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Subject: My first time crossdressing
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My first time crossdressing THIS IS A COMPLETELY TRUE STORY OF 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...
Waking up in the morning, I relished in the feeling of
the silk camisole and panties against my smooth skin. I
smiled as I thought of the previous day, and what was still
to come. I walked through the house, feeling the cool
morning air against my skin, and planning my day.
I walked into the bathroom, pulling the camisole over
my head as I passed the door. Dropping the camisole on the
tile floor I turned on the shower, then changed my mind and
decided on a bath. After the tub finished filling, I
dropped in a few scented bath bubbles, and slid the panties
down my legs. Sliding down into the tub, I let the hot
water wash over my body. After about 20 minutes of
soaking, I grabbed a razor and quickly went over my body
again. There wasn't much hair anyway, but it still felt
nice lifting my leg out of the water, pointing my toe and
running the razor down my wet skin. After a close shave of
my face to remove the peach fuzz, I climbed out of the bath
and patted myself dry.
Wrapping the towel around myself, I walked down to my
mother's room again. Looking quickly through the closet, I
decided on a white blouse and a black skirt, mid thigh
length again. Heading to the lingerie drawer again, I ran
my hands through the materials. I selected a white pushup
lace bra and matching panties, as well as a pair of nude
pantyhose. I grabbed the same pair of 4" heels from the
day before and put them all on the bed.
Dropping the towel on the floor, I wrapped the bra
around my body, clipped it in the front and spun it around.
After slipping my arms through the straps, I again filled
the cups with the flesh colored pantyhose. Picking up the
panties, I quickly slid them up my legs and folded my penis
back, which was difficult because I was semi-hard already.
After getting my cock set between my legs, I turned to the
pantyhose. I balled up both legs at once, and gently
pulled them up, almost like a pair of pants. After
checking to make sure they were straight and there were no
runs, I took the blouse off the hanger.
I slipped my arms into the sleeves and buttoned up the
front. I noticed that the material was semi-transparent,
and I could clearly see my bra through the thin material.
As I picked up the skirt from the bed, I heard a horn out
front. As my heart began racing, I rushed to the window
and peeked out. It was my mom's friend Linda; I forgot my
mom said she's asked her to check in on me!
Quickly stripping off the blouse and bra, I threw back
the covers on the bed to cover all the clothing. I tossed
the shoes back into the closet as I raced for my room. I
quickly pulled on a pair of jeans over my panties and hose,
and then a pair of socks over the visible hose on my feet.
I threw on a t-shirt as I ran through the house, arriving
at the front door just before she did. Opening it almost
out of breath, and having a mini-heart attack at the
possibility of being caught, I tried to play it cool.
Thank god I hadn't put on any make-up!
After talking to her for about 5 minutes and assuring
her I was ok alone, and had enough food and drinks to last
the 10 days, She climbed back in her car and drove off.
Locking the door again, I peeked out through the window to
make sure she didn't come back. After about 30 minutes I
was pretty sure she wasn't coming back, and I had
sufficiently calmed down enough to get dressed again.
I quickly stripped off my boy clothing and walked back
to my mother's bedroom, where I again put on the bra and
blouse. Taking the skirt off the rack, I slid it up my
legs and tucked in the blouse. Zipping up the back and
fastening the clip, I pulled it down till the blouse was
tight around my upper body. I slid my feet into the heels
and loved the feel as I felt my legs and butt tighten as I
stood in them. Walking back to the living room, I again
sat down at the computer and began surfing the net for TG
girls and other sites.
Again I found myself at the Nifty Erotic Stories site.
Once again I found myself reading the stories for hours. I
especially loved the ones of guys dressing as sexy girls,
and doing everything that a girl gets to do. Shopping,
going out to the malls, and especially the sex. I was
captivated by the graphic stories of the TG girls giving
blowjobs to guys and having anal sex with men.
After reading one particularly graphic story, I rock
hard cock was poking out the top of my panties, and if my
legs hadn't been crossed (a very sexy feeling with my nylon
clad legs rubbing against each other), and the skirt being
so tight I would have had a tent in my skirt.
