A story about crossdressing – his is the beginning of a series of episodes about poor Charles who ultimately loses all his male attributes

It all began with a letter Charles received on Friday after
being home ill for a week with an undiagnosed lower
abdominal disturbance.

I had a nice chat with your wife Paula, the other day. We
both agreed that you need a new direction in your life to
help you stop playing this silly role-swapping game. She
tells me that she has once again caught you attempting to
wear some of her clothes. It is obvious that you cannot
make up your mind what you are and how you should behave.
Because of your insensitivity to Paula’s position it is
obvious that something must be done to prevent your doing
irreparable damage to her reputation and security. Since
you obviously are unwilling to take her situation into
consideration we must take charge of your life for you.

We’ve developed a plan to resolve every aspect of your
weakness once and for all. Your business partners have
already been notified that you won’t be into work anymore.
They received your letter of resignation from their
association and have accepted it with regret but as you
requested they will not attempt to meet or talk you out of
your decision. Your share of the partnership, which amounted
to over $100,000 has already be forwarded to Paula as you
“requested”. She has deposited it in her new account as
well as all funds from your joint account. You will
therefore be totally dependent on her good will and support
in order to live. She in turn believes that living off
someone else is inappropriate and that working for a living
is good for the soul.

Therefore, new employment more suited to your nature, has
already been arranged and will begin as soon as you are
appropriately prepared for it. The manager of the Sapphos
Beauty Salon has agreed to take you on as an apprentice in
their pedicure room. The Manager has been kind enough to
send over the new uniform you’ll be required to wear.

Charlotte is how you will forever henceforth be known both
legally and by everyone you meet. I know you’re going to
just adore the uniform. The cute little dress is all red
satin with a strapless low-cut bodice and a sassy little
full skirt. You’ll have to wear several short crinoline
petticoats to make it flare out properly. A lacy white
apron will highlight your new tiny waistline ever so
dramatically. Of course, we were at first concerned that it
would be too small at the waist for your figure, but with
the proper corseting, we know you’ll look exquisite even if
you are very uncomfortable and restricted in your movements
by the severity of the corset. The loveliest pair of
stockings was sent along with the outfit. Honey, they’re
black and very sheer with a seam running all the way up the
back to the prettiest lace tops. These will of course show
under your flared little skirt. She’s also sent some cute
little lacy anklets to wear over them.

You’re going to be just too sexy for words. You’ll just die
when you see the shoes you’re to wear. They’re red patent
leather and have the highest heels I have ever seen. They
must be at least 6″ with open toes and the most delicate
ankle straps. I can just see you in them now, forced to
mince about the salon so carefully to keep from falling.
That will be quite difficult and tiring for your legs at
first because the base of the heels is smaller than a pencil
eraser. You’ll have to learn to keep every muscle in your
buttocks, calves and ankles firmly in control just to even
walk. However the conditioning that will cause as a result
of your being in such heels for 10-12 hours a day will
develop a gorgeous fanny and beautiful feminine leg lines.

Now, because this salon has a very exclusive clientele, it’s
most important, dear, that you not embarrass us by
misbehaving. To insure this, we have worked out a strict
morning regimen to be followed the rest of your life. After
your morning exercise and walk, you’ll get to eat. However,
from now on there will be no more he-man breakfasts. Just
some toast and grapefruit perhaps. A little juice will be
permitted, if only to help you swallow the special Estanil
vitamins your wife has acquired for you. Then it will be up
to the dressing room where I’m afraid your wrists will have
to lashed to the lacing bar. This is of course to restrict
your movement while you’re being prepared for work each day.
You’ll be drawn up on your tippytoes so we might lace in
your corset a few more inches than what you’ve been used to
up till now. I know that you will love the ultimate 19 inch
waist which they require. For the first six months until
the Estanil really takes effect, that dirty little thing
between your legs will have a nylon cord loop attached to it
and this will be drawn up between your legs and hooked
tightly to the back of your corset. That way you will never
be able to get an erection and expose yourself.
Unfortunately, since it will now be pulled between your
thighs, your walking will probably keep the end so irritated
you’ll never be able to stop some feelings from entering
your mind, but you’ll not have to worry as there will be no
way to respond to them.

Of course your own lovely toes will be polished and buffed
whenever the polish needs redoing. Since you’ll never again
be allowed to have unpolished toes, this may have to be
redone weekly. Since they adore red as a part of their
basic Salon theme at the salon, you will use the brightest
and sexiest red colors at all times for your hands, toes and
lips. You have so admired my gorgeous long nails that you
will have porcelain nail covers, good for six months,
applied in 1 1/2 inch lengths as the very first action Paula
and I take. That will however make it almost impossible for
you to do much without our early help. In time, unless you
wish to be severely punished, you’ll learn to do everything
necessary despite the terribly long nails.

