Date: Wed, 24 Mar 2004 08:26:27 -0500
From: Elaine Rice <ilovecrossdressing@hotmail.com>
Subject: Tales of a Crossdresser-Chapter 1

     This is a tale of the escapades that have happened in my teen years
that are all but unbelievable. I advise you that there is strong sexual
content, and the following stories involve sex with crossdressing, multi
generational relationships, lesbianism, bisexuals, and orgies. The names
have all been changed to protect the promiscuous. Please turn back if this
is not something you care to read.

     The first I must say is that I have been urged by sex and pornography
for some time now and it all started when I was about thirteen. I found some
lingerie of my stepmother's and decided to try it on. I can't remember why I
wanted to do it, I just know that it felt right, and I believed in my heart
that there is nothing wrong with clothes. They are simply fabrics stitched,
woven, and embroidered a certain way to reveal and cover different areas of
the human body.

     The first outfit I found was in a black garbage bag in the downstairs
closet of my stepmother's house. It was a silk black Basque with red lace
trim, black thigh high fishnets, and matching panties.

     I dressed up in the bathroom and stood in the mirror. I was so shocked
at how revealing it was, and I felt stirring feelings in my body. I felt
sexy, or, at least as sexy as any thirteen year old Italian boy can feel
looking at himself.

     I couldn't believe that my stepmother was getting rid of this! If she
was getting rid of this sexy outfit, then there had to be more in that huge
bag, as it was filled to the brim with clothes. I quickly undressed and
stashed the clothes in my overnight bag. Later that night, I sorted through
that bag and found a red and white striped G-string and four dresses that
felt really silky. A week later, I took a white knee length slip from the
laundry hamper and took it home.

     My bedroom in both my mother and my father's houses was in the
basement, so I was granted quite a bit of privacy. I locked my bedroom door,
and dressed up. I put on the g-string, the white slip, then the dress, which
was awkward, it had to zip up the ass and it was a tight pencil skirt. I
could see why women sometimes hated getting dressed up. Unless you have
never tried it, don't complain why it takes them so long.

     Anyway, I stood in front of my two full length mirrors set at two
corners of my room. Damn, did this look hot! My cock began to swell, and I
began rubbing it through the silky fabrics. The next thing I know, I have my
hand up my skirt, rubbing myself through the slip and g-string. I didn't
know what I was doing; I just knew that it felt good.

     After rubbing myself for a while, I was overwhelmed with the sensation
of a strong tingling in my loins. I couldn't touch my cock anymore, it was
way too sensitive. I just kept still, on my knees on my bed, dressed in my
stepmother's clothes, shivering with orgasm.

     After the tingling subsided, I shakily undressed and folded everything
up. I noticed a little wet spot on the slip, and couldn't at that time
figure out why.

     The next day at school, all I could think about was the clothes at
home. I promised myself that I would dress up in the black Basque that
night. About ten O'clock, the door got locked, the outfit went on, fishnets
and all and the rubbing became a pulling movement with the off-white slip.
Wow, did this feel good. I went frantically at it until the tingling
overwhelmed me again. After shaking from orgasm, I looked at the slip, and
low and behold, there was another wet spot the size of a dime.

     That night, I figured that it must be what happens when guys have sex
they leak out sticky sperm. I asked a few friends in school about it and
they said I was right. I never in a million years though told them about my
outfits or the fun I was having in them.

     This went on for months, and after some time the dresses began to get
sweaty from me, and the slip was beginning to get stained from my fluids, so
I had to wash them.

     A while later I became bolder in my desire for outfits and lingerie. I
began to go through Elaine's closets and drawers and take a thing or two
home to try out. I took my first pair of pantyhose from her about a month
after I took the first outfit in the downstairs closet. I began to
accumulate a bit of a collection from her. I had thigh high stockings,
dresses, Basques, corsets, camisoles, baby doll tops, silk panties, and silk
slips.

     I kept them in a huge book-bag in my closet. I began to take more than
I should, although, I was loving every minute of it. I would save up my
allowance money and buy Polaroid instant film packs. I got dressed up in
Elaine's outfits while they were out of the house and would stand in front
of her dressing mirrors and pose for the camera. I would take as many
combinations of clothing dressed up as I could. My slender teenage boy body
was easily mistaken for a girl's. I would pad the cups of the bras I wore to
look more like a girl. My skinny waist, small butt, and curvy legs looked
really inviting in filthy lingerie, and I captured every moment of it.

