Retirement Plan
As I sat at the dressing table brushing my hair I noticed my wife
looking at me oddly. She was sat on the edge of our bed, ready to go
out for dinner.
"What?" I asked, turning round to look at her.
"Nothing really, darling," she replied. "It's just that in all my
thoughts about married life I never once thought I'd be watching my
husband sat at a dressing table getting ready to go out wearing such
beautiful underwear," she finished with a smile.
I paused with the brush midway through my shoulder length hair and
looked down at myself. At the end of my smooth, hairless legs, I could
see my toenails painted a deep crimson through the sheer stockings I
was wearing, stockings I knew were held in place by a beautiful deep
boned lace and satin suspender belt. I knew the clips for the
suspender belt were slipped under the matching panties I was wearing,
the set finished off by a matching underwired and padded bra which
supported my false breasts. All this was covered with a matching slip
which barely reached the stocking tops as I was sitting down.
Comparing the image I saw with the term 'husband' was something I
struggled to resolve and my wife clearly saw the struggle in my eyes
as she got off the bed and padded over to me in her own stocking clad
feet. Kneeling in front of me she took my manicured hands in hers and
looked me in the eye.
"Don't worry yourself, my dear. I'm not cross or upset, this was my
decision after all. It's just that sometimes I reflect on how unusual
our situation is."
She kissed me on the lips and added, "Now finish getting yourself
ready or we will be late," and got up and left me.
I turned back to the mirror and looked at myself through my mascara
laden eyelashes. There was no real trace of the husband who had walked
down the aisle with her all those years ago. My hair framed a face
that had responded well to the beard removal treatment and was now
made up with eye liner, eye shadow and blusher, quite heavy but ideal
for a night out. I had become quite adept at applying my own make up
and was confident that it looked good. Reaching out I picked up the
lipstick I had set aside earlier, removed the top, twisted the tube
and applied a good coat of the deep colour which seemed to lift my
lips. Finally I picked up the earrings which matched the necklace
hanging round my neck and nestling in my 'cleavage'. Standing up, I
looked at myself in the full-length mirror. The image staring back at
me screamed feminine. Reaching to the wardrobe I took the dress I was
to wear off its hanger and stepped into it. Pulling it up my body
which had changed shape due to all the hormones, I slipped my hairless
arms through the cap sleeves and did up the zip at the side of the
dress. It fitted perfectly, showing curves in just the right places.
As I did a little twirl, my wife walked back in the room.
"You look perfect, my dear," she said, "now get your hand bag, shoes
and jacket as we really must go, the taxi is outside."
Following her instructions, I slipped on the two inch heels and
jacket, picked up my handbag and followed her out to the taxi,
reflecting on how it had come to this.
=#=
"You're really happy for me to do this?"
"Of course, darling," my wife responded as we entered the salon. "I
know you've always wanted to do this. You're a keen cyclist so it is
not that unusual, and now you are not at work, no-one there is going
to be bothered are they?"
"Ok," I said and introduced myself to the receptionist.
"Ah, hello Mr. Jones. You're here for a full leg wax."
"Ah yes," I stammered in response. "I've always heard that it helps
with cycling so now it's the summer I thought I would give it a go."
"Very good," she responded. "Is your wife joining you?"
As I looked to my wife she answered.
"No, I have some shopping to do. I'll be back in..."
"Oh, he'll be done in about an hour," the receptionist answered.
"Okay, an hour. See you later, dear," she said, waving as she left the
salon.
"Right Mr. Jones, if you can follow me," the receptionist said, "Gemma
is ready for you."
After an hour on excruciating pain, I had hairless legs for the first
time in my adult life, something I had wanted for years, but never
really built up the courage to do. At Gemma's suggestion, I had also
had my back and chest waxed because she thought it looked unsightly
and commented that many cyclists and swimmers are clean shaven all
over.
My wife turned up just as Gemma showed me back to the waiting area.
"Everything okay," she asked. I grimaced in response while Gemma made
some comment about me being very well behaved.
=#=
Back home my wife suggested that I have a shower to clean off all the
wax and handed me a bottle of moisturiser.
"Make sure you use this when you get out of the shower. It will keep
everything smooth for longer."
While I was in the shower, I took the decision to shave my armpit
hair. I wondered if she would notice or be bothered. When I got out of
the shower I found that my wife had laid out some of my favourite
underwear on our bed, a pair of blue satin gossard panties with a
matching suspender belt and a purple teddy I had bought her some years
before. When I saw the new packet of sheer stockings next to the pile
of underwear, I realised that she had left it out for me to wear. You
see, I had been a semi-closet cross-dresser for many years. My wife
had tolerated this part of my life, but never really encouraged it.
Perhaps this was going to change.
Drying myself off, I eagerly stepped into the panties and clipped the
suspender belt around my waist. Slipping the suspenders underneath the
elastic of the panties, I sat on the edge of the bed and opened the
stockings. I was just about to pull the first one up my left leg, when
my wife walked into the room.
"Hold on," she said, and as I stopped she continued with a smile, "I
see you have found what I left out for you. I didn't think you would
need much encouragement, but before you put the stockings on, how
about some nail varnish?"
I couldn't believe my ears or luck and nodded eagerly. Popping into
the bathroom she came back two toe spacers and a bottle of 'Miracle
Mauve'. As I sat there in her panties and suspender belt, she painted
my toe nails carefully. When she was done, she asked with a cheeky
smile, if I wanted my finger nails done as well. I demurred but said
no, not wanting to cause any problems if we had a sudden visitor
later. She left me to wait for the varnish to dry and finish getting
dressed. The feeling of pulling stockings up my hairless legs for the
first time is something that I will always remember!
I was just about to step into the teddy when I remembered something
else. Often times in the past I had used and a tampon and ST to make
myself feel more feminine. Stepping into the bathroom, I pulled the
panties down and inserted a moisturiser smeared tampon into my hole
and popped a panty liner in my panties. Ready to go I quickly returned
to the bedroom to put on the teddy followed by a pair of red slacks
and a satin t-shirt which I dug out of my secret stash. Slipping my
nylon encased legs into the ballet pumps I recovered from my stash I
was ready. Not quite how I wanted to look, but relatively safe and
ease to change in case anyone knocked.
My wife was actually disappointed when I joined her downstairs.
"Why are you covering up your legs? I thought it was what you always
wanted," she asked. "Don't you have a skirt you could wear in that
stash of yours?"
I blushed, partly because she clearly knew about my stash, but also
because she was encouraging me to wear a skirt. I explained my
reasoning.
"Don't worry about that, dear. If anyone does pop round, I can answer
the door and you can go up and change. Now off you go, pick something
nice out."
