Date: Sat, 17 Jul 2010 23:18:02 -0400
From: cybereena <cybereena@gmail.com>
Subject: Trannie in Training 2

Here is the long awaited second installment to my little story. Thanks for
all of the nice comments and encouragement from your readers. Love ya!
***************************************************************************

*Caught Again*

Things have been great since I started my new job and secret life as a
crossdresser. I have had a lot of experience dressing and actually passing
on the street as a woman. Actually a very sexy woman at that. The visits
from my supervisor were always memorable and he has taught me so much about
looking and acting like a woman that I felt very confident that no one could
possible know that this sexy lady had a little extra surprise in her pretty
panties. Like I said, things were going good. Maybe too good. Our company
contracts with the department store to provide security services. Retail
stores have been hit pretty hard with the economy being the way it is. One
of the cost cutting measures was to do away with store security and rely on
alarm systems and security cameras instead of guards. Great! Not only was
out of a job, but no longer had access to all of things that made me so
happy. I did have a large stash of every imaginable item of feminine attire
in my room at my apartment so I was not going go without plenty to wear. It
was pretty depressing none the less to think that I may have to get a day
job and wear male clothes most of the time. Little did I know how difficult
finding another job of any kind was going to be? I spent every day searching
the want ads, sending out resumes, and generally being miserable. Have you
ever seen day time TV? OMG! After several weeks of this I could not stand it
any longer. After my roommate left for work I pulled out my pretty stuff
from its hiding place and started my transformation. I had all day so
decided to really do it right. Scented bath. Shave all over. Scented lotion.
I pulled on my panties and filled my matching bra with my silicone fake
tits. Garter belt, seamed stockings, and a waist cincher. That cincher
really gives me a great feminine shape. I sat down at my computer desk with
my make up bag and mirror. I have become quite adept at applying make up and
can change my look at will. I went for a rather slutty look on that day. Too
much eye make up and even some false eyelashes. Glossy red lips and I was
done. I carefully pulled on my tight black mini dress so as not to disturb
the make up artistry. A long curly platinum blond wig and I am really
turning myself on. Silver earrings, a dozen thin silver bracelets, and a
simple silver necklace.  I saved the shoes for last. Six inch red patent
platform stilettos with little ankle straps. By now I am almost breathless
with excitement. I stand and walk over to the full length mirror and get
that old familiar feeling. I want to play with my hard cock so badly, but I
have all day. I want this to last for a while. I try and watch TV, but
cannot keep my mind on any of the shows. I decide to check out the Internet.
I have some favorite tranny and shemale porn sites so I surf to one then the
other looking for something new that I have not seen a hundred times before.
No luck. Nothing new in porn town. I am now about to give up when I see a
link on one of the sites that says live chat room. I have been in chat rooms
many times and I find them pretty lame, but at least it has got to better
then Oprah and friends. The chat room opens and I am immediately bombarded
by bots trying to get me to surf to this porn site or that. There a few
other live people in the room and I have a conversation with a few of them.
Mostly foreign guys I think based on the way they talk. I then strike up a
conversation with someone named Lucy that claims to be a crossdresser who is
dressed and is also bored. I have heard this before. We chat for a while
about what we are wearing and the fact that chat rooms pretty much suck. She
asks if I have a web cam and well yes I do. So? "You want to cam with me?"
Lucy says. I am a little afraid of this idea as I really do not know who
"Lucy" is, but I am willing to risk it. The web cam application opens and I
see Lucy for the first time. Not bad! I can tell that this is a guy in drag,
but not really that unattractive. Lucy is all compliments about my
appearance and wants to know if I am not really a woman pretending to be a
man in drag. I assure her that I am not. We cam for a little while and Lucy
asks if I want to see her cock. She says she will show me hers if I will
show her mine. How cute! By now I am pretty comfortable with Lucy so I say
OK. She moves her cam down so I can see her skirt. She raises her skirt up
and there is a hard cock straining to get out of her nylon panties. She
slides the panties down and her cock pops free. She strokes it a little and
I can hear her moan softly. She says "Your turn." My dress is rather tight
so I have squirm a bit to get in a position to get my cock out of my
panties. I adjust the camera and begin a slow tease as I raise my skirt and
reveal my panties. Lucy comments that my panties are so beautiful and I tell
her that they are real silk just to make her more jealous. I stroke my cock
through the panties and my god it feels good. It is not going to take much
to make me cum. Lucy is stroking her hard cock in earnest now and I pull
mine out and begin slowly stroking the length of it. I slowly pull the
foreskin over the head and back again. Lucy and I go at this for a short
time and I see her cock tense and begin to spurt strings of white cum. I am
so turned on! I feel a huge orgasm building and just as I am about to cum I
hear "Hey! Who are you? What are you doing in my apartment?!" from behind
me. I am too far gone and send jets of cum on to my keyboard and monitor. I
am trying to put my cock away and hide my face and would have pulled the
carpet over my head if I could have managed it. Lucy quickly logged off and
there I am in full drag, cock in hand, cum sprayed all about, and my room
mate staring at me in disbelief. So what do you say at a time like this? The
only thing that I could manage to say was "I was bored." How lame was that?
My room mate starts laughing. In fact almost falls on the floor he is
laughing so hard. I realize what I said and have to start laughing myself.
When we both have settle down a bit he says, "I would never have know that
it was you. You absolutely look like a woman. Except for that..."as he
points to my now limp cock. He asks how long I have been dressing a girl. I
say that it all started fairly recently. He said that he forgot his
briefcase, so had to come home. He has a meeting that he has to go to, but
that we need to discuss this further when he comes home. He says, "I hope
that you are dressed when I get home." I am dumbfounded. All I can manage is
a weak, "OK." He grabs his case and as he is leaving says "Damn, you look
sexy!"

