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Nifty - Transgender - Teen - My First Time Crossdressing - My First Time Crossdressing 1

 
Date: Mon, 22 Mar 2004 17:53:21 -0800 (PST)
From: Dan R <vtcarfanatic@yahoo.com>
Subject: My first time crossdressing part 1

My first time crossdressing
By Danielle Reilly


THIS IS A COMPLETELY TRUE STORY OF MY FIRST TIME CROSSDRESSING

A quick background

       Growing up I'd always been fascinated by
women's clothing. Seeing a girls smooth legs
peeking out from under a skirt, accentuated by her
high heels was just a huge turn on for me. Since
then I've always loved women's lower bodies. The
skirts, panties, hose, and high heels that they
wear are my favorite things in life.

When I was 11 I began to investigate some of my
mothers clothing, rifling through her silky
panties, bras and pantyhose I experienced my first
erection, though at the time I didn't really know
what it was. After a few months of just exploring
her underthings, I began to try them on while the
family was away. Because I went to a private
school, I got out of school at 2:30 in the
afternoon and my mother worked at the public high
school she wasn't home with my younger sister until
4, and my father wasn't home until 6, so I had
plenty of time to explore my feminine side.

When I was 13 I experienced my first orgasm,
while washing myself in the shower. After that, I
just couldn't get enough, and masturbated at least
4 times a week. It was also around this time I
began trying on some of my mother's panties and
hose, and luckily for me my mother and I were the
same size at this point in our lives. After I
turned 14 my parents told me that they were going
on vacation to Florida in the summer, and asked if
I wanted to go with them. Of course seeing the
opportunity to spend 10 days home alone I said no.

The First Day

       Finally June came around, and the day of their
departure came after several sleepless nights of
excitement. After watching my parents drive down
our driveway (which was a long one in full view of
the house), and waiting long enough to be sure they
wouldn't be coming back to get something they
forgot, I ran across the house towards my parents
bedroom, and more importantly my mothers closet,
stripping off my clothing as I went.

       For a while I had been planning for this week
alone, and knew exactly what I wanted to do. I'd
even let my hair grow for the past 3 months so that
I would have semi long hair at the time.

       Heading into her bedroom I quickly raided the
closet. I pulled out her purple minidress. I'd
only seen her wear it once at a party, but I loved
it. It was purple velvet (or something like it),
with low cut shoulders and front. It was a tight
dress and hugged curves, and ended at mid-thigh. I
also pulled out from the bottom or her closet her
pair of 4" black stiletto heels. Moving over to
her dresser, I quickly selected a black wonderbra,
tight black lace panties, and a pair of black thigh
high stockings.

       I quickly hopped in the shower and washed my
hair and body quickly. Being only 14 I didn't have
much body hair, but I went over my body quickly
with my moms razor until I was completely hairless.
Hopping out of shower I wrapped my towel around my
chest like I had seen my mom do a hundred times. I
spent extra time in the mirror making sure my face
was completely hairless. Staying at the mirror, I
opened my mom's makeup case and began to
experiment. I brushed a small amount of mascara to
my eyes, followed by some blue eyeshadow and a
small amount of blush to my cheeks. Finially I
applied some bright red lipstick to my lips.
Looking in the mirror I was surprised to see the
face a slightly older girl looking back at me. I
puckered my lips, and then moved back to the bed in
my mom's room where my clothing was waiting.

       I quickly pulled the lacy bra out of the pile
and wrapped it around my chest. Clipping it in the
front, I rotated it around and slipped my arms
through the straps. After adjusting the length of
the straps slightly (my mother and I were about the
same size after all), I filled the cups with some
flesh colored nylons from the dresser. Grabbing
the panties from the bed, I slinked them up my
hairless legs, relishing the feeling of the lacy
material and it caressed my skin.

       Sitting back on the bed, I balled up the nylons
and slinked them up my legs, snapping them tight
around my thighs. Slipping my feet into the high
heels I stood and quickly wobbled back down on the
bed. Slowly I stood back up and took several laps
of the house, getting used to walking in the heels.
After about 10 minutes I felt comfortable enough in
the heels, but I was experiencing another problem.

       The feel of the lacy panties was driving my
cock nuts, and my raging erection was poking out
the top of the panties. Headed to the bathroom, I
loved the way that my legs and butt felt in the
high heels. The feeling of the lace panties and
hose on my skin, and the way my legs looked in the
heels was turning me on more than I'd ever been.