Not quite believing this was happening, I went back upstairs and
picked out a black and white satin skirt that fitted my waist snugly
and finished just above the knee. Acknowledging that she was right to
encourage me I smiled at what I saw in the mirror. That was more like
it. Once she has praised me for my choice, she handed me a drink and
toasted new beginnings. She had ordered a take out from our favourite
restaurant and this was to be a celebration of the start of my early
retirement. Over dinner she surprised me with the news that we would
be going away the very next day for a few days to get away from it all
and think about next steps. This was a pleasant surprise as in the
head long rush towards the last few days of work, I hadn't really
thought about what next.
After dinner I tidied up the remains of the meal. When I was done, I
discovered my wife was already upstairs in the bedroom. She was sat in
bed smiling wearing a red satin nightdress, one of a pair we had
bought many years ago. Mine was draped over the end of the bed. I
kicked off the pumps, slipped the skirt down my legs and took the t-
shirt off. Slipping the teddy's straps off my shoulders and letting it
slide down my body, I picked up my nightdress and slipped it over my
head. Leaving the stockings on, I climbed into bed and snuggled in
next to my loving wife. There followed the most passionate sex we had
had for many years as we explored each others' hairless and satin
draped frames. When she tried to pull down the panties I was wearing
to gain access, she discovered the panty liner and asked me why.
"To feel a bit more feminine," was my answer, in response to which she
gave me a cryptic smile and as she did so she moved her hand inside
the panties towards my rear. Finding the string to the tampon her
smile widened as she gave it a little tug which in turned caused me to
give an involuntary moan.
=#=
The following morning I woke with a smile on my face as I realised it
hadn't been a dream and that I was lying in bed wearing panties and a
nightdress, and with a hairless body and painted toe nails. My wife
brought me a coffee in bed and then encouraged me to go out for a bike
ride for a couple of hours while she backed. As I protested she told
me not to worry, she knew what needed to be taken and where my stash
was.
On return from the ride my wife informed me that the car was packed,
all I needed to do was get have a shower, get changed into the clothes
she had left out and then come down for dinner. In the bedroom, my
clothes were already laid out on the bed; a pair of black panties with
a lacy front and satin rear with matching suspender belt, the purple
teddy, satin t-shirt and ballet pumps I had worn the previous evening,
the red slacks I had originally worn and a brown pullover. Lying next
to them was a panty liner and a tampon! Not needing any second
invitation, I got ready in the clothes she had left out for me.
I came down for lunch slightly perturbed that we would be going out
with me dressed like this and whether or not I needed to take anything
else. My wife reassured me that she had pulled the car right up to the
house so no-one would see and that she had thought of everything.
As was sat in the car on the drive, she leaned over to me.
"Do you trust me?" she asked.
"Of course," I responded on which she gave me a kiss and then slipped
a blindfold over my eyes.
"I don't want to spoil the surprise," she added sweetly.
=#=
Some time later, along time after I had given up trying to work out
where we were going, I could feel the car slowing doing and turning
right. The sound changed from tarmac to gravel and gradually we came
to a rest.
"Now you can take the blindfold off," she said.
After I had allowed my eyes to become accustomed to the light, I saw
we were parked up outside a large country house. There was no signage
that I could see, but it looked most splendid. Getting out of the car
we went to the boot to get out the bags, three of them, one was the
suitcase I kept my stash in. When I looked at the other two my wife
just said I would find out later. I felt self-conscious walking across
the gravel driveway in plain sight dressed as I was, but my wife gave
me a reassuring and lingering pat on my rear and told me all would be
well.
Entering the house we rang the bell at Reception and a moment or two
later an imposing woman of a certain age came out of the back room to
greet house.
"Ah welcome, you must be Mistress Angela and Miss Aimee. I am Mistress
Jean, although you can call me Madam if that is easier."
My eyes went wide and I stared, mouth open, at my wife. What was this
place she had brought me to? She just smiled and gripped my hand.
"Do come this way," Mistress Jean said, beckoning us into the room she
had just left, "You can leave the large bags there."
We followed her in the office, me carrying the smallest bag as
instructed. There were only two seats in the office, one for Mistress
Jean and one for my wife. I was instructed to put the bag down and
stand behind my wife while she explained why we, or rather I, had
turned up. She spoke of my history of cross-dressing, my desire to
spend time dressed during the holidays and the balance between wanting
to be seen but also not discovered. I was embarrassed by this all
being said in the open in front of someone else, but also amazed. All
those conversations when I felt she had been really short with me when
I was talking about it, she had been listening after all. Eventually
Mistress Jean turned and looked to me.
"So Miss Aimee, let's have a look at you. Down to your underwear
please."
I was gobsmacked and this clearly showed on my face.
"Well you really are going to have to do a lot better than that Miss
Aimee if you are going to get on here," Mistress Jean said sternly.
"Mistress Angela has spent a lot of time and effort planning this, I
hope you are going to repay all that effort."
I looked to my wife who smiled and nodded at me, mouthing the words
'trust me'. I turned back slowly to face Mistress Jean, not really
believing I was about to do this, "Yes, madam," I responded and
removed my jumper, slacks and t-shirt until I was standing there just
in stockings and the teddy. She got up and walked around me making
affirmative noises.
"Good, very good, and everything is in the bag as instructed," she
said, directing the comment to my wife to which my wife responded
affirmatively.
"Excellent," Mistress Jean continued sitting down, "I definitely think
there is potential here." She rang the bell on her desk and after a
couple of moments another door opened at the back of the office
opened. I started and tried to cover myself up to which Mistress Jean
let out a little laugh.
"Oh don't be silly, this is not the first time Mistress Natasha has
seen someone dressed like you. Now, pick up your clothes and the bag
and follow her through to the next room. Mistress Angela and I have
things to discuss without you. We will see you shortly."
I did as was instructed and found myself in a room that looked a
little like a beauty salon. Mistress Natasha took the bag from me,
opened it and started removing the contents; a white blouse, black
skirt, a black bra that matched the panties and suspender belt I was
wearing and my heeled shoes. Looking at the bra she nodded and told me
to remove the teddy and sit on the bed in the middle of the room while
she fetched something. Moments later she returned to me holding two
silicone breasts. When I looked at her questioningly her response was
matter of fact.
"Well, we can't have you stuffing your bra with panties while you are
here, it needs to be done properly." She then proceeded to attach the
breast forms expertly in just the right area before handing me my bra.
When I put it on it was almost as if I had never worn a bra before.
The impact of putting one on when you have breasts, even fake ones was
amazing, the way it took the weight and created a cleavage, "Wow," I
exclaimed.
"Yes, they are quite impressive aren't they," she said. "You will need
to keep the bra on when you go to bed tonight just to ensure the
breast forms are kept firmly in place. Now finish getting ready, I
need to do your make up and hair."