Quickly I found a few sites about anal masturbation
and techniques, I decided it was time to have some fun. I
quickly decided to do a little more than I had done the day
before, and had an overwhelming desire to find out what cum
tasted like.
After thinking for a few minutes, I got a large beach
towel and spread it on the floor to keep from making a
mess. Locating the bullet I had fucked myself with the
previous day and the tube of KY, I quickly stripped off all
my clothing. Piling the skirt, blouse, panties, bra and
hose on the couch, I slipped my now naked feet back in the
high-heeled shoes. I laid down on my back on the towel, my
rock hard cock sticking almost straight up, precum running
down the side. I scooped up a fingertip of the precum and
brought it to my lips. It tasted good and I quickly
scooped the rest of it off the head of my cock.
I pulled my feet in close to my butt so that the
bottoms of the shoes were flat on the ground, which forced
me to elevate my butt into the air. I could feel the air
caressing my still loose sphincter from the day before.
Again I spread a generous amount of the KY over my hole and
the bullet, and then slipped a finger inside my tight ass.
It was much easier than the day before and it was quickly
joined by a second.
After a minute or two of finger fucking my ass, I
placed the head of the bullet at my hole and gently
pressed. I moaned as my sphincter stretched around it, and
it easily slid in until it rubbed my prostate. I could see
my dick twitch as the bullet rubbed my swollen gland, and I
slowly began to fuck myself again.
While my left hand worked the bullet in and out, my
right traveled all over my body, loving the smooth feeling
of my skin, it settled at the base of my cock. Not wanting
to touch it and ruin the fucking I was getting, I gently
teased the bottom of my cock, and scooped up my precum
bringing it to my lips.
After about 10 minutes of fucking myself I couldn't
take it anymore and needed an orgasm. I gently began to
stroke my shaft with my free hand and I began to fuck
myself faster. After only a few strokes I was ready to
cum, and knowing that I wanted to taste my cum I lifted my
head toward my throbbing dick. Placing my lips only an
inch or two from the head of my dick, I was ready for my
first taste of cum.
Feeling my orgasm building, I opened my mouth wide and
closed my eyes. In my hand I felt my dick swell and my
anal muscles contract around the bullet, holding it against
my prostate. I felt my dick pulsate in my hard as the
first jet of hot cum sprayed into my mouth. It was
followed by a second, third and fourth shot. The next few
shots dribbled from my throbbing cock and onto my stomach,
but I didn't care. I swirled the cum in my mouth around a
few times tasting it, then swallowed. I love the feeling
as it slid down my throat.
With my free hand I scooped up the cum from my stomach
and sucked my fingers clean. I smiled from the experience
and lay there for a few minutes. Finally I stood and,
grabbing some tissues from the box on the table, I cleaned
off my stomach and wiped the gel from my sex hole.
Dressing again, I noticed that it was almost 12 and decided
to make a lunch, even though I wasn't really hungry, I knew
I would still need strength.
After a quick sandwich, I decided to just lounge
around the house for a while, so I kicked off my heels and
lay back on the couch. I must have fallen asleep because
the next I knew it was dark outside and the news was on TV.
I yawned and stretched, and slipped my nylon-clad feet back
into my heels. After walking around the house looking for
something to do, I just decided to go to bed and slipped
out of my skirt and blouse. Sliding the camisole back over
my head, I again loved the feeling as it caressed my skin.
I slipped under my covers and was quickly asleep, just
waiting for the next day.
THE THIRD DAY
Waking in the morning, my asshole itched, and I felt the
burning desire to be fucked again.
Back in my mother's bedroom, I slipped out of the
camisole and panties, and rifled through my mother's
drawers again and found, in the back, a very sexy matching
black lacy bra and panty set. There was almost nothing to
the material, and the bikini cut panties were so light
there was almost nothing to them. I quickly slid them up
me legs and settled them into place around my hips, and my
dick twitched as the lace encased my sensitive member.