       In the bathroom I quickly pulled my panties to
the side allowing my cock to spring free. The head
of my uncircumcised penis was dripping precum like
it was water, and I noticed it had actually made a
small stain on the front of the panties. Grabbing
a quick handful of toilet paper and teetering on my
heels, I quickly began to stroke my aching prick.
After only a few strokes I felt my orgasm building,
and I felt my knees buckle as it hit. Falling to
my knees I watched my hot cum spurt right through
the handful of tissues and into the palm of my
hand. Regaining my composure, I dumped the tissue
paper into the toilet and quickly washed my hand,
though the hot cum on my hand had intrigued me. I
tucked my now flaccid penis back between my legs
and was pleased to see the flat front on the
panties.

       Back in the bedroom, I quickly slipped into the
dress and zipped the back. Looking in the full-
length mirror on the wall, I saw a sexy young girl
looking back and me and was pleased with the way I
looked. I took the next 20 or 30 minutes to look
through my mother closet for things I may have
missed earlier, and found a blouse and skirt I
wanted to try on later, as well as some silk
camisoles that I would try on too. Under one of
the camisoles in the drawer, I also found a tube of
KY.

       Deciding that I would spend the next 9 or 10
days as a girl, I poured myself a glass of juice
and, still practicing walking in the heels, went to
the living room. Logging onto the Internet, I
quickly checked my email, nothing new, and then
began surfing the web looking for sites about
dressing as a girl.

       After looking quickly at some websites of some
beautiful t-girls, I stumbled into the nifty
transgendered stories archives. I spent the next 5
to 6 hours reading stories about other people
dressing as girls, living as girls, and what really
peeked my interest were the stores of the people
having sex as a girl. Downloading several of my
favorites to the computer, I logged off the net.
By this point I was extremely horny again, but I
was determined to experiment more. After rereading
a couple of the stories that contained detailed
descriptions of their sexual experiences, I wanted
to try some of them for myself.

       Making my way around the house, I quickly
locked the doors and closed all the blinds,
ensuring that some unsuspecting person would not
catch me. Wanting to feel more feminine than I
already felt, I decided that I wanted to experience
sex in the female sense. Considering what I had
read in the stories, I decided that anal sex was
something that I wanted to try. Knowing that it
would be difficult the first time, I ran back to my
mother's bedroom and grabbed the tube of KY from
her dresser.

       I decided that my bedroom would be the best
place for me to try it, just because I felt more
comfortable there. Feeling very horny and wanting
to have the best experience possible, I decided to
stay dressed as much as possible. Slipping my
panties down my legs, I kicked them off and they
landed on the bed. I began to root through my desk
drawers looking for something to use, and in the
back of one of the drawers I found a .50 caliber
bullet that I had bought several years earlier. It
was roughly the same size and shape and my penis,
and it seemed like the perfect substitute. I
dropped a towel onto my bed to keep from making a
mess on my comforter, and stood next to the bed. I
Spread my legs wide and hiked the dress up and over
my hips like I'd seen so many girls in pictures do,
and bent forward over the bed. I could feel my ass
check pull apart and the cool air of my house
caress my rosebud. I was glad I'd chosen to shave
my butt and clean my ass thoroughly inside and out
while I was in the shower.

       Spreading a generous amount of the KY onto my
fingers, I felt a chill run up my back as I spread
the cold gel onto my hole. Applying more gel to my
hand, I bit my lip as I pushed my middle finger
into my ass. It slipped in surprisingly easier
than I thought, and didn't hurt at all. Sliding my
middle finger in and out I applied even more KY to
my fingers, lubricating my ass thoroughly inside
and out. Soon my hole felt loose enough that my
finger was easily moving, and I slipped in a
second, and as it loosened even more a third.

       As I moved my fingers in and out I relished in
the feelings I was having, and wanted something
bigger. As I removed my fingers my ass felt empty,
and I just had to have something in it. I spread
more KY onto the cold bullet and placed the tip
against my hole. The cold sent another shiver up
my back but I needed it. Pushing in I felt my
sphincter stretch to accommodate it, and I loved
it. Quickly I felt the tip of it slide against my
prostate, and I thought my dick was going to
explode. It pulsated and I could feel cum moving
upwards in my hard shaft. My right arm, holding me
up on the bed, almost collapsed as the feeling
washed over me.

       Unsure of what just happened, but knowing it
was good, I slowly retracted the bullet and pushed
it back in, again hitting my prostate and sending
the feeling through me. Starting slowly I began to
fuck myself with my artificial cock. Moving it
faster and Faster, I could feel the beginnings of
my orgasm and I had yet to touch my hard cock. I
moaned out loud as I fucked my ass, rocking back
and forth on my high heels in rhythm with my
fucking. Looking down onto the bed I say my
panties bunched up on the bed, and I picked them
up, replacing my hand with my elbow and bringing
them to my nose. I could smell my precum on them
and noticed a wet spot on the front where my cock
had rested, and extending my tongue I tasted it.
It tasted very good and I knew I wanted more, but
at the time I was too busy fucking myself to do
anything about it.

