Date: Thu, 13 Aug 2009 00:38:28 +0000
From: cybereena <cybereena@gmail.com>
Subject: TG - Trannie in Training

This is my first attempt at writing fiction. This story did not actually
happen and is strictly a product of my fertile imagination. If you have a
moment drop me an e-mail and let me know if I should continue with this
story line and with writing TG fiction in general. Love ya.

***************************************************************************

Trannie in Training
The Beginning

I was never a good student, so when I graduated from high school the easiest
way for me to find a job was to go into the military. I was infantry pure
and simple. Eventually I got picked up for security and endured that until
the end of my contract. Once back in civilian life jobs were still hard to
find. I finally got a job as a security guard at a large department store.
It was on the night shift and didn't pay that well, but I figured it would
do until I found something better. I found an apartment and a room mate. He
worked a day job so we almost never saw each other. That was fine by me as I
am not that much of a "people person". So what do you do all night long by
yourself in an empty department store? No much. We had a small TV in the
security office, but TV after midnight is the pits. I read some and played
with my game boy. I only had to make rounds once each hour, so there is not
a lot demand on my time. Out of boredom I spent a lot of time just walking
around the store. On one particular occasion I noticed an advertising sign
for some woman's high heeled shoes. The woman in the ad was drop dead
gorgeous of course and was wearing red "fuck me" shoes. I stopped and began
fantasizing about this babe and her shoes. I felt that familiar stirring in
my pants and soon had my tool in hand. It had been a good while since I had
sex.  I have always had a particular fondness for ladies in high heels,
especially red ones for some reason. It felt good to cum in the middle of
the woman's shoe department (or anywhere for that matter). After cleaning up
my mess I went back to my office and felt sort of bad about what I had done.
(But not that bad!)

The next night during my rounds I had to check back with the babe in the
shoe department. She was there with her fantastic shoes. I was thinking that
I would love to see her walk in those shoes. No such luck. I thought about
that as I continued my rounds and had that stirring again that made it
difficult to walk. The next hour I took a slightly different track that took
me through the shoe department. There on display where those lovely red
shoes. I picked the display shoe up and turned it around in my hands. This
shoe was pure sexuality. I was getting a hard on just handling it. It then
occurred to me that I should try them on. I had no idea what size, but I
knew where the stock room was. I got the stock number off of the shoe and
headed for the back. What an enormous amount of boxes of shoes. I finally
figured out the order and found the section with these shoes. I am not that
big so I only wear a man's size 7. I did not know how woman's shoes sizes
ran, but figured I would try a 7. I pulled off my boots and socks. The shoe
was just too small. I tried an 8 and still no luck. I could get the shoe on,
but it was real tight. A size 9 fit pretty well. I put on the other shoe and
tried to stand. Whoa! This is not going to be easy. I spent a few minutes
just getting used to standing. Then I tried a few steps. I nearly fell over,
but persisted. After a few more tires I got so that I could walk, but not to
gracefully. I was glad to sit down. My feet were hurting and there were
marks from the shoes on my feet. I put my socks and boots back on and got
back to work, for what that was worth.

