Corporate Ambitions

By Ashley and Sarah

Prologue

As I relate this account of my incredible reversal of purpose, I cannot avoid a 
confused mix of emotions when I realize the clarity of my own recollection.  
It cannot be that it was so short a time ago that my passions were focused in 
quite another direction.  Indeed, it seems a lifetime ago when my resolve was 
to be what I am fond of thinking of as "the other".

I was a graduating MBA, mature but still somewhat young, and ready to 
launch what I knew would certainly be a "go-getter" career.  I was graduating 
near the top of my class from a well-known "B" school, as we in the 
business world call such institutions.  I was enthusiastic about my future, and 
to paraphrase a popular rock song, "My future was so bright, I had to wear 
shades."

The time for interviews with prospective new employers had arrived, and I 
was quite sure of what would happen.  You see, I had put my social life on 
hold, put my nose to the grindstone, even laid out big dough to get here.  All 
to be in a position to choose instead of being chosen.  Now it was payday, 
and things would be different from now on!  

I would not take a job with one of those blue chip corporations only to start 
as "associate something or other."  No way!  I would pick a company that 
would start me near the top, and it would be up from there.  AND, I would 
leave a trail of tragic female conquests in my wake as I rose ever surely to the 
top of the firm lucky enough to have me ultimately as their CEO.

Given my current circumstances, such ideas seem completely foolish to me 
now.

My name is Heather Williams.  I am the personal assistant to Rebecca 
Williams, the CEO of Women's World, LTD., a major corporation catering 
to women's fashion, cosmetics, lingerie, and such other needs as girls do 
enjoy.  Rebecca has instructed me to write this story as part of my duties in 
my new job.  A job that will be, I'm at once afraid and happy to say, is the 
pinnacle of my success.  

As I sit here typing this I am dressed in my usual style of work clothes: 
a short, tight, satin dress in red with dark silk hose 
reaching up my legs from 4" stiletto heels.  My make-up is done to 
perfection, and the lingerie under my dress is satin and is simply exquisite.  

You see, there is a dress code here at Women's World, and all we executive 
assistants are required to abide by it.  We are expected to portray the image of 
absolute femininity at all times.  Rebecca and our relationship are unique in 
that she is my Boss, my Mistress, and yes, I am her Wife.  In truth, I am a 
now a submissive transvestite slave to her.   I'm sure you are wondering how 
I let this happen to me. Let me explain ...

Chapter One

I Gotta Wear Shades

During my initial interviews with several large corporations, I was intrigued 
most by Women's World.  The position being offered was executive assistant 
to the CEO.  Talk about starting right up there!  The idea of working directly 
with a CEO, along with a generous compensation and relocation package was 
more than I could resist.  I shrewdly figured that working directly with the 
CEO would put me on the fast track to the top.  I put a very good effort into 
this particular interview, and it seemed to pay off.

Doris, the interviewer for Women's World was quite charming.  I figured her 
for the Human Resources Dept. Director and not one of those paid recruiters.  
She seemed to know everything about Women's World, and I asked a lot of 
questions, priding myself on interviewing my interviewer.  But I could not 
get a read on this one.  Nothing I could put my finger on, but at times I swear 
I caught Doris trying to hide a smirk.  Finally, Doris left me with a few 
encouraging words and a very large packet of material for me to fill out and 
send back to her.  She said she felt fairly confident she could get my 
application "in front of" R. Williams, the CEO and, in this case, hiring 
manager.

I had nothing keeping me in "B" school town.  No wife, no romantic 
interests, no more promising prospects, so I said, "What the hey." I filled out 
and sent the information called for in the hefty package Doris had given me.  I 
wasn't really surprised by the voluminous pre-employment miles of 
paperwork, given the position being offered.  But I was a little curious about 
the requirement to include several photographs, and the specific emphasis on 
at least one full body shot.  I just shrugged and thought, "Probably too many 
guys wearing jeans and sneakers while looking all business-like from the 
waist up."

I wasn't expecting a response for a certainty, and when I received an e-mail 
directly from R. Williams/CEO I was somewhat surprised.  The e-mail 
explained that my employment package was "impressive", and asked me to 
respond with a time that would be good for me to discuss the position 
available.  

My mind was reeling, as were my thoughts of even better chances 
of moving up the ladder fast.  I e-mailed my reply immediately and set up a 
time for the call the next morning, if he could put me on his calendar then.  

"She" responded within an hour advising me of the time for our 
"teleconference".  I was a little embarrassed to learn only then that R. 
Williams was a Ms. Rebecca Williams.  

I can remember thinking, "Hmmm, this is going to be easier than I thought!"

The next morning the phone rang at the appointed time, and I nearly jumped 
out of my skin.  I tried desperately not to sound nervous answering, being 
somewhat unprepared at such an early hour.  But it only took seconds for her 
to put me at complete ease.  Her voice was very soothing yet intensely 
commanding, as she led the conversation precisely where she wanted it to go.  
It seemed like only a few moments but it had been nearly an hour since we 
had begun talking and I was accepting her invitation to go to Florida for a 
second interview.  

The real kicker was that she had a corporate jet in town for business and 
offered me a free "hop" if I could go the next day.  I was packed and out 
the door the next morning at the crack of dawn, heading for a private 
section of the airport.  I was certain I was headed for greatness!

The plane ride was rather uneventful, but it was the first time I had ever been 
on a Lear jet.  My mind concentrated on the future that lay ahead, and my 
visions of grandeur were, to me, pragmatic and clear.  I would land this job, 
then work myself into the graces of this Ms. Williams until I would be the 
new CEO.  It seemed like only minutes but it was actually 2 hours till we 
were landing at a small private airport in Florida.  

The first of many pleasant surprises awaited me when I stepped off the plane 
and saw a limousine waiting to drive me to my hotel.  Even more pleasant 
was the chauffeur, who had to be the most beautiful woman I had ever seen.  
Tall, blonde and gorgeous!  The leather riding pants she wore made no effort 
to hide the most luscious derriere I had ever seen, and her black satin blouse 
likewise showed off a pair of beautiful breasts to their utmost.  I knew I 
would love to spend time with this woman.  

Yet, like Rebecca, she was at the same time soft spoken and still somehow very direct.  
She welcomed me and held the door for me.  "Nice touch," I thought as she sped us to my 
hotel in the powerful car.  At the hotel, she opened the door for me once more, and 
told me she would meet me in the lobby the following morning at 8am sharp.  

Her face changed a little when she said in a voice that betrayed a hundred 
times, "Please try and not be late!  Ms. Williams is irritated easily by 
tardiness."  With that she was off, leaving me with a vision of her cute, 
wiggling ass and many female conquests that were yet to come.  As I 
watched the way she moved, my eyes glued to her ass, I joked to myself, 
"Hmmm, two Volkswagen Beatles vainly trying to pass each other on the 
Freeway."

I entered my room still wearing the self satisfied smile to find a chilled bottle 
of wine and a welcome note from Women's World that enthused how 
looking forward to meeting me they all were.  "I could get used to this," I 
quipped out loud, as I stripped to my jockeys.  I sat down and started going 
through the Dunn and Bradstreet report on Women's World, ticker symbol 
Ww (boy they had been around a long time).  I had brought piles of reports 
with me on this company.  I wanted to ensure I was really prepared for this 
interview.  The more I learned about this company, the more intrigued I 
became.  They were an acquisition company, but with a focus, it seemed.  I 
was just piecing it together when the day caught up with me and I fell sound 
asleep.  

I was up at the crack of dawn, shaved, showered and in my best, neatly 
pressed Brook's Brother's suit.  While waiting in the lobby for the limo to 
pick me up, I garnered all the enthusiasm I could muster.  The limo arrived at 
precisely 8 and I was pleasantly surprised to see that my gorgeous blond 
chauffeur, Janie, had traded in her riding pants for a short, tight, leather mini-
skirt. Talk about legs, this woman had some of the most gorgeous legs I had 
ever seen.  I could only imagine where they lead.  I figured she might well be 
my first conquest!  Janie was the epitome of sexy and I was disappointed 
when we'd arrived at the offices of Women's World so quickly!

We pulled into the sprawling Women's World headquarters campus at just 
8:30, and Janie escorted me to the lobby.  The building was rather 
unassuming for a Fortune 500 company, but that was nothing compared to 
the inside.  It was very obvious from the dˇcor that this business was owned 
by and catered to women.  There were light pastel colors and everything was 
so very "pretty".  I remember thinking how I would change it once it 
belonged to me.  The thing that threw me most, though, was that there didn't 
appear to be any men working there.  Again, I was smirking.  "Oh yes, this 
is going to be easier than I thought."

The area opened into a kind of bullpen, with secretaries sitting in the middle, 
and offices around the perimeter.  And, the women were all so beautiful.  
"My dumb luck," I mused, "to stumble into such riches."  As the secretaries 
milled around, not one of them wore anything but a nicely tight, short mini-
skirt, showing off their long, luxurious legs, which of course descended into 
sexy high heels.  Wow!

Everyone from the receptionist to the secretaries was attired thus.  I was 
totally absorbed in a vision of all the fun and "bennies" I was going to have at 
this job.  Just then, the receptionist snapped me from my reverie telling me in 
a stern voice, "Ms. Williams will see you now."

