Archive-title: Lady Josephine - 1 to 3
I looked around the lingerie department once more. There were a few women
there, mostly middle-aged, and thankfully nobody I recognized. Quickly I
grabbed the bra, panties and suspender belt from their rack and, my heart
beating madly, took them up to the counter.
'Can I help you, sir?' asked the young female sales assistant.
'Yes, I'd like to buy these, please,' I tried to sound as nonchalant as
possible, as if I bought women's underwear every day of the week. 'They're
for my wife,' I added by way of explanation, though of course it was a lie.
She didn't react in any way, but took the lingerie, totalled up the sale,
and took my credit card. I could still hear my heart pounding as I picked
up the plastic shopping bag containing my purchases and made for the
nearest exit from the department store.
About ten feet from the door I felt a tap on my shoulder. 'Excuse me, young
man,' said a woman's voice.
I turned to face her, and recognized her as one of the women who had been
in the lingerie department. 'Are those for you?' she asked, pointing to my
'Well, I, ah, you see...' I blushed and stammered, unable to answer her
'I thought they might be,' she said. 'Perhaps you'd like to come with me.'
And she took me by the arm, and steered me out of the store and onto the
street. She had a determined look on her face that allowed me no argument.
We turned and walked a short distance to her car. She was about the same
height as me, maybe ten or fifteen years older, but her black hair showed
no signs of grey. Her shoes hammered out a staccato beat as she hurried me
along the pavement. She opened the passenger door of her car for me, and I
got in. She quickly got in the other side, and steered out into the
Once we were moving she introduced herself. 'I'm Josephine, Josie for
short,' and she shook my hand.
'Um, nice to meet you Josie,' I said, and told her my name.
'I was pretty sure you would be a cross-dresser,' she said, 'and a lovely
looking one too. Would you like to dress up with me at my place? I've got
plenty of clothes that will fit you, and I could do your face as well.'
It sounded too good to be true. After dressing up on my own for years to
suddenly meet a woman who wanted me to dress up for her! 'Are you also a -'
I began to ask.
'A transvestite?' she finished the question for me. 'Heavens no! I'm all
woman, but the sight of a good-looking young man like you wearing a nice
skirt and blouse and a pair of high-heels, really gets my motor going!' she
laughed, and, nervously, I laughed along with her. The sound of my heart
seemed as loud in my ears as the traffic, and a lot of the blood seemed to
have gone to my groin, because I felt my penis suddenly strain against my
It did not take long to get from the suburban shopping centre to her house.
She showed me in, and took me straight to the bathroom. 'Now first of all
you'll need a shower and a shave,' she said, and she got out a razor and
some towels for me. 'Then you can put on your lingerie. While you do that
I'll get everything else ready for us. Would you like a drink? Good, I'll
pour us a couple of gin and tonics.'
She closed the door before I even had time to think let alone reply. I
jumped in the shower and gave myself a good wash all over. Then I dried
myself and prepared to give my face a shave. While I was running the hot
water into the basin the door opened. 'Don't mind me dear. I just thought
I'd leave you some stockings and shoes for you to put on.' Seemingly
oblivious to my nakedness, she dropped a pair of black high-heels and black
stockings by the door and left again.
I shaved carefully, then opened my shopping bag and took out the red
matching set of bra, panties and suspenders. The fabric looked like a
sheeny satin, and felt as soft as down in my hands. I hurried into them,
fastening the bra and suspenders as quickly as my nervous hands would
allow. The material felt heavenly wrapped snugly around my bust, waist and
hips. I unrolled the black stockings up my legs, feeling the nylon
encompassing my skin, and fastened them to the suspender belt. Then I put
on her shoes. They were on the small side, but I managed to squeeze my feet
into them without too much bother. By this time my cock, which had gone
limp in the hot shower, was straining to get free of the red panties, and
in the mirror I could see a small wet patch on the front of my panties. I
tried to relax for a few minutes, which seemed to work, and forced my cock
down between my legs. Then I unrolled some toilet tissue, and scrunched up
two balls which I put into the cups of my bra. I took another look in the
mirror, then stepped out of the bathroom.
'In here dear,' she called from the next room, and I went in to what was
obviously her bedroom. She hadn't changed from the plain slacks and blouse
that she'd been wearing earlier. However there were a number of blouses and
skirts arrayed on her bed.
'You look lovely dear,' she said, and gave me a quick peck on the cheek.
