Totally Tiffany
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Totally Tiffany
I
I don't remember when it started. It seems as if my earliest memories
are of wanting to be a girl. I grew up in a family that was typical of
middle class America, mom and dad both worked to support us. I had an
older brother and two older sisters. Being the baby of the family had
both its advantages and its disadvantages. I learned to live with it.
My brother Jake was five years older than me and was my arch nemesis.
We fought more often than not, and I was the one who walked away with
the bruises. My sisters Beth and Anna were one year and two years
older than me and we were always much closer than Jake and I were,
therefore I spent far more time with them while growing up.
I do remember as early as first grade sneaking into my sisters' room
and trying on their clothes when nobody was paying attention. It gave
me such a thrill. Throughout my school years I continued this routine,
even making up reasons to stay home when the whole family was heading
on an outing. By the time I was in high school I was getting pretty
good with make up and could pass for a girl as long as I stayed away
from any direct scrutiny.
My college years gave me freedom to explore, but I forever felt that I
was going to get discovered. I acquired a decent wardrobe but stayed
in my apartment out of fear of getting caught. After finishing college
and law school, I got married to a girl I had met in college, and
started working for a major law firm in Chicago. I assumed that my
days of dressing were over and I tossed out my entire collection of
clothes.
Barbara and I had a wonderful marriage and started our life together
with optimism and promise for the future. She had graduated with
degrees in Political Science and International Affairs. She took a job
as an advisor to a political action committee and frequently traveled.
We bought a house, new cars and took vacations to exotic locations. In
general life could not have been better.
It was during one of Barbara's trips over seas that the old urge hit
me. She had been gone for a week and was not due back for another two
weeks. It was the longest that we had been apart since we were
married. I started getting horny, and without her there to take care
of my needs, one thing led to another and I soon found myself
exploring her closets.
That first afternoon, it started with a quick hour of dress up. Bra
and panties, pantyhose and a dress, shoes, jewelry and makeup, and I
was ready for some quick relief. I changed clothes as fast as I could,
being careful to put everything back where it belonged. For the rest
of the day I sat around feeling guilty, but when bedtime arrived, I
headed right back to Barbara's dresser for a nightgown to wear.
At 5' 10" tall and 155 pounds my build was rather slim. Barbara was 5'
7" and 126 pounds. She wore a size nine and although some of her
clothes were a little tight, I could fit into almost everything she
had. Since my feet are small, my size 7 men's fit into most of her 8 ½
women's with just a little squeezing. It didn't take long for me to
start looking forward to her trips out of town.
Barbara and I both enjoyed success in our careers. For me, this meant
promotions and a much larger salary. For Barbara, this meant a lot
more travel and a little more salary. I was on the fast track with my
firm and planned on being the youngest partner in the history of the
firm. My long hours at the office were quite often offset by evenings
and weekends exploring my feminine side.
Over time, I became more confidant in my look when enfemme. I had
purchased an expensive blond wig and felt that this was the final
touch needed to make me totally passable. With my newfound confidence
I started heading out into the world on a regular basis. At first, it
was late night drives through town or a quick walk in the park. Later
it became stops at the mall and trips to bars. I was very certain that
I was good enough to never get recognized. This was my first mistake.
At work, things continued to go well. The only problem that I had was
when I let my ego get in the way. This seemed to happen more often
than not with some of the female attorneys. I worked hard and so did
they but I took every opportunity I could to put them down. It was
that much less competition for the promotions. This turned out to be
my second mistake.
The one female attorney that did earn my respect was Stephanie Wilson.
She was very bright, very good looking and for some reason very
approachable. Most of the female attorneys tended to be quiet and
within themselves. Stephanie was just the opposite. She was outgoing,
easy to talk to and very, very competitive. She was not married, and I
started having an affair with her. This was my third and biggest
mistake.
Stephanie and I had been seeing each other for several months and I
now had another reason to look forward to Barbara's frequent trips.
After our dates, we generally ended up at Stephanie's place for our
sexual activity. She lived by herself and this gave us a higher degree
of safety. I was not concerned about Barbara catching us, but you just
never knew about nosey neighbors.
Recently, Stephanie had started talking about a long-term
relationship. She had even gone so far as to suggest a divorce so that
we could get married. I tried to talk sense into her but she would
have no part of it. She tried everything she knew to convince me, but
in the end, I held firm.
As part of Stephanie's plans to convince me to divorce Barbara, she
started planning long weekends at her place whenever Barbara was out
of town. This resulted in several things happening. First of all,
since we were expected to work at least two Saturdays a month, I
needed to have extra clothes at her apartment. Soon, I had six or
seven different sets of clothes hanging in one of her closets to use
after a Friday night spent there. Second, since my clothes were
hanging in one of her closets, I started having chances to explore her
closet a little closer. Third, since our monthly schedule was never
fixed, I ended up with several Saturdays at Stephanie's apartment
alone. This was a dangerous situation that ultimately blew up on me.
Stephanie had great taste in clothing, and she had a great body to
show it off on. She was 5' 10" tall just like me and weighed about 120
pounds. She wore a size 7 dress and a size 9 shoe. I was soon to
discover that while most of her clothes either would not fit, or were
very tight; there were enough that would fit to keep me happy. And
best of all, her shoes fit perfectly. I even found a long brown wig in
the back of her closet. I was in heaven, a whole new wardrobe to play
with.
It was a Saturday in March when it finally happened. Stephanie was
scheduled for a marathon session with an attorney from out of town.
They would start at 10:00AM and probably work through dinner. She left
early before I was out of bed, "You don't need to stay around and wait
on me. When I get done I'll give you a call and maybe we can meet
somewhere for a drink." That was it, my free ticket to a full day of
playing dress up. The weather was terrible and I had no other plans so
it was a perfect day to stay inside and play.
Stephanie was barely out the door when I got out of bed and headed for
the shower. I was fortunate that I did not have much for body hair so
shaving off what was there would hardly be noticeable. I really wanted
today to be special. When I dried off, I used some of Stephanie's skin
lotion and bath powder. I felt soft and smooth and wonderful. After
drying my hair I headed to her closets to pick out my outfit.
I already had a good idea of what I wanted to wear, but I wanted to do
some browsing anyway. After spending some time checking out several
different outfits, I settled on the one that I had in mind from the
start. It was a dress that I had seen Stephanie wear several times to
the office. It was both very professional and very sexy. It was red
silk with a hemline that hit at mid thigh, perhaps a bit short but
still acceptable in today's business world. The waistline was fitted
and the skirt flared slightly from there. The top of the dress was cut
low enough to be suggestive but not so as to be improper.
With the dress selected, I went about choosing the rest of the outfit.
The lingerie was white in soft nylon and lace. The bra was under wired
and padded which helped to give me a modest bust line. I selected
pantyhose in a suntan shade that helped to improve the look of my legs
and then added a panty girdle to hold everything in place. A white
slip helped to give me a smooth look in the dress. The shoes I chose
were red pumps with a four-inch heel and ankle strap.
I sat at Stephanie's dressing table for almost an hour trying to get
the makeup just right. When I was pleased, I selected gold jewelry and
pulled the wig into place. The wig was pre-styled and fell to shoulder
length, so all that was necessary was to brush it a bit. I used some
of her Shalimar perfume and was ready for anything. Well, at least I
thought that I was.
I walked around the apartment for a while and even tried to watch a
little TV, but I wanted more. Finally I decided that looking this
good, that I needed to get out. I grabbed one of Stephanie's purses,
threw a little cash into it and headed to my car. I drove across town
to the mall, one of my favorite places to be seen, with out being
seen. I spent some time walking around doing a little window-shopping
and even got some lunch in the food court. Finally around 3:00 I
figured that I better be headed back.
I was only a mile from the mall when disaster struck. A flat tire! Now
I had changed flat tires before, but never when I was dressed like
this. I pulled over to the side of the road and settled down my
nerves. I was just preparing to get out and change the tire when the
situation turned worse. There in my rear view mirror was a police car,
red lights on and the officer getting out of the car.
"Can I help you miss? It looks like you are having a bit of trouble,"
he said being ever so gracious.
Well, he did call a towing service and they came out and changed the
tire, so I survived that much. After paying the mechanic, I was about
to leave when it got worse again. It was the police officer in his
cheerful voice, "Miss, I am going to have to see your license. I need
to fill out an incident report and account for my time. I promise, it
won't take but a minute."
I didn't know what to do. I stalled for time digging in the purse like
I was looking for the license. Finally I looked up with as sad of eyes
as I could manage, "I guess that I don't have it with me. I am sorry,
but I changed purses this morning and I must have left it in the other
purse." I smiled and tried to look helpless. It didn't work.
The officer returned my smile. "I am sorry to have to tell you this,
but I will need to give you a warning ticket for not carrying your
license with you. You will need to take your license to the police
department downtown within ten days to clear the ticket. If you don't,
there is a $150 fine to pay. Now, could I have you name and
registration for the car?"
Now, my mind froze again. My name? The registration? What was I going
to do? I looked at the officer and tried to smile, but that got me
nowhere. My brain was racing 100 miles per hour. I couldn't give him
my name dressed as I was, but what else could I do? The other problem
was that the registration was in my wife's name since I was driving
her car while mine was in the shop. Finally, that was the solution I
arrived at, I reached into the console and pulled out the registration
and handed it to the officer, "Here you are officer, and there is my
name right on the card, Barbara Mears. I really am sorry for not
having my license with me. I will be sure to get down to the station
right away getting this taken care of."
Finally, the officer warmed up just a bit. "OK Miss Mears, since I see
that you have you registration and insurance requirements covered, I
am going to cut you a break this time. I am going to run your plate
for ID, and as long as it comes back without issue, I'll let you slide
just this once."
I sat there for another ten minutes while the officer ran the plate
and came back to tell me that everything would be OK. He gave me
another stern warning about carrying my license with me, and then gave
me a smile and sent me on my way. I took a deep breath and pulled
away. I drove carefully back to Stephanie's apartment just to make
sure that I didn't risk another incident.
By the time I got back to Stephanie's, it was after 5:00. My heart was
racing knowing that my time was growing short if I was going to get
changed and have everything back where it belonged before she got
home. I had to park near the opposite end of the lot in order to find
a place and hurried down the sidewalk not paying attention to the
surroundings. If I had been just a little more observant, I would have
seen Stephanie's car parked just across the aisle.
I entered the main hall of the apartment building and made my way down
the hall to Stephanie's apartment as I turned the key in the lock, my
heart started to settle down. I entered the living room turned on the
light and took three steps across the room when I met Stephanie coming
out of the bedroom. We both stopped where we were. The look on her
face went from shock, to confusion, to recognition. As I watched, I
knew that I was screwed. No matter what, my life had just changed, and
it was not going to be for the better.
Stephanie smiled wickedly at me. "Well, well, it looks like my Thomas
has been keeping a secret from me. Or should I say Thomasina? Well
don't just stand there looking like an embarrassed little girl, come
tell me all about this. I just can't wait to hear this story."
From that moment on she owned me, and she knew it. We sat and talked
for hours. I wanted to change but she would not let me. I told her
everything there was to tell; from the time I was six and first pulled
on my sister's panties, to the traffic stop this afternoon. She was
totally enraptured with my story. She made me stop for a while and she
got her digital camera. She had me pose in several positions and took
a whole series of pictures. By the time I was done, I was in tears. I
just wanted to change clothes and have it all be over with, and I told
her that. She smiled and told me to dry my tears, "This is far from
being over my little one, as a matter of fact; I believe that this is
just beginning."
I sat there grimacing as Stephanie laid down the new rules for our
relationship. "First of all, I think that we shall find all sorts of
ways to explore this new side of you. Secondly, you will dress when I
tell you to, how I tell you to and act exactly as I tell you to or I
will find all sorts of clever ways to provide punishment. Third, I
think that our relationship overall should take on a more significant
role in your life. I realize that you might be challenged to make up
new excuses for your wife, but I would bet that she has no idea about
this little game of yours. Last, I may choose at any time to provide
you with challenges that you may find embarrassing, demeaning,
unappetizing or otherwise distasteful. You will however in all such
cases reply, respond and react exactly as I require you to do. In the
event that you choose not to do so, just remember the pictures that I
just took. I will be placing these in a very special location on the
Internet where they can be made instantly available to anyone,
including your precious little wife and the senior partners of the
firm. Now then my dear little one, do we have an understanding?"
I looked up at her with tears in my eyes. "Yes, we have an
understanding."
She looked at me scornfully. "I am sorry, but to whom were you
addressing that comment. Was that to just anyone, or was that to your
loving Mistress?"
I looked up again, and then cast my eyes downwards. "I am sorry
Mistress, I fully understand the agreement that we have reached."
Now she smiled. "Well that was easy wasn't it? Now, I think that a
little celebration is called for. Why don't you run out and pick up a
good bottle of wine and some food to go with it. While you are gone I
will bathe and change clothes. When you return you can pamper me for
the rest of the evening. Then tomorrow, I believe that you would like
to take me to dinner, wouldn't you dear? And you do know that my
favorite place in the whole world to dine out is the new five star
French restaurant downtown, don't you? I know that it is a bit on the
expensive side, but I am sure that you want to make a very good
impression on me, don't you my love? Now then, why don't you dry your
tears, make the reservation and run and get the food and wine. Then
come into the bedroom and we will pick you out an appropriate outfit
and try to get you looking presentable."
I had no choice. She had enough of a story along with pictures to ruin
me. I found the number for the French restaurant and made the
reservations. Then I looked in the mirror and repaired my makeup from
what I had in the purse. I headed out to a gourmet food shop that I
knew and pick up a light dinner for two. It contained a light salad,
various cheeses with crackers and a fruit plate. I found an excellent
bottle of Chardonnay to go with it. Just in case it would help to
sooth her nerves, I picked up a second bottle of the wine. On the way
back to the apartment I found a little flower shop that was open late
and purchased some roses. Anything that I could do at this point that
might help to improve her attitude I would try.
When I made it back to the apartment, I laid out the dinner and put
the wine to chill. Slowly, I made my way to the bedroom where
Stephanie waited. When I entered, she was sitting at her dressing
table. She was wearing a long white nightgown and matching robe. I
looked at her meekly and stopped in the middle of the room waiting for
instructions. They were soon forthcoming.
"Strip!" she barked. "Then get over here where I can see you."
I started to undress, and she turned to watch. Soon I was standing
there wearing nothing but the pair of white panties.
