Date: Wed, 30 Sep 2009 15:22:54 -0400
From: Jessica
Subject: Jessica's Catwalk Confidential

After my mother died, we had to leave our house and I ended up living in
the apartment above my fathers shop. My sister had left home and my father
remarried and moved out. By this time I was a teenager and I decided to
stay in the apartment . That meant that I was left alone at night, a fact
that gave me time to indulge in my secret passion: dressing up, trying on
and wearing the dresses and skirts I found in the closet and every storage
box in the attic. I began to experiment with cosmetics as best I could, and
being a slim teenager I developed my ability to become the woman I wanted
to be- and there was no doubt that I passed very well indeed. But there I
was, all dressed up and nowhere to go.

During this period of my life my main transportation method was hitch
hiking, which in those simpler days was the normal way to get around. Once
when I was about 19, I was returning north from a trip to London and as
usual I was trying to hitch a ride by the M1 motorway. I had been there
about 40 minutes when a dark blue Jaguar pulled up and a (cute) guy about
32 leaned over and asked me where I wanted to go. I shared my intended
destination and he said 'fine, hop in' so I did.

He was heading north to a destination about 10 miles short of my own, so I
settled in to the lush leather seats and silently thanked the higher powers
for bringing me such a plush ride- so far , score 1. It was only thinking
back later that I realized that in an amazing cliche, the radio was playing
the Kinks 'Lola'. Later I would learn how appropriate that was. His name
was Terry and he told me he was heading home after a few days on business
in London. We engaged in small talk for the next few miles. He was easy to
talk to and really friendly. He asked me to reach back into the car to get
a map, and as I did so I dislodged the bag on the back seat which fell to
the floor. I scooped up the contents and noticed a copy of a TV magazine
featuring a beautiful young TV on the cover. For a moment I was transfixed-
I had never seen such a thing . I was frozen- not wanting to appear
inquisitive and yet bursting to dive into the forbidden pages. He must have
noticed as he glanced around and in a carefree manner he said

"There are some 'Tranny Mags' in there if you're interested, feel free to
browse" as though it were a menu arriving to order lunch. I was dumbstruck
and frozen like a deer in the headlights. I desperately wanted to explore
that magazine but I couldn't move. My whole life to this point had been
based on hiding this desire and now here I was in a situation that was very
new. I needed to advance carefully.

"I ... um... er.. well I ... could, er...maybe ... " I uttered gracefully.
He shot a look in my direction and a sly smile appeared on his lips. His
tone now had become much softer and , well ...supportive.

"It's ok if you want to have a look. I like transvestites- no big deal. You
know what a transvestite is I presume?"

" oh yeah " I mumbled trying desperately to cover my ignorance. As it
happened I had come across the term a few days earlier in the newspaper
reporting on sex change operations in Casablanca. Transvestites had been
transformed into women and as their beaming smiles shot from the page I was
introduced to the word. Whatever it meant the view of these delicious women
on the page was enhanced by the knowledge they were men and I wanted to be
there with them- somehow.

The next few miles were driven in total silence as I thumbed through the
forbidden pages. From each one, the faces of pretty transvestites stared
back, inviting me into their world of feminine allure. Terry's voice
snapped me back into reality.

" You like ?" he asked. The moment of truth. Should I say anything? Should
I break my own rule to 'never ever say anything to anyone'.  As usual , all
I could do was stammer.

"I....um .. I think they are..... well... " I flushed beet red. I wanted to
tell him about my own desires , about the fact that I too felt comfortable
in a dress and hi heels. But all that would come out was a mumbled
response.

" I 'm not sure what to say " I offered up finally. Terry was seemingly
amused by my apparent torture. He smiled and told me not to worry. Somehow
I think he sensed my suppressed desires but valiantly held back.

"Look" he said finally. "I'm having a party at my place this evening. Why
not detour and come on over and hang out. I have a few close friends coming
over. It's no big deal and I think you might enjoy it".

I accepted immediately. I wasn't in any sort of mad rush and I liked this
guy. He made me feel comfortable and there was the tranny thing. I didn't
quite know what it was but I was intrigued and I wanted to find out more.

For the next ten miles or so we chatted and laughed at each others dumb
jokes. Finally we pulled into a secluded driveway which lead to a beautiful
old house that sat in it's own grounds. Terry pulled the car up to the
front door and killed the engine. He turned to me and said

" Well here we are. It's not much but I call it home. Give me a hand with
the bags and I'll show you your room".

'My room?' I thought, having expected to sleep on a couch. He took my bag
into the front entrance hall and headed for the staircase that led to the
upper floor.

"In here " he motioned, pointing with the bag to a doorway at the top of
the stairs. The room was nothing like I expected. An overall Lilac shade
greeted me as I took in an old oak bed in the middle of the room covered in
layers of expensive duvets and pillows, all with a matching lilac floral
pattern. On the opposite wall was a dressing table and mirror on which were
placed a variety of grooming tools, hair clips, jars filled with cotton
balls and so on. Overall the room had a very feminine feel and I instantly
felt comfortable. Terry motioned off to a door on the opposite wall and
indicated a bathroom. I had never seen such a thing as a private bathroom
off the bed room and my wide eyed expression must have indicated as such.