Clipping the bra on my chest, I thought about the sexiest
thing I could wear. My mind settled back on the purple
minidress from the day before. I slid the black thigh high
stocking back up my smooth legs and settled them into the
place. I slipped my feet into the dress and slid it up my
legs. After settling the top in place I zipped it up and
stepped back into my 4" heels. Looking in the mirror I
thought I was sexier than hell, with the tops of my
stockings just peeking out from under my dress as I
extended my legs to walk.
At this point I just wanted to feel something in me,
so I quickly went back to the living room. My bullet was
sitting on the towel where I had left it after my fucking
that morning, and I quickly grabbed the KY, hiked my dress
up around my hips and pulled my panties to the side. I
almost didn't need the lube, my hole was loose and wet from
my anal juices, but it just felt good. I began prodding my
hole with my fingers, fucking myself over and over. I
decided to be more independent than I had been last time
and stood the bullet up on its end. Kneeling over it, I
lowered my ass towards and gasped as it easily slid inside.
Gently and slowly I started bobbing up and down on the
fuck stick, my cock throbbing in its lacy sheath, but I
didn't want to touch it. I just kneeled there, slowing
bobbing up and down on the hard phallus. After what seemed
like an eternity, but couldn't have been more than 10
minutes, I felt my cock begin to swell and my orgasm
approach, forgetting completely that I was still dressed, I
let the pleasure wash over me as I felt my tight panties
fill with hot cum.
I leaned forward and felt the bullet again slip easily
out from my ass, leaving me feeling empty inside. Peeling
the sticky panties down my legs, I tossed them towards the
laundry room as I sat down in a chair. I loved the feeling
of the velvet dress caressing my smooth butt with no
panties, and decided I wouldn't wear panties for the rest
of the day. I spread my legs and let the cool house air
caress my hairless crotch. I must have sat like that for
half an hour before I decided to move, and I smiled as I
listened to my heels clicking across the wood floor of the
room.
Back on the computer, I began looking at sites about
oral sex. I became fascinated by the graphic descriptions
of sucking on a hard cock, teasing the man, feeling his
jism spray into your mouth. I began to wonder what it
would feel like to suck a man's cock, and after reading
several stories and downloading a few movies, I decided I
needed to get off again.
I walked back into my bedroom and reached behind my
back, gently tugging the zipper on the dress down. I let
it slip off my shoulders and let it fall to the floor in a
pile around my sexy heeled feet. I unclipped my bra and it
quickly joined the dress on the floor. I crawled onto my
bed and propped up a couple pillows on the end and lay back
on the bed. Spreading my legs I looked down to see my hard
cock standing straight up, and I loved the look of my
smooth skin, thigh high stockings and heels all together.
Gently stroking my cock with my left hand, I pulled my
heeled feet towards my butt, which forced me to raise my
ass off the bed and my cheeks pulled apart. My free hand
began to caress and probe my still loose hole, fingers
easily slipping inside. I closed my eyes and began to
fantasize.
I saw myself in the same purple dress and heels, but I
was on my knees on the floor, doggy style. In front of me
stood a man, faceless and naked, with a hard 7" cock just
inches from my face. At the same time another man stood
behind me, and pushing my dress up I felt the head of his
hard cock at the entrance to my love hole. As he gently
pushed his way inside me I moaned out loud, and as I opened
my mouth the man in front of me took a step forward and I
tasted his hot cock. I let is slide all the way into my
mouth and then back out, and I began to work on it with my
tongue and he slowly fucked my face. Alternately the man
behind me continued to fuck my tight hole, slowly at first
but then faster and faster.
I could almost taste the hot cock of my faceless
lover, and I moaned out at the thought of feeling a hard
dick pounding my ass. With a cry I felt my cock throb and
yet another orgasm hit me. The first jet landed squarely
on my lips, and I quickly opened my mouth and licked it all
off. The rest of my sticky cum traced a path down my
hairless chest and stomach, and formed a puddle around my
now flaccid cock. I pulled my finger out of my loose hole,
and scooped up the cum from my chest, licking my fingers
clean.