Walking in those shoes became a game and I am just hardheaded enough not to
quit until I could do it. Besides it made the endless nights pass by a
little more quickly. I discovered that if I wore those little stocking
things that they have in the shoe department that the shoes slid on more
easily and didn't leave many marks. I also discovered that if I kind of
moved my hips around like a woman does that it was much easier to keep my
balance. After several hours practice over several nights I got pretty good
at walking. I even made my rounds once completely in the shoes. I happened
to walk by one of those low mirrors in the shoe department and seeing myself
from the waist down in those shoes gave me an immediate boner. I actually
had a pretty sexy walk and was turning myself on! Who would have thought
that? That gave me another idea. What if I were to wear hose too? Only
seeing the legs and shoes I could imagine that I was looking at woman. I
found the lingerie department and picked out a pair of pantyhose. I did not
realize that were different sizes, so I just picked up the first pair that I
came to. I went back to the shoe department, pulled off the shoes and my
pants. How in the hell to do you put on pantyhose? I tried to pull them on
like socks, but that did not work well. I wound up tearing them. There were
two pairs in the package, so I grabbed the other one. I remembered seeing
pictures of woman rolling stockings up their legs to I tried bunching them
up down to the toe and that actually worked! I had one leg pulled all the
way up and now how to get the other one on? I eventually figured out that if
I rolled up the first one to my thigh I could get the other one up too. Once
I had the pantyhose and shoes on I went to for a walk by the mirrors. "Wow,
this is good stuff!" I thought. My legs were bit too hairy for a girl and
sort of muscular, but they didn't look bad. The pantyhose were just the
ticket. As a bonus, the pantyhose felt kind of nice too. I began to stroke
my hard cock through the hose. What a feeling. In no time I was spurting
cum. Back to work.

Back at home I decided to shave my legs so as not to ruin the sexy look of
my legs in pantyhose. Of course I never have shaved anything but my face and
I tell you legs are a bit different. It is hard to get to the back of your
legs and I cut myself several times. My legs were burning a bit, so I used
some hand lotion to soothe them. Now, here was another new sensation. My
smooth legs felt great. I was wishing that I had brought home those
pantyhose and couldn't wait to get to work. Once alone, I headed straight to
the shoe department pantyhose in hand. The hose felt really nice sliding up
my now smooth legs. I put the shoes on and back to my now favorite spot in
front of the mirrors. If I did not know that the reflection in the mirror
was really me I would have sworn the legs in wearing those sexy heels
belonged to a female dancer. While admiring myself I had a thought. If the
shoes and hose are turning me on this much imagine what dressing fully in
woman's clothes might do. I had no idea where to start as far as sizes, but
I had plenty of time alone in the "candy store" to figure it out. Up until
this point I had been returning the shoes to the shelf and stashing the
pantyhose in my locker. I decided that if I was going to keep doing this I
would need to take some of my things home or at least put them in my car.

Over the next couple of weeks I spent a lot of time trying on first panties,
bras and slips. Once I figured out the right sizes I started trying dresses,
skirts and blouses. As a kid my sister was always trying to get me to play
dress up. I always refused. Oh, what I missed. I amassed a number of
outfits, underwear sets, and shoes. I found necklaces and clip on earrings.
I started looking at fashion magazines, but most of that stuff was way
beyond what I could do. I did get an idea of what looked good together and I
think I looked pretty good for a guy. Each new discovery and outfit caused
the same reaction. I had cum so many times during my explorations that I
thought my cock might fall off. As you may have guessed I then progressed to
makeup. That was maybe the most challenging part of all. I had lots of
makeup to choose from and those huge pictures of sexy models in the makeup
department as a guide and inspiration. Putting on makeup became my favorite
part of the game (except for the shoes). Much to my disappointment the store
did not sell wigs. I spent a little time on-line at home searching the
Internet. I  found a few long wigs in various colors and styles and placed
my order. Once I had my wigs my transformation to a sexy babe each night at
work was complete. I would spend nearly the entire shift in drag with at
least one or two outfit changes each night. What started out as a curiosity
had turned into an obsession. I was sneaking out clothes, shoes, and makeup.
I was storing them in my car's trunk, but eventually had to take them into
my apartment. Soon there were almost more women's clothes in my closet and
dresser than there were men's clothes. On my nights off I was dressing up as
a sexy babe and surfing the Internet with my web cam. I had a lot of fun
fooling some guys and chatting with other crossdressers. I never realized
how many other guys shared my hobby. I got many compliments on my looks. I
really got turned on chatting with the other "girls" and seeing how great
they looked. I found myself jerking off to their images and was spending a
lot of my time looking for "trannie porn" on-line. I happened to find a web
site called Nifty Archive and felt like I had hit the lottery.