       All too soon I felt my orgasm coming, and with
a loud moan I felt my cock swell and explode my hot
sticky cum onto the towel. My sphincter tightened
around the bullet and my entire body pulsed as my
orgasm washed over me.

       I lost track of time briefly and I don't know I
long I stood there, bent over the bed with my ass
in the air like a slut, cum dripping from my now
flaccid cock, but after what seemed like forever I
felt the bullet slip out of my well-fucked ass and
fall to the floor. Still bent over the bed, I
picked up the towel and wiped the dripping cum from
my prick, then wiped the KY from my ass.
Straightening up I slipping my nylon-clad legs back
into the panties and pulled them up around my
waste, and wiggling my hips settled the dress back
into place.

       After sitting on the bed for several minutes
recovering, I went to the kitchen and quickly made
myself a small bowl of soup (I hadn't eaten all day
and needed to keep my strength up). Settling on
the couch, I crossed my legs and slowly ate my
soup, watching Ally McBeal or some other very
feminine show (I can't remember now what it was).

       After the show I decided it was time for bed,
as it was about 11 at night and I had a lot more
plans for the week. Heading back into the
bathroom, I washed off my makeup and headed into my
mother's room again. Slipping off the dress, I
laid it out on the bed neatly, and then opened the
drawer in her dresser containing her nighties. I
selected quickly a white silk camisole with pink
flowers and matching panties. I slipped my feet
out of the heels, and slipped the stockings off my
legs. After unclipping the bra I slid the panties
down my legs, and picked up the white bikini cut
silk panties. Sliding them up my legs, I squirted
some aloe into my hand from a bedside pump and
quickly applied it to my smooth legs, keeping them
soft and smooth. I slipped the camisole over my
head and felt it slip down until it rested lightly
on my shoulders. I walked back across the house to
my bedroom, swaying my hips and loving the feeling
of the silk.

       I slipped under the covers and closed my eyes,
thinking about all the fun I had just had, and all
the fun I was still going to have.

       And that was just the first day...


END OF PART 1, MORE TO COME

I'd love some feedback, send emails to
Vtcarfanatic@yahoo.comMy first time crossdressing
By Danielle Reilly


THIS IS A COMPLETELY TRUE STORY OF MY FIRST TIME CROSSDRESSING

A quick background

       Growing up I'd always been fascinated by
women's clothing. Seeing a girls smooth legs
peeking out from under a skirt, accentuated by her
high heels was just a huge turn on for me. Since
then I've always loved women's lower bodies. The
skirts, panties, hose, and high heels that they
wear are my favorite things in life.

When I was 11 I began to investigate some of my
mothers clothing, rifling through her silky
panties, bras and pantyhose I experienced my first
erection, though at the time I didn't really know
what it was. After a few months of just exploring
her underthings, I began to try them on while the
family was away. Because I went to a private
school, I got out of school at 2:30 in the
afternoon and my mother worked at the public high
school she wasn't home with my younger sister until
4, and my father wasn't home until 6, so I had
plenty of time to explore my feminine side.

When I was 13 I experienced my first orgasm,
while washing myself in the shower. After that, I
just couldn't get enough, and masturbated at least
4 times a week. It was also around this time I
began trying on some of my mother's panties and
hose, and luckily for me my mother and I were the
same size at this point in our lives. After I
turned 14 my parents told me that they were going
on vacation to Florida in the summer, and asked if
I wanted to go with them. Of course seeing the
opportunity to spend 10 days home alone I said no.

The First Day

       Finally June came around, and the day of their
departure came after several sleepless nights of
excitement. After watching my parents drive down
our driveway (which was a long one in full view of
the house), and waiting long enough to be sure they
wouldn't be coming back to get something they
forgot, I ran across the house towards my parents
bedroom, and more importantly my mothers closet,
stripping off my clothing as I went.

       For a while I had been planning for this week
alone, and knew exactly what I wanted to do. I'd
even let my hair grow for the past 3 months so that
I would have semi long hair at the time.

       Heading into her bedroom I quickly raided the
closet. I pulled out her purple minidress. I'd
only seen her wear it once at a party, but I loved
it. It was purple velvet (or something like it),
with low cut shoulders and front. It was a tight
dress and hugged curves, and ended at mid-thigh. I
also pulled out from the bottom or her closet her
pair of 4" black stiletto heels. Moving over to
her dresser, I quickly selected a black wonderbra,
tight black lace panties, and a pair of black thigh
high stockings.