She got up and walked across the room checking me out. As she moved
around behind me I suddenly felt a firm slap on my ass. "It is obvious
to me, that there is much work to be done here. When I give you a
simple order, and you cannot even complete it satisfactorily, it shows
me that there is a great need for training. Now, get those panties off
while I decide what your punishment should be!" With that, she slapped
me firmly on the ass again.
I dropped the panties and stood quietly. After several minutes, she
ordered me into the shower, telling me to return when I was properly
cleaned. When I returned, she was again seated at the dressing table.
On the bed, she had laid what was to be my outfit for the evening.
There was a red bustier that laced up the back and a pair of red
stockings that would attach to the garters. There was also a matching
thong panty. A pair of red slip on shoes, also in red, with four-inch
heels set on the floor.
Smiling, Stephanie headed for the door. "When you are dressed, make
sure to do your make up and your hair. I realize that it is not very
long, so you will have to be creative. You have seen girls with short
hair before. Just try to remember how they did their hair. I am sure,
that you will come up with something appropriate. Remember, you will
be judged on your final appearance so do a good job. Make sure that
you hurry, I will be enjoying the wine and waiting for you to serve me
dinner."
I emerged from the bedroom, ½ an hour later. Stephanie was sitting on
the sofa with a glass of wine, looking through a fashion magazine. "Oh
my, don't you look precious? You know, with a little work, I think
that we can make you into quite the presentable little lady. Now, pour
me some more wine, and serve me my dinner. Then when I am satisfied,
you can fix yourself some also."
When I had served her, and obtained her approval, I fixed my own
dinner. When I came into the room with my plate of food and glass of
wine she stopped me. "That's totally wrong for a young lady like you.
You will get fat and lazy if you eat that much. Now I want you to go
back in the kitchen and remove half of everything from your plate.
Then, you may sit with me to eat."
On my second trip into the room, she inspected my plate and approved.
As I moved towards the sofa, she motioned to the floor. "At my feet,
you will kneel there as you eat. That is the appropriate place for a
young slave girl!"
After dinner, I cleaned the dishes and put them away. Stephanie
watched my work from the living room where she had consumed more of
the wine. I hoped that it was having the desired affect, but I was
growing doubtful. When I was done, she motioned me to the bedroom. "We
still have the matter of punishment to address before bedtime."
Once in the bedroom, Stephanie removed her robe and climbed onto her
bed. "You know slave girl, I would be in a much better mood, and
probably much more lenient, if you were to find some way to help me
relax. Why don't you crawl up here along side of me and see if you can
put your tongue to any good use."
An hour later she was coming down from her third orgasm when she
decided it was enough. "You have done well. You almost, but not quite
made up for your earlier indiscretions. Therefore, you must still be
punished. Now, I want you to stand at the foot of my bed and wait,
while I get things ready."
When she returned to the room she was carrying a number of things. She
stayed behind me so that I could not tell what they were. She ordered
me to the bathroom to ‘take care of any business that I required', and
then back to the foot of the bed. Her bed was a metal-framed canopy
style. When she had me bend over the footboard, I began to get
nervous. Looking back, I saw her holding a large enema bag along with
several types of fittings.
"I believe that a slave must be clean both inside and out. Therefore,
I will need to show you how to take care of the internal cleaning.
Now, hold still while I get you ready."
Stephanie hung the enema bottle from the canopy frame and got busy
with the hoses and fittings. Suddenly, I felt her smear something cold
on my ass. This was soon followed by her finger moving around and
finally into my tight hole. Before I knew what happened, a plastics
tip replaced her finger and it was pushed firmly inside of me. I
squirmed and squealed, earning a sharp slap on the ass. I knew that I
had better hold still.
When I settled down, I heard a faint noise of air being pumped. As I
felt it I realized what it was. Stephanie was using a small squeeze
ball to pump up what ever it was that she had placed in my ass. "We
just want to make sure that everything stays in place." She quit
pumping and removed the ball. When she gave a taught pull on the hose
that was now attached to me, I knew that it would not come loose. She
connected the loose end of a hose to a fitting that was on the bag
hanging over my head. She opened a valve and let the solution fill the
hose replacing the air in it. She then closed the valve. She now
reconnected the second end of the hose to the fitting in my backside.
Before I even had time to think about it, she opened the valve and the
force of gravity started the fluid moving again.
I felt it inside of me almost immediately. It was cool and created a
slight burning inside of me. "Don't worry my pet. You will soon get
used to this feeling. I believe in regular thorough cleanings." It
took only minutes for the bag to empty and for me to feel full. When
it was done, Stephanie waited only a minute before she shut off the
valve. She disconnected the hose at the bag and laid it up over my
back. She had me stand upright and reach over my shoulder to grasp the
hose. "Now, hold it firmly. As long as you keep it high, the solution
cannot flow back out." She had me walk to the bathroom and then lower
the hose into the toilet. The solution flowed out in a steady stream,
propelled by the pressure of my contracting intestines.
When I was done purging, I moved back into the bedroom. Much to my
disappointment, Stephanie had hung a second bottle from the canopy
frame. This bottle was much larger and the solution looked much more
ominous. It was pink and looked thick and heavy. This time as
Stephanie moved me into place, she tied my ankles to the rail on the
footboard. She then pulled my hands over my head and tied them tightly
to the canopy frame near the bottle.
She stepped behind me, hooked the bottle to the hose and turned on the
valve. Just as I thought, the fluid moved very slowly down through the
hose towards its final destination. "This will be fun. With this
solution, and the medium sized bottle, it should take 40 or 50 minutes
to fill you up completely. When it is done, you will feel like you
swallowed a pumpkin. That's when the real fun begins." She lay across
the bed and watched.
As the pink fluid found its way inside of me, I knew that this was
going to be no fun at all. It had the feel of something solid, but
slowly, bit-by-bit, it kept growing. It also had a secondary effect;
it created an itch deep inside of me. The more it filled, the more I
itched. Soon, I was wiggling my butt like a sex crazed schoolgirl
trying to get some relief. Stephanie looked up at me and smiled.
"Getting to be fun isn't it. Now let's add something more.
She moved to the dresser and picked up two little shiny balls each
about ¾ of an inch in diameter. As she approached me, I saw that they
had small clamps attached to them. She quickly clamped them onto my
nipples and gave them a little tug. As if the force of the clamps
weren't enough, the balls bounced and swayed. "They are hollow, and
filled with Mercury. The way that you are wiggling your ass, it is
sure to keep these babies moving for you."
I opened my mouth and started to protest, and she slapped me. "Slaves
must always be quiet unless spoken too. Now open wide." As I did, she
picked up a red rubber ball and pushed it into my mouth until my teeth
clamped it. I tried to use my tongue to push it out but could not.
"Now let's see just how well it works." With that, Stephanie reached
out and pulled hard on the nipple clamps setting them bobbing to and
fro. I screamed, at least I thought I did. All that came out from
behind the ball was a long, low squeal.
I hung there for the better part of an hour before Stephanie was
satisfied that the enema bottle was empty. Finally, she stepped behind
me and started to disconnect things. This is when I realized that
there was another valve at the receiving end of the enema system. This
time, she closed this valve securely maintaining the full load of pink
fluid inside of me.
By the time that she untied me, I was about to go out of my mind. The
constant itch that kept me wiggling had also kept the nipple clamps
moving. The pain was incredible, but at the same time, I now had an
erection. "See my dear. Even the punishment comes with some rewards.
Now I want you to kneel at the foot of the bed, and you can go ahead
and relieve yourself."
I didn't have to ask what she meant. I kneeled there, took a grip on
my manhood and started to massage it. That was when I found out about
her next surprise. "Oh, did I forget to tell you? That wonderful pink
medicine not only creates that itch inside, but it has the added
benefit of reducing your sensitivity to touch. It will probably take
you a while before you achieve a climax, but you need to keep working
at it. When you do, then we will see about getting you drained out and
put to bed."
Never in my life had it been so hard to achieve a climax. I worked at
it every way I knew how. Stephanie just sat back and watched. Little
by little, the feeling would build, and then my arms would be so tired
that I would slow down and loose ground. At long last, she took pity
on me. She moved behind me and reached around my waist grasping my
member and helping me to finish. When I finally came, I thought that I
was going to collapse. As I knelt there, Stephanie caught every drop
in a small cup. When I was done, she reached up and pulled the red
ball from my mouth replacing it with the cup. She poured it all into
my mouth while telling me to swallow, and not to waste a drop.
I moved to the bathroom and Stephanie removed the device from my ass.
She had me sit on the toilet. The pink fluid came out almost as slowly
as it went in. While I sat there, she removed the clamps from my
nipples. This caused such a wave of pain that I almost passed out. She
told me to sit until I was sure that I was empty and then clean up and
come to bed.
Almost an hour later, I made my way to her bed. When she saw me
approach, she handed me a blanket and pointed to the floor at the foot
of the bed. "That is the proper place for a slave girl to sleep."
I threw the blanket down and curled up there falling to sleep quickly.
I was tired and sore, and worse yet, I knew that there was more to
come tomorrow, and the next day.
Sunday started up right where Saturday night had left off. I had to
fix a bath for Stephanie and help her to get dressed. I fixed
breakfast and served her while still dressed in the red outfit from
the night before. When she was done, she headed out to visit with
friends, I was left there to clean up the apartment, take a shower and
make myself presentable. When she returned, we would decide what to
wear for our diner date.
I spent the afternoon making the apartment look as good as ever. I
cleaned and dusted, vacuumed and polished. The kitchen was spotless
and the bedroom was put back together after last night's ordeal. I
picked up the enema bottle and other pieces and laid them in the
bathroom. When everything was done, I took a shower and picked out
something to wear. I kept it simple, yet picked something that I knew
Stephanie would approve of in her current state of mind. I chose a
black skirt and white blouse that were both simple and subtly sexy. I
added black panty hose and heels. I used her wig again and added
simple jewelry and soft make up.
When I was done, I thought that I looked quite presentable. I sat in
the living room waiting for Stephanie's return. Minute by minute, I
thought about how she was about to turn my life into a living hell.
The problem that I had was that I could see no way to stop her. With
the pictures, and the story that she could tell, I would lose my wife,
my job, and my whole life style. I would just have to play along until
the right moment. Life always presented opportunities to get even; I
just had to be ready when it happened.
When Stephanie returned, I had made the mistake of falling asleep on
the sofa. She was irate. "This calls for another punishment! Now stand
up here and let me look at you. We will take account of your
appearance and the job you did cleaning the apartment. I will assign
you demerits, and you will keep count. Do you understand?"
I looked at her trough still sleepy eyes, "Yes mistress, I understand.
You assign demerits and I keep count."
"Good, then let us begin. Your clothes are wrinkled, that will cost
you five demerits. Your hair and makeup are fair, that will only cost
you two demerits. Your fingernails look terrible. Couldn't you at
least have made an effort? Two more demerits."
After the personal inspection, she proceeded to inspect the house. The
toilets were not cleaned, five more demerits. The trash had not been
carried out, two more demerits. And finally, the towels in the
bathroom were not folded properly, another demerit. The total came to
seventeen demerits.
We sat in the living room while Stephanie decided on an appropriate
punishment. I was genuinely worried; I did not want a repeat of last
night. When she was done thinking about it, she ordered me in to the
bedroom. I stood at the end of the bed as she instructed. She had me
drop my panties and pantyhose to my ankle and lift my skirt to my
waist. She then bent me over the footboard and told me not to move.
She left the room for a minute and when she returned she showed me
what she had gone for. It was an oak cutting board, one inch thick,
eight inches in diameter with a long stout handle. It was part of a
cheese cutting set, but would serve well as a paddle.
"I want you to count out each swat for me in a nice loud voice. There
is nothing like a good paddling to make a girl remember to try harder
next time."
Stephanie used all of her strength to swing the paddle. The first swat
brought tears to my eyes and by the sixth one I was crying freely and
pleading for her to stop. It was after the tenth swat had landed that
she quit. My knees were buckling and I could hardly stand. She stepped
back and surveyed her work. She rubbed her hand on my butt feeling the
welts that she had left. "My but you are red on the cheeks, and very
warm I might add. Now, get your self together, we have some shopping
to do."
I cleaned up as best as I could and Stephanie said that I looked good
enough for now. We took her car and she drove out towards the mall.
"We need to get you some things of your own. I don't think that it's
fair that you should get to borrow my things. Most of them don't fit
you properly and I don't want them ruined."
I tried to argue with her but I knew that it would do me no good. When
we got to the mall, the first place we went to was a small dress shop.
All of the clothes were very pretty, and very expensive. We were
looking at a rack with spring and summer dresses when a clerk walked
up and asked if she could help. The girl was about eighteen years old
and looked like a high school cheerleader. I tried to shy away and
keep looking but Stephanie would have no part of that.
"Yes, I am sure that you can help. This is my boyfriend and he is
looking for a dress for a very special date tonight. It needs to be
something of exceptionally good taste but at the same time something
sexy. Do you think that you can find him something?"
The young girl stopped where she was. She seemed to be thinking for a
minute to make sure that she had heard correctly. She looked at me and
smiled and then looked to Stephanie. "Well I think that we can find
him something. Is his date with you, or does he have a boyfriend of
his own?" She giggled as she asked this. "Do you know what size he
wears, or do we need to measure him up?"
By the time we left the store, I had purchased a white dress made from
a soft shiny fabric that had a pattern of roses woven into the
material. I had tried it on and it fit very snugly, but Stephanie said
we would take care of that later. The skirt came only to mid thigh,
and the neckline fell to bust exposing level. She said that we would
fix that also.
The next stop was at Victoria's Secrets. Stephanie walked right up to
a clerk and told her what we needed. "My boyfriend just bought a new
dress for our date tonight and he needs some help with his figure. I
was thinking of an over bust corset with firm boning and added lift."
The clerk looked at me and smiled, "Don't worry dear. You are not the
first and you won't be the last. I have worked here for five years and
I have probably fit as many men for corsets as I have women. The men
always pose a bit more of a challenge, but I am sure that we can give
you the curves that you are looking for."
When we left the lingerie store, I was wearing the corset. It was
heavily boned and gave me a slim waist that flared to my hips, which
now seemed rounder. The under wire supports and padding in the bra
section gave me a reasonable bust line. I had on the matching panties
and shear white stocking that attached to the garters. Our next stop
was the shoe store where I bought a pair of white multi strap sandals
with three-inch heels. Stephanie wanted something higher but settled
on these so that I would have an easier time walking in them.
We bought jewelry, a purse, some makeup and perfume before we were
done. At each store, the clerks would laugh as they saw the name on my
credit card. "Here you are Thomas. Now enjoy you new dress, or your
new shoes, etc". I blushed bright red every time but there was nothing
that I could do.
