Getting Ahead

By: Noreen Wilson

CHAPTER ONE: A MATCH OF UNEQUALS

My wife Ally is smart, gorgeous and, above all, ambitious.

I am none of those things.

* * * *

I am not stupid, mind you. And I am not exactly ugly.

I AM decidedly lazy and unmotivated.

Why shouldn't I be? I was born Brian Malcolm Powell heir of THE Richard
Powell founder of the Powell Container Company. You might not have
heard of Powell Container Company, but it has its hand in producing all
or portions of three of every four containers you are likely to find
around your house. My dad worked hard to build his company and showered
my mom and me with his largesse. When I was ten, he set up a trust for
me that I understand has somewhere between one-hundred-fifty and one-
hundred-eighty million dollars in it. I never really kept that close a
track on it. I mean does it really matter? Besides, I don't get to
touch that money. It is administered by an army of accountants and
lawyers all of whom are overseen by the trustee. The trustee has
absolute discretion in spending "my" money for what the trustee believes
is my own good. The trustee also has absolute discretion on whether and
how much "allowance" I am entitled to receive.

That arrangement was fine as long as the trustee was dad. Until
recently, dad had always been a doting husband and father. When my mom
was alive, he took great pride in the fact that he was able to support
her in a manner fitting of royalty. He had no qualms about spoiling mom
or me. Being from the old school, dad always believed that a wife
should not have to work, and, in fact, should not work. It was not that
he subscribed to the philosophy that a woman's place was in the kitchen
or even that he believed a woman should be subservient to a man. It was
just that he believed having a wife who worked reflected poorly on the
man as a provider. When mom died of cancer when I was young, I guess I
became the lucky sole font of dad's self-esteem. He showered me with
everything a boy could have. Like my mom, I honored him by gratefully
accepting his largesse with no shame whatsoever. I suppose as I got
older dad wished I was a little more self-motivated like him.
Nonetheless, his pride in his accomplishments more than made up for the
lack of mine.

All this is to say that when I was younger and throughout college, I
never had any problem convincing dad that I needed this or that or of
cajoling from him a grand here or a grand there for one whim or another.
I never lacked for the trendiest clothes, the newest gadgets or the
raciest cars. I earned none of it and felt not a single moment's regret
or responsibility.

That was the life I lived.

Then I met Ally.

* * * *

I met Ally at a fraternity party during my final semester at Harvard. I
would say that our meeting had been totally by chance; but I know now
that it had been anything but.

For one thing, Ally should not have been at that party. She had not
been invited. She was not a member of any of the sororities. Her
mother happened to be a cook at one of the frats. Although she had
attended college and had just recently graduated, she had done so on a
hardship scholarship. The fact that Ally finished near the top of her
class was impressive. Nonetheless, she was still a "townie" who lived
on what my dad would have called "the wrong side of the tracks."

Not that you could ever tell it.

Ally was gorgeous. Standing at five feet, ten inches tall, Ally had one
of those slim, statuesque figures so popular among models. Yet she was
not skin and bones. She was compulsively athletic, working out five
times a week. She could bench press as much as most guys. She was
skilled in such exotic martial arts as Jogo do Pau, Wing Chun, Savate,
Muay Thai and Capoeira, as well as the more familiar Shaolin Kung Fu,
Taekwondo and Aikido Jujutsu. She could easily intimidate men twice her
size, not to mention guys smaller . . . like me. Yet, she dressed with
a feminine flair and casual chic that put the other women to shame and
she carried herself in a manner that many would call regal.

Despite my blue chip name, gals as beautiful as Ally normally do not
give me the time of day. I'm just not all that impressive. You see,
unlike dad who is a powerfully-built former football star, I inherited
most of my genes from my mom. If I crane my neck I stand at five feet
six and three-quarters inches tall and weigh all of 130 pounds, 130 and
2/3 pounds before I dry off from my shower. I have my mom's small bones
that, together with my complete lack of athletic acumen and aversion to
exercise, combine to give me a slight build that is almost epicene.
Unfortunately, my diminutive stature did not stop with my physique. The
word around campus from the few girls with whom I had gotten lucky was
that as cunnilinctor I the equal of any lesbian. When it came to
plowing their fields however my hoe just did not cut it.

You can image my surprise therefore when this goddess slithered over to
where I was standing and struck up a conversation. Surprise gave way to
outright disbelief when she took my hand and led me to one of the
several rooms that were left empty for couples to party at another
level. The sex had been wild. Perhaps that was because Ally did not
wait for me. From the beginning she took charge and then she took me
places that I had never been. She loved it when I licked her pussy.
When I crawled on top and stuck my little appendage into her she giggled
but held me close to her while she began rubbing her clitty. I
deposited my male seed a couple of strokes later. Ally, however,
wrapped her legs around my waist and did not let me go until she
finished bringing herself off with her own skills. I was afraid that
she had been disappointed with my prowess. If she had been, however,
she never let on, at least back then. Rather, she soon parlayed our
little tryst into a full blown relationship.

Dad had been more reserved about Ally at first; which is to say he was
outraged. Ally was not "our kind of people" he insisted. Then HE met
her and soon he was as hooked on her as I was. In fact, to tell the
truth, there were times when it seemed like Ally was more attracted to
dad than to me. The two of them would spend hours talking about
politics and business, especially Machiavellian financial maneuvering.
I would sit on the sidelines like the proverbial bimbo not having a clue
as to what they were talking about or the inclination or intellect to
learn.

* * * *

A whirlwind romance climaxed in a quiet engagement followed by a small
private wedding so atypical of high society. That was fine with me. I
am not really a people person. It was a bit awkward having your bride-
to-be ask you to marry her, especially given our disparate social and
economic positions. Surprisingly, dad did not seem to mind; in fact, he
seemed as pleased at Ally's social audacity as he was disappointed in my
lack of manly initiative. For my part, I just saw it as one more
potentially ego-deflating responsibility I had managed to avoid.

The wedding was a delightful affair. Ally looked stunning in her Galina
Signature Collection gown. Its virginal white organza over satin,
regardless of how inapt the symbolism, was breathtaking against Ally's
soft tanned skin and rusty blond hair. The gown seemed to float just
off of her shoulders and the ruffled lace flowers along the top of the
bodice added a feminine flair to the modern swirl skirt. Her elbow
length, two-tiered veil with Soutache edge and crystal embellished
floral motifs added dramatic mystery to a woman who was already
inscrutable and whose hold over me seemed mystical almost to be point of
being necromantic.

In contrast, Ally had me wear a pedestrian gray tuxedo with a run of the
mill blue dress shirt and white silk tie. Next to her I looked
positively subfusc and vapid. It was almost as if I had been the one
who had grown up on the other side of the tracks rather than Ally. A
groom is always supposed to take second fiddle to the bride. In this
case, however, the fashion inequality seemed to take bridal superiority
to a disquieting extreme.

When the festivities were over our limousine and driver took us to dad's
penthouse in New York for our wedding night. Since we were not
scheduled to fly out of LaGuardia for our honeymoon until Monday, dad
had suggested that the penthouse would be a perfect place for a wedding-
night layover.

When we were alone, Ally wasted no time in grabbing the crystal decanter
that contained dad's Remy Martin Black Pearl Louis XIII cognac. Dad
loves his cognac. I remember dad swirling the dark amber fluid in his
glass and murmuring almost reverently how the Black Pearl was actually a
blend of 1,200 cognacs of various ages, some as old as a hundred years.
He said that it carried a bouquet of flowers, fruits and spices and it
had a rich, hefty flavor of ginger, cinnamon and Cuban cigars. (I don't
have a clue as to how a brandy can taste like a cigar). It is one of
the rarest, and, at $55,000 a bottle, most expensive, cognacs in the
world. (Even at that price the Black Pearl was a distant second or
third behind the bottle of Henri IV Dudognon Heritage that my dad kept
at home. That vintage is supposedly mixed by the direct descendants of
King Henri IV and is aged in a barrel for more than 100 years. No doubt
it is a fine, fine cognac. Even so, something tells me that the cool $2
million price tag for this finest of brandies most likely had to do with
the 24-karat gold-dipped and 6,500 diamond-bejeweled decanter in which
it was bottled.)

I belabor this point only because I found it somewhat disconcerting that
Ally seemed to know exactly what she was doing in reaching for the Black
Pearl. It was almost like she had been here before. She handled the
exquisite decanter much as my father did and poured us both a hefty
snifter of the costly Black Pearl as though it was nothing more than the
Jack Daniels we used to drink in college.

She held up her glass and toasted me and my dad. "This is what I've
always wanted," she crowed. "I'm on my way!" Then, clearly as an
afterthought, she corrected herself and said, "We're on our way!"

She rushed over and grabbed me by my shirt. She pushed me against the
cabinet pinning my hands behind me. I assumed the dominant gesture was
merely the product of momentary passion as our tongues entwined still
lacquered with the buttery fire of cognac. Their friction sparked a
fire of an entirely different sort.

There was nothing gentle about her kiss. It was forceful and
domineering more than it was passionate. It daunted and cowed me before
her. That was Ally's way: she was always in control. Her dominance was
at times unsettling. But, I never resisted. It was hard to resist Ally
when she made up her mind about something.

Besides, now was not the time to resist.

Not bothering to get undressed, Ally pushed me down to the floor while
she hiked her gown above her waist. I knew what she expected. By this
time in our relationship I had come to appreciate a good clam dive and
was an undisputed cunnilinctio maestro.

Grabbing Ally around her knees I buried my head between her thighs and
thrust my tongue into her pussy. Entry was barred by the silky film of
her expensive panty hose that were already drenched with her juices.
Almost as if reincarnating the loss of her virginity (a loss that
predated me by who knows how long) Ally tore the fragile barrier asunder
to grant my tongue free rein amidst her folds of Venus.

I lapped hungrily at Ally's love liquor savoring it as much as the fine
cognac that preceded it. A lot of guys might have found it demeaning to
be kneeling before their wives and lapping at their pussies. Me? I
felt comfortable. I loved hearing her moan and squeal in recognition of
my talented tongue. Oh, occasionally her passion became uncomfortable
like when she smashed my face in her sopping cunt so that I could hardly
breathe. That, however, is simply the price one pays for being a
devoted husband and bikini burger connoisseur.

Ally must have held me there for forty-five minutes before she finally
laid me back on the floor and drew down my pants. By this time my
little cock was as hard and big as it could get. Ally got astride me
and lowered herself onto my puny piston.

I was buried in her to the hilt when she moaned breathlessly, "Let me
know when you're in sweetie!"

I blushed to a deep red in shame. Her face matched mine as she realized
her faux paux.

"Oh honey, I'm sorry! I didn't realize. You're just so . . . small!
Don't worry. Not every guy can be a stud. Here, let me help."

She reached down and pinched my dick between her fingers to make it a
little harder and just a tad longer. It was still not satisfying to
her. So she began to rub her swollen clitty. After just five pathetic
strokes I pumped my Cyclops tears into her. She hardly noticed as she
reached her fifth climax due more to her self-service than my nugatory
thrusts that were hardly more than pokes.
We made love twice more before leaving for Hawaii on our honeymoon.
When we got to Hawaii we spent most of the time on the beach or in our
room. When in our room, we spent most of the time in bed. Ally let me
inside her only a couple of times. The other times she made me settle
for a tender hand job saying that it was a less frustrating means of
giving me some relief than traditional sex. She did not give me much
opportunity to protest. She just sat on my face for what seemed like
hours on end as my tongue brought her to one orgasm after another. By
the time we returned from our honeymoon if my tongue were a bicep it
could have bench pressed 500 pounds.


CHAPTER TWO: GETTING AHEAD AND FALLING BEHIND

Once the honeymoon was over, it was over.

When we returned Ally wasted no time in making it clear that she would
be responsible for the family finances. I could have cared less. Our
finances were largely administered by the trustee of my trust fund and
when it came to paying bills who wants that task? With little regard
for possible consequences or male pride, I was perfectly content at
being a "kept" man.

This cavalier indifference carried over to the work place. Both Ally
and I went to work for my dad. Ally was named dad's Special Executive
Assistant. This was an important position and one I thought would be
mine. Instead, I was relegated to the mailroom as a clerk. When I
complained to dad he scoffed and said that I had not demonstrated the
ambition or the aptitude to be his Executive Assistant, whereas Ally had
already proven herself in "so many ways."

I could not argue with the first point.

As for the second point, dad did not elaborate on the talents Ally had
displayed in so short of time. She did lighten her hair color: dad was
always a sucker for blondes. And she did dress in an enticing manner.
Her eagerness to please was undeniable.

I must say that it did get me a little jealous when I would come into
dad's office to deliver the mail and find Ally sitting on his desk with
her legs crossed and the tops of her fishnet stockings peeking from
beneath her too short and too tight skirt. Even more disconcerting was
that her sweater or blouse would be askew and her impressive décolletage
would be on display, showcased in one low-cut lace confection or
another. She never wore such titillating underwear around the house for
me.

I could tell that Dad respected what Ally had to say, because he was
always staring intently at her while she spoke. Not that they said much
when I would come in. Usually, dad would quickly shoo me out as though
I had interrupted something important. When I closed the doors to his
office behind me I would hear giggles and whispers. Obviously they
enjoyed working with each other.

I must admit that I admired Ally's ambition. She put in long hours at
the office working with dad and several other male executives. I was
contented to clock out at five o'clock sharp.

Ally never talked about the projects that took so much of her time. She
would say they were company secrets and to ask my dad. Whatever they
were they must have been important, because I remember once trying to
deliver mail to dad around noon only to find the doors to his office
locked. He was in there, however. I heard both him and Ally. There
were noises like papers being tossed to and fro on his desk. Ally was
saying something like, "Oh Richard ... oh Richard ... I love taking your
dic...."

I knocked before Ally could finish saying dictation; at least that is
what I thought she was going to say. There was a silence before I heard
my dad ask who was there. He sounded strangely out of breath. When I
told him it was me, he told me that he and Ally were working on
something private and to just leave the mail on Ally's desk. No sooner
did I acknowledge this request than I heard the papers starting to
rustle once more and a little squeal come from Ally.

I know. I know. You are going to say that I was a fool not to realize
what was going on, especially in light of the rumors that were
circulating that Ally was more than a colleague to dad and several of
the other executives. In hindsight, I probably did know. I just didn't
want to admit it and did not care. I had my trust fund. My job in the
mail room was delightfully undemanding. Why rock the boat?

* * * *

Of course my passivity was not without consequences. The other
executives walked all over me despite my being the "boss' son." Their
disdain seemed to embolden Ally. She made it clear to me and others who
was the boss in our family. Dad likewise made his growing contempt for
me known in a variety of ways, beginning with his banishing me to the
mailroom while elevating Ally to the executive suite.

The maddening thing was that, whether the rumors regarding her behavior
were true or not, Ally really was brilliant when it came to finance.
She instituted processes and procedures that saved the company millions
and she more than tripled the company's income from its investments.
She may have been blond, but she was no bimbo.

I guess it came as no surprise to me therefore that within six months
dad announced that he was naming Ally to be the sole trustee of my
trust. At first, I was thrilled at this development. After all, I
presumed that with Ally as trustee my access to the trust fund would be
largely unbridled. Boy, was I mistaken. No sooner had Ally assumed the
trustee position than my spending money all but dried up. I had to
virtually beg her for every penny. Even then my pleas often fell on
deaf ears, even for money to buy such mundane items as new Jockeys.

At home, Ally's dominance also became more strident. She would rant at
me about how the other executives walked all over me and how I needed to
get a back bone. She called me a wimp. She even said she could not for
the life of her understand how I could be the son of such a MAN like my
father. She demonstrated nothing but contempt for me in front of the
household staff. I would often find her huddled with Agnes the
Housekeeper in the kitchen giggling or laughing and I knew I was the
subject of their humor. So obvious was Ally's disdain for what she
believed was my unmanly behavior that soon the entire staff began to
smirk at me whenever I would come into the room. There was not yet
outright mutiny, but in many and varied ways they made it clear that I
was Master of the House in name only.

Eventually it all became too much. I complained to my dad about how
Ally was treating me, especially with respect to denying me access to
what I believed were much needed funds. To say my dad was unsympathetic
would be an understatement. He lambasted me for being such a wimp.
"Hell..." he said, "...Sometimes, I think you're nothing but a gowd dang
sissy!" He went on and on about how I should be more like Ally. Show
some gumption and initiative!

When I retorted that it was hard to show initiative delivering mail dad
looked at me thoughtfully. "Funny you should mention that. Ally was
saying something like that just last night at our ... uh ... project
meeting. I know she has some definite ideas about your future. Let me
talk with her and see what we can come up with."

I wondered what that opportunity might be.

* * * *

I did not hear from dad or Ally for several weeks. When I did it came
amidst a bombshell. It seems that through a series of transactions
using blind trusts and corporate shells Ally had used much of my trust
fund to become the largest single shareholder in dad's company. If this
development bothered my dad, he did not show it. In fact, he seemed
positively ecstatic. He announced that effective immediately Ally was
to become CEO of Powel Container Company. Dad was to remain Chairman of
the Board.

Ally's ascendancy to the CEO position gave her more than effective
control of the company. Together with her position as trustee of my
trust, Ally now had absolute control of every aspect of my life. I was
soon to learn just how profoundly her newly acquired power would impact
my life.

* * * *

Shortly after she became CEO, Ally called me into her new office. She
was sitting back imperiously with her hands on the back of her head and
her legs up on her desk. Her blouse had popped open and her sexy tummy
was exposed. A smile of supreme satisfaction graced her face.

Ally always had enjoyed power.

Her smile quickly faded when I entered. I had never seen her more
stern. She told me that in giving her responsibility for running the
company the Board and my dad expected her to make the company run
smoothly and efficiently. She said that while dad might have had the
luxury of carrying dead weight, she did not. Nor was she inclined to.
Therefore, she said, I had two choices: I could resign and stay home
helping to take of the house or I could become a member of the
administrative assistant pool, what in the days before political
correctness would have been called the secretarial pool. As a secretary
I would work primarily for her, but like the other girls, would also be
expected to provide "periodic support" to the other senior executives.

Faced with a Hobson's choice, I chose to become a secretary.

* * * *

I guess becoming a secretary was a promotion of sorts from the mailroom.
It certainly beat staying home and watching the maids and staff.
Nonetheless, it was a bit awkward being the only guy in a pool
consisting of three women. When I complained that the other girls would
never help me out like they did each other, Ally said that it was my
responsibility to develop a rapport with them. I tried sitting in with
them at lunch. Yet, all they talked about were men, clothes and other
girly things. When I again complained to Ally she scoffed and said that
I had to develop a common interest.

The next thing I know I had subscriptions to Glamour, Cosmopolitan and
Vogue ... in my name ... delivered at the office, along with the other
executives' copies of the Wall Street Journal, Forbes and Fortune
Magazine. Ally made it clear that when I was not busy she expected me
to read each magazine cover to cover. After all she said, since I was
the only guy in the pool it would not be fair to make the women learn
about sports or what not. Besides, since I did not do my nails like the
other girls I needed something to keep me busy during the slow periods.

It was embarrassing to be seen reading the girly magazines. Egged on by
Ally no doubt, the secretaries would come over and tease me and ask
embarrassing questions about what I was reading. The questions about
menstrual cycles and "the ten easiest ways to please men" were
particularly humiliating. Ally insisted that I had to get over my
embarrassment and ordered the girls to take me shopping for tampons,
pantyliners and feminine deodorant just for the experience. At least
she did not make me use the stupid things ... yet.

Humiliating as it was, Ally's scheme actually seemed to work. As I
became more and more versed in feminine things I found that I could hold
my own in conversation with the other secretaries at lunch with greater
ease. They became friendlier. They even invited me to go with them on
their lunchtime shopping trips.

It did not please dad when he asked if I could work through lunch one
afternoon and I had to say no because the girls and I were going over to
Victoria Secret's. Seeing his shocked expression, I quickly explained
that "Vicky's" was having a fabulous sale on its popular "Sexy Little
Things" collection of bras and panties, as though any one should
immediately recognize the preeminence of such an event.

Dad just shook his head in disbelief before he burst into a disgusted
laugh. "Well in that case be sure to pick up a few for yourself. I'm
sure Ally will authorize such a worthwhile expense!"

* * * *

To everyone's surprise secretarial work seemed to suit me. I had always
enjoyed working with computers and was quite proficient with Word and
PowerPoint which the executives used frequently to prepare reports and
presentations. I also enjoyed tinkering with the copier, a task always
reserved for the girls until I came on. I could also make a mean pot of
coffee.

Alas, despite my secretarial proficiency and improving relationship with
the other girls, all was not a bed of roses. The other executives
continued to berate and mock me. Some of them complained to Ally in the
hallway that I was not as cute as the other secretaries. Others
complained to her that I did not take dictation like the other girls.
This complaint caused the other secretaries listening in to giggle and
Ally had laughed. I did not get the joke. I knew the other secretaries
would often be asked by one executive or another to "take dictation". I
also knew it was a demanding task, because the other secretaries would
often be tied up for an hour or more with the executive and when they
were through they usually came out of the executive's office flushed and
went straight to the ladies room. Nor did I see the humor when Ally
assured the guys that I was just new and soon my "skills" would improve
and everyone laughed even harder. When I asked the girls about it they
just giggled and snickered some more.

Well, a few days later Ally stopped by my desk with Connie, Ally's new
Assistant Vice President for Financial Affairs. Ally asked me to take
some dictation over lunch. Connie smirked. When I protested that I did
not know how to take dictation, Ally merely laughed and told me to be in
her office at 11:30 sharp. She also asked Connie to join us. Connie
snorted mirthfully and nodded.

At 11:30 on the dot, I knocked on Ally's door. Connie was already in
the room.

"Oh, Tink! Right on time."

I looked at her strangely. "Tink?"

Ally laughed. "Oh it's just a pet name I thought up for you. Cute
isn't it? You know: Tink ... as in Tinkerbelle?"

"But, Ally, Tinkerbelle is a little fairy."

"Yeah ... so?"

Connie burst out laughing while I turned beet red.

Before I could protest further Ally got down to business. "You know
Tink, it's about time that you learn to take dictation like the other
girls. Well ... that's what we all call it. It wouldn't be ... how
shall I say it? Comme il faut? . . . to call it by its many other names
at the office. You see, all of the executives have high stress jobs.
One of the roles of the secretaries is to help us alleviate that
stress." I looked at her with a puzzled look. "Oh don't be so dense
Tink."

Before my stunned face, Ally hiked up her skirt and pulled her panties
to the side. "Now get down here and get to work!"

It took a couple of moments to register what she expected. Connie came
over and placed her hands on my shoulders. She began to firmly push me
down as she whispered in my ear, "Ally has told me so much about the
marvelous tongue of yours!"

I was soon on my knees in front of Ally's chair. My head was buried
between my wife's legs. The familiar and entirely delightful pungency
aroused me and I was soon lapping away at her juicy cunt oblivious to
Connie hovering over me.

I am proud to say that it did not take me long to bring Ally to a
shattering orgasm.

"Ohhhh Connie she's sooooo gooood!"

My wife's misuse of pronoun totally eluded me in the shock of her next
comment.

"Okay Tink it's Connie's turn."

Before I could react Connie hiked up her skirt and stepped over me. She
had already removed her panties. She planted her pussy squarely over my
mouth and awaited the stress relieving bliss my tongue held forth.

At first I could not move. Then Ally reached down and pinched my nose
closed. Instinctively, I inhaled through my mouth and when I did
Connie's sweet juices flowed in. That was all it took. Within moments
I was lapping and thrusting my tongue into Connie's honey pot. She
tasted and smelled richer than Ally, although Ally tasted sweeter. I
never realized that feminine ambrosia came in different flavors. Connie
began to squirm on my face. Then she came. She actually howled in
ecstasy. "Ohhh Ally you're so right. She's magnificent!"

"He," I was thinking, although in my current position I could hardly put
words to my thoughts.

Connie came once more before she climbed off. Then Ally had one more
go. When the girls were through my hair was a mess and my face
glistened with sticky, gelatinous girl goo.

Connie and Ally lifted me from my exhausted prone position under Ally's
desk and half carried me across the hall to the bathroom. They were
wiping off my face when I suddenly noticed that the other secretaries
were there. Lisa and Amy were fixing their lipstick and the Abby was
pouring champagne.