I slipped back into the teddy which now formed itself to my altered
shape before stepping into the skirt and shoes and buttoning up the
blouse. Following instructions I sat at a dressing table while
Mistress Natasha fitted me with a dark brown, shoulder length wig,
until my own hair grew out she said, and then applied make up to my
face while the varnish she applied to my nails dried. The whole
process only took about half an hour at which point she knocked on the
door to the office and on Mistress Jean's command, opened the door and
showed me in. The look of surprise on my wife's face was priceless,
and Mistress Jean was pleased.
"That's after only half an hour. Imagine the change after two weeks or
a month."
Now it was my time to look surprised.
"Now Miss Aimee, Mistress Angela has, as you know, a long way to
travel to get home tonight so I suggest you take her back out to her
car and say farewell and thank you. When you return to Reception, Miss
Susannah will be waiting to showing you to your room."
There was to be no discussion or argument and in stunned silence I did
as I was told. It was only when we got to the car that I said
anything, and all I said was "Why?"
"Why not," she responded. "You've always wanted to do something like
this. Don't deny it, I've read your stories, some of them are very
good, if a bit racy. Just go with the flow and enjoy it. I'll see you
next weekend."
And with that she was in the car and gone, leaving me standing outside
in my new outfit and persona. "Just go with the flow," I said to
myself as I headed back in doors to meet Miss Susannah. Where was the
flow going to take me?
=#=
Miss Susannah was a little shorter than me, slim with shoulder length
auburn hair and a sweet smile. She was also wearing a black skirt with
a white blouse, which was opened enough to reveal a hint of cleavage.
"Good morning, you must be Miss Aimee," she said, extending an
immaculately manicured hand towards me. "I am Miss Susannah, although
you can call me Susie when no one else is around," she continued,
looking around furtively. "Let me show you to your room."
I picked up my stash suitcase and the small bag the clothes I had
turned up in had been put in while Susie picked up the other bag which
contained I knew not what. I followed her up a couple of staircases
until she stopped at a door and opened it into a large bedroom with
what looked like a super king size bed in the middle of it. There were
two dressing tables, built-in wardrobes along one wall, a comfy
looking sofa and a door that I assumed led to the en-suite bathroom. I
noticed that one of the dressing tables had stuff on it, but the other
was empty. Before my thoughts on this developed, Susie told me.
"This will be your dressing table," she said, pointing towards the
empty table. "There is an empty wardrobe here," she added, opening one
of the large wardrobes. "I have also made some space for your stuff in
the bathroom, come and look."
Putting down the bags I followed her into the bathroom which contained
a large corner bath with shower screen, toilet, bidet, sink and towel
rail. As she has said, the utility unit containing various products
had had space cleared for more products, presumably mine. She clearly
saw the confused look on my face, but misinterpreted it.
"If you need more space," she said, looking slightly worried, "Let me
know, I am sure I can move some of my other stuff." It then dawned on
me and my raised eyebrows and rounded lips let her know. "Oh," she
continued, "I should have said, we will be sharing this room. I hope
that is okay?" I remembered what my wife had said about 'going with
the flow'.
"I am sure it will be absolutely lovely," I said, wanting to make a
good impression and not wanting to upset her as she was clearly
accommodating me in her space. I guess she knew what I was so there
would be no need for any subterfuge. "As long as you are happy to have
me share with you," I added, walking back into the bedroom.
"Of course. It will be great fun. And don't worry," she said, reaching
out to hold my hands, "I know this is going to be a bit of change and
possibly quite difficult at times for you, but I am here to help. To
begin with, however, I am going to leave you alone to unpack, unless
you'd like me to help."
"Thank you," I replied, earnestly, "It's kind of you, but I think I
would like some time alone to reflect and unpack myself if that is
alright."
"Of, course," she responded brightly. "I will leave you to your own
devices and return later."
As she closed the door behind her, I slumped on the edge of the bed.
Wow! What a turn of events! Is this really what my wife and I wanted?
I sat there thinking for a while before returning to my wife's
comment, 'Just go with the flow', and started unpacking.
I started with the new bag that I didn't recognise. The first thing I
noticed was a small parcel wrapped up with a pink bow. Attached to it
was a card. Opening it I found a note from my wife.
"Dear Aimee," the note started, "I realise that for many years you
have yearned to have a much bigger role in our relationship but I have
been reluctant to encourage or allow this. Now you have finished
working I think it is about time I gave you your chance. Mistress Jean
and her team have a really good reputation for training people like
you in femininity and general domestic chores, something which I have
always done willingly before now. I realise this will be a big change
for you, but I urge you to embrace the change and enjoy every moment.
I will be in touch. Your ever loving wife, Angela. PS: The parcel
contains two small gifts which I thought you might like."
I was stunned. How long had she been planning this? I opened the
parcel and found inside two smaller boxes. One contained a silver
necklace and the other a delicate silver wrist watch. Putting on the
watch I noticed how right it looked against manicured fingernails.
Fitting the necklace around my neck, I looked down to see the pendant
hanging just above my 'cleavage'. It wasn't a big change, but it
definitely helped me feel more feminine. Wiping a tear of joy from my
cheek, I continued with the unpacking.
The other contents of the bag fell into two categories. The first was
lingerie I had bought my wife over the years but she had rarely worn.
She had passed on to me several pairs of panties, so much so that I
could probably wear a different pair every day for at least two weeks,
and a green satin camisole and French knickers set. She had also
packed some new tights, stockings and hold-ups in both nude and black.
The other category of contents was various boxes of products, all
seemingly from a company called Feminem that I had not heard of
before. There was a large box of applicator tampons, some STs, a
bottle of shampoo, conditioner, shower gel, moisturiser and all the
other necessary toiletries. There was also a good starter range of
make up including everything from nail varnish to eye liner. There was
also a bottle of my favourite perfume, Eden. I gave myself a little
spray and smiled. Finally there was a pair of fluffy mule slippers.
I picked up all the toiletries and took them to the bathroom, putting
them in the space that Susie had left for me. As I caught my
reflection in the mirror I smiled. I was being given permission, and
help, to be the me I had wanted to be for so long. Returning to the
bedroom, I arranged my make up and accessories on the dressing table
and then started filling the drawers with under wear. After unpacking
the panties and hosiery my wife had passed on to me, I opened my stash
suitcase and started taking everything out of there to pack. I had a
drawer for hosiery, another for panties, one for bras, one for
nightwear, one for teddies, camisoles and the like and a final drawer
for special items like my blue basque and my suspender belts. As I
stood there looking at the drawers filled with their shimmering
contents, I couldn't believe how much lingerie I had amassed over the
years, but I also knew that, given the chance, I would want to get
some more!