When we finally left the mall and were driving back to the apartment,
Stephanie said, "Well, that will take care of five demerits, only two
more to go."
At the apartment, Stephanie was in a frenzy of activity. She showered
and dressed, fixed her hair and did her makeup. She wore a midnight
blue dress that looked great on her. She was the picture of elegance
and femininity.
She had me shower while she was dressing and then helped me to get
ready. I could have gotten dressed myself with the exception of the
corset. I thought that it had been laced tightly at the store, but
Stephanie managed to pull it in another inch. By the time that she was
through I wasn't sure that I was going to be able to breath. The dress
now fit very well. The corset had pulled me in where it had been snug
and added curves to fill it out.
Stephanie spent extra time doing my makeup and then placed the wig on
my head and brushed, combed and sprayed it into place. When I looked
into the mirror I was amazed, I had never looked so good. Stephanie
said that it was OK, but I would get better with practice.
Dinner at the French restaurant went well. The prices were incredible,
but I just shrugged and went with the flow. We had finished dinner and
were having an after diner drink when Stephanie decided it was time to
pay off the last two demerits.
"I want you to go to the restroom. While you are there, take care of
anything that you need to and fix your makeup. When you are done, I
want you to take off your panties and put them in your purse. Then
come back to the table and we will have another drink. Maybe we'll
visit the bar for a nightcap before we leave." Her smile told me this
was an order and I had better go.
I made my way to the restroom and quickly took care of business. I was
standing at the mirror fixing my lipstick when an older lady came in
and stood next to me checking her makeup also. She touched it up
quickly and then turned to leave. Before she left however, she turned
and spoke to me, "I give you a lot of credit dear. It must be quite
difficult to go as far as you have, and you are very near to being
totally passable. Let me give you some advice, work on the way that
you move. I noticed you when you walked across the restaurant, and I
noticed your movements just now when you did your lipstick. Your
movements are a little forced and stiff. Girls flow when they move.
One motion leads into another. I am sure that with a little practice
you will do just fine. I know you fooled my husband, he watched you
wiggle all the way across the room."
She left the room and I was scared stiff. If this old lady had figured
me out, whom else knew? How could I go back out there? I was sure that
everyone would be watching for me and would break out in laughter when
I walked out. I stood there for several more minutes getting my
confidence pulled together. When I did, I got ready to go, but stopped
a step before the door. I still had my panties on. If I went back to
the table with them on, no telling what Stephanie would do?
I retreated to one of the stalls and pulled them down and stepped out
of them. I picked them up folded them in half and tucked them into my
purse. When I took my first step, I discovered my latest problem. With
out the panties, I had nothing to hold my male parts up and out of
site. It might not have been so bad with a different outfit, but with
this short, tight skirt, there was little to provide cover. Worse yet,
while I stood there thinking about it, I started to get an erection.
Now, I was in real trouble.
After standing there fore several more minutes deciding what to do, I
chose to deal with it the old fashioned way, I masturbated. It didn't
take long, and no one came in while I was doing it. When I was done, I
used wet paper towels to clean up. I used cold water to help things
shrink and it helped. I knew that I could stand and walk with out too
much trouble, but I would have to be very careful when I sat.
As I approached the table where Stephanie and I had been sitting, I
could see that she was gone. Our waiter showed me to the bar, and
there she sat at a small table on a high stool. This was going to make
things very difficult. I walked over to where she was and stood next
to the stool. It had arms and a back but was very tall and would
require a step up on the footrest to get seated. I held my legs as
close together as I could and stepped up. I rotated quickly to a
seated position making sure to smooth my skirt under me as I did so.
"Very good. I thought that you might have more trouble getting on the
stool, but you handled it well. Now open your purse and let me see.
Watching how you moved, I am quite certain that you did as you were
told, but I still think that I had better check." She looked into my
purse and smiled. "Now tell me, what took you so long in there? Even
real girls don't take that long."
I told her the story about the lady that had talked to me. "If she was
able to figure me out, who else do you think could tell? She made it
sound as if it were obvious to her."
Stephanie smiled, almost letting go with a laugh, "Well, I would
venture to say that any of the women here tonight could tell if they
looked at you more than once. But I will bet that the only men that
noticed were the gay couple sitting across from us. I think they
figured you out quickly. I don't think any of the other men saw you as
anything except a desirable woman. Now let's have a drink, and then we
can go home. I have an itch that needs scratched, and you'll be doing
that scratching for me."
For the next year and a half we played this same game. Stephanie took
advantage of the situation she had me in to provide her amusement and
entertainment. She became increasingly more cleaver in finding ways to
embarrass and expose me. She continued to document my torment by
taking pictures every time I dressed and of the many little scenarios
that she led me through.
She pushed me to leave my wife, but I insisted that I couldn't do it.
We would argue about this often. I could tell when she was upset about
it because she became more devious in her punishments. Over time, I
had acquired a French Maids' outfit that I wore while cleaning her
apartment and serving her dinner. I also had a little girl's dress and
pinafore that she dressed me in and took me to the park, taking my
picture sitting on the swings. I had a number of dresses in casual
styles as well as eveningwear. I had spent more than a few thousand
dollars on the outfits that she had made me purchase. Also, she had
made me purchase most of them in person, while letting the sales
clerks know that they were for me.
At work, things had gone much better. I had received another
promotion, being selected as a department manager. Stephanie was upset
about it because one of her best friends had also been in the running
for the position and I was chosen over her. In general, I did not get
along with many of the women attorneys in the office, so this gave me
a little boost in the ego department. Stephanie warned me not to get
too full of myself, but I didn't see it that way. Here at the office,
these women reported to me, and I took pleasure in the fact that at
least here, Stephanie didn't have such a firm grip on me. I was soon
to find out how wrong I could be.
Barbara and Stephanie had met at an Awards dinner that the law firm
gave annually. Some of the awards were based on personal performance
and accomplishments and others were just fun things to keep the
evening interesting. I had tried to keep them apart, but in the end
was not able to do so. By the end of the evening, they were chatting
like old friends.
Unbeknownst to me, Barbara confided in Stephanie that some of the
spark had gone out of our relationship and that she was afraid that I
was working far too much. "I know that I take long trips for my job,
but I am afraid that Tom sees these as opportunities to put in extra
hours at the office. Sometimes when I get home he is so worn down that
he is not even in the mood for sex. Well, he has a birthday coming up
in two weeks and I am sure that he is expecting the same night out for
dinner that we always have, but I am planning something different. I
am giving him a surprise party, and then a long weekend of every
lustful activity that I can think of. That should get him back to his
old self."
When I ran into Stephanie the next day at the office, she was almost
violent. "I want you to divorce her! You have been holding out on me
for too long and if you don't do it now, I don't think that you ever
will. I want your answer today, and it had better be the right answer.
If its not, I am going to do something truly diabolical, I promise you
that!"
I spent most of my day thinking about Stephanie's threats. At last I
had come to a decision. I would not give in. If she wanted to expose
me, she could go right ahead and do it, but I was sure that I could
deflect most of it and patch up the rest. I needed to get back control
of my life.
When I met her after office hours, I told her what I decided. The
anger boiled, but then seemed to subside. She became apologetic. "Tom,
I didn't mean it. You know that I would never hurt you. I am sorry.
If you are willing to give me little pieces of your time, I am still
willing to indulge in your games. Just don't cast me aside."
Well, this was much better. At last it seems we had found out who had
the stronger will. She could never expose me, because that would mean
that she would lose me also and that was something that she was not
ready to do. Now it seems that I had the best of both worlds.
As it turned out, Barbara was leaving town on Thursday and would not
be back until the following Saturday which happened to be my birthday.
She had made reservations for dinner and a room in town for the night
so that we could celebrate. This would give me the chance to use my
newfound power to the best of my advantage. I would spend the entire
week with Stephanie and meet up with Barbara on Saturday for what was
always a great weekend of uninhibited sex.
On Friday night, Stephanie couldn't wait to get to her apartment. When
we arrived, we hurried and changed into comfortable but sexy
eveningwear. She had planned dinner and for once she was serving me.
Things couldn't be going much better. The wine that she served was
excellent and I drank more than usual. By the time that dinner was
over I was quite tipsy. We sat in the living room and talked for a
long time. I wanted to get to the bedroom, but Stephanie had other
ideas.
When I looked her in the eyes, there was a new and different look
about her. I started to say something about it but she cut me off.
"Relax. Listen to my voice and relax. I want this night to be special,
so just sit here and relax."
I found that there was little that I could do but obey her. Every
muscle in my body seemed to be in the relaxation mode already. I sat
there looking at her beautiful eyes and listening to her talk.
"I gave you something in your wine tonight to help you to relax. Now I
want you to listen to my voice and continue to relax. When you feel
that you are totally at ease, I want you to close your eyes and
sleep."
It was a while later when I woke up. When I did, I felt more relaxed
than I had in quite sometime. As I came to, I became aware of another
person sitting in the apartment with Stephanie and me. I knew that I
should be concerned, but I was not. I was just relaxed and calm.
Stephanie looked at me and smiled, "Well, welcome back. We have a
visitor. Dr. Baxter, this is ‘Tiffany', my boyfriend. Tiffany, this is
Dr. Baxter. Say hello to her."
I smiled and said hello. I wasn't sure what was going on, but
Stephanie had called me Tiffany, and somehow that seemed to be right.
I knew that I should have a different name if I was her boy friend,
but she said my name was Tiffany, so it must be.
Stephanie and Dr. Baxter talked for a long time mostly about things
that I didn't understand. I felt so stupid. They would occasionally
talk to me in simple words and sentences and I understood them
completely, but then they would talk to each other about things that
didn't make any sense to me at all. Finally I heard Dr. Baxter say,
"Let me demonstrate." Then she looked at me and said, "Tiffany needs a
nap."
It was some time later when I awoke again. I remember hearing a voice
saying, "Wake up princess." Suddenly I was wide awake again and
sitting on the couch between Dr. Baxter and Stephanie. They talked for
a while longer and again I didn't understand a thing that they had to
say, until Dr. Baxter said, "Ready for the test?" She looked up at
Stephanie who was nodding and said. "Tommy is back."
With that simple statement, I was back. Me! Tommy! Not Tiffany! And
further more, I was aware of everything that had been done and said
tonight, at least most of it. All of the conversations that Stephanie
and Dr. Baxter had shared were sharp in my memory. I had been drugged
and then hypnotized. It had started with the wine, and when I was out
Dr. Baxter had shown up and finished the job. While I was under, they
had created Tiffany. Well, this was some kind of a joke and I was
going to clear things up right now. I reached forward towards Dr.
Baxter trying to get a hold on her. When I did, she would undo all of
the things that she had done.
"Freeze!" That one word stopped me cold. It wasn't just a reaction to
the spoken word, I could not move. Stephanie smiled, as she looked me
in the eye, "You didn't think that it would be that easy did you? Dr.
Baxter has given me a number of simple command words to aide in your
training. It will be so much easier when you realize that you no
longer have a choice, but until then, it is best if we have these
controls in place."
Stephanie came forward with some rope and began to tie me. She tied my
ankles together and then my knees. She tied my hands in front of me
and then secured my elbows to my waist. As a final act, she placed a
ball gag in my mouth and tied it behind my head. She checked
everything to make sure it was secure and said, "Relax."
Hearing this word, the freedom of movement was returned to me, except
that I was now bound into position and was going nowhere.
"Now while you are here, let me explain things to you. I need to do
this, because once Tiffany is back, she won't understand a thing.
She's a little slow sometimes." She smiled and went on, "It was very
disturbing when you decided that you could take control of our
relationship. I mean after all, look what I have done for you. When we
started our adventure, you were nothing more than a cheap slut of a
cross dresser. I made you into what you are today, a lovely very
passable young lady. It was totally unfair of you to think that you
could take away from me that which I had created. Well, with a little
help from Dr. Baxter, I have things in hand again. I wanted you so
badly when you were a man, now I will have you as a woman."
The reality of what she said was starting to sink in. Somehow, I had
let myself be programmed while under hypnosis. I listened as Stephanie
continued to speak. "I will let Tommy come around occasionally, but
most of the time you will be Tiffany. Do you like your new name? I
think that it is very feminine, soft and sweet just like you. Your
whole name will be Tiffany Olivia Mills. Isn't it pretty? Your
initials spell Tom isn't that cute. Every time you think about that,
or use your initials, you will remember for just a few seconds who you
used to be. Now, how often you are allowed to become Tommy again will
depend entirely upon your behavior, so it is important for you to
always be a good girl. Now, there is one more thing that you need to
do tonight. Dr. Baxter needs to be paid for her services. I am going
to untie you so that you can sign the check, and then you will show
how grateful you are to her. Do you understand? I want you to,
‘Behave'.
It was another of the control words. I was untied, but I just sat
there. Stephanie handed me a check, telling me to sign it and I did.
For what she had done to me tonight, I had just paid Dr. Baxter
$5,000. When I handed her the check, Stephanie looked at me and gave
the command. "Now that you have paid the bill, I want you to take Dr.
Baxter into the guest bedroom and attend to her needs. Make sure that
you do as you are told, or we will have to find an appropriate
‘punishment'." Another of the control words. A wave of fear swept over
me. I knew that I had better not fail to please Dr. Baxter, for
whatever the punishment was, I wanted no part of it.
When I woke up in the morning, I found myself tied hand and foot. I
was wearing a diaper and a pink nightgown and sucking on a large
pacifier. I tried to spit it out but I could not. It was not fastened
in place but I still could not spit it out. Dr. Baxter was gone and I
lay there remembering the escapades from last night. Her sexual
appetite was enormous. Mostly she had me use my tongue to fill her
needs but in the end, she had allowed me to enter her. She had yet
another earth shaking orgasm and this time I joined her. Funny thing
though, my orgasm seemed to disgust me. I felt dirty and cheap. The
doctor had consoled me, and that is when she put the diaper on me.
It was sometime later when Stephanie came in to release me. She smiled
when she saw me there. "The doctor has a nice touch don't you think
so?" I frowned and scowled and tried to spit out the damned pacifier
but I still could not. "Well don't you worry, I can see that you are
upset, but that's alright because, ‘Tiffany is here!"
With those words spoken, Tom was gone again and Tiffany was back. I
was happy and felt relaxed. I reached up and took the pacifier out of
my mouth and looked at it. "Stephanie, don't you think that I am too
old to suck a pacifier? I mean it feels good at night when I am going
to bed, but sometimes I think that I should give it up. What do you
think?"