I snapped out of it, shook my head, and focused once again, walking into her 
office.  It was like any other CEO's office. Plush and very comfortable, with 
a singular exception... its decor was very feminine.  Then the tall, leather 
armchair behind the desk turned around and I saw Ms. Williams for the first 
time!  She stood to shake my hand firmly, and I had trouble making the 
words come out of my mouth.  She was stunningly beautiful!  She was 
wearing "the" classic, tailored, woman's business suit.  While it was a suit, it 
remained somehow sternly feminine, if there can be such a phrase.  It was all 
business, but still highlighted her charms to the maximum!  I made her 
somewhere between the age of 35 and 40, close to my age, if perhaps a bit 
more sophisticated.

And it was obvious that she took very good care of herself.  No single 
word superlative I can think of to describes her combination of beauty and 
demeanor adequately.  Statuesque, perhaps, comes close. 

I needed to remind myself to breathe!

Taking the lead, she offered me a chair as she began.  Just as on the phone, 
her voice was soothingly disarming.  She had me at ease in an instant, with 
her easy charm.  She asked me questions about my education, where I came 
from, and my career ambitions.  She also told me a little bit about her 
company, most of which, I already knew.

About half an hour into our interview she was called from the office on an 
emergency, and as she left, she told me to make myself at home and to check 
out "the surroundings."  I could not resist.  I got up and began looking 
around the plush office, thinking, "Someday it will be mine, all mine!"  

Walking to a table with some open boxes sitting on it, I saw what had to be 
some of the most beautiful lingerie ever conceived.  "These must be some 
samples from one of the manufacturers," I mused, holding the dainty things 
up to the sunlight.  I could just imagine what my chauffeur, or any of the 
secretaries for that matter, would look like in this lingerie.  And even more 
so, Ms. Williams!  

I continued my explorations and picked up a pair of pink, satin panties and 
while admiring them, suddenly felt her standing right beside 
me!  I dropped the panties immediately, blushing a bit.  Ms. Williams, or 
Rebecca, as she had asked me to call her, laughed lightly and said, "Not to 
worry dear, we are in the lingerie business and know precisely how lovely 
these things are.  You'd be surprised how many men we sell that kind of 
thing to."  I stuttered my disbelief's and went back to my chair, scowling.

Rebecca went back around her chair, and while standing behind it, smiled 
down at me.  She took the back of the big, leather chair in her hands and 
asked in a disturbingly matter of fact voice, if I believed that men would buy 
such pretty things to wear themselves?  I spat involuntarily that I couldn't 
believe it!  She just looked at me quizzically and replied, "You would be 
surprised with the number of orders we send to P.O. boxes with addresses to 
only a first initial and last name.  We've done some research and found that 
most of these orders are from men who want to remain anonymous.  Now 
why do you suppose that is?  We could care less, of course.  Business is 
business, no matter who buys!  As a matter of fact, I bet you would be 
extremely turned on if you would slide a pair of our silky panties up your 
thighs and around your waist!"  

I stammered that I most certainly would not!

She looked at me with a wry smile and continued, "I'll tell you what, Mr. 
Smith."  She said it with a touch of cynicism in her voice, "I have reviewed 
your resume and references quite thoroughly and I am impressed.  However, 
I am still not convinced you are cut out for a business career with this 
particular company.  What say lets make a little wager?"  

"Wager?" I stammered.  "Yes, just a little wager.  Since you seem to doubt 
my word about men buying and wearing panties like those pretty, pink, satin 
ones you, yourself were admiring, and since I can't afford to have an 
assistant working for me who doubts my word on anything, lets make a little 
wager.  I want you to take a pair of our panties and go into my bathroom and 
put them on.  If you are not aroused by the soft satin, I will give you a check 
for $50,000.00 and send you back home on my jet at my expense.  But if 
you become aroused, you will work for me for an entire week, learning my 
business and doing exactly as I say.  And..." she looked thoughtfully at me 
before finishing, "You will wear panties under your Brooks Brothers suits 
the whole time!  At the end of a week, if you have proven to me that you no 
longer doubt my word; that you can without hesitation do what I ask, and we 
both agree on it, I will offer you the job as my executive assistant.  The pay is 
$150,000 a year to start, plus benefits, plus relocation package."

"To make the bet even sweeter, if you do win, I will give you two nights 
with my gorgeous chauffeur, Janie.  I know you liked what you saw, you are 
a normal man right?  And every normal man lusts after that beauty.  Well?  
What do you say Mr. Smith?  Oh and by the way, I won't watch you change.  
You can lock the door and after you change you will come back out into my 
office and sit with me chatting for a half hour before the decision about your 
arousal is made, if it takes that long," she snickered.

Then she came around from behind her chair and settled back into it, looking 
at me with an evil grin.  I just sat there thinking.  Why not take this bet?  I 
may not get the job, but $50 K free money and a ride back home, and most of 
all, two nights with that gorgeous babe chauffeur!  I couldn't lose!  Look at it 
as a paid gambling trip where I got $50K and laid to boot.  I could do this, it 
would be easy!  I looked at Rebecca and choking back a laugh, said, "You're 
on!  I'd like my $50,000 in cash please."  

I expected Rebecca to get up and hand me the satin panties I was admiring 
before.  Instead, she pulled open a desk drawer.  I will never forget my 
chagrin as long as I live.  She pulled out the prettiest panties I had ever laid 
eyes on!  They were pink, and all satin with big ruffles at the waist and legs 
openings, and tied on with satin ribbons.  This meant that I would actually 
have to work at putting them on.  Not just sliding a garment up my legs, but I 
would have to tie bows at my hips.

As she handed them to me, she firmly restated that I had 3 minutes to get the 
panties on and be back in her office with nothing around my waist and crotch 
but the panties.  Her eyes were mocking, while I realized I hadn't noticed 
before how tall she was.  She rose from her chair, and pulling herself to her 
full height, held the mischievous garment daintily between her thumbs and 
forefingers, tauntingly.  

The expression on her face said that it was not her practice to hold panties in such 
a way.

I indignantly snatched the panties out of her grasp and headed to the adjoining 
bathroom thinking, "This is the easiest 50 thou I would ever make!  Closing 
the door, I took my pants and socks off, then came my Jockeys.  I held the 
panties up and then tied bows where I thought they should go.  Then I just 
stepped into them, pulled them up my legs and began settling them into my 
crotch.  Turning around and looking in the mirror, my pride suddenly 
vanished as I felt and saw my cock begin to rise of its own accord, filling out 
the front of the panties.  I panicked!  I grabbed my cock and squeezed it hard, 
trying to make it subside.  All this did was to arouse me more.  What was I 
going to do?  I had only three minutes to be out or I would lose, but going 
out like this was a sure loss also.  What would I do?

Fussing with the infernal satin straps at my hips, I'm afraid I wasted a lot of 
the precious three minutes.  As Ms. Williams knocked at the door I knew my 
three minutes were up!

"You can either show me you're not turned on, or admit defeat," came 
Rebecca's voice from the other side of the door.  "Well?  Was I right or not?" 
the impatient voice insisted.  Her tone made it clear she already knew the 
answer, and seemed to drip smugness.  I had never been so humiliated!  I 
was trapped!  I could not show her my now raging hard-on, and I certainly 
wasn't going to give her the satisfaction of seeing me with the ruffly panty 
tied across my ass with a big bow at each hip, no less!  "OK, you win," I 
admitted.  I wished my voice were not quite so sheepish.

"Get out here, Heath!  Or is it Heather, now?!" she mocked.  "OK, so I lost 
the bet," I confessed, as I hurriedly pulled my pants on.  I was so flustered; I 
didn't know what to do.  I hesitated, took a breath, then finally opened the 
door and came out.  I tried hard to look casual about the whole thing.

"The terms of our little wager were for you to show me how you are not 
turned on by the feminine lingerie this company sells.  I hope I have made a 
point, 'Mr. Smith,'" she chided with a particularly sarcastic emphasis on her 
use of the masculine title.  I knew it could be a long time before I would get a 
respectful "Mr. Smith" out of her again.  

Rebecca continued, "We sell these things to make money!  As CEO, I care a 
lot about our bottom line.  But I think you are a good sport!  Welcome 
aboard, you're hired!"

I was embarrassed and thrilled all at the same time.  Red faced to have been 
maneuvered into making the silly bet, and losing!  Thrilled to be offered this 
kind of money and a position so near the top of a big company.  But I was 
still wearing those teasing panties under my pants.  My still stiffening cock 
strained hopelessly against its satin crotch, making the elasticized leg 
openings tighten a little more across my ass.  Oh, I was more aware of my 
ass than I had ever been in my life.  Finally I offered, "I will accept the job on 
the condition that you release me from the consequences of our wager."

Rebecca's face grew into an exaggerated look of pretended dismay.  "A bet's 
a bet," she smiled knowingly.  "You wouldn't welch on a bet, would you?  I 
expect you to be properly pantied for the rest of the week, and I want no lip 
about it!  These terms of our wager you agreed to separately, and my offer of 
EA stands on its own.  Have we a deal, then?"  She stood with her hand 
outstretched.  A lifetime seemed to pass before I returned the handshake- her 
grasp was firm, and the deal was done!

