Date: Mon, 19 Jul 2004 12:51:16 -0700 (PDT)
From: Jenna Shannon <jenna_shannon2003@yahoo.com>
Subject: Jenna's First Time - TG

This is a true story of my first experience with a man. It happened not
so very long ago and was one of the most amazing nights of my life. The
names have been changed to protect the innocent.

I am a very shy, tall (6' +), slim man with a less than masculine build.
I have enjoyed experimenting with women's clothing for the better part of
my life, and have often had very vivid fantasies involving my feminized
self and very masculine, if not downright hunky men! However, I am
getting a little ahead of myself and really should give you a little
background...

I had a fairly normal upbringing, nothing too out of the ordinary. I
grew up in the suburbs of a medium sized city in Alabama; nice family, a
loving mom and dad, an older brother and a younger sister. Our
neighborhood was quite nice, friendly people, I had plenty of friends,
played all the usual sports that growing boys play, had a part-time job,
all the normal things one might expect from a suburban upbringing in the
late 20th century.

During high school and college, I dated several girls and enjoyed my fair
share of sex like most other guys my age. You might say that I was the
All-American Male, except for one minor detail. I had a proclivity for
wearing women's clothing, anything soft and silky, sheer and pretty was a
huge turn-on for me. Like most young and budding crossdresser's I
couldn't get enough of pretty, sexy panties, pantyhose, stockings, slips,
bras, skirts, etc., you name it and I wanted it to feel it against my
body. The feelings associated with dressing in something feminine was
absolutely divine, and anytime I could get a few moments alone I was
dressing up and feeling sexy. Typically these little forays with my
girlie self concluded with a little clitty teasing that were ripe with
fantasies of sex with cute boys or handsome men until I would erupt with
torrents of warm, gooey cum all over my belly and chest.

Also, like many young crossdressers, especially us GRITS (Girlie-boys
Raised in the South) by relatively religious parents, I would go through
periods where I felt terrible guilt (due to my faggot desires) and purge
whatever small stash of pretty, feminine attire I might have
accumulated. I also had my fair share of "close calls" when someone
would come home unexpectedly and nearly catch me being a cute little
sissy!

When I went away to college I had a little more freedom to explore my
desires to be a girl, but still not what I would have liked - since I did
chose a southern university where a lot of people I grew up with
attended. When I did find the time it was bliss!

Right after college I met and fell in love with the woman I would marry.
We were very happy for a short time, and then she decided to play the
field a little too carelessly and I found out. We tried to work things
out, but to no avail and after four years we divorced. While I didn't
completely stop dressing during our time together I could count on one
hand the number of times I was really able to bring Jenna out.

Shortly after our divorce, once again living in my hometown city I began
to amass a beautiful feminine wardrobe, and every night I would get home
from work let Jenna out of her closet, so to speak, and be free to pursue
my feminine desires. I still had friends but found myself wanting to
spend more and more time alone - as Jenna. Also, my fantasies involving
a very feminized me, and a really cute guy intensified.

At this time I also started seeking others with similar interests via the
internet, both other girls like me and our admirers. And this brings me
current in the story. One night I met a man named Charlie in a local
chat room online. We hit it off really well, and he knew just what to
say to make me feel pretty and wanted. After several weeks of chatting
and several pictures had been swapped, Charlie told me would like to get
together. This was what I had been waiting for, a man that wanted me as
Jenna! I was extremely flattered, but also very nervous, I knew I didn't
want to give out my locale just in case he wanted more than I could
give. Well, Charlie solved that dilemma by inviting me over to his
place, but he said I had to arrive as Jenna! What I get pulled over on
the drive over? What if my car breaks down? What if someone reads me?

Charlie assured me that everything would be okay, nothing would happen
and no one would discover my secret since I am quite passable as long as
I am sitting down. Once I stand up, however, it is easy to tell what I
am - a sissy boy! We finally agreed on a Friday night that was
convenient to the both of us, and Charlie asked me to wear something
special for our first night.

Finally, after what seemed like forever the day finally arrived. I left
work a little early because I wanted everything to be perfect. On the
way home I stopped by the mall and did a little last minute shopping. I
bought some more foundation - MAC, a girlie's best friend, A bottle of
BEAUTIFUL perfume (my ex-wife's favorite - go figure!), and a bra and
panty set complete with garter belt and stockings from Victoria's Secret,
all in virginal white. I went home unloaded the car and went inside to
get ready.

I took a long hot bubble bath and shaved everywhere, except for a cute
little patch of trimmed hair just above my clitty. I soaked in the tub
for a quite a while to allow my skin to become as soft as possible and
then put a nice creamy cocoa butter lotion on all over. I put on a cute
little kimono and began to get ready. First I did my makeup, foundation
powder, a little pink blush, lavender, pink and silver shadow, full thick
(FAKE!) lashes, a pretty, soft pink lipstick with two coats of shiny lip
gloss and voila! My face was ready, next I donned a shoulder length
brunette wig (my natural color). And when I looked at the completed
product in the mirror I was very satisfied.

Next I painted my toes with two coats of pink polish to match my lips,
then came the silky, shimmery thigh-hi stockings, donned the gorgeous
white garter-belt and attached the garters. I slid into the delicious
satin Body By Victoria boyshorts (seemed rather fitting - giggle),
fastened the matching Body By Victoria full coverage bra and inserted my
very realistic breast forms and the foundation was complete. I had
chosen a gorgeous pink chiffon dress that fell to just above the knee, it
had cute puffy sleeves and pretty ruffled trim. I sat back down at my
bureau and attached my nails and applied another two coats of the same
pretty pink polish as my toes. I chose simple jewelry a dainty chain
with heart shaped pendant for my neck, a pretty heart shaped watch and a
simple silver chain for my other wrist, a couple of rings and I was
almost ready. I slipped my feet into a pair of beautiful, pink anklewrap
sandals with a four inch heel (nothing quite like a tall girl!), applied
my new perfume to all the right places and I was feeling sexier than I
ever had before. I slipped a few essentials into a cute pink clutch,
packed a little maribou trimmed babydoll, with a few day clothes (who
knows, right girls?) and I was ready for my destiny!