In the wardrobe I hung up the four dresses I had, plus my other two
blouses, three skirts and two pairs of slacks. The contents of the
wardrobe looked meagre in comparison to the dressing table and I
suspected I would need to expand, particularly in blouses, for work. I
placed my spare pair of pumps and my new slippers at the bottom of the
wardrobe and hung my dressing gown on the back of the door.
Just as I finished, Susie walked back in.
"All done," she asked.
"All done," I replied.
After showing me where to stow my empty bags, Susie took me back
downstairs to meet Mistress Jean again. She knocked on the office door
and waited until she was called in.
"Miss Aimee for you, Mistress Jean," she announced with a brief
curtsey then ushered me in with a quiet "See you later" before closing
the door behind her and leaving me alone with Mistress Jean.
"Well Miss Aimee, do take seat. I do like your necklace and wrist
watch."
"They were a present from my wife," I responded.
"That's all very well and good," Mistress Jean replied, "but I do not
recall asking you to talk and I am sure Mistress Angela would be
disappointed to hear about you getting off to a bad start. However, I
shall forget about this slip and put it down to your enthusiasm."
I blushed at having been told off.
"Now," she continued, "Mistress Angela has told me a lot about you and
your development as Aimee over the years. She has told me that you are
quite a good story writer. You shall have to show me some in the
future, but for now, let me explain why you are here. Mistress Angela
wants you to be inducted into the wonders of femininity, something you
have been trying, with some success, to do by yourself over the years.
I can assure you that after you spend time with us, your induction
will be much more successful. She has also said that should would like
you educated in a wide range of house hold chores, something you have
not been totally familiar with over recent years."
Again, I blushed as I felt admonishment in her tone of voice.
"Miss Susannah will help me help you learn how to be and act like a
woman and how to serve all needs around the house. If you respond
appropriately, all well and good, but if I have any reason to think
you are not learning and you are treating this as some kind of game or
hobby, I will respond appropriately. Do you understand?"
"Yes, Madam," I responded meekly.
"You will be expected to dress and behave like a woman throughout your
time with us, and follow any guidance from myself, Miss Susannah or
any other member of staff. As we open to members of the public, you
will also be expected to present yourself impeccably at all times. Do
you have any questions?"
I hesitated briefly then nodded.
"Well go ahead then."
"How long am I here for?" I asked.
"As long as Mistress Angela feels is necessary following any advice I
give her," Mistress Jean responded, "anything else?"
I shook my head.
"Just one more thing before you go, Mistress Angela has told me you
are so keen to be feminine that when you dress you often use feminine
hygiene products in order to feel more so. Is this correct?"
"Yes, Madam," I responded, blushing slightly.
"That is good to hear, and this is something I will be checking on a
regular basis. Are you using any products now?"
"Yes, Madam."
"Please show me."
"Excuse me?" I responded, confused.
"Please show me you are currently using feminine hygiene products. I
need to know you are telling the truth. Trust takes time to build."
I hesitated a moment, but under her hard stare I gave in. Unbuttoning
and unzipping my skirt, I let it fall to the floor and stepped out of
it, but then I remembered I was wearing a teddy with no gusset poppers
which meant unbuttoning my blouse and then slipping the teddy off my
shoulders and letting it fall to the floor as well. I stood there in
front of Mistress Jean, glad only in my lingerie and stockings.
Turning my back to her, I hoped she could see the wings of the ST that
I had wrapped around the gusset of the panties, but I somehow knew
that wouldn't be enough. I slowly slipped the panties down my thighs
and bent over clearly exposing the string of the tampon hanging out of
my hole as well as the ST in my panties. I waited for a response from
her for what seemed like ages.
"Well, I am pleased to see that you can be trusted," she said at last
from behind her desk. "Now, get dressed again."
The sense of relief at being able to cover myself up again was
palpable, however, as I pulled the panties up, I realised to be horror
that I had become aroused. I hoped that by the time I was fully
dressed, it wouldn't be so noticeable. If it was, she didn't say
anything. She continued to talk while I was dressing.
"It is a pity your underwear doesn't match fully," she continued,
"Perhaps I will have a word with Mistress Angela about that. I do feel
a lady should always wear matching underwear. Now before you go, I
have one more thing for you," she said, handing me a small bottle.
"This is something to help with your voice. You need to spray it in
your mouth twice a day, once in the morning and once before you go to
bed. I will help soften you voice a little although we will also give
you voice training. Use it now."
I noticed the branding on the bottle, Feminem, the same as the
products my wife had packed for me. I gave it a spray into my mouth.
It felt cold and tingly but had no discernable flavour. I popped the
bottle in the pocket on my skirt.
"Now, Miss Susannah should be waiting for you outside, off you go. I
will see you later," and with that I was dismissed.
=#=
Susie spent the rest of the day showing me around the hotel and
introducing me to all the other people who worked there. I say all,
there was really just herself, Mistress Jean, Mistress Natasha, the
cook, Mistress Katherine, and Jo who sorted out all the practical jobs
that no one else could do.
I was shown where the laundry room was, the kitchen and restaurant,
the cleaning cupboard, the bedrooms, the gym, all over the house, I
wasn't expected to do any work on my first day, just to acclimatise.
In fact there were no other guests in the hotel on that day so it had
been decided that, in honour of my arrival, we would all have dinner
together in the dining room. Apparently this was a rare occurrence and
was a special treat.
I helped Susie prepare the table and then I was told to go and get
ready for dinner. When I questioned this, I was told to change into
something I might wear out to a restaurant rather than the work
clothes I was wearing. As it was a warm evening, I decided to put on
the sleeveless satin Wallis dress I had bought a couple of years
previously. Although it was a lovely dress, I had always felt slightly
disappointed wearing it as I could always see me chest and armpit
hair. Now I didn't have any I relished the prospect.
Back in the room, I took off the skirt, blouse and teddy and caught a
glimpse of myself in the mirror. I was impressed with how good I
looked although I knew there was room for improvement. I got slightly
nervous standing there in my underwear in case someone else came into
the room but I figured that as I was sharing a room with Susie, I
would have to get used to that. Slipping in to the dress I did the
rear zipper up with some difficulty but was thoroughly pleased with
the outcome. I really did fit me well and looked much better without
all the unsightly hair sticking out. As I sat down at my dressing
table to touch up my make up, Susie came in to get changed herself. I
tried not to stare as she slipped out of her work clothes showing a
beautiful pale blue satin basque and matching panties, the basque was
done up tight to show off her voluptuous cleavage. She slipped a knee
length red satin dress over her head and like me sat down to touch up
her make up. When she was done, she offered to check mine. Impressed
with my beginners' efforts, she reassured me that make up lessons
would be part of the training.
=#=
Dinner was a lovely affair and Mistress Katherine joined us to eat
which was nice as it is always good to thank the chef. They all
toasted my arrival.