"Good," she said as though dismissing me.  "Now get down to lingerie 
manufacturing and pick yourself seven or so pairs of panties.  I can't have 
my EA wearing the same panties all week long, now can I?"  I was horrified!  
"ME?" I eeked.  "Me get panties?   I have to do it?"

"Yes, and by the way, we'll be having dinner tonight, say around 8," she 
said flatly while writing something into her appointment book.  Then, 
looking up from her desk, "Is there something else?"

"No, ma'am," I heard myself say.  Where was the lingerie factory?

Chapter Two

From Shades to Panties

 I had been hired, and pantied all in a matter of mere minutes.  What was 
going on?  Was this Women's World company getting the better of me?  Me, 
the big MBA, who would certainly turn the business world on its ear?  I was 
sure I was ready to take charge in business, but in the course of events I had 
been given a first assignment to get myself panties from a lingerie 
manufacturing plant!  Where was our lingerie manufacturing plant, anyway?  
And what about my office?

I quickly called Doris in HR, and explained that I was accepting a position 
with the firm.  I threw in, for the benefit of my damaged male ego, "If you 
have any questions about it, please speak to R. Williams!"  I was so macho!  
"That'll carry some weight," I thought.

Doris kept breaking off, seeming to have someone else on another line.  
There must have been something terribly amusing going on in that other 
conversation, she kept chuckling every time she came back.  "Where is my 
office, anyway?" I asked, irritated with all the interruptions and giggling.  
"And where is our lingerie factory, I have an assignment there."  

Doris let me regain my composure before she hit me with the next 
bombshell...  "We'll take care of your office when you get back.  And the 
lingerie factory is in Paris!"  Damn her laughter!  "If you get the Concorde, 
you have just enough time to do your 'assignment' and get back in time for 
dinner with Ms. Williams."

"How did you know about that?!" I demanded.  Doris just told me to get 
down to the street, that the car was waiting for me.  I could not believe this 
was happening but I had to go through with it.

When I got to the street, sure enough, there was Janie, waiting in the long, 
sleek Limo.  It was comforting to see her now familiar face.  To my surprise, 
she seemed to know all about things.  "That's a good girl," I thought to 
myself as she rambled on about how I could walk right onto the Concorde, 
all the arrangements had been made.  "First class, of course, Mr. Smith."

Again emboldened, I threw my body over the seat to sit next to Janie as she 
sped us to the airport.  God, she looked hot!  Janie had legs that went from 
here to there and back again!  I couldn't stop myself from putting my hand on 
her helpless right leg, which was busy working the pedals of the car.  That 
long leg, encased in black nylon was just begging to be stroked, I thought.  
When she let her already too short skirt ride up like that, I took it as an 
invitation.  Pretty soon she was moaning softly, and I felt better.  My 
manhood restored, we had arrived at the airport.

The Women's World corporate jet landed in New York City and the transfer 
to the supersonic Concorde, true to its nature, was very quick.  It was as 
though they were waiting for me.  I was surprised at how small and cramped 
the Concorde really is, even in first class.  But the trip was fast, and I was 
still recovering from the events of the day, when we touched down in Paris! 
Women's World, also true to style, had a waiting Janie counterpart in Paris to 
whisk me away.  "All this, just for panties?" I mused.  "Certainly, it's 
Rebecca's way of showing me the international side of the business.  A 
business that will soon be mine!"

Toni was Janie's European counterpart, and she picked up right where Janie 
left off.  Legs to die for, and I put myself in the front seat next to her like I 
had been doing it all my life.  Pretty soon, I had my hand on her leg, too.  
Toni didn't speak English very well, so I forgave her for constantly referring 
to me as Ms. Smith whenever she asked me to stop that.  It was only when I 
thought about whipping out the hard proof of my manhood that I remembered 
about the frilly panties I was wearing.  I had stop, but there would be others 
like her, I thought, many others.

I wasn't sure what I was supposed to do, business wise, at the lingerie 
factory, but I supposed I would just look cool and figure it out from there.  
Meanwhile, I would pick up a few things to satisfy my bet with Rebecca.  I 
was determined to pay the debt, and definitely to get her back someday.  She 
would be surprised when I pulled a coupe and took over her company!

I thanked Toni for the ride and for holding the door for me as I went in.  All 
the while I was thinking, "Once I get out of these panties, baby, look out!"  
Now I had two, no three female conquests in mind.  Two chauffeurs and one 
CEO.  How easy in the case of the former; how appropriate in the case of the 
latter.

Women's World, Paris, LLC, was impressive.  I was received by a gaggle of 
girls all dressed in the cutest French maid's uniforms I had ever seen.  Pretty, 
black, satin edged with the daintiest lace at the bodice, sleeves and hems.  
Their little poofy skirts were all pushed out by unthinkable volumes of 
petticoats: all there to show off some very well shaped legs, which were 
encased in the most elegant, sheer, black nylon stockings.  Just out of view, 
those stockings were being drawn taught by the black satin garters that surely 
were there.

"You have a nice flight, Ms. Smith?  Lunch time now, no?"  Not another 
one!  But, they began serving me like a king, so I decided to let their 
insubordination go.  But I made a mental note of it.  Finishing lunch, I 
copped a few feels of the servant girl's cute asses.  They seemed even to 
enjoy it and did not discourage me in any way.  I was constantly reminded, 
though, of the cursed feminine panties that I myself wore beneath my male 
clothes.  I would have to make sure to pick up some samples here, to satisfy 
my bet with Rebecca.  How I began to hate that bet!

Lunch over, it was time for my tour of the Paris plant.

Chapter Three

Rude Awakening

 Women's World might have been run by Rebecca, but the Paris plant sure as 
hell was run by Magdalene.  Magdalene was a very stern looking woman.  
The minute she showed up, all the other girls pulled the plates and glasses off 
my table so fast it almost made my nose bleed.  Lunch was over, all right.

Magdalene introduced herself as the head of the shop, here in Paris.  Maggie, 
as she insisted I call her, was clearly in charge of this place.  "We, here at the 
lingerie manufacturing facility of Women's World," she prided with 
unmistakable authority, "know exactly what the men want.  We cater to those 
wants, and our margin has improved by orders of magnitude.  Your boss and 
mine, Rebecca Williams, knows how to market and knows what sells.  She 
tells us what to make, and we make it very well with the inexpensive labor 
available to us.  Now put this on so we can tour the shop!"

Maggie was handing me a set of shop clothes, very similar to the ones she 
wore, and all the workers wore, as I could see from the vantage point of the 
window I now peered through.  When she still stood there, I explained that I 
would be happy to wear the standard clothes of the shop floor, but that I 
would appreciate a little privacy.

With that, Magdalene gave me such a look!  She seemed to look right through 
my clothes-did she know?  Impossible!  Thankfully, Maggie left me to put on 
the shop uniform.  

I pulled the pants on and was surprised to find that the zipper was in the 
back, and to make matters worse they were made of a lycra type material, 
almost satin, and the color was a medium shade of pink.  It made me even 
more frustrated, if that were possible, to think how only girl's pants zip in the 
back!  My male ego told me, "Well, at least I was still wearing pants!"  Then, 
I pulled the top over my head, it was also of a very girlish style - puffed, 
short sleeves, loose at the top and hugging at the waist.  "I can't wear this!" I 
said out loud, as Maggie came into the room.

"Come on!" she urged, "You need to be back in New York tonight for dinner 
with Ms. R. Williams!"  Tugging me by the arm, Maggie dragged me out 
wearing this poofy, girlish uniform.  My panty lines were very obvious to 
anyone who cared to look at my ass!  I was mortified!

But soon, Maggie was showing me the labor that went into making the sexy 
lingerie that I had always believed was a silly thing that only girls liked.  
"Silly girls who I would conquer would wear such things for me!" I 
reasoned.  But now, I would be wearing them for a whole week!  "The bet!" 
I remembered.  As we passed by the sewing stations, I picked up a few 
sample pairs, trying not to look at them too closely.

I could not wait for the end of the tour of the shop.  Being dressed this way, 
and following Magdalene like I was her puppy was getting my goat.  But the 
place was loaded with pretty girls, all making fabulous lingerie by hand.  
They seemed to love their work, each one taking such care to get everything 
perfect.  Fussing with the expensive patterned material to get every seam just 
right, they were, every one, perfectionists.  I could not help but be impressed 
with this Women's World Company I had joined, but there was no way this 
was "inexpensive" labor.  Any one of these girls could have been a model 
herself!

Maggie explained the operation, while copping an occasional feel of my 
pantied ass.  She seemed to do it whenever she was sure someone was 
looking, which unnerved me a little.  I couldn't blame her for being attracted 
to me, but did she have to be such an exhibitionist?  Still, somehow it was 
turning me on.  At one point during the tour she was behind me and she 
grabbed my waist and leaned her crotch tightly into my panty and Lycra 
covered ass, much to the amusement of several girls who were watching.  At 
last, the tour was ended, and we were back at its starting point.

I asked Maggie where my clothes were, anxious to change back and get 
going.  Maggie gave me a real strange look, then.  "Want your clothes, 
girlie?" she asked with a growing smirk.  I just stood there in disbelief.  
"What did you say?" I shot back!