"Well sweetie, I think that you can give it up any time that you want
to. But I also think that if you need to wear diapers to bed, then you
should use the pacifier also. When you are a big girl, you need to act
like a big girl, but when you are not, we will have to see."
I looked down at the diapers and turned red. "Did I have an accident
again? I'm sorry, I try so hard to not have accidents, but sometimes
it just seems to happen." I broke down in tears.
Stephanie held me close to her and patted my head. That is OK dear.
Accidents can happen. We will just have to make sure that when you
feel like a little girl that we remember to keep you in diapers. She
leaned forward and gave me a kiss on the forehead and everything was
suddenly better.
Going back to the office on Monday offered some relief from the
torment of the weekend, but my sense that I had any control of my life
soon spiraled downwards again. It was only 9:30 when I was summoned to
the executive offices to visit with Mr. Jessup, he was one of the
senior partners of the firm, and the one who controlled the division
in which I worked. When I entered the office I noticed that Mrs.
Karnow was also in attendance. She was from the HR department and it
was never a good sign if she was present.
Mr. Jessup started the meeting trying to be tactful and almost evasive
of the issue that he was trying to present, but Mrs. Karnow was having
none of that. She jumped right in and let me know exactly what was
going on. "Over the last three months, we have received several
complaints of sexual harassment from various women that you come in
contact with on a daily basis. As you well know, this firm takes a dim
view of this type of activity, as does the federal government. There
are strict laws that provide both for protection against this type of
behavior, and for specific actions that must be taken against those
who violate the rules. I will be working closely with Mr. Jessup on
the investigations into these matters. I warn you that this is a most
serious situation, and suggest that you cooperate fully. Also, if for
any reason you feel that this might compromise your position in terms
of moral, ethical or legal standards which govern this company, you
may choose at any time to terminate your employment with out loss of
pay or trailing benefits. If however the investigation should find
reasonable cause for dismissal, and you have not by that time made the
decision to voluntarily leave, you will be terminated with cause and
lose all benefits as well as any opportunity for unemployment
benefits. Have I made myself clear? Do you understand?"
I sat there dumbfounded. I didn't know how to answer. I knew that I
did not get along with many of the female attorneys in the office but
I had no idea of what I had done that could be considered that
offensive. I left the meeting shaking my head. My world had just gone
from bad to worse. I sulked back to my office and kept a low profile
for the rest of the day.
It was a little after 5:00 when Stephanie stopped by the office. This
was the first time that I had seen her today. I had been afraid that
she would have more surprises for me today after what she had pulled
yesterday. By now however, I was starting to feel that I had regained
at least some degree of control. She smiled and asked me if I had any
plans for the evening, and I knew that even if I did, she would change
them for me.
As it turned out, she decided that I needed a refresher course in how
to treat a woman properly, and that there was no better way to learn,
than to be put into a situation that would remind me of what a
pathetic man I was. By 9:00, I found myself dressed in a leather mini
skirt, halter-top, five-inch heels and hooker makeup, being dropped
off at a lesbian bar. I had strict instructions that I had to pick up
the biggest roughest looking butch that I could find. I then had to
have sex with her before I could leave the bar. There would be no
mistaking whether or not I was successful, because she knew that I
would ‘behave'.
That was it. Hearing the control word, I had no choice. Even though I
was conscious of what I was doing, I knew what I had to do. There
simply was no other option. I wiggled my way into the bar and surveyed
my choices. There were a lot of them, but I wanted to be sure to
choose the right one. Stephanie would not tolerate me making a quick
decision and selecting the wrong girl. I ordered a white wine and
started making my way around the bar. It only took one trip before I
knew whom my target would be. She was a huge woman, probably 6 feet 3
inches tall and 250 pounds. She wore blue jeans, a denim shirt and had
her hair cut in a long stand up spike.
I worked my way to the end of the bar and positioned myself to where
she could not miss seeing me. I talked to a few of the passer bys, and
flirted recklessly. It didn't take long before my bait worked.
"Hi, my names Melissa, can I buy you a drink?" She breathed down my
neck as she asked over my shoulder.
I looked up coyly as if I were thinking it over, and finally made up
my mind. "Well, I don't see why not. If you are kind enough to offer,
I should be kind enough to accept."
We sat at a small table near the end of the bar. As I scooted up onto
the stool I let my skirt ride up high on my thigh. This move was not
wasted on Melissa. We exchanged small talk, but it soon became clear
what was on her mind. She referred to it as needing ‘a fix' to get her
through the rest of the night. She suggested a back room at the club,
and we were soon on our way. It was beginning to look like this would
be easier than I thought, and I would soon be out of here.
When we made it into the room Melissa, (call me Mel), locked the door
and was on me like a lioness on her prey. With her first kiss, her
tongue explored the depths of my throat. Her hands were all over me
and her pelvis was grinding at mine. There was a small metal-framed
bed in the corner and she pulled me towards it. As I sat on the bed,
she pulled down her jeans to expose the men's briefs that she wore.
She quickly disposed of them also. Before I could say a word she
pulled my head to her waiting womanhood.
Melissa lasted through two orgasms before she collapsed on top of me.
I had no choice but to let her have her way. When she had finally
pulled my skirt up and my panties down, I started to find out how much
trouble I was. She hit me so hard with the back of her hand that I
thought that I would lose consciousness. She learned hard against me
putting her face right in front of mine and spoke I a low growling
voice, "So, what we've got here is a prissy little fairy boy. Well
fairy boy, let's see what you can do with that little piece of meat."
When she grabbed me with her hand, I thought that she was going to
pull it off. She massaged me until I was hard and then climbed on and
rode. I came quickly much to her satisfaction. "I can see why you
dress like a sissy boy, because you sure can't use that thing like a
real man. Well, I hate to let you go with out trying to let you
experience a little sex as a woman, so let's see what I can do to help
you out."
Before I knew what was going on, she had pulled a red bandana type
hankie out of her pocket, tore it in two, and was tying my wrists to
the frame of the bed. When I started to scream, she tore my panties
off and stuffed them in my mouth. She tore off a piece of the sheet on
the bed and tied my feet together and then pulled them against the leg
of the bed. When she was done, I was in a half sitting position with
my legs pulled to the side. She checked to make sure that her knots
were tight and then left the room.
I sat there for quite a while contemplating my fate. I struggled with
the bindings but had no success if getting free. I was hot, sweaty and
worn out when I finally heard the door open. Melissa walked back into
the room but this time she had a companion. It was the bartender that
had been out front when I had first arrived. He was tall and thin with
an obvious gay look to him. He smiled and giggled as Melissa pulled
him over to the bed.
"Take a look Phillip. Other than your own little sissy boy, have you
ever seen such a pathetic excuse for a man? Now, I want you to have
this little sissy service you as a man. And if he doesn't do good
enough, I will have to go out on the street and find another man for
him."
She pushed Phillip towards me and laughed as she again walked out of
the room. Phillip just stood there looking at me as if he didn't know
what to do. I tried to plead with him but the panties stuffed into my
mouth cut my pleas to mumbles. Slowly, he made his way closer to me
and when he was only a few steps away, he reached down and unzipped
his pants. Before he moved any closer he reached into his pocket and
pulled out a knife. He opened it, and set it down on the end of the
bed. "Just a little precaution, incase you decide to bite! Now when I
take those panties out of your mouth, I expect you to be quiet. Then,
I expect you to act like a lady, and give me the best blowjob you can.
Do I make myself clear?'
I nodded my agreement. I had no choice in the matter. I now was not
only in fear of what Stephanie would do to me; I was also in fear for
my life.
Phillip picked up the knife and used the tip of it to pluck the
panties from my mouth. I gasped for breath as he did. When I looked
up, he was still holding the knife, and now he was pushing his semi-
erect penis towards my face. "Open up sweetie. This is what you have
been waiting for."
I opened my mouth wide enough for him to gain access but not full
wide. He used his free hand to grab the back of my head and then he
thrust forward with his hips. I gagged and choked, but he held my head
firmly in place. Soon, he was pumping in and out, each time trying
harder to penetrate my throat. It didn't take long when suddenly he
pulled hard and thrust deep and held me tight. He pumped stream after
stream into my mouth and down my throat.
When he was done, he pulled away and smiled at me. He used the knife
to cut my bindings and threw my panties to me, "Now get dressed and
get out before Mel gets back. I will let you out the back door. I can
handle her, but if you are still here when she gets back, you may not
survive the night. She probably has twenty guys lining up right now
who are all ready to abuse you."
I wasted no time getting my torn panties on, my skirt and top
straightened and my hair and makeup fixed enough to make me look like
I had not been in bed with half the population of the city. True to
his word, Phillip let me out through the back door. I hurried down the
alley and around the corner.
I walked down the street to the bar where Stephanie had given me
orders to meet her. It was a small dimly lit club with quiet jazz
playing, and very few customers. I looked around and didn't see
Stephanie anywhere so I made my way to the bar to wait for her.
When the bar tender came around, he already had a glass of white wine
ready. He sat it in front of me and gave me a smile, "You must be
Tiffany. A lady stopped by earlier and said that you would be in." He
slid me a note and laid a ten-dollar bill on the bar. "She said that I
should give you this."
I picked up the note and opened it as I took a drink of the wine.
"Tiffany, I can assume that you were successful in achieving your goal
since you are reading this note. Actually, there is no way that you
could have failed, is there? It was only a matter of how long it would
take you to succeed. I have provided you with enough money to pay for
your drink and to get you home. Now I know that the $10 won't get you
a cab, especially after paying for your drink, but it will cover bus
fair. The bus stop is three blocks north. You can take the 27 bus to
the station stop and then transfer to the 54 bus out to its turn
around at Park Lane Mall. From there, it is only about ten blocks to
my apartment. See you when you get there. Love Steph."
I waved down the bartender and paid for the wine. I confirmed the
location of the bus stop and he gave me a quick warning as I was
headed out the door, "I'd hurry if I were you. The bus will be there
in about ten minutes, and this will be the last run for the night."
I wiggled my way the length of three city blocks as fast as I could in
the tight skirt and high heels. I got there with only a minute to
spare. When I got on the bus, the driver took the fare and leaned
towards me saying, "I'd sit right here in the front Miss. There's a
couple of three boys in the back that look like they could give you
trouble if they had a mind to."
The bus ride was about twenty minutes and the boys hooted and whistled
and made obscene comments the whole time. When I got off at the
station, they were right behind me, but they turned towards the lobby
while I sought out my transfer. The second ride was longer, almost
forty minutes, but there was only one old lady on the bus for most of
the ride. A couple others got on and off at various stops but they
never seemed to take notice of me.
The worst part of the trip back to Stephanie's was the ten-block walk.
By now, my feet were tired beyond belief, but I never thought to take
off the shoes. I had to walk through this upper middle class
neighborhood looking like a cheap hooker. I thought for sure that a
cop would show up at any minute, but it did not happen. It was almost
2:30 when I walked into the apartment. There was a note on the door.
"Tiffany, DO NOT wake me up. Clean up and go to bed. I will be
expecting a full report in the morning over breakfast. I will be also
be expecting breakfast in bed at 8:00. Steph."
The next week went by without too much of a problem with Stephanie. It
was a good thing, because I had my hands full with the sexual
harassment investigation. I had been removed from all casework and
told to make myself available to Mrs. Karnow at all times. She would
be handling the investigation and I should cooperate fully. I spent
most of my time answering long convoluted questions about my time at
the firm and female attorneys that I had worked with or around. It
seemed as if the entire case was based on circumstantial evidence, and
complaints that alleged encounters that never took place. I was being
set up, and I knew it.
On Thursday, Stephanie stopped by the HR office and asked if I would
join her for shopping and dinner. I of course had no alternative but
to say yes. As it turned out, it was an enjoyable evening. The dinner
was good, and the shopping was interesting. Stephanie was looking for
a dress to wear to a party this weekend. She wanted it to be elegant
and sexy. We worked our way through every store at the mall before she
found the perfect dress.
The dress that Stephanie finally selected was breath taking. The skirt
was black satin and fit tight at the waist then flared out to the hem
that came only to mid thigh. It required the use of a stiff lace
petticoat to properly hold it in place. The bodice of the dress was
velvet and cut with a daring neckline. There were puffy sleeves that
covered just the shoulders and ended in a tight cuff high on the arm.
The front of the dress was patterned with swirls of gold glitter that
matched the gold trim woven into the black lace of the petticoat. We
left the store with Stephanie telling the clerk that the dress would
be picked up Saturday afternoon. I felt bad that I would not see her
in the dress. Saturday was my birthday, and I would be having dinner
with Barbara.
Friday after work, I was looking forward to an evening to relax prior
to Barbara's return. My nerves were shot from a weeks worth of
answering questions for Mrs. Karnow and I could use the time to
myself. I was walking to my car when I saw Stephanie enter the parking
garage. She came along side of me and smiled as she brushed her hand
against my crotch. "Got any plans for the night?"
I tried to explain to her that I planned to spend the whole evening
doing nothing at all, but she wasn't listening to me. She just kept
right on talking, and finally I heard her say, "Well I am glad that
you didn't have plans that we would have to break, because, ‘Tiffany
is here,' and we have things to do."
With the words spoken, Tom was gone, and replaced by Tiffany. I was
bubbly and giggly and ready to do what ever Stephanie had planned for
me. Tom's car was left in the parking lot and we drove together in
Stephanie's car to a very nice hotel down near the lake. When we
walked into the lobby, Stephanie whispered into my ear. "I am going to
let Tom come back for just a minute so that he can pay for the room.
But I want you to warn him that he had better ‘behave' because if he
doesn't, I have picked out a truly evil ‘punishment' for him."
Tom was allowed to return for just a few minutes, just long enough to
offer up his credit card for the room. As soon as we were on the
elevator however, Tiffany was summoned again.
As soon as we were in the room, I was ordered to take off the ugly
men's clothing that I was wearing and given a much more suitable
outfit to wear. Prior to getting dressed however Stephanie decided
that there was a little matter that needed to be dealt with. She
handed a cup to me and told me to masturbate until I filled the cup as
much as I could. It took only a minute and I made sure to catch every
drop in the cup, but it was far from full. Stephanie took it from me
and put it in the refrigerator, "We will see if we can get more
later."
Dinner was in the Italian restaurant at the hotel. Over the meal,
Stephanie explained to me that tomorrow was Tom's birthday, and we
were going to give him a big surprise. I was thrilled; I knew that I
would love a birthday surprise so it was going to be great fun giving
one to Tom. The only problem was, I didn't quite remember who Tom was.