"Don't worry," he said "This room used to belong to my sister but she
doesn't live here any more. Go ahead and use anything you want to. There
are even some of her clothes in the wardrobe" he said winking. That took me
by surprise and I glanced back on a double take I saw the door closing as
he left the room.

"Get situated and then come downstairs and we can have a drink" he said
departing.I took but a few minutes to get 'situated'. I wasn't carrying too
much with me as I had been on the road for some time and most of what I did
have was ready for the laundry. I wondered what I would wear for the party
that night. I followed Terry downstairs and into the spacious kitchen and
was greeted by a welcome glass of beer. Terry already had a glass of wine
in hand.

" Come on in , make yourself at home " he said and I complied. We sat
around a large kitchen table and chatted about this and that and before
long an hour had passed. Terry was by this time the better side of two
glasses of wine and was waxing lyrical. He talked about his life growing up
in Sheffield, a scruffy Yorkshire steel town , how he escaped to London to
become a fashion photographer. Things had not gone the way as planned and
somewhere along the line he had started to do his own hair and makeup and
to cut a long story short, he now made a very good living doing hair and
makeup for other photographers.  I didn't have much to add to this. I was
still young and had no clear idea of where I was going or how I was going
to get there. Terry once again asked me if I had a girlfriend and once more
I told him 'no' I didn't.

"Do you mind if I share something with you " he asked.

"No, of course not" I replied. By this time the beer had had a smoothing
effect on me and I think I was ready to hear anything.

"When I was younger, I enjoyed wearing women's clothes" he said in a matter
of fact way. He sat back and let the words sink in, a comfortable smirk on
his lips. I could tell that in some way the words had formed as a
challenge, but I was too dumbstruck to fully take advantage at that time.

"Wow" was all I could muster, and then what seemed to obvious question "Do
you still do that ?"

"Actually no, well, lets say not as much as I used to. For a while there I
was contemplating going full time." He chuckled.

" A sex change? " I asked

"No, well not exactly. For a while I would go several days in 'drag' and
not even think about it. Of course in those days I was a slim teenager, not
unlike you are now, but eventually my body had a testosterone explosion and
developed in more masculine ways and now it doesn't quite hold together
like it used to. I might dress tonight but it's a special occasion."

"Tonight ? " I spluttered. "What do you mean?"

"Didn't I mention it " He said nonchalantly. "The party tonight has a drag
theme" He turned to me and looked me in the eyes." I think it would be
really great if you would let me dress you for the party. You might even
enjoy it" he said playfully.

Enjoy it ? my heart skipped a beat and I couldn't quite believe what I was
hearing. He wanted to dress me as a girl for tonight's drag party ? Had I
died and gone to heaven? Every ounce of my being wanted to get out of the
chair and scream 'YES!'. Unfortunately, I had years of self preservation
tied up in a simple rule. Never ever tell anybody that I enjoyed wearing
girls clothes. Ever, EVER !! Now, even though I could see that I was in a
totally supportive situation I still couldn't bring myself to let go.

" what do you mean ? " I asked sheepishly

" Well," he said, getting up out of the chair and clearing away the
glasses.  " I think that you would make a really beautiful woman, and I can
transform you into such a creature of delight that you will be the belle of
the ball, and if you enjoy playing the girl, we can explore much more later
after everyone has left. What do you say ? Give it a go?"

My stomach was in knot. I wanted to just say 'yes, of course, lets get
started', but instead I couldn't catch my breath and all I could do was to
look at the table. Sensing that I was uncomfortable with the proposition,
Terry became very conciliatory and started to apologize for being so
forward.

"I sensed it might be something you would be interested in" he said, "I
thought after you had spent so much time with the magazines that you would
want to check it out. I'm sorry. I misunderstood. If you want to leave I'll
be happy to give you a ride" He said. It was now or never, I had to throw
caution to the wind and take the opportunity. I looked up from the table as
Terry was crossing the room to get his keys.

"Terry I would love that." I said. " I can't think of anything I would
enjoy better. I have dressed before, in private but I've never told that to
anyone else on the planet before. I guess I'm a little nervous. It's not
every day I get the offer to transform."  I felt a tear well up in my eye
and I looked away not wanting to appear weak.  "Don't cry," he said,
crossing the room and putting his arm around my shoulder. I shook my head
as if to say' don't be silly- me cry?' but I was crying, tears of joy and
as I turned to him he enveloped me in a bear hug and comforted
me. Smoothing away the tears he looked at me and said

"You will remember tonight for the rest of your life and I'm going to make
sure you are the prettiest girl at the party."