"Do I have to spell it out for you?  A real man would never allow himself to 
be pantied and dressed as you are now," she said in disgust.  She put a 
special emphasis on her unusual use of that word as a verb, "pantied".  I 
nearly swooned, trying desperately to keep my head.  I was now separated 
from all of my male clothes.  Maggie was clearly enjoying this as the 
realization of my situation sunk in- then she pushed hard against my body, 
shoving me into a wall.  I was unable to resist her strength.  That was when 
she pinched my nipple hard!  I should have said ouch!  I'm afraid I let a soft 
moan escape my lips and visibly weakened.  God, I was so hot!  When I was 
able to breathe again, all that came out of my mouth was "What are you 
doing?!  Where are my clothes!"

Maggie withdrew, and with a smile that belied experience, she said, "You 
little sissy!  You like it, you pantywaist!  You want to be a sissy?  Where are 
your clothes, girlie?!" she jeered.

Then she looked behind her, and I knew something was terribly wrong.  As 
my eyes focused, there on a table were the clothes of the fifi maids who had 
served me lunch!

"Hurry up, sissy!  You have about 14 minutes to put that on!  Move!"  I wish 
I could tell you I had the will to resist, but somehow, I was rendered 
submissive by the events of this particular day.  I was in a foreign country, 
and alternately being ravished and yelled at.  Discretion is the better part of 
valor, so I decided to do as I was told if only to get back to America.  Then I 
would be in control again.

Maggie made to strip out of the shop uniform right in front of her.  Right 
down to the ultra-feminine panties that I had obviously been wearing when 
I'd arrived.  With Maggie watching, my growing cock was giving me away 
again, the disloyal thing!  Was that a cell phone she was on?  She gave me 
some wolf whistles when I started dressing in the maid's costume, and I 
deeply resenting her watching.  I wondered if I were secretly thrilling to do 
what I was now being forced to do.  There was no mistaking, or hiding for 
that matter, my state of arousal.

"Move, I want to see a big, strong man become a sissy!" Maggie insisted, 
with an all too sinister sneer on her face.  First came the black satin garter 
belt, the one I knew was under the maid girl's dresses who had served me 
only minutes before.  As I snapped the garter belt's snaps behind me, I 
wished I could hide my telltale engorged cock!  I rolled the heavy, black 
nylon stockings up one leg, then the other, finally snapping the clever little 
garter devices into place.  These stockings were thankfully heavier than the 
sheer ones the maid girls had worn, effectively making my hairy legs look 
smooth.  I had the feeling that Maggie would have shaved my legs, 
otherwise.

I put my arms through the black satin bra, but by now my hands were 
shaking.  I was actually grateful when Maggie pulled it taught behind me and 
hooked it.  She then placed some breast forms into the bra, they must have 
been at least 38 D's, and I could no longer see my feet.

She took over pretty much then, and floated a soft, black, camisole over my 
head.  The cool, satin material made me shiver as it floated gently down my 
torso and settled over my now bra'd bust.  "You want this, don't you, 
sissy?" she smirked.  "What's that?  I can't hear you," Maggie was now 
yelling in my ear.  I was so tormented, I forgave myself as I answered 
meekly, "Yes, Ma'am!"

"Good girl!" Maggie bubbled with glee.  "We have just enough time."  She 
picked up the voluminous white crinoline petticoat and started stroking my 
raging hard cock with it through the panties.  "Why don't you put on your 
heels, dear?  If you agree to be a good girl, I might even give you a special 
surprise."  I was so hot I would do about anything for my imagined surprise- 
so I put on the high heels and even took the petticoats from her inviting hand 
and slid the feminizing garment up to my "girl" waist.  Oooohh, how I loved 
the feel of it on.  Things began to take on an aura of the unreal.

"Good girl!" Maggie was now openly laughing at me, and several other girls 
from the plant had come in, their shift seemingly ended.  I didn't care!  I was 
so hot, I would have done about anything for my "special surprise"!

"Tell all these girls how you like our products, then!  Tell them, what you are 
and what you like!"  Maggie demanded.

"I'm, uh, a sissy," I was saying.  I couldn't believe it was me as I continued, 
"I like to wear pretty, girlie panties.  Thank you ever so much for the 
samples."  With that, most of the girls giggled, some just nodded.  I thought 
I saw some high fiving one another.

"Are you ready for your surprise, Mr. Smith," I heard Maggie say?  My 
torture, I hoped, was over.  "Yes, since you have been such a good little girl, 
you may wear your new uniform all the way home.  Won't Ms. Williams be 
pleased when she sees how willingly you accept your new status in life!  
Who knows?  Maybe she'll even send you back to us."

As the girls looked on, tittering, Maggie held out the dress!  I pulled my 
wobbly arms though the puff of satin sleeves and the all too short dress 
floated down my body and settled delightfully over the frilly petticoat.  
Maggie said while zipping the back, "Time for you to go home, pet!  But 
first..." she turned took something from one of the tittering girls.

"Now for your surprise," Maggie delighted, pulling a cute short wig onto my 
head.  She fussed with it for way too long and to my horror, I realized she 
was tying dozens of tiny pink ribbons into bows in my new feminine hair.

I was astounded and panicky.  I would have to go home like this?!  How 
would I explain?  What if someone saw me?  I was ever more embarrassed to 
remember that I had to walk back to Toni's car.  I nearly fell on my ass 
walking in high heels for the first time, and I had no idea of what to do with 
my hands.  Each time I put my hands naturally at my sides, they fell on the 
soft, cool pile of the satin dress encircling my waist, the dress being held out 
by the scads of crinoline petticoat.  Each time, my male sensibilities made me 
draw my hands back involuntarily.  There was nowhere for them to go!

Maggie explained that I must take very short steps and hold my arms out a 
little from the elbows for balance; that it would certainly be impossible for me 
to walk with my normal male gait in high heels.  I must have been quite a 
sight when I came mincing out, heels echoing on the pavement, arms bent 
delicately and fingers held out to avoid touching the offensive satin swirling 
about my hips.  With each tiny step, the petticoat tickled my stockinged 
thighs and seemed to tease me into a never ending, escalating state of arousal.  
For the first time, I could feel the coolness of a gentle breeze blowing 
unencumbered up my dress.  I had never felt more exposed!

When we got to the car Maggie spun me around and planted her lips to mine 
and gave me a soul-searching mouth kiss, her tongue forced my lips to part 
and delved into the depths of my mouth.  All the time her hand was under my 
short skirt stroking my engorged, trapped cock.  She released me from the 
kiss and told me, "We are going to have so much fun when Ms. Williams 
sends you back to visit us!"  I got into the car rather ungracefully, petticoats 
all a-fly, and undeniably exposing my pantied derri¸re one last time.  Maggie 
tossed the samples I had gathered through the door behind me with a hearty, 
"Don't forget your daywear!" and shut the door.

Toni had a very satisfied smile indeed, as the pretty French maid, that was 
just minutes before, Mr. Smith, climbed into the back of her car.  Toni drove 
and remained silent, but all the time she had this grin on her face.  I was just 
beginning to think I would be spared more torment when she crooked the rear 
view mirror, and asked with a mock innocent air, "What's the matter, Mr. 
Macho?  You don't want to jump over the seat to put your hands on me now, 
no?"  With that, she abruptly stopped the car along the road.  I had no idea 
where we were.  Now it was she climbing over the seat, and the next thing I 
knew she had her tongue down my throat and her hand running up and down 
my stockinged legs.  

"So aloof now, are you?" she hissed in my ear just before she put her tongue 
in it while roughly pulling my hard cock through a leg opening of my sexy 
panties.  She had one hand squeezing my cock, and the other was deftly 
pinching one nipple through my bra.  I did try to push her away, but 
somehow I became weaker and weaker in her stronger and stronger embrace.

I wanted to get out of the car and run away when she started asking me 
embarrassing questions while she toyed and played with my rock hard 
erection.  It was as though she was seeing what effect her questions would 
have on my cock.  "You are a sissy bitch, yes?" she suggested.  "You want 
to learn what it's like to be tamed?"  I wished she would stop licking my ear 
and please make her stop kissing my neck like that!  Toni knew what she 
wanted, and she knew how much time she had left to be at the airport on 
time.  She just pulled her pants down and shoved her musky pussy in my 
face.  "Lick me, mademoiselle sissy bitch!" she commanded.  I gave several 
tentative slurps to her pussy.

Toni pulled her pants off the rest of the way, and pushed me down further 
into the seat of the limo.  She kept reminding me as I licked her pussy with 
growing fervor- "You are the one now, who's wearing a dress, nylons, and 
high heels.  You are such a sexy little thing.  How do you like it?  The shoe, 
er, pump is on the other foot now, isn't it, you pussy-licking slut!"  Toni was 
making me give her pleasure without my getting any pleasure of my own.  
Was this what girls go through?  Wait!  I am not a girl!  But she was not 
about to allow me to even pleasure myself.  When she saw me trying to rub 
my cock with all those rows of ruffles, she pulled my hands over my head 
and pressed down hard on my lap with her all of her weight.  I couldn't even 
pump my cock in the air, and she laughed when I tried.  A company 
chauffeur was humiliating me, and there wasn't a thing I could do about it.

Toni looked much happier when she dropped me at the airport than she did 
when she'd picked me up.  Her parting words were, "I hear you have a 
dinner date tonight with Ms. Williams.  Have you picked out a gown yet, 
sissy boy?  Huh?"

