don't want to.'

'But you've got to. You wouldn't want me to tell your fiancee that you've 
been kissing me and feeling up my dress. That her beloved was being 
unfaithful with a sissy. She'd call the wedding off. Don't worry it will soon 
be over.'

'What if Liz and Vicky come back.'

'They won't. The system's crashed. They'll be gone for hours.'

There was nothing for it. Caroline told me to have a shower and shave my 
face and body. When I came out of the shower, he was waiting for me with 
panties, a corset, a bra and black stockings. He helped me put them on and 
stuff some padding down my bra. I could hardly breathe in the corset. He sat 
me down in his bedroom and painted my face. It seemed to take hours but it 
was probably only ten minutes. Then he put a shoulder length black wig on 
my head.

He undid his apron and put it on the bed. Then he took off his maid's dress 
and handed it to me. I put it on followed by the apron, the cap and his high 
heels which he passed to me. I looked at myself in the mirror. I looked quite 
feminine. I was slightly ashamed to discover that the sight of myself in a 
dress had made my penis go hard again. Fortunately I don't think Caroline 
noticed this as the dress flared out so much.

'I shall call you Sophie, OK?'

'Yes, Caroline.'

'You must call me Miss Hardy, if you please. You are my servant for the 
next hour and you must help me get dressed. Caroline was standing in his 
underwear. I found him a clean pair of tights, a tiny black mini-skirt and a 
crop top, in which he looked very glamorous. His belly button was pierced. I 
had to spend five minutes just brushing his hair. He was very pretty. I 
wondered if I could ever be as pretty.

We went downstairs. I would be lying if I said that I didn't enjoy the swish 
of the dress as I walked, although walking in those shoes was not easy.

I was watching the clock like a hawk. Half hoping the hour would soon be 
up in case Liz and Vicky came back and saw me in the maid's costume, half 
hoping the time would pass slowly as I was beginning to enjoy the sensation 
of wearing a dress.

The hour was nearly up when my worst nightmare came true. A car drew up 
on the drive and there was a ring at the bell.

'Oh my God,' I exclaimed. 'I'd better go and change.' I started to move 
towards the stairs.

'No,' said Caroline. 'You're the maid, Sophie, maids answer the door. I 
can't answer the door dressed like this. It's beneath my station. So very 
slowly, humiliated, I made my way to the front door and opened it.

'Good afternoon, Miss Simmons, good afternoon Mrs Hardy,' I said, 'come 
in. Let me take your coats.' I was the maid after all.

Caroline appeared in the hall. 'Let me introduce Sophie, the new maid,' he 
said. 'Sophie liked what I was wearing so much, that he badgered me into 
letting him try it on. In the end I gave in and said that he could for an hour. 
The hour's nearly up but isn't he pretty?'

'Yes, I am sure that with training he could be as good a maid as Caroline,' 
my fiancee said, 'but he must learn to curtsey.'

I smiled an embarrassed smile and curtsied. I took the coats and put them 
away in the cupboard, while Caroline, Liz and Vicky went into the living 
room. When I went in to join them the hour was up. I was about to say that I 
would go back upstairs and change when Liz said, 'Sophie, I've persuaded 
Caroline to let you wear his dress for the rest of the day. Now go and make 
us a cup of tea. We're exhausted.'

I gasped but secretly I was glad that I didn't have to change. That evening it 
wasn't Gavin who went home with Vicky, but her new maid, Sophie. It was 
the start of a beautiful relationship - Caroline has trained Sophie in all aspects 
of service. 

Every day after work at the newspaper, I go home and change into the maid's 
costume and become Sophie. Vicky says that soon I'll be a good enough 
maid to have my belly button pierced. She thinks our sex life has improved 
100 per cent since I became her maid and I can't disagree. I reckon most men 
would be happy with that. 

Sophie loves to go shopping at weekends with Vicky. Sometimes Liz and 
Caroline come along to make up a foursome. Now we're planning our 
wedding. We still can't decide whether I should walk down the aisle in 
white. 

 - end -