Terry left the room to go upstairs and draw a bath for me. I was ready for
a bath as by this time I had had several days on the road. In those days I
wore my hair long. I had a beautiful mane of black hair that was thick and
wavy. I tied it in a ponytail for the most part but that didn't mean that
by now it wasn't ready to be washed . As he had promised he went upstairs
as I sat and composed myself and wondered what the night would bring. The
knot in my stomach had only grown larger by this time and the anticipation
of the transformation was almost too much to bear. That alone would have
been enough to demand a few moments of inactivity to resolve, but in
addition I was rock hard with anticipation. What did he mean by 'we can
explore more after everyone had left.' I had never had sex with another man
or even had the desire to explore, unless I was dressed and on several
occasions I had wondered what it would be like to play the complete role of
a girl. If things worked out maybe tonight I would find out.  Eventually my
hard-on softened enough for me to navigate movement and I followed Terry up
to my room and into the en-suit bathroom which by now was full of steam and
a delicious perfumed fragrance permeated the air. Terry had plied the bath
liberally with bath salts and bubbles and I eagerly stripped off and
climbed into the scalding water. It felt so good to be enveloped in the
bubbles and I could feel the water softening my skin. I was blissfully
hairless in those days and so I only had to worry about cleaning up a few
errant facial hairs. I quickly took care of the facial hair with a razor
that had been left on the side of the bath and the sat back and luxuriated
in the steaming water.  I could hear Terry moving around in the other room
and finally he put his head around the door and mentioned he had left some
skin products by the dresser. He wanted me to call him when I was ready and
he would help me apply what was needed. I was too excited to wait and
before long I had washed , shaved what I could and was drying myself with a
huge fluffy bath towel. I decided I would jump into the role and I
eventually wrapped the towel around myself as though I was already a young
girl, making sure the top of the towel wrapped around my bust to maintain
modesty by covering my breasts. With a smaller towel I rubbed my hair and
then wrapped it up into a turban.

"Ok I'm ready " I called out and Terry appeared at the door with a smile on
his lips.

"Very pretty" he offered, and I instantly felt myself blushing. "Come on
dear, lets get you ready to get dressed" and with that he led me by the
hand over to the dresser.

The top of the dresser was crowded with different products. Terry was not
at all shy and soon I was covered in a sweet smelling skin conditioner that
made my skin feel soft and sensitive. Over the course of the next few
minutes I was rubbed, smoothed and generally pampered by my new teacher. He
took away the towel covering my body, but sensing my nerves he slipped a
silk robe over my shoulders and I reached back into the arms and tied it in
front of me. The satin texture of the robe over my freshly shaved and
conditioned skin sent spasms of delight racing through my loins. I sat in
the chair and crossed my legs so Terry would not see my excited and
enlarged member. This resulted in a very demure sitting position which
Terry duly noted. Without a pause , the towel was whisked from my head and
Terry set about playing with my long hair, fussing and prying with obvious
confidence in what he was doing. Pretty soon he had snipped it into shape
and piled it high with rows of large hair curlers. Then came the foundation
for my cosmetics. He insisted on covering the mirror so I could not see his
progress, but it was clear that he was now in his element as I willingly
relinquished control to his obvious experience. I sat back and enjoyed as
he applied layer after layer of foundation, blush, eye shadow, mascara,
false lashes and finally lipstick. He then set about giving me a manicure
and a pedicure a process that was less than pleasant, but much needed if
the end result was pretty fingers and toes rather than hands that looked as
though they had just built a house. Finally I sat in the chair blowing a
set of freshly painted false finger nails in a silk robe and my hair in
curlers. I still had no idea what he had done. I was about to discover he
had changed my world.  Leading me by the hand he took me over to the bed
where my heart skipped a beat as I spied a collection of sexy lingerie he
had laid out on the bed. In matching black satin and lace there lay a pair
of exquisite panties alongside a beautiful corset waist cincher and a pair
of black stockings. First of all he produced a gaff from the pile of neatly
folded clothes and helped me into it, instructing me on how to place my
penis in a way that resulted in a flat tummy. Next he helped me as I placed
my feet through the legs of the panties and pulled them on over the
gaff. He held the corset so I could pass each arm through the straps then
gathered it behind me, first fastening all the clips then increasing
tension on my waist with the laces. I could feel it getting tighter but
before I had trouble breathing he lessened the laces and tied it off.

"Not too much for now" he said. "We can tighten that later if you want."
Next he sat me down as he helped me on with each stocking, gathering the
material so that my toe touched the end of the stocking first then he
rolled each one up to the top of my leg, pausing only to gather the
material along the way. Finally he passed the suspenders under my panties
and clasped each one shut, capturing a piece of nylon in order to keep them
up. Bidding me to stand , he pulled a pair of slinky sandals from under the
bed and helped me as I carefully placed each foot into the high heeled
shoes. My head was swimming. As always it was the addition of high heels
that transported me into the world of Jessica , my feminine persona. Terry
however had not yet finished. Pausing for a moment to get his bearings, he
glanced over to the drawers in the dresser and in a moment he had a silky
black slip in his hand. He again gathered the material and passed it over
my head being careful not to touch my makeup. I wriggled and took the
material down my body . It was snug but amazingly it was a perfect fit. I
looked down at the satin skirt of the slip covering my stocking clad legs
and let out a moan of delight. It was too much. I was glancing around for a
mirror , desperate to see what wonders had been created but Terry was not
yet finished.

"Not yet young lady" he scalded. "sit down and let me finish that hair".
Painfully he removed all of the curlers and then started to brush it
out. Seemingly changing his mind halfway through he had me stand up as he
moved over to the closet. He returned with a beautiful black chiffon
dress. I could see why he had chosen a slip. The material was translucent
and had there not been a slip anyone could have seen what I was wearing
underneath- a fact that didn't exactly bother me at the time. The dress had
a modest plunge in the neckline to show off what cleavage I could
muster. It was gathered at the waist then flared out in the skirt to rest
just above my knees. I eagerly climbed into the bodice as Terry again
turned me around and I felt the zip slowly run up my back to close at the
top and seal me into bliss. Smoothing the skirt I sat down and crossed my
legs. I could feel the two layers of nylon connect and felt the silky
softness of that materiel. I couldn't help the urge to caress my leg with
my hand.  Terry continued to brush out my hair, teasing it into position as
he worked to make it perfect. Finally, the moment was right and as he
offered his hand and led me to the center of the room in front of a full
length mirror covered with a sheet.

