Milking Time B4 Chapter 10 The Main Event Jordan
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The Story Of Jordan free porn video
STORY OF JORDAN
Although I did not realize it at the time, the opportunity that I accepted
during my last year at school was going to have a momentous affect on the
rest of my life.
My name is Jordan and I live with my Mother, who is a loan parent, as my
Father died from a heart attack some six months after I was born. My Mother
then dedicated her life to me. a She maintains a very active and enjoyable
lifestyle, with a wide selection of friends and hobbies and a busy social
life. My Mother is stunning in looks and has a gift for stylish and
glamorous dressing and always looks very feminine and immaculate. There
have been many men who have attempted to engage with her, but she has
steadfastly maintained her dedication to bringing up her Son (me) and has
deliberately avoided any intimacy with other men.
My Mother married very young at just eighteen and I was born less than a
year later. My Father came from a very wealthy family and so upon his death
my Mother was left a very wealthy woman, through both my Father's wealth
and the extremely large life insurance policy he carried. I have been
educated privately and enjoyed a first class education. My senior school
was an all boy's school with both borders and day students. I was a day
boy, as we lived only about ten miles from this exclusive school. This
brings me to the point where my story begins during my final year at
school, approaching the age of eighteen; I was studying for my A Level
exams, hopefully to obtain a university place to study drama and acting. I
am very slim built, not very tall and certainly not athletic, although I do
work and I am very fit.
Our school always presented a quality play at the end of the summer term,
being the end of the school year. We did three days of performances to
enable most parents and the local population the opportunity to see the
play. I have been involved in several roles over the years and really enjoy
acting, which has lead to the choice of my future career. At the beginning
of May of my final year, I was approached by the teacher who organized the
school play and invited to perform the lead role. It took less than a
minute to accept.
When I got home that night, I left it until Mother and I were sitting down
to dinner, before I told her my news.
"Mother, I have been selected to play the lead role in this year's school
play and if I am going to be successful, I am going to need a lot of help
from you."
"Why should that be?" she asked. "You have performed so well over the years
at other school plays without my help. What is so special about this part?"
"Well you see, the lead role is a woman."
"Wow!" she exclaimed. "And being an all boys school, there are no women to
select for the part that you have been chosen to perform."
"Exactly," I confirmed. "The thing is, it is a terrific role and I really
want to make a success of it and get totally immersed in the part. But the
last thing I want is to look like a bloke in a frock or a drag artist,
which is why I am desperate for your help to show me exactly how to be a
woman. Are you up for it?"
She frowned for a moment. "Let me think about this overnight and I will
come back to you tomorrow."
I know when to shut up and Mother is always so positive, the subject was
discussed no further.
On the way to school the following morning, Mother told me, "I have decided
to give you my wholehearted support to develop your role in the school
play, as you have asked. We will discuss how we go about it tonight and
between us formulate a plan of action."
"Mother you are the greatest. I am so lucky to have you around. I cannot
thank you enough."
"Actually," she said, "I think this could be a lot of fun for us both. Tell
me what the role is?"
"The character is a woman in her mid-thirties who is very successful in
business and her male colleagues are jealous and always trying to undermine
her. In fact there is only one female character in the whole cast. Despite
all the efforts of her male colleagues, in the final act she is made
Company President. My character is on stage most of the time, but the role
does involve four changes of outfit to go with the different scenes in the
play."
That night after supper, Mother and I sat down to talk about preparing for
this female role in the play.
"As I see it," Mother said. "We have just about three months to get you up
to scratch for this role. I think the only way we are going to succeed is
to do exactly as you said yesterday and get you totally immersed in the
character. That means you have got to look, walk, talk gesticulate and feel
like a woman. So I propose that in the evenings and weekends you become a
woman. We will get you a female wardrobe, makeup etc. and you will become a
woman under my guidance and instruction. We will make it so intense that by
the time the play comes to performance you will even think you are a woman.