'It's a pity that you didn't shave your legs though. Well, we can do that
later.' She got me to sit in a chair in front of her dressing table, and
gave me one of the two drinks that were on the table. While we both sipped
our gin and tonics she started putting make-up on my face. She applied a
good deal of foundation all over, and emphasised its importance to me, she
also used some concealer on the darker parts of my beard and blusher on my
cheeks. Then she plucked a few of my stray eyebrows and applied some pencil
lightly. She did my eyes using a black eyeliner, then some eyeshadow and
finally mascara to lengthen the lashes. She was very careful with my lips,
using a pencil to first define them, then red lipstick and a gloss over the
top. By the time she had finished I barely recognized myself in the mirror.
She took a blonde wig and placed it on my head. The long curled hair of the
wig fell to my shoulders and formed a beautiful frame for my new face.
I stood up and, at her suggestion, walked around the room and posed for
her. She got out a camera and started taking photos of me. Encouraged by
her, I began to ham it up a little, pouted my lips, and got into wilder and
wilder poses. By the time she had finished the film, we were both laughing
with abandon. She selected a black silk blouse and a mini-skirt for me, and
while I put them on, she reloaded the camera. The blouse and mini both fit
me beautifully, and before I knew it she was taking shots of me doing up
the buttons of the blouse and pulling up the skirt. I modelled some more
for her, dancing around the room, delighting in the clothes and lingerie
and make-up I was wearing.
She poured another drink for us both. 'Are you enjoying yourself dear?' she
asked. I nodded and sipped my drink. 'Good,' she continued. 'Then perhaps
you'd like to do something for me?'
'Anything,' I replied.
'Well, first I want you to undress me, slowly.'
I put down my drink and walked over to her. I reached out my hand and undid
the top button of her blouse. Then I bent my head forward and gently kissed
the now-exposed flesh on her chest. I also noticed the white lacy bra she
was wearing underneath. I continued unbuttoning her blouse, again kissing
her flesh lightly after each button was undone. My lipstick left red marks
on her skin in a line from above her breasts down to her waist. I undid the
cuffs of her sleeves, and slid the blouse off her arms, kissing all the way
down her arm as the cotton material uncovered first her shoulder, then her
upper arm, shoulder, forearm and wrist. I took hold of her hand and kissed
each of the five fingertips, then kissed her other hand in the same manner.
I knelt in front of her and undid the belt and button of her slacks, then I
unzipped her fly, revealing her lace panties, which matched her bra. As I
pulled the slacks over her hips, I kissed the gentle swell of her tummy,
then lowered my head and kissed the front of her panties. The slacks
dropped on the floor around her feet , and I kissed my way down each of her
She stepped out of the slacks, and kicked her flat shoes off. I kissed the
tops of both her lovely feet and stood up. She turned around, and I
unfastened her bra, then embraced her from behind, pushing my hands inside
the cups of her bra. I began to gently massage her soft breasts, and also
to kiss her bare shoulders, nudging the bra straps off her shoulders and
down her arms so that it fell to the floor. My hands moved down and slipped
inside her panties. While one hand found the slit of her labia and began
slowly rubbing, the other hand gently pushed the panties off her hips and
down her thighs.
She stepped out of the panties and turned around to face me. 'Thank you
Paul,' she said, grabbing my hands which were still stroking her hips. She
let my hands drop and walked over to the bed and sat on the edge, her legs
spread wide apart. 'Now I want you to kneel down on the floor again, that's
right, very good,' as I knelt down in front of her. 'Now bury you head
between my legs and give my cunt a good licking!'
I crawled to her, bent forward so that my face was directly before her
steamy sex. My nostrils filled with the earthy aroma of her, and my tongue
began its work, licking up and down the full length of her red labia. She
lay back on the bed, and draped her legs over my shoulders as I started
licking her clitoris, occasionally squeezing it between my lips. I could
hear her moaning with pleasure, and I redoubled my efforts, dipping my
tongue into her vagina then withdrawing it upwards so it pressed tightly on
her clitoris. Her thighs started squeezing my head, holding it in tight to
her pelvis while her hips began to buck up and down on the bed. My whole
mouth was now pressed closely to her sex and the exquisite taste of her
juices was driving me wild. Harder and harder I drove my tongue deep into
her, then withdrew it, almost lashing her clitoris with each thrust and
return. She screamed as she came, a scream of total pleasure. Her thighs
wrapped even tighter about my head, making my ears ring. I could not
breathe as the tight embrace of her legs was crushing my nose into her mons
venus and my open mouth was still glued to her labia and vagina. It didn't
seem to matter as her orgasm continued and her hips thrust vigorously
against my face.