Back up stairs, it was time to try and fill the cup again. This time
Stephanie helped to get things going. It took some effort to get hard,
and there was less of a contribution to the cup. "I am sorry
Stephanie, I really tried but it just doesn't seem like I am doing a
very good job."
Stephanie took the cup back to the refrigerator, looking at how full
it was. "Don't worry. We will try several more times tonight, and I am
sure that by the time you are completely drained we will have enough
for our purposes. Maybe we will use some water to thin it out a bit."
For the rest of the evening, I was given very careful instructions on
how we would give Tom his surprise tomorrow. When Stephanie was sure
that I understood completely, she told me to change for bed and then
we would take one more collection for the cup. With the collection
completed, I watched as Stephanie took the cup and set it on the
table. She then took a piece of ribbon that had a small key tied to it
and carefully lowered the key into the cup while allowing the ribbon
to hang over the edge. She then took the cup and put it into the
freezer. I then headed to the bed where I was tucked in for the night.
The alarm went off at 8:30 and I awoke to find myself, Tom, in the
hotel room that I remembered paying for last night. I tried to roll
over and found that I could not move. I was bound securely to the bed
and wearing a pink baby doll nightgown. I took a careful look around
the room and determined that I was alone, and that who ever had bound
me had done a very good job. I supposed that it was Stephanie, but I
had no recollection of her having been here last night. In my hands
was a note and I struggled to get it into a position where I could
read it. My hands were in handcuffs that were attached to a rope that
was wrapped around my waist. I could move just enough to get the note
in my line of sight, but there was something else there also. What
ever it was hanging there, it was only an inch above my mouth and was
hanging from a ribbon that was stuck to the ceiling. It was frozen and
it dripped on my chin as it melted. I would worry about that in a
minute, first I needed to see what the note said,
The note was from Stephanie, and it outlined my situation and my
choices. "Tom. I want you to know that this is the last time that I
will ever call you by this name. You will find that you are quite
soundly secured to the bed, and that there is no immediate way for you
to free yourself. However, I have left you with two choices. The small
frozen treat that hangs in front of you contains the key for the
handcuffs. It is your choice how you retrieve it. You can allow it to
melt, which I estimate, will take about two hours, or you can use your
tongue to reach out and lick it. This will take far less time.
If you choose the first method, you should know that I have arranged
for the maid service to make up the room in about 30 minutes. Based on
your current position and what you are wearing, this might be quite a
problem for you. If you do choose this method, you will certainly
suffer through the embarrassment of discovery, and your story will
probably make the front page of the paper. I have however, arranged
for your entire memory of this event and all of those that we have
shared to be erased. You will simply go back to what you were before,
a transvestite wearing your wife's clothing, except that she and
anyone else that reads the paper will know all about it."
So far, choice one didn't sound so good. I could never let myself be
found out. I liked my life just as it was, with the exception of
Stephanie's control of me, and I wasn't ready to give it up.
"If you think that you prefer choice number two, I think that you
should know what it involves. You will be able to free yourself in
time to call the desk and delay the room service; this will allow you
to escape the discovery and embarrassment. If you choose this
direction, you will have to pay a penalty. When you are free, you will
get dressed and prepare yourself for a full day of activity as
Tiffany. You will still be conscious of everything going on, but will
have no control over the outcome. Tiffany will guide you through a day
in her life, and you will be released in time to enjoy dinner with
your beloved wife. I must warn you, if you do choose this path, I will
forever more call you Tiffany."
I was stuck. Were these my only two choices? I didn't have long to
think about it. If I took the first choice, my life would be ruined. I
could not let this happen. It would have to be the second choice. I
would get myself free, and then I would find a way to avoid the
Tiffany routine. Surely, I could think of something.
With my decision made, there was no time to waste. I stuck out my
tongue and licked the frozen ball that hovered over me. In that
moment, I realized that I had made a terrible mistake. The first taste
from the frozen object that held the key let me know exactly what it
was, and I suddenly remembered where it had come from. I tried to
stop, but with that first lick, Tiffany took over. She was ready for
this. She had me licking with a passion and within a few minutes the
key fell free of the frozen lump and swayed on the ribbon to within an
inch of my hands. I had to arch my back and push up with my shoulders,
but I was soon able to grab the key.
With the key in hand, I was quickly able to extricate myself from the
bondage. By the time on the clock, I had only a few minutes to call
and cancel the maid service. With this done, I went to work on getting
dressed. It was as if I were a spectator to the event. Although I knew
what was going on, I had no control over it. I showered and dressed
quickly. There was only one outfit available and I put it on. There
was bra, panties, panty hose and a half-slip. There was a brown suede
skirt, a brown and tan striped sweater and a pair of brown pumps with
three-inch heels. I fixed the brown wig to my head put on some make
up, grabbed my purse and headed out the door.
I took a taxi to the area out near the mall where Stephanie and I had
shopped two nights before. The address that I gave the driver turned
out to be a day spa. When I went in and registered, the young girl at
the counter said that they knew all about me and were ready with my
first appointment. I started out with a full body waxing. Every trace
of hair was removed with the exception of a small patch of pubic hair
and the hair on my head. They even used the wax to shape my eyebrows.
The next treatment after the waxing was a body dip in hot oil. I lay
on a small table covered with soft straps. The straps were gathered
and hooked to a hoist overhead, which was used to lift me. I was
raised up and slid across the room over a large tub of hot oil. The
hoist was lowered and I was submerged in the oil. The girl operating
the controls had warned me to take a deep breath and keep my eyes
closed. The oil was very warm and felt like it was penetrating every
pore in my skin. After a minute or more, I was lifted out. I was
almost out of breath and gasping when I cleared the oil. The process
was repeated three times before I was through. I was removed from the
straps and led to a shower to wash off the remnants of the oils from
my body.
The final body treatment was a rub down with a heavy cream containing
aloe and eucalyptus. A total stud named Mark administered it.
Throughout the entire process, he told me how his boyfriend Davie
loved this treatment.
The next stop was for a manicure and pedicure. My toenails were
trimmed and buffed. On my hands, my nails were trimmed and the
cuticles pushed back. The girl then applied a set of acrylic nails
trimming and filing them to a long rounded taper perhaps an inch past
the tips of my fingers. She buffed them and left them a natural color.
I paid my bill and left the spa headed for the mall. I headed towards
one of the popular lingerie shops but was distracted on the way by a
sign in front of a jewelry shop advertising free ear piercing. I had
my ears pierced and a pair of gold hoops put in. The girl that pierced
my ears advised against it until they were healed, but I insisted. I
noticed that she had her ears double pierced and decided to have mine
done also. In the second piercing I heeded her advice and bought a set
of diamond studs. Before I got out of the chair, I decided to have my
right ear pierced in the top cartilage. In this new hole, I had her
insert a small hoop with my birthstone dangling from it. Before I left
the store, I also purchased a gold necklace, bracelet, and ankle
bracelet, along with three rings. By the time I was done, I had
amassed a huge bill. I paid with my credit card, smiled at the girl
and head back into the mall.
Once at the lingerie store, I knew exactly what I was looking for. As
I was selecting the set, one of the sales girls came over to help. I
had already picked out the set and was just looking around. My choice
was all in black satin and lace. There were panties, garter belt and
bra and a pair of real silk stockings. She looked at the set and
stopped with the bra. "Are you quite sure that you have the correct
size? This is a 36D bra, and the cups might be a little large for
you."
I stopped where I was and knew exactly what my answer was. "Actually,
I have always wanted bigger boobs, and was hoping that you had
something here to help me fill this out." I said indicating the bra.
The girls smiled and said, "Don't we all wish for more. But I think
that we have what you need." She led me to the back of the store and
showed me several types of artificial breast forms. She helped me to
select a pair saying, "These work best and look more natural when
applied with adhesive. I could show you how to do that if you like?"
When I left the lingerie store, I was wearing my new bra and panties.
I needed the support of the bra to hold up my new bust line. Even with
the adhesive, they needed substantial support. As I walked through the
mall, my new boobs bounced and swayed and I got more looks from men
than I had ever noticed before.
My next stop was a shoe store where I picked out a pair of black
velvet multi strap sandals with five inch gold heels. They were a real
bitch to walk in, but I fell in love with them the moment I saw them.
With most of my shopping complete, I headed to a beauty salon at the
far end of the mall. I had already made an appointment although I
could not remember doing so. They were ready for me and already knew
what to do. First, my hair was washed and dried with a towel. While my
hair was still damp, a long brown wig was fit over the top of it. The
girl used what looked like a crocheting needle to reach through the
cap of the wig and pull my hair through. She then tied little knots
with the strands of my hair to affix the wig tightly. It could not be
removed with out untying each knot, or pulling out my hair. When this
was done, she washed the wig together with my hair, applying a
coloring to it. She explained that she was bringing it to a lighter
shade of brown. When she had achieved this, she would be applying
blonde highlights and then cutting it in to a long full shag. The
style would feather and flow and be very feminine.
While my hair was being finished, another girl started on my nails.
Since they had already been lengthened, she only had to apply the
bright red polish that she helped me select. With my hair and nails
done, it was now time for makeup. The girl that worked on me did a
wonderful job. The makeup was very elegant and unbelievably sexy. When
I looked in the mirror, the combination of my hair and makeup was
almost overwhelming. I thanked all of the girls for their efforts paid
my bill and was back in the mall.
My last stop was the dress shop where I had helped Stephanie select a
dress the other night. Now I realized we had selected it for me, not
for her. The sales clerk remembered me and brought out the dress as
soon as she saw me. "Would you like to try it on dear?" I nodded my
head and we headed for the dressing room.
I decided that for the full effect, I should put on the remainder of
my new lingerie, and the new shoes. The sales clerk agreed completely.
She asked if I would need any help and I told her no as I headed into
the dressing room.
Once I got to the dressing room, I realized that I was going to have
problems. Putting on the garter belt and stockings with my new nails
was going to be difficult. It took me nearly twenty minutes just to
accomplish this much. Every few minutes the sales clerk would check up
on me and I would tell her I was fine. Finally I stepped into the
dress and pulled it up into place. When I tried to zip it, I found
that the combination of my nails, the fit of the dress, and my new
boobs would not allow me to zip it. I went ahead and slipped my feet
into the shoes and stepped out to look at the dress in the mirror. As
I did, the sales lady was right there to zip me up.
When I looked into the mirror, I knew that I could not take it off. "I
think that I will just leave it on. The party is in a few hours so why
bother to change?" I put on the remainder of my jewelry and felt a
thrill run through my body. I left the store with my old clothes in a
shopping bag.
I still had a few hours to kill, so I wandered the mall a bit longer.
I bought a new purse that matched my dress, and a bottle of perfume.
It was called ‘Seduction' and I just had to have it. The sales girl at
the countered sprayed me with a heavy dose before I dropped the bottle
in my purse.
I found a small teashop in the mall and sat there to relax for a few
minutes. I took a few things that I needed out of my old purse and put
them into the new one that I had bought. When I looked at the credit
card before dropping it in, I read the name, Thomas William Mears. So
this was Tom's card? I wonder if he was enjoying his birthday
surprise. I was certainly enjoying it. With out giving it further
thought, I finished my tea and headed to the mall entrance. It was
getting late and I needed to get a cab to take me to the restaurant. I
remembered Tom was meeting his wife there.
When I walked into the restaurant, I was aware of how wrong that this
was, but I could do nothing about it. I was supposed to be free to
have dinner with Barbara, and I needed to change clothes but Tiffany
would not let go. "My orders were to get you to the restaurant for
dinner with your wife. I am not supposed to let go, until you are with
her."
Terror ran through me. Tiffany would lead me right up to Barbara's
table and then turn me loose. Now I understood the ‘penalty' that
Stephanie had mentioned. I was in a lose, lose situation all along.
However, this way I had the whole day to prepare for the outcome with
out realizing that I had no choice.
I walked up to the maitre' de and smile at him. "The Mears table
please."
He smiled back politely, but his glanced dropped to my bust line.
"This way please, I believe that you are in the Crystal Room."
It didn't register until we were at the door. Why were we seated in
the small party room? This room probably seated fifty people. This was
supposed to be an intimate dinner. But I never had time to consider
the answer further. He opened the door and backed away as I walked
into the room. It was dim, almost dark with the lights turned down. I
turned to see what was going on only to see him closing the doors and
the room becoming darker. Just when it made no sense at all, the
lights all came on.
"Surprise!!! Happy Birthday!"
I turned and looked into the room and I don't know who was more
surprised, me, or the 50 people cheering from behind their tables.
Suddenly, Tiffany was gone, and Tom was on his own. I now fully
realized the depths to which Stephanie had gone to set me up. There
was Barbara standing in the middle of the room looking at me and not
recognizing me. There beside her were her parents, my parents, brother
and sisters with their spouses, friends, and neighbors. Off to one
side, stood Stephanie looking very beautiful and smiling brightly. I
fought to maintain control, but I lost. There was no way out.
As I stood there, I muttered, I thought, to myself, "Oh my God! What
am I going to do now?" But apparently it was loud enough for Barbara
to hear me and recognize my voice. Her face turned white.
"Tom? Is that really you?"
The room went silent.
I tried to talk to her but she would not listen. When I moved towards
her, she pulled away. Her parents shielded her as the crowd left the
room. The only member of the family to come to me was my sister Beth.
She hugged me and told me I was beautiful, and that I could call her
if I needed to talk.
Soon the room was empty. My parents had left without a word. Near the
end, I saw Stephanie sneak out the side door. As I caught her eye she
smiled and then winked. She knew exactly how much trouble I was in,
and she loved every minute of it.
I headed home trying to decide what to do next. When I arrived there,
Barbara was there with her parents. We did not talk. I gathered a few
things including clothes and put them into my car. I tried once more
to talk to her but she would not. She had her father tell me that she
never wanted to see me again.
I stayed in a small motel the next two nights trying to come to grips
with what had happened. I tried to call Barbara but got no answer. I
drove past the house and her car was not there. I went in and gathered
up a few more things, then headed back to the motel. I tried
repeatedly to get in touch with Stephanie but got only her answering
machine. I went to her apartment and found that the lock had been
changed. I had no idea of where she had gone to, but it appeared that
she wanted nothing to do with me.
On Saturday afternoon I managed to find a beauty salon open where I
could have the wig removed. By the time that they were done I ended up
with little more than a brush cut. I would take some time for it to
grow out into even a decent looking men's hairstyle.