How does that sound?"
"Oh Mother, this is very, very exciting. I can't imagine I will get as far
as you suggest, but I will give it a serious stab."
"Jordan, I can't wait to get started. This is going to be so much fun and
what a challenge."
On Friday night, Mother announced we were going shopping the following day
for the woman I was to become. She took all my measurements, to enable her
to select articles in my size. We were to pretend that articles were for
my. "Sister" who had seen them, but did not have the money at the time and
so had asked Mother to pick them up for her. We thought that shoe size
might be a problem until we found that Mother and I are exactly the same
size. Mother made a huge list of our requirements and this caused me some
concern.
"Mother, I really don't think you should be spending so much money for
this, after all it is only a school play."
"Nonsense," she retorted. "I am going to love every second of this!" She
came over and gave me a hug. "What fun it will be developing this
character."
The following morning we went into town to a large shopping mall and
started, what proved to be a mammoth shopping spree. We started by
selecting four outfits in line with the four acts of the play. An office
scene, an after work drinks get together, a cocktail party and a company
board meeting. Mum considered it very important that I approve of the
selections she made. We ended up with a suit consisting of jacket with
lapels and straight skirt in charcoal grey with a cream blouse to go under
the jacket. (office scene), A multi coloured short sleeved printed dress,
with full skirt (after work get together), A knee length LBD with spaghetti
straps and a modest neckline (cocktail party) and navy blue fine jersey
straight dress with matching wide belt (board meeting). We (or should I say
Mother) thought we could get away with two pairs of shoes so at the shoe
shop (our next port of call) she tried on, and bought, a pair in black
leather round toe with a three inch chunky heel and a pair of black patent
three inch stiletto heel and ankle strap. Mother said she had plenty of
handbags I could use to go with the outfits.
Next we bought several pairs of pantyhose in shades nude and black. Which
Mother assured me would cover the four outfits. We then went to an
underwear shop, where I was a little embarrassed, but soon relaxed when
Mother explained to the shop assistant
"My Son really did not want to come in here, because he would be embossed
whilst I was selecting 'unmentionables' for his Sister. But I assured him
no one would mind."
"Of course not, we will certainly not embarrass you," smiled the young
attractive sales assistant. Mother selected one white and one black bra in
size 34 (my size, as measured last night!) She then asked the assistant if
they had silicone bra inserts as her Daughter (Me!) wanted to look a size
B. The girl smiled and brought out the required inserts. Mother then went
to select some panties. I whispered in her ear that this was unnecessary,
as I had plenty for briefs at home.
"Remember 'totally immersed in the role', I think you said last night and
this is part of 'total immersion'." She smiled. She proceeded to select
three pairs each in black and white in different styles - all of them
padded and very sexy. To my horror, she finally added a baby doll nightie
with matching panties in pink, mouthing, "Total immersion," and smiling at
me. We then went to a cosmetic shop, where Mother purchased a whole array
of cosmetics, lipsticks, eye shadow, blusher, foundation, nail varnish and
various brushes and a lot of things I did not understand.
"Mother I haven't a clue what half these things are."
"Under my tuition, you will soon be an expert. I think that completes
everything we need as you can borrow any of my jewelry that you may need.
Just one thing, let's get your ears pierced as all my earrings are for
pierced ears. Your hair is long enough to cover your ears and hide the
studs and after the last performance of the play, you can stop wearing any
earrings and the holes will simply grow over."
"OK Mum, let's go for it." So twenty minutes later I had little gold studs
in my pierced ears.
When we got home, we unloaded all our purchases to my bedroom. To fit
everything in, Mother took everything except clothes I needed for school
and put them in the spare bedroom wardrobe, pointing out I would not need
any of them until the play had finished. Mother then wanted to see if all
the new garments fitted properly, so she made me strip and put on one of
the bras and panties. She showed me how to clip on a bra and I then
inserted the silicone inserts, it all felt a bit weird, but they fitted me
quite comfortably. I then tried on each of the four outfits; with Mother
fussing round seeing that they hung correctly, she finally pronounced
herself satisfied that everything fitted well on me. I then went for a
quick shower before putting on my jeans, T-shirt and loafers. I did note
that my pajamas had disappeared from my bed and been replaced with the pink
nightie.