After dinner we sat in the bar chatting until eventually Susie got up
to go to bed. I made a move to follow her, but she insisted I stay
downstairs with the others saying she was only going to bed early as
she had had a late night the previous night sorting out her room.
It was only about fifteen minutes later that I headed up, realising
that I too was tired after my exciting day. When I arrived at the
room, Susie was already in bed but she had put my beside light on and
left the bathroom light on. I tried to get undressed quietly. As I
unzipped the dress I realised I was desperate for a wee and so,
skipping into the bathroom in my underwear, I pushed the door behind
me, lifted the seat, slipped my willie out of the panties I was
wearing and let a long stream go. I realised it was unladylike, but I
was desperate. Once I was done, I popped my willie back inside the
panties, flushed the toilet and headed back into the room as quietly
as possible. Clearly not quietly enough because I hadn't closed the
door properly and the sound of my lengthy toilet stop and the flushing
had clearly woken Susie as she then popped into the bathroom, closed
the door firmly behind her and visited the toilet herself.
Taking the opportunity of being alone, I quickly unclipped the
stockings and, sitting on the edge of the bed, slipped them down my
smooth legs. Unclipping the suspender belt, I popped it back in the
drawer and then picked out my favourite pink nightdress and slipped it
over my head, luxuriating in the delightful feeling as it shimmered
down my body.
I was sat at my dressing table removing my makeup when Susie came out
of the bathroom.
"Sorry for waking you," I apologised.
"Don't worry, I was only half asleep and needed a wee."
I finished off removing all my makeup and, following Susie advice,
moisturising, brushed my teeth and then slipped into bed. It was a big
bed and I did not have to get too close to Susie, but it still felt
strange.
"Goodnight," Susie said.
"Goodnight," I replied, turning off the lamp, but I stayed awake for
ages considering all that had happened. What a day! What would
tomorrow hold?
=#=
Susie had woken before me and she was walking out of the bathroom,
towel wrapped around her breasts and drying her hair when I woke up.
"Good morning, sleepy head," she said, "Time to get up and ready for
work."
"What should I wear?" I asked, timidly.
"Well, unless we are told otherwise, we are expected to wearing
something smart for work, usually a dark skirt and a blouse," she
replied. "Can you manage that?"
"Oh yes," I replied, more eagerly than I had expected. I jumped out of
bed and was startled by the feeling of weight on my chest. Oh yes, the
breasts forms. I had forgotten. I couldn't help look at myself in the
mirror all hairless and soft, with painted nails and delicate
nightwear. This really was what I had wanted for a long time. The only
real anomaly was the short hair. I glanced at the wig on the dressing
table, maybe soon.
"Stop admiring yourself or you will get in trouble for being late."
I went to the bathroom, stripped off and had a quick shower, wearing a
hair net so as not to get my hair wet before I put the wig on. When I
came out as Susie had done so minutes before hand, she was sat at the
table in her lingerie drying her hair. I tried not to stare, but she
was beautiful. She smiled back at me in the mirror.
I knew she knew my secret, but I was still shy about it so I tried to
be discrete as I picked out some white satin and lace lingerie that
almost matched, bra, panties and suspender belt. Sat on the edge of
the bed, I opened a new packet of nude stockings and pulled them up my
hairless legs, clipping the lacy stocking tops to the suspenders. I
wore the same skirt I had worn the previous day, but matched it with a
different, taupe coloured, satin blouse. Sitting at the dressing table
I attempted some make up. Slipping on my shoes, I was ready when Susie
called me.
I was just about to leave with her when I remembered something.
"I will be down in a minute," I said. "I've forgotten something."
"Okay," she answered, "See you down there."
Once she left I headed back to the bathroom, I had forgotten sanitary
protection. Quickly I inserted a new tampon and fitted an ST in my
panties. I didn't want to get caught out! Feeling nervous but ready
for the day ahead, I gave myself a quick spritz of perfume and headed
down for breakfast.
=#=
After breakfast I was called into Mistress Jean's office and once
again asked to prove that I was wearing sanitary protection. It was
much easier without having to remove blouse and teddy, and once she
was satisfied, I pulled up my panties and started to reach down for
the skirt.
"Not so soon," she said, and I stopped, looking at her quizzically.
"Do you recall that yesterday I said one of the reasons for you being
here is to learn how to be like a woman?"
When I realised this was not a rhetorical question and that she
actually wanted an answer, I did so affirmatively.
"Well then," she continued, "To do something that is directly counter
to that is either a gross slip of ignorance or defiance."
I look confused and felt worried.
"Let me ask you another question. We are trying to help you learn how
to be like a woman, in all things. How would you say a woman normally
goes to the toilet?"
"Sitting down," I replied and then there was a slow dawning of
realisation.
"You clearly know the correct answer, so it is surprising that I have
been told you went to the toilet yesterday evening like a man,
standing up. Is this true?"
There was no point in denying it, so I admitted that I had done so,
all the while feeling growing anger towards Susie.
"Now the person who told me was only doing what I had asked her to do
so there is no point getting stressed with her, but you need to be
taught a lesson. Do you agree?"
"Yes, madam," I replied, nervous about the lesson she might be about
to teach me.
"Well then," she said, standing up from her table, picking something
up and walking round towards me. "Do you know what this is?" she
asked, holding up the item.
In response to my shaking head, she continued.
"This is a gaffe, a pseudo vagina. You are going to wear it until I
decide you have learned you lesson. While wearing this you will be
able to go to the toilet and perform as normal, but you will not be
able to wee standing up. Drop your panties, now," she commanded.
Doing what she ordered, I stood there as she fitted the gaffe to me.
It slipped over my willie, which was thankfully flaccid, and had
straps around my waist and under my groin, pulling my willie back and
holding it firmly in place. Once it was in place I heard a click as
she stood up, holding a small key.
"Now you are locked in. You may find this uncomfortable, but you will
learn your lesson. Now, get dressed."
I pulled up my panties over the gaffe and was surprised with how flat
my front appeared. Once the skirt was in place, the effect was very
pleasing.
"Now, off you go, we both have things to do."
Susie was waiting outside and apologised as soon as I she saw me. I
frowned at her and didn't speak, walking straight past her to Mistress
Natasha's room where my first lesson was to learn make up.
After lunch we had to get the hotel ready for visiting guests and
thankfully I didn't get the chance to talk to Susie, but I knew it
couldn't last. We were sharing a room after all.
=#=
At the end of the day once all the guests had arrived, had their meal
and were sitting in the bar, I was dismissed and headed up to the
bedroom, slightly nervous about what would happen as I knew Susie was
already up there. When I walked into the room, she was sat in the bed,
clearly waiting for me, and looking nervous, biting her lower lip. She
jumped out of bed, her delicate nightdress floating around her as she
walked towards me, her breasts bouncing with each step.