I was in the ladies' room!

"Welcome to the girls' club Tink," Abby cried cheerfully while handing
me a glass of champagne.

"I'm not supposed to be in here!" I shrieked, as I turned to run from
this forbidden territory.

Lisa and Amy grabbed me while Ally and Connie blocked the door.

"Relax sweetie," Abby said, still proffering the champagne. "It's just
us girls."

"I'm not a girl!" I cried.

"Why of course not dear," Amy, the eldest of the secretaries replied
condescendingly. "... that's what makes you so special. Still, you've
now done 'dictation' like all of us girls ... well almost. So that
makes you an ... honorary ... girl, if nothing else."

"Yeah," Lisa added. "Every secretary when she's hired is told about
'dictation.' It's part of our job description. It's why we're paid so
much."

I could not believe this. Why hadn't dad said something to me? I mean
I knew the executive suite was a secretive place and isolated from the
rest of the company. But I had always thought that was just for
business security reasons not to promote promiscuity, if not
prostitution. No wonder that turnover in the executive and executive
secretarial ranks was so low and the company offered secretaries "early
retirement" when they turned forty!

I gulped down the proffered champagne as I pondered the implications.

I was a member of the secretarial pool. Got it. Like the other girls I
would be expected to give 'dictation'. Okay. I always liked eating
pussy. If Ally didn't mind my munching from another garden now and then
who was I to complain? Then it hit me. WOAHHHHHAAAAA!

"What about the guys?" I nearly screamed.

The gathered women burst out laughing. Their mirthful looks declared,
"It's about time Sherlock!"

Ally stifled her chortling long enough to say, "We'll save that for
another time. Okay, Tink?!"

She then turned and left before I could object.


CHAPTER THREE: SELLING MY SOUL FOR A FREE RIDE!

For the next several weeks I lived in fear of being asked by one of the
male executives to "take dictation." When no such overtures were
forthcoming, however, I began to settle into my new life as a member of
the secretarial pool, including taking periodic "dictation" from Ally
and Connie.

Likewise at home our sex life took on an essentially lesbian character.
Nearly every evening I would find myself buried beneath Ally's dripping
pussy lapping her to one orgasm after another. If I was not in the
mood, Ally was not deterred. She simply squatted over my face and held
my nose until I started chomping in earnest.

Occasionally, we would try to have sex like normal couples. These
efforts, however, always proved frustrating for me and for Ally. Even
swollen to its maximum girth, my "Johnson" just seemed more like a
"Janette" and neither of us got much out of the act.

Then it happened.

We were trying once more to have conventional sex. As usual Ally was on
top bouncing away frantically trying to compensate with enthusiasm for
what I lacked in length and girth.

Suddenly, she shouted "AWWWWWWRRRRRRGGGGGGG! That's it! I've had it!
You fuck like a gawd damn sissy!"

She threw herself off the bed and began pacing back and forth muttering
to herself. Then she abruptly stopped as though she had reached some
sort of conclusion.

She glared at me and said in a seething voice. "If you're going to fuck
like a sissy you might as well dress like one!"

I didn't know what she was talking about.

She stormed over, yanked me off the bed and dragged me over to her
dresser. Before I understood what was happening, she opened her top
drawer and pulled out the frilliest pair of red lace panties.

"Put these on you little fairy," she screamed.

"I will not!" I retorted indignantly.

With surprising ferocity and startling velocity Ally grabbed my arm and
twisted it behind my back.

I screamed in genuine pain. "You're hurting me!"

She cackled sinisterly. "You haven't seen anything yet you pathetic
little wimp. Now, if you don't want this arm broken you better get into
those panties. Do I make myself clear?!"

"Ya ... ya ... yes Ally."

She yanked on my arm harder. "And another thing ... from now on you'll
refer to me as mistress. Is that understood!"

"Bu... Yeoooowwwww!"

"There are no 'buts' twink. Whether at home, at the office or in public
you will address me as mistress and only mistress. DO YOU UNDERSTAND?!"

"Ya ... ya ... yes mistress!"

"That's better. Now stand up straight and let me get these panties on
you."

I stood there while Ally slipped the lace confection up my legs. My
tiny dick hung there, the quintessence of epicene flaccidity. When she
got the panties up my legs she gave them a particularly vicious yank
deep into my butt crack. She looked me over and shook her head.

"A sissy has no use for that," she said referring to my limp prick,
"Gawd knows I sure don't!"

She pulled the panties down and then with a truculence born of
frustration and contempt she grabbed my balls, pushed them up into my
body and then folded my penis back between my legs. She then tugged the
panties back into place. Now the front was nearly as smooth as a
girl's.

"There. That's much better," she declared. "You will remain tucked at
all times, missy! Is that clear?"

"Yes mistress."

Ally rummaged through the dresser and pulled out a black lace garter
belt and matching black stockings. She had me sit down. She did not so
much pull the delicate stockings on as she smoothed them up my legs. It
felt exquisite!

"We're going to have to get those legs shaved and the rest of you for
that matter. We can't have the company's newest sissy running around
with hairy legs. I'm just too tired to do it tonight."

When the stockings were fully up my legs, she had me stand up so that
she could fasten the garters. She told me to pay attention because I
would have to do this myself from now on. I did not dare ask what she
meant by "from now on."

When she was finished I looked down at my silk-encased legs. Something
about the little black ruffle at the top of the nylons excited me. I
don't know why. Before I could ponder the sensations long Ally flipped
a red silk nightshirt over my head. The strange sensation of satin on
skin and the exquisitely confining nature of the bra and panties made me
feel ridiculous and sublime all at the same time.

As I stood there relishing the wonderful new feelings, Ally went over to
her night table and opened the top drawer. She pulled out a bizarre and
dangerous looking contraption.

"I've wanted to do this for such the longest time. Isn't it lovely?"

Ally held up a large facsimile of a man's penis complete with balls. On
the back there was a curved protuberance that looked like a small
finger. The phallus was attached to a black harness which she proceeded
to fasten about her waist. When it was tight Ally looked like she had a
cock that had to be three times the size of mine. The little "finger"
was lodged against her clitoris and protruded into her vagina so that as
she was fucking she too would be stimulated.

I knew it would get me in trouble, but I was terrified. I ran.

I made it as far as to the kitchen before Ally caught me. She threw me
down and yanked my legs above my head and tore my panties to the side.
When the cold air hit my tiny hole I could feel it blossom as if in
expectation. Ally was looking down. She chortled.

"My, what a sissy you are, Tink! Your little boy pussy is just
throbbing in expectation. Once we get all that nasty hair off tomorrow,
the boys at the office are just going to adore our newest girl!"

As if to prove her point she poked one then two fingers into my opening.
I howled in humiliation as much as pain.

Then she flipped me over gruffly onto my knees on top of the table.
Without preliminaries she rammed her rubber phallus into my virgin hole.
Again I screamed, this time far more due to the pain.

Ally was not moved. "What's the matter precious? Don't you know that
we girls are expected to be ready for our men at all times? Don't
worry, by the time we're done you're going to be taking cock no matter
how big!"

With that Ally began to give me my first fucking. "Ohhhh isn't that
good sweetie? Just think how much you're going to enjoy having a real
cock inside you!"

Her taunts kept pace with her pounding. Gradually, however, they began
to ebb as Ally herself became lost in the Shangri-La of sexual bliss
manufactured by her powerful thrusts. Ally was an athletic woman and
she proved that she could fuck a man as forcefully as any man could fuck
a woman.

After about ten minutes of non-stop pummeling, Ally flipped me over onto
my back. My legs almost instinctively spread for her and she quickly
buried her ersatz cock back into my boy pussy. This time I squealed
with girlish delight rather than pain.

"Ohhhh does my little fairy like the missionary position? I bet she
can't wait to wrap those pretty legs of hers around some big hairy manly
man! Doesn't that feel sooooooo nice? That's what a real man feels
like inside you!"

Ally abruptly withdrew her massive dong and then inserted her pinkie. I
could hardly feel it after the gargantuan girth of the dildo. I
squirmed in frustration against her finger.

"See, that's what you feel like inside me you pathetic pansy. I need a
real man ... a man who will fuck me like this...."

She withdrew her insipid finger and plunged her synthetic cock back into
me. I wanted to despise this invasion. But god help me I began to love
it. My resistance collapsed and I began to meet Ally's thrusts. I did
in fact wrap my legs around her and grab her butt to try to force her
even more deeply into me.

Then I felt the onset of an orgasm. It was an orgasm unlike any I had
ever experienced. It began in the deepest, most secret part of my being
and then percolated outward inciting every nerve ending in my body as it
surfaced. My entire essence seemed to coalesce in my ass and cock.
Without even having touched it, a stream of Cyclops tears burst forth
from my still tiny and surprisingly flaccid cock. I grabbed myself to
keep from squirting Ally who was laughing at my ecstasy.

Ally gave one more powerful deep plunge and then collapsed on top of me
having cum herself for a fourth time. As she lay atop me panting
heavily she whispered breathlessly, "Oh my Tink ... my little fairy ...
I should have done this much, much sooner.

Exhausted we stumbled up to bed where we fell asleep with me still in my
bra and panties and with a bottom that was still throbbing with that
delicious enigma of pain and pleasure that results from a good sissy
fuck.

* * * *

The following morning Ally laid down the law. She said that she was
sick and tired of my good for nothing mooching, my pathetic apathy
toward responsibility and worst of all my worthlessness as a man. I was
at the core, she screamed, a sissy. A sissy is worthless as a giver,
but is an exceptional receiver and she intended to see to it that I
received everything I deserved.

First, we were going to go shopping for a complete wardrobe suitable for
a sissy, consisting of the frilliest bras and panties, the most
abbreviated skirts, tightest tops and shortest short shorts. To help me
grow accustomed to my new status, when asked I was to tell the
salesgirls that my name is Tink, as in Tinkerbelle. When next I
returned to the office, I would be an "active member" of the secretarial
pool, including taking "dictation" from all of the executives, just like
the other girls. It would be my "responsibility" to seek out the other
ladies and ask for pointers on how best to please each of the male
executives and then I was to share each of my experiences in complete
and titillating detail so we could "compare techniques."

This all would have been bad enough. But, Ally stunned me when she
declared that she needed a true man. She was tired of having to sneak
around in order to be satisfied. Therefore, she said I had better get
used to the fact that she intended to have a satisfying variety of
lovers. I was not to worry though, she would see to it that I
participated in her dalliances in a manner fitting for a sissy. That
participation was to be the "glue" that held our marriage together.

Ally allowed for the fact that I could always refuse these terms. In
that case, we would get a divorce that she promised would be messy. The
grounds for divorce would be incompatibility arising from the fact that
I was unable to please a woman like a man should. She would make
certain that these grounds were made very public. I would also be
fired. Most importantly, Ally would see to it that I received no more
than a subsistence level of income from my trust and would lead a life
of destitution.

Now I am sure you will say that these threats were hollow if I simply
stood up to Ally and got a real job like everyone else. However, you
don't understand the depth of my cowardice, the pervasiveness of my
laziness and the totality of my paralysis the presence of a dominant
woman like Ally.

Ally knew me though. She reached into her lingerie drawer and pulled
out a wisp of a bra. She dangled it before me. The gossamer fabric
swayed talismanically. Implicit in its proffer was that acceptance
would seal our compact.

I stood there for several moments. I was not really debating my fate as
much as I was pondering its profundity. Then, as we both knew I would,
with my head bowed in shame and submission, I reached out and took the
dainty garment thus avouching my destiny to become nothing more than a
cuckolded sissy.

* * * *

Like so many sacred declarations, my new life began with a baptism of
sorts. Ally led me into the bathroom and had me strip. She then
slathered my entire body, except around my pubic area, with the foulest
smelling cream. It began to burn. Just when I was not sure I could
take any more, Ally put me in the tub and began hosing me down with the
hand-shower. I huddled in the corner watching what little male body
hair I had swirl down the drain along with my masculinity.

When I was appropriately denuded Ally gave me a fresh pair of panties
and a bra. Then she sat me down to do my makeup. As she was setting my
foundation with a soft powder brush she elaborated on her expectations
for our imminent shopping excursion. I was almost in tears as I
listened to her instructions.

When she was done with my makeup I looked almost feminine and with a wig
and just a couple of refinements I could probably have passed as a girl
in all but the closest inspections. That, however, was not the plan.
Ally made it clear that I would be shopping in what she called "quasi-
guy" mode. That is, she wanted everyone to understand that I was a
sissy, not a girl. To that end I was dressed in a stark white bra and
panties topped with a sheer ruffled white blouse that barely concealed
my bra and tight short-shorts that let my lacey panties show
embarrassingly. The outfit and cosmetics, without the benefit of a wig,
gave me a humiliating epicene quality without concealing that I was
nominally a guy.

* * * *

I was trembling as Ally led me out to her car and we headed toward the
mall. Our first stop was a lingerie boutique. The store was bustling
on this Saturday morning. When one of the sales gals caught site of us,
and me in particular, it was all she could do not to burst out laughing.
Ally walked us right up to her and greeted her cheerfully and with a
matter-of-factness that belied the circumstances.

"Good morning, could you help us ... well him actually," Ally said
pointing at me. "My husband needs some pretty under things to wear to
the office. I was thinking maybe eight or nine bras and a couple of
dozen pairs of panties."

This was too much. The astonished salesgirl cracked up. Her laughter
drew the attention of several other shoppers who also could not hide
their snickers upon seeing me in my sissified state. They began to edge
their way over to get a better look at the oddity.

When the salesgirl regained a semblance of composure she replied
mirthfully, "Oh my, I see. We don't often get men shopping for bras and
panties for themselves."

"Well, you see my husband really isn't a man per se. He's more of a
sissy. Isn't that right dear?"

I looked at the salesgirl shamefaced. "Yes, mistress," I replied
haltingly.

"Isn't he just the sweetest, most docile thing?" Ally asked over the
salesgirl's guffaws.

The salesgirl looked at Ally and me. You could tell that she was not
quite certain why Ally wanted to demean me or why I would allow her to
do so. Nonetheless, if she had any reluctance about serving a "sissy"
that reluctance was trumped by the prospect of a huge sale that would
make not only her day, but her entire month.

"Oh I see," she replied when her laughter had subsided. "Well, you've
come at the right time. We're having our semi-annual lingerie sale and
we have lots of pretty bras and panties that I think would be just
adorable on you, sweetie. My name's Tonya. What's yours?"

I glanced around at the growing cluster of gawking, tittering and
snickering women. Mortified, I murmured, "Tink ... as in Tinkerbelle."

The entire store erupted in uncontrolled cachinnation. I turned bright
red. The guffaws and chortles went on for several minutes. The ladies
were clearly enjoying the spectacle.

Through it all I could see Tonya sizing me up. When the laughter calmed
to a smattering of controlled titters, she said, "Well ... Tink ... the
first thing I see is that you're a little underdeveloped for a girl your
age. It looks like you could probably use just a training bra." She
shrugged and more to the gathered ladies than to me said laughingly,
"Well, I guess that's probably common with sissies!" When the uproar
subsided, Tonya continued, "The problem is that most GIRLS your age have
outgrown training bras and I'm afraid we don't carry any in your size."
Tonya put her finger to her lips as though pondering a problem while the
women continued to laugh. "I think though that we might be able to find
some cute padded bras designed to give poor underdeveloped things like
you something of a figure."

She turned to the wall of bras behind her and looked the selection over.
She pulled a beige padded bra off the hook. "This bra is popular with
smaller ladies. I suppose it would look adorable on sissies too. It's
a padded bra by Fantasie that features dainty Swiss embroidery and
delicate motifs to give it such an adorable femmy look that I know
sissies must adore. Isn't that right sweetie?"

"Yes Tonya," I replied with Ally's prodding.

"Well I think you'll also like the fact that this bra is cleverly padded
to add one full cup size to girls like you with smaller busts and it has
what the manufacturer calls power net wings that add support and keep
the bra from riding up. Having your bra ride up can be SO annoying.
Don't you agree Tink?" This exchange sparked another round of hilarity
that Tonya allowed to run its course before continuing. "Now, I'm not
sure about sissies, but I know the girls especially like this pretty
color called 'Mink' because it won't show as much through sheer blouses
and you can get the most delightful matching panties in either a thong
or bikini style."

Upon hearing the description of the bra, Ally told Tonya that it would
never do. "You see Tonya, Tink, like most sissies, has more ...
flamboyant ... tastes. Tell her Tink."

The snickers were already starting when I began to recite the script
Ally had dictated to me before we left the house. "Yes, mistress. I
only like really pretty girly bras that are sure to be seen through my
clothes. The men just get so turned on when they see our bras through
pretty white tops."

"OHHHH STOOPPPPPP!" one of the women onlookers cried while laughing
hysterically. "You're going to make me wet my panties!" This sentiment
was expressed by several other women.

Another sales associate standing nearby held up another selection.
"Tonya, I think this one might be more suitable for an adorable sissy
like Tink. The boys couldn't help but notice that Tink was wearing this
pretty bra under her clothes."

The gal was holding up a bright yellow padded bra by Candie that had
what looked like watermelon slices with bright lime-green rinds. The
straps were the same garish lime-green as the rinds. The neon-like
colors were certain to show under my clothes. The associate then
explained that the bra also came with a matching bikini or thong style
panty that she assured me would be equally visible under tight light
colored skirts, slacks or short shorts "like I just KNOW sissies insist
on wearing."

Ally immediately said we would take it, choosing the bikini panties
rather than the thong because they would assure a more visible panty
line under almost anything.

We ended up getting four more Candie bras all of which were in bright
pastel colors and had bold check, polka dot or striped prints that
guaranteed that anyone who saw me would know I was wearing a bra under
everything but the most opaque tops. We also got a half a dozen more
bras from Bali, Maidenform and Lillyette with similar characteristics
and two dozen pairs of panties. I have to admit one of the Lillyette
bras in particular caught my fancy. It had embroidered polka dots in
white and pink on a white background and was finished with a long pink
bow in satin ribbon that also ran along the top of the cups and over the
straps. Below the cups were white and pink embroidered flowers. It was
indisputably one of the frilliest padded bras you could find and it was
certain to show especially under the nearly translucent blouses Ally was
certain to make me wear. Even under heavier fabrics its asperous
adornments and heavy construction assured that its bra-shaped outline
would be unmistakable. Of course, Ally made certain that I squealed
girlishly to Tonya that it was "exactly what I wanted."

My wardrobe did not stop at just bras and panties. I had nighties,
slips, a couple of basques and a number of special occasion bras. The
most tortuous garments, however, were the three heavily boned corsets
that Ally said I needed to "train" my figure. Each of the corsets was a
different length. Ally had the girls lace them so tight that I thought
I was going to be cut in two. When I complained that I could hardly
breathe, Ally sneered and told me that we girls have to put up with a
lot to have cute figures. She made me wear the midriff corset out of
the store.

It should go without saying that, once we had made my selections, the
girls all insisted that I had to try them on. They were more than eager
to offer their candid assessment of the bra or panties' fit and they
proved to be remarkably creative in finding ways to express whether they
thought the bra or panty was appropriately suited for "an adorable
little sissy" like me. By the time I left the shop I did not think it
was possible to be more abased.

The rest of the afternoon, however, was much of the same. Wherever we
went I received strange glares and biting gibes. The younger girls were
especially vocal in expressing their reactions to seeing a sissy in
their dressing room for the first time. These youthful and vivacious
antagonists were ebullient, facile and remarkably expressive in their
hectoring. They were also technologically savvy and used video phones
and small digital cameras to record the spectacle. Although I did not
know it at the time, one of the girls was actually broadcasting me onto
U-Tube or Facebook or some such place and several gals from work were
excitedly experiencing my debasement live.

The debilitating comments and mortifying gibes were fleeting. A more
lasting humiliation was the nature of the outfits Ally insisted I
select. Whenever a salesgirl would show me a cute top and skirt
combination, Ally would demand that I explain, as I did in the lingerie
shop, that sissies have rather "peacockish" fashion tastes that require
bright colors and lots of pretty frilly things so that we can stand out
and get noticed by gorgeous guys.

The result was that I ended up with some really bizarre outfits. For
example, I had to buy this ridiculous looking burgundy midriff-baring
top with satin bodice and huge lace ruffles that Ally paired with a
bright pink skirt. The discordant color combination and mismatched
fabrics were camp enough, but the skirt also had a large pale blue and
white flower appliqué that made the combination even more bizarre. You
can imagine the guffaws and gasps I received when I stepped out of the
dressing room to model the almost comical ensemble. Then Ally made me
get this bright yellow mini-skirt with a pale blue and green floral
print which she paired with a clashing dark green t-shirt with sequins.

When we were finished, I had a wardrobe that would provide the "Don't"
editors of "Glamour" magazine's "Dos and Don'ts" column with material
for months. I was not dressed like a woman. I was a mere caricature of
a woman which is exactly what Ally intended. As far as she was
concerned I was the epitome of a "chichi" sissy certain to get noticed
wherever I happen to prance.

When we had what Ally deemed an adequate start on a wardrobe for me, we
then went and had my ears and belly button pierced and then had a
makeover at Merle Norman's. There I had my first lesson in the
complicated science of skin care and the art of cosmetics. The color
combinations were not quite as bizarre as my outfits. Nonetheless, Ally
did insist that I select colors much brighter than were now fashionable
among girls, such as dark blue or bright metallic blue eye shadows with
deep rose colored blushes. When she was done I could have been the
keynote speaker at a Tammy Fay Baker fan appreciation convention.

At least Ally then let me get several wigs in various lengths and
colors. The wigs gave at least a modicum of femininity to my
appearance. The only problem was that the wigs were all expensive
natural hair wigs that I would have to learn to style or go to the
beauty parlor regularly to maintain. Ally assured me though that would
only be until my real hair grew out.

On our way home Ally stopped at Lovers-n-Lace. Unlike the prior stops,
Ally told me to wait in the car. I did not argue. I had had enough
humiliation for one day. She was gone all of twenty minutes. She came
out holding a small bag which she tossed in the back seat.

* * * *

When we finally arrived home I was debased, debilitated, depressed and
ready for bed.

"Not so fast sweetie," Ally said. "I have something for you." She
picked up the plastic bag she got from Lovers-n-Lace. "Take off your
skirt and top and get on your hands and knees."

I did not like the sound of that, but I knew enough to get on my hands
and knees without argument. With the tightly laced corset it was a
struggle to bend down and still breathe. A girl has to learn to adjust
though, and I did.

When I was on all fours, Ally pulled a large and strangely shaped pink
object from the bag along with a small bottle. She opened the bottle
and coated the device with a mucilaginous substance. Then she took her
slimy finger as pushed into my hole.

When realization dawned on me, I howled. "Ally you're not going to...."

"Oh hush, you sissy. Some of those guys at the office are huge. I
wouldn't want you to get hurt taking dictation." Ally began to plunge
the phallus into my almost virgin ass.

"Owww! Oh gawd, Ally, it hurts! Owww, please!"

Ally ignored my pleas and continued to press. I felt my ass being split
wide. Suddenly I felt more than heard a kind of pop as though my butt
had swallowed the thing whole. Then the pain eased ... to a degree. I
felt Ally grab something and wiggle it. I squirmed involuntarily.

"Aw, that's nice. I don't think that's going anywhere. Now put your
panties back on and get to bed. A girl needs her beauty sleep!"

She walked off laughing hysterically, leaving me kneeling on the floor
to ponder my fate with a pink butt plug rammed up my ass.

* * * *

Throughout the night I had nightmares about becoming a cuckolded sissy.
My nightmares did not come close to reality.

When I awoke Ally was already up. She was in the bathroom getting
dressed. I looked down at the ridiculous nightie I was wearing. I had
to do something.

I went into the bathroom. "Ally, can't we talk about this?"

Ally looked up from her vanity and glared at me through the mirror.
"WHAT DID I TELL YOU ABOUT CALLING ME ALLY!

"Sorry Mistress," I stammered quickly, not wanting to provoke a fight
this early in the morning.