Eventually the strength of her orgasm subsided, and her legs dropped from
my shoulders and I could breathe. She lay there, panting loudly, pleasure
and satisfaction seeming to come from every pore of her body. I gently
kissed the incredibly soft flesh of her inner thighs while my hands began
stroking between my own legs, rubbing my cock under the satin material of
the panties I had on.
'That was very, very good my dear,' she said softly. 'Now it is time for
you to go.'
I stood up to protest, but she ignored me, and my erection, which had
pushed the material of the mini-skirt out at an unnatural angle.
'Please take off the skirt and blouse, and I do hope there aren't any nasty
stains on them.' Her words were very calm, yet they sounded more like an
order than a request, and I opened my mouth to protest. 'I really think you
should do as I tell you Paul, otherwise I shan't invite you here to dress
up ever again.'
I shut my mouth, anxious to be asked to return, and took off the blonde
wig, mini-skirt, silk blouse and high-heeled shoes. While I hung the blouse
and skirt on clothes hangers, she wrapped a robe around herself and left
the room. When she appeared a few moments later she was carrying my pants,
shirt, shoes and watch.
I dressed in my masculine attire, over the top of my lingerie and
stockings. 'Now Paul, I would like you to return to my house next Saturday
morning at ten o'clock. You should bring with you all the women's lingerie,
stockings, shoes, clothes and accessories you own. If you don't turn up, I
will send complete sets of the photos of you to your boss and workmates.' I
again started to protest.
'Be Quiet!' her voice thundered at me. 'You have willingly placed yourself
within my power. There will be rewards for you, but only if you do not
I quickly considered my position. She could very easily blackmail me, as I
couldn't stand the thought of everyone at work knowing my secret vice and
laughing at me behind my back. And my boss was such a straight, he'd
probably fire me, then where would I be? Also the dressing up with Josie
had been so much fun, it would be great to do it again, even if she had a
few strange quirks.
'Okay then,' I said, 'I'll be here at ten on Saturday.'
'Very good, dear. Now if you'll wait at the front gate, I'll call a taxi
for you. Don't forget to bring everything!'
She closed her front door behind me, and I walked down the path to wait for
the taxi. After a few minutes it showed up, and I got in and rode back to
the shopping centre to pick up my own car. Only when I had got in my car
and looked in the rear vision mirror did I realize that my face was still
fully made up, minus most of the lipstick, which had come off on Josie's
body. While I drove I continued to enjoy the taste that her love juices had
left in my mouth, and my mind was full of thoughts about Saturday.
I rose early on Saturday morning, and had a good long shower followed by a
careful shave. After a quick breakfast, I got all of my female clothes out
from their hiding place in my room. To be honest, there wasn't a lot: a few
bras and panties, two suspender belts and pairs of stockings, one camisole,
one slip and one nightie. Though I loved to slip into lingerie and feel the
soft fabric and lace holding my skin tightly, I hadn't been able to summon
up my courage enough times to buy more. As for buying actual clothes,
shoes, make-up and other accessories, that had always seemed out of the
question to me.
I wondered what I should wear to Josie's house. After a few minutes of
deliberation I decided that she would probably want me to be wearing some
lingerie, so I put on a matching set of black panties and bra, and also
black stockings and suspenders. Over the top of these I put on a good pair
of Levis and a dark shirt, and I draped a sweater over my shoulders. I put
the rest of my lingerie in a bag and headed out. My flatmate Jim was still
snoring as I started my car and backed down the driveway.
I parked outside Josie's house, and killed a few minutes of time listening
to the stereo. When I rang her front door-bell it was exactly ten o'clock.
She opened the door almost immediately. 'I'm so glad you could come dear,'
she said warmly. 'And you've remembered to bring your clothes. There
doesn't appear to be much there, does there? Let's have a look.'
She took the bag from my hand, and spilled its contents over a table. 'Not
a lot,' she commented, 'But your taste isn't too bad. It's a pity you don't
have any clothes or shoes of your own, but I can lend you some for today.'
She led me through to her bedroom. 'I've had those pictures developed,' she
told me. 'Would you like to see them?'