On Monday morning I drove to the office needing at least one aspect of
my life to hold onto. When I got to the parking garage, I got my first
taste of how my day would go. My parking pass was not accepted. I slid
it into the card reader and it did not come back out. A message on the
screen read, "Parking Privileges Revoked." I backed out of the line
and drove down the street to a surface lot. I paid the eight dollars
for the day and walked back to the office. Entering through the lobby,
I slid my security card into the scanner and pulled on the door. It
didn't open. I waited until another building resident came in, and
snuck in when they opened the door.
I was waiting for the elevator when a Security Guard approached me.
"Mr. Mears? Would you please come with me?"
He led me to a small office off the side of the lobby. There sitting
at a small conference table was Mrs. Karnow.
She didn't even wait for me to sit down. "In light of the
investigation, and the evidence that has already been compiled, you
are in a very tough position. Now, we hear rumors of another rather
unsavory aspect of your personality, and it is impossible to tolerate
any further risk. I took the liberty of having your office cleaned
out. You will find your personal effects in the box. You will be
receiving 8 weeks of severance and have the opportunity to continue
your health care for up to two years if you so choose. This will all
be called out in a letter that is being sent to you. Do you have any
questions? If not I believe that we are through."
She left the room with out saying another word.
I went back to the motel and checked out. No sense in staying there
when I had a perfectly good house to go to. By the time I arrived, it
was 11:00. What a day it had been already, but it was not over yet. At
the house, a County Sheriff met me. He handed me two documents. The
first was a notification of the filing for divorce. The second was a
restraining order, ordering me out of the house, and to stay at least
300 yards away from my wife at all times. Somehow her lawyer had
worked very fast. I was allowed one trip into the house to pick up the
rest of my clothes, and personal hygiene products. Everything else was
considered a shared asset of the marriage and was protected by the
court. I noticed that the key he had used to let me was different than
any that I had seen before. Apparently they had already changed the
locks. As I drove away from the house, the sheriff stood and watched.
I had no desire to go back, but he was taking no chances.
The divorce went quickly; I had no cause to protest. There is an old
adage that says divorce is a 50 / 50 split, she gets half, and the
lawyers get half. That was about the way this went also. She got the
house, which was almost paid for, and her car, which was paid for. She
also got half of all of our investments. For my part I got all of my
personal belongings, half of the investments, which would go mostly
towards paying the lawyers, my car, which was not paid for, and all of
the outstanding bills.
With little money, and no job, I didn't see much of a future for
myself. I sent out resumes and answered job postings on the Internet,
but nothing was forthcoming. I had found a room at a small boarding
house and was getting desperate. It was about this time that Stephanie
found me.
I was coming out of an office building downtown, having just completed
a go nowhere interview. I had taken the train into town and turned up
the street towards the elevated station when she pulled up along side
of the curb. "Hi gorgeous, can I give you a ride?"
I looked at her, and hated everything about her, but at the same time,
I loved her. Still, I was so mad that I just had to let her know how I
felt, whether it was standing here in the street or anywhere else. I
moved towards the passenger side window and started to vent my anger,
however my tirade was over before it began. I saw her look at me and
speak three words before I fell silent, "Tiffany is here."
I calmly got into the car with Stephanie and we drove off. We talked
about how long it had been since we had seen each other, and she told
me that she was looking forward to spending some time together. We
drove to the rooming house where Tom had been living and picked up a
few of his things. We told the landlord that he was moving out and
would arrange to have the rest of his things picked up. From there, we
drove across town to Stephanie's apartment.
When we were sitting in the apartment, Stephanie told me that she
wanted to help me get settled. Since I didn't have a place to stay, I
could use her spare bedroom for a while. She would also help me to
find a job and even go to school if I wanted. After we had talked for
a long time she looked at me and said, "We are starting down a long
road together, and I think that as a first step, you should take off
those ugly men's clothes and put on something sexy. Go look in your
closet; I saved all of the things that you had bought before, so you
still have a great wardrobe to work with.
In the bedroom, I looked around and found something to wear. Stephanie
had said sexy, so I selected a sheer black nightgown and panties to
match. I found a pair of slide on shoes with four-inch heels and
trimmed with marabou feathers. I sat at the dressing table and put on
a little makeup then added a spray of perfume. I didn't know what to
do with my hair. It was just a bunch of matted waves and curls. I
brushed it out and combed in a little mouse to help it stand up a bit.
It wasn't much, but it would do until it grew out some. I promised
myself that I would never cut my hair short again.
I rejoined Stephanie on the sofa in the living room and we talked for
several more hours. She kept telling me how much she loved me, and
that she would make sure that I became a perfect lady, no matter what
it would take. I didn't understand her because I knew that I was a
lady already, but if she wanted to help me get a job and maybe go back
to school, I wasn't going to argue. After a while I must have become
tired because I heard Stephanie say, "Tiffany needs a nap," and the
next thing I knew, it was morning and she was waking me up in my
bedroom.
For the next six months, Stephanie sent me to several schools. I
studied makeup and hair styling and was quickly becoming an expert. I
would wash and style Stephanie's hair as well as mine. When she
thought that I was good enough, she even invited Dr. Baxter over so
that I could do her hair. I must have done well, because Dr. Baxter
told me that she had a friend who was also a doctor and she would like
to bring her by to get her hair done. I thanked her and told her that
would be fine, anytime that she wanted to.
I met Dr. Mathews a few weeks later and styled her hair for her. I had
a lovely time. Her hair was very long and full. I washed it and
trimmed it and even added some highlights to it. She was very pleased
with the results and told me that if there was ever anything that she
could do for me, all I had to do was ask.
This is where Stephanie stepped in. "Tiffany, did you know that Dr.
Mathews is a plastic surgeon? She specializes in helping ladies that
could use a little help developing their figure. Now, didn't you tell
me just the other night that you wished that you had bigger breasts
and rounder hips? I'll bet that the doctor would be able to help you
if you would like."
That suggestion was all that it took. Two weeks later I was in the
hospital for surgery. Somehow, Stephanie had fixed it so that Tom's
insurance would cover the fee. She said that it was due to a car
accident and the surgery was medically necessary to prevent
disfigurement. After the surgery, they told me every thing that was
done. I was in bandages from head to toe, so I knew it must have been
a lot.
I learned from the doctor what she had done during a series of
surgeries over several days. First, she had used a lipo-suction
technique to remove some of the fat from around my waist. This fatty
tissue was then used to insert into my butt to help give me more
curves there. She had done breast implants to give me the boobs that I
had always wanted.
She told me later, "I thought that ‘D' cups might be a little too big
on your frame but you insisted. Now, I think that they look just fine.
I am glad that I pulled in the muscles a little tighter to give them
extra support, else they might start to sag."
The doctor had also done some work on my face. She had shaped my
cheekbones a bit to make them higher and a bit more pronounced. She
had softened my chin, and changed my nose so that it looked smaller
and turned up just a bit at the tip. As a final touch, she had
injected a drug directly into my vocal chords. This drug is normally
used on tendons and ligaments that have been stretched to the limit.
It shrinks the tissue cells and causes them to pull tighter. When used
on the vocal chords, it has the same affect, it causes the tissue to
shrink and pull tight. The result was that my voice was almost a full
octave higher and much softer.
My recovery time was almost six weeks. The bandages came off after
several days, but there was considerable swelling and bruising. When I
was finally able to look in a mirror and see the results, I couldn't
believe my eyes. I didn't recognize the face that looked back at me.
She was not just cute, she was gorgeous. While my facial features had
never been on the rugged side, all semblance of masculinity had been
removed.
During the time that it took for me to recover, Stephanie helped me to
resolve several issues. Since I was not working, there was no way to
afford the payments on my new BMW. She helped me to sell it back
through the dealer and to buy a car that I could afford. I ended up
with a three-year-old VW beetle. It had originally been painted red,
and someone had added detail painting to make it look like a giant
Ladybug. I was even able to get the vanity license plate that said,
‘LDY BUG'.
We were able to buy the car and have some money left over, so we went
on a shopping spree for new clothes. With my new breast size, I need
new bras, and of course panties to match. The same thing applied to
blouses and tops, because what I had would no longer fit.
The next difficulty that I faced was proof of identity. I don't know
why, but I did not have any form of ID. I could not find a driver's
license, social security card, or any other method of ID. Stephanie
suggested that I had probably lost my purse somewhere and that all of
my IDs would have been in it. It was a good thing that she was an
attorney, because she knew all of the things that needed to be done to
secure new copies. Over a several day period, she brought home papers
for me to sign and then made sure that they were all sent in to the
proper agencies.
All of Stephanie's hard work paid off, because after a few weeks, I
started receiving new copies of all of my information. I had a
driver's license, social security card, and, a copy of my birth
certificate. I also had copies of my high school diploma, and even a
college diploma that I didn't remember having. I had a degree in
Business Administration with a major in Legal and Secretarial. I had
apparently done well and graduated with a 3.85 GPA.
For the next six months, I tried and tried to find a job using my
education as a foundation for some exciting position, but I was unable
to land anything. In order to earn some money, I took a number of
different jobs just to get by. I worked as a waitress in an upscale
restaurant, a cocktail waitress in a large downtown nightclub, an even
took a try as a stripper in a gentleman's club. Stephanie had helped
me to find the jobs but one thing always lead to another and I would
be out of work again.
One day, Stephanie surprised me with a new suggestion for a job. She
would set up an interview for me at the law offices where she worked.
There were openings for various clerical and secretarial positions and
she was sure that I would have an excellent chance to get one.
My first interview was with Mrs. Karnow in the HR department.
Stephanie had told me that she was very stern and that not many people
liked her so I was not sure what to expect. The interview however went
well and she was going to set up an interview with one of the junior
partners who was looking for a legal clerk and secretary. She thought
that I made an excellent candidate for this position.
The next interview was with Martin Peterson, the young junior partner
that Mrs. Karnow had mentioned. I had dressed carefully for this
interview wanting to have the proper look for someone in a large legal
firm but at the same time wanting to be subtly sexy. Stephanie had
told me that Mr. Peterson was known to have an eye for the ladies and
she was sure that I could use this to my advantage. The outfit that I
wore was a grey pinstripe suit. The skirt was fitted and short, ending
at mid thigh. The blouse was grey silk with a high collar but it had a
keyhole cutout that helped to show some cleavage. The jacket was waist
length and fitted tightly. I wore grey stockings and pumps with four-
inch heels. My hair was done in a feathered bob and I had taken extra
time with my makeup. I selected simple gold jewelry and a small grey
purse. Stephanie was sure that the outfit was perfect, and told me the
job was in the bag. After all of the disappointments of the last six
months, I was not as confident.
The interview with Mr. Peterson went extremely well. He asked some
tough questions but I was able to handle them all. I seemed to be able
to pull up all kinds of legal knowledge and terminology that I must
have learned in school but did not remember until asked specific
questions. Mr. Peterson seemed very impressed. "There are attorneys
out there that have worked in practices for five years that don't have
the working knowledge of legal issues that you possess. I don't mind
telling you that I am quite impressed."
During the entire interview process, Martin Peterson the attorney
asked the tough questions, but Martin Peterson the man took his time
to make a close inspection of my body. His eyes would dwell on my
breasts, and then move slowly to my legs. When I would catch him
looking I would slowly cross them or uncross them and watch his
expression. He seemed as if he were in a trance. By the end of the
interview, I believe that he had a good idea of my professional
skills, and had some pretty good guesses about other skills that he
was sure that I possessed. I walked out of his office with the job
offer as well as an invitation for dinner. I had accepted the first
and kindly declined the second.
I started work at the law office on the following Monday. Stephanie
helped me choose an outfit to wear; making sure that it met the
minimum professional standards while keeping as much of my body on
display as possible. Over the next few weeks I heard a lot of comments
about how I had been selected for the job, but as time went by and I
proved myself to be capable and competent. I even heard comments that
my choice of style for the office had many of the other secretaries
and legal assistance making changes in their wardrobes.
It was three weeks later when Stephanie caused me to come to grips
with my situation. We were sitting in her apartment relaxing over a
bottle of wine after dinner. I had prepared the dinner, served
Stephanie, cleaned up and done the dishes, and finally set down to eat
my own dinner. This had become a normal part of our evening routine.
On this particular evening, Stephanie told me that she had something
special planned and she needed my help. She had me sit on her big wood
rocking chair while she tied me securely to it. My hands were tied to
the arms and my feet to the legs. She put a long scarf around my waist
to tie me there, and another around my neck so that I would keep my
head up. She asked me if I was ready and I nodded yes. As I sat there
patiently, I heard her say, "Tommy is back."
I came to my senses in an instant. I immediately tested the bonds that
held me to the chair and found them too tight to allow any possibility
of escape. My next reaction was to verbally express myself, but
Stephanie cut that short as well. Barely were the first words out of
my mouth when I heard her say, "It's time to be quite." Instantly, my
voice was gone. My mouth moved, but no sounds came out. In frustration
I gave in and sat there quietly.
Stephanie looked at me and smiled. At the same time, it was more there
than just a smile. "Well Mister Big Shot Attorney, how does it feel
now? You know, you could have had it all, your career, the money, and
me. All you had to do was divorce that wife of yours and we could have
gotten ourselves married. It would have been perfect. But no, that's
not how you saw it. You thought that you could just continue to play
your little games of dress up, and use me to fill your sexual needs,
didn't you? Well, things haven't turned out like you planned, have
they?"
I sat there listening and trying to figure out how to get loose. When
she looked at me, I tried to plead with my eyes, but that was getting
me nowhere. She continued her little tirade. "So, my pretty little
one, let me summarize for you. You were a successful attorney with an
income approaching $200,000. You had a $500,000 house, drove expensive
cars and went on exciting vacations. Now, you work as a legal
assistant and secretary and make almost $30,000 a year. You drive a
three-year-old VW and share an apartment with me, which by the way, is
going to have to change. It's time that you get a place of your own.
Of course it won't be as nice as this is, not on your salary, but I am
sure that we can find you something acceptable. As for vacations, if
you start saving up, you might be able to afford a weekend trip next
year. But, I saved the best for last. You used to have sexual
relationships with your wife, and with me, but that's where your
trouble began isn't it? Now, you only provide sexual relief for me
when I feel that I need it, and then it is only with your tongue,
seeing as how your little friend has become incapable after all of the
hormones that you have taken."
I felt tears well up in my eyes. I couldn't believe what she had done
to me. I looked across the room into a mirror that hung on the wall at
the image of me reflected there. This effort was not lost on
Stephanie. "Why are you crying princess? Have I upset you? Well let me
try and make up for doing that. As a reward for being such a good
girl, I have decided to allow you to have the pleasure of sex again.