"That's better," she responded dismissively while returning to applying
her makeup. Without stopping she continued. "Now, Tink there's really
nothing to talk about. First, you know you're not much of a man.
Surely you've known all along that I only married you for your money. I
hate to be cruel about it," she laughed derisively, "but, you're so
dense if I don't use simple words they'll never sink in. You can be
such a bimbo! Well, anyway, I have your money now. Frankly, as far as
I'm concerned you're quite expendable. The only reason I even keep you
around is that I promised your father. He's such a persuasive and
powerful man, so unlike you. We've become quite ... close. Anyway,
when I finally convinced him that you were nothing more than a piteous
candy ass, he begged me to help you. When he named me trustee of your
trust, he had me sign an agreement that essentially allows me to do
anything I want to you, except divorce you. It also provides that
should you acknowledge that you're a sissy I can't refuse any request
for funds as long the funds are reasonably related to your enjoying that
station in life. So you see, you can be quite comfortable coming out of
the closet so to speak. Of course, your father understands that I need
a real man in my life. So the agreement also provides that I can ...
entertain ... anyone I choose. If you interfere with my enjoyment in
the slightest manner I have the right to immediately cut you off from
all funds."

Ally put down her makeup brush and turned to me.

"There is an escape clause for you though. Your dad had me agree that
if you renounced any claim to your trust or to his estate and went out
and started on your own then we could get a divorce and I would have to
leave you alone. I readily agreed because frankly sweetie we both know
you're far too lazy and incompetent to be self-sufficient. Deep down
you know that you're nothing more than what we girls used to call a
"rumpy"; you like to receive rather than give. And you like being a
kept man, although man is hardly the word for you. Now, I've laid out
two outfits for you to wear. There's a set of male clothes resting on
top of a packed suitcase. You may put those on and leave at once.
Agnes will call you a cab. The other outfit is, shall we say, more
suitable for you in my opinion. Nonetheless, the choice is yours. When
you're dressed meet me downstairs.

* * * *

Ally got up and walked out of the bedroom. This was unreal. I had to
do something! I went over to the phone and called dad. I listened
stunned while he confirmed everything Ally had told me. I whined about
how unfair it was. I whimpered that he could not do this to his own
son. "What's going to happen to me?" I repined in a lamenting wail.

Finally, dad had enough of my pitiful puling. His voice boomed back so
loudly that I had to hold the phone away from my ear.

"Listen you little fairy I've given you every opportunity to act like a
man. You've shown over and over again that you're nothing but a lazy,
good for nothing, conniving, shamming cur. You can't even keep that
pretty wife of yours happy like a real man. Frankly, I'm not sure about
all this sissy nonsense, but Ally makes a good case. And I think our
arrangement presents a fair solution. Your fate is in your hands.
Stand up and act like a man or continue to milk off the generosity of
others on their terms. I've given Ally control of the company and your
finances. She's demonstrated initiative and has earned the right.
Besides, she's your WIFE for Pete's sake. If a man can't stand up to
his own wife ... well ... well ... then he IS a sissy and deserves
whatever comes to him." Then my dad laughed uproariously.

"What's so gawd damn funny?" I bewailed into the phone.

Dad continued to laugh for a couple of seconds and then replied. "I was
just thinking about the little bet I have with Ally."

"What bet?" I asked cautiously.

Dad laughed some more. "None of your business, but it's a bet I almost
hope I lose." Then, he slammed down the phone.

* * * *

Dad's derisive laughter was still ringing in my ears as I went into our
dressing room. Like Ally said there were two stacks of clothes ... two
choices ... awaiting me. I could live life like a man, but I would have
to earn it. Or I could continue in my lavish parasitic lifestyle but
only on Ally's terms. For a guy with even a scintilla of gumption or
iota of pride the choice would have been simple. I had neither. I had
been raised like the eagle chick: thriving off of the regurgitated
largesse of others. I saw no reason to learn to feed myself when others
were willing to feed me.

Yeah, you might say, but what about being treated like a sissy ... about
letting my wife fuck another man? My gawd man!

That's just the point though isn't it? Ally and dad had me pegged. I
was not much of a man. My sole ambition in life was to live as
comfortably as I could with as little work as possible. I mean you had
to hand it to Ally. She had outmaneuvered me, and perhaps even dad,
every step of the way. Dad was right: Ally had earned the position she
now held.

I picked up the wig that was lying on top of the pile of girl's clothes
and tossed it on my head. I looked at the tussled locks and smiled
sardonically.

If Ally wanted to treat me like a sissy, wasn't that her prerogative?
If she was willing to feed and house me and maintain me in the lifestyle
to which I aspired wasn't she entitled to name her price? Isn't that
what men the world over do with their wives? Must not women degrade
themselves in so many ways in return for a little security? Sure a lot
of women refuse to compromise: they refuse to rely on their husbands in
return for some independence. Yet, many, many women are more than
content to submit to the will of ignorant men in order to enjoy a life
with less responsibility and an afternoon of shopping or tennis with
their girlfriends. If men earn the right to treat their wives little
better than kept whores, had not Ally earned the right to treat me like
a sissy in return for allowing me to continue to mooch?

I shook my head in disgust and my pretty pastiche fell into that
organized disarray that so many men found sexy and women spent so much
money trying to achieve. I picked up the bra and panties and slipped
them on. Then I took the stockings and sat down.

Ally and dad knew me so well! Perhaps I would hate myself in the
morning. For now the panties did not feel so bad. The bra was not that
uncomfortable. And the stockings ... well ... they felt exquisite. So
what if people laughed? Sticks and stones and all of that.... They can
laugh while I laughed all the way to the bank. Yes, Ally knew me so
well.

* * * *

Unknown to me Ally was standing in the doorway with a somewhat sad, but
accepting, smirk on her face. She was engaged in her own introspection.
She had married a sissy. She knew it. She had always known it. She
had manipulated me, taken advantage of me. She had no regrets. That is
how one gets ahead: taking advantage of other people's weaknesses.
Heaven knew others had certainly taken advantage of her when she was
young and penniless. It's just the way of the world. She looked on me
now as kind of a cute pet, like the parakeet she had as child, that she
also had named Tinkerbelle. She had loved that Tink no less than the
poor thing sitting with his back to her dressed in panties and bra. She
would treat this Tink no worse: she knew that she just had to clip my
wings occasionally and it would be perfectly safe to let me out of its
cage.

* * * *

I thought I heard something behind me and looked back. No one was
there. I shrugged and finished putting on my stockings. When I was
fully dressed, I padded down to the kitchen where I found Ally in the
kitchen with Agnes the Housekeeper. They were laughing hysterically. I
had a strange feeling that they were again laughing about me. I had not
realized that Agnes was going to be there. Although I had crossed one
psychological barrier to becoming Ally's cuckolded husband, I was still
not quite ready for others to see me in that light. I tried to back out
before Ally or Agnes could see me. I was not quick enough.

"Oh Tink there you are, you pretty thing," Ally chirped. "Come in here.
Agnes and I were just talking about you." I shuffled shamefully into
the kitchen. "Agnes this is Tink, as in Tinkerbelle. Isn't she just
the most precious little thing?"

Agnes was snickering. She had long since ceased show me the respect
that a master of the house is due. "Oh yes Mistress Ally. She's sooooo
adorable."

"Now Agnes, as I was saying, you can see that my husband has decided to
adopt a slightly different lifestyle. As of this moment you shall not
refer to her or even think of her as my husband or even as master of the
house. She is Tink, or Miss Tink, if you prefer. Although Tink does
not answer to you, she has no authority to direct your actions or make
any decisions whatsoever regarding this household. Do you understand?"

"Yes, Mistress."

"Now, for the time being at least, Tink will continue to work at my
company." Both of our eyebrows arched upon hearing Ally's reference to
dad's company as hers. "Most of her time, however, will be devoted to
pursuing her new lifestyle. Isn't that right Tink?"

I crimsoned at Agnes' smug smirk. "Yes mistress," I replied with a
simper.

"Agnes, Tink is going to be undergoing some significant changes and I
expect you to help. You can start by making sure that she takes these
pills."

Ally opened two large bottles of pills. She tapped two pills from each
bottle and then handed the bottles to Agnes. Agnes snickered when she
read the labels before putting the bottles in her apron pocket.

Ally began to hand me the pills she had taken out along with a glass of
water. "Down the hatch sweetie," she commanded.

"What ...?"

Before I could even get the question out, Ally put the pills and water
down, grabbed me and yanked me over her knee. She flipped my skirt up
and pulled my panties down and then began to spank me like a little
girl. Agnes was laughing uproariously at my humiliating treatment.
When she was finished Ally yanked my thong panties up into my butt
causing me to yelp on top of the tears that were still streaming down my
face. Agnes continued to snicker as I rubbed my poor sore bottom.

"Let that be a lesson Tink. Agnes, if Tink gives you any trouble at all
about taking her medicine you are to give her a right proper thrashing.
Do you understand?"

"Ohhhh absolutely, Mistress," Agnes replied still chortling.

When my sobbing had subsided sufficiently, Ally again proffered me the
pills and I took them without question.

"Now, Agnes...," Ally resumed, "... in addition to making sure that she
takes her pills, as of today, Tink is on a strict diet. I want her to
have no more than 1200 calories per day until we get her weight down to
a more girlish level. You're also to take her to Curves over on
Princeton Avenue four times a week. They already know about Tink and
have arranged for a strenuous exercise program that will help trim her
tummy and waist and shape her butt and breasts. The girls are very
excited to see Tink. Our goal is that within three weeks Tink will be
down to about 110 pounds and have a girly 28-inch waist without needing
a corset. That should put her at a Junior size 7/8."

"Very nice ma'am," Agnes concurred with a condescending sneer.

"Yes, our sissy is going to have the most adorable little figure when
we're done with her. Oh how I wish I were still a junior size! Those
skinny juniors have just the cutest clothes!"

"And men seem to love those string bean girls," Agnes observed, a little
boldly for a woman in her position.

Ally giggled. "Oh my yes. I just know Tink is going to be so popular
with the guys at the office. That reminds me. Tink will no longer be
staying in the master bedroom with me. That will be reserved for me and
my ... guests. Tink will take over the "Pink Room" next to yours, at
least for now. If we end up hiring another maid like we discussed we
can decide what to do with our sissy then. Meanwhile, I would
appreciate you helping Tink move her things to her new room. Pay
special attention to her new sexy bras and panties. It will be
important for you and your staff to learn to tell her panties from mine.
I don't think it'll be too difficult even though we're the same size.
Tink's tend to be far frillier than mine. I learned yesterday when
taking her shopping that our little fairy has the absolutely daintiest
tastes. Don't you Tink?"

"Yes, mistress."

Ally laughed at my submissiveness.

"Ah, just what I like to hear!" Ally said with a satisfied smirk.

CHAPTER FOUR: LEARNING DICTATION

Ally had me take the following week off. She thought that I should get
more accustomed to my new station in life before plunging in. During the
week Agnes instructed me in everything a sissy should know, such as how
to sit without letting my panties show ("unless you want them to!"), how
to walk (especially in outrageously high heels) and even how to talk with
a cute sissy lisp. On top of that Agnes made sure I took my pills and
attended my exercise classes. By the time Monday rolled around, I could
mince with the best of them and Ally declared that I was ready to join
the secretarial pool.

* * * *

When Monday came, Ally woke me at 6:00 a.m., nearly two hours before my
usual time. I had to take a shower and carefully shave my entire body.
I was then lacquered in every type of floral and fruit scented lotion or
ointment known to womankind. I really did smell pretty. I smelled even
more so when Agnes came over at Ally's prompting and proceeded to bend me
over at the waist and yank the butt plug that had been ensconced there
for most of the week when my orifice was not being used for other
purposes. Agnes then liberally sprayed my ass with feminine deodorant
spray. I thought she was done and started to straighten up. Agnes
gruffly pushed me back over.

"Not quite done sweetie." Agnes then stuck a tube up my tail and
squirted something inside. "There you go. Now you'll be ready for those
big boys at the office." She then handed me a small bottle. "Put this
in your purse sexy. A girl can't have too much lube you know." Then she
burst out laughing.

* * * *

I pulled my panties up and then shuffled over to get dressed. I started
with putting on my long black wig. It shaped my face well and gave me a
modicum of feminine appearance. I had wanted to wear it plain, but Agnes
had come up with the idea of putting it into two pig tails tied with huge
white bows and dangling ribbons. It was a look only a sissy could love.
I then slipped into a pair of pink lace panties and a matching padded
bra. Over those I wore my green t-shirt and yellow skirt ensemble. Ally
insisted that I also wear a pair of white lace stockings. The concept
was not without merit. However, the stockings barely came to mid-thigh
and the tiny skirt did not fall that low. As a result the white lacey
tops of my stockings were on display, giving the look a decidedly
sluttish flare.

Of course, once I had it all on, Ally and Agnes insisted that I strike a
number of risqué poses and practice the flirting skills they had taught
me over the past week. Ally made it clear that those skills had better
be evident at the office or there would be hell to pay when I got home.

I must have performed reasonably well, because when I was done, Ally gave
me a derisive ovation and assured me that the guys were just going to eat
me alive.

Then we were off to the office.

* * * *

Needless to say Monday was not a particularly productive day from a
business standpoint. When the girls saw me they burst into a
cachinnation that seemed to vibrate throughout the office. They rushed
me into the ladies room proclaiming that a pretty thing like me certainly
could no longer use the men's room. They "helped" me freshen up my
makeup. One of them bought me a sanitary pad from the machine "in case I
leaked." Still laughing, they dragged me back to the secretarial pool
enclave where they regaled me with scabrous suggestions on how best to
take "dictation" and the pros and cons of the several executives who were
in the running to "take my cherry."

When my dad walked in the office grew silent. He walked up to me and had
me stand up. He snickered when I nervously tugged at the tiny skirt I
was wearing. "Very girly of you, son," he sneered derisively. He
continued to walk around me shaking his head. He pinched me. "Cute
tushie sweetie," he commented mockingly. Then he turned to Ally, still
shaking his head in disbelief. "You haven't won that bet yet!" he
snarled in a tone that suggested that whatever bet he was talking about
Ally did not have far to go to win.

* * * *

At around 11:30 Ally called all of the male executives into her office.
The other girls in the secretarial pool gathered around me all giddy and
giggling.

"I hear they're having a raffle of some sort," Lisa said excitedly.

No one had to guess at the prize. There was a great deal of hooting and
hollering going on behind Ally's door. On more than one occasion we
could hear Ally tell the guys to settle down. Once, we could hear Ally
cry in an exasperated, but mirthful voice, "Common guys. This is only
for first. You'll all get your turns eventually."

The girls gathered around me burst into giggles and I did my own
rendition of a Martian sunset as we all knew what she was talking about.

Ten minutes later there was a collective shout inside Ally's office
followed by a number of groans and laughing accusations about the fix
being in. Then the executives began piling out of her office. As they
left they all glared at me with lascivious leers. Mark Johnson was the
last of the men to come out followed by Ally.

"Oh Tink, could you come here please?" Ally asked in a theatrical tone.

I gulped and began to shuffle over to where Ally and Mark were standing.
Mark's eyes never left me.

"Tink, Mr. Johnson needs you to take some dictation. You have time don't
you?"

The office reverberated with more mock cheers and applause as Johnson
pumped his first in victory.

"Ya ... ya ... yes Mistress," I stammered. The office erupted in
chortling. They had never heard me having to address my wife as
Mistress.

Mark took my hand and guided me toward his office. As we were walking he
boldly placed his hand on my butt. I slapped it away instinctively.
This girlish instinct merely made Mark and the giggling audience laugh.
With an exaggerated wink to the chortlers, he slapped his hand right back
where it had been. Only this time he began to rub my butt in an obvious
and salacious manner prompting a torrent of lewd mockery having to do
with Mark's impending "coupling with my caboose."

Once we were alone, Mark wasted no time in pouncing on his inexperienced
and helpless prey. He continued to squeeze and caress my butt in a
titillating manner. Then he bent down and stuck his hand between my
legs. I girlishly cupped my hands protectively over my privates and
reflexively pressed my legs together in an effort to deny him access. It
was a vain effort.

His hand forced its way to the juncture that contained my sissy treat.
He began to caress the girly-sized appendage that was bent back between
my legs and so appropriately gift wrapped in pink lace. Despite the
circumstances I began to feel the first stirrings of arousal.

He left his hand between my legs and stood up and kissed me. It was a
lustful kiss, spurred by sexual arousal rather than affection. Mark was
a smoker and his tongue tasted bitter as it barged its way into my mouth.
For the first time I began to have second thoughts about my cowardly
compromise that had landed me in this man's office. Not that there was
anything I could do about it at this point.

Mark broke his kiss and began to force me downward while fumbling at his
pants. By the time I had reached waist height his pants were open and
his dick was protruding obscenely. I gasped. It was still semi-flaccid.
Yet, it was already twice the size of my woefully undersized appendage
when fully erect. He held his wobbling member still while forcing my
mouth closer. I gulped. The throbbing man bone had a gorgonizing affect
as it wobbled only centimeters from my half-parted lips. He thrust the
hardening member between my partially opened lips. When it entered, my
first reaction was how pleasant it felt. It was warm and silky, nothing
like the cold adamantine cladding of Ally's dildos on which I had
practiced for this moment. I almost gagged when I got my first taste of
pre-cum that had oozed from the tip. As it swirled around in my mouth,
however, I began to grow accustomed to the taste. I would not say it was
ambrosia, but, once you got over the repugnancy of having another guy's
spunk in your mouth, it was not an unpleasant taste.

That did not make the act any less distasteful. As delightful as the act
was proving to be, I could not help feeling cheap and dirty, like some
ten buck downtown whore. Of course, that is exactly what I was; I had
sold my dignity and my soul for a few golden trinkets. That is precisely
how Mark treated me. Mark, while somewhat older than me, should have
been a peer. Instead, he glared down on me in disgust as I sucked on his
member. "Gawd you're pathetic, man!" he sneered, not relenting on his
pace. "You had it all. Your dad owned the fuck'n place for Pete's sake!
Any you threw it all away. Didn't even have the balls to stand up to
that wife of yours. What a fuck'n pansy. I look forward to giv'n you
what you deserve!"

He yanked his cock out of my mouth and flipped me gruffly onto my hands
and knees. He handled me like a rag doll. He was right. I was a pansy.
I cowed before this display of manly strength and fortitude. He flipped
my skirt above my waist. I shrieked at the sudden coolness on my naked
butt. He tugged my panties out of my ass crack and to the side to give
him access to my cross-trained orifice. I remembered enough to grab my
purse and reach in for the bottle of lube Agnes had given me. I took it
out and held it back for Mark to use. "Please be gentle with me, Mark.
You're so big!"

Mark sneered but grabbed the bottle. He poured a generous amount of lube
into my puckered opening that was already throbbing in anticipation like
it did each time Ally or Agnes screwed me with their dildos. I was such
a slut I thought as I felt the head of Mark's cock pressing against me.

Mark's entry was actually rather anticlimactic. Having been fucked at
least twice a day by Ally or Agnes all last week and having to have a
butt plug in place when I was not being played with my opening was
accustomed to being filled. True, Mark was bigger than the dildos Ally
used. Yet, the difference between a dildo and a man was remarkable.
Ally's dildo was unyielding and uncompromising. When used with
uncontrolled passion it could be truly painful even when you were lubed,
expecting and even eager. Mark's penis though, even though it was erect,
was soft and pliant. Its blood engorged state allowed Mark to penetrate
me as aggressively and easily as any dildo, but its silky skin cushioned
the impact and lessened the discomfort. The other thing I noticed was
that Mark was hot, quite literally. His prick radiated heat that
actually made his entry easy and disturbingly arousing.

Mark pounded at me doggy style for several moments. Then he pulled out
and literally tossed me onto the couch in his office. He grabbed my
ankles and pulled my legs apart. I was embarrassed when my "clitty"
became untucked and poked from beneath my panties. I slid the tiny
member beneath its lacy domain just as Mark rammed his prick back into
me.

I shrieked and my cock twitched excitedly in its lacy confines. I looked
down and watched in rapt fascination as Mark fucked me ... made me a
woman. I could not help myself. I began to groan. It just felt too
good.

"Ooooooooo, Mark," I cooed involuntarily.

I swear I had intended merely to lie there passively and let Mark have
his way with me. But, I just couldn't. At that moment I could have
cared less that people thought I was a sissy or a whore or pathetic. It
just felt too absolutely, indescribably wonderful. If this was what
being a sissy meant then I was more than content to live with my
decision. With that catharsis I surrendered to my passions.

"Ohhhhhh gawdddd Mark! Ohhhh baaabbyyyy that's it, that's IIIITTTTTTT."
I was squealing and giggling like a girl. I was ashamed at what was
coming out of me but powerless to stop it! "Ahhhhhhh! Aahhhhhhh!
Deeper sweetie, deeper. Ohhhh, thhhheeeeerrrrreeee! Ohhhhhhhhhh.

Mark actually laughed at my passion. As pathetic as he thought I was, he
also took pride in the fact that he could make me squeal and I could tell
that he was enjoying it as well. I should have been ashamed, but passion
trumps shame. My Tinkerbelle-sized appendage erupted spewing its sauce
on my tummy. I reached up and pulled Mark down onto me and I wrapped my
legs around his waist.

"Ohhhhhhhhhh don't stop. Ohhhhhh Mmmmmaaaarrrrrkkkkkk! Harder, harder,
do me HARDDERRRRRR! Oooooooooooo I ... I ... ooooooooo ... I love your
dick inside me!"

Mark rammed himself home once more and deposited his male seed inside me.
He collapsed on my chest just as I came for a second time.

He lay there panting for several moments. His cock was still buried
inside me. I could feel it pulse and twitch. Slowly it subsided along
with Mark's gasps. Finally, his penis slipped out of me, leaving me
empty in a way I had never felt empty before. I reached for now deflated
flesh desperately wanting to guide it back in. I suddenly understood
what Ally had meant when she called be a receiver rather than a giver.
Beneath Mark I could receive his manhood without fear that I needed to
perform. I could please just by being a living receptacle and in so
doing I could feel like I never felt before. Oh, gawd help me! I truly
understood then what Ally needed and what I could not provide. Oh dear
mother, I needed a man inside me! Labels no longer mattered: Gay? Sissy?
Whore? Who frick'n cared. There was only need ... and satisfaction.

Mark got up and we dressed in silence. Then I left his office to be
greeted by cheers and laughs and mocking congratulations. I met the
hectors with a triumphant, "Go fuck yourselves" sneer. I was walking
funny as Mark's prodigious cum squished in my butt. I knew what I had to
do. I walked over to my desk and grabbed the sanitary pad the girls had
given me earlier. Without saying a word, I strolled out to the ladies'
rest room to perform the ritual every member of the secretarial pool must
perform after a successful dictation if she expects to keep her panties
dry and feminine.


CHAPTER FIVE: CAREER MOVE

My coupling with Mark marked a watershed in my relationship with Ally.
As she had promised, by the end of the week I had given dictation to
every executive in the office with the exception of my dad. Over the
weeks that followed, my passion for dictation reached new heights. I
thought Ally would be pleased. In fact, however, her contempt for me
grew. She seemed particularly troubled by the fact that I could enjoy
being a sex toy so much. Her response was to escalate her own sluttish
behavior. She blatantly flirted with the guys at the office in an
overtly sexual manner. She unhesitatingly discussed my shortcomings as a
man. I should have been humiliated, but what the heck, truth was truth.
Besides, if I was getting fucked by big satisfying cocks, did not my
precious wife have the same right? I certainly could not begrudge her
the satisfaction I could not give.

If Ally had been content to fuck and be fucked it would not have been so
bad. Ally used her extracurricular activities to debase me however
possible. She insisted on telling me every gory detail of every tryst.
She loved offering graphic and mortifying comparisons between her lovers'
equipment and my "fairy wand."

Her favorite and most disgusting debasement, however, was that she made
me clean her up after each coupling. She also made sure everyone in the
office knew what I was up to. After a steamy session with one of the
executives, she would open her office door with her clothes still a muss
and call to me sweetly, "Oh Tink sweetie, please come here and clean me
up!"