At dinner Mother said she wanted me to take a long bath with oils that she
would give me and to shave all my body hair off.
"You don't do any sports this term at your request, so nobody will see what
you have done. Anyway, if they do you can tell them it is for your part in
the play. I will lay out an outfit for you to wear, whilst you are in the
bath and after breakfast. I will give you your first make up lesson and we
will see if we can make you look like a girl, before we teach you how to
act like a girl. Oh and let me manicure your nails now so that you don't
ladder your tights as you put them on."
She then went and got 'my' manicure set, purchased that morning and
proceeded to show me how to attend to my cuticles and then create a smooth
shape with an emery board, she finally rubbed in some cuticle cream and
some hand cream.
"Yours nails are too short at the moment for nail varnish, but you will let
them grow and soon we can see how pretty your hands look with painted
nails. You will need to constantly treat your nails and use the hand cream
to soften your hands, so they will look and feel ladylike," she said with a
smile.
"You really are enjoying this, aren't you?" I asked.
"Actually I can't wait to see you in full makeup and one of your outfits
on."
At bedtime I put on my baby doll with the matching panties. It felt strange
but actually very soft and comfortable. I slept well and awoke, slightly
disorientated in my new slumber wear but quickly recalled today
arrangements. I took Mother her usual early morning cup of coffee.
"You do look cute." She said with a grin. I gave her an exaggerated girly
wave and disappeared to my bathroom along with the goodies Mother wanted me
to add to my bath. Whilst the bath was running I shaved all my very spartan
hair, including my armpits and legs. I then shampooed my hair with Mother's
supply before wallowing in the perfumed bath. I then toweled myself down
and added conditioner to my hair before going into my bedroom where Mother
had laid out my outfit. I dressed in white panties and bra, adding the
silicone inserts. I then succeeded in putting on a pair of nude pantyhose,
without laddering them. I really like the feeling against my now smooth
legs; I then put on the floral printed dress and finally the chunky heeled
shoes. I had to walk around the room for some minutes to get used to
walking in heels. As soon as I was vaguely confident, I went to join Mother
in her bedroom and looked at myself in her full length mirror.
"That looks like a man with scruffy hair wearing a frock!" I said in
exasperation.
"Patience please," said Mother. "Wait until I have worked my magic."
She sat me down with my back to her dressing table and proceeded to
carefully blow dry my hair using brushes to shape it, or so it seemed to
me. She firstly plucked a few hairs from my eyebrows.
"Nothing serious, no one will notice, but it improves the shape."
I could not see what was going on, but first my whole face was treated,
then my cheekbones, followed by my eyebrows, eyelashes, eyelids and then I
was asked to purse my lips while lipstick was carefully applied and finally
to press my lips on a tissue to 'blot' my lipstick.
"Now go over to my full length mirror and see what you think" Mother
invited.
I walked over and was staggered at the transformation. There in front of
the mirror was a very pretty young woman.
"Mother, you are a brilliant artist. I cannot see any vestige of maleness
in front of me. Actually, I could really fancy this woman in the mirror."
We both laughed.
"That was the easy bit," said Mother. "I now have to teach you to walk and
gesture like a lady as well as how to do your own makeup and how to think
and act in a feminine manner. Your hair is not bad, but it is too short,
but with nearly three months to go before your play starts should be enough
time to get it to a reasonable length."
"I will need permission from school, as my hair is at maximum permitted
length now at my neckline. But I am sure Mr. Newton the tutor in charge of
the play will get exemption for me. I will ask him at our first rehearsal
on Tuesday.