I was really glad I wouldn't have to go through any airline passenger check-
in line, and I wished desperately to change out of this degrading costume.  I 
would have to ride the Concorde dressed this way, and how would I explain 
it to Rebecca were she to hear about this?  Oh no!  I still had to face the other 
chauffeur, Janie.  I thought it was fun to look up her skirt and said as much.  
Now I guessed I'd be finding out what it's like.

The trip back on the Concorde was rather uneventful, unless you consider the 
fact that here I was a male dressed in a frilly maid's uniform, my hair coifed 
with a short blonde wig and my penis held captive in satin panties.  I might 
just as well have been wrapped in chains and locks, I WAS TRAPPED.  On 
the plane the only unexpected thing that happened was that a beautiful woman 
sitting beside me remarked she thought it was so humorous that I would go to 
such lengths to please my husband/boyfriend who would undoubtedly be 
waiting for me with the airplane landed.  She actually thought I was a 
GIRL!!!  Which is more embarrassing, I wondered, to be made as a man in 
women's clothes or to pass as a girl?  I breathed a sigh of relief when the 
plane landed and I could run off to catch the connecting flight back home on 
Women's World's private jet.

Once the company jet had left LaGuardia I was finally able to relax a little and 
try to figure out what exactly had happened to me and how to get out of it.  
And I hated to admit, even to myself, but entertained thoughts known to only 
me: how I really enjoyed the silk and satin prison I was trapped in.  My cock 
had never been so hard!  I leaned my head back and closed my eyes, trying to 
vanquish such thoughts and sleep on it.

Suddenly, I was brought back to reality when a woman's voice next to me 
said, "Something to drink ma'am?"  I opened my eyes to see Janie!!  There 
this vision of beauty stood before me.  She giggled hilariously as she spoke, 
"Well, I see our Mr. Macho is really a pretty little sissy at heart," as her hand 
snaked underneath my skirts and rubbed my imprisoned cock, again bringing 
it to full mast.

She calmed herself a little and explained that Ms. Williams had sent her to 
New York to meet me.  She said she was advised that she would either have 
a 3 hour "sucking and screwing" session with a real man, should I turn out to 
be one, or else 3 hours to get me properly prepared for my dinner date.  
Should it turn out to be the latter, she was expected to "explain" to me how 
my life would be from now on.  She giggled again, noting how glad she was 
that it was the latter of the two that she found.  "Come now, Heather, we 
only have a short time to get you ready."

Chapter Four

Complete Makeover

 Janie stood in front of me for a minute with her hands on her hips and a look 
of triumph on her face.  She seemed to be studying me.  When I looked up at 
her, all I could remember was how soft and hot her thigh had felt under my 
hand just hours ago.  Her face broke into a broad, pretty smile as she spoke, 
"What?  You don't want to run your hand up my leg and under my skirt now 
Mr. Macho?  Or should that be Miss Sissy now?  Yes, I think it is now Miss 
Sissy."  She said it with so much sarcasm in her voice it stung all the way to 
my toes.

She explained that Ms. Williams had bet that I would take the course that I 
had taken.  And that now that I had made the choice to follow the path to 
being a beautiful sissy, it was her job as Ms. Williams' "personal trainer" to 
ensure that I went down the road with the proper attitude, demeanor and 
look.  Just like she had done with all the others.  

That last statement sent a chill down my spine.  I looked at her in shock as 
she went on to explain that yes, Ms. Williams had done this same thing to 
other males, but that was not to be my concern now.  She was no longer at 
liberty to discuss company business with me.  I was to be concerned only 
with the present and to simply listen closely to what she said.  I was to follow 
her every instruction closely, from now on, as if I had any choice.  "Oh, 
yes," she pledged, lowering her voice, "not all go willingly.  I'm glad to see 
you're not one of those."

Janie just looked down at me from her superior position and ordered me to 
rise and turn around.  I did as she had instructed, wondering why I didn't 
just revolt and tear these silly clothes off!  I should be showing her I was a 
man, not some obedient little wimp.  Yet, I seemed to just blindly follow her 
instructions, not even raising any objections.  She pulled me closer and 
unzipped the dress in the back, pulling it off of my shoulders and letting it fall 
to the cabin floor.  Next came the frilly crinoline.  Suddenly I was standing 
there in just my stockings, panties, garter belt, bra with huge breasts jutting 
forward, and a pretty camisole.  Seeing her in her short, tight, leather mini 
had also left me with a hardon that was unmistakably poking the front of my 
panties out.  "My, don't you look so pretty?" she teased with now familiar 
sarcasm. 

Then before my widening eyes, she began to unbutton her satin blouse, 
exposing her gorgeous breasts caressed, as they were, in their lacey shelf 
bra.  I thought they would spill out at any moment.  Reaching behind her she 
unzipped her little mini and let it fall to the floor, leaving the unmistakable 
smell of leather in the air.  She kicked it onto the pile with my dress and 
crinoline petticoat.  She was wearing only the briefest of black satin panties, 
which she slid off of her waist and over her thighs.  Looking at me she put 
her hands on my shoulders and pushed me to my knees.  "You have made me 
so excited, 'Heather', I must have some of you before we continue."  She 
pushed her pussy in front of my face tersely, and I could smell the musky 
pleasure that lay between her thighs.  I leaned forward and tentatively licked 
her pussy.  Janie moaned a little, and grabbed my head, draping one leg over 
my shoulder so that I nearly swallowed her hot, wet pussy whole.  "Be a 
good little sissy bitch and lick my hot pussy, girl!" she cried. I had no choice, 
other than suffocation, so I obliged her demands.  It occurred to me that I had 
no desire for another choice.  I licked her till she had four orgasms, yet she 
was still ready for more.  But she knew time was limited, and Ms. Williams 
was very unforgiving of tardiness.

Satisfied, she pulled away from my juice soaked mouth.  My makeup, what 
little I was wearing, was totally messed, and my cock was throbbing and had 
left a huge wet spot on the front of my panties.  She leaned down and gave 
me a deep French kiss, her tongue forcing it's way into my mouth and 
seeming to penetrate me there.  Her kiss was more than a mere kiss, it was 
like a little fuck.  I felt so helpless to avoid her demanding tongue, it seemed 
to compel my very soul to open, widely, willingly.  To submit.

I was dazed when she pulled me to my feet, and then sat in one of the 
comfortable chairs in the cabin, studying me again.  She pulled my panties 
down and my maleness sprang forward, nearly hitting her in the face.  
Pulling them off completely she draped them over my hard cock.  "My, look 
at your pretty little clitty.  It's is so hard and excited, did I do that to you, 
Heather?"  I was a bit taken back by her referring to my manhood as a clitty, 
and my name was not "Heather".  As alarmed as I was, my urgent need was 
screaming from my loins and overtook any anger I may have had.  Anger, 
you see, being mixed into the stew of emotions and physiological takings 
place as my poor body had endured this day was not an option.  

Taking the silky panties and draping them over my hard cock, she looked in 
my eyes and smiled.  "Does my pretty little sissy want to cum for me"?  
"Yes," I mumbled.  "Are you a pretty little sissy boy, who likes, no, needs to 
dress in pretty lingerie and dresses?"  Try as I might to not admit to such a 
foolish thing, what she was doing to my "clitty", I mean cock, was driving 
me wild.  I needed to cum so badly that I just said, "Yes, I am a little sissy 
boy who needs to dress in silky, frilly lingerie and dresses.  I want, no, need 
to be a girl for you.  Please let me cum?!" 

"Will you do what ever I may ask of you, and I mean anything, without 
question?  And will you wear exactly what I tell you to wear?  And will you 
always obey the women in your life, like a good little sissy girl?" 

"Yes!" I screamed, "Whatever you say!  Please just let me cum, PLEASE?" 

"Very well then, Heather," she smiled as she draped the silky panties over 
my jutting pole.  She left the sexy garment hanging there over my cock like 
some obscene flag.  "You may put these back on and cum like a girl.  Use 
only your fingertips, like this."  I looked up at her mesmerized, as Jeanie 
pulled her own sexy panties on and began to rub her crotch.  "Fingertips 
only, like this."

I pulled the panties back on and knelt before her, watching her example.  
Touching my hard "clitty" with just the ends of my fingers like she was.  
"Oooh, Heather, doesn't that feel good?  Gently stroke your clit through the 
sexy fabric.  MMmmm."

It didn't take long, especially since you consider that I had been horny and 
excited all day long, for me to begin to orgasm.  I felt it start from somewhere 
deep within me, the mounting pain that longs for release, the itch that cannot 
be scratched.  It all overtook me in a rush, and washed over me in wave after 
wave of sheer ecstasy.  Soon, the panties were discoloring as hard spurts of 
cum tried with classic male arrogance to shoot through them.  Janie came too, 
smirking at the growing wet spot at my crotch.  And then I collapsed onto the 
floor, breathless.

When I finally regained some composure she was standing over me, having 
replaced her panties and bra, and she was smiling down at me.  She reached a 
hand to me to help me to my feet and once there, she ordered me to strip 
completely.  "We have a lot of work to do on you and not much time to get it 
done.  Ms. Williams, your new owner expects us shortly."  I should have 
been alarmed, I should have been aghast at her use of the word "owner".  But 
I was too weak to make such objections.  I felt owned.