When I got to her office she would make me lie back on her desk while she
straddled my face. She would then squeeze out her lovers' cum into my
mouth. Often it would come out in such colossal quantities that I could
not keep up with it. Nonetheless, she would insist that I continue to
lap at her until every slimy seed was consumed. This disgusting task
would have been bad enough. Ally however would invite her lovers to stay
and watch me perform my sanitizing duties and would always leave her door
open so that everyone in the executive suite could see what I was doing.

* * * *

Ally's continually demeaning treatment of me coupled with my popularity
as an office diversion became increasingly distracting. Whether out of
jealousy or contempt, the girls grew more distant. In the ladies' room
they would mock me. It was not so much that I enjoyed giving dictation;
they all did. It was the near fanaticism I brought to the task. They
all enjoyed sex, but they were not about to demean themselves before men
they secretly believed were their inferiors. My subservience to my wife
. . . or as they called her "the Boss" . . . was particularly disgusting
to them. They said I brought an entirely new meaning to the term
brownnoser.

One morning Ally called me into her office. "Tink, I've discussed it
with your father and I have to let you go."

I stood there stunned. Then I began to cry. "Wa ... wa ... why?" I
stammered through my tears.

"Tink you've become ... uh ... disruptive to the business. Dictation was
intended to be an occasional mechanism to enable our executives to
relieve stress. You've elevated it to a pastime. There is not a day
that goes by that you're not banging one, two or three executives.
Nothing's getting done. Besides, the other girls are getting angry.
They don't respect you. Why should they? You're so busy boffing the
executives that they have to do all the work." I just stood there crying
unabashedly. "Don't be too hard on yourself. Frankly, I recognize it is
my fault to some extent. I just never realized that you were really such
a sissy slut. I mean, I know you couldn't please a woman, but I never
dreamed you could please a man so well and would enjoy it so much. Hell,
most of the executives aren't even gay and they would rather fuck you
than me." She shook her head as if nothing made sense. "Now, don't cry.
I have another job for you."

I looked at her through my tear-filled eyes. "Wa ... wa ... what ... I
... i ... is ... I ... i ... it?" I cried wiping at my cheeks.

"Well, sweetie, remember how Agnes and I have been talking about getting
another live in maid to help Agnes? The other day Agnes suggested that
you would be a perfect fit. I think it's a wonderful suggestion. The
job doesn't require a lot of brain power or ambition. It's a part time
job really, so you'd have plenty of time to go shopping and do all the
other things sissies like you like to do. Just think what an adorable
little maid you'd make. I mean just look at you. Those special vitamins
you've been taking are doing wonders for you. Why, I'm sure you've
noticed the adorable little titties you've been growing. I know everyone
around here has. Pretty soon you're actually going to be in need of
those pretty bras you like to buy. Oh and don't worry about being ... uh
... lonely. One of your jobs will be to entertain my many guests. You
know how after a long day at the office I sometimes don't have the energy
to cum more than two or three times and some of the burly guys I like to
fuck need more. I'm sure you'd love lending a helping hand, wouldn't
you?" She laughed at her churlish pun.

* * * *

Thus it was that I transferred from being an apprentice sex toy at my
dad's own company to being an apprentice maid in my own home. I would
say "Oh how the mighty have fallen" if not for the fact that I was never
that mighty and while the activities in which I engaged were drastically
different their undemanding nature remained constant.

Now, you're probably thinking that as a sissy maid I would be dressed in
one of those cute little black and white French maid outfits with
petticoats and frilly panties. That is not the case. You must
understand that our estate is large and the work is real. It is
comprised of a main house having 20,000 square feet and twenty-three
rooms, an indoor pool, a sauna, a fitness center and a twenty-five seat
theater. It rests on roughly 23.5 acres that accommodates the main
house, a large outdoor pool and pool house, servants' quarters, a
carriage house that will accommodate eleven cars and a boathouse down by
the private lake. Across the lake is my dad's estate which is even
larger. We have a staff commensurate with the estate. Agnes holds the
title Housekeeper, which is the female equivalent of Head Butler. She
oversees the entire household staff and is responsible for making sure
that the estate runs smoothly and that every whim of our Mistress is met.
To her report five live-in parlor maids, ten cleaning staff, the chef and
his kitchen staff, the two chauffeurs and the groundskeeper and his staff
of five including Tommy the pool boy.

As a result, while we all have what we call our "Ceremonial Uniforms"
that would make a pervert blush, our daily staff uniforms, while cute,
are designed to be more or less functional. Agnes' everyday uniform, for
example, is a rather plain black tunic with black lace at the hem and
white muslin trim along the short sleeves and neck. It does have a short
white apron with ruffled trim, but nothing as extravagant as the
ceremonial uniform.

The uniform is comfortable and easy to clean. Its only drawback is that
it is short. When Agnes has to reach high to clean the top of a cabinet
the tunic will hike up so that her cute little tush is there for all to
see. Agnes knows this, but she insists on wearing black lace thong
panties that she claims are "just comfortable." Consequently, the view
from the floor, where I am usually on my hands and knees scrubbing, can
be breath-taking. Alas, given my position as just an apprentice sissy
maid, I can only gaze upon that succulent tush with the same longing and
frustration as I imagine Tiny Tim experienced while gazing at the
unattainable Christmas goose hanging in the butcher's window

When I started my daily uniform was just as Spartan. It was also was a
short tunic style with a white collar and white trim along the short
sleeves. But, it did not have the pretty lace trim like Agnes' uniform.
This lack of frills was somewhat compensated for in that the apron had
slightly more ruffles. The primary difference between my uniform and
those of the other maids, however, was that my uniform was pink
indicating that I was an apprentice maid. It also let the rest of the
staff know that I was a rookie and hence fair game.

The entire staff was subjected to frequent inspections to make certain
that their uniforms were clean and proper. I was subject to inspections
that were for thorough. Mistress Ally in particular loved pulling
surprise inspections no matter where I was, what I was doing or who was
looking on, to make sure that my ass had been douched and was properly
lubed and perfumed (a sissy must have a femininely aromatic boy pussy).
She would spread my well-used bottom embarrassingly and say loud enough
for anyone around to hear that the inspection was for my own protection,
because you never know when some handsome stud might want to poke his
long thick pole up that "cute little tushie you're getting."

And I WAS getting a cute and versatile tushie. The little puckered
opening that had been my butt was now a large pink orifice constantly
receptive and, to my embarrassment, responsive to stimulation. It was
equally comfortable as a pussy as it was as a butt. More than that, the
"vitamins" I had been taking were really starting to take affect. My
butt was getting rounder, my thighs thicker and my skin softer. Of
course, by now I had figured out that the "vitamins" were actually female
hormones. I did not care. The little boobies popping out on my chest
were a little disconcerting to be sure. They became more so when
Mistress Ally took me to a clinic one day unexpectedly and had a
physician give me "C" cup implants. They looked great, but I soon
experienced the travails of a full busted woman, particularly the
discomfort of carrying around the extra weight when not wearing a
properly fitted bra.

Nonetheless, having a more feminine body has made my job easier in some
ways. For example, one of my more embarrassing responsibilities is to
replenish Mistress Ally's feminine hygiene products. Well you can
imagine the comments I received at the drug store when I arrived looking
like a sissy dressed in my apprentice maid's uniform and hit the check
out with a cart loaded with tampons, pantiliners (for both regular and
thong panties), feminine deodorant and douche. Surprisingly, it was the
female clerks, rather than the guys, who seemed to take the greatest
delight holding up a long checkout line while they interrogated me about
MY period and preferences in feminine hygiene products. As I took on a
more feminine appearance I could occasionally pass as a woman and avoid
these embarrassing confrontations. This was good, because eventually
Mistress Ally had me buy tampons, maxipads, pantiliners and douche for
myself and not just her. She insisted that I select brands different
from hers so that when I went to the counter I would have two different
brands of every feminine hygiene product. It was particularly
humiliating when a checkout girl would remind me that there was a two for
one sale on Summer's Eve douche and I had to explain to her that the
Summer's Eve was for my mistress and that the Massengill Baby Powder
douche with the redesigned nozzle "thoroughly researched and tested for
the comfort and cleansing of a woman's intimate area" was for me.

0My increasingly feminine charms were put to good use. More often than
not, if an "inspection" occurred in a bedroom, Ally would use the
occasion to strap on her dildo and give me a little "rumpy pumpy." The
act was no longer as embarrassing as it had once been. Mistress taught
me that when she strapped on her dildo I was to "assume the position"
which meant hiking my dress above my waist, pulling my panties to the
side and lifting my legs high so that my love button was presented to her
in a most inviting manner. It was a little uncomfortable at first. But,
through practice I have become flexible enough that I can comfortably
rest my knees on my shoulders so that Mistress Ally has unrestricted
access.

Mistress Ally would often spend twenty or thirty minutes pounding at my
little hole. My little clitty would spurt at least twice, although I
could not hope to match Mistress Ally's capacity to achieve four or five
orgasms even before she had me "clean her up" which usually led to one or
two more. I did not mind really. For, I knew that whenever I pleasured
Mistress Ally, or she took her pleasure on me, she was less likely to
spend as much time with the other men in her life. While I had come to
accept grudgingly that Mistress Ally could fuck and be fucked by whomever
and whenever she wanted, it still triggered some sadness and jealousy on
my part when she would come home with a twat filled with baby seed from
who knows whom or how many. I could only hope that she was on the pill.

* * * *

When Mistress Ally was not using me, the other staff members usually
would. Mistress Ally considered it "an integral part" of my training
that I learn to pleasure both males and females, because a significant
part of my responsibilities was to pleasure my mistress' guests
regardless of gender.

I cannot say that this "training" was without its pleasures.
Nonetheless, it could be annoying. Tommy the pool boy in particular
seemed to make it his personal crusade to assure that I knew how to make
even the most demanding male happy.

The problem was that he would accost me in the most inopportune times and
places. I would be trying to clean the hall floor and he would sneak up
behind me and grab my increasingly sensitive boobies. I must say it felt
wonderful and my little sissy clit never failed to twang at the assault.
But I had work to do!

Besides, Tommy never insisted on privacy. No matter how many staff
members were looking on, Tommy would hike up his shirt and pull down his
pants expecting me to suck him off.

Gawd, he had a cute cock. It was not as large as some perhaps (although
it was monstrous compared to mine, especially now with the female
hormones coursing through me). Nonetheless, it was absolutely delicious
and his man seed had that sweet taste and gooey consistency of tapioca
pudding, my favorite.

Still, it was humiliating to have one's sexual hunger on display in front
of two, three or even four people all cheering you on. One time I had to
"endure" sucking Anita, another apprentice maid, while the other male and
female staff, led by Agnes herself, gathered around and wagered how long
it would take me to bring her to three orgasms. (My record was five
minutes twenty-seven seconds).

The most embarrassing moments, however, were when Tommy would bend me
over in the kitchen and plow into my willing hole while the cooks looked
on and laughed. Again it was not the fact that everyone could watch me
getting fucked that disturbed me the most; it was the fact that they
could see in my face and hear from my cries just how much I had come to
love being fucked.

I still smile when I remember the first time that Mistress Ally walked in
and found Tommy intently pounding away at me. He was concentrating on my
hole and did not notice her at first. When I looked up and saw her, I
gasped. Then I realized that there was nothing I could do about Tommy's
throbbing cock up my butt so I just flashed her a "what the fuck" smile
and let Tommy pound away. When he finally noticed Mistress Ally, he
yanked out so quickly sissy lubricant went flying all over. Mistress
Ally had simply laughed and winked at me.

"Tommy ...," she said, "...don't let me interrupt. My sissy husband
seems to be enjoying getting fucked by that beautiful instrument of
yours. Just save some for me, will you? I know my sissy husband won't
mind you and I doing a little bouncy-bouncy. She loves sucking cum from
my twat."

Tommy smiled and rammed his cock back into me with a force that caused me
to cry out girlishly which only made Mistress Ally laugh all the harder.


* * * *

Not everything has been fun and games. As I mentioned there is real work
to be done around the mansion. True, the work is menial and mindless.
Nonetheless, Agnes and Mistress Ally insist that it be done perfectly.
Early on my devotion to my duties was not what it should have been. I
would occasionally leave a smudge on the glass, streaks on the windows
and polish residue on the wooden cabinets and furniture. The marble
floors in the entry way and the bathrooms did not always gleam like
Mistress Ally believed they should.

I pay dearly for any such slothfulness. Funny, I don't remember Ally
insisting on corporal punishment being administered to the staff when I
was still nominally head of the household. Nonetheless, not long after I
became an apprentice maid, Mistress Ally and Agnes concocted a punishment
routine for me. The routine is much like the old military ritual of
drumming a disgraced officer out of corps. First, with the entire staff
looking on, I will be ceremonially stripped of my uniform. Then, my bra
and panties are literally torn away, like a disgraced officer's epaulets
used to be torn off his shoulders. Then I am marched down to the
punishment room where Mistress Ally and Agnes have rigged up a
contraption that looked a lot like a folding ladder only was more heavily
constructed. They will bend me over and stick me through one side of the
device with my waist resting on one of the rungs. Then they will tie my
waist down and tie my hands to the other side of the contraption. The
device can then be adjusted so that I am stretched as tightly as they
want me to be. When I am thoroughly immobilized, Agnes or some other
staff member will administer a painful whipping with a leather whip or a
spanking with a large wooden paddle while Mistress Ally looks on.
Mistress Ally never personally administers the punishment because she
insists that such tasks are beneath her.

The punishment is bad in the best of situations. It is worst, however,
when Mistress Ally invites my father over to observe and in some
instances actually administer the punishment. It always makes me feel
bad that dad has to see me splayed in such an undignified manner as my
now girlishly round bottom turns bright pink and my new boobs dangle and
jiggle painfully with each swat. Of course, by this time dad has become
thoroughly disgusted with me. As far as he is concerned he has no son
(well duh!). I'm just another member of the staff, and to dad staff ...
well ... staff are just staff. He thoroughly approves of Mistress Ally's
methods and enthusiastically administers my spanking when called upon to
do so.

I remember one time Mistress Ally invited my dad to administer my
punishment when I inadvertently broke a vase in the throws of passion as
Tommy the pool boy fucked my brains out. Mistress Ally was outraged at
my lack of self-control. When dad came over she explained in gory detail
what had led to my punishment, including sharing pictures of the sordid
affair that one of the other maids had taken while I was being fucked.
Dad had long since grown accustomed to my scabrous sexual antics and said
little. The whipping, however, had been particularly brutal and I had
been crying uncontrollably when he had finished.

What had been particularly disturbing about that event was that while I
was still sobbing, I heard Mistress Ally and my dad talking.

"Oh Richard you're so manly when you discipline the maids. It turns me
on!"

Dad had laughed and given me another vicious swat.

"When am I going to be able to collect on our bet?" Mistress Ally
complained in a spoiled schoolgirl whine. "It's been five months!"

Dad huffed. "I know. I know. Believe me; it's not that I haven't
wanted to Ally. It's just that I've been so busy closing those
transactions we talked about that I just haven't had time. Besides, from
what I've heard, it's not like you've exactly been ignored."

Mistress Ally had pouted playfully. "I know Richard. But, it's just not
the same. Those deals are closed now. So, you should have plenty of
time."

Dad laughed and gave my bottom another whack. I yelped in pain which
simply made him laugh more.

"Okay, okay," he finally relented. "A bet is a bet. I'll call you later
to set something up, okay?"

"Promise?"

"I promise!"

I heard Ally squeal with girlish excitement and then silence. I craned
my head to see what was going on. All I could see was Mistress Ally
giving my dad a kiss. From my disadvantaged angle I could not be sure,
but it did not seem to be your innocent father-daughter kiss or even a
"friendly" kiss. It looked to me like one of those tongue-twanging,
butt-rubbing, crotch-stroking kisses."

Now what was that about?!


CHAPTER SIX: ME LADY'S MAID

Ally is a passionate gal and I soon forgot the spectacle of her perhaps
overzealous kiss with dad in the afterglow of my punishment. Besides,
later in the week, Mistress Ally gave me more important things to worry
about. She called me into her library and advised me that she intended
to bring a lover to the house the following Saturday and that I would be
expected to help make sure they had a good time. The emphasis she placed
on the word "good" left no doubt that she was not talking about my
serving hors d'oeuvres.

My draw dropped and my countenance fell. Everyone in the household knew
that Mistress Ally was a free spirit and that her sissy husband did not
have the backbone to stand up to her. They all knew that whenever she
had been with a lover I had been expected to clean her up in the most
degrading of manners. Yet, until now, Mistress Ally's affairs had been
conducted off premises and I had been spared the final humiliation of
having to personally entertain one of her paramours.

Throughout the week Mistress Ally let everyone know that she was bringing
over a special man to entertain on Saturday. She made no bones about the
fact that they intended to fuck like bunnies and that I would be expected
to be present to assist them throughout the weekend. She gave everyone
else except Agnes the weekend off, much to their chagrin.

Mistress Ally dragged me along shopping for just the right outfit
starting from the inside out. When a salesgirl would ask if we were
shopping for a special occasion, Mistress Ally would insist that I be the
one to explain that we were shopping for my mistress who was entertaining
a special man and wanted to look especially appealing. Then Mistress
Ally would say something like, "And my sissy husband here wants me to
look really pretty in case I get laid." This comment was usually met
first with stunned silence and then laughter. For one thing, the
salespeople had a hard time believing that I was guy. Once they overcame
this shock they found it either humorous, disgusting or a little of both,
that a man would let his wife do to him what Ally had done to me and then
let her screw around with another man, not to mention help her shop for
just the right sexy undies to do it in.

Anyway, loaded with packages from the finest women's clothiers, we went
to the beauty salon where we got our hair and nails done. This was an
experience I would normally have enjoyed. By this time my hair had grown
out sufficiently that I could wear it in all but the longest feminine
styles. In keeping with the agreement Ally had made with me and my dad,
I was allowed to go to the beauty parlor and spa whenever I liked to make
myself pretty. Truth be told I thoroughly enjoyed the pampering I
received even though most everyone knew I was a sissy. On this occasion,
however, Mistress Ally told all the ladies that we were getting all
pretty because she expected to make mad passionate love the whole weekend
and "I promised my sissy husband here that he could watch so he could see
what a manly cock looks like!" I thought some of the ladies were so hard
their heads were going to pop right out of the dryers. I turned bright
red and wanted to crawl into the nearest hole, had my hair not been in a
mass of curlers.


* * * *

When Saturday came, Mistress Ally had me attend to her every whim. I had
to run her a bubble bath. She insisted that I get out of my uniform and
join her in the massive tub where I gently washed every curve and crevice
of her body ... paying special attention to the crevices.

When I was done, she asked me to shave her pussy. I looked at her
surprised. I had trimmed her sexy thatch on many occasions. I mean
that's what a sissy maid is expected to do. Mistress Ally, however, had
always left a little hair down there and she insisted I do as well. Mine
is trimmed into a cute little heart that the girls at the beauty parlor
always get a kick over when I go in for my bikini wax every three weeks
or so.

Anyway, this time Mistress Ally insisted that she be perfectly smooth.
"I'm sure you'll appreciate it as much as I do," she said cryptically.

I was a bit nervous at first, but I managed to complete my task without
nicking my mistress' twat. I shudder to think what would have happened
to me had I done so.

When I was done ministering to Mistress' bodily needs we got out of the
tub and I began drying her off. This task took longer than you might
expect, because Mistress Ally always insists that I caress her skin
gently and slowly so as not to cause damage. We both looked down
admiringly at Ally's newly shaved pussy probably thinking the same thing:
how pretty were her newly naked fuck flaps.

"Oh Tink you do exceptional work. I think after tonight a graduation may
be in order."

Ally's comment surprised me. By graduation she meant that I would become
a full member of the staff. Such a promotion had far greater
significance than simply that I would be entitled to wear the more formal
black maid's uniform. Ally had made it clear that if I was a good maid
she would give me a nearly unlimited expense account that I could use
without prior permission for clothes, spa days, beauty appointments and
more expensive toys such as cars etc. I would still be her cuckolded
sissy husband, but I would have at least a tad of independence, as long
as I remembered my place.

"Oh thank you Mistress!" I shrieked excitedly. "I won't let you down. I
promise."

Ally laughed. "Oh I'm sure you won't sweetie. You're such a good sissy
husband. I just KNOW my friend tonight is going to love you!" I turned
to leave. "Oh and Tink?"

"Yes mistress?"

"I think for this special occasion you should wear your ceremonial
uniform."

"Yes mistress," I replied smiling with a curtsy.

* * * *

A couple of hours later I was in my room dressed in my ceremonial
uniform. The ceremonial uniform was really quite pretty. Unlike the
plain pink work tunic, the ceremonial uniform was more of a salacious red
than pink. Its sexy off-the-shoulder design allowed a hefty amount of my
now reasonably full décolletage to show. As you might expect it was also
so short that my bottom was almost constantly on display, although it was
a cute bottom if I do say so myself. For that reason, the uniform called
for a white satin thong with white lace appliqués on the front panel,
unless the Mistress ordered you to wear the somewhat childish ruffled
panties. The bodice and sleeves were each adorned with pretty white lace
augmented by a satin ribbon that was tied in a bow just below the
décolletage. White lace stockings completed the uniform.

The uniform was entirely sexy, but was not practical for much, except
perhaps to permit the guests to pinch your bottom or ogle your boobs, and
it left you entirely open and defenseless against all assaults wanted and
unwanted. As a sissy, I was particularly apprehensive about the uniform.
I looked great in it mind you. It was just that the thong panties were
just so tiny. I worried that they might not be able to contain even my
miniscule clitty should things become ... unruly.

* * * *

I finished getting dressed sooner than I expected so I sat down on the
sofa in my room. Alone with my thoughts in the quietude of the one
sanctuary still remaining to me, I pondered what was about to transpire.
Looking down at my silk and lace clad legs I marveled at what I had
become. I was a poster child for how low the lust for money and a free
ride can take you.

The whole world knew that I had lost my birthright, my position as
"master of the house" and my wife because I was not man enough to fight
for any of them. I had debased myself to becoming a sissy maid merely
because I could not handle the confrontation or threat of rejection.
Now, I was waiting nervously for a stranger to arrive to fuck my wife,
knowing that, as the sissy maid, I would be expected to make certain that
she and her lover had great sex and that would mean that I would have to
be close at hand watching as another man banged her with an ardor and
ability I could not hope to emulate.

I did it all for the promise of a free ride and a few baubles.

Then I smiled. It was more than just a "few" baubles actually.

My mind left the troubling speculation of what lay before me to dwell on
all the pretty things I was going to be able to buy with the money Ally
had promised to release to me. A free ride is still a free ride. I mean
sure not so long ago I spent thousands of dollars on clothes and boy toys
to impress the women. I had always found shopping to be comforting and
things fabricated an effective albeit thin veneer to mask the myriad of
insecurities that percolated just below the surface of my psyche. Now, I
get to spend thousands of dollars on clothes and GIRL toys to impress the
boys. Aside from the fact that there were so many more scrumptious
things to spend my money on as Tink than there had been for Brian Malcolm
Powell was there really so much difference? So what if I had been
branded a cuckold and a sissy? The insecurities were still there and the
comfort shopping afforded was still just as certain. The nice thing
about being prey rather than hunter is that prey never has to fear being
rejected or face the ignominy of failure.

I was thinking about the sale going on at Nieman Marcus when Agnes
knocked on my door.

* * * *

"Tink?" Agnes said through the door. "Mistress Ally's special guest
should be here any minute. She would like you to go out front so you can
answer the door."

I looked at my door questioningly. Answering the main door was usually
Agnes' responsibility. For whatever reason, Mistress Ally never allowed
the rest of the staff, especially an apprentice sissy maid, to greet her
guests.

"Yes, ma'am," I replied dutifully.

I left my room and meandered toward the front of the house. I wiggled
awkwardly, still not used to having my bare bottom tickled by the short
skirt of my ceremonial uniform. I absently straightened a few things to
kill time.

Then the doorbell rang.

I gulped and took a deep breath. Then I opened the door.

For an instant the world stood still. I felt my blood rushing to my head
and my face redden. I could not speak. I could not move. It was
difficult to tell where my bright red uniform ended and my pounding
breasts began.

"My, don't you look just so precious," my dad said sarcastically.

* * * *

I stood there frozen. My dad had a peculiar expression on his face that
seemed equal part sadness and cruelty. We stared at each other for
several moments before my dad broke the silence.

