jennas first time
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Jenna's First Time free porn video
Jenna's First Time
By Jenna Shannon
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 crossdressers 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 butterflies 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
[email protected] and I will tell you about my first foray
into anal sex, and take you to where I am today.
Huggs!
Jenna
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