"Please forgive me, Aimee," she said, holding out her open hands.
"Why did you tell her?" I asked.
"Because she told me I had to let her know when you got something
wrong so you could be trained. I didn't want to but I was doing what I
was told. Sorry," she finished, a sad look in her eyes. "Do you
forgive me?"
I wasn't really sure, the gaffe hadn't really been too painful during
the day, only a couple of times when I went to the toilet or became
aroused, then it was really painful. I did want to be friends with her
so I said that yes, I did forgive her.
She beamed a smile.
"Good," she said, because I managed to persuade Mistress Jean to give
me the key, and skipping over to her dressing table she picked up the
small key. "Well," she continued, "Do you want to take it off?"
I was clearly keen to get out of the gaffe, but was also nervous about
exposing myself in front of her. She clearly saw the nerves.
"Don't worry," she said reassuringly, "You haven't got anything I've
not seen before," so I stood before her and unzipped my skirt. Letting
it fall to the floor, I stepped out of it and my shoes as Susie knelt
in front of me. Slowly I slipped the panties down my legs, stepping
out of them as well. Susie reached around behind me, undid the lock
and released the gaffe. As she pulled it away from my groin, my willie
sprang up and I felt mortified. Susie just giggled.
"Don't worry, darling, its just excited to be released. "Now let me
clean and soothe you," she continued, taking my hand and pulling me
over towards her dressing table. Kneeling down in front of me, she
wiped my willie and groin area with some cleansing wipes, then
massaged the areas that had been trapped all day with some
moisturiser. I couldn't control myself with this arousing action and
my willie quickly became engorged.
"Oh dear," she said, "That's not very ladylike. We will have to do
something about that," and before I could do anything, she closed her
mouth around my willie and started licking and sucking on it. It
didn't take long for me to explode in her mouth, and she kept
swallowing until the pulsing ceased. Licking her lips, she stood up
and looked me in the eyes. "I hope you accept my apologies, now you
best get ready for bed." I nodded through a daze as she left the
bathroom.
Moments later, I was in bed next to her in my nightdress and panties,
no bra tonight as Mistress Natasha had confirmed the breast forms were
secure. Susie turned to me.
"I do want to be your friend and help you. I do understand what you
are going through."
"How can you understand," I replied.
"Let me explain."
She reached out and took one of my hands. Taking it under the bed
clothes, she held it on to her satin framed chest and then slowly slid
it down her body towards her groin. When our hands reached her groin,
she hesitated, pulled back the hem of her nightdress and laid my hand
on the front of the panties she was wearing. As she did so my eyes
went wide and she smiled, the front of her panties was not flat as I
had expected, but nestled inside and now growing under the warmth of
my hand was her own willie! In my shock and surprise I kept my hand
there for a while before quickly moving it. A slight look of
disappointment crossed her face and I stammered out, "Why ... how ...
what?!"
She smiled and then told me her story. She was Mistress Jean's husband
and together they had brought and opened this hotel. However, one day
Mistress Jean had caught him snooping on Mistress Natasha as she was
getting dressed. His punishment was to be the maid in place of
Mistress Natasha, and for her and Mistress Jean to watch him getting
dressed in women's clothes. The promises of the punishment ending once
he had learned his lesson came to nothing, and eventually he began
living as Miss Susannah full time with Mistress Natasha becoming co-
owner and partner with Mistress Jean. The relationship with all seemed
very positive, but there didn't seem to be any of his former self
left.
"But, your breasts," I asked.
"Either a punishment or a present whichever way you choose to look at
it. To begin with I thought of them as the former, but I have become
quite attached to them now," she smiled.
I was shocked and surprised and didn't really know what to think or
say.
"You probably have loads of questions," she, and I couldn't see her as
anything other than a she, continued, "For now, it is probably best
for you to get some beauty sleep," leaning forward she gave me a quick
kiss on the lips before turning out the light.
A couple of minutes later I turned my light off and rolled on to my
side. I felt and a heard a rustle and then Susie was behind me,
spooning me, "You'll be fine," she said as she leant in to me and I
could feel her softening willie at my back.
=#=
The following morning I woke earlier than Susie and lay watching her
for a bit as the early morning sun eased through the curtains. Even
though I now knew her secret, I couldn't see her as what she really
was, a she-male or whatever you want to call it. She looked totally
feminine and happily so. As she breathed slowly her chest and breasts
rose and fell inside the satin of her nightdress. Her facial features
looked feminine as did her beautifully manicured hands at the end of
her slender arms. Had she always looked like this or had she had some
kind of surgery to enhance her features? Is this what my wife planned
for me to end up looking like or was she just thinking of a short term
experience? I shuddered not really knowing what to think, and as I did
so, Susie began to stir. Not wanting to get into a conversation now, I
quickly nipped in to the bathroom to get ready. As I showered I looked
down at my naked and falsely feminine form. Where was this experience
going to end up?
When I returned to the bathroom with a towel wrapped round me, Susie
was out of bed and had removed her nightdress. She was standing there
just wearing her panties. I could see only the faintest hint of a
bulge there and I raised my eye brows.
"No secrets now," Susie said slipping her panties down her legs,
exposing her now semi-turgid willie.
"No," I replied in a kind of daze, still seeing a woman in front of me
despite the distinctly unfeminine appendage.
"Good," she said, and sashayed into the bathroom to get ready herself.
=#=
My days settled into a regular pattern. I would spend some time
working in the hotel and spending dome time being instructed in all
things feminine. I learned the art of make up, walking properly,
eating and drinking properly, even sitting properly. Even though I had
been given a solution to spray into my mouth to enhance the femininity
of my voice, I was given elocution lessons as well. Apart from the
occasional male guest, there were no male influences at all and all
the literature had an overtly feminine tenor, so I was reading
magazines that I had never even opened before. When any male guests
did arrive, I was doubly nervous of exposure but thankfully no one
suspected anything, or if they did they were too polite to say so.
Every morning I had to report to Mistress Jean for inspection. She
gave critical feedback about my make up and what I was wearing. She
was particularly unhappy about my lack of properly matching underwear
but said that this was something that she would discuss Mistress
Angela, i.e. my wife, when she came to visit. I asked when this would
be but she didn't give an answer.
Every morning she also made me prove the fact that I was using the
feminine sanitary products as prescribed by my wife. While I felt a
bit humiliated about this to start with, I soon became used to it
although I didn't feel any better for it. However, one day, when
Mistress Jean instructed me to drop my skirt so I could show her the
sanitary protection I was wearing, I froze. I realised too late that I
had completely forgotten to replace the over-night tampon I had
removed first thing in the morning. Clearly she saw the look of shock
in my eyes.