I was unsure what to answer, being curious, yet also aware of her threat of
blackmail. 'Well, I'm not sure . . .' I began.
'Oh don't be so silly!' she said. 'I only threatened you because I wanted
to make sure you'd come back. But now that you're here there's no need for
that at all.'
'Ok then,' I said, glad that she'd cleared the air.
'Good. Would you like to take off your clothes?' She unwound my sweater
from my shoulders and began unbuttoning my shirt. I kicked off my shoes and
pulled down my jeans. In no time all I had on were my black panties, bra,
suspenders and stockings.
She looked at me longingly. 'Oh that's just lovely dear.'
I felt a warm twinge in my groin and glanced down to see my cock pushing
out the front of my panties.
'Please my dear, we'll have none of that today!' she rebuked me, though her
voice was still full of kindness. Chastened, I sat down in front of her
dressing table, and she took an envelope full of photographs from a drawer.
We were soon chuckling away at the photos together. I was again amazed at
how feminine the make-up and wig had made my appearance. Of course the
bulge which often managed to appear at my groin ruined the effect a little,
and we had a few laughs over that. Most of the photographs had turned out
rather well, and Josie complimented me several times on how good I looked
in them. We agreed that she could take more photos of me whenever she
She put the photographs away in her drawer, and then stood behind me.
'Today I think I should take you shopping,' she announced. 'You need to buy
quite a number of things, but we should be able to take care of the basics
in a few hours. You will, of course, be dressed en femme.'
My heart leapt. It seemed all my dreams were coming true. 'Oh thank you
Josie!' I exclaimed, 'That'll be wonderful!'
'I'm so glad you think so my dear,' she replied. 'But before we start I'd
just like you to do something for me.'
'Sure, anything,' I said.
'Good, I want you to get down on your hands and knees and kiss my feet.'
I immediately knelt down before her and lowered my head to her left foot. I
covered her sandal-shod foot with kisses from her ankle to her toes. I even
managed to take some of her toes in my mouth and suck them one at a time.
After a couple of minutes of this she withdrew her foot and replaced it
with the right one. I again worshipped this foot in exactly the same
manner, being very careful that my teeth never touched the pale skin of her
When she was satisfied by my adoration of her feet, she asked me to get up.
As I did so, her eyes caught the sight of my erection, which had now pushed
its way over the waistband of my panties. 'We can't have That showing
today,' she remarked. 'We'll have to get rid of it first.'
She told me to lie face up on her bed and to grasp the headboard of the bed
with both my hands. She warned me not to let go of the corners of the
headboard until she told me to, otherwise our shopping trip would be off.
When I had hold of the corners, she pulled my panties down to my ankles and
asked me to spread my knees as wide apart as possible. Then she picked up
two pairs of panties, wrapped them around my cock, and started masturbating
The panties felt so incredibly soft against my penis and inner thighs, and
her grip was both firm and tender at once. I was already very excited from
wearing my lingerie and viewing her photographs of me and then kissing her
feet, so I was soon moaning in ecstasy with the fantastic hand-job I was
receiving. It didn't take me long to come, groaning with pleasure as semen
spurted from the end of my penis.
She caught most of my come in the panties, and mopped up the rest with a
tissue. She reminded me to keep a hold on the head of the bed as she opened
one of her bedside drawers, and I saw her take out some surgical tape and a
pair of scissors.
She sat on the bed and turned her attention back to my groin. She gently
pushed my testicles up from the scrotal sack into my body, then with two
pieces of the surgical tape taped the sack flat so that the testicles
couldn't drop down. Then with another two pieces of tape she taped my limp
penis under my body. To finish off she used more tape to ensure my penis
stayed in place, including one long strip which ran from my ass, over the
length of my cock, and up almost to my navel. When she had finished she
asked me to let go of the headboard and to pull up my panties.
I stood up, and she admired her work critically for a few moments. Then she
got me to sit down at her dressing table once more and she made-up my face
very similar to how she had made it up on my previous visit to her. When
she had finished with the make-up, she placed the blonde wig over my hair
and inserted a pair of rubber breast forms into the cups of my bra. Then
she attached false fingernails over my own fingernails. The nails were a
light pink colour and went past my fingertips, much longer than my own
nails. She also dabbed a little perfume below my ears and on my wrists.