However, in order to do that, we need to find you a boy friend. Now, I
am going to ask you a question, and after you think it over you may
answer me, but you will only be able to give me your answer, nothing
more. And it had better be an honest answer, do you understand?"
I took in everything that she had to say, and was scared to death. A
boy friend? Sex? I don't think that I can do it, but I am sure that
she will find a way to make it happen.
OK princess here is your question. Think it over carefully and give me
your answer. "Of all of the eligible males in the law offices, which
one would you most like to go on a date with?"
I tried not to think about it, but I couldn't help myself. Most of the
eligible males had made the rounds to meet Tiffany in the last few
weeks. Now I had to pick one. I rolled it around in my mind and made
my choice. When I gave my answer, my voice came out clearly, "Justin
McNeill." I had seen him only a few times, and he was not one of the
many that made the rounds to meet me. He had been introduced in a
meeting and other than taking obvious notice, he did not make himself
the fool that many others had just to come and meet the new girl that
had a habit of wearing very becoming outfits that stretched the limits
of appropriate office attire.
Stephanie was grinning from ear to ear. "My, my. Aren't we a little
gold digger? Every single girl in the office has her eye on him.
Already a junior partner, earning a ton of money, and drop dead good
looking. Well, I can't promise, but I did hear him ask about you the
other day. We will have to see how interested he is. You know, this
could be your way back to a life of luxury if you play your cards
right."
My eyes had teared up again as I resigned myself to the fact that I
would probably be dating soon. I needed to find a way out of this
mess, but it didn't look as if I would.
"Well we'll work on the dating, and we'll have to see how we can best
lay a trail for Justin to follow. But we also have one other little
detail to deal with. If you are eventually going to have sex with one
or more of the guys from the office, maybe even Justin, we are going
to have to provide you with the proper equipment. I have already
talked to Dr. Mathews, and she doesn't think that it will be any
problem at all. You already meet all of the requirements for the
surgery. You only need to be able to be out of the office for a few
weeks. I think that you qualify for medical leave after six months, so
we have adequate time to plan."
I almost fainted. Was she talking about what I thought she was? I am
sure that I heard her right, and I was more afraid then ever. I
started to struggle with the bonds that held me to the chair.
Stephanie took quick notice and spoke only one word, "Freeze." That
did the trick. I sat there still unable to move. Stephanie took a step
closer and looked me right in the eyes, "I don't know why you are so
upset? I have given you everything you wanted. You wanted to dress
like a woman, pass as a woman and be treated like a woman. Now I've
given it all to you. So think about it, it's the same old story, be
careful what it is that you ask for, because you just might get it!
Now I want you to relax, because the next time that we talk, you will
be a whole new person. But for now, Tiffany is here."
Just that quickly, Tiffany was back. Tom had been put back to where
ever it was that he went and had been replaced by the ever-happy
Tiffany. Stephanie and I talked for several hours about all that was
going to happen. She let me loose from the chair and we searched the
want ads for apartment listings. We talked about dating, and all of
the guys in the office. It seems as if Stephanie even had her eye on
one of them. David Reid and she had been dating for quite some time
and now they were getting serious. Stephanie told me that she needed
to make sure that I could take care of myself before she let their
relationship go any further.
Over the next six months, things happened quickly for me. I moved into
my own apartment and was living on my own. It was a small place in a
quite section of a suburb northwest of the city. On most days I took
the train into town to save money. Gas and parking prices were a
burden that I could avoid. There were so many bills to pay that I
hardly had any money left at the end of each week. I always managed to
put a little away, and I quickly learned how to budget myself.
I started dating just a week after Stephanie and I had our talk. Over
the months, I went out with several of the guys from the office but
never more than once or twice. I had met a few other guys from around
the town where I lived and had dated one or two of them. Stephanie
congratulated me on being able to attract so many good-looking men.
Finally after several other dates, it happened. Justin McNeill asked
me out. It happened almost by pure chance. We were sitting talking
after a meeting, and he mentioned that a client had given him a pair
of tickets to the ballet. He said that he had never been to the ballet
before, but was always open to a new experience. He looked up at me
and simply asked, "What about you Tiffany, have you ever been to the
ballet?" When I shook my head no, he continued, "Well then, I think
that it's about time that we both gain a little sophistication in our
lives. Will you do me the honor this Friday evening?"
I almost fell out of my chair. I had to fight to maintain my
composure. I looked at him with surprise written all over my face. I
mustered up all of the courage that I had and answered, "Why thank you
for asking. I believe that the honor will be all mine."
The date turned out to be not only the ballet, but also dinner.
Stephanie told me that it would certainly be formal attire, and helped
me choose a dress. It was Royal Blue and made of a sequined material.
It hugged every curve of my body. I took extra time with my hair and
makeup to achieve a special evening look. I was surprised when
Stephanie offered to loan me jewelry for the evening. There were
earrings, necklace and bracelet all with real diamonds. She also
supplied a couple of rings.
The date turned out wonderful. Justin was truly a gentleman. He
dressed in a grey suit that was cut to fit his body. It showed off his
athletic physique. We dined at a quaint European restaurant right on
the lake and then headed to the ballet. The music and the dance were
both splendid. After the ballet was finished we found a small
nightclub where we could have a drink. We talked a little but not a
lot, there seemed to be communication happening at some unspoken
level. It was after 2:00 AM when he dropped me off at my apartment. We
stood at the door for a moment and then he leaned towards me and we
kissed. It was a tentative kiss at first, but it grew into something
more. We parted briefly, and then kissed again. This time there was
passion. When finally we parted we held on to each other for another
minute. Justin smiled and told me thanks for the evening. He waited
until I unlocked the door and was safely inside, and then he was gone.
It was Thursday afternoon, a week after the date with Justin, when I
became ill at the office. I had shared a lunch with Stephanie and
before we were done I started having stomach cramps and abdominal
pains. It got so bad, that I was taken to the hospital in an
ambulance. Later, I was surprised to find out that I was not at one of
the many local hospitals, but a private facility in the western
suburbs. I was met there by Dr. Baxter and then later seen by Dr.
Mathews. Stephanie stopped by to see me, and assured me that
everything would be just fine, she would see to that.
So it was that I woke up two days later needing to recover from
surgery. I didn't initially realize what had been done, but later
found out that Stephanie had held true to her promise of making me a
total woman. When I had sufficiently recovered enough to be awake and
alert, the doctors came in and explained it all to me in great detail.
I was given booklets to read that covered everything from the healing
process, to hygiene, and an exercise program to follow to assure that
my latest features would perform and respond satisfactorily, both for
me, and for any lover that I was to have. The doctors assured me that
once I was totally healed, about four months, I would be able to
experience sex in more new ways than I had imagined, and that I would
be fully capable of achieving orgasms that would take my breath away.
All in all, it sounded wonderful to me.
Stephanie was there to visit me every day. I received several
arrangements of flowers from the office and from many of the guys that
I had dated. Officially, they had all been told that I had suffered a
ruptured appendix and that it had required extensive surgery to make
repairs. I would be off work for another two weeks and then I would be
able to go back as long as I didn't push it too much. Sitting, typing,
walking and phone work were OK, but nothing more strenuous until the
doctor released me.
I worked very hard on the exercises that the doctors had given me to
help in my recovery. There was a set of ‘Vaginal Dilation Probes' that
we really nothing more than various sized dildos that were part of the
exercise process. Starting with the smallest of them I would carefully
insert it and then hold it in place. I would then go through a series
of squeezing, stretching and holding exercises. When I was through
with the first size, I would move up one size. Each time I did the
exercise I was to start with the smallest and keep trying to move up
in size. The goal was to be able to handle the largest of the six
sizes within three weeks.
Over the weeks of doing my exercises, I began to notice a whole new
set of feelings coming over me. The doctors had said that it would
take a while for all of the feeling to come back and for my body to
realize what was happening and now it was happening. I was doing my
exercises one evening when I just seemed to loose myself in the rhythm
of the movements. Before I knew what was happening, I was in the
throws of a monumental orgasm. I had never before experienced anything
so intense, but I knew for sure that I wanted more.
The next day at work, I explained what had happened to Stephanie and
she smiled, "Welcome to the world of female sexual fulfillment. I'll
bet that you can't wait for the next time can you? Well, I'll stop by
tonight with a little present for you, and we will see how good it
gets."
For the remainder of the day, I looked forward to whatever it was that
Stephanie was bringing as a present. If it made me feel half as good
as I did when I had the orgasm, it would be worth it. When I got home,
I quickly changed into a sexy negligee and waited for Stephanie's
arrival. I did not have to wait long until she showed up, looking as
if she were as anxious as I was.
When Stephanie came in, she quickly took charge. She had me fix her a
drink while she got changed. I had the drink ready when she walked
into the living room. She was wearing a black bustier, fishnet
stockings and six-inch heels. She extended her hand to take the glass
while making her intentions clear. "Well my little slave girl, you
look lovely tonight. I hope that you are in the mood for a night of
intense pleasure. Now I know that you don't want to disappoint me so
no matter what we do, I am sure that you will behave."
Well there it was, now I had no choice but to accept my fate. The
programming was still in place and the control word had assured my
compliance.
"Slave Tiffany, I wish to enjoy my drink while I consider your fate
further. While I sit here, why don't you use that wonderful tongue of
yours to make me feel good? If I were you, I would put extra effort
into it because the better you make me feel, the more lenient I am
likely to be on you."
Stephanie sat and drank her cocktail while I got on my knees in front
of her. I worked as hard as I could to bring her to an orgasm quickly
but she was not to be satisfied that easily. She used every bit of her
restraint to hold back as long as she could. After she finally let
herself go, she had a deep and prolonged orgasm all the while grinding
herself harder against my face. When she finally let up, she sighed
and looked at me, "Go get yourself cleaned up and fix your makeup,
then come see me in the bedroom."
When I got to the bedroom, I knew that I was in real trouble.
Stephanie had brought a large overnight bag with her and she was busy
unpacking it. I could identify several types of plugs, probes and
vibrators, as well as several different restraints. I stopped in my
tracks and gasped when I saw the array of toys she was laying out. She
turned when she heard me, "Oh, there you are. All prettied up and
ready to start. Come over here by the bed and let's begin."
As I stood there, she started to place a set of padded cuffs on my
wrists. I made the mistake of opening my mouth to complain and she
slapped me soundly. She finished putting the cuffs in place and
clipped them together. "Now since you choose to protest, we will have
to put something in place to control your mouth." She grabbed a penis
shaped gag and forced it into my mouth fastening it with a strap
around my head. While I was trying to adjust it in my mouth she
attached a small squeeze ball and started pumping. The gag increased
in size as she pumped in air. Soon it had my cheeks bulging and was
pushing at the back of my throat. When I started to gag, she told me,
"Relax, there is a small tube in the gag that will allow you to
breathe as long as you don't hyperventilate. I am going to pump you up
a little more and allow it into your throat, it will be a lot easier
for you to learn how to do it with this toy than with a real penis."
When Stephanie was done pumping me up, I could feel the gag well down
into my throat. It took a great deal of effort not to fight it and to
relax so that I could breathe. When I relaxed, Stephanie laid me back
on the bed and continued with the restraints. My hands were pulled
over my head and attached to the headboard. She then placed cuffs on
my ankles and used two lengths of rope to tie on to the cuffs and then
pull them up to the corners of the headboard. As she pulled the ropes,
my legs were pulled up and apart until she had my backside elevated
and open to her probing hands.
While I lay there, Stephanie busied herself setting up her enema
system. She quickly had inserted a nozzle and started to fill me up
with a clear liquid, "Just a little soapy water to help clean you
out." While the bottle drained, she found a small pair of nipple
clamps and attached them. She then pulled out a long thin vibrator and
started attending to my vagina. She slid it in a little at a time
moving it out and around before reinserting it. When it was buried to
the hilt she flipped the switch and turned it on. When the vibrations
hit me, I almost went into orbit. My body jumped and twitched and I
bucked and pulled against my bonds. She left the vibrator work its
magic just long enough to make me really want it, and she shut it off
and removed it, cheating me out of the on coming orgasm.
Stephanie sat on the bed next to me and smiled, "Can't let you enjoy
too much, too fast. Besides, you're bottle is empty, time to clean you
out." She produced a plastic bedpan, and lifted my butt to slide it
under me. When she pulled out the nozzle I felt to fluid rush out of
me. When I was empty, she removed the pan and cleaned me off. She took
the bedpan into the bathroom to dump it and returned in a few minutes.
When she came back, I was not happy to see her. She was carrying a
large enema bottle filled with thick pink fluid that I recognized all
too well. I was in no position to resist, so I watched as she inserted
the nozzle and hung the bag. "This is going to be fun. I mixed an
extra large batch and made it extra strong. I used a large nozzle, but
it will still take a long time to fill you up. Making it extra strong
not only makes it thicker, it makes the itching worse and tends to
numb your nerve endings even more. With this mix, it might take all
night for you to have an orgasm, if you manage to have one at all. You
might just lay here in a mind numbing stupor praying for relief that
never comes. We will see. If you continue to be a good little girl, I
will make sure that you get your reward."
It took a short while for the pink fluid to start to enter me, but as
soon as it did, the itching started. I could feel it slowly but surely
build. All the while, Stephanie sat and watched; the amusement obvious
on her face. When I started to wiggle and struggle at the bonds she
let out a little laugh, "Looks like we're ready for the next phase."
Stephanie left the room for a few minutes and when she returned she
had another of her toys in her hands. This particular toy was a very
realistic model of an erect penis. When Stephanie got closer I could
see that this toy had a few special features. First of all, it was
hollow and clear, which let me see that it was filled with more of the
pink fluid. Secondly, there was a squeezable ball attached to the base
of the penis, which could be used to pump the fluid out of a small
hole in the head of the penis. When she started to probe my vagina
with the tip of the penis I about went crazy. I knew what the pink
fluid would do and I didn't want it filling my vagina. The more that I
struggled, the more Stephanie enjoyed it.
Little by little, Stephanie inserted the molded penis into me. By the
time it was fully inserted, I could hardly stand it. My whole backside
itched and kept me wiggling and the more I wiggled, the more the
invader filled my front side and felt better and better. I was about
to totally lose control when Stephanie grabbed the squeeze ball and
started pumping me full of the terrible pink fluid. On first contact,
the itching began deep inside of me and built until I was on fire.
Stephanie left me laying there in my misery while she again left the
room. This time when she returned she held a large glass of water.