       I quickly hopped in the shower and washed my
hair and body quickly. Being only 14 I didn't have
much body hair, but I went over my body quickly
with my moms razor until I was completely hairless.
Hopping out of shower I wrapped my towel around my
chest like I had seen my mom do a hundred times. I
spent extra time in the mirror making sure my face
was completely hairless. Staying at the mirror, I
opened my mom's makeup case and began to
experiment. I brushed a small amount of mascara to
my eyes, followed by some blue eyeshadow and a
small amount of blush to my cheeks. Finially I
applied some bright red lipstick to my lips.
Looking in the mirror I was surprised to see the
face a slightly older girl looking back at me. I
puckered my lips, and then moved back to the bed in
my mom's room where my clothing was waiting.

       I quickly pulled the lacy bra out of the pile
and wrapped it around my chest. Clipping it in the
front, I rotated it around and slipped my arms
through the straps. After adjusting the length of
the straps slightly (my mother and I were about the
same size after all), I filled the cups with some
flesh colored nylons from the dresser. Grabbing
the panties from the bed, I slinked them up my
hairless legs, relishing the feeling of the lacy
material and it caressed my skin.

       Sitting back on the bed, I balled up the nylons
and slinked them up my legs, snapping them tight
around my thighs. Slipping my feet into the high
heels I stood and quickly wobbled back down on the
bed. Slowly I stood back up and took several laps
of the house, getting used to walking in the heels.
After about 10 minutes I felt comfortable enough in
the heels, but I was experiencing another problem.

       The feel of the lacy panties was driving my
cock nuts, and my raging erection was poking out
the top of the panties. Headed to the bathroom, I
loved the way that my legs and butt felt in the
high heels. The feeling of the lace panties and
hose on my skin, and the way my legs looked in the
heels was turning me on more than I'd ever been.

       In the bathroom I quickly pulled my panties to
the side allowing my cock to spring free. The head
of my uncircumcised penis was dripping precum like
it was water, and I noticed it had actually made a
small stain on the front of the panties. Grabbing
a quick handful of toilet paper and teetering on my
heels, I quickly began to stroke my aching prick.
After only a few strokes I felt my orgasm building,
and I felt my knees buckle as it hit. Falling to
my knees I watched my hot cum spurt right through
the handful of tissues and into the palm of my
hand. Regaining my composure, I dumped the tissue
paper into the toilet and quickly washed my hand,
though the hot cum on my hand had intrigued me. I
tucked my now flaccid penis back between my legs
and was pleased to see the flat front on the
panties.

       Back in the bedroom, I quickly slipped into the
dress and zipped the back. Looking in the full-
length mirror on the wall, I saw a sexy young girl
looking back and me and was pleased with the way I
looked. I took the next 20 or 30 minutes to look
through my mother closet for things I may have
missed earlier, and found a blouse and skirt I
wanted to try on later, as well as some silk
camisoles that I would try on too. Under one of
the camisoles in the drawer, I also found a tube of
KY.

       Deciding that I would spend the next 9 or 10
days as a girl, I poured myself a glass of juice
and, still practicing walking in the heels, went to
the living room. Logging onto the Internet, I
quickly checked my email, nothing new, and then
began surfing the web looking for sites about
dressing as a girl.

       After looking quickly at some websites of some
beautiful t-girls, I stumbled into the nifty
transgendered stories archives. I spent the next 5
to 6 hours reading stories about other people
dressing as girls, living as girls, and what really
peeked my interest were the stores of the people
having sex as a girl. Downloading several of my
favorites to the computer, I logged off the net.
By this point I was extremely horny again, but I
was determined to experiment more. After rereading
a couple of the stories that contained detailed
descriptions of their sexual experiences, I wanted
to try some of them for myself.

       Making my way around the house, I quickly
locked the doors and closed all the blinds,
ensuring that some unsuspecting person would not
catch me. Wanting to feel more feminine than I
already felt, I decided that I wanted to experience
sex in the female sense. Considering what I had
read in the stories, I decided that anal sex was
something that I wanted to try. Knowing that it
would be difficult the first time, I ran back to my
mother's bedroom and grabbed the tube of KY from
her dresser.