After I had stripped completely I felt so completely helpless in front of her.  
She began by spreading some kind of pink lotion all over my body, which 
did not smell too good and soon began to burn slightly.  When I questioned 
this Janie told me it was one of Women's World's latest products, intended to 
take all my hair off, permanently.  "Have you ever seen a hairy sissy girl?  
We've developed our products, let's say, with a certain audience in mind."  

I was to find out that this jet had all of the amenities, there was even a 
shower, albeit a little cold.  And though I hadn't chosen to, I was standing in 
the shower watching the cold water wash all the manly hair from my body, 
forever, according to Janie.

Stepping from the shower she stood there with a towel and patted me dry.  
Standing back, Janie smiled her approval at my now hairless body.  I 
shivered in the cool air of the cabin and felt goose bumps begin to rise.  
Seeing her I also began to get excited again, she was so sexy again in that 
black leather mini-skirt.  She handed me what appeared to be a heavy satin 
thong panty.  It was a Lycra "cache panty" as she called it.  She ordered me 
to put it on, and I once again just blindly obeyed.  

As I pulled it up my now hairless legs and over my hips she reached down and 
pulled my "clitty" between my legs and pulled the panty up tight.  

"We wouldn't want a silly bulge to ruin the lines of your pretty dress, would we?"  

I could only shake my head no.  Then Janie started in earnest.  First, she handed 
me a pink satin garter belt, which she attached around my waist.  

"Pink is for girls," she mused while hitching it behind me.  Then she handed me 
a pair of tan silk stockings and watched as I pulled them up my new smooth legs.  

She watched me struggle briefly with the garter straps then came to my assistance, 
"I will not help you do this always, I am only helping in the name of saving 
time.  You will learn to do all of what I will do to you by yourself and I 
expect you to become proficient at it!"  I could only stand and watch, I 
wanted to break down and cry, yet I could feel myself beginning to get 
excited underneath the restricting cache panty.  

My erection pushed harmlessly at the entrapping sheath.  Janie seemed to 
expect this reaction and patted my crotch lightly, seeming to brag, "See?  
You're all nice and flat down there.  Just like all the other girls!"

Next she gave me a pair of frilly pink satin panties that hugged my bottom 
and waist and looked so flattering.  She ran her hand up the front and smiled, 
"See?  No nasty bulge to have to deal with, only nice and feminine."  Next 
she produced some breast forms and told me to lay on the couch, which I did 
all too willingly.  I watched as she rubbed some sort of lotion into my breasts 
and then on the inserts themselves.  

I nearly passed out when she came to me and placed the inserts over my own 
nipples and pushed them securely in place.  "Don't move for 10 minutes while 
these set up, yes it is nearly permanent glue.  Only Ms. Williams and I have 
the dissolving solution."  

Then to add to my distress she smirked, and told me "These will give you 
that feminine shape until your real ones grow, if that is what Ms. Williams 
decides for you."  After the glue had set she helped me to my feet, I felt so 
off balance with the new weight suspended from my chest, and I could feel 
them vibrate or wiggle with every move I took.  I got a kind of thrill from 
feeling it, like nothing I had ever felt before.  I found myself wondering what 
she meant by, "until your real ones grow."  Surely, they couldn't do that.

She had me slip my arms through a matching bustier.  The bustier helped hug 
my waist a little and held my new breasts close, suspended straight out in 
front of me.   Next came a matching satin slip.  I was relieved to be putting 
this on since it offered me some sort of modesty, even though it barely 
cleared my pantied bottom.  But when I felt the silky material floating over 
my thighs and ass, my cock was again straining against its luscious prison.  

Next, she produced a pair of 4" heeled stiletto shoes.  The shoes were a pink 
patent leather with an ankle strap securing my foot to the shoe.  "I can't wear 
these!" I pouted.  "You not only can, you will and you will always wear a 
high heel similar to these. How do you expect to become a perfect sissy girl 
for Ms. Williams if you don't wear these pretty high heels?  And besides you 
will learn to love them.  Now sit at my vanity so that we can get your makeup 
done, time is running short."  I meekly stood, nearly falling in the new heels, 
and stepped to her vanity.  Janie draped a towel over my shoulders, to keep 
my pretty lingerie clean, she said.  "You will pay close attention to what I am 
doing, you will be expected to make yourself pretty by yourself after this."  

I could not believe what was happening to me!  Here I was, sitting at a very 
sexy woman's vanity wearing all this silky lingerie, my cock was trapped in 
the cache panty and I was basically sitting on it. And this gorgeous woman, 
who only hours ago had my hand on her shapely thigh, was putting makeup 
on my face telling me I would have to do this myself in the future.  This 
could not be happening!  Secretly, and deep down inside, I loved it.  Did it 
mean I truly was a sissy?  I would get out of this somehow, and rise up to be 
a Wall Street Wiz yet.

Unfortunately, such thoughts running through my head caused me to 
misappropriate my attention to what Janie was doing to me.  She surprised 
me by suddenly she spinning me around to look in the mirror.  I could not 
believe what I saw!  There was a beautiful woman looking back at me!  This 
could not be me, I thought, and then looking at Janie and seeing her smile of 
approval, I knew it not only could be, it was!  I would have come on to this 
girl in the mirror, and she was me.  In fact, I was blushing furiously to think 
that she was turning me on!

Grabbing my hands Janie quickly glued girlish fake fingernails to my own, 
about 3/4" long, and painted them the same shade of pink that coated my lips.  
While the nail polish dried I was able to watch her get dressed again, sorry to 
see her cover any of her body.  Regret, I was tasting it in so many ways this 
day.

Then she went to the closet and brought out the prettiest white satin dress, I 
think I have ever seen.  I could tell though that it was short and tight.  
Standing in front of me with the dress in her hands she smiled and said, "I do 
think you will be the loveliest sissy girl in this dress, don't you, sweet 
Heather?"  I could feel the blush rise in my cheeks and much to my chagrin I 
could also feel my trapped cock begin to stir again in its satin prison.

Standing me up she slid the dress over my head and past my pseudo breasts 
to let it float down my body.  I registered a nine in the Richter scale.  Once it 
was in place she zipped up the zipper in the back and I could feel the dress 
wrap itself around me, it was very tight.  I thrilled at the new feminine 
feelings, and began to fall in love with them.  Taking my hand Janie led me to 
the full-length mirror and I could not believe what I saw, I was a beautiful 
woman!  I could also see that if I bent over just the slightest my garters and 
panties would surely be seen by anyone who may be looking.  I looked at my 
Janie with pleading eyes, "Please don't make me wear this to Ms. Williams 
dinner, I don't think she would approve."  Janie laughed and hugged me 
tightly and said, "Of course she will approve of you silly, sissy girl.  She 
bought the dress especially for you."

Just as the Lear Jet landed, Janie handed me a matching little purse.  She said 
the purse contained all the necessary items a sissy like me would need, such 
as lipstick, blush, other makeup and of course a sanitary napkin, just in case, 
and headed toward the door with me in tow.  When we got to the limo, she 
once again held the door, only this time the front door on the passenger's 
side.  I eased into the front seat as gracefully as I could even though I was 
sure I was giving Janie a beautiful shot of my panties while I did it.  "You'll 
learn," she chuckled.

She got into the driver's seat and patted the seat beside her and said, "Come 
sit beside me, pretty sissy girl!"  I moved over next to her and she 
immediately had her hand on my stocking covered thigh and was moving it 
under my dress.  She teased me this way all the way to Ms. Williams' estate, 
knowing full well that she was putting my trapped cock through pure hell!  
Thankfully we arrived at the mansion before I had an accident.  I never would 
have thought that I would be grateful to see the place where my life as I had 
previously known it, would end. 

Chapter Five

Indoctrination - New Rules

 When the car stopped in front of the mansion, Janie once again opened the 
door of the limo for me and took my hand to help me from the car.  She again 
smiled when she caught a glimpse of my pink panties peeking from under my 
dress.  She smiled, saying "You are such a sweet sissy, tease you are," and 
gave me a little peck on the cheek.  She held my arm as we walked to the 
door, I think she could tell that I was extremely nervous and she tried to 
reassure me.  Walking through the front door and into the foyer I was startled 
to hear two pairs of high heels clicking on the marble floor, Janie's and 
MINE!  She left me standing in the foyer to summon Ms. Williams.  

While standing there I though of my options.  I could turn and run out the 
door and escape.  But reality took over, where could I co dressed like I was?  
Police?  No, I think not.  I would probably get arrested or worse.  I could not 
do much, I didn't even have my clothes or my wallet, and even if I did, I was 
broke anyhow.

I was wrenched from my thoughts by the sound of a hearty woman's voice.  
It was Rebecca!  How could I face her?

"My, my, my, how the mighty have fallen!  Don't you look like the sexiest 
sissy girl in the world?  Janie has done wonders with you, even better than I 
had expected.  How do you feel now, 'Mr. Smith'?"

Ms. Williams had seen me, it was all out now.  The way she looked at me 
made me feel like a mouse about to be devoured by a cat.  I wanted to melt 
into liquid and run through some imagined crack in the floors of the opulent 
apartment.