Exhausted from my multiple orgasms of the day, I
just lay back and fell asleep with a smile.
End of part 2, still more to come
The College Years
After my week of dressing, my mother noticed that things were not
quite as she had left them, and became suspicious. She asked me if I
had
been in her things that I of course denied, but I think she knew what I
had
been doing. Because of this I quickly put a stop to my dressing, but
continued reading stories of other crossdresers, looking at pictures,
and
of course masturbating to them.
Many years later I graduated from high school and moved on to
college. In college I was lucky enough to get a single dorm room, and
immediately saw the opportunity for a previously unknown privacy. After
a
few months of getting used to the college lifestyle and classes, I
decided
it was time to renew my interest in dressing, and the next weekend I
jumped
in the car and headed to the store.
Deciding that Wal-mart was the best store for me at the time, I
went inside and headed for the lingerie department. I didn't want to
arouse any suspicion, so I quickly bought a black garter belt, a pair of
black thigh-high stockings, and a powder blue thong. I told the
checkout
woman they were for my girlfriend and asked if they were returnable if
she
didn't like them, and then headed two towns over to the next closest
Wal-mart. There I bought a pair of purple bikini-cut panties, a purple
thong and 3 pairs of nude stockings. Knowing I would never be back to
this
store I hurried through the checkout lane and drove back to the dorms.
For the rest of my freshman year, when the urge hit me I would slip
on the panties, garter belt and hose and masturbate, but when the
semester
ended I hid these fanciful items at the bottom of a box and went back
home
for the summer.
Heading back for my sophomore year, I met a girl named Jill. She
had fiery red hair and we quickly became great friends. She had an off
campus apartment all to herself, and quite a few nights I fell asleep on
her couch, we became close very quickly. She was 6' 2" tall so we saw
eye
to eye, but wasn't skinny in the traditional sense, in fact the two of
us
shared basically the same body except for the fact that she had large DD
breasts. We talked about everything from sex to movies to classes, but
I
was reluctant to share the secret of my crossdressing with her for fear
of
alienating her.
After several months though, she was looking for laundry detergent
in my closet (she spent a lot of time in my room so I thought nothing of
it) she ran across my panty stash. I didn't know about it at the time
and
she didn't say anything, and for several days I heard nothing about it.
About a week later we were chatting AIM about things and we got on
the subject of fetishes somehow, and she asked if I had a panty fetish.
At
first I denied it but when she explained that she had found my stash and
wasn't upset or anything just curious and wouldn't think any different
of
me, and after some prodding from her I let it slip that I enjoy wearing
them. To my surprise she said she thought it was interesting and wanted
to
know more.
After a long talk that went far into the night, I had told her all
about my week alone, my Internet activities, and my desire to dress
more.
Towards the end of the conversation, she asked me if I would ever
consider
dressing with someone, and I told her if it was someone I trusted, which
she replied to asking if I would like to come over to her apartment and
dress, and she would help. At first I was reluctant but she finally
talked
me into it, and we decided on Friday as the day.
Thursday night I didn't sleep much at all, and Friday I sat through
my morning classes in anticipation. My penis was already mostly hard,
and
concentrating on the boring material was tough. Finally my classes were
done and I jumped in my car and raced to her apartment. After the short
drive, I arrived at her apartment around 12, and knocked on the door.
She opened the door in a short black skirt, white tank top, and
platform sandals that made her slightly taller than me. Her red hair
was
pulled back and she smiled at me as she stepped aside and invited me
in. I
followed her up the stairs to her apartment (she lived on the top floor
of
a house that was divided into several apartments), and after a few
moments
of awkward silence she asked if I wanted to get started. Not knowing
what
else to say, I said sure and she handed me a bottle of Nair (at this
point
in my life I had a fair amount of body hair). She told me to apply it
to
everything from my neck down and pointed me towards the bathroom.