"Voila !"  he cried , whisking the sheet from it's perch. I was
stunned. Before me stood the most convincing and beautiful woman I had ever
seen. My hair was falling in long curly waves, gathered in away that left
no doubt as to the feminine intention of the style. My cosmetics were
applied to perfection, he had stayed in a pale spectrum to contrast with my
dark hair and dress and so the face of a pale, demure girl blinked out from
under huge eyelashes. It was as though the dress had been designed
especially for me. It clung to my body until the waist then fell to my
knees in a beautiful gathering of material. I was speechless. I looked at
Terry as though not quite comprehending as he smiled back, obviously proud
of his accomplishment. I twirled back and forth making the skirt fly. I was
truly in heaven."Ok nearly finished " he said crossing to the dressing
table. He grabbed a small box and returned to where I still stood
transfixed in front of the mirror. " Here try these" he said, attaching a
pair off dangly earrings to each of my ears. Luckily it was the fashion to
have pierced ears at that time so I had no trouble attaching the ear
rings. Next he pulled out a gorgeous matching necklace of what I took to be
feaux diamonds set in white gold. It was not until much later I learned
that they were real diamonds. He turned me around and as I looked into the
mirror he fastened the clasp behind my neck. It was perfect. The earrings
and the necklace were indeed the finishing touch and I let out a gasp. I
had no idea I could ever be so beautiful, and any apprehension about
attending a party of strangers lifted away."Ok my dear" said Terry. :"Now
it's time for me to get ready so if you will excuse me I'll be back
shortly. Take a look around the closet area and try to find a purse you
might like then relax. And don't mess up that makeup young lady !".

I was expecting Terry to return in a dress and heels but I was startled to
see some time later that he had changed into a black suit with a ruffled
shirt open at the collar. He looked very sexy and sophisticated. For some
reason this made me feel slightly uncomfortable. I had assumed we would
attend the party as sisters, or at least lesbian lovers, but now it was
clear things were unfolding against a larger design. Terry must have sensed
my apprehension. Taking my hand in his he sat down opposite me and began to
speak in a soft tone.

"what's the matter" he asked "why so blue?"

" I'm Ok" I blurted" it's just , well I thought we would all be
dressed. You had mentioned that you dressed as well- I just figured we
would all be dressed. I just don't think I can do this if I am the only one
dressed. I've never done this in public and, well frankly I'm a bit
nervous."

"Of course you are- wouldn't be human if you weren't , but don't worry. I
promise you will be fine and you WILL be the belle of the ball. I promise".
His words were beginning to sound a little hollow. What had I let myself in
for?  It was one thing to think of dressing up to be with other TV's at a
party - fun, fun, fun ! But what had this turned into ? My stomach returned
to it's familiar knot and I felt myself become short of breath. In a way it
was a feeling that was alarming and exciting all at the same time. I could
tell that Terry was empathetic to my feelings, but he didn't back
down. Once I had stopped squirming he continued.

"Look, I'm afraid I havn't been entirely truthful. It's true I am having
some friends over this evening, they are TV's and we do intend to have a
great party."  I could feel he was about to add the word 'but...'  "But.,
that's not entirely the whole story. You see, I have branched out into
clothing design recently and tonight I intend to show my new line. It's
rather unique because it is sized and designed to crossover between the TV
lifestyle and regular women". He said pensively. " I want to exploit the
marketing to play directly both to Women and Transgendered." He said. "I
have a theory that most young boys play around with the idea of
transvestism but for a variety of reasons they do not pursue it- I think
that is one reason why our society frowns so much on it. It's because most
of our native sons would rather be in heels and makeup for at least some
part of their lives. Other cultures are not so condemning of the lifestyle
and in India and Thailand it can be a badge of honor to have a Katoy as
part of the family. Hell, in India they are respected members of the
community." I didn't really care about what happened in India or Thailand
(not until later when I found out how cute Thai katoy can be). What
mattered to me was how the hell I was going to manage all of this. Why was
I here?

"why me ?" I asked somewhat forlorn.

"I knew it had to be you when I saw you by the roadside this morning. You
looked so vulnerable and I thought 'if that guy isn't what I'm looking for
then to hell with it..When you picked up the magazine from the back and
became so transfixed, I knew. You see, I can't do this with a seasoned
transvestite, I need someone who is on the verge of admitting this to
themselves, not a seasoned pro who exists behind an attitude that is so
complete that nothing can get through to hurt them. I need innocence and
you have it in spades my dear. Look at yourself" I cast an eye towards the
mirror."Look how beautiful you are, and don't tell me you are eager to get
out of that dress- I can tell- honey, you're a natural" he said gushingly.I
knew I was blushing and I also knew I had no power to resist. He was right,
I had never felt so comfortable in my life. I felt as though I belonged for
the first time I could remember, and although I suspected it was all an
illusion, I was ready to comply because deep down, I wanted to please my
man.......which in itself was an utterly new sensation and one that left me
slightly worried. I knew that if I could remain confident that I could
probably pull this off, although that was a tall order. I was wearing
delightful strappy sandals with a 4 inch heel which did wonders for my legs
although they were a little hard to walk in gracefully. Terry sensed my
concern and set about giving me a crash course in feminine deportment. I
was an eager student, and in what felt like no time at all I was able to
sashay comfortably. Terry was a great teacher- maybe the evening could be
interesting after all.