I called Charlie when I was ready and told him I would be right over, he
told me the door would be unlocked and to just come right in. With
trepidation I went into my garage, climbed into my car and hit the
electric door opener. I backed nervously out of my drive and started the
journey to Charlie's house and my first night as a true sissy!

When I got to Charlie's I took a few deep breaths, slid my legs out of
the car and stood up, the butterfly's in my tummy were unbelievable. I
minced my way up his walk, placed my pretty hand on the door knob and
opened his front door. Charlie greeted me in the hallway with a dozen
yellow roses and a sweet hug. Now, Charlie is considerably shorter than
I, especially in my four inch heels and I absolutely LOVED it!

"WOW! You are gorgeous!," Charlie said.

"Blushingly, I replied, "Thank you, you are rather dashing yourself!"

He led me into his den and poured us both a glass of wine. "To a
wonderful evening!" Charlie toasted.

We drank several glasses of wine, and talked for quite a while. We
talked about my desires, the fact that I had never been with a man and
Charlie told me how honored he was to be my first. He was such a
gentlemen and felt very relaxed, he ordered in some Chinese food and we
ate. After dinner while drinking more wine, Charlie put on some soft
music and we snuggled up with one another on the couch. When Charlie
finally kissed me it was the most electric moment of my life. His strong
lips pressing against mine, his tongue pushing its way into my mouth, me
willingly succumbing to him, while emitting a soft, feminine moan. I
knew I would give myself to him this night, and I could not wait.

Charlie rose and led me into his bedroom, it was very simple and very
masculine and felt like the most appropriate place in the world for me to
finally become a sissy. Charlie removed his shirt and I got my first
look and his hairy and very manly paunch. Next Charlie removed his shoes
and socks but left his pants on!

"You will have to take off everything else to get at what you want," he
teased.

Smiling I knelt before him, running my hands all over his chest and
stomach. I leaned forward and kissed him on his stomach, basking in his
scent. I lowered myself onto my bottom, with my legs to one side and ran
my hands down his stomach and over the bulge in his pants.

"Mmmmmmmm," I moaned.

"Do you like that?" he asked.

"It feels wonderful," I replied, smiling up at him and licking my lips.

I undid his belt and pants button, then slowly slid the zipper down. I
pushed his pants to the floor and helped Charlie step out of them. There
he stood his masculine hairy legs and stomach framed his white cotton
briefs. He looked good enough to eat and that is exactly what I intended
to do! Leaning forward I went to kiss his bulge, when he moved just out
of reach.

Smiling at me he said, "Look at you! A sissy boy desperate to get at my
cock! Do you feel like a little faggot, Jenna?"

"Oh yes!" I cooed, "I am a little sissy, faggot and I so badly want your
cock!"

"Kiss it!: he demanded. Which I readily did. Would you like to set it
free, I nodded my head yes, moaning with desire, as he instructed me
slide his briefs down his hairy thighs. I did as instructed and then
asked if I could touch it.

"Of course, baby," Charlie smiled. Wrapping my fingers around his hard,
7.5 inch cock was electrifying. "What would you like now, Jenna?"

"Mmmmmmm, I wanna be a cocksucker!" I moaned, as I leaned in a flicked my
tongue across the head of his cock.

"Oh, Jenna, " Charlie admonished, "You've always been a cocksucker, you
just never had a cock before. You were meant to be a little sissy and
you realize that, you weren't made into a faggot, you were born a
faggot."

I stared into his eyes, mesmerized as his cock rubbed against my lips. "
A real man would never dress the way you do and beg to be a cocksucker.
Only a little prissy fairy would act like you, now open your mouth and
welcome what a man like myself has to offer you, Jenna." I willingly
parted my lips and allowed Charlie to slide his cock into my mouth.

"Mmmmmm, that's feels so good baby, you like it don't you?" I nodded my
agreement unable to speak with my mouth so full. "This first time will
be pretty quick Jenna because I have been saving myself for you tonight.
But we will have plenty of time for you to get me hard and have sex all
night long, ok?"

Whimpering with delight I shook my head yes. Charlie pulled his cock out
of my mouth and began to stroke himself. "Would you like for me to cum
for you? Cum on you?" Charlie inquired.

"Oh yes baby! Cum for Jenna! Cum on Jenna! I want to feel your hot,
gooey load! I want to taste you!" I screamed.

After a few more strokes Charlie's cock began to twitch and then thick,
globs of cum shot out from the slit, splashing onto my tongue, up my
nose, across my cheeks and chin. "Mmmmmmmmm!" I groaned.

"You like that baby? Are you a real cocksucking faggot, now?" Charlie
teased as he rubbed his cock on my face smearing his cum everywhere.

"Oh, yeah baby! I'm your cocksucking, cum eating, little sissy!" I
cooed.

Smiling down at me Charlie exclaimed, "I can't wait to take your virgin
ass in just a little while!"

I smiled and moaned, wagging my pantied bottom in anticipation of my
imminent deflowering by this gorgeous man!

If you like the story so far, please email at
mailto:jenna_shannon2003@yahoo.com and I will tell you about my first
foray into anal sex, and take you to where I am today.

Huggs!

Jenna