"What's the matter, Miss Aimee?" she asked, "Have you forgotten
something?"
I knew there was nowhere to hide so I simply nodded my head, biting my
lower lip dreading what she might say or do.
"Well, well. That is most disappointing. Mistress Angela was so
insistent on you using the products she has provided you with and when
we met at the start of your stay here, we discussed a clear procedure
if this was to happen."
I didn't like her use of the word 'procedure'.
"Off with the skirt and panties as usual," she instructed.
"But..." I tried to respond.
"No buts. Get on with it girl," she ordered.
I slowly removed the skirt and panties as instructed, showing the ST
that was in the gusset of the panties, but exposing the fact that
there was no tell-tale string of a tampon hanging down from my hole
has expected. As I was removing my skirt and panties, Mistress Jean
placed two items on her desk. The first looked like a large tablet,
the second looked a little like a dildo. When I was ready I stood up
in front of her.
"The procedure is this. Firstly you will receive a smack of your bare
buttocks. This first time there will only be one smack, any subsequent
misdemeanours will mean the number of smacks increases. Then I will
insert this in your hole," she said, holding up the tablet. "Do you
know what this is?" she asked. I shook my head.
"It is a suppository," she exclaimed, "full of feminine hormones that
will be slowly released into your body during the day. What about
this?" she continued, holding up the other item. Again, I shook my
head.
"It is a butt plug. This is quite a small one but will serve two
purposes, making sure the suppository stays in place, and reminding
you all day of your misdemeanour. Now bend over."
I did as was instructed, placing my hands on her desk for support as
she got up from behind the desk and walked around. Before I could
brace myself, she raised her hand and gave me an almighty slap on my
behind. Two things happened, firstly a tear formed in my eye, and then
my willie stiffened slightly, almost as if I was enjoying this. I then
heard her putting on a rubber glove and felt her smear something cold
on my behind. As I started she simply pointed out that it was some
lubricating cream. She then pushed the suppository into my hole with
her finger, pushing it up as far as she could reach. That process
wasn't painful, but inserting the butt plug was. The shape of it
started thin then widened slowly before suddenly thinning again. I
could feel my hole stretching to accommodate the device and then
suddenly closing around the end of it, just leaving out a short flat
piece of plastic.
"Now get yourself dressed and stand up," she instructed, removing the
glove.
When I was done she looked at me and handed me a tissue.
"Dry your eyes, girl," she said dismissively, "You have work to do,"
and with that I was dismissed.
It took a long time to get used to the feeling of the butt plug.
Standing up and moving around was okay, but as soon as I sat down, I
could feel it pressing into me. That was a reminder that it was
holding in place a large dose of female hormones. What was that going
to do to me? Was I going to wake up with breasts?
At the end of a long day, I was sat at my dressing table removing my
make up when Susie walked in.
"Everything okay?" she asked brightly, and to that simple question I
burst into tears. Rushing over she knelt beside me and asked me to
explain.
"Oh dear," she said when I had told the story. "Well, what's done is
done. Let's get you ready and in to bed," she continued, wiping the
tears off my cheeks. "When you are ready, would you like me to help
you remove the butt plug?"
I nodded then finished removing the make up while Susie went to get
herself ready for bed. Once I had stripped down to just bra and
panties, I asked Susie if she could help me. We went into the bathroom
and, wearing a pair of rubber gloves, Susie removed the butt plug and
washed it off for me while I cleaned myself on the bidet. I half
expected or hoped that the suppository would come out, but nothing
did, and as I sat there cleaning myself I remarked on how friendly
Susie was being helping me with something a bit grim. Soon after I
slipped into bed alongside Susie, clean, refreshed with a new ST in my
panties in case any of the suppository did leak out. I leant towards
her and, thanking her for her help, kissed her briefly on the lips. As
I pulled away, she reached out and pulled me back.
"Any time," she said, and kissed me on the lips again. This time I
could feel her tongue and almost involuntarily I opened my lips and
let her in. We kissed fully, but briefly, before I pulled back
quickly.
"What's wrong?" she asked.
"Is this okay? I mean, my wife..."
"Your mistress," she corrected me, "Has sent you here to learn to be
like a woman, which also means learning how to kiss like one. I am
sure she won't mind."
"Okay," I said, unsure, but didn't move back in to her. "Perhaps I
should just go to sleep."
"Perhaps you should," she said smiling, "You have had a long day," and
leaning forward gave me a quick peck on the cheek.
But I couldn't sleep. I tossed and turned, troubled by the turn of
events, but also uncomfortable. My hole had been filled with the butt
plug and now suddenly wasn't. This felt uncomfortable. Clearly I was
keeping Susie awake as she turned towards me and asked what the
problem was. Remembering our agreement of 'no secrets', I told her.
"Oh, okay," she said, smiling, "I think I can help you there, but you
will need to help me as well", and she leant close to tell me her
plan.
"Are you sure this will work?" I said.
"I think so," she replied.
"And is it, like, okay?"
"That all depends on how you see it. If you see it as one girl helping
out her friend, then it is, friend. If you don't see me as a girl,
then, well, that's something different," she answered.
Reflecting on what I had been thinking when I watched her in the
morning, I realised that it would be okay, philosophically at least,
and followed her instructions.
We both removed our panties, exposing our willies. Following Susie's
instructions, I grasped her's in my manicured hands and slowly began
to stroke it. I had never masturbated another man before, but looking
in her eyes and seeing her breasts underneath her nightdress I felt I
wasn't masturbating another man, just a special girl. When her shaft
was hard, she passed me a condom to slip over it. I had done this many
times to myself, but never to anyone else. Again, I concentrated on
her being a girl. Once that was done she told me to get on to my hands
and knees, spreading my legs apart slightly. She knelt behind me and,
after applying some lubrication, brought the tip of her condom clad
shaft to touch my waiting hole. Holding there she asked if I was okay.
Realising I was about to give another man, I mean 'special girl',
permission to invade my hole, I meekly replied, "Yes".
Susie eased her stiff cock into my hole. She wasn't big, but she was
bigger than the butt plug and I let out an involuntary whimper. Unlike
the butt plug, her shaft was the same size all the way along and she
gently eased her full length into me. As she did so I could feel the
hem of her nightdress on my back and her groin against my buttocks.
Again she asked me if I was okay. As she did her cock twitched and I
gave an involuntary moan as my cock twitched as well. Pushing back
ever so slightly I muttered a breathless, "Yes".
Susie held her position, stroking my back and sides, but making no
attempt to fuck me, just hold her willie in me. I thought about how
this might look to anyone coming in, a she-male fucking a man dressed
as a woman. What would my wife think if she walked in? But I tried to
put these thoughts out of my head. Susie was a girl, not a man, I
rationalised. I was being trained to behave like a woman so this was
part of my training. Susie thought that if my hole had something hard
in it that gradually softened, it would feel better, and over the
subsequent minutes I felt she was right. No matter how odd this was,
my hole wasn't burning as it had before.