In the bathroom, I stripped off my clothes and quickly applied the
bottle to my body. Through the door I asked her what to do next, and
she
told me to wait 5 minutes than get in the shower, which I did. While I
was
in the shower rinsing off the foam and watching my hair run down the
drain,
I heard the door open and close again, and I heard Jill on the other
side
of the curtain. She scooped up my clothing, then told me to towel off,
wrap the towel around myself and come on to her bedroom. Climbing out
of
the shower, I wrapped a towel around my chest and walked to the bedroom.
She sat me down in front of her Vanity mirror, and told me to close
my eyes. She immediately started plucking my eyebrows to give them a
more
feminine shape, and then I felt her tug a wig down over my hair. After
ensuring my eyes were still closed, she went to work on my face and I
could
feel her applying concealer, mascara, eyeliner, and lipstick. Finally
she
announced that she was done and I opened my eyes. In the mirror was a
young blonde woman that could easily have been mistaken for Jill's
sister,
and I beamed as I saw myself. She giggled as she saw my reaction and
told
me to get dressed.
As she left the room and closed the door behind her, I turned in
the chair to see the clothes she picked for me on the bed. We were
almost
exactly the same size so I wasn't worried about anything not fitting.
Dropping the towel, I picked the blue Victoria's Secret thong and
slipped my smooth legs through the holes. I settled the back
comfortably
between my cheeks and realized that the thin material would do nothing
if I
became any harder than I already was, but I did my best to make my
semi-hard member smooth behind the front. I picked up the matching lacy
bra and clipped it around my check, then spun it around and pulled my
arms
through the straps. I noticed for the first time the two water balloons
on
the bed, and I placed them in the cups giving myself DD breasts. I
cupped
my hands around them and bounced them, feeling the weight and smiling at
my
new breasts.
Next I grabbed the jean skirt that was laying on the bed, and
slipped it up my legs. As I zipped the back, I realized how short it
actually was; it ended just about my mid-thigh and I could see it would
take constant attention to ensure my panties wouldn't be visible if I
bent
over or sat down. A white top, sleeveless and low cut in the front,
followed the skirt and I quickly buttoned it.
Finally on the floor was a pair of stiletto heels. They were black
with thin ankle straps and a 3-inch heel, and I picked them up and sat
on
the bed. I felt the skirt ride up and felt the comforter on my smooth
upper thigh.
Slipping my feet into the shoes, I wrapped the ankle strap around
and buckled it. The shoes were a little tight but still fit, and as I
stood I felt my thighs stretch and tighten, and I teetered on the heels
before I regained my balance. I took several laps of the room to get
used
to walking in the heels, and then opened the door and walked out into
the
living room.
Jill whistled from the couch where she was sitting as I walked into
the room. I strutted to the middle of the room and spun around. I felt
the skirt lift as I twirled and knew that she was getting a good look at
my
thong and I felt my cock grow at the thought.
"Come here" she said after I had finished twirling, and I strutted
myself
towards the couch. Stopping just in front of her, I stood there with my
legs spread shoulder width apart, I was surprised when she leaned
forward
and ran her fingers up my smooth thighs.
My cock instantly sprang to attention as he fingers ran up and down
my thighs, and as her hands slipped under the hem of my skirt my lips
parted and I let out a low moan. She smiled at and ran her hands up
farther, then slid them back down. I bit my lip and looked down at her,
and she grinned back with a sly look in her eye.
"You look incredibly sexy right now, you know that?" she asked me.
"I feel incredibly sexy too" was the only reply I could muster.
She stood and pressed her lips into mine. At first I was surprised
but quickly closed my eyes and reciprocated the kiss, our tongues
intertwining with each other. I could taste our lipsticks and that
turned
me on even more. My hands wrapped around her back and caressed her
hair,
while hers moved down my back.
After what seemed like an eternity kissing, she broke it by turning
me towards the couch and pushing me backwards. I teetered on my heels
for
a brief moment then fell backwards onto the couch. Jill dropped to her
knees in between my legs and leaned forward to kiss me again. As we
continued to kiss, I felt her hands running up my thighs, pushing my
skirt
higher and higher, till I felt cool air in my hairless crotch. I knew
my
thong was doing almost nothing to hold my hard cock in place, and the
thought of what it must look like made it twitch. I felt her hand tug
at
the thong, and it slipped to the side as my cock sprung into the air.