Rebecca just strode gracefully toward me, and held my shoulders to kiss me 
firmly on the lips, her tongue sliding into my mouth like she had always 
greeted me this way.  I parted my lips and took her tongue into my mouth as 
though it was the most natural thing in the world.  My knees became rubber, 
and before I knew it I was leaning full against her strong, statuesque body, 
my hands sliding up her back.  Her breasts were pushing into my breasts and 
she reached behind me, she grabbed my ass and pulled me into her crotch.  I 
was sure that I would rip the cache panty with my excitement, or worse yet, 
fill my panties with my cream.  Finally, released from our passionate kiss, I 
got a chance to see her.  

I knew she was beautiful, yet I had never seen her dressed like she was now: 
pure feminine power.  She wore a royal blue see-through, long gown and 
underneath, the prettiest lingerie I had ever seen.  She had a royal blue, satin 
shelf bra, which held her hard nipples up invitingly.  The matching panties 
and garter belt were barely visible, and her dark hose ran down her long legs 
like a river to pools which were perfectly matched 3" high heels.  Gazing at 
her panties I could see the outline of her pussy, and it appeared to me that 
there was a damp spot at the "v" of her legs.  She was absolutely gorgeous 
and I wanted her.  Then I remembered the way that I was dressed and how 
my cock was trapped between my legs!  Why me?

Rebecca dismissed Janie, each exchanging shrewd smiles.  Then we were 
alone.  "Well, 'Heather', I'm glad to see you have taken such an interest in 
our products," Rebecca mused.  I was speechless.  All I could think about 
was how I was a man and that I was now standing before the CEO of a major 
corporation in a dress!  Oh, how would I ever live it down?

"I can explain..." I started.  But Rebecca dismissed the notion with a wave of 
her hand.  "No, let me explain," she declared with a fiery tone I hadn't 
expected.  "You were hand picked, Heath.  Chosen carefully, by me, if you 
will.  You are one of the brightest, and I must say looking at you now, 
prettiest male sissies I have ever set eyes on.  But where are my manners?  
Please join me for dinner."

She looked so beautiful and yet somehow Rebecca was stronger than anyone 
I had ever yet known.  Captivated by the starkness of the contradictions that 
she alone embodied, I could only follow where she led.  And she led me to a 
dining room that I can only describe as vast.  There, she pulled out my chair 
for me and seated me like I was the lady.  But Rebecca was certainly the lady 
here.

Soon, there appeared a lone servant girl with the first course of our meal.  As 
the poor girl hovered about us, Rebecca started to tease her as Janie had been 
teasing me.  "My," Rebecca remarked, "your little titties are growing so 
nicely!"  The servant girl blushed deeply but continued serving us.

"Now where was I?" Rebecca reflected.  "Oh, yes.  We at Women's World 
believe that male dominance of our planet was, at a time, a necessity.  
However, it's clear that since we no longer have any saber tooth tigers 
running around, there is no longer any need for male protection.  With the 
end of that need, meaning the arrival of civilization, came the advent of the 
male's compulsion to invent ways to make themselves remain important.  
More quiche dear?"

I found myself hanging on her every word.  She was making sense.  Lord 
knows everything I had learned in my MBA program made little sense to me.  
She went on...

"We at Women's World, arrived at the conclusion some time ago that it is 
merely a process of evolution, that males eventually become subservient to 
females.  We're simply speeding up the process.  It's inevitable, dear, don't 
you agree?"  

I wanted to run!  I started looking around and wondering which window I 
would crash through and where I would run after that.  Then she reached 
over and put her fingers at the nape of my neck and started playing with my 
hair there.  

"Come now, my little sissy.  I've had reports on you all day long," Rebecca 
whispered letting the nails of her other hand ride easily under my dress.  She 
slid one hand up my stockinged leg, the other hypnotizing me at the back of 
my neck, and soon I found myself saying, "Yes, ma'am."

"You love being treated this way, don't you, Heather?"  "Ooooh, yes, 
ma'am."

Rebecca just grinned and cooed, "Then it's time we put you in your place, 
don't you think?"

"Ooooh, yes, ma'am.

Rebecca took me by the hand and led me to her "master suite" and shut the 
doors.  I was enchanted by this awesome beauty, and let her take my pretty 
dress off with no hesitation.  She looked down at the cache panty and shook 
her head.  "Darn, we have to get rid of that.  I have something quite different 
in mind for you, Heather."  I stood submissively as she got on her knees and 
pulled the tormenting panty down my legs and flung them into a corner.  My 
cock pointed straight out, sticking practically in her face.  She detached my 
stockings from the garter straps and slowly filtered each one down my now 
hairless legs.  I lifted my feet, one by one, and she had my stockings in one 
hand while the other was stroking just behind my knees.

I could feel her breath on my cock as she said, "I wish I had a real man!  I 
would love to suck a powerful man's dick!"  She pushed my hands behind 
my back and tied them together with one of my stockings.  My hard cock was 
practically slapping the cheek of her face.  "But you are not a real man, 
Heather.  You're just a feminine, little sissy girl!"  While she said it, she was 
wrapping one end of the other stocking around the base of my cock and balls, 
tying it tightly.  Then she spread the remaining silky material of the stocking 
out over my stiff cock, enveloping it, and pulled it down abruptly between 
my legs, up the crack of my ass, and secured it to the space between my tied 
wrists.  "There," she said in triumph, "now every time you move your 
hands, your sissy clit will be stroked by pretty, feminine stockings.  That 
should keep you!"

"How does is feel to be put in your place by a woman!"  I moved my hands 
about and sure enough, the friction of the stocking torture device on my cock 
and against my ass was doing its work.  Soon, very soon, I fell to my knees, 
begging for release.  "Please, ma'am, I'll do whatever you say."

"Yes, you will, Heather.  Oh yes, you will..."

As Rebecca rose from her kneeling position I thought she would never stop 
rising upward.  She was like an angel, floating ever upward, borne on wings 
of sheer pleasure.  She looked down into my hungry eyes, and romance 
threatened to wash the moment away, eclipsing my lust- our lust, all lust.   
And I felt myself falling deeply in love with her.  

She took me into her arms, her fiery eyes devouring my body.  I was a 
conquest, yet my willing passion reached a foreboding place.  The look in her 
eyes, the way she held me.  How I thought that it should be I who did these 
things.  Still, in that moment, I gave my love over to her and surrendered 
totally.  "I love you..." I breathed from somewhere deep within me.  

It was true, I loved her from that moment, wishing that all the moments that 
make up time could somehow be this moment.

I knew that I wanted to be hers, to belong to her.  I knew that I did belong to 
her now, and that somehow, she belonged to me.  All other realities simply 
disappeared and all other things ceased to exist.  I felt myself swoon.  I was 
were I belonged and would stay forever, a sissy owned by a beautiful, 
dominant woman.

Suddenly I felt Rebecca's lips on my own lips, our lipstick mingling 
together.  She pressed her mouth hard against mine and let her tongue force 
it's way deep into my mouth.  She grabbed the back of my head and pressed 
me deeper into her lips, her other hand found its way to my ass and she 
pulled me into her crotch.  I truly knew at that moment what it must feel like 
for a woman to be ravaged by her lover.  The movements also caused me to 
move my hands and in the process stimulate my already aching cock trapped 
in the silk stocking.  I suddenly feared that I would cum too soon and loose 
this moment forever.

Rebecca backed away from me and looked lovingly at me. "Do you want to 
be my sissy girl Heather?"  I could barely mumble the word "Yes".  "If this is 
so, you will always be the feminine sissy that I require.  You will always 
address me as Ms. Rebecca, unless the situation does not warrant it, which 
will be very seldom.  You will always do what I ask without reservation or 
hesitation.  Such actions will be dealt with by prompt discipline.  Do you 
agree to these terms Heather?"  I could only look into her eyes and nod, my 
voice failing me just as my cock was failing my masculinity.  "A nod is not 
sufficient Heather," she spoke in a firm tone.  "Yes Ms. Rebecca, I agree to 
your terms, I want, no, need to be your feminine sissy forever."  I could not 
believe what my mouth was saying, it was betraying me completely.  "Very 
well then Heather, as you wish.  On your knees before me!" she 
commanded.  I merely sank to my knees in front of her, my cock bobbing in 
the silk cage she had placed it in.

She turned and went to her vanity, her back to me for a short time.  I saw her 
remove her transparent gown and let it fall.  I stared at the beautiful sight of 
her lean shoulders and tight back leading to her tight sexy ass and long lean 
legs.  She was apparently putting something on.  I didn't have to wait for 
long to see what she was doing.  She turned and walked to me and there it 
was.  A long lifelike rubber dildo stretching from her loins!  While the rubber 
cock looked out of place on her feminine body, it also looked as if it belonged 
on such a beautiful, powerful woman, my owner.

Ms. Rebecca walked slowly to me, her lifelike dildo swaying back and forth 
in front of her, much like I remembered my own doing when it was hard and 
I was walking towards my latest conquest.  She stood before me, looking 
down at my feminine figure, my own cock jutting from my loins.  She 
grabbed her cock and began to stroke it and looked at me.  "If you are to be 
my sissy girl, one of the duties you will have is to service my hard cock on 
demand.  Since you are no longer a man, you must begin to experience true 
femininity at my hands."  