Some time later, her willie had softened so much it flopped out of my
hole and I could feel her ease off the bed and into the bathroom.
While she was there, I took the opportunity to insert a new tampon and
get ready for bed, again. When Susie returned I was in bed waiting.
"Thank you," I said, holding out a hand to her.
"That's okay," she answered smiling. "I am happy to help. I am sure
you would do the same for me."
And with that she leaned in to kiss me good night, leaving me to my
thoughts about another first.
=#=
I got up and dressed quickly the following morning, not wanting to
dwell on what had happened the night before. Perhaps I was over
thinking things, because during the day, Susie made no mention of the
events of the previous night. Even when we went to bed she mentioned
nothing and made no attempt to instigate anything other than a quick
goodnight peck on the cheek. I felt relieved that perhaps she didn't
see me as some kind of weird sex toy, but also slightly disappointed
that as a friend she didn't want to share any closeness. Perhaps she
was giving me space.
=#=
A couple of days later while I was getting the restaurant ready for
lunch, Mistress Katherine called from the kitchen to tell me that
Mistress Jean wanted to see me in the office.
I knocked on the door and waited for permission to enter. When I did,
I was surprised to see my wife sitting there, just as surprised,
perhaps, as she was to see how I looked. Well she had brought me here,
perhaps not seeing me for a few days she had forgotten what she had
gotten me in to.
"Hello darling," I started to say, before catching Mistress Jean's
eyes and correcting myself, "Hello Mistress Angela," I continued
instead, dropping a small curtsey.
"Well hello, Aimee," my wife responded. Even though we were both
playing the game, it surprised me to hear her call me that. "Mistress
Jean has been telling me how well you have been getting on. You do
really look the part." I blushed slightly. "I wanted to pop in and
check on your progress. Mistress Jean has said there have been a
couple of lapses, but that on the whole you are doing well. I was
going to stay for lunch, but Mistress Jean has said that it would be
beneficial for you to have some new, matching, underwear rather than
relying on my seconds and the other stuff you have bought behind my
back over the years. She so has kindly given me permission to take you
out for lunch and some shopping."
I looked to Mistress Jean for confirmation and she nodded. There was a
pause and I realised a reaction was needed.
"Oh thank you," I started, "That would be lovely."
"Why would it be lovely?" Mistress Jean asked. I looked confused and
then realised she was leading me to saying something, but what.
"It would be lovely to spend some time with Mistress Angela," I said,
hopefully.
"And?" she asked again, raising an eye brow.
Unsure, I hesitated and then continued with a questioning tone, "It
would be lovely to have some new underwear."
"Some nice, feminine, underwear?" Mistress Jean asked. Seeing what she
was leading at I answered.
"Oh yes, it would be lovely if I could get some beautiful new matching
underwear. A set that I can wear together like a properly matching
bra, panties and suspender belt."
Mistress Jean smiled and this time it was my wife who raised an
eyebrow.
"Well, if you are going shopping for lingerie, we will need to be
doubly sure not to be discovered. Perhaps it would be good to be
careful. Aimee, can you remove your skirt and panties"
Both my wife and I looked at her surprised, but at least I could guess
what was coming. As I followed her command, Mistress Jean revealed the
gaffe and explained what it did. My wife agreed that it would be a
good idea and watched avidly as I let Mistress Jean fit the device to
secure my willie in place. Pulling up my panties and skirt, Mistress
Jean suggested that perhaps I might like to change into something else
for the trip out. Taking that as my dismissal, I left the room and
headed up stairs.
=#=
A few moments later, I was back down stairs having changed into my
favourite, knee length, satin tea dress. I had also removed the
suspender belt and stockings figuring I wouldn't want the
embarrassment of any unwanted unclippings as we were walking around
wherever we were going shopping and replaced them with barely black
tights before I slipped on my pumps.
I was excited about seeing Mistress Angela and going out, but also
quite nervous. She smiled as she saw me arrive, agreed a return time
with Mistress Jean and then led me outside to the car. Once we were
moving, she spoke.
"Well you do look good, I am impressed," was her opening line.
"Thank you, I think?" I responded.
"What do you mean 'I think'?" she asked.
"Well, my wife congratulating me because I look quite feminine, a
little odd don't you think?"
"What would Mistress Jean say about that?" she asked.
"About what, oh the 'my wife' bit, but we're not there." I protested.
"No we're not, but you wouldn't want to get out the habit and get into
trouble, would you my darling," she said, patting my nylon covered
knee. "Anyway, you can tell me all about what's been happening while
we're travelling."
I gave her some idea of what had been happening but was vague on some
of the details. She asked me about the gaffe and how it felt. I
replied honestly that it wasn't uncomfortable at the moment, but I
knew it would become so later.
Soon enough we arrived at a large store and parked up. She eagerly
exited the car, but I was much more hesitant.
"What's the problem, my dear?" she asked, genuinely concerned.
"I've not been outside like this before. This is a bit intimidating,"
I responded.
"Oh nonsense," was her simple reply. "You look far more feminine that
many of the women walking around and I will be with you. Trust me."
So I did, I trusted her, and taking her hand stepped out of the car
and into the public. I needn't have worried. As my wife had said,
there were many less feminine looking people walking around and people
were getting on with their own business.
As the focus was buying matching lingerie that was the department we
headed to first. I couldn't help but feel nervous. Normally as a man
walking around such a department it is easy to feel out of place, but
here I was, appearing as a woman. It should be natural. My wife headed
to a large display of a range of lingerie and nightwear that came in
several colours. She told me I could pick two, and I chose a sage
green and a dusky pink, different to anything I already had. She then
focused on which type of bra to wear and what size it should be. We
went into the fitting rooms so she could help me try them one and I
discovered one of the downfalls of shopping for clothing wearing a
dress, I had to remove the dress to try anything on. Standing there in
my underwear and tights my wife commented on how feminine I looked,
even once I took the bra off. Although on close inspection the breasts
were fake, they looked good enough to be real. I decided on a full cup
padded bra in satin and lace. Getting dressed again, we headed back to
the display and she picked one of each colour and popped them in the
trolley. Then we had the choice of panties. I chose the full bum
variety rather than thongs as I liked the feeling of the satin. Two
pairs of each colour went into the trolley followed by matching
suspender belts, both quite deep with hooks at the rear. I thought
that was going to be it, but she was barely started. She also picked
out matching camisoles and French knickers in both colours. I began to
protest and she looked me squarely in the eyes.
"Are you seriously going to complain about me buying you lingerie?
This is, after all, what you've always dreamed of."
"Um,