While you’re suspended it will be much easier to draw up
your beautiful new stockings as well. Whenever polish has to
changed or redone, it probably means you’ll be there for a
while each morning which will tend, over time, to elongate
and narrow your waistline as the muscles re-adjust
permanently. Of course the special medication, especially
the Estanil, will also change the distribution of body fat
particularly in your hips and abdomen. I’m sure you want
the stockings to go on correctly with the seams as straight
as possible. Next, you’ll be buckled into your lovely new
open toe pumps and the little gold padlocks, which are so
cute, will be fastened to keep them on all day. Then,
before we go further, your makeup will be applied while
you’re hanging so helplessly. We feel the extra time in
that position is very important to your figure development.
Special care will have to be taken with your lipstick,
eyeshadow, blusher, and false eyelashes so as not to give
away your secret to the ladies you’ll be servicing.

However, they will be most alluringly done as we want you to
be the source of admiration and for them to have great
desire for you and your lovely mouth. Some of these ladies
have a special appreciation for a pretty thing such as you
will certainly become. It will be very difficult for you to
maintain your dignity and behave yourself unless you
remember that Paula and the Manager strongly believe in
corporal punishment for misbehavior.

Of course your admiration for Paula’s earrings was well
known to us. As a part of your initial preparation we will
have your ears double pierced and little gold stud sets
placed in each hole in both ears. The lower stud sets
however, have a loop at the bottom so we will be able to
fasten those very large very heavy dangly earrings in them
for nightime. You have such trashy tastes in earrings that
it seems we should make you wear those that will really draw
attention to you. Perhaps you’ll learn the reason nice girls
don’t advertise so blatantly.

We’ve also acquired some special ointment to smooth into
your little breasts. Most certainly you are under developed
at this time. The label claims that in less than 30 days
they’ll swell out to be so soft and plump. Paula’s
gynecologist assures us that in combination with the Estanil
the desired effect will be easily achieved, unfortunately at
the cost of every aspect of your current disgusting
masculinity which will end forever.

To absolutely ensure the best results, however, and to
preclude any immodesty on your part for the next six months,
we’ve made the purchase of a very unique device. It looks
something like the milking machines you see on a dairyfarm,
and essentially, that’s what it is. It only has three
suction lines however. The main one’s purpose is obvious.
The other two have hemispherical attachments that will
attach to your budding bosom and will greatly enhance the
effect of the special ointment. Its pulsating pump and
light electrical stimulators, will not only beautify and
enlarge your sweet little breasts but the main line will
relentlessly drain you every morning of your nasty ungirlish
fluids. With the Estanil however, your little nipples will
become as tender as can be. Unfortunately you will
therefore be incredibly stimulated whenever you are on the
machine and you will know almost unbearable discomfort.
There is a fourth part to this unit which will be inserted
in your new “pussy” to stimulate you during the process both
for conditioning and to ensure that all your ungirlish
fluids become available for draining. In time there will be
no further generation of such fluids because all parts of
your body which do so now, will become useless and impotent.
However for the time being, that which is drained from you
will be replaced, through your new “pussy’ by using Premarin
ointment. You will thus become very used to a burst of
squishy fluid gushing into your body orifice every day.
Under this regimen you will naturally become more and more
docile. Your body shape will change completely and will
resemble Paula’s. How perfect- You’re going to look just
scrumptious and become so incredibly desirable. Our
program will insure that you are molded in both mind and
body to better suit your new situation.

I hope your new clients appreciate our efforts. As you
kneel at their feet to remove their panties and stockings,
not only, need they not fear any misbehavior, but I’m sure
the sight of such plump little breasts spilling over your
bodice will endear you to your customers. You’ll have to be
quite careful because this salon’s special customers just
love to tease a visible nipple and yours will be so
sensitive and easily responsive to painful pinches.
Unfortunately, your new work uniform does little to shield
even your current tiny bust from such attention. As your
bust grows they will not change your uniform. They just love
a very very busty look and as such you’ll have to suffer the
consequences more and more every day.

Who knows, after polishing and buffing a customer’s toenails
as they sit before you; after replacing their gossamer
nylons and exquisitely high-heeled sandals, you may be
rewarded with something more than a few dollars as a tip.
If one day you feel a beautifully nailed hand on the nape of
your lovely neck forcing you forward toward her womanhood;
if as you lap at the nectar-filled fountain between her
nylon encased thighs, you think of us with a heart filled
with happiness and gratitude, we will have done our job.

Best of all you will begin to want and need the feel and
taste of a male organ. Soon that desire will become almost
uncontrollable because your original sexual emotions will
have been totally replaced. So that you may properly earn
additional money to support your new clothes habits and
personal needs, I have arranged for a very special escort
service to offer your services to that selected group of
very dominant men who love to have an expensive and stunning
looking but orally satisfying she-male complete their
evenings entertainment. As such you will be busy all day and
then for many evenings you will be learning about fulfilling
all the many demands that men place on women. I am sure
that you will develop many talented capabilities centering
around your mouth and ultimately your new “pussy”. In all
of these cases, however, you will be in great physical
danger if you do not do exactly as your “companion” wishes
no matter how repulsive and disgusting it may seem. I will
think of you often over the coming months and I will be
pleased at how helpful I have been to you and Paula.

Your loving sister:

Kay

The panic set in as Charles realized he was trapped. Fear
flooded his mind and he began to shake. As he put down the
letter he began to feel nauseous again and passed out little
realizing that his wife had been feeding him special
medicine all week..

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