*The Arrangement*

After my room mate left I was not sure what to do. Everything happened so
quickly that I was not sure it really happened at all. I got up from my
chair, arranged my cock in my panties then cleaned off the monitor and key
board. I took off my clothes and make up and put on my male stuff and went
for a walk to clear my head. I walked in the park and was enjoying the nice
weather and thinking what it would be like to walk in the park in my high
heels. I was rocked from my daydreams by my cell phone ringtone. Hoping that
it was a job offer I hurriedly grabbed the phone and said hello. It was my
room mate calling. He said that he was not kidding about what he said about
when he got home. He definitely wanted to see more of my female alter-ego.
Well, that confirmed the fact that it was no dream. I headed for home and
thought about what to wear. I didn't want to over do it and look like a
total slut or some drag queen. After all I do live with this guy. Or at
least hope that I would. I decided on a nice dress, modest heels, and what I
seen called "day makeup" in the women's magazines. I have one dress that is
very elegant. It was a designer model that would have cost a fortune if I
had to pay for it. I do not own any modest underwear, so matching silk bra
and panties set with garters and stockings was the choice also as I do not
own any pantyhose. I finished up in time to relax a little and poured myself
some wine. Right on time he was home. I stood up to greet him and all he
could say was "wow".  He told me to turn around with I did with ease in
flats. He I took me by the hand and led me to the sofa where we sat. He said
"So, tell me how long this has been going on. Did you start when you were a
kid or a teenager? What sort of things do you wear? Do you ever go out
dressed? Are you gay or transsexual?" I said "Whoa! You have a million
questions. Would you like a glass of wine? I know I do." He said yes, so I
refilled my glass and poured him one. I tried my best to answer his
questions. If you have read the other parts of this story you already know
the answers. When we had finished the wine, he said "Let's go out to
dinner." I was shocked. I told him there was no way I could do that. He
reassured me that no one could possibly know I was not a pretty girl. After
a few more compliments I gave in. We had dinner and more drinks. I was a bit
intoxicated by the time we returned to the apartment. He unlocked the door
and as I started to enter he turned and kissed me. I have never kissed a man
before, but I really liked it. I turned to him and kissed him back. Before
long we were making out like teenagers. I said we better go inside before
one of the neighbors sees us. We went to the couch and before you know it he
was out of his clothes. I was in my bra and panties. He was kissing my neck
and chest and belly and thighs. I did not stop him until he got to my
panties. I said "you know what you are going to find in those panties don't
you?" He replied "Yes" and started rub my hard cock through the silky
material. I began to kiss his face and neck. Then I moved to his hard
nipples and he let out a low moan. I asked if I had hurt him. He said that
no one had ever sucked his nipples before and he liked it. I alternated
gently biting and sucking them while stroking his cock. I felt his cock
tense and he began shooting cum on the leather sofa. After he stopped he
pulled down my panties and kissed my cock. He began to suck and lick and
stroke me until I was cumming too. When we had regained some composure he
asked if he had done OK. I said my god yes. Where did you learn to suck
cock? He said that this was his first time, but he hoped not his last. I
agreed. We both cleaned up and he asked me to come and sleep in his bed. I
went an got my sexy baby doll nightie and crawled in beside him. As I lay on
his shoulder he asked how my job search was coming. I told him not to ruin
the moment with talk about my lack of a job. He said that in the meeting
that he had this afternoon that he had gotten a promotion and a large raise.
He said suppose that I stop looking for a job and become his live in girl
friend. I as floored! It actually sounded great. I could dress and live as a
woman and give my full attention to this man. I quickly agreed to the
arrangement and he kissed me. I went to sleep in his arms. A new and
wonderful life was beginning for me and I am sure the happy smile on my
sleeping face showed it.