I felt her smile as we kissed and she pulled back and looked down.
"Mmmm, I like what I see here." She murmured before she pushed my legs
further apart with hands and dropped her mouth towards my crotch.
I could feel her warm breath on my skin as she began to lick and
kiss my shaft and head. She worked her way down till she kissed my
sack,
then back up towards the head. I threw my head back and moaned as she
did
that, which made her giggle and lick my head harder. She kissed her way
down my right thigh, then back up and down the left one, driving me
insane.
Finally she settled back on my crotch, and slowly took my throbbing
member
between her soft lips.
I didn't last long as she gave the most exquisite blowjob ever, and
after what seemed like too short a time I found myself moaning that I
was
about to cum. She pushed her head further down on my shaft till I felt
the
back of her throat tough my head, and she let out a soft moan that shook
the muscle against my penis, and I exploded into her mouth.
I clutched the edges of the couch as my whole body tightened with
my orgasm, and I involuntarily lifted my bottom from the couch and
half-stood as it took over. I felt her suck it all down as I shot
inside
her mouth, then I collapsed back down as she finished me off.
She gave the tip of my dick a flick of her tongue as she removed it
from her mouth, and after cleaning a few spot of cum from my shaft, she
tucked it back into my panties and smoothed out my skirt. I looked down
at
her with a smile, and told her it was time to return the favor.
We quickly swapped positions, and after a few more passion-filled
kisses I lowered my head and began to kiss my way up her thighs. I was
anxious to return the awesome orgasm she had just given me, and I
quickly
pushed her skirt up around her waist as I continued kissing. I
immediately
noticed that she wasn't wearing panties and knew she had been planning
this
from the moment I first told her about my dressing.
She moaned out as my kisses found her clit, and I sucked it into my
mouth and bit down gently. Her body shook as her first orgasm hit her,
and
I grabbed her hips and pulled her crotch towards my face as I sucked
harder
on her clitoris.
After her first orgasm passed, I began to work my tongue lower, and
quickly it slipped inside her. She moaned even louder, and with my
right
thumb I began to rub and massage her clit as my tongue worked in and out
of
her wet folds and hole. Quickly she had a second and third orgasm
before
she begged me to stop and let her breathe.
I smoothed the skirt back down and sat on the couch next to her.
As she caught her breathe, her hand began to caress my thigh again and
my
cock again began to harden. As we sat there side by side continued to
kiss, until suddenly she threw her leg over me, and straddled me with a
leg
on each side. She broke out kiss just long enough to tell me she wanted
to
feel me inside her, and with her free hand pushed my skirt up around my
waist and again pulled my thong to the side.
She hiked up her own skirt, and quickly lowered herself down to my
crotch. I felt my cock at the entrance to her hole, and then it slipped
inside. The feeling was incredible as she bobbed up and down on my
erect
member. We continued to kiss, and our hands intertwined as we fucked
each
other.
After what again seemed like too short of a time, I moaned through
our kiss that I was going to cum, and she replied that she was too. As
her
body pushed down on my cock, I felt my shaft swell and my hot cum began
to
shoot inside of her. As she felt my cock swell and begin to unload, her
own orgasm washed over her and she collapsed onto me. Our kiss broke as
her head fell to the side and she moaned out.
As we sat there together, my now softening cock still inside her,
she began to nuzzle and kiss my neck. After a bit of this she rolled
off
and told me to go clean myself up, and I looked down to see dried cum
from
both of us all over my crotch. I strutted to the bathroom and quickly
used
a wet washcloth to clean the cum from my skin, then tucked my now
completely flaccid penis away. Settling my skirt back into place, I
emerged from the bathroom and followed Jill into her bedroom again.