Some short time later the first of the other 'girls' started to arrive. I
was introduced as Jessica and that alone. I met each an every one of
Terry's friends as they arrived, Amanda was first and arrived in a halter
top, jeans and sandals. Terry instantly hustled her into the bedroom and in
no time she too was wearing one of Terry's creations from his day wear
line. Next he set about piling her long hair into a sophisticated bun and
Amada was ready to rock! She was also really friendly with me and As Terry
greeted each of the girls , Amanda took me under her wing and explained the
way the night would go. First we would model daywear and then finish the
night with evening gowns. Some of the models would be TV and others GG. I
instantly assumed Amanda was a GG but later I was stunned to learn that she
was not only a TV but part time, only really dressing to visit clubs and
special friends. At this she winked and I felt my knees buckle. Luckily I
don't think she noticed. The rest of the girls had arrived by this
time. Nicole, a stunning colored girl was beautiful but distant. Angela had
a cold so she was 'here for Terry' and took great pain to let everyone else
know how she suffered. Patty was a sweet girl who seemed to be in a similar
situation to me, somewhat nervous but excited at the prospects. I later
discovered she was the GG of the crowd. Several other girls had arrived but
I did not get a chance to meet as by now things had become quite
chaotic. Terry was running around gathering girls, sewing seams, zipping up
dresses and getting everyone ready. By now I was able to see a distinct
style emerging in Terry's designs. His work seemed to fit into a category
of retro Fifties wear; cascading skirts, cardigans, sleeveless blouses. All
very pretty and very feminine. The girls looked stunning. I hoped I looked
half as good.

I stood by the wall with my feet together and my hands clasped in front of
my dress, hoping that I didn't stand out. The feeling of my nylons brushing
up against my slip and skirt continued to send shivers down my spine. I was
having the time of my life.  All too suddenly Terry emerged and began to
line up the girls. I was number two behind Amanda who turned around ,
squeezed my hand and gave me a small kiss of the cheek.

"Don't forget to stay confident" she said to me pointedly "Don't let them
see you sweat and above all enjoy it- it'll be fun". Good advice although
by this time I felt my legs had turned to stone and I was no longer capable
of independent movement. My stomach had erupted in butterflies and I could
feel myself beginning to well up at the prospect of stepping out into a
crowd of strangers. All too suddenly Amanda stiffened her back, stuck out
her chin and launched off onto the runway. Polite applause greeted her as
she marched down the runway and paused at the end long enough to allow the
audience to lust after her long feminine legs and hopefully notice the
beautiful dress Terry had put on her. Terry leaned over to me and placing
his hand in the small of my back he whispered

" Here you go darling... knock them dead."A soft push sent me in the
direction of the runway, and as soon as my foot hit the carpeted deck it
seemed my mind went blank and I started to move gracefully towards the
end. I was aware of faces looking up at me, but I was not looking at
them. I was in a world of my own where I had always been a woman and now I
had the chance to display that feeling. Arriving at the end I spun around
on one foot while placing the other at a jaunty angle. My hands had found a
natural position on my hips and I could feel the skirts of my dress billow
as I made the turn. I was aware of a slight gasp from the audience and in
an instant I was amazed to hear significant applause and a few
cheers. Without missing a beat I turned and walked gracefully but with
purpose back to the waiting area. The applause accompanied me the whole
way. Bursting through the curtain I was greeted by Terry and Amanda who
gleefully congratulated me. Terry gave me a bear hug and as he pulled away
he kissed me gently on the lips.

'Well done ..I knew it..I knew you would be perfect." He gushed.  One by
one the other girls marched out to show their costumes as Amanda took me
upstairs to one of the bedrooms. Laid out on the bed and around the room
was the most amazing collection of ladies evening gowns. Amanda picked the
first one off the hangar, an amazing creation in taffeta and silk. She
indicated to the second gown, a black velvet creation that swooped down to
the ground leaving a small train.

"You're the girl of honor this evening " she said " You get to wear the
expensive dress. Go on in there and let me help you into it then you can
help me " I slipped out of my dress and hung it on the clothes hangar the
gown had just come off. Amanda held the bodice up so I could carefully
place each foot into it, then she helped me wriggle in and closed the clasp
behind my neck. The gown felt wonderful. It still suited the earrings and
necklace that Terry had given me earlier and so I was ready in no time. I
helped Amanda squeeze into her dress and happily zipped it up in the
back. It felt so good to be 'one of the girls' and she looked stunning. We
returned to the waiting area to watch the other girls and waited for our
next performance.