She got me to stand up, and she inspected her work very closely. Finally
she made a few small adjustments to the wig and touched up my make up in a
couple of places. All the while she was talking to me; teaching me how to
apply the make-up, and also what colours seemed to suit my complexion.
Next she measured me, not only my bust, waist and hips, but also my neck,
arms and legs. She gave me a pair of opaque 70 denier black tights to put
on, which covered up the hair on my legs rather well. Then she gave me a
black camisole and a black slip, a navy blouse and a green skirt to put on.
When I was dressed she again inspected me. The blouse was large and fairly
loose fitting, with long sleeves and cuffs at the wrist. The skirt was also
fairly large, and went half way down my calves.
'I think you should be able to pass,' she said to me, 'At least if nobody
looks too closely at you. You've got tits, long hair and a skirt, which all
look rather feminine. The things which might give you away are your waist
and hands if anyone looks hard, and of course your voice, so you should try
to talk as little as possible. Now my dear, you'll need some accessories,
which will also help you to pass.'
She gave me some dark green suede shoes with low heels. While I squeezed my
feet into the shoes, which were a size or two too small, she found some
jewellery and a handbag and purse for me. I clipped the gold earrings on to
my earlobes, put a couple of rings on my fingers and a couple of bangles on
my left wrist. She also encouraged me to put on a necklace of false pearls,
which nestled nicely above my breasts. She got a brown leather belt and
passed it through the belt-loops of my skirt, then had me hold in my
stomach while she did up the belt as tight as possible. Finally I put some
cash and credit cards into the purse she had given me, then put the purse
plus a make-up compact and a lipstick into the brown leather handbag. I was
ready to go.
Josie got out her camera again, and took a few shots of me from various
angles. Then she touched up her own make-up and we were both ready.
'Now a few thing to remember dear. Your name now is Paula, but you should
try to say as little as possible to anyone. Also, when you walk take small
steps and try not to swing your arms as much as you are used to doing.'
She drove us downtown in her car. On the way she told me about her late
husband. He had been a foreman for a construction company and had died of a
heart attack over two years ago. His life insurance had been pretty good,
and with her part-time accounting job she managed to live fairly well.
She parked the car, and we began our expedition among the shops and malls.
Josie first took me to a cosmetics and perfume shop. There we tried out a
number of perfumes, before agreeing that 'Rive Gauche' and 'Eau
Dynamisante' smelt the best on me. I bought a bottle of each, and then we
went on to the make-up. Josie then insisted that I needed to buy some top
quality cleansers and moisturisers for my skin. After that we selected some
foundation and various colours of eye shadow, eye pencils and liners,
mascara, lipstick and blusher. Josie recommended that we stay we earthy
tones for the present, so we went mainly for browns and subdued reds, along
with some grey. We had a great time experimenting with a lot of the stuff
before we were finished!
Our next stop was a large shoe store. I followed Josie along the racks of
shoes as she picked out some for me to try for size and look. She found
some green suede shoes, very similar to those of hers I was wearing, though
with a slightly higher heel. After trying a few of these on, we found that
size nine fitted me best. Josie then had me try on some bright red pumps,
which were very sexy, and some high-heeled black sandals. What a strange
feeling it was; walking around, perched on the high heels, through a store
filled with women all looking at or buying shoes.
We decided that I would buy the three pairs I had tried, and then Josie
spotted a pair of black heels with ankle straps. She made me try them on,
even though they were only in size eight. As I walked about in them she
encouraged me: 'Oh darling, they're just so sexy! They make your feet look
good enough to eat!' With that I was sold, so we added them to the other
three pairs. After I had paid for the shoes I changed Josie's green shoes
for the similar pair I had just purchased, which felt a lot more
comfortable, being a size and a half larger.
We walked back to Josie's car and left the shoes and cosmetics I had bought
there. Then we went to a cafe and had some lunch and a coffee. while we
were eating Josie complimented me on how well I had done that morning. She
had only seen a couple of people who had stared at me, usually when I had
said something, and sounded like a bad imitation of Marlene Dietrich. Of
course the lovely assistant who had helped us in the cosmetics shop had
known almost straight away that I was a man, but Josie told me that she
knew that lots of the TV's in town used that shop, which is why she hadn't
reacted to me at all.