She quickly fixed her make-up in the mirror, then turned to me and
redid mine just as quickly. Handing me a small purse, she said we were
going out and to grab my wallet. A little apprehensive about going out,
I
hesitated briefly, but she reassured me and I grabbed my wallet off the
bed
(my male clothing was no where around) and followed her out the door.
Part 2, in public coming soon
My first time crossdressing part 4: The College Years chapter 2
As Jill dragged my by the hand towards the door, I became more and more
scared about going outside. I didn't really have a choice so I just
kept
my mouth shut and silently hoped that it would go ok. Luckily her car
was
parked out back of her apartment building, so we wouldn't be seen from
the
road as we went outside. This put me at ease and I just followed her
out.
My heels clicked on the pavement as we quickly walked to her car and
climbed in.
My skirt rode up my legs as I sat in the passenger seat. I swung my
legs
into the car and noticed how high my skirt was sitting, but no amount of
adjustment would change it. I knew that anyone in truck would be able
to
get a good glimpse of my panties, and the thought turned me on a little
more.
She started the car and we quickly pulled out of her apartment complex
and
jumped onto the highway, and quickly we were several towns over. I
realized where we were going and quickly I was more at ease than I had
previously been. The town we were headed for was well known for having
a
large gay community, and an equally large transgendered community, so
the
thought of being there dressed as I was wasn't nearly as scary as it had
been earlier.
We rode almost in silence, listening to the radio as I kept taking
glimpses
of her smooth thighs under her skirt, and I noticed that she kept
glancing
at mine, which made me smile some more. After about 20 minutes in the
car
we got off the highway and pulled into a large parking lot, and I
realized
that we were at the mall. We parked quickly and climbed out, and again
taking my hand Jill, lead the way into the mall.
I don't even know how long we were there, it must have been hours, but
to
me it was one long blur of activity. Several times I did notice people
looking at us, but not in any weird way just looking at the two nicely
dressed women shopping. By the time we walked out of the mall I had at
least 5 bags of stuff. I had bought 4 new pairs of shoes, 3 dresses, 2
skirts and 5 different types of tops. I also had a bag from Victories
Secret with a wide assortment of bras, panties, and stockings, and a
couple
full pieces of lingerie.
Walking around in the mall we even got a couple of wolf whistles that
made
me blush, and I think I even wagged my butt at the people whistling.
Walking out of the mall the sun was going down, and I felt my stomach
rumble. She asked if I was hungry and I said yes, so she told me to put
my
bags into the trunk, then grabbed my hand and pulled me towards the
Applebee's that was next door. Inside I noticed the hostess look us up
and
down and smile a little, probably knowing I wasn't really a girl, but
she
sat us politely and we ate an unhurried dinner. She told me that back
at
her apartment she had a surprise for me and I felt my cock twitch. I
had
gone through almost the entire time in the car and at the mall in a
semi-erect state and I was doing everything I could to keep myself from
getting fully hard, but she wasn't helping as I felt her rubbing my calf
with her foot under the table.
After dinner we drove back to her apartment, the entire way with her
hand
on my thigh. I tried to concentrate on something else but her hand was
massaging my smooth skin and driving me nuts. Back in her apartment I
put
my bags into the bedroom as she told me and sat on the couch. She went
into her bedroom and closed the door behind her, and I wondered what she
was doing on there.
Shortly she came back out, wearing the same clothing. I had thought she
was going to change but I guess she was doing something else. Again she
dropped to her knees in front of me and I leaned forward. We began to
kiss
harder and harder, till out faces were pressed tightly together and our
tongues wrestled together almost roughly.
I felt her hands again moving up my thighs and her thumbs hook into the
sides of my thong. She tugged it down and my cock sprung free and was
again creating a tent in the front of my skirt. She pulled her lips
from
mine and dropped her mouth to my hard cock. She licked her way up and
down
my shaft and my cock twitched every time she moved. Finally she
engulfed
my cock with her hot mouth and began to suck up and down my shaft, as
her
tongue played with the bottom if my cock. Too soon I felt my cock swell
with my cum and she looked up into my eyes as I exploded into her mouth.