Terry had by now become somewhat frantic. Torn between guiding the girls
onto the catwalk and making sure they changed into the correct gowns, he
was trying to do too much and I think was missing the fun of the
evening. Several people had begun to wonder around the house by now and I
was trying to stay out of view as much as possible. My hair had be re-done
and was now piled high in a very sophisticated bun with wisps of hair
cascading down the side of my head. I was unaware when a voice alongside my
ear crooned

"You are the best model I've seen tonight" I was startled by the voice and
turning with some alarm I came face-to-face with a handsome man about 30
years old.

"Oh, well.... Thank you!" I managed to stammer, trying my hardest to
modulate my voice to a higher pitch without sounding like something from
Monty Python.

"Seriously, you just glowed out there. My name is Richard," he said holding
out his hand.

"Jessica, and thanks for the compliment. I've never done this before" He
started to laugh which instantly made me feel as though he saw through my
act.

"Oh that's funny," he said " as if....". He arched his eyebrows as if to
question my sanity and I realized he didn't believe me.

"No seriously " I protested.

"Well if that's the truth then I'm really impressed" he replied. " Do you
live in London? I guess I'm asking if you would have dinner with me
sometime soon?"  The question hit me like a brick. I must have turned beet
red and shifted uncomfortably. What did I say to this? The guy was handsome
but I had never regarded myself as gay and right now the biggest problem I
could see was that I wanted to. What was all that about? Luckily I was
saved as Amanda interrupted and after an interested glance towards my new
paramour, she asked me to follow her.

"Look I'm sorry, I have to go and I don't live in town so I think it might
be difficult." I offered as Amanda pulled my arm.

"Take my card and call me then" he said fishing out a business card and
carefully sliding it down the front of my dress. I fished it out and held
it in my fingers as he disappeared into the crowd. 'Richard Hollister-
General Dynamics' it said. I slid it into my purse. Never say never!

It was time for the second round. Amanda once more took the first pass and
I followed closely behind. As I paused by the entrance, Terry came up
behind me and I felt a hand outline the shape of my butt. Under normal
circumstances I may have had a different reaction, but on realizing it was
him it sent a shiver through me as he gently placed a mink stole over my
shoulders.

"This dress was made for someone elegant and beautiful" he said. "The mink
is elegant and you are beautiful so I think we're fine. Again, a gentle
push and I was on the runway and gliding gracefully towards the
audience. Once again there was an outbreak of applause as I flirted with
the crowd as best I could. I turned at the end, paused and then turned
again. I could feel the hem of the gown swishing across the floor and as I
turned to return to the waiting area I glanced Richard Hollister applauding
loudly and with a certain glint in his eye. Did he know? I made a mental
note to ask Terry later.

Back in the waiting area the rest of the girls were lined up and ready to
go. Amanda came over to where I was standing and gave me a big hug.

"You were fantastic" she gushed." You know you are the star of the show-
everyone is talking about 'who the new girl is'. I pretended not to know of
course," she said with a mischievous smile on her gorgeous lips. I was in a
state of shock and I suggested we try to find some drinks as fast as we
could to help me calm down. Just as I spoke a waiter passed with a tray of
Champaign and Amanda and I each grabbed a glass. Moments later we were both
searching out our second. One by one the girls finished the show and
finally at the end we all gathered on the stage as Terry entered to accept
a well earned round of applause. It seems the evening was a success. As the
applause died down Terry turned to me and took me by the hand, leading me
into the throng. I resisted just a little, still nervous that someone would
'read' me. He persisted and I was powerless to protest. One by one I was
introduced to Terry's friends, mostly women in black who I assumed were all
fashionistas. Each one pointedly asked my name and where I was from and
thankfully Terry answered each one saying I was his secret weapon and that
we were lovers so don't try anything. I found this to be slightly
embarrassing at first, but as the evening wore on and the Champaign started
to work it's magic I lowered my resistance and began to enjoy the idea of
being the lover of this man. Terry held my hand for the most part except
for when I closed in to him encouraging him to take me in his arms. His
hand snaked around my back and more than once found its way to softly
stroke my butt. His fingers would occasionally find my suspender clasps
through the fabric and even though it was just a gentle stroke it made me
wild. I could hardly contain myself.

Quite soon after the show people started to leave and before long there was
only Amanda and a couple of other girls remaining. Terry was deep in
conversation as Amanda came up to say good-bye.

"You were wonderful tonight Jessica and I really loved spending time with
you. Can we get together soon? I think you and I need to go shopping so we
can have some girly time together and talk about Men".  she said finally
glancing over at Terry. "Terry, you make sure you don't smother this
delightful young girl. Leave some for the rest of us" She laughed and
turned to leave. Glancing back at me she said softly "I mean it. You are so
gorgeous but you need a woman's touch and that will open a lot of doors for
you- if you want them to open." And she was gone. I made a mental note to
follow through. She was captivating on so many different levels. I was sure
I could lean a lot of things from her and that was part of it. I was also
very attracted to he and that was part of it too. Talk about conflicted!