After finishing our coffee we went to a lingerie shop. It felt like to
heaven to be able to walk amongst the racks of beautiful under-garments
without feeling like some kind of alien or freak. Josie quickly selected a
dozen or so pairs of panties and french knickers in various styles and
colours, and I found some bras and camisoles to match. We also got two more
suspender belts, and four slips and half-slips. Josie then took me to the
back of the store, where they had the foundation garments and corsetry. She
picked out two pairs of control panel briefs, a torsolette, a waist
cincher, a long legged panty girdle and a corselet.
The saleswoman who was assisting us was very happy at all the lingerie we
were buying, and was busy folding and packing it all. She suggested that we
might be interested in some nightwear, and pointed us in the right
direction. They certainly had some lovely clothes for wearing in bed: I was
straight away attracted to a beautiful white peignoir set with a long
negligee which had lace across the bust and for the shoulder straps, then
yards of soft satin flowing from under the bust to the floor, the gown that
went over the negligee was mostly in a sheer transparent net which reached
down to my knees and was trimmed with white lace. Josie found a pink silk
teddy with lace trimming the legs and down the front, which we both thought
was beautiful. We also got a black nightdress in a translucent satiny
material, with two swirls embroidered on the front in gold thread.
The total bill at the lingerie shop was over a thousand dollars, which,
along with the money I'd already spent on shoes and cosmetics, put me way
over my monthly budget. I asked Josie if we could stop shopping now and
take everything home. 'Heavens my dear!' she replied, 'You still need to
get some clothes and accessories.' But seeing how worried I was about
spending money I didn't have she relented a little, 'Alright then, I'll let
you use some of my jewellery, but you have to get a shoulder bag and a few
clothes. Let's just go to a department store and get a few things.'
We left all the shopping bags full of lingerie in her car, then headed for
the nearest department store. Women's bags and accessories were close to
the door we went in, so we went there first. Josie quickly found a brown
leather bag, and persuaded me to get a matching purse. Then we went up two
floors to Ladies' fashion. The range of clothing there was quite
bewildering, and I had little idea of where to go. However Josie guided me
to the separates section and began picking out blouses and skirts for me.
When she had taken enough clothes we went into one of the changing rooms. I
pulled the curtain across the front of the small partition and took of my
shoes and skirt and blouse while she hung up the clothing. Suddenly she put
her arms around me and kissed me full on the lips. Her tongue pushed
against my lips, parting them, and she thrust it into my mouth. I
responded, and met her tongue with my own, while I put one arm around her
waist and began massaging her breasts with my other hand.
She ended the kiss. 'Darling, let's give the folks behind the security
cameras something to watch!' she whispered in my ear. She kissed me again,
thrusting her tongue deeper and deeper into my mouth, seeming to eat the
essence right out of my soul. One of her hands lifted the hem of my slip,
and she began to rub and squeeze my stockinged thighs. I continued
massaging her breasts, undoing the top buttons of her blouse and slipping
my hand inside. She was now running one of her fingers under my panties,
along my taped down penis, and I let out a low moan of pleasure.
She removed her hand from under my slip, and lasciviously sucked her middle
finger. Then I kissed her again, while her hand found its way back inside
my panties. This time she started fingering my ass, and soon her moistened
finger was probing my hole, gently moving in and out in rhythm with our
tongues which were again entwined between our mouths. I moaned once more as
her finger sunk in as far as it could go and was withdrawn. She brought her
hand up to my face, and I licked and sucked her finger clean. We then
kissed once more before turning our attention back to the clothes I was
supposed to be trying on.
After almost an hour we finally left the department store with the seed of
my new wardrobe: a navy jacket with matching knee length skirt, a short
black dress, pink, mustard and white blouses, a grey skirt which came to
just above my knees, and a longer, fuller tan skirt.
When we arrived back at Josie's house, we left all the shopping in the car
and hurried inside, as Josie said she had a surprise for me. She took me to
her bedroom and told me to take off my blouse, skirt and shoes while she
looked for something in her wardrobe. She tossed me a white half-slip to
put on, and then got me to step into a long sleeved black dress. The
sleeves had white lace cuffs, and the high collar of the dress was also
white lace. Josie zipped up the dress, which fitted me rather well. Then
she tied a white frilly apron tightly around my waist and put a white cap
on my head.
'There now,' she said. 'You're properly dressed to be my maid. What do you
I replied that the dress was lovely, but I didn't know what she expected of me.
'You will spend the remainder of this afternoon and this evening as my
maid, doing what I tell you to. You will address me as "Lady Josephine", is
'Yes,' I replied.
'Yes, what!' she demanded.