When she came over to the bed, she held the glass in front of me, "You
look like you need a drink. Would you like some water?"
I nodded my head, the only action that I could make. In the back of my
mind I thought that she would have to remove the gag from my mouth,
but I should have known better. Stephanie held the glass of water and
said, "I want you to breathe through your nose. Take several breaths
and then stop and hold your breath." I did as she instructed and when
I held my breath she poured some of the water into the opening in the
gag. "Now I want you to swallow. Suck in and swallow the water."
I sucked on the penis gag and the water flooded into my throat. It was
cool and wet and wonderful. We repeated the process several times and
pretty soon I had emptied the entire glass. Stephanie smiled again,
"You did really well. That was and entire quart of water. Oh, by the
way, I forgot to mention that I added a strong diuretic to the water,
so don't be surprised if pretty soon you need to pee real bad. But I
just don't know how you're going to do that? You seem to be a little
filled up right now."
By the time Stephanie had finished giving me my drink, the enema
bottle that hung over my head was empty. She went back to her bag and
pulled out yet another toy. This one was a large penis shaped device
that had a second protrusion coming out of the base about half the
length of the penis. She pulled the large penis slowly out of my
vagina and when it slid out she quickly inserted the new penis to
prevent the pink liquid from leaking out. As she slid it in, the tip
of the second member came to rest against my ass. Stephanie reached
down and pulled the enema tube out then pushed on her new toy pushing
it the rest of the way into my vagina while the second protrusion
moved into my ass. By now, the diuretic was working well and I needed
to pee badly but there was no way that this was going to happen. I lay
there in total misery itching and wiggling and trying to push myself
to an orgasm. Just when I thought that it could not get any worse,
Stephanie reached down and turned on the vibrator inside the latest
toy.
I lay there on the bed writhing, fighting the restraints that held me,
trapped somewhere between agony and ecstasy. The entire time,
Stephanie watched and occasionally would adjust the position of the
vibrator or reach down and tweak my nipples. With every groan or
muffled scream her smile grew bigger.
It was sometime later, probably 30 minutes, but it seemed like hours
that she turned off the vibration and allowed me a little relief. I
lay there covered with sweat, still pulling at the ropes. She smiled
again and looked me in the eyes, "It looks like my little princess is
having a difficult time of it. I guess maybe I mixed up the solution a
little strong. Well I'll tell you what. I am in a caring mood tonight,
so if you need some relief, I am willing to make a deal. Would you
like that?"
At this point, I had no choice but to deal with her. I nodded my head
as best I could to let her know. If there were any other way out, I
would have taken it, but I knew that if I declined, she would simply
flip the switch on the vibrator and let me suffer, all night if that's
what it took!
She smiled, but it was a wicked grin, "OK, here's the deal, take it or
leave it. I will untie you and remove all my little toys allowing even
that nasty pink fluid to drain out. I will even give you something to
rinse with that will relieve the itching. It may take some time for
the numbness to wear off, but you will just have to live with that.
Now then, after I get you all cleaned up, I want to go to a club down
town for a little late night entertainment. I will dress you
accordingly and you will do exactly what I say. If you do, of your own
free will, we will both have a good time, but if you don't, I will use
one of my special little words and then you will have no choice but to
do as I say. But let me warn you, if I have to impose my will, you
will find yourself doing things that you never thought yourself
capable of, and some of them might leave permanent scars, both
physically and mentally. Do you understand? Are you still willing to
make the deal?"
I thought about it for a second, but in that second, Stephanie saw
some doubt in my eyes. She reached down and turned on the vibrator and
once again sent me through the roof. I instantly knew that I had to
take the deal and began begging and pleading as best that I could
under the circumstances. She reached down and shut off the vibrator
again. "Am I to assume that we have a deal?"
With tear filled eyes, I nodded my agreement again. I simply could not
take another minute of this torment. As I lat there thinking about my
fate, Stephanie went about removing the bonds and allowing the enema
to drain. When she was done, she headed me to the shower to get
cleaned up while she prepared my outfit for the night.
When I returned to the bedroom, Stephanie had changed cloths and was
waiting to help me into my outfit. She was dressed in black leather
and had the look of a wicked mistress. My outfit was lying on the bed,
what there was of it. There was a silver halter dress that used a
minimal amount of material. There were panties, garter belt and
stockings all in silver to match the dress. On the floor was a pair of
silver sandals with five-inch heels.
It took only a few minutes for Stephanie to get me dressed. She then
sat me at her dressing table and did my hair and make up. It was
unusual for her to do this since I had become an expert after
attending beauty school, but tonight she insisted. When she was done,
my hair was in a French Braid that fell between my shoulder blades. It
was tied off with a silver bow. My make up was done in a very dramatic
fashion using lots of blue and silver shades. Stephanie handed me a
little silver clutch purse and said, "Let's go. The night is going to
pass us by and we still have lots to do."
As we got into her car, I discovered just how much trouble I was in. I
opened the purse to look for a tissue. There were none there. The
purse contained the make up required for any repairs this evening, and
condoms! Lots and lots of condoms!
We drove downtown, and ended up in a trendy section of the near north
side. The streets held restaurants, bars and clubs of all kinds. After
parking the car, we walked about two blocks until Stephanie led me
into a dark looking place called, ‘The Inferno'. We were led to a
small table, and Stephanie ordered drinks for us. It was not long
before men and ladies began stopping by just to say, ‘Hi'. It seemed
as if Stephanie knew everyone there. As I looked around, I began to
notice the there was an obvious bent towards cross dressers and
bondage on display by the various customers. There were accomplished
drag queens to novices and all phases in between, most of them in the
company of a dominant partner, some male and some female.
After a while, we moved to a different location near a stage in front
of the club. The chair that I was shown to was made of polished wood.
It had legs that curved forwards and back that gave it a particularly
oversized look. The back of the chair was taller then my head and had
a carved recess where my head rested. There were raised arms that were
at table height. As I seated myself, Stephanie stepped behind me. She
quickly pulled a collar around my neck and fastened it in front. As I
tried to move my head, I found that the collar was fastened to the
back of the chair holding my head firmly in place. Stephanie continued
by securing my wrists and upper arms to the arms of the chair and my
ankles to the front legs of the chair. A final strap was placed around
my waist, and once again I was helpless.
Stephanie sat at a chair across from me and ordered us more drinks.
When my drink was set on the table, there was no way for me to even
attempt to pick it up and drink it. Stephanie, however, was quick to
solve this problem. From her purse, she brought out a large penis
shaped device complete with scrotum. She placed the head of the penis
up to my lips and told me to open up. When I did, she pushed the
device about three inches into my mouth and fastened it with a strap.
She picked up my drink and poured it into the top of the scrotum,
which was open like a cup. When she was done, she smiled, "Now all you
need to do when you get thirsty is suck. Go ahead and try."
I sucked, and was rewarded with a mouthful of my drink. The taste was
good, but very strong. I knew that Stephanie was intent on getting me
very drunk very quickly. I sucked again pulling more of the cool
liquid into my mouth hoping that maybe it would help me to relax.
As we sat there, several people stopped by to talk with Stephanie.
Almost all of them left a little token on the table when they left.
Soon, there was a growing pile of red, blue, white and purple tokens.
Many of the people, male dominants, would buy drinks for us. Whenever
they did, Stephanie would say, "Drink up princess, your latest admirer
has bought you a drink." I would suck away the remains of the last
drink, and she would pour in the new drink. Throughout the night, my
cup never ran dry.
After a short while the curtains on the stage were opened. It was time
for the entertainment to start. There on the stage, were all kinds of
bondage equipment. There were already slaves strapped and tied to
several of them, both male and female. In the center of the stage was
a wooden structure that looked like a version of a doctors'
examination table right out of the Middle Ages.
As we watched, a female dominant led her male slave to the device and
strapped him to it. He faced the table and was bent over with his butt
high in the air. His feet were pulled wide apart and attached to the
legs. His torso was strapped down to the table. There was space cut
away in the top of the table to access his nipples, and his mistress
quickly added heavily waited clamps. His head was pulled back and
secured in such a way that it caused his mouth to pull open. When this
was done, his mistress pulled up a small table of various toys. There
were probes, vibrators, whips, crops, feathers and more to choose
from. Also on the table was a small pile of tokens, red, blue, white
and purple.
The mistress on stage picked up the first of the tokens, it was a blue
one. She looked at the token and read from it, "Blue 23." From the
side of the room, one of the female doms walked up on to the stage.
When she got there, she took a minute and selected a long vibrator
from the table. She lubed it with oil from a small bottle and moved
behind the helpless guy strapped to the table. Before he could even
flinch, she had buried the vibrator to the hilt in his backside. She
flipped the switch and started the vibrations and turned to walk off
the stage.
The mistress picked up the next token, "Red 16." This time, a leather-
clad male walked up on the stage. He wasted no time and walked
directly in front the bound slave. He lowered his leather pants and
revealed a huge rigid penis. With out any further to do, he inserted
it into the mouth of the victim. It took him several minutes of work
before he finally shot his load. The slave tried hard to swallow it
all, but some of it ran out of his mouth and down his chin.
For the next hour the mistress selected tokens and the doms came up on
stage to have their way with the slave. I quickly learned the system;
Red for oral, blue for anal, white for sexual and purple for
punishment. After an hour, eight different mistresses and masters had
abused the slave in various ways. The affect of the show was not lost
on me. I glanced down on the table in front of me at the pile of
tokens. As best as I could count, there were 27 of them there. I was
suddenly terrified to a depth that I had never felt before.
Stephanie was pouring another drink into my cup when she looked and
saw the terror in my eyes. "Oh don't worry dear. The straddle horse is
only used on slaves that have been behaving badly. I just wanted you
to have first hand knowledge of what can happen to a slave that
doesn't obey. Now, do you understand? As long as you do exactly as you
are told, you can avoid the horse. If however you misbehave, you get
to ride the horse until all of the tokens in front of you are used
up."
I watched as the first slave was removed and the next one secured onto
the horse. This time it was a female, and on the table was a pile of
almost 50 tokens. She was going to have a long, long ride.
While the entertainment continued on the stage, Stephanie released me
from the chair. She also removed the cup from my mouth. "Now, here is
where you keep your part of the deal. You have thirty minutes. During
this time, you will select and service three people in this room. You
must choose at least one male and one female the third is up to you.
You must also choose one slave and one master or mistress. The third
is also up to you. You must do this on your own with in the time
limit. If not, we will see about cashing in these tokens."
It was not as easy as you might think to get everything accomplished
in the time allowed. Every one had their own agenda and wasn't
necessarily interested in my services. Finally, however, I got it
done. I orally serviced a female slave while her mistress paddled my
ass. The paddling didn't count for anything but made me work harder.
Then I was taken from behind by a male dom while his female slave
serviced me orally. Stephanie allowed me to count both of these or I
would not have made the time limit.
When Stephanie dropped me at my apartment, she gave me orders to get
some rest and be at her apartment at 10:00 in the morning. "Wear you
maids outfit, the apartments is a mess and you can take care of it for
me."
Over the next few months, my relationship with Stephanie changed. She
had become interested in a guy and for the first time that I can
remember she was completely and totally in love with some one that
loved her back. She and I had a couple of girls' nights out, but no
more of the high adventures that she had taken me on before. This
actually came as a welcome relief to me.
The following spring, Stephanie and Harold announced their engagement
and were married in June. I was a little disappointed at not being the
maid of honor, but still got to be a bridesmaid.
Over the next year, I went through a period of adjustment in my life.
I became comfortable with my job and my lifestyle and enjoyed the fact
that Stephanie had refrained from any further punishment or
embarrassment sessions. I dated frequently but never really had a
steady. My sex life was fine and I benefited from a girls ability to
get it when she wants it and turn away when she doesn't.
Although I dated Justin several times, it was never a steady
relationship. I was therefore totally surprised when for Christmas he
gave me a diamond and asked me to be his wife. I answered immediately,
throwing my arms around him and kissing him. We decided on a June
wedding just as Stephanie had done. I was the happiest girl in the
world.
It was two days later when I was able to tell Stephanie. Although she
was happy for me, there was a little of something else also. We talked
for a while and I told her how happy I was. I must have become a bit
over enthused because I heard Stephanie say, "Tiffany needs a nap."
And the next thing I knew I was waking up in a chair with my hands and
feet tied securely.
I looked at Stephanie with a puzzled expression. She looked back with
a solemn look. "Tommy is back." And for the first time in over two
years he was.
I was in a total state of shock. I had to get used to my body, and the
fact that I was engaged to a man. My brain was spinning. I was aware
of everything that had happened to me over the past few years, and my
brain was in turmoil. Stephanie sat there looking at me and in her
eyes for the first time, I saw compassion.
She spoke softly but with an honest tone, "We have come a long way
haven't we? I guess that the two of us have come as far as we can go.
I have taken my revenge out on you many times over, and now it is time
to call it off. I am going to untie you, and then I am going to give
you a special coded message. This message will remove all of the power
that I hold over you. You will be totally free to choose as you wish.
If you decide to seek revenge from me I will understand, but I hope
you will not. If you decide to return to your life as Tommy, I will
help you in every way. Although there are some things that have been
taken from you that cannot be returned, I will do what ever I can. I
simply have to let you choose your own direction.
With that, Stephanie bent down and whispered in my ear as she removed
the ties. When she was done she sat back and waited for me to speak. I
waited also. I wasn't sure what to say. When I finally spoke, there
were tears in my eyes and as I spoke Stephanie joined me in a good
cry. "Stephanie, I love you. I have since the day that we met. My love
for you is different now, for obvious reasons, but it is no less
strong. I have learned a lot over the past few years, and the lessons
were hard ones. I will be forever ungrateful to you for a few of them,
but ever so grateful for others. For now however, I have a question
for you."
She sat there still with tears in her eyes. I am sure she could not
realize the question that I would ask. When I did, I got the reaction
that I expected. "Stephanie, would you be my maid of honor? You see,
Justin and I are planning a June wedding and I have got to start
planning."
The wedding was a grand affair. Justin spared no expense. His family
was expecting a huge wedding and he did not disappoint them. After the
wedding we honeymooned in Hawaii and Paris before returning home. Home
now is a twenty-room house on ten acres of land in one of the most
elite suburbs northwest of the city. I no longer work at the office,
and spend my time being the lady of the house and serving the social
and personal needs of my husband. Although I cannot have children,
Justin and I have discussed it and we have decided to adopt. We plan
on two or maybe three, and I am looking forward to being a mother to
them. It seems as if those earliest of feelings of wanting to be a
girl have finally taken over once and for all.