As my orgasm subsided, she brought her head back up to mine and kissed
me.
Before I knew what she was doing she had emptied her mouthful of my warm
cum into my mouth. Not sure of what to do I just accepted it and
swallowed. I felt her smile as I swallowed, and she pulled her head
back
and looked into my eyes.
"Are you ready for your surprise now?" she asked me.
I told her yes and she stood up before me. She reached under skirt and
pulled her pink panties down to her feet, and kicked them across the
room.
Then she reached behind her and unzipped her skirt. Dropping it to the
floor, she smiled as I saw for the first time the 8" strap-on dildo that
she was wearing. She smiled at me as she told me that she wanted a
blowjob
too.
I leaned forward and gingerly took the blue dildo between my lips,
slowly
licking up and down its shaft, and with every stroke I took more and
more
into my mouth. Jill moaned as the back of it pushed against her clit,
and
I worked it harder as a result.
After a few minutes of my blowing her new cock, she pulled it back and
told
me it was time to experience sex as a woman. I was a little scared as
she
pulled me off the couch and led me towards her bedroom, her erect dong
pointing the way. She walked me down to the end of her high bed and
told
me to face the bed.
I turned and as I did, she kicked my feet apart towards the posts of the
bed, till my feet were spread so far apart I teetered on my shoes, and
had
to lean forward against the bed to stay standing. Before I knew what
she
was doing, she had tied each on my ankles to the bottoms of the
bedposts,
ensuring my legs would stay spread no matter what. I tried to turn and
look back but from my extreme angle I couldn't see much. I felt cool
air
rising up under my skirt and knew that my bottom was exposed for her.
I felt her fingers probing at my puckered anus, and she told me to relax
a
little as she spread a handful of lube on my hole. Then I felt the tip
of
the bottle gently penetrate me as she squeezed even more up inside of
me.
She lifted my skirt the rest of the way off my butt leaving me
completely
exposed and then I felt it; The tip of her new cock pushing gently at my
hole. I relaxed as much as I could and I felt the head slide in past my
rim. We moaned in unison as she gently pushed it further in. As she
pulled back I felt empty inside and begged for more. Gingerly she began
to
put more and more of it inside me with each stroke, until she was
burying
the entire thing inside me with each stroke, and almost completely
withdrawing it pulling back.
She gloriously fucked me like that for about 10 minutes, until I felt my
cock begin to well up again. Through the moans I told her that I was
going
to cum, and she immediately stopped with the dildo buried inside me.
"Not until I do Hun" she told me, and gently withdrew the dildo from my
ass. I felt her bend over and unstrap my ankles, and she told me to
turn
around.
As I turned, she pushed me back on the bed, then reached out and grasped
my
hips. Sliding the dildo back into my ass, I wrapped my legs around her
hips and hooked my feet behind her. Holding myself up with just me
hands,
I began to ride her. She bit her lip as I ground the back of the dildo
against her clit, and as the head of the dildo pushed against my
prostate I
felt my orgasm building again.
I shouted out that I was going to cum, and she said she was too. In
unison
we moaned, as I shot my load past my head and onto the bed, then as it
slowed it landed on my chest and stomach. I could feel her shaking as
we
collapsed onto the bed together.
Caressing each other as we lay on the bed, I told her that it was the
best
day I'd ever had, and she smiled. After what seemed like too little
time,
She told me to take a shower and clean the cum off me, and as I
undressed
she took my clothing and put them in the sink along with her panties to
soak.
Climbing out of the shower I found a box sitting on the toilet seat.
Inside was a sheer powder blue babydoll nightgown with matching
panties. I
slipped it on and then stepped into the blue high heeled slippers that
were
sitting on the floor, and went back in the bedroom.
Jill whistled as I walked in. She was lying on the bed in a pink satin
nighty. I kicked off the shoes and climbed onto bed with her. Talking
about the day, she assured me it was only the first of a lot of more
fun.
Then we climbed under the sheets together and fell asleep...