She took the cock and rubbed it on my cheek, then to my lips.  

"Kiss my cock Heather, do it now!"  

I tentatively kissed the tip of the hard cock in front of me.  She put her hand 
on my head and began to push the cock towards my face.  

"Suck my cock, sissy girl."  

I know not why, but my lips parted and I began to slowly engulf the hard, lifelike dildo 
in front of me.  Suddenly, I felt that this was the only place for me to be and 
the only thing I should be doing.  My masculine pride failed me completely as 
I took even more of Ms. Rebecca's hard cock into my mouth, and my own 
cock was rock hard and leaking into the stocking tied around it.  

"That's right, sissy Heather, suck your Mistress' hard cock.  You are getting 
me so excited, sissy.  You like to suck my cock, don't you sissy girl?"  All I 
could do is nod my agreement and keep sucking.  She pushed the dildo deep 
into my mouth till I felt the pseudo balls hitting my chin.  Then she began to 
push this mammoth cock in and out of my mouth picking up her speed as she 
went.  Suddenly, with her cock buried deeply into my throat, she stopped 
and looked at me.  "You are my sissy girl, aren't you Heather?"  I nodded in 
response, once again.  "You will make a very good girl for me I am sure.  
But to show your obedience to me and to fulfill your femininity, I want you 
to get on your feet and lean over the edge of the bed, when I remove my cock 
from your pretty mouth.  Do you understand?"  Once again, I nodded my 
agreement as she began to pull the hard cock from my mouth.  Once it was 
out, I reached over and kissed the tip before getting up with her assistance.

Gaining my feet, she helped me to lean over the edge of the bed on top of a 
big pillow that had no doubt been strategically placed there for my benefit.  
Bent over like I was, the stocking that bound my hands to my cock tightened 
cruelly.  I could feel the stocking slide deep into the crack of my ass and pull 
mercilessly at my engorged cock.  Ms. Rebecca just stood back, admiring the 
view for a moment.   Moving behind me she rested the dildo on my exposed 
ass.  Stroking the cheek of my ass she spoke seductively, "As a sissy girl, I 
think you know what comes next.  All girls cherish the moment they 
surrender their virginity to their stronger lover.  This is that moment for you, 
my sweet sissy.  I will take your virginity if you so request, but keep in mind 
that once I do, you belong to me completely.  I will mold you into the perfect 
sissy girl of my desires.  Your only desire henceforth, will be to please me 
totally.  Would you like that, Heather?"  "Yes!" I moaned into the bed.  "I 
didn't hear you, Heather.  If this is what you want, you must beg me to fuck 
your sissy pussy and make you mine."  

This was an extreme moment of truth, and I pondered my answer as best I 
could.  To be taken in this way would be one thing, to surrender to it, even 
beg for it quite another.  The considered words found their way to my lips.  
"Yes, Ms. Rebecca.  I want to be your sissy forever.  Please take my 
virginity, fuck my sissy pussy and make me yours."  I moaned.  I couldn't 
believe my ears, what was I saying?  Then it struck me, I did want to belong 
to this powerful woman, and I did want to be hers completely.

She reached down and untied the stocking, pulling it from the crack of my 
ass and causing me to moan loudly.  She then stepped behind me and said, "I 
hope your mouth got my cock lubricated enough Heather, but remember, 
every girl suffers a little bit of pain to achieve her womanhood."  This said, 
she began to push the monster cock into my tight, virgin asshole.  I winced in 
pain as she pushed harder and harder, till suddenly the head popped into my 
ass.  I screamed at the invasion and the pain, but she soothed me saying "go 
ahead, girl, scream if you must, no one will hear you but me, and the 
possible exception of Janie and the maid.  However I would wager that Janie 
has the maid in a similar situation right now anyway, and I doubt they would 
care what was going on here.  So scream if you must, sissy, but this is 
imperative to your becoming my sissy completely.  You will come to enjoy 
my cock soon, even long for it."

She pushed the invader slowly but ever deeper into my ass, and soon, much 
to my amazement, I began to enjoy it.  The pain subsided and pleasure began 
to take over.  Could this be true?  Me, Mr. Macho just yesterday, and now 
enjoying being fucked in the ass by a woman while wearing frilly lingerie and 
makeup like a girl?  Could it actually be true that I was indeed a sissy, and 
that this strong, beautiful woman had seen it, known it, before I even did.  I 
didn't know and really didn't care, I was enjoying the feeling and knew that I 
would be enjoying it again and again.  I could feel an orgasm building in my 
stomach like I had never known before.

Ms. Rebecca hastened the pace a little and soon I felt the hard cock sliding 
fully into my ass, the pseudo balls hitting my own on the inward stroke.  I 
could also hear her moan as she picked up the pace.  Could it be, that we 
would both cum at the same moment?  Unexpected, she grabbed my hips 
tight and thrust with all her might deep into my ass and screamed a passionate 
scream.  And I knew she was cumming!  The thought that I could bring this 
beautiful woman to an orgasm by simply dressing in feminine clothes and 
letting her humiliate me in this way, took me over the edge.  

I began to cum like I had never cum before, almost from a place in my body I had never 
known existed.  The silk stocking trapping my hard cock did nothing to 
contain my excitement, I could feel it spreading through the stocking and on 
the bedspread beneath me.  I could also feel Ms. Rebecca spasming in her 
orgasm.  Trying to push even more of her cock into me, even though there 
was no more to push.  She fell over me and held me as both hers and my 
orgasms subsided.  I reveled in the feel her hot breath on the back of my neck 
and her small kisses nibbling on my neck.  

It was over, and I could feel her beginning to pull her cock from deep within 
me.  Some part of me never wanted her to remove her cock from me.  
Sensing this she hugged me and laughed, "Not to worry my precious sissy 
girl, there is more of that to come."  Then I felt the cock pop from my ass to 
be replaced by only emptiness.  She pulled me to my feet and untied the 
stocking from my wrists and removed the one from my now shriveling cock.  
Throwing them aside, she stood me up and led me toward her bathroom.  
"Undress me, Heather." was all she said. 

With trembling fingers I reached behind her and unhooked her bra marveling 
at how her breasts stayed taut and firm without the bra.  Kneeling before her, 
I removed her heels and slid her stockings down her long lean legs.  Laying 
them aside, I looked up right into those blue panties, only now I could easily 
see the outlines of her pussy as the whole front of her panties were soaked 
from her orgasm.  I smiled to myself, knowing that I had done this to her.  
Placing my fingers in the waistband, I began to lower them.  Slowly her wet 
pussy came into view, and I fought with everything the instinct to just bury 
my face in that pleasure spot.  After taking off her panties I brought them to 
my face and inhaled the fragrance and then ran my tongue over them and 
tasted her essence.  

I could have died in peace right there with her panties in 
my hands and my tongue licking her essence.  She stopped my revelry and 
brought me to my feet.  Removing the rest of my clothing, she led me to the 
shower and pulled me into it with her.  The warm water was wonderful and 
she proceeded to wash my body completely, not missing a spot.  She handed 
me the sponge and I began to wash her body lovingly.  Mine was a more 
thorough wash as I savored every inch of this goddess's body, her perfect 
breasts, her stomach, her legs and feet, then her awesome ass and then her 
perfect pussy.  We showered in complete silence and she didn't say a word, 
just spread her legs when I kneeled and began to wash her pussy with my 
tongue.  She pulled my head into her hot pussy while I licked her, and I 
thought I may suffocate as she ground her sex into my face- then, she came 
again!

Our shower over, I dried her off and powdered her, and she left me to do the 
same for myself.  Smiling over her shoulder all she said was "Plenty of 
powder sissy, a girls best friend."  When I emerged from the bathroom she 
was laying in bed in the nude waiting for me.  Beside her, was a pink satin 
baby doll nightie with matching panties, all covered in rows of delicate white 
lace.  I did not need to ask because she pointed to the sexy clothes and said, 
"Your night clothes Heather.  I hope you don't mind, but I prefer to sleep in 
the buff, but insist on my girls being dressed appropriately for bed."  I was 
helplessly caught and I knew it as I let the nightie drop over my head and my 
now hairless torso and hips.  Then came the matching panties which, with 
monotonous predictability, began to confer new arousal.  "Horny again are 
we sissy girl?  My, you're a regular little sex kitten aren't, you girl?" she said 
with a charming laugh.  

I crawled into bed next to her and she wrapped her arms around me and pulled me close.  

She reached up and clicked off the light, kissed me deeply again, then said, 
"Good night, my sweet little sissy Heather  There is much for you to learn, 
but if you pay attention and strive for perfection, you will have a wonderful life 
and I know I will.  You will be forever mine, sissy, and I am sure the pleasures 
we will share are too numerous to count."  

She fell asleep with me in her arms, tweaking my hard 
nipples underneath the ultra feminine nightie.  Sleep came hard for me that 
night, as I had no idea of what I had gotten myself into or what would 
become of me.  Nor did I understand why I enjoyed it so.  I realized that if I 
had chosen to, I could have slipped out of the house and made my escape, 
but there was something deep within me that forbade such a course.  What 
would life bring me now?  Finally I fell asleep, dreaming of such funny 
things as frilly satin and silk and all things feminine.