       I decided that my bedroom would be the best
place for me to try it, just because I felt more
comfortable there. Feeling very horny and wanting
to have the best experience possible, I decided to
stay dressed as much as possible. Slipping my
panties down my legs, I kicked them off and they
landed on the bed. I began to root through my desk
drawers looking for something to use, and in the
back of one of the drawers I found a .50 caliber
bullet that I had bought several years earlier. It
was roughly the same size and shape and my penis,
and it seemed like the perfect substitute. I
dropped a towel onto my bed to keep from making a
mess on my comforter, and stood next to the bed. I
Spread my legs wide and hiked the dress up and over
my hips like I'd seen so many girls in pictures do,
and bent forward over the bed. I could feel my ass
check pull apart and the cool air of my house
caress my rosebud. I was glad I'd chosen to shave
my butt and clean my ass thoroughly inside and out
while I was in the shower.

       Spreading a generous amount of the KY onto my
fingers, I felt a chill run up my back as I spread
the cold gel onto my hole. Applying more gel to my
hand, I bit my lip as I pushed my middle finger
into my ass. It slipped in surprisingly easier
than I thought, and didn't hurt at all. Sliding my
middle finger in and out I applied even more KY to
my fingers, lubricating my ass thoroughly inside
and out. Soon my hole felt loose enough that my
finger was easily moving, and I slipped in a
second, and as it loosened even more a third.

       As I moved my fingers in and out I relished in
the feelings I was having, and wanted something
bigger. As I removed my fingers my ass felt empty,
and I just had to have something in it. I spread
more KY onto the cold bullet and placed the tip
against my hole. The cold sent another shiver up
my back but I needed it. Pushing in I felt my
sphincter stretch to accommodate it, and I loved
it. Quickly I felt the tip of it slide against my
prostate, and I thought my dick was going to
explode. It pulsated and I could feel cum moving
upwards in my hard shaft. My right arm, holding me
up on the bed, almost collapsed as the feeling
washed over me.

       Unsure of what just happened, but knowing it
was good, I slowly retracted the bullet and pushed
it back in, again hitting my prostate and sending
the feeling through me. Starting slowly I began to
fuck myself with my artificial cock. Moving it
faster and Faster, I could feel the beginnings of
my orgasm and I had yet to touch my hard cock. I
moaned out loud as I fucked my ass, rocking back
and forth on my high heels in rhythm with my
fucking. Looking down onto the bed I say my
panties bunched up on the bed, and I picked them
up, replacing my hand with my elbow and bringing
them to my nose. I could smell my precum on them
and noticed a wet spot on the front where my cock
had rested, and extending my tongue I tasted it.
It tasted very good and I knew I wanted more, but
at the time I was too busy fucking myself to do
anything about it.

       All too soon I felt my orgasm coming, and with
a loud moan I felt my cock swell and explode my hot
sticky cum onto the towel. My sphincter tightened
around the bullet and my entire body pulsed as my
orgasm washed over me.

       I lost track of time briefly and I don't know I
long I stood there, bent over the bed with my ass
in the air like a slut, cum dripping from my now
flaccid cock, but after what seemed like forever I
felt the bullet slip out of my well-fucked ass and
fall to the floor. Still bent over the bed, I
picked up the towel and wiped the dripping cum from
my prick, then wiped the KY from my ass.
Straightening up I slipping my nylon-clad legs back
into the panties and pulled them up around my
waste, and wiggling my hips settled the dress back
into place.

       After sitting on the bed for several minutes
recovering, I went to the kitchen and quickly made
myself a small bowl of soup (I hadn't eaten all day
and needed to keep my strength up). Settling on
the couch, I crossed my legs and slowly ate my
soup, watching Ally McBeal or some other very
feminine show (I can't remember now what it was).

       After the show I decided it was time for bed,
as it was about 11 at night and I had a lot more
plans for the week. Heading back into the
bathroom, I washed off my makeup and headed into my
mother's room again. Slipping off the dress, I
laid it out on the bed neatly, and then opened the
drawer in her dresser containing her nighties. I
selected quickly a white silk camisole with pink
flowers and matching panties. I slipped my feet
out of the heels, and slipped the stockings off my
legs. After unclipping the bra I slid the panties
down my legs, and picked up the white bikini cut
silk panties. Sliding them up my legs, I squirted
some aloe into my hand from a bedside pump and
quickly applied it to my smooth legs, keeping them
soft and smooth. I slipped the camisole over my
head and felt it slip down until it rested lightly
on my shoulders. I walked back across the house to
my bedroom, swaying my hips and loving the feeling
of the silk.

       I slipped under the covers and closed my eyes,
thinking about all the fun I had just had, and all
the fun I was still going to have.

       And that was just the first day...


END OF PART 1, MORE TO COME

I'd love some feedback, send emails to
Vtcarfanatic@yahoo.com
 
back save

Nifty - Transgender - Teen - My First Time Crossdressing - My First Time Crossdressing 1