"I believe it is customary for the maid to invite her mistress' guests
in?"

I shook my head to clear it. "Uh ... uh ... uh ... wo ... wo ... won't
ya ... ya ... you come in ... uh ... sir?" I stammered as I stood back
to admit my father into our house. He was holding something in his hand.

Just then Ally came bounding around the corner. She rushed over
theatrically, squealing like a little girl. "Ohhhhh Poohbear....!"

She threw her arms around my dad and kissed him deeply. She made a point
of maneuvering them so that I could watch their tongues dancing with each
other before she reached down and cupped my father's crotch. It was
obvious that he was excited. Even while she kissed him, I could see her
smiling at me wickedly.

"Oh Poorbear," she cooed when she finally broke the kiss. "I've missed
you so much, especially 'Big Jake' here. It's been so long since I've
been fucked by a real man.

"I've missed you too Ally," dad replied breathlessly and then reached
beneath her skirt and began to caress her right in front of me.

"Oooooooo Pooh I can't wait to have you inside me again!"

Again?

Dad produced the bottle that he had been holding behind his back. My
mouth dropped. It was his bottle of Henri IV Dudognon Heritage cognac.
He never took that precious decanter out of the house. Given its cost he
should have had security guards on either side of him. He merely handed
to Ally as though it was nothing more than a bum wine in a brown paper
bag.

"This is such a special occasion. I thought I'd bring something smooth
and silky to go down our throats." He looked at me derisively. "Perhaps
your ... GIRL ... could pour us some."

Ally looked at him slyly. "I hope you'll put something else warm and
silky down my throat Pooh," she said huskily. "Let's go into the living
room. Shall we?" She waived at me dismissively. "Tink, why don't you
go and pour your father and me some cognac like a good sissy maid?"

I crimsoned but did as instructed. I spent several minutes gazing at the
$2 million dollar 24-karat gold-dipped and diamond-bejeweled bottle. My
father had never let me even touch the bottle before. How ironic it was
that only in my capacity as a sissy maid was I being permitted to handle
the rare flask so that I could pour him and my wive a snifter of the
unique liquid to warm them up for an evening of hedonistic fornication.

There were tears in my eyes as I carefully poured two snifters of the
fiery smooth cognac. I put them on a silver serving tray and gingerly
carried them beside the precious bottle into the living room.

When I arrived I almost dropped the entire tray. My dad and my wife were
embraced on the sofa. His shirt looked like it had been nearly torn off
of him and tossed across the room. Ally's blouse was lying in the
opposite direction. Ally's bra was askew and dad was hungrily lapping on
her nipple while his hand was snaking its way up her skirt and into her
flowery panties. Ally's head was resting against the back of the sofa.
She was moaning and caressing my dad's head.

I thought I could take it, but this was too much. My tears flowed as I
set the tray down on the coffee table. "Why?" I sobbed.

Upon hearing my sobs, the two lovers took a break from their amorous
frolicking. They gazed at me as though my question was ridiculous. They
exchanged glances and snickered.

"Why?" my dad parroted while eying me unsympathetically. "Well, for one
thing, I always thought your wife had the most delicious titties...."

"Oh Pooh you're so sweet," Ally replied while watching my expression.
"Tink don't look so forelorn. Poohbear ... uh ... your dad ... and I
have been having an affair since before you and I were married. He's
such a man; so unlike you sweetie. You could never satisfy me that way.
You know that. You've got a sweet tongue, but you're just a sissy. You
always were."

I gawked at the two of them. I was stunned, confused and hurt. Dad
ignored my reaction and resumed absently stroking Ally's nipple causing
her to giggle girlishly. Garnering the little backbone I had, I cried
out through my tears, "Then why the fuck did you even marry me? Why
didn't you just marry dad. He has all the money anyway."

Ally pushed my increasingly persistent and impatient dad away and reached
for the cognac. She handed a snifter to him and took a sip. She held it
in her mouth and swirled it deliberately before swallowing slowly so that
she could relish the buttery warmth of the fiery fluid as it flowed down
her throat.

Eying her snifter analytically, she continued. "Honey it's simple. I
wanted the money sure. But, I also wanted respectability. If I'd
married your dad, I would have looked like a golddigger. I knew I could
marry you and have your money and your father both. I always pegged you
as being nothing more than a lazy, spoiled, freeloading sissy. There was
never any doubt in my mind that once we were married and I controlled the
purse strings I could control you. I figured it would take a year or two
then your dad and I would figure out some way for you to 'disappear' and
then we would get married. By that time we would be financial equals and
our age difference would mean less. On top of that, if my plan worked
and I succeeded in becoming the company's largest shareholder, as I did,
it would actually look like your dad married me to regain control of the
company."

"Make me disappear?" I shouted.

Ally looked at me sternly. "Now Tink I know this may be upsetting, but
remember your place. You chose to be there wearing that cute little
uniform. I bet that pathetic little dick is twitching in those adorable
satin panties even as you're standing there. Isn't it?" I crossed my
legs self-consciously, confirming her supposition. "Anyway, we weren't
going to kill you or anything. Your dad, bless his little heart, would
never have allowed that. In fact, at first he could not believe you were
a sissy. Oh, you were certainly disappointing. But a sissy? I
convinced him to let me bring out the real you. We made a little bet.
Your dad lost. That's why you're standing there so cute and feminine
with boobs almost as big as mine and an ass that's always ready for a
cock. That's why you're a sissy maid instead of an underachieving
executive. And, that's why we're here tonight. I bet your dad that you
would do anything for a free ride. I bet him that you weren't even smart
enough to know that there's no such thing as a free ride. The moment you
had your breast implants your father conceded defeat. So, tonight, I get
to claim my prize: your pride down to the last ounce of dignity." She
took a sip of cognac and closed her eyes to savor her triumph as much as
the brandy.

I looked at my dad and whined plaintively. "Dad how could you let her do
this to us?"

He met my whines with a sneer. "What exactly did I 'let' her do to US?
Ally has increased the size of the trust fund principal by over a third.
She's increased the company's profits by two thirds."

"But dad, you let her take the company from you! You built that
company!"

Now dad laughed. He too took a sip of cognac and savored it. He looked
at Ally. "What makes you think I let her take the company from me? Do
you really think I didn't know what the little minx was up to? I've been
using blind trusts and what not since she was in diapers."

Ally looked at him in surprise. I could tell that she really had thought
that she had pulled one over on my dad.

"Look, by going around my back, Ally paid a what, twenty-three, twenty
four percent premium?" Ally nodded sheepishly. "So what did I give up?
I made a twenty-three percent premium on a sale of roughly thirty percent
of the company. The container business is huge but the margins are thin
and the upside potential limited. I had my eye on two other companies
for a couple of years now that have a much higher upside but I didn't
have the cash. Ally's maneuvering gave me the cash I needed to acquire
those companies. Believe me they are keeping me busy and I haven't had
so much fun since I founded Powell Container. On top of that, thanks to
Ally's splendid management, my remaining twenty-two percent interest in
Powell Container is making me nearly as much as my controlling interest
made before I sold it. And, as for control itself, first Ally and I talk
about every major decision impacting the company. Don't we pumpkin?" He
brushed his finger against Ally's nipple and she giggled. "But, let's
assume, just for argument's sake, that Ally tried to do something that
would hurt my interests. Well, while it is true that Ally is indirectly
the largest single shareholder she does not own fifty-one percent of the
company. I own the next largest block of stock and my friends own most
of the rest. With a few phone calls and calling in a few favors, of
which I have an ample supply owed to me, I can block almost anything she
tries to do that I disagree with. So, you see, I still pretty much
control things if I want to.

"So, I have the money. I have the companies I want. Most importantly, I
have the girl! Who exactly did what to whom?" He smiled slyly and took
another satisfied gulp of cognac.

Ally and I both looked at dad. We had both been played by a maestro. We
had been dancing to his tune since the beginning. I had to hand it to
him he was a hundred times the man I could ever hope to be. In my heart
I grudgingly conceded that he deserved a gal like Ally far more than I
did.

Dad allowed the last of the cognac to flow down his throat. He then
pompously placed the snifter back on the tray with a loud clink. He
looked as if he was reconsidering something.

"Well, I guess I DID lose the bet. I bet Ally that you were man enough
to stand up to her and ask for a divorce rather than be turned into the
precious little sissy you are now. It's one of the few times in my life
that I've misjudged someone so thoroughly. I must admit you are an
adorable thing. If you weren't my son, I wouldn't mind popping you
myself. Decorum prohibts me, however. Anyway, this was one bet that I
would win either way. You see, if I won, Ally agreed to sell me back
half of the stock I sold to her at the same price she had paid for it.
That stock right now is worth thirty to forty percent more than she had
paid for it so I would have made a fortune. If I lost, however, I agreed
to come here and make love to your wife while you not only watched but
also assisted. Either way, the plan is for me to move in for Ally and me
to get married once we figured out a way to make you disappear, in a
figurative sense of course. You get to keep your access to your trust
fund and you get to stay on as a sissy maid. It's the least I could do
for such a pathetic whimp." He cackled evilly. "Besides, I've found
that it's so hard to get good help these days!"

"Ohhhh Poohbear...," Ally cooed seductively, "... you're such a MAN!"

* * * *

Ally grabbed dad's crotch appreciatively signalling that explanations
were over. She kissed him and I watched as their tongues danced. When
she came up for air she breathed, "Oh Pooh take me ... please. I need
your cock inside me!" I crimsoned upon hearing my wife's horney plea to
my own father. She smiled at me evilly and said in a syrupy voice.
"Tink, tell your dad that you want him to fuck me, that you want him to
stick his big fat cock inside your wife and make her cum over and over.
Tell him you want to watch. Tell him you ... want to help!"

I looked at her horrified and humiliated. I was sobbing uncontrollably.
I had brought this all on myself.

"TELL HIM!" she shouted.

"Da ... da ... dad ... pa ... please fuck Ally. St ... stick ... your
... cock ... inside her and ma ... make ... her ... cum." I choked on
my words as much as on my tears and paused.

"Go on," Ally demanded unsympathetically.

I looked at my dad and through my tears sputtered, "Pa ... please ... da
... da ... dad ca ... can ... I ... wa ... wa ... watch you ... fu ... fu
... fuck my ... wife? Ca ... ca ... can I ... ha ... ha ... help you ...
fa ... fa ... fuck my wife?"

Dad flashed a scornful grin while shaking his head. There was almost
sadness in his voice when he said, "I really never thought I would see my
son sink to this depth. Maybe we really should just make you disappear
and put you out of your self-inflicted misery." He laughed at my
horified expression. "Do you really want me to fuck your wife while you
watch?" I nodded my head in humiliated acknowledgment. "I asked you a
question ... DEAR!"

"Yes dad I really want you to fuck my wife while I watch."

"And do you REALY want to help me fuck your wife like a dutiful sissy
maid?"

I looked at my dad. I also could not believe that I had sunk to such
depths. Yet, the die had been cast long before this. I had sold out.
My dad had gotten what he wanted. Ally had gotten what she wanted.
Truth be told, I had gotten what I wanted. It was certainly humiliating
to be standing here knowing that I would soon be watching my dad screw my
wife while I helped. But, the fact was if it had not been my dad, I had
known all along it would have been another man. I had sold my soul for
what I had thought was a free ride. But, Ally was right. There is no
free ride. My desire to live the high life without ambition and without
work had cost me my pride and my dignity. Ally and dad stood smirking at
my contemplative expression. They thought they had gotten the best of
me. I could understand why they would think so. Yet, in my heart I knew
I was pathetic. What was my pitiful pride or vacuous dignity worth?
Frankly, on a comparitive basis I had gotten by far the better deal.
Rationalization perhaps. Nonetheless it allowed me to stand up straight,
wipe away my tears and say with resigned determination, "Dad I REALLY
want to help you fuck my wife like a dutiful sissy maid!" I took
perverse, if misplaced, pleasure in their stunned expressions.

* * * *

As we retired to Ally's bedroom, stripping clothes as we went, I thought
I had achieved a psychological victory of sorts. Yet, I was not prepared
for just how humiliating my participation in my dad's copulation with
Ally would be.

It began with my being required to help Ally finish getting undressed.
When she was naked, dad hefted her playfully over his massive shoulder
and deposited her onto what had been our bed. He positioned her on her
hands and knees.

"Tink, please get your wife ready to take my big thick cock."

"What?" I asked.

"Get over here and slide under and get her ready for my cock. Certainly,
you've seen the size of my cock in the shower, and that was before it
gets excited. You're going to want to get your wife ... well I guess
mistress is a better term now ... plenty wet for me!"

I was stunned for a minute, but quietly climbed onto the bed and slid
beneath my wife. My dad leaned over and spread her pussy lips wide. I
knew why he was going through these antics. As I began lapping at my
wife's pussy he and I were only inches apart looking at each other:
debased sissy son getting his wife's pussy ready to accept his manly
dad's bulging member. I could not help it, I began to weep as our gaze
conveyed the unspoken reality that with each willing lap of my tongue on
my wife's steamy twat I was wiping away the last vestiges of father and
son relationship. What we would become to one another I was not yet
sure. As of this moment, however, I was nothing more than a sissy maid
arousing her mistress to please another man. I was grateful that Ally's
prodigious gynecic glycerin coated my face and masked the tears that
again came to my eyes. Having convinced myself that this was all for the
best for everyone, I was not tearful over my own fate as I was saddened
that had let my dad down.

My sorrow did not detract from my vigorous licking, flicking and lapping.
In only a few moments Ally was moaning. "Oh Richard I TOLD you she had a
great tongue!"

Dad released Ally's twat and let me continue licking and slurping while
he finished getting undressed. By the time he returned Ally's legs
glistened with her sexual unction and she was ready for my dad ... her
lover.

To my surprise dad did not take Ally doggy style or even climb on top of
her missionary style. Instead he lay down and pulled Ally on top of him.
I had never watched my dad have sex before, but I knew enough of his
personality to know that he was not a "bottom" type person, a position
usually viewed as submissive, if not subservient. At first I thought
that it might have something to do with his having lost the bet.

Their intent became clear however when Ally looked back over her shoulder
and commanded me breathlessly, "Tink put your daddy's cock in me ...
now."

I gasped. It was one thing to get Ally ready to receive my dad's cock.
It was another thing entirely to have to actually assist him ... to touch
him ... to personally insert his powerful member into my wife's pussy. I
stared at the engorged organ poised at the entrance to Ally's pleasure
cave. At that moment it looked beautiful and terrifying and altogether
gorgonizing, like some exotic reptile loosed from its cage at the zoo.

"Well, just don't sit there!" dad groaned. "Put it in Tink!"

Gulping to swallow my shame, and grateful that at least they did not make
me get HIM ready to fuck my wife the way they had made me get Ally ready
for him, I grabbed hold of dad's love snake. It was hot in my hand,
pounding with the powerful rhythm of dad's heart as it beat furiously to
meet the demands of his inflamed lust. It was hard. It was huge! I
could hardly get my tiny effeminate hand around it. I had to give him
credit; dad's beaver cleaver really was massive. Compared to him my
little weenie really did seem more like a clitty. No wonder Ally had
wanted him inside her!

For the briefest of moments I confess that I contemplated what it would
be like to have that gorgeous hunk of flesh inside me, pounding my sissy
ass into submissiveness. I quickly banished such thoughts for fear of
where they might lead. Instead, I pointed the rigid flesh toward my
wife's soaking aperture to bliss and guided it to its destiny. My
humiliation was complete and perfect as I watched its massive bulbous
head part Ally's slimy pink lips and sink into the sanctuary that should
have been reserved for her husband ... for me.

I understood then the cruel symbolism behind their insisting that I put
dad's cock into her. By doing so, I was relinquishing any title, any
claim, any right to ever again enter my wife's love chancel, and, of my
own volition, was declaring dad to be Ally's high priest in my stead.
The moment the angry purple head disappeared into her I was no longer
Ally's husband and she was no longer a cheater.

I sobbed softly while I watched dad and Ally passionately fuck, for that
was the only thing you could call it really; there was very little love
in the act. There was only hunger and need, power and vulnerability,
invasion and surrender, fury and frenzy.

Ally came three times before dad groaned loudly and propelled his male
essence into her womb marking her as his and his alone. Dad was not
through. He almost threw Ally off him and then took her missionary
style. There was nothing subservient about him now. Ally seemed to
relish his aggressiveness and mewed in submissive recognition of the raw
masculinity lying on top of her. Yet there was an aura of egalitarianism
to their coupling as though each was acknowledging the other's importance
to the relationship. Again I counted three powerful orgasms from Ally
before dad again came inside her.

I looked on in awe and Ally gasped appreciatively as dad gruffly yanked
her onto her hands and knees. He was barely breathing heavily and from
the looks of things his love tool was merely getting honed. This time he
almost brutally rammed his now glistening love bludgeon into her ass.
She howled in both pain and protest. There was no semblance of equality
this time. Dad was fucking his bitch. I smiled with some satisfaction.
If Ally entertained the notion that she was my father's equal, he was
pounding that fancy out of her with each savage primal plunge into her
unwilling bum. She came deeply and heavily in grudging acknowledgment of
his superiority. Then she began to meet his powerful thrusts with
thrusts of her own letting him know that while she was willing to be
submissive in the pursuit of her own pleasure she could give as well as
she could take. Her voluptuous ass seemed to almost swallow dad whole.
The two of them grunted, shrieked and moaned. Then in perfect chorus
they came together and dad finally collapsed onto his prize.

They lay entwined with each other saying nothing while their bodies
engaged in some type of orgasmic discourse. Dad's satiated gasps seemed
to declare that while Ally would never be his equal, she was a woman
worthy of him. Ally's still palpitating pussy and ass seemed to pulse in
reply that, unlike me, dad was a man worthy of her.

Dad got up and knelt beside Ally. Ally got on her hands and knees. Then
she beckoned me.

"Tink please be a dear and clean me up. Your dad is such a virile man.
I can feel him leaking out me everywhere!"

I dutifully got on the bed and assumed the prone position Mistress Ally
had taught me. As she had so many times before she turned and lowered
her gooey pussy and ass toward my lips. I could see my dad's cum leaking
from Ally's bottom. There was nothing more to do. I closed my eyes and
stuck out my tongue. I felt Ally squeeze her ass and my dad's seed began
to flow out her sexy bottom across the great divide and onto my tongue.

It was finished.

I was and henceforth would be nothing more to either of them than a sissy
maid existing for their pleasure and their pleasure alone.


CHAPTER SEVEN: GRADUATION

The following day dad made arrangements to move in with Ally. They sent
me to San Francisco where I underwent rather extensive cosmetic surgery.
When I returned a month later no one would have recognized me. My face
had been given a distinctly feminine quality to it and my Adams apple had
been shaved such that I had a significantly higher, more feminine voice.
Ally paid for finishing lessons that helped me perfect my female voice
and mannerisms. By the time she was done with me I was more woman than
man. The change was so dramatic that when I ran into Mark Johnson at the
mall after I had returned he did not even recognize me. Richard Malcolm
Powell, Jr. had, as my dad and Ally promised, effectively disappeared,
leaving them free to marry once a few legal odds and ends were cleared
up.

I now have a Master and a Mistress. I still participate in their sex
life occasionally. Ally especially continues to enjoy my personal
cleansing services. Nonetheless, neither of them goes out of their way
to humiliate me. They merely treat me as a sissy maid, a position with
which I am contented.

Ally rewarded me for my dutiful performance that Saturday night with a
promotion to a full staff position. For now, I am Mistress Ally's Lady's
maid, a staff position second only to Agnes and in many ways more
important and intimate. In recognition of my achievement, I was
presented with a standard black and white maid's work uniform and an
exquisite ceremonial uniform. The ceremonial uniform was replete with
all manner of lace and a delightful tulle petticoat with ruffles that
made my uniform stand out more than the other ceremonial uniforms.

With my uniform, Master and Mistress also gave me an opportunity to wear
it. They threw me a "graduation" party. I had such a good time!
Mistress Ally had it catered so that all of the other staff could be
there, including Tommy the pool boy. Master and mistress also invited a
dozen studs to the party who had but one instruction: fuck my brains out.


Although I ought to have been used to it by now, I was still a little
self-conscious at having my sexual hunger displayed so publicly.
Mistress did not hold it against me. She and Agnes simply plied me with
a half dozen Cosmopolitans and then gently but firmly led me over to the
sofa and sat me down. Mistress pulled my panties to the side and
signaled Tommy the pool boy over to have the first go. Before I knew it,
Tommy had planted his twat twanger in my sissy chute and was fucking away
while I held my legs wide for him.

It did not take long for me to forget the crowd of well-wishers cheering
me on. My own moans and passionate shrieks drowned out the cheers and
laughing banter surrounding me, including Master egging Tommy to pound me
harder. Like a good sissy, I came fairly quickly after Tommy entered me.
By the time he came my little sissy clit was hard again. Well, as hard
as it ever gets any more.

My first high-pitched orgasmic ululation broke the ice so to speak. In
no time I was not only welcoming guy after guy to use me in any way he
wanted, I was almost begging them. When one guy would finish I would lie
there on the sofa with my panties pulled to the side and my well used
sissy hole gaping invitingly. I would coo "Next?" and within moments
another burly dude would have his thick manly meat buried deep within me.


I'm not sure how many men had me that night. I stopped counting at ten,
but there were more. As a sissy I was especially gratified that several
came back for seconds. By the time the evening ended there was a steady
stream of cum flowing from my well-used ass and my tummy was filled with
at least a quart of the stuff that I consumed from sucking off those guys
who were impatiently waiting their turns at my little brown jug.

* * * *

Following my graduation party my life began to return to a normal
routine. Dad has gradually come to accept me as the sissy maid I now am
inside and out. Consequently, our relationship has taken on a somewhat
distant character more befitting a maid and her master.

Oh, dad remains a flirt mind you. What man isn't? I will be trying to
do my work and he will come up and give me a kiss on the cheek as a
reward for "good service." When he does, however, he never fails to give
my now prodigious boobs a playful squeeze. He loves to see me jump and
shriek girlishly while turning a deep red.

It is all very platonic. I'd be lying if I told you I did not fantasize
about having dad's huge hunk of man flesh buried deep in my bottom. If
you asked him when he was drunk, dad would probably tell you that he too
often fantasizes about doing his sissy son. We both know though that it
can never be. It is the only thing missing from an otherwise perfect
Master-Sissy Maid relationship.

Moreover, although I have graduated to full staff, I am still considered
fair game. I think Ally believes that it is a sissy's inherent nature to
be promiscuous and that it would be cruel to deny me. Therefore, she has
made an exception to her otherwise strict rule against staff
fraternization. I am effectively the household sex toy. I don't mind.
Whether or not it is in all sissies' natures to be promiscuous, I know it
is within this one's.

As a result, Tommy the pool boy continues to hover around me every chance
he gets like a hummingbird around an orchid. It seems like almost every
other day Tommy and I go through our little charade. He makes an advance
and I pretend to be insulted. Then we end up on the floor or the nearest
bed going at like bunnies.

* * * *

Tommy provides comic relief to a life that has recently become
complicated and promises to become more so in the too near future. You
see while I was getting my brains fucked out at my graduation party,
Mistress and Master were having their own bit of bouncy-bouncy. Of
course a sissy can't get pregnant. Mistress could and did. Master and
Mistress are going to have a little girl who they have promised to name
Briana ... after me ... or the former me!

Being a typical macho man, Master is ecstatic and brags all the time.
What sixty year old man would not be cocky after fathering a child at his
age with a sumptuous woman half his age? Mistress is more reticent. It
is not so much that she does not want the pregnancy as it is that she
views having a child as being ... inconvenient. She is still singularly
committed to getting ahead and proving her superiority in a male
dominated business world. On such a quest a baby at one's breast could
be ... distracting.

Early on this inconvenience posed a real dilemma for Ally. Then she once
again proved her genius in solving thorny problems. She decided that we
would get another maid to take over most of my daily responsibilities and
that I would become Little Rachel's amah and nanny.

So, about three weeks ago Mistress and Master brought home another
apprentice sissy maid from the office. I don't know Kristina's entire
story. I gather however that she had been hired to be Mistress'
executive assistant and then Mistress caught her passing trade secrets to
a competitor. Evidently, Kristina had to make some choices too and chose
sissidom over whatever alternatives Mistress might have offered. I
shudder to think what those alternatives might have been; Mistress is not
someone who suffers treachery well.