'Yes Lady Josephine.'
'Good. Now sit down and touch up your make-up while I go and get your shoes.'
She went out to the car and brought back the pair of black high-heels with
ankle straps I had bought that morning. Meanwhile I reapplied some lipstick
and a touch of powder to my face. Then I slipped on the black shoes, did up
the straps and stood up.
'Right,' she said, 'Now first of all I want you to make me a drink, I think
a gin and tonic will do. Serve it in the lounge.'
I tottered out of the bedroom and down to her kitchen. I quickly mixed the
drink for her and took it through to the lounge. She was sitting on a sofa
'You idiot!' she screamed at me as I put the glass down on the table.
'Don't you know to put a slice of lemon in a gin and tonic, or to use a
'I'm sorry Lady Josephine,' I said.
'You will be,' she replied. 'Now I want you to bend over for me and touch
I bent forward, and she picked up a leather strap and began hitting my
backside. I yelped with surprise, and straightened up, moving my hands to
protect myself, however she continued laying into me, whacking my hands and
arms as well as my buttocks and legs.
'Stay still, or I'll tie you up so you can't move,' she threatened. I bent
forward again and touched my toes, while she delivered ten stinging blows
to my rear.
'Let that be your first lesson as my maid Paula. You will stand still and
accept any punishment I may give you, otherwise the punishment will be
doubled. Now turn around and thank me for teaching you.'
I turned around. 'Thank you Lady Josephine,' I mumbled, my bottom hurting
like hell and feeling like a little boy.
'I didn't hear you. Speak clearly!'
'Thank you Lady Josephine,' I repeated, this time louder and more clearly.
'That's better, dear. Now go and put some lemon and some more ice in my
drink, and don't forget the coaster. And one more thing, you will have to
curtsy to me whenever you come before me or are about to leave. Can you do
I bowed down deep before her, putting my right leg behind my left and
spreading my arms while holding the hem of my dress. 'Very good, dear,' she
said. 'Now go and fix up my drink.'
I picked up the glasss and returned to the kitchen. In a few moments I was
back having put a slice of lemon and some more ice in the drink and holding
a coaster. I placed the drink before her, and again curtsied low. She took
a sip of the drink and looked satisfied.
'Now what I want you to do is some cleaning.' She handed me a feather
duster. 'You can dust and then vacuum throughout the house. You will find
the vacuum cleaner in the hall closet. Make sure you do a good job.'
Once more I curtsied in front of her, then picked up the duster and went to
start on the chores she had given me.
It took me nearly two hours to go all through her house dusting and
vacuuming. As soon as I finished a room she would carefully inspect it, and
usually would find some spot of dust or litter that I had failed to notice.
Then I would have to redo the entire room. By the time I had finished and
put away the vacuum cleaner and handed her back the duster, I was quite
'You have done a good job of the cleaning Paula,' she said. 'But you look a
little tired. Would you like to rest for a while?'
'Yes, thank you, Lady Josephine,' I replied, and I gave her another curtsy.
She led me to her bedroom and invited me to rest on her bed and to pay no
mind to what she was doing. I took off my high-heels and lay down on the
bed, quickly shutting my eyes and starting to doze off.
A few moments later I felt something at my ankles, and looking down I saw
that they were tied together with a cord which was then tied to the foot of
the bed. Lady Josephine was standing by the bed, and I gazed up at her,
catching the delighted look in her eyes.
'You look so beautiful lying there,' she said. 'I would like you to perform
another service for me.'
I nodded my agreement, and she removed her skirt and panties. She knelt on
the bed, and I could sense the warm smell of her sex. She put her knees
either side of my face, then lowered her body until she was sitting on me,
her buttocks on my chest and her vulva directly in front of my face. 'I
want you to eat me again Paula,' she commanded, and moved forward so that
her sex was covering my mouth.
How I loved the feel of her weight bearing down on me while I pushed my
tongue between her moist labia! As if in a dream I inhaled her strong musk
and, exhilarated, pushed my tongue deeply into her. Her juices tasted
heavenly as I ran my tongue over her clitoris time and time again, and she
groaned deeply. I alternated my tongue between thrusting deeply into her
vagina and licking her clitoris, while my lips were able to do service all
around her vulva.
The effect on Lady Josephine was dramatic. Within a few short minutes her
knees and thighs gripped the sides of my head tightly, squashing my ears to
pulp, as she began to come. Again and again she ground her pelvis down into
my face, all the while moaning and groaning with sheer delight.