     I took pictures of Elaine's vibrator in my mouth, and her Ben-Wa balls
in my mouth. I began to stir a very urgent need to have sex with her. She
was adorable to me, and I knew why my father liked her so much. I'm sure any
lady who looked as hot as she did, and could dress up in slutty lingerie for
three months and never wear the same outfit twice would certainly stir the
needs any man had to fuck.

     At the time, I began to find my father's porn videos and adult
magazines. I also came across two photos of Elaine naked at a nude beach.
They evidently were taken while her and my father were on vacation
somewhere. I studied every inch of her naked body. She is about 5 foot 5
inches, 130 pounds, she was very shaved down below, all except for a V
shaped patch above her pussy, and her breasts were almost too big for her
body. I later found her bra size was 38D, which are huge to anyone's
standards, let alone a 13 year old boy, although breasts have never been a
turn on for me.

     For two years, I did nothing but jerk off on all Elaine's outfits
thinking of nothing but her. I dreamt of all the things I would do to her if
I had the chance. I knew I was sick in thinking of my stepmother as a sex
object, but I couldn't help myself.

     One evening, I hit the Jackpot. I came across a camcorder video stuffed
way in the back of the top of her closet. I knew it had to be back there for
a reason. I couldn't wait to find out what was on it. I practically raced
through the house, downstairs to the game room and found the VCR adaptor
cassette the video fit inside to watch it. I rewound the entire tape and sat
there literally shaking from nerves of anticipation and watched the tape
from the beginning. As soon as I hit play, I heard my father pulling down
the gravel driveway. Nearly having heart failure, I straightened up my
clothes scattered out to fuck in and put them away a few seconds before they
walked in.

     I had to wait until I got back to my mother's house to watch the
mysterious video. With a locked room, a blue silk camisole set, and white
thigh highs on. I sat there on my bed and hit play. The video came on and I
immediately noticed the room was my room at my father's house. The sleeper
sofa was folded out and I see my father lying on the bed naked. It was kind
of disturbing seeing my dad naked, although he's by far not unfit. He
doesn't even have a belly on him.

     He lied on his back and a few seconds later, I watch Elaine walk into
the viewing area. She was wearing an emerald green and black trim silk
teddy. She had a matching transparent robe on, and stay up thigh highs. I
knew the outfit well. I wore that outfit many times and if I didn't see it
so much in the hamper, I would've taken it knowing that suspicions would not
be roused.

     What I watched was a three hour video of my stepmother fucking the shit
out of my father. They fucked doggie style, missionary, cowgirl, reverse
cowgirl, spooning, you name it. She moaned and screamed out orgasms every
few minutes. Elaine went through several costume changes during the sex.

     The first orgasm my father had was in Elaine's mouth as she
deep-throated him. His second orgasm, she rode out of him cowgirl style and
they came together. The next scene on that video was what really opened a
lot of questions and answered a lot of questions all in the same breath.

     The next scene was in a different room, and it wasn't my stepmother's
house. After fast forwarding a few moments, I watch my father making out
with another woman in a huge master bedroom. Then, Elaine comes in with
another man and he goes down on her next to my father. The other couple was
close friends of my father and mother when they were still married. There
names were Doug and Bernadette, but everyone called her Bernie.

     Bernie was a gorgeous short Italian hottie in her early forties with a
slender body, full breasts, long Indian black straight hair, and deep tan
skin. Doug was a  physical fitness fanatic that worked in heavy construction
all year round, about 6 years Bernie's junior. I could understand why Elaine
was interested in him, as I watched him eagerly work a meaty rod in and out
of her silky slit. My father fucked Bernie for a few moments missionary
style until she pushed him down and rode the shit out of him.

     Bernie really caught my desires and attention because she talked really
dirty. She was really vocal in her moans and yelled out words of
encouragement as she was fucking and being fucked. They switched partners
again, and positions, and ended with Bernie and Elaine eating each other's
creamy selves after my father painted Bernie's flat abs with sauce, and Doug
painted Elaine's face with a gooey mess.

     I couldn't take anymore, I was jerking myself so fast on my bed that
when I came, I spurted the biggest load of cum that I ever saw release from
my loins. I was leaning back a bit on the bed and the sticky stream jetted
straight up my chest and painted a hot fluid stripe up my blue silk top and
ended at my throat. The next few spurts raced out onto my stomach. The cum
was really warm, much warmer than I ever would have guessed, as this was the
first time I came all over myself. I usually finished in a pile of silk
clothes, or occasionally on my hand, but never on myself.

     I made a copy of the video to keep with my collection, and returned the
original to its hiding place. So, the truth be told, my stepmother was into
other guys...their monogamous act was only to fool everyone else from finding
out the truth... The truth that I now know... The question remained...could I
finally get to fuck her?


Chapter 2 to follow...