I turned to Terry as the last person left and slowly moved into his
outstretched arms. As my hands felt the shape of his lapels, I could feel
his hands caress the back of my gown and without thinking our lips met and
he kissed me long and deep. I had no resistance and let out a soft moan as
his tongue played with mine in a sensual probe. My hands found the back of
his neck as our bodies came together in a loving and seductive embrace. I
had never kissed a man in this way and although I knew I was in a new
place, there was no resistance. It was as though I felt it natural to be
doing this after a night learning to accept my feminine persona. I wanted
him to kiss me and I too felt a burning desire to kiss him. Breaking away,
he took my hand and led me up the stairs, past the door to my room and into
the master suite. Holding the door for me, I stroked his chin as I passed,
letting the mink stole slip from my shoulders as I entered the room. I
crossed to the bed and paused while Terry approached me from behind. His
arm passed over my waist as his lips found the lobe of my ear and then the
sensitive area of my neck that made me moan again with delight. I could
feel the zip on my dress start to slide down and before long I was stepping
out of the gown to reveal my deliciously feminine lingerie. He didn't wait
for me to remove any more as he pushed me back onto the bed. Our lips again
locked in a passionate kiss as his hands explored my satin clad body. I too
had exploration on my mind as I tugged at his jacket and then the belt of
his pants. It seemed like an instant before I had his huge cock in my hand
and I set about stroking the length of his shaft while our tongues did
battle above. He was by now beyond restraint as I felt his fingers probe
the edges of my panties and before long my own stiffened cock was firmly
embraced by his willing fingers. I leaned back and let out a sigh of
ecstasy that I thought could never be surpassed. That was until a few
moments later when his tongue had left my lips and was now fully engaged in
kissing the shaft of my cock. Skillfully his lips gently kissed the shaft
starting at the base and working up to the engorged head. I cried out as
his tongue slid over the head of my cock and gently descended over the
entire organ. I thought I would explode. I had never felt such a wonderful
sensation and I became so overwhelmed that small tears started to fall down
my cheeks. I was gasping for him to stop - afraid that an ejaculation at
this point would render me useless for the rest of the evening. Terry
sensed my condition and pulled back just as the first few drops of pre-cum
emerged from my glistening pussy stick. I managed to hold back the rest,
and felt a compelling urge to return the compliment. Terry didn't take too
much persuading. Laying back his huge cock beckoned me and I was only too
happy to comply. I borrowed his technique of slowly kissing the shaft from
the base until after a few minutes his entire cock was in my mouth. I
slowly worked it in and out, each stroke taking it in a bit more until it
was in my throat. I tried to take it in too far and suddenly gagged and had
to stop for fear of vomiting.

"Don't worry, I've got you" Terry instantly whispered.  We rested for a few
minutes while I regained my composure. I lay back in Terry's arms while he
stroked my hair. Before long we were both kissing again. The gagging moment
had passed and my own erection reminded me that I had managed to stop the
ejaculation. I was ready to go again. Terry momentarily pulled away and
grabbed a small vial from the side table.

"Try this, " he said, unscrewing the top and holding it up to my nose.

"What is it? " I asked, somewhat alarmed.

"It's poppers" he said" I promise you will enjoy this." By this time I
trusted him completely and I breathed in the chemical smell as he held it
to each nostril. I became light headed as Terry too took a hit but was
unaware of the influence of the drug until our lips met once
more. Instantly I was lost in the most passionate kiss I had ever
experienced. Our mouths were locked for what seemed hours as the effect of
the poppers flooded through my brain, ignighting a passion I never knew I
had. Unfortunately the effect wore off too quickly. I reached for another
blast but Terry grabbed my hand "Not yet, if you take too much of it loses
its effect and leaves you with a horrible headache. All good things in
moderation. He rested for a while to let the effects of the poppers wear
off. I lay with my head on his chest listening to his rhythmic
heartbeat. As he dozed I played with his semi erect cock, marveling at the
situation and somewhat alarmed by the fact that I was enjoying it so
much. Terry stroked my hair and I could see form his cock that he was
slowly re charging to go again. I leaned down and took the head of his cock
between my lips and he let out a contented moan. Before long our lips were
locked in passion and I could feel the hardness of his cock against my soft
belly, moving rhythmically against me, little drops of pre cum softening
the contact. My own cock again felt as though it would burst. The closeness
of his body was driving me wild, but most of all, his manner was seducing
me into a world I had only imagined. This was what it really felt like to
be a woman. His gentle touch caressed my willing thighs and I gave myself
to him completely. As he nibbled my ear lobe and again drove me crazy, he
whispered into my ear

" Ready to pop that cherry" he asked.

"I'm ready for whatever you want to do my darling," I crooned back to him.
Puling away for a moment he reached to the side of the bed and grabbed a
tube from the bedside stand.

"Turn over" he commanded and I was only too willing to comply. Slowly he
took a glob from the tube and began to massage it into my boy pussy. The
sensations as his finger slid past the sphincter muscle shot through my
body and I gasped at the sudden intrusion.

"This will make it easier for the first few times " he said with a knowing
tone. "It's a special lube that desensitizes you so the stretch doesn't
hurt so much. Leave it on for a few minutes. I'm going to the bathroom and
when I get back it will be ready."  And with that he slid from the bed and
padded over to the bathroom. As he disappeared inside I took a few moments
to catch my breath. Here I lay, in fine silk lingerie, my velvet evening
gown strewn on the floor and my pussy lubricated for further
engagement. What more could a girl want? I was about to find out.