This is seen in the fact that Kristina's life is not nearly as easy as
mine. She does not have access to the large trust fund with which to go
shopping or pamper herself with a spa day whenever she feels like it.
Not that it would matter if she did, because Master and Mistress usually
keep her in the punishment cell down the basement when she is not doing
house work. I often hear her cries through the register vent in my room.
I have become quite adept at discerning when she is screaming from a
spanking and when she is being used by Master or Mistress. Both occur
with disturbing frequency and both sound similarly ... uncomfortable.

I don't think Kristina knows that Master is my dad and Mistress Ally used
to be my wife. Yet, as I am sure you can imagine, given my obvious
closeness and fierce fealty to Mistress Ally, Kristina and I are not the
closest of friends. Nonetheless, we are both sissies and that
necessarily foments and fosters a camaraderie that only sissies can
share.

When I am not busy tending to some special personal need of Mistress
Ally, Kristina and I frequently do housework together. Sissies being as
we are, and with our clitties so accessible and prone to "slipping out"
of our tiny thong panties, ... uh ... diversions ... are inevitable.
I'll say this about Kristina, whatever her shortcomings as an executive
assistant, as a sissy she sure is creative. I never knew how many things
you could do with a humming, vibrating vacuum cleaner.

* * * *

As for me, shortly after she decided that I should embark on yet another
career path, Mistress Ally sent me to a doctor who specializes in female
reproductive matters. The doctor she started me on some experimental
medications to enlarge my breasts and induce lactation. She also removed
my breast implants saying that they could impede my development.

The drugs have worked as advertised. My breasts have grown at an
alarming rate. I have gone from a pert 36B immediately after the
implants had been removed to a current prodigious 38D. The doctor says
that by the time Rachel is born I could be a DD or even an E cup. More
importantly, to almost everyone's delight, three weeks ago I began to
produce milk. The doctor ran some tests and has reported that my breast
milk has all of the nutrients that a hungry infant will need and there
are no harmful trace elements in it.

That's all great I guess. Still, before I learned about nursing pads for
my bras it was embarrassing to look down at my blouse and see that I had
leaked. It was like those mortifying mornings when I was a boy and mom
would wake me up and point out mirthfully that I had had a wet dream.
Now, my motherly springs are more than simply embarrassing. The doctor
has said that, with my milk having come in, I have to exercise my glands
so that by the time the baby comes I will be producing enough milk to
feed her. I don't know if that is true or not, or whether Mistress is
just having fun with me (she's such a kidder sometimes). Regardless,
twice a day I have to literally milk myself like a damned cow. Kristina,
and of course Tommy the pool boy, have offered to help me. This is one
task though that I would just as well do myself, thank you very much.

Sitting in the privacy of my room milking my titties into a big plastic
bowl has given me a lot of time to think. Like Mistress Ally I have
mixed emotions about the whole thing.

On the one hand, Ally's pregnancy and my impending role as a wet nurse
have given rise to exciting new diversions. You would not believe the
cute maternity bras that are now available and the girls at the salon are
just giddy over my impending new role. They have invited me into a
sorority of which I never dreamed I would ever belong. I have found that
motherhood, even surrogate motherhood, induces a natural conviviality
that not even sissies can match. We talk about breastfeeding and
motherhood in general and all of the responsibilities it entails.

And therein is the rub. As I watch the life sustaining milk shoot from
my nipples into the bowl, I realize that Master, Mistress Ally and most
importantly little Briana will all be counting on me. I shudder in awe
when I ponder holding Briana's precious tiny life in my hands and guiding
her needy puckered lips to my nipple. It makes me cry to think how I
will react when her beautiful eyes look up to me as she suckles on my
breast taking for granted that I will give her the sustenance to grow.
Her life will be in my hands, will be my responsibility. It is a
breathtaking burden, far greater than any of the responsibilities that
until now I have done anything to avoid, even to the point of allowing my
wife to turn me into a cuckolded sissy who is soon to be the wet nurse to
a baby born to my wife, fathered by my father and who will technically be
my half-sister.

Yet, as Ally and I sit on the sofa and I caress her swollen tummy heavy
with life, a life that in a very real sense will be mine as much as hers,
I cannot help but think that I have finally found a responsibility that I
do not want to run away from, even if I could. I'll not forget that
moment on the sofa when I realized for the first time that this precious
life will be mine to raise, not because I gave birth to her, but because
I chose to accept the responsibility so that Ally could devote herself to
her career and getting ahead. That realization engendered sensations
that I had never felt before: pride in who I am and determination to make
this precious life something more, something better than I.

I feel tiny Briana kick and look at Mistress Ally and I wonder ...

... who is the one really shunning responsibility now?

SissifierXL 7000

By: Wendy

May I submissively beg the attention of all voluptuously masterful
Mistresses, exquisitely dominant Dominatrixes, less than tolerant
superior Wives, beautiful proud Women of all ages, and groveling,
misbegotten mistakes of manhood who are lower than low and bound to be
known as supercilious Sissies for all time.

My loving, caring, charming Mistress has commanded me to announce the
availability for immediate sale and delivery, the product you have all
been hungering for. (Well, maybe not the Sissies.)

After strenuous testing (on me) and many extremely painful (to me)
trials and errors in construction (by me), at last my Mistress is proud
to present the SISSIFIER XL 7000!

Mistress demands that I humbly describe this wondrous machine and it's
many many painful, humiliating, and degrading features.

Allow me, Worshipful Women, to explain and describe this remarkable
machine to you.

The SISSIFIER XL 7000 comes in two intimidating parts.
1. The Base and Head Compartment Unit.
2. The Application Unit.

Picture, Ladies, if you would be so kind, a stainless steel base,
somewhat similar to a restroom commode, resting on a four foot square
stainless steel platform which rises about five inches off the floor..
The stainless steel seat is oval like a toilet seat with the same oval
hole in the seat as you would picture. But the seat is covered with 120
sturdy hard rubber pegs, about 3/4 inch high and the diameter of a
pencil eraser, spaced about 3/4 inch apart, all over the seat. The seat
hangs out over the base as does a toilet seat. On the base platform are
leather bondage straps at toe level and on the front of the base are
leather bondage straps at upper ankle level.

Built into the stainless steel bowl of the base, allowing for
protrusion up through the oval hole of the seat is a hydraulically
dynamic powered vibrating ceramic dildo which is capable of not just
penetrating and vibrating but also thrusting at low and high levels, of
both pressure and speed. Looks like a head of a snake, poking it's
dangerous head out of the bowl of the base. The SISSIFIER XL 7000 comes
with three interchangeable dildos. One is smooth ceramic. One is
stainless steel with spiraling ridges. The third is hard rubber with
small bumps all over.

Mistress gets her choice. The Sissy does not.

At the back of the base rises a stainless steel back column at a 70
degree angle out from the base. The back column also is wickedly tricked
out with the same hard rubber nubs which are on the seat. It is about
three feet high, which would be about the top of the occupant's back.
This allows the occupant's head to be unsupported. There are bondage
straps at lower stomach level and at just below the bust line. Coming
out, at an angle, as arms from this column are two, three feet long,
stainless steel arm pieces which have bondage straps on both arms at
wrist level and at bicep level. The same hard rubber pegs are also on
the arm pieces. When installed in position the occupant is spread out
totally and exposed to whatever his mistress desires. The addition of
the rubber nubs gives no chance for the occupant to have any painless
support to any part of his torso and arms.

Coming out from the back of the column and then rising above what would
be the head level of the occupant, is a large, frightening, extra
powerful stainless steel torpedo style salon hair dryer. The dryer's
helmet is positioned to be lowered completely onto the head of the
occupant. The dryer does have a neat special feature. Around the head
opening of the dryer helmet is a Lycra vinyl shield which can surround
the rollered head of the occupant and can be pulled to a sealing
tightness with elastic draw strings which will allow very little heat to
escape the helmet of the dryer. This is not your Grandmother's hair
dryer.

That completes the description of the Base and Head Compartment Unit.

I will now describe the Application Unit.

The Application Unit is maneuverable and rises in front of and over top
of the occupant of the aforementioned Base Unit. The Application Unit is
powered by a large motor and a high capacity compressor. From the
Application Unit, at about the level of the occupant's groin, a wide
diameter suction hose with an attached eight inch long vacuum sheath
extends for four feet. This attachment resembles quite closely a high
volume professional dairy udder teat milker.

At the level of the occupant's chest are two suction hoses with their
attachments of 5 inch diameter ceramic suction cups with rubber rims for
total sealing. Inside the cups are nipple clamps which can be attached
to the nipples and pulled to any desired pressure and length by a turn
of a dial.

At about the level of the occupant's face, there is a large suction hose
with a suction device of a rectangular shaped three inch long sheath.

At the level of the occupant's nose there is a small hose from the
Application Unit with nose oxygen nodules for delivery of gaseous
humiliations.

All together the two units present a rather formidable device, designed
to instill fear and awe in those who are chosen or desire to become one
of the "occupants"

Mistress now desires that I inform you how the machine is best used for
it's intended purposes of and humiliation and punishment.

For best results, please use this method:

(I have been through this method and can guarantee it's effectiveness)

(Mistress laughs)

The Sissy, for that's what we are dealing with here, should be told to
remove whatever form fitting sundress or wet diaper he may be wearing
and to stand quivering, naked without even a bra to cover his shame. He
should assume the posture all sissies are taught, by having his wrists
limp at the level of his breasts.

The Sissy is then instructed to put on the 4 inch high heeled black
patent leather stiletto pumps which come with the SISSIFIER XL 7000.
Thigh-high sheer Midnight Black hose are optional but very lovely. If
you have a newbie sissy, then white cotton anklets, with little silver
bells, are suitable.

The Sissy, wearing only the pumps, is to proceed to the professional
beauty salon in your home (you all have one, don't you?) and then beg to
have his hair washed and then rolled wet on medium steel prickly brush
rollers. Rolled very tightly. The rollers must prick the scalp. At least
30 rollers should be used both for maximum curl and maximum tightness
and uncomfortability. And they look really cute on a prissy guy.

The Sissy is then told to sit at the make up vanity. He is told to apply
very heavy black eyeliner and black lash extending mascara and brush his
plucked brows into a startled configuration. His eye shadow (deep blues
and lavenders) is to be applied as if he were trying out for the role of
Cleopatra at a transvestite nightclub. His lips must be perfect. Crimson
lipstick, topped off with a scarlet lipgloss containing highlights of
gold sparkles is the preferred prescription. The sissy is to form a high
bow on the upper lip and apply womanly fullness on the lower. Three
applications are the sissy norm. Be sure he kisses the open shaft of the
tube of feminine perfection before each precise application.

The SISSIFIER XL 7000 supplies to each customer a special pair of
earrings for use in conjunction with the preparation of the occupant.
After application of his make up comes the time for the sissy to fasten
on his new earrings. These lovely earrings are a 1-1/2 inch diameter
silver heart, hanging from a three inch mesh silver chain, for pierced
ears of course. The stud is stainless steel with a small ruby on the tip
of the stud. The heart is sterling silver, plated over 8 ounces of base
lead. They look divine, and are intrinsically evil. Ask the occupant
after about ten minutes of these earrings swinging from his tender
earlobes. Poor dear.

He is now ready to face the SISSIFIER XL 7000.

The Sissy, with his rollered hair still wet and rolled tightly, is told
to position himself, painted face out, standing on the steel platform at
the base of the SISSIFIER XL 7000. The back of his 4 inch heels should
be touching the front of the pedestal of the base. The Toe straps will
then be secured, binding his toes to the stainless steel floor platform
of the SISSIFIER XL 7000 and then the high ankle straps will be fastened
tightly to the base. His feet will now be immobile and several inches
back behind the outcrop of the seat. It will be very difficult for the
occupant to stand in this position for any length of time.

The Sissy will now be instructed to slowly lower himself part way down,
over the oval opening in the seat, holding his butt cheeks separated by
the use of both hands. It is very hard to maintain this position. Some
training may be needed before installing the occupant in the SISSIFIER
XL 7000. At this time hydraulic dildo will be electrically extended and
insertion will take place into the sissy's inadequate vagina. Some pain
may occur. Good. The sissy standing in this half down position while
being penetrated will provided a lot of laughs. It may take two or three
aimings to achieve initial, medium to deep, penetration.

The Sissy, after initial penetration, will immediately be told to sit
down HARD on the base seat.

As a result of this action the dildo will make it's final adjustment
within the pussy's pussy. Sitting down hard on the dildo will ensure
maximum penetration. This may provoke a gasp and a cry from the
occupant. Look for some blood leakage.

The sissy will now have put his full weight on the hard rubber nodules
which cover the seat. The hard rubber nodules do not like to be sat
upon.

These will fight back, with a vengeance. The sissy will know that he is
in a fight. The sissy will not win.

(Let me say at this time that for the most benefit and satisfaction, a
circle of four or five SISSIFIER XL 7000's, with their would-be
occupiers standing at attention at their machine's side, allows the
unwilling participants to view what is to happen to them and to hear the
lovely groans and whimpers coming from each sissy as they are installed
in the SISSIFIER XL 7000.)

The Sissy will now struggle against the dildo and the terrible pain of
the hard rubber nodules trying to pierce his buttock.

The Sissy will now be pushed back against the 70 degree slanted back
structure. By being placed on the slanted back column, the occupant will
be placing even more pressure on his butt cheeks. The rubber pegs will
press into the skin even further. The occupant will now have the stomach
and underbust straps securely tightened and also the four wrist and arm
straps will pin the occupant firmly to the SISSIFIER XL 7000. The
restraint straps being tightened will, of course force the occupant to
tightly encounter the hard rubber pegs on the back column and the arm
supports. Sissies are meant to be secured, usually by the harshest means
possible. They really like it.

The Sissy will now feel the imagined weight of the Stainless steel
torpedo salon dryer being lowered over his rollered head. What a fearful
sight. Because the occupant is now positioned on the slanted back column
with his head unsupported, he will have to keep his head pitched
somewhat foreword in order to allow the dryer helmet to position itself
properly on his rollered head. The insides of the helmet will naturally
brush against the prickly rollers on the sissy's head. Until it is
positioned correctly, and it will never be because the occupant is
constantly struggling to keep his head in the proper position, the sissy
will experience a great deal of scalp pain.The Lyrca vinyl shield will
be snuggly secured across his forehead and over his ears and around the
base of his lower neck in the back, below the last row of curlers. By
having the heat trapped inside the hood of the dryer by the shield, the
temperature within the helmet will be several times what a woman endures
for her beauty regimen in a professional salon. But this isn't a woman,
heaven forbid, this is just a sissy. (BTW, if Mistress happens to know a
woman who just might enjoy being an occupant in the SISSIFIER XL 7000,
it is an equal opportunity machine.)

The Sissy, as he is secured, naked, will now see the Application Unit
rolled into position at whatever desired distance the operator desires
for maximum efficiency and desired discomfort of the sissy occupant. It
will be a frightening sight for the sissy to see. And the sissy can not
move. He can not stop anything from being done to him. Oh! The joy of
being a sissy! Even better to be a Mistress.

The Sissy, to warm him up for his coming ordeal, will now have the
vibrating dildo activated by the operator. The motion of the vibration
will enhance the pain from the rubber nodules attacking his miserable
soft sissy butt. This procedure will allow the sissy to cultivate a
sensitive rump to handle any kind of forced or unforced penetration with
the knowledge that significant pain may be involved. While the sissy is
digesting this activity, the operator will apply the suction sheath of
the lower vacuum hose to the miserably limp useless appendage the sissy
has no need for. The operator does have a need. Milking can be fun for
the operator and humiliating and painful for the sissy. Also the milking
will prepare the sissy for the sissy to sissy sucking which is sure to
happen shortly.

The Sissy, while gazing down at what is happening to his weewee, will
now see the operator take one of the chest high appliances and attach
the interior nipple clamp to the right nipple and then turn the dial to
reach optimum pull. The operator may have to adjust the nipple clamps
several times to achieve the best hold on the nipple. The nipple clamp
may even be pulled off in the pulling procedure. This is normal and for
the occupant very painful. Don't worry about it. The operator will then
affix the 5 inch suction cups over the right breast. The procedure will
be repeated for the left breast. Some breast tissue nay have to be
manually situated within the globe of the suction cup for maximum seal
of the cup. And for maximum enlargement and sensitivity. The ceramic
suction cups are designed to use suction energy to pull and attract
fatty tissue which may be collecting near the area of the sissy's
cupcakes. The cups are at times painful but effective. By having the
nipple clamps being pulled at optimum strength and distance, the suction
cups have created space within the mammary gland into which they can
deposit excess fatty tissue. The sissy will not like this procedure. But
it does wonders for his figure.

The Sissy, while moaning at the pain of the nipple clamps and the
vibration of the dildo and the prickliness of the rubber nodules , will
see the operator bring a plastic funnel device (incl. with the SISSIFIER
XL 7000) with a very wide opening on each end, up to the sissy's
lipsticked mouth. The funnel will be inserted in the mouth and the
operator will use a forceps to bring the tongue through the funnel as
far as possible. It might be a good idea to use a heavy forceps and
leave them hanging attached to the tongue for a little while. Just for
fun. The flat rectangular sheath suction appliance will then be secured
over the tongue.

The Sissy, with shadowed eyes wide open, will now feel and see the
operator insert the seemingly innocuous oxygen delivery system into his
nose.

(Think of the other sissies standing next to their own SISSIFIER XL
7000's. What will they be thinking and feeling? And who cares!)

The Sissy will now be allowed to remain secured as calmly as possible in
this situation so that he can come to the realization that, other than
the vibrating dildo, NOTHING else on the horrible machine has yet been
turned on. He can imagine what lies in store for him in the very near
future. Sweat tends to flow copiously at this time.

The Sissy wants to move his feet to relieve the tension. With the seat
protruding from the front of the base, the knees are thrust forward with
the feet being locked back under at the base, with the added pain of the
heel rising four inches above the secured toes. It is possible the
sissy's legs will cramp. it is probable that he will not be able to walk
for a few hours after each session. That would be a good time to have
the wuss lick all your boots sparkling clean.

The Sissy is now terrified.

The Operator, at her leisure, can now commence flipping switches and
turning dials. Please do not rush. Be patient. The sissy isn't going
anywhere. His pain and humiliation are your joy and fun. Savor it. Enjoy
it. Control it. Use it. Tale it slowly. Each new torment allows him to
think that their are still other, worse, torments still to come.

Flip - The dryer roars into action. The temperature setting is very
high. The baking of those steel rollers has started. The occupant knows
that those rollers and the tremendous heat are baking luxurious curls
into his sissy hair. I am sure this is the only thing he has to look
forward to at this time. It is possible that at some point before the
session is over you may notice a slight smell of singed hair. Don't be
upset. It can't hurt you.

Switch - The dildo stops vibrating for the moment but now starts to
begin slow in and out thrusts of the dildo into the virgin pussy. In ten
minutes the vibrating function will also join in. (The dildo does have a
interior delivery system for lubricating gel. The longer he can take it,
the better.)

The dildo control does allow for depth of penetration and frequency of
thrust. Try several settings to define Mistress' best enjoyment.

Flip - The air flow tubes will now deliver a mixed perfume of human
excrement and baby throw up and two day old cigar butt. It is hard to
imagine how any one could toss their cookies while wearing the tongue
sheath and the mouth funnel, but you better be prepared.

Switch Right - The Sissy's right breast will be subjected to pulsating
vacuum sucking actions with the nipple clamp, at full extension, doing
quarter turns on the no vacuum cycle. The circular breasts cups will
cause soreness in the stretching skin of the man boobs. After 15 minutes
slight bleeding may occur at the edges of vacuum cups. But think how
much the sissy will enjoy the cool feel of his silk bra cups later in
the day. When he is done in the SISSIFIER XL 7000, his sensitive breasts
will stand up proud even with the slight touch of frilly silk.

Switch Left - The Sissy can't have one breast larger than the other,
right?

(BTW the nipple clamp quarter turn function does allow for settings
which would allow a full 3/4 turn at random intervals. Just to make it
interesting for the occupant.)

Note: An upgraded version of the SISSIFIER XL 7000 does contain an X-ray
viewing feature which allows the Mistress to see the interior action of
both the hydraulic dildo and of the breast enlarging suction cups.

This feature is very satisfying for the Mistress and worth the extra
cost.

Toggle - The tongue sheath sucks and sucks and sucks on that disgusting
sissy tongue. The sissy will have a much longer tongue to satisfy his
Mistress after a few sessions on the SISSIFIER XL 7000.

Flip - The best for last. The Milker repeatedly does it's function.
Whether the little wee wee can handle a man's job or not, it does not
matter. Milk is what is important. It is what a sissy is made for. And,
obviously, the more milk the sissy produces, the more sissies will be
able to drink it.

By this time a few of the other would-be occupants will have passed out.
Scrap them up off the floor and start getting them ready for their fun.
You have plenty of rollers and lipstick. As it comes time for each one
to be shampooed and rollered, be sure that they pass the occupant on
their way to the hair wash basin. As they pass they occupant they should
be encouraged to place their painted acrylic nailed hands on the
occupant's breast suction cups. They usually scream when they feel the
power emanating from those suckers.

Mistress recommends not more than one half hour for the first session
with the SISSIFIER XL 7000. Or if you don't give a damn, do whatever you
want. They are only Sissies.

Picture the sissy in the SISSIFIER XL 7000.

His lipsticked mouth wrapped around the plastic funnel and his tongue
being sucked out of his head. And he is unable to make a sound.

His breasts being enlarged and sensitized for your pleasure and his
humiliation.

His nose cringing at the vile stink which sissies must be able to
endure.

His feminine shadowed eyes wide open in pain and humiliation. Maybe a
tear trying to ruin his mascara.

His milk running into the crystal collection jug at the base of the
milker.

His vagina being enlarged in width and depth for future use and for his
humiliation.

His feminine butt cheeks, raw and sore, ready to take any type of
pressure his "dating sessions" may provide.

If you had a SISSIFIER XL 7000 you could have the pleasure of seeing
this sight anytime you wanted. That's what Sissies are for and that is
why my Mistress designed the SISSIFIER XL 7000. For your pleasure, your
great pleasure.

I think it is important to mention that any device which is part of the
SISSIFIER XL 7000 can be applied to the sissy singly without the
Mistress having to use her valuable time installing the sissy into all
the devices.

The Mistress may wish the poor sissy fellow to have an intensive bust
enhancement regimen prior to the sissy's fitting for a strapless
cocktail dress, or maybe he needs to be especially provocative in a form
fitting gold lame' evening gown or, possibly, last year he was not quite
into proper curvaceous form in his Lycra spandex one piece bandeau swim
ensemble.

The Mistress may have need of a series of dryer punishments. Or the new
sissy may have to be schooled under the dryer in the proper etiquette
and postures necessary when in the company of genuine women under hair
dryers prior to his first visit to Madame's own neighborhood salon.
Madame can not be embarrassed by a sissy who is afraid of a salon dryer.
Since the sissy will be spending a great deal of time in Beauty Salons,
becoming as beautiful as a sissy can be, he must be totally trained by
use of dryer punishments.

The Mistress may want to utilize the hydraulic dildo to ensure the sissy
has an adequate opening radius in his vagina before the sissy has his
first "date" with a manly man. Though tightness can be beneficial also.
Oh, the decisions!

The Mistress will want to ensure that there is always a large supply of
sissy milk on hand for feeding purposes. That attachment will harvest
large quantities of the sissy's fluids whenever she may desire. Sissies
can not be feed too much Sissy Milk. Picture any sissy you know with a
milk mustache like in the "We got milk" ads in Vogue and Allure.

Mix and match. There are unlimited varieties to the torment and pain and
humiliation you can subject your little sissy boytoy to at any time you
desire.

Mistresses have been known to install the terrified sissy at bedtime
into the SISSIFIER XL 7000 and set the machine for intermittent
servicing all through the night. The sissy in the morning will be
prepared just as you desire and deserve. Something like a crockpot.