We then went for breakfast and from then onwards I was bombarded by
directions from Mother. How to walk, how to sit down, how to get up, how to
hold my hands, how to use my arms, how to cross my legs when sitting, how
to express myself when talking and much more. The instructions were
endless, but I am a good learner and by early afternoon Mother
congratulated me on my progress. After lunch Mother suggested I see if
there was any tutorial on the internet to help me achieve a female voice. I
searched for the information and was amazed at the number of sites
available to assist transvestites achieve a feminine voice and much more
besides. I went to my bedroom and spent some time on a number of YouTube
sites learning and practicing a female voice, until I was satisfied that my
voice genuinely sounded like that of a woman. I then joined Mother in the
lounge.
"Would you like a cup of tea?" I asked in my female voice.
"I really thought I was hearing a girl then. Fantastic and in such a short
time, well done and yes I would love a cup of tea Miss and take shorter
steps when you are walking and remember what I said about arm movement." I
go and make the tea and concentrate really hard on all the instructions I
have been given. Mother and I sit in the lounge for a few hours discussing
general things, with me really concentrating really hard at being an
elegant lady.
"I suggest that we concentrate on one area at a time for your make up and
only move on when I am satisfied you have perfected each area," Mother
suggested. "Let's start with your foundation and blusher. Go and clear all
your makeup using the cleanser I have left in your bedroom and I will come
up and show you how to apply."
I am now feeling quite comfortable in the clothes I am wearing and getting
used to all the girlie movements. When I have cleared my make up Mother
comes up and carefully applies foundation and blusher, showing me what she
is doing step by step.
"Now it's your turn. Come down as soon as you feel you have got it right."
At about the sixth attempt, I came down and presented myself to Mother. She
made several suggestions, before agreeing we had done enough for the day. I
was instructed to come home from school tomorrow and change into the outfit
Mother had laid out and apply foundation and blusher.
The following evening, as soon as I got home, I changed into the female
underwear, nude pantyhose, printed dress and chunky heeled shoes. I then
applied the foundation and blusher. A couple of attempts and I was
satisfied with the look. I really concentrated on my gestures, the way I
walked and the way I talked. Mother was delighted but said I needed to work
on my hair.
On Tuesday we had the first rehearsal for the play, I explained to Mr.
Newton that I had recruited Mother to assist me develop the role and that
we had bought the outfits required for the play, I also asked for
permission to let my hair grow to enable the necessary styling required for
the role. He readily agreed to everything and was delighted at the way I
had thrown myself into the role. After rehearsals, he congratulated me on
appearing more ladylike than he expected and asked me to bring the receipts
for the four outfits that the school would reimburse.
Over the next month, I continued in the same routine, changing into one of
the character outfits as soon as I got home and gradually adding more and
more of the makeup until I could do everything with confidence. My nails
are long enough to paint and I am now confident in doing this myself. The
rehearsals are going well and everyone is impressed with the. "lady" in the
cast. As the weeks go by, I find I cannot wait to get home and change and
really love dressing, applying makeup and painting my nails at weekends. I
walk down to the village at the weekend and everyone addresses me as.
"Miss" which I find exciting that I must have mastered the female role. In
fact I find that during school time I have to really concentrate to avoid
girly gestures and using my girly voice.
On this particular weekend Mother is away overnight staying with a friend
and will not be back until Sunday afternoon. I decide to go into town to
get a new mobile phone. I wear the navy dress with the patent leather shoes
and nude pantyhose. I wear light makeup, but red nails. I am now so used to
heels that I am starting to feel uncomfortable in flats! The assistant at
the phone shop cannot do enough for me (I am certain he fancies this.