Terry returned in a few minutes and slid into bed beside me. He kissed my
lips and I reached out to him and kissed back. Our tongues once more went
at it only this time I could feel his fingers explore my hole. It felt
different, as though I was only feeling a portion of what was happening but
my excitement grew when I realized Terry was now withdrawing two fingers
and the sensation was wonderful. I turned to lie face down but as I did so
he caught my arm and resisted my movement. Taking my leg he rested it
against his shoulder and taking the other leg rested it against his other
shoulder. I relinquished any form of control to him and lay back as he
stuffed a pillow under my back. I could feel the tip of his cock pushing
against my hole and as it slowly began to penetrate I realized the de
sensitizing lube only worked so much. I began to panic as the pain grew and
it felt as though he would split me. He took it very slowly and as quickly
as it began the pain began to ebb and I could feel his cock inside me for
the first time. Pausing to let the muscle adjust he slowly began the
rhythmic pulse that would take me to ecstasy. Picking up speed, I began to
feel the most amazing sensation as his cock tickled my prostrate. My own
cock felt as though it would burst, but my thoughts were elsewhere. He was
my man, fucking my pussy as I lay on my back. I had never felt so feminine
and I didn't want it to stop.

"Oh god.... Terry this..... is fantastic" I gasped between
strokes. "Please..... don't ...stop.." By now each time he thrust his cock
into me I responded by arching my back to meet him. I could feel him
getting closer and closer and I too could barely keep from shooting my
load. In an increasing crescendo Terry began to indicate he was about to
cum, and as he did so he reached down and caressed my cock. In an explosion
of cum I shot out my load which landed on my chin and face. I didn't mind
as my own thoughts were on the fact that I could feel Terry's cum filling
my hole and dribbling down my leg. I could taste the sweetness of my own
cum on my lips and licked it up in order to swallow it. Terry began to lick
it from my face and pretty soon there was non left. I was not done however
so I leaned down and liked his cum from the head of his softening cock. His
groan indicated he had given all he could. We fell into each other's arms
and before long sleep overtook us both.

By the time I awoke the following morning Terry had already risen and I
could smell freshly brewed coffee. By now I was naked so I grabbed a
blanket and wrapped it around my shoulders. Before I could leave the room
Terry stood before me with two steaming mugs of coffee.

"Good morning" he said cheerily and paused to kiss me on the lips ever so
gently. "Might I say that was a fantastic evening.. and the show wasn't bad
either."I smiled and kissed him again before falling back into bed. "I have
to rush because I have to be on a call downstairs in a few minutes. I've
laid some fresh clothes out for you so why not get a shower, get dressed
and come downstairs when your ready" he suggested , always in control. My
own preference would have been to continue where we left off but I turned
and drank my coffee as he jauntily left the room. For some reason I had
assumed that my girl act was confined to the evening, and so I was
delighted to see that the armchair that sat in the room was draped with
what looked to be a print dress and some delicious looking lingerie. I
couldn't wait to get dressed, but trying to be ladylike I rushed into the
bathroom to shower and freshen up. I was meticulous about preparing myself
and utilized several 'products 'I found in the bathroom. A liberal
application of body cream softened my skin to the touch and I applied
perfume and scented cream for quite some time. Returning to the room I
slipped into the silk panties Terry had left for me laying on the arm of
the chair. Alongside was a bustier that combined a bra and waist cincher
and I took great delight in fastening the back alone. Next I gently
unfolded my stockings up each leg, making sure the seam stayed straight up
the back of my leg. I reached down to grab the dress, and noticed it was a
black polka dot against a white background, while the collar and the belt
that gathered it at the waist was the opposite print. The bodice fit snug
emphasizing the silicone breasts that lay cupped beneath the silky fabric
of the dress. The skirt splayed wide to just below my knee, made somewhat
full by the lavish petticoat that lay beneath. I suspected it was one of
Terry's creations as it had a distinctively retro feel. I loved it and it
fit me perfectly. My adolescent girlish features suited the dress and
stepping back to view the mirror I knew there was one final addition. I
slipped into a pair of strappy sandals and bucked each strap around my
ankles. Oh bliss I thought again. Straightening up and smoothing the front
of my dress I remained transfixed in front of the mirror. I decided a pair
of fifties dangling earrings would work well and I reached down to the
jewelry box on the table. Inside I found several pairs, each one then taken
out and tried against my ears to find the perfect match. I settled on a
pair of simple matching earrings. I stood in front of the mirror for some
time teasing my hair into different styles. It seemed as though my new look
lacked something and strolling over to the closet I spied a wide brim
hat. Taking it out I pulled it down on my head and cocked it at an angle. A
pair of retro sunglasses with winged rims completed the Audrey Hepburn look
and I could not have been happier. In my euphoric state I probably went
over the top as I remember as I left the room my walk developed a definite
sashay. I kept it up as I glided down the stair case and into Terry's
study. As I entered the door I could see a look of approval cross Terry's
face and the feeling I had enjoyed so much the night before was back. I
spent the rest of the day in that gorgeous dress and later Terry took time
away from business so he and I could refresh our sexual memories. Multiple
times throughout the day Terry reminded me what it was like to receive my
man and I loved every minute. Finally the time came for me to leave.
Reluctantly I changed into drab and Terry gave mea ride home. My life was
never to be the same again.