Please get your orders in as soon as possible. As more orders pour in we
will find more sissies for testing and quality-control purposes. That
will take a lot of pressure off me.

Thank You,

Sissy Wendy


PS. If you would like to apply for a job as a tester and quality control
person for the SISSIFIER XL 7000, please send me your name and address
and bra size.

PILLOW TALK

By Bea


"What a wonderful day, darling. Things going so well at work - well, at least
for me. I'm sorry yours wasn't so good, but turn around, mummy'll make you feel
better - now, c'mon now. That's it!"
"Don't! Here. Put your arms around my neck, not around my waist - you know.
The way I like it. That's it. Isn't that much better?"
"Soft. Your thighs are so nice and soft. You know, I always thought that my
husband would be , like, you know, muscular..? But I've got more muscles than
you - did you know that your upper arms are almost like a girl's?"
"You know, I can feel the heat from you blushing. Don't you like me saying nice
things to you?"
"Mmm..Mm I like kissing you.."

"Hush, sweets. Don't you remember how upset you were when you couldn't make
love to me on our wedding night? How pleased you were when I took the
initiative and got up on top? How much you liked it?"
"If you keep acting huffy, I'll make you try getting up top again. Is that what
you want? Is that what you really want?"

"See! Told you! Now why don't you get back down, and let mummy get on top
again? There, that's a girl."
"Oh, stop complaining! It was just a figure of speech. That's what I say to
the girls in the office all day - it's just a habit - I didn't mean anything by
it for goodness sake. Here, give mummy a kiss. She's sorry."
"Mmm..Mm."

. . .



"Wasn't that great? My second promotion in less than three months? We can sure
use the money."
"No, no, sweets. Don't feel bad. Yes. I know you've been there much longer
than me - they just don't appreciate men there, that's all. S'matter of fact,
you know Jack .. In the mail room? Just quit. That means you're practically
the only man in the whole place now."

"By the way. That new girl .. What's her name? Yeah, that's right, Joanne.
She's pretty aggressive isn't she? Well, don't be such a snob. I know she's
only an office girl - I just said she's aggressive, that's all."
"No. I wasn't implying anything. Well, let's be honest. Face it, you're not
aggressive. Oh, let's not argue. I like you the way you are. C'mere. Let
mummy give you a big kiss. Make you feel better. Mm..Mm."

"Sorry dinner turned out shitty. Guess I'll never be a cook, but that was a
lovely dessert you made. Saved the meal from being a total disaster. Did you
hear Barb rave about it? - Oh, you gave her the recipe - that was sweet of you.
And it was nice of you and her to do all the dishes, though you did make an
awful mess of your shirt when you splashed up that stuff from the sink. Yeah, I
wasn't too happy with Ellen for laughing at you either."
"But I've got a big day tomorrow. Think I'm gonna get a new group. I'm not
sure yet, but c'mere, cuddle in to mummy. That's a good girl."
"Mmm..Mm."
. . .



"Boy! What a week that's been! How do you like me as a boss? No! I told you
I didn't know I was going to get your group. Won't you admit now, that I had a
good idea in not telling anyone at work we were married? If we'd said anything
about it, you might have been asked to leave the company altogether, and then
where would we have been? Jobs are really tough to get these days."

"Remind me to get a bottle of booze to give to Ellen tomorrow night and - would
you pick up a nice bunch of flowers for Barbara? Don't be silly dear, your
taste in flowers is much better than mine."

. . .



"Boy! That Barbara can cook, can't she? I'm stuffed. Well you can't talk. I
didn't see you passing up much. She seemed pleased at the help you gave her in
the kitchen. To tell the truth, you seemed happy too. The pair of you looked
like sisters in these frilly aprons .. Yes, yes, I remember about the mess you
made of your shirt last week ... Oh c'mon now - she made you wear it? Oh, she
convinced you that it was a good idea. That's better. But what was the chiffon
hair scarves for? Oh, to keep the hair out of the food? That makes sense, I
guess. And wasn't I right about the flowers? She was never that pleased with
any I ever got her."

"Oh. Before I forget. I've a project that needs doing in a hurry tomorrow, so
I'm going to put you and Joanne on it together. What do you mean 'she's hard to
get along with'? Oh, yes she does seem to have a problem taking instruction.
That shouldn't be a problem though sweets. Well.. It's the other way around
actually - you'll be working for her. Oh stop complaining for goodness sake.
She's much more aggressive than you - and I need the job in a hurry. Now don't
turn your back on me!"

"I mean this sweets. You're starting to really bug me. Now come to mummy.
She'll give you big kisses and.."

"Now. I warned you, didn't I? Don't cry. It was just a little spanking, and
you were being very naughty, weren't you? Yes, yes, there's a good girl. Come
to mummy now, and we'll kiss and make up."

. . .



"See! Didn't I tell you? Joanne and you are doing a great job. Well, so what
if she's bossy? I didn't hear you complain this afternoon when she got you to
go and make the coffee for me and her, did I? Didn't she say what a wonderful
help you'd been? Maybe you should take in one of your new aprons to the office?
- Bet that'd impress her all right. Oh, I'm only teasing, for goodness sake!"

"Are we going to argue about this again? For Christ’s' sake, you women are all
alike! Well, I'm sorry. Told you before, it's just a figure of speech. But
honestly. Barbara tells you to wear a pretty apron and a chiffon scarf about
your hair when you're in the kitchen, and it's all big smiles and 'yes
Barbara's.' I buy you some pretty aprons and scarves, and it's 'oh, this is so
embarrassing. I can't wear this - it's too feminine..'

"Yeah. I've noticed how much time you're in the kitchen now. Why else would I
have bought you the aprons? But you're a great little cook. And didn't you
offer to be more of a help? Well, how was I to know you didn't mean forever?
But you really are a pretty good little housewife .. Oh, before you iron my
white pleated blouse this week, would you check the sewing on the buttons at the
back? Some of them might need fixing. Yes? There's a good girl!"

"And I was just thinking. You know, when you do the housework? I've got some
pants that are just a little too small for me - they might fit you.
Yes, of course they are women's pants - you ever seen me in men's? Oh, don't be
so ridiculous! Who's gonna see? I'll look some out for you tomorrow. Now go
to sleep and stop arguing all the time!"

"Yes. I'm kinda mad at you. O.K., I know you don't mean to make me mad, but
sometimes you're just so naughty! O.K., That's fine. Come to mummy then.
That's a good girl... But I'm still a little angry at you, you know.
My mother was Scottish. What was it she used to call Sissies?
Eh?. eh?. Jessies! That's what it was. Jessies! But I don't think much of it
for a name, do you? Well, when you're being naughty, I'm going to tease you.
Gonna call you by a girl's name - got it! Jessica! Isn't that a better name?
Jessica going to say she likes her name? Or would she like to go over mummy's
knee instead?"

"Yes, yes! I won't call you Jessica anywhere else. I promise!"

. . .

"I know I promised. I know for goodness sake! I forgot!
Anyway, I don't see how you can blame me. It wasn't me that was flitting
around being the 'coffee girl' this morning - yes, I've heard how you agreed to
take your turn - but how come it's only you and the office girl
doing it? Oh, Joanne thought it a good idea? Now it makes perfect sense."

"And sitting there at lunch time with Mary, Agnes, and Frances. Diddums like
crocheting with the girls? Diddums like wearing a nice pink satin smock like
the other girls? Oh, so its got big pockets, handy for holding the wool - well,
of course! Why didn't I think of that?"

"So Joanne 'suggested' you interact more with the other girls in the group? So
what? Did you have to join the crocheting circle? What would you do if she
'suggested' that you use the 'ladies room' with the other girls? Bet you'd fit
right in there - especially if you wore your little pink smock. "

"Oh, stop crying Jessica, I'm only teasing you for goodness sake. Give mummy a
kiss. Mm.mmm ... Are you wearing perfume?
Well, I only asked for goodness sake! Oh! I just remembered. How would you
like to crochet me one of these loose fitting 'weskits'. I don't know. Some
sort of angora mix would be nice, maybe in a light blue. You'll do that for
mummy? That's a good girl! Mm..Mmm."

. . .



"Jessica. That was a really nice meal again tonight. I think even Barbara was
impressed. She had seconds on your salad, and Ellen had seconds on that
cassoulet - and the bread, that was out of this world! What are you trying to
do? Get me even fatter?"

"Of course Barbara noticed that you were wearing ladies pants. I mean, what do
you want me to say? That she didn't?"

"But I don't want to talk about food - I'm a little horny tonight. Here, give
me a kiss. Mmm..Mm you are so soft - and you do smell so pretty, you sure you
don't have perfume on? C'mere to mummy."
"No! I won't allow you to get a haircut tomorrow. I like your hair that length
- maybe even a little longer. Well, for goodness sake! Talk to Barbara, or
even Frances in your crochet circle - both of them are great with hair. If you
ask, I'm sure they'll show you how to take care of it.
Now give mummy a kiss. You sure you don't have perfume on? Smells like
Shalimar to me?"

. . .

"Now. Admit it, wasn't that a fun evening? Oh, c'mon. It wasn't my fault that
Ellen didn't want to wait for a pool table and we decided to come back early.
It wasn't me that was prancing around in a dress and heels - well, how was I to
know that you were just giving Barbara a hand by modeling a dress she was
making for a friend? But I still think she was conning you - I mean, I can see
having to have the padding in the bra to get the bust size right, but you had to
wear heels to get the hem right? - And the frilly petticoat was to check the
amount of skirt material? Yeah, sure!"

"Well, I was a little pissed off. Of course I was. I mean, look at all the
shit you raised last month when I got you some aprons - eh? Barbara gives you
some kind of B.S. And, next thing, you're all cute in a dress? So, what if I
got a teeny bit mad and made you wear it for the rest of the night? Admit it,
you enjoyed it, didn't you? I saw you dance with Ellen - all sweet and clinging
- didn't take too long for you to learn the girl's part, did it?"

"I did think you and Barbara looked cute together, trying to figure who should
lead. That was funny. She did a nice job on your hair and your makeup, don't
you think? Well, you had to get back here, didn't you? And you had the choice
of looking more like a girl, or like a boy in a dress. Remember how you pleaded
with me to let Barb put makeup on you? So maybe I don't want you to take it off
right this minute. Yeah, I'll probably let you wash your hair out tomorrow
sometime, then you'll have Sunday to get it back to normal before work on
Monday."

"And now, something's been buggin' me. Tell me. You've been wearing Shalimar
for a couple of weeks now. Now, no bullshit! Who got it for you?
Jesus! Nancy! The new office girl? Oh, she's just fooling around, putting a
little on you. Every day? Aw shit! You seem to do everything anybody else
tells you. Barbara, Joanne, and now Nancy for Christ’s sake! But fight tooth
and nail with me when I ask the simplest things from you."
"Good night!"

"You keep saying 'I'm sorry, I'm sorry.' but it didn't stop you from arguing
with me at Ellen's and Barbara's when I told you to keep the dress on - did you
argue with Barbara when she 'asked' you to put it on? Do you fight with Nancy
when she says "Oh let's put a little perfume on Jessica
- or whatever it is she says. And I'll bet you don't tell Joanne you don't
wanna crochet today, because the pink satin smock you wear is a touch girlish
for you?"

"Yes, of course I want you to wear that dress and petticoat sometime. As a
matter of fact, I paid Barbara for them before we left - you can count that
outfit as one of your birthday presents next week.."

"Well, it's nice to hear that you'll do that for me. Forgive me if I sound
sarcastic but at least that's something - I still don't think it's a whole
helluva lot - after all, Barbara was the one that got you into it originally.
Wearing it just for me is no big surprise now. No. I don't know what I want!"

"You will? You'll wear another dress for me? No arguing? You promise?
Huh? How come I don't believe you? Suppose, just suppose, I asked you to go
out to dinner with me, and bought you a red satin dress to wear? Stop futzing
about now! You would?
Ok. I can ask you to wear a dress, anywhere, any time - yes, I know, just once
- but that's a promise?"

"Ok I forgive you. Come to mummy. There, that's a good girl."

. . .



Well, wasn't that a nice surprise - the girls having that little birthday party
for you at work today - and the nice presents you got. What were they again?
Panties?, Stockings?, Lipstick, and a new smock for your crocheting stuff. I'm
surprised that they got you a blue one - you know, the 'masculine' connotations
- but it's a pretty blue, don't you agree? And these big pearl buttons at the
neck and cuffs - don't think anyone could possibly get the idea that it'd be for
a man, do you?"

"Oh Jessica! I damn near died trying to keep a straight face. You should have
seen your expressions, as you opened up your presents. There, circled by
giggling girls, having to say "Thank you" to them all - and modeling your new
smock - oh it was priceless! I notice that they all call you Jessica now.
Didn't you tell them that you objected to it? Oh. I thought you did. - Not
that they'd pay much attention anyway."

"Gonna wear your panties to work tomorrow? Don't be silly, of course you
should. I mean, how d'you think one of your friends are gonna feel when they
ask 'you wearing your panties today Jessica? The ones you liked so much
yesterday?" - and you tell them 'no!'

"Yes. It would be easy to say 'yes' and be telling a lie - but I'd bet that
there's gonna be more than one finger snapping your panty elastic from outside
your pants - lots of girls do it to each other, just for fun. And you might
just piss off some of these tougher girls - you know, telling them how much you
liked their presents one day, then lying to them about wearing them the next.
Might get real mad at you then, huh?"

"And aren't you glad they don't know we're married? I mean, what would you say
when they asked you "what did your wife get you for your birthday?" You gonna
tell them about the dress - and the frilly petticoat - and the two pairs of
lovely baby doll pajamas - which ones you wearing just now? I can't see too well
in the dark. Oh yes, the pink ones - go better with your new lipstick, right?"

"Well, let's see. Got nice baby dolls on, a little touch of perfume, a trace of
lipstick. You're nice and soft, as usual, and you've even put your hair up for
mummy - though she did have to ask - just a nice pretty little girl on her
birthday. Now come over mummy's knees and she'll give you your birthday spanks
- there, that's a good girl."

. . .


"I've got to say this Jessica. You really are getting kinda girlish you know?
I mean, even at work. You've only been wearing panties for what?, A couple of
weeks at most? But your hair is almost like a girls. You wear lipstick most of
the time now - didn't I see you freshen it up at your desk this morning? Yes.
Thought so. You're starting to walk like a girl, talk like a girl...

"But what's bothering me is that I think Joanne's about ready to make a play for
you. Yes, I know she's a lesbian - but you are getting cuter and cuter all the
time - and I don't mean 'macho cute' either. I'm starting to think that I'd
better let the people know what our relationship is."

"Yeah, I know I've been against it - but there's something come up. I don't
know how to tell you, but Kathleen's leaving - and they've offered me the whole
department - yeah! I'm scared that Joanne - she's going to be your new manager
- now don't fuss. I spanked you the last time, and I'll do it again. - Anyway,
I'm scared that with me gone, she's going to take you over."
"No. I can't promote you. Surely you see that?"

"Well, I've decided to take you up on the promise you made me some time back.
Remember? The one about wearing a dress for me? Yeah, thought you would.
Well, the company costume ball is next week, and I can't dodge it now, now I'm
at the level I'm at - so you can wear it for me then."

"Oh stop it. I know you're not complaining - and lucky for you, you're not. I
have an idea for your dress, but I've got to do some checking. Now go to sleep.
Mummy's tired."
"Yes. Thank you dear. I knew you'd be happy to hear about my promotion.
Night night."
. . .



"No. Don't get undressed yet. Come over here. Sit by me on the bed. Here,
let me arrange your veil for you. Mmm.Mm you make such a lovely bride. All
that white satin really suits you. I must say, Barbara did a fantastic job on
taking my wedding dress in for you, don't you think?"
And didn't she look so nice in her bridesmaid's dress? The two of you made such
a pretty picture - but you definitely were the belle of the ball. Boy, I
couldn't believe how jealous some of these other girls were when they saw you.

No. C'mon! They weren't being mean to have that little ceremony for us, after
I told them of our intention to get married - they were just being nice - didn't
lots of them dance you afterwards? They wouldn't have done that if they didn't
like you - would they? Well, of course some of them wanted to tease you a
little - I mean, it's not every day you see such a pretty male bride, especially
when he dances the girl's part so well.

What does it matter what they say on Monday morning? Just wear your new dress
in to work - of course I'm serious! You're surely not going to pretend that
you're a man any more, are you?

Now just lie back here in mummy's arms, and we'll play husband and wife.
But we'll do it the right way this time, OK? Just LOOK at this new toy that
Mummy has for you! Want to give it a kiss?

Sissy Mission 7

Lawnmower
By Cheryl Alison

It was a Sunday evening and Mistress and I were lazing
around watching TV trying to avoid the reality of work on
Monday morning. The Simpsons was on, and Homer and Flanders
had made a little bet. Somehow, they both lost and had to
mow their respective lawns wearing their wives' Sunday
dresses. I looked at Mistress and I knew that another Sissy
Mission was probably in my future!

"Hmmm," was all she said. I knew I was in for it.

Monday afternoon I arrived home from work to find Mistress
in the kitchen smiling and humming away as she put away the
groceries she had picked up on her way home. She smiled at
me as I walked in and placed a perky little peck on my
cheek.

"Go see what I have laid out for you."

I went to our bedroom to get out of my work clothes and
found that I would not be getting dressed in my usual
sweats for an evening at home. On the bed was a dress I had
not seen my wife wear for some time. It was a throwback to
the 80s — a pastel floral print with a light crinoline
underneath and lace around the edges. She had also placed a
gold chain on the bed, with the key to the lawn tractor
attached.

Mistress entered the room and said, "Put it on, sissy. The
lawn needs to be mowed and you're just the sissy to do it."

I sighed but dutifully stripped off my work clothes and
placed the dress over my head. I looked a little ridiculous
with a five o'clock shadow and no makeup or the usual
complicated feminine preparations that Mistress requires
for a Sissy Mission.

Mistress walked over and gently buttoned up the back of the
dress. She took both of my hands in hers and stepped back a
little, admiring her sissy in his Sunday dress.

"Oh, one more thing," she giggled. "Here's your panties.
Step in, sissy." She produced a pair of red velvet panties
and I stepped into them. She snugged them up and gave me a
little thrill as her hand passed over the front.

"Now march out to the garage and fire up the tractor,
Sissy," she said, playfully slapping my bottom.

It was summer and of course at 6:00 pm there was still
plenty of bright sunshine to reveal me in my Sunday dress
mowing the lawn. Several cars slowed down and gawked, with
the occupants laughing and pointing. Mistress had come out
while I was mowing to tell me that it would be a good idea
for me to wave to passing cars, so that added to my
humiliation.

By 7:00, I was done and putting the lawn tractor in the
garage. At least half the neighborhood had seen me, and I
was sure the phone lines were abuzz. Mistress intercepted
me in the driveway as I was planning to enter the house to
remove my dress. There was a glint in her eye and a hose
nozzle in her hand.

"Stop right there, sissy," she said authoritatively.

I looked at her with a "You wouldn't" look and suddenly I
was the recipient of a shower of cold water. Mistress hosed
me for a good five minutes, which was long enough for our
friends Bob and Marianne to pull up in the driveway. They
were generally clueless about our Mistress/Sissy
relationship, but they were aware that we were not quite a
conventional couple, either.

"How do you like my husband in his dress?" said Mistress.

Marianne giggled. "He looks like he had a shower." Then her
eyes fell to my midsection, where the material of the dress
was almost sheer in its wetness. "Ohh!" she squealed in
delight. "Nice red panties!"

Bob was laughing. I was in awe. I wondered if Mistress
hadn't picked up the phone and invited them over.

Bob said, "Boy, I bet you'll never bet on football with
your wife again!" If only he knew that there was never a
bet!

"Well, it wouldn't be the first time he's worn panties,"
said Mistress loudly. Bob and Marianne just laughed,
thinking it was a joke, and I nervously chuckled, hoping
that she wouldn't reveal much more.

Mistress invited Bob and Marianne in, and as they entered
the house, she whispered in my ear, "Sissy Mission
accomplished... for now."

I found some dry sweats and joined Mistress, Bob, and
Marianne in the family room. As I entered, Mistress told
me, "You know, I just volunteered you for a service
project. Marianne is the Relay for Life coordinator and
they're having a womanless beauty pageant. I told her
you've been practicing in high heels for just such an
occasion. She's looking forward to making you fabulous."

Sissy missions are never done.

Sissy Mission 6

Poodle Skirt
By Cheryl Alison

I sat on the bench assessing my surroundings. It was

a well-kept small town, with a cobblestone main

street and nicely maintained historic buildings.

Banners and awnings in the front of shops fluttered

in the breeze, advertising everything from antiques

to hardware. Since it was a town located on a large

lake with lots of recreation opportunities, it was

busy on this early June day. People strolled up and

down the sidewalks, ice cream cones in hand, most of

them escaping from stressful jobs in the city or

feeling the freedom of being out of school for the

summer.



The breeze tugged at my skirt, and instinctively I

moved my left hand to the hem. I looked down at the

skirt, reminded of how out of place I was here.

Rather than a light cotton or rayon summer skirt, I

was wearing a heavy pink poodle skirt right out of

the 1950s. I was also wearing black and white saddle

shoes with white bobby socks, and a pink sweater. My

hair was done in what my beautician had called a

"pixie cut" and my nails were painted pink to match

the outfit. Pink blush, lipstick, and eye shadow also

complimented my ensemble, while a pair of vintage

cat-eye sunglasses provided the finishing touch.



In short, I was an anachronism. Most of the people

around me were dressed in L.L. Bean casual, while I

was a pink 1950s girl surrounded by the millennium.

Only the town, perfectly restored in its brick

facades, was a fitting surrounding for me. People

were beginning to take notice the moment I sat on the

bench, and passers-by were very interested in what I

was doing. The first group of strollers was three

older women, who had probably grown up in the 1950s.

They stopped, lining up to scrutinize my outfit.



"Well, honey, that is a cute outfit!" bubbled the

more outgoing of the three. "Why, I haven’t seen a

poodle skirt since high school. Where did you get

it?"



I gathered up some courage and spoke. "My mistress

gave it to me. I am being punished for being a bad

little girl."



My voice spilled the beans. In makeup and shades, it

was not obvious to the general public that I was a

man. However, when I spoke in my usual deep voice,

the ladies could hardly avoid the truth.



"Oh!" yelped the woman. One of her friends covered

her mouth and then sort of giggled nervously. "Well,

we have to be going, girls," she finally said and led

her friends down the street, bewildered.



In the meantime, more and more people seemed to be

taking notice of me in my unique situation. Many

probably thought I was part of some sort of store

promotion, so it seemed that folks on the other side

of the street were gravitating toward my side of the

street.



A couple of girls in their teens stopped by in shorts

and crop tops, complete with lip-gloss and sun-

bleached hair. "Are you giving away coupons?" one of

them asked.



"No, I’m here to be punished."



Once again my voice gave me away. The girls began

giggling uncontrollably, but instead of moving on as

the older women had, they stayed.



"Punished for what? You’re a man." The two statements

didn’t really seem to fit together, but marked their

confusion pretty well.



"I’ve been a bad girl."



"Oh, I see," smiled the taller of the two. "Well,

you’re very pretty. Do you have a boyfriend?" she

said, smirking.



"Err, no." I said, turning beet red and hoping they

would leave.



"Do you have panties on under that skirt?" piped up

the other of the two.



"Yes, they are pink," I answered, with the statement

that Mistress had told me to use if anyone asked.



"Do you like to wear dresses and stuff? Are your

boobs real?"



I squirmed on the bench, wishing they would leave.

"Yes, I like to wear girlie clothes. My breasts are

forms that I stuff into my bra."



"Are you a crossdresser?"



"Yes, my mistress doesn’t allow me to wear any men’s

clothes anymore outside of work."



"Well, we think you’re cute. Bye."



Finally! It was about time to end that humiliation. I

looked at my watch. I had only been on the bench for

fifteen minutes! It had felt like the proverbial

eternity. I had three hours to go.



"Mommy, look at that lady!"



"Nice skirt!"



And it went on and on. Every time I interacted with

someone, his or her eyes got big in shock as I

revealed my maleness with my voice. Then it would

turn into a long explanation about how I was being

punished.