*Discovered*
I suppose it was inevitable that I would get caught at my game. It was just
too perfect. All of the free time. The almost unlimited access to clothes,
makeup and shoes. Especially the shoes. I got really comfortable spending
most of each night at work dressed as a woman. I did my job of course. Made
my rounds did my hourly checks mostly dressed as a hot babe. And I came a
lot too. Several times each night in fact. My poor cock was worn out.
Anyway, I suppose I got very careless and a bit too comfortable taking home
my objects of my new attraction. I borrowed (permanently) a lot of stuff and
eventually someone was bound to wonder were all of that stuff was going. On
the fateful night I was making my usual rounds in drag. I was actually
looking really hot. I stopped to admire myself in front of the full length
mirrors and had just pulled out my cock for the first wank of the evening
when a voice form the dark said " Well, ain't that the cutest thing!" I just
about shit in my panties. Out of the dark stepped my supervisor. I tried to
explain, but no words came from my mouth. I am not what I was going to say
as I was caught and I knew it. He said " So, is this how you spend every
night shift?" I could have tried to lie, but instead replied a feeble "Yes.
Pretty much." He then asked " You must have been doing it for a while. You
actually look pretty good." Well that took me by surprise! I was expecting
to get chewed out and fired at the lease and maybe my ass kicked in the
process. He then said " Are you gay?" To which I replied "NO!". He said,
"Well,  I am not so sure. Come over here and let's find out."

What could I do? I walked over to him and he said "On your knees." I
struggle to get off those heels and on my knees. Once there he said "Unzip
my pants."  I did as told and was surprised to find a semi-hard cock in
black nylon panties. I looked up at him and he just smiled. "Pull it out."
he said. I was so so surprised that I pulled out his cock without really
thinking about it. He moaned a bit and said to play with it like he had seen
me doing with my own. I did as told and in no time he was very hard. He
stopped me and unbuckled his pants. As his pants slide to the floor I saw
that he was wearing a garter belt that matched the panties and dark seamed
hose. He pulled of his uniform shirt to reveal a matching bra filled with
latex breasts.  He then said "Let's find me a pair of pumps like yours. I am
sure you know where they are kept." He helped me to my feet and I led him to
the ladies shoe department. I asked him what size and he said size 10. He
sat down and I went into the back and found the right size. I helped him put
on the shoes and then helped him to stand. He walked around a bit with at
very sexy little walk. It was obvious he a lot more practise as I had. He
swayed back over to me and said that obviously I approved of the shoes and
his walk as he reached down and stroked my now hard cock. My attraction to a
sexy walk gets me in trouble all of time! We kissed again and I reached down
and began to stroke his cock as he stoked mine. It only took a moment and he
was cumming in his pretty panties. That is all it took and I came too. He
kissed me again and said "I think I am going to have to spend a lot of time
supervising the night shift at this store." I said that I probably could use
more supervision and smiled. We walked back to the security office and I had
to ask why he came to the store at night. He explained that there had been a
larger than usual amount of women's items missing at the store. After the
last inventory there were many fairly costly  high heeled shoes were
missing, too. The store rarely had high heels shoplifted as only one shoe is
on display while the other shoe is in the stock room. He decided to check
the security camera recordings to see what he could discover. He did not
find too much on the day time disks. Just the occasional suspicious
character, but no repeat offenders and no shoe thieves. For some reason he
checked the night recordings and was totally amazed at what he saw. There
was a woman walking around the store all night and the security guard was no
where in sight. He finally figured out that it was me walking around and
decided to use it to his advantage. He had been an avid crossdresser since
high school and figured there was no way that I could protest as he had
video evidence of me wearing the clothes in the store and wearing out my
cock too. I must admit that I would not have chosen to get caught, but now
am glad that I did. He comes around every night and has become my mentor in
all things feminine. We have had some great times. I am becoming a fairly
proficient cock sucker and we even gone out to a drag bar a few times on my
night off. But that is another story.