"girl") which amuses me, but also makes me realize the power of a pretty
girl. I am sure I got the best deal of the day by showing a bit too much
leg and gazing into his eyes as he explained the functions of the new
Smartphone. I am so pleased with everyone's obvious acceptance that I am
attractive and female; I go browsing through the ladies ware department at
the big department store in the shopping mall. I confess I am getting bored
with a wardrobe limited to four outfits, so I decide to spoil myself. I try
on a flared denim miniskirt, it is so short it hardly covers my panties,
but it is so nice and appropriate for a. "girl" of my age. So I buy it
together with a turtle neck knitted skinny rib top in black add a pair of
opaque black pantyhose and I have a teenager's outfit. On Sunday I have a
lazy day - long soak in my oiled and scented bath, I shave off the few body
hairs that show then shampoo and condition my hair before dressing in black
bra and panties, my new black top and mini skirt and finish off with the
black chunky heeled shoes. My bright red nails are fine and I then do all
my makeup, an operation I really enjoy. I apply foundation, blusher,
eyebrows, eye shadow, mascara, eyeliner and lipstick fairly light with a
reasonably natural look I am now quite competent in styling my (much)
longer hair, rollers, brushing out and contouring round my face. I add a
pair of big dangly earrings to complete my appearance. I look in Mother's
full length mirror and love the appearance of this pretty teenage girl.
When Mother gets home in the afternoon, I am in the lounge reading one of
her fashion magazines. She comes in and I rush up to her and give her a
girly hug.
"Wow," she laughs. "I thought I was training a 30+ business woman and I
come home to find a stunningly attractive teenager".
"I know I shouldn't, but I am getting bored with the mature outfits I need
for the play and decided I wanted to be a 'girl' my own age. I hope you
don't mind?"
"Of course not! I am just so delighted how you have really absorbed this
role in the school play."
Finally it is the week of the play. Before the dress rehearsal I go with
Mother to her hair stylist where I receive a really feminine hair style,
full wavy and cascading over my shoulders. Mother comes with me to dress
rehearsal and makes sure my makeup and particularly my hair is OK. This is
the first time any of the cast have seen my female outfits. Some are
surprised by my underwear. I laughingly explain Mother's 'Total Immersion'
philosophy. The dress rehearsal is OK and we all discuss the ways we can
improve the actual performances. The next three days we do the real
performances. These go down really well and on the final night we receive a
long standing ovation from the audience, I am pulled to the front at the
final curtain call to receive my own applause. I am so emotional I nearly
weep. After the last performance we have an end of show party at a nearby
pub. I go to the party in the LBD outfit from the play which causes some
surprise, but I explain I can hardly wear a suit and tie with bright red
nail varnish and my current hairstyle. Everyone accepts this and we have a
fabulous evening and end of term party and for many of us the end of school
life.
The following morning which is Saturday, I wake up late morning after the
party the night before. I get up take my usual bath towel down and slip on
my bra and panties before putting on my skinny rib black top, denim mini
and back opaque pantyhose with my chunky black shoes. I fuss with my hair
before applying just light makeup, my nails are still fine. I am just
applying my lipstick when I realize that the whole reason for me appearing
as a woman is over. I look in the mirror and decide that I like the way I
look and I am getting a lot of fun being a girl (remember the mobile phone
salesman!). I go downstairs and make a cup of coffee before joining Mother
in the lounge. She is surprised to see me in 'girly' attire.
"It seemed a shame to take off the nail varnish and what about the
expensive hairdo the other day. Besides I am having fun being a girl and
there is plenty of time before I go to Uni."
Mother laughs. "Fine by me, be my 'Daughter' as long as you like."
This was probably the moment I realized that I actually preferred this way
of dressing and I determined to continue with my current appearance, as
long as it had approval from Mother. The only way I could be certain of my
Mother's approval was to increase my feminine wardrobe and see if Mother
presented any objections. I wanted to be sure she actually approved of what
I was doing. So without telling Mother, I spent the next week gathering a
wardrobe for a very girlie teenager. Skirts, dresses, tops, blouses,
underwear, shoes, makeup, nail varnish, even perfume.
It is all in place now, I so hope Mother approves......
Anastasia
- 26.02.2022
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