It wasn’t until someone offered me an ice cream cone,

though, that anyone noticed another aspect of my

predicament.



"I’ve seen you over here for about an hour, and I was

wondering if you would like an ice cream cone," said

the woman in her thirties.



"Yes, I’d like that," I said, reaching out with my

left hand. I didn’t catch her reaction at my voice,

but as I was taking the ice cream cone from her hand,

I dropped it on my skirt. My urge was to bring my

right hand forward to grab it, but I lurched against

the bench. You see, my right hand was handcuffed to

the bench.



"Oh, dear. Let me help you," she said graciously,

pulling out some napkins and helping to wipe off the

mess."



"Thank you," I said.



"Poor dear, why are you handcuffed to the bench?"



"I’ve been a bad girl and I’m being punished."



She erupted into laughter. "What are you being

punished for? It’s kind of unusual to be punished by

dressing in a poodle skirt and being handcuffed to a

bench."



"My wife caught me with her pantyhose."



"Oh, you’re a crossdresser! How interesting!" she

said, just a little too loudly, drawing the attention

of the seven or eight people adjacent to our area. A

few threw disgusted looks our way, and others sort of

milled around, mumbling to each other. I could hear

the occasional "weirdo" and "freak" come out of those

conversations.



"How long do you have to sit here?" she asked.



"Until 6 o’clock," I answered.



Her eyes actually flashed something like sympathy.

She sat down on the bench next to me, putting her

hand on my knee. "Well, I’ll sit here for a minute

with you."



I was glad to have found someone to talk to, hoping

it would pass the time. She seemed very sympathetic,

and it was almost a turn-on to have a woman

interested in my state, rather than repulsed by it.



"You don’t recognize me, do you?" she said.



"No," I said, expecting her to relate to me that she

was some kind of local celebrity.



"I’m Nancy’s friend Julie from work. She asked me to

come by and see you."



My wife’s friend! I had met her and her husband at a

holiday party we had held at our house. Now I

recognized her. The sense of humiliation took another

turn, deepening and forcing me to realize that

Mistress never leaves anything uncomplicated.



"You look really good. I’m surprised. I thought you

would look like a guy in drag, but you look like a

fifties girl, just maybe a little bit on the tall

side," she complimented.



Well, maybe it wouldn’t be so bad after all. Perhaps

Mistress had just sent Julie to check on me. She was

certainly being sympathetic.



"Nancy did ask me a favor, though. You see that

female police officer down the street? I’m supposed

to ask her for a handcuff key. Then you’re to come

with me."



Crap--here come the complications, I thought.

Mistress is never happy just humiliating me in a

simple fashion.



Julie motioned the police officer over. "Ma’am, I

think this poor girl here has been the victim of a

trick. Can you unlock her?" I kept my face down,

hoping that she wouldn’t notice that I was a man.



"Sure," said the lady cop. "How did you get in this

situation?" She had done what I dreaded most—asked me

a direct question.



"I was a bad girl and I’m being punished."



"Oooh!" she said, taking some delight in my

predicament. "Perhaps this is a punishment I can

suggest to our local judge!" she joked. "You’re

cute."



I didn’t feel so cute; as a matter of fact, I was

beginning to feel a little sick, knowing that Julie

had been sent by Mistress to take me to entirely

another level of humiliation.



After the cop left, Julie said, "Come on, I’m

supposed to take you for a drink."



That didn’t sound too bad—Mistress had taken me to

the House of Pancakes in drag before. I figured I

could handle a half hour in a bar.



Julie took my hand and led me down the street to

where a sign said "Big John’s Pub— Happy Hour 5:00."

It was noisy inside and filled with patrons. As we

entered the doors, though, my heart just about

stopped. On a stage across the bar was Mistress,

dressed in her favorite black leather mini and a

sleeveless shirt, perfectly made up and wicked.



"Happy hour has begun," she yelled into the mike,

amid cheers from the patrons. "Today’s happy hour is

special. We have a drink promotion for the ladies.

Its called Spank the Transvestite! If you swat this

little girly man’s bottom, you get a free drink!"



The crowd loved it, anything for a free drink, and to

watch the humiliation of another human being to boot.

What a deal! Many of the women in the bar rushed

forward to participate.



Mistress came down from the stage and took my hand,

leading me up to a chair. I expected her to tell me

to lean over it, but instead, in the final crowning

humiliation, she sat down, and pulled me over her

knee. She whispered in my ear, "I want to hold you

and watch your bottom get red."



In a flourish for the crowd, she raised my pink

skirt, revealing my skimpy pink ruffled panties for

all the bar patrons. A cheer rose up, and someone

started chanting, "Spank! Spank! Spank! . . ."



As each woman came up, they had a tray of beers ready

to hand out. The first woman raised her hand and

joked "This is going to hurt me more than it will

you!" and laid into me with a good SMACK! Although

most showed some restraint in their spanking, the

fire in my bottom grew as the night went along.

Periodically, Mistress Nancy would make me stand up

and twirl me around, showing off my red bottom.



As a finale to the evening, Mistress got very

creative. "Our little sissy has been so good tonight,

let’s cool down her bottom!" The crowd cheered as she

made me bend down, placing my hands on the floor with

my bottom high in the air. "Bottoms up!" she yelled

as she splashed her drink across my pink panties. It

ran down, soaking parts of my skirt and sweater.

Patron after patron ran up to the stage, splashing

their drinks on my ass until I collapsed on the

stage, soaked in everything from beer to rum.



Mistress grabbed my hair and pulled me up. With a

glint in her eyes and a sly smile, she leaned toward

me, placing her hands on my face tenderly. "My little

sissy. Mission accomplished?"



"Yes, Mistress," I managed to squeak out.



And with that, she gave me the unusual reward of

placing her wine-red lips on my pink lips, and

kissing me long and hard, her tongue darting around

mine. "Let’s go home and get a shower, Sissy."

Sissy Mission 5

Stacked Sissy
By Cheryl Alison

Everyone in the hardware store was staring at me. The
checkout lady at the front of the store stared when I
walked in. The mother and her teenage daughter stared. The
guy in the back at the engine shop stared as I walked by.

As I approached the section where they had gas grills set
up for display, a woman who was forty-something with
striking grey hair coiffed in a bob approached me. "Can I
help you, ahh... uh..." She kind of trailed off at the
point where normally one would say ma'am or sir.

You see, I had large breasts. And although the potential
for large breasts exists in humans and there are many
examples, there are few examples on men. Mistress had
charged me (her sissy husband) with my latest mission: to
buy a gas grill while endowed with large breasts. I was
wearing jean shorts with my legs shaved, tennis shoes, and
a white T-shirt. My breasts were courtesy of Mistress:
expensive forms that were applied to the chest with
adhesive. Their realism was stunning, down to the detail of
the nipples. Sometimes when Mistress transforms me into her
sissy, I am nearly passable. This time, I was not. I had to
suffer the embarrassment of large breasts, braless under a
t-shirt, while the only other vestiges of femininity were
my shaved legs and a light pink lipstick. Otherwise,
Mistress had made me keep a small amount of stubble and my
hair styled in masculine fashion. I was obviously a
sissified male with large breasts.

My hardware store helper was standing, a tad stunned,
waiting for me to take the next step in communication. "I'm
here to buy a gas grill." She looked relieved, and took the
opportunity to focus on the request, rather than the
breasts, although her eyes would always seem to end up on
my chest if she looked at me.

"Well, we have several models. Will you be cooking for a
lot of people?"

"Yes, we entertain from time to time. We cook a lot of
breasts. How much is the red one on the end?"

Her reply was less than immediate, due to my comment about
breasts, I'm sure. It was a line Mistress had encouraged me
to use. However, she overcame her shock at my deadpan
comment and replied, "That one is two seventy nine. It's
been a good model for us. We haven't heard of any problems
with them yet. Would you like me to get Dan to load it for
you?"

"Yes, I think that's the one I will go with," I replied.
She yelled at Dan to bring one up to the front while I
moved with her to the checkout.

She rang up the sale, I paid, and then we waited in an
uncomfortable silence for Dan to bring the grill. I could
tell she wanted to ask about my unique endowment, but
couldn't quite bring herself to do it.

Dan finally brought the grill up, and stumbled mightily as
his eyes drifted over my chest. Once he picked himself back
up, he mumbled something about where my car was and I told
him. I said goodbye to the still-confused sales lady and
led Dan to the car. I opened the hatch and he struggled to
place the box inside. It became caught on the lip of the
hatchback, so I moved behind him to help pull the corner of
the box past. As I did, my large breasts brushed his back
and he jumped. Already nervous about just what or who I
was, I'm sure it was a traumatic experience and his
expression was priceless as he turned around.

"Sorry, these get in the way sometimes," I said, holding
them up from underneath, one in each hand. He didn't say a
word and walked back into the store, shaking his head.

Upon returning home with the grill, Mistress asked the
usual question: "Sissy mission accomplished?"

"Yes, ma'am," I said, and related the story to her.

"Good sissy. Now put on your pink satin toolbelt and put
that grill together. The girls are coming over in a few
hours and you're the entertainment. You get to be a one-
sissy wet T-shirt contest."

Mistress never leaves a mission uncomplicated.

Later that evening, I writhed in humiliation as my wife and
her two best friends turned the hose on me as my breasts
flopped around, showing through my white t-shirt. All I
could do is circle the clothesline pole in a bizarre
imitation of a maypole dance, since my arms were tied
behind me around the pole. As a reward for putting up with
a higher-than-average level of humiliation, however, each
woman removed her panties and used them to rub me dry; a
sensual experience that I thought would end the evening.

Then I saw the proverbial glint in Mistress's eye. With her
crooked, cruel little grin, which I cannot resist, she
said, "Missy looks thirsty. Let's give her a drink."

Holding my chin in her strong fingers, she tipped my head
back and wrung out her panties into my mouth. As she held
my head, her friends joined in, giggling.

Sissy mission accomplished? At least for the evening.

"You know, a beer garden with a serving wench might be fun
for Superbowl Sunday," piped up one of the gals.

"Good idea," said Mistress. I fell on the ground with the
last pair of panties stuffed in my mouth, mumbling
incoherently. "I think Missy likes it, too."

Sissy Mission 4

By Cheryl Alison

Mistress believes in community service. So when she dropped
the ad on my desk at home, I knew that I would be a
faithful community servant within a short while. The ad
read:

Southern Belles Needed

The Ladies' Auxiliary needs volunteers to greet
visitors at the Civil War memorial. Ladies need their
own costumes and parasols. Please meet in costume at
the Civil War memorial park on Friday, March 23 at
4:00 pm.

"You're going to look sweet in a southern belle dress. We
better make a hair appointment for Friday. You need to take
the afternoon off."

On Wednesday afternoon, Mistress took me to the costume
shop. She marched me right in and told the owner "My sissy
little husband here needs a southern belle gown. He's going
to a masquerade."

The owner was an attractive woman in her forties with long,
curly red hair tied back in a ponytail. I am sure she had
found costumes for other men in drag, but her smile told me
she could see right through me - that I was enjoying this.

"Well, what is your sissy's name?"

"You can call her Missy," said Mistress.

"All right, Missy, please come this way. I think I can find
you a sweet southern belle ensemble."

We arrived in front of a rack of dresses that were all
elaborate, full-skirted creations of femininity. Looking at
me, the owner of the shop said, "Let me guess, a 16?"

Mistress gave me a look that told me I better answer. "Yes,
ma'am." I replied softly.

"Well, don't be shy, Sissy Missy. I've got plenty of
dresses in 16 for bigger gals like you."

With that, the shop owner ran her hand down the rack and
plucked out two gowns, hanging them in front of us. "Which
one do you like best?" Once again, her question was
directed at me and Mistress gave me another look.

One gown was pink cotton, with lace edging around all the
ruffled layers. Its skirt was voluminous, and the top had
long sleeves and a scooped neck outlined in lace. The other
gown was black with a lighter colored print, and satin
edges on all of the ruffles.

"The pink one, I guess," I answered.

"I might have known you were a sissy with good taste," said
the owner. "Let's help you into it." My pleading eyes
flickered over to Mistress, but I could see that she was
going to let me deal with this situation on my own. I
followed the owner to the dressing room. "First," she said,
"you will need the hoop skirt. Let me go find one while you
undress." I began to remove my pants and shirt, revealing
the bra and pantyhose that Mistress had made me wear for
the occasion. The owner returned outside the curtain, and
said, "Here, put this hoop skirt on and then come out here
to put the dress on. There's no one in the store right
now."

I took the extremely ballooned hoop skirt and stepped into
the middle of it, bringing it up around me. Tying the
waist, I stepped out of the dressing room.

"Oh, my, I see you have a strapless brassiere on. That's
good. I was wondering how you would hold the top of the
dress up with no chest. Come here, and let me see how this
hoop skirt works." She pulled up the hoopskirt, adjusting
it. "I see you have your hose on, too, darlin'. Why you are
prepared."

Pulling the dress on, I was shrouded in soft cotton and
lace edging. The dress fit well and Mistress was pleased.
The shop owner said, "Why I suppose you're going to need a
wig. We've got some Scarlett O'Hara wigs around here
somewhere."

Mistress told her, "Oh, Missy gets her own hair done at the
salon. We'll take her there."

"You are quite the little gal now, aren't you!" said the
shop owner as if she was talking to a ten year old girl.
"Well, you're all set; it'll be seventy five for the rental
through Sunday."

Before I could return to the dressing room to take the
dress off, two teenage girls came in the store. The
giggling commenced as they noticed it was not a woman in
the pink southern belle gown. Mistress was relentless and
instead of guiding me to the dressing room, told them:
"Girls, can I get your opinion on my husband here? How does
he look in his gown? Is it sissy enough?"

They just kept giggling. "Oh, he's cute," one of them said.
"What's the occasion?"

"Oh, he likes to dress up in prissy clothes. He doesn't
really need an occasion, but he's going to volunteer to
greet visitors at the Civil War memorial. He'll be there
this Saturday. Tell your friends."

"That's funny," said one of the girls. "We're here to pick
up gowns for that, too. We decided to volunteer."

"Well, that's great. His name is Missy and I'm sure he's
glad to have met some new friends."

Mistress guided me back to the dressing room, my face
burning in humiliation. I could hear the girls giggling and
talking as the shop owner began to help them find gowns.

On Friday, I got off work early to begin the transformation
to a southern belle. Mistress took me to the salon where
she had made an appointment. First, my longer-than-normal
hair was curled into sausage curls by a young beautician
who kept just gushing about my predicament.

"Oh, I've never done this to a man before. This is fun. You
make quite an attractive lady. Do you want ribbons in your
hair?" Of course, Mistress liked the ribbon idea, so pink
satin ribbons were tied in my sausage curls.

Then, I was moved to another station to get extremely heavy
makeup. "Make it theatrical," Mistress told the
cosmetologist. "I want Missy to stand out in a crowd."

My lips were painted a dark pink, and pink eye shadow and
blush were applied heavily over my pale pancake makeup.
Finally, my eyelashes were given what seemed like seventeen
coats of mascara.

Back at home, Mistress helped me into my clothes. I was
dressed in undergarments that I'm sure were much more
appropriate to the modern era-a longline bra with breast
forms, pink panties (Mistress said they matched the dress)
and white shimmer pantyhose. A pair of high heel sandals
with an open back in white were the final touch to the
ensemble. With the dress and hoop skirt on, I felt
extremely cumbersome and Mistress had to show me how to
hike up and gather the hoops to get in the car. Still, I
couldn't sit down very well.

At the park, there was quite a crowd as it was summer and
tourist season. Most folks on the way in didn't pay much
attention to me. I came to area where the volunteers were
signing up. The woman in charge didn't notice I was a man
until my voice gave me away.

"Well, I guess you look like a southern belle," was about
all she said, sort of rolling her eyes. "I think you have a
couple of girls waiting that wanted to be in your group.
We're walking the grounds in groups of three. A proper
civil war era lady would never have walked alone."

With that, the two high school girls appeared from behind,
recognizing my pink dress. "We thought we would wait for
you. You look gorgeous!" one of them gushed. I looked
behind me to see where Mistress was, and she was gone. "Oh,
don't worry," said the other girl. "Your wife told us to
take care of you. She has some errands to run, so we agreed
to take you home after the fashion show."

"Fashion show?" I questioned.

"Yes, didn't you know? There's a fashion show for all the
volunteers at 5:00. We're going to show off our gowns to
the visitors."

And with that, my southern belle career and my runway model
career began.

When Mistress finally picked me up (late, I might add) her
words to me were "Sissy Mission Accomplished?"

"Yes," I said.

"Good, then it's time to show you off to mom and the ladies
at her card club. You can serve them evening tea on the
lawn. I've already arranged it."

Community service never ends.

Sissy Mission 3

By Cheryl Alison

I stepped out of the car and walked up the driveway of a beautiful suburban
home, the green grass manicured carefully. The driveway was full of
middle-aged women picking through the cast-off items of a rather well-to-do
family. I walked up to the rack of clothing, picking through it. One of
the women sitting at the card table on the edge of the driveway got up and
came over. She was probably around 45, still rather attractive with a
carefully coiffed perm in her dyed blond hair.

As I was lifting the hanger of one of the garments off the rack, she said,
"Are you looking for anything specific, sir? The men's clothes are back
there in the rear of the garage."

"No, ma'am," I said. "I think I found what I'm looking for. I've been
trying to find a bridal gown."

"It is nearly perfect. My daughter wore it for her wedding and decided to
sell it rather than having it heirloomed. Are you going to surprise your
fiancé?"

"No, it's for me. What size is it?"

"For you? Well, that's certainly unusual," she said, a little flustered.
"It's a size 16."

"Do you think it would fit me?" I asked.

"I don't know. You're a man. Can I ask why you might want to buy a wedding
dress?"

"I just like to feel pretty, that's all. I have a collection of wedding
gowns."

"Er, well, I guess it doesn't matter to me. I can't guarantee it'll fit,
though. Do you have cash? I don't really want to take a check."

"Yes, I have the cash right here. But I'm not sure I want to buy it if it
doesn't fit."

By this time, most of the women at the rummage sale had tuned in to what was
going on. The rummage sale lady was getting slightly concerned.

"Well, I suppose you could try it on. But I want to be relatively sure
you're going to buy it."

I handed her the $200 listed on the price tag for the garment. Now she
couldn't argue much with me.

"There's a bathroom right there through the door in the side of the garage.
Take it in there... and please try to hurry."

"Okay," I said, going into the bathroom with the garment bag.

I hurriedly stripped off my jeans and T-shirt, revealing the lace-patterned
pantyhose I was wearing underneath. I slid the petticoat over my head and
it floated down around me, kissing the edges of my thighs. Then came the
bridal gown. I hadn't even taken a good look at it outside. Pulling it from
the garment bag, I found a beautiful gown with a stretch lace bodice and a
huge amount of tulle in the skirt. I carefully slid it on over the
petticoat. It fit with just a little bit of extra room in the waist. The
stretch lace bodice hugged my upper body.

Carrying my other clothes, I stepped out of the bathroom and went through
the door to the garage. When I came out, one older woman sort of gasped in
a half-surprise, half-laughing manner. All of the women at the sale looked
at me. The woman running the sale rolled her eyes.

"It fits perfectly! Thank you so much! I'm going to be a beautiful bride.
Do you think these pantyhose match the gown?"

"You look very pretty," complimented a very old woman from across a table of
children's toys. I think she was blind.

With that, I walked down the driveway and back to the car. I opened the
door and found Mistress smiling broadly. "So, how did it go?"

Mistress always wants to know how it went.

Sissy mission accomplished.

Sissy Mission 2

By Cheryl Alison

I entered the dancewear shop, nervous, and a little hesitant. There were
several women browsing the racks of leotards and dance dresses, presumably
shopping for their little girls. I walked up to the counter.

The saleswoman, whose name tag identified her as Rachel, was very fit and in
her mid thirties. She had her straight dark hair pulled back. "May I help
you," she said.

"Ah, yes. I need to buy a tutu."

"Is your daughter with a specific dance company? I have the list to tell me
which one she needs," she explained.

"Well, you see, the tutu isn't for my daughter. It's for me."

Her jaw dropped just a little bit. "Well, I don't understand," she said,
"what are you looking for? Are you in a comedy production?"

"No, I just like to wear tutus," I said.

She took a breath, and then said, "Well, do you want a romantic or a
classical tutu?"

"I don't know," I said, "What's the difference?"

"The romantic is like the long skirts worn in Giselle. The classical is the
straighter, shorter style worn by ballerinas in productions like Swan Lake."

"Like the ones in Swan Lake, I guess," I said.

"Okay," she said, "I have one or two in stock that may fit you. They are
size adult large." She brought out the tutus, one pink and one white. "Do
you have a preference in color?"

"Which one do you think will match my tights?" I asked her, pulling up my
pant leg to reveal the shiny pink Capezio tights I was wearing.

Raising an eyebrow, she said, "Pink it is." In a very business-like manner,
she took the pink tutu off the hanger and brought it over to the counter to
ring it up.

"How do I know it's going to fit?" I asked.

"Believe me, I think this one will fit you."

"I don't know... the leotard part looks like it might be a bit small."

"It will stretch," she said.

"I don't know, I think I should try it on," I said.

Severely raising an eyebrow and frowning, she said, "Fine, take this and go
in the dressing room back here. Please don't damage the garment."

I took the tutu and went into the dressing room. I slid off my shirt and
pants to reveal my shiny pink tights. I slid the leotard part of the tutu
over my body. She was right-it fit. The stiff tulle tutu just about filled
up the small space of the dressing room. The velvet of the leotard tickled
my skin.

I walked out of the dressing room, in pink tutu and tights. One of the
women shopping took notice, and nudged another one. Rachel looked up from
the counter, frowning.

"You were right, it fits fine," I told her. "Do I look pretty?"

She just shook her head. The other women in the store laughed.

"I think I'll wear it out of the store," I said, moving back to the dressing
room to get my other clothes and wallet. By now, I had the whole store for
an audience.

Once I had paid for the tutu, I left the dancewear store and walked out onto
the sidewalk. I saw several people pointing and snickering as I made my way
to the car in the parking lot.

"Well, how did it go? Did you show her your tights?" she asked. Mistress
always wants to know how it went!

Sissy Mission accomplished... almost.

Mistress was in a good mood today. "Next stop, IHOP. They should have
their lunch buffet about now..."

Sissy Mission 1

Balloon Sissy
By Cheryl Alison

As I entered the suite of offices, I looked for the directory. It was there
on the wall, just like every other corporate accounting office. I scanned
the names. There... Bruce Jones, Managing Director. He would do.

I approached the reception area, and a dark-haired receptionist in a
conservative grey suit looked up. Her standard receptionist smile gave way
to giggles. You see, I was dressed as a hooker and delivering balloons.
The reason that the receptionist could not stop giggling, however, was that
I was a man. I was wearing a short black velvet miniskirt, a shiny silver
blouse, a dark red wig, tons of makeup, fishnet hose, and black patent
leather high heels.

"Can I help you, er, ma'am?" she giggled.

"Yes, I'm here with a singing telegram for Bruce Jones."

"Oh, he's in a meeting, but, oh, I bet I can work you in. Follow me."

She led me into a conference room where a conservatively dressed older man
was leading a meeting.

"Yes, Suzanne, what is it?" he asked.

"There's someone here to see you sir," she giggled, stepping away from the
door to reveal me.

I went into my rehearsed spiel. In my best throaty, sultry, feminine voice,
I said "Sir, you're very special to someone. These balloons are in
appreciation for all your hard work." I then put my arm around him and
said, "You are a very fit man. Do you work out?" He was so flustered he
didn't give a response. The rest of the room had broken up in laughter.

"Well, now know sir, that you are very special and your work doesn't go
unnoticed." I then led the boardroom in a rendition of "For He's a Jolly
Good Fellow." By the time I was done, my face was beet red, but I doubt it
showed under the heavy layers of makeup.

I gave him the balloons and left the room, hearing him saying, "I don't know
what I did to deserve this." The funny thing is, I had chosen him at
random. I didn't work for a balloon delivery company.

Stepping out of the office building, I got into the car, glad that it was
over.

"Well, how did it go? Did you pick somebody from management like I asked?"
she asked me. Mistress always wants to know how it went!

Sissy mission accomplished.