After her orgasm, she rested, still sitting on my face, panting. I felt
powerless to move her, despite the fact that my jaw ached terribly and I
was finding it hard to breathe. Soon she shifted, but to my disappointment,
she only moved slightly forward, which completely blocked my nose.
'Now I want you to tongue my ass Paula,' she said, and planted her hole
right on my mouth. I began to lick all around her anus, tasting both the
juice that had run there earlier, and also the earthy taste of her behind.
Gradually I pushed my tongue further and further into her tight ass, and as
I did so she groaned again, and began to slowly rub her vulva on my top lip
and nose. The strong almost fungal taste started to overwhelm me as my
tongue made its way fully inside her, and at the same time the sweet smell
of her vagina was overloading my nasal passages. Before long she reached
her second climax; the combination of my tongue up her ass and her clitoris
rubbing on my face proving irresistible. Once more her thighs strongly
gripped the sides of my head, and her sphincter muscle contracted in a
sudden spasm, ejecting my tongue from her hole.
She rested her entire body weight on my face while she regained her
composure. Finally she rose and put her skirt and panties back on. 'Thank
you Paula,' she said, untying my feet, 'What a good little tongue you have.
I'm sure I'm going to get lots of use from it. Now come down to the kitchen
and prepare dinner for me.'
I followed her to the kitchen, where she gave me directions as to the meal
I was to cook for her. I poached a trout with white wine and herbs and
prepared some vegetables; steamed broccoli and baby carrots, and baby
potatoes. I also prepared a light salad and defrosted a frozen cheesecake
When the food was almost ready, I set the table in the dining room for her
and lit the candles on the table. All the while Lady Josephine had been
having a relaxing bath. When she returned for her dinner she had changed
into a long black evening dress with a very deep cleavage and black sandals
with high heels. She had also pinned up her hair and fully made up her
face. She looked gorgeous.
I pulled out her chair for her, and pushed it in again as she sat down.
Then I poured her a glass of wine, and returned to the kitchen so I could
bring her the food. When I had served her the trout and vegetables, she
asked me to stand to attention in the corner of the dining room in case she
needed anything else. After she had eaten as much of her dinner as she
wanted, I took away the dishes and cutlery and washed them while she
enjoyed another glass of wine.
When I had finished washing up and putting everything away, she appeared at
the kitchen door. 'Thank you for dinner Paula,' she said, and kissed me
gently on the mouth. I tried to embrace her, but she gently pushed me away.
'You have been a good maid today, however it is time for you to go home. Go
down to the bathroom and change into your jeans and shirt, then I'll drive
you home.' I curtsied, then went and got changed.
In the bathroom I took off my maid's dress and hung it on a clothes hanger.
I also removed my cap and wig, and took off my make-up. Then I put on the
Levis, shirt and sweater I had been wearing when I arrived, many hours
She drove me home, and on the way invited me to visit her again in the
morning. I realized that I had left my car outside her place, and so I
would have to return in order to pick it up.
When we arrived at my place we took inside the many shopping bags full of
clothes and other gear that I had bought that day. In my room we unpacked
everything and put them all away in my closet or drawers. When we had
finished, Josephine took all my underwear and pyjamas out of their drawer,
and stuffed them into a couple of shopping bags.
'From now on you may not wear underpants, or shorts, or pyjamas,' she told
me. 'Instead you will wear a pair of fresh clean panties every day and a
nightie when you go to bed. Is that understood?'
'Yes, Lady Josephine,' I replied.
'Good. Then I'll see you tomorrow at ten. Bring along some of your new
clothes and shoes.'
After I had shown her to her car, I went back to my room in order to
release my cock and balls from the strong tape that had held them in
position for twelve hours. After a few excruciating minutes my private
parts were free, though at the cost of what appeared to be a large
proportion of my pubic hair. I then dashed for the toilet and gratefully
Once back in my room, I stripped, ready for bed. From my new collection of
nightwear I chose the white satin negligee. As soon as I put it on the
dreamy soft material sent me into seventh heaven. I collapsed on the bed,
my cock hard under the clinging material, panting with excitement. I stuck
a pillow up beneath my negligee and over my cock, then I rolled onto my
stomach and masturbated against the pillow. With the satin material
caressing my buttocks and legs it was all I could do to stop my self
screaming with joy as I came.