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I had stated dressing in my mom's clothes around the age of twelve. I
don't know why I tried it the first time, but I just did. I always was very
interested in her clothes and would love to watch her get ready for a night
out on the town with my dad. I loved her pantyhose the best, the way they
looked so shiny on her legs, and I loved the way they made her legs feel
smooth if you touched them. If I was home for a short time alone I would
sneak in my parents room and excitedly try on a pair of her panties and
some of her pantyhose. I did not masturbate when dressed in her clothes,
but I would come very close as I would touch and rub my nylon covered
legs till I would get very excited. One day when I had a little more time I
experimented with some of her make-up. I tried her red lipstick and some
of her blush. I didn't look that good but I enjoyed experimenting with it
and I loved the sweet smell of it. After a few months experimenting with
my mom's clothes I came to the realization that I needed clothes that
would be more in style for a girl my own age. I had a older sister so I
knew that I could step-up my crossdressing a little bit and dress in a
complete outfit from my sister's closet.
I had to wait for a night when both my sister and my parents
would be out for a whole night. When the night finally came I walked in
my sisters room and opened her closet to find the outfit that I wanted to try
on. It was a powder blue skirt with a white silk blouse and a blue jacket
to top it all off. The skirt length was just a inch above the knees, so it
would show off a little of my legs. I laid it on her bed and looked at it. It
was a very pretty and feminine outfit that would be the dream of any
teenage girl. I had seen my sister dress in it many times and I was always
jealous of her when she had in on. Today would finally be my turn.. I
walked over to her dresser and went through her drawers till I found the
one that she keeps her panties and bra's in. I picked out a matching panty
and bra that was white with lace trim. The bra had a small pink rose
between it's cups and the panty had the same rose on the middle of it's
waist. They looked like woman's underwear but the rose said to me that it
was still a little bit girlish. I also pulled out a pair of white tights that I had
seen my sister wear with this outfit. I loved the feel of them as I ran them
through my hands. They were soft and had a very high shine to them. I
had everything laid out on the bed and for a short time I looked at the
complete outfit. I was so excited that my hands were shaking as I slowly
took off my clothes to get ready to do my transformation
I felt funny standing naked in my sister's room looking at her
clothes on the bed that soon would be covering my body. I pick up the
panties and slipped my legs in them and slowly pulled them up to my
waist. I instantly felt how different they felt than my own cotton boy
underwear on my body. They were french cut so they looked very sexy
from the side. I loved the way they fit a little higher over my hips to make
them look a little bigger so more girlish. And the back of the panties
were tighter and made my ass look a bit rounder and feminine. I
slipped the bra over my arms and snapped it in back. It was a satin bra and
very light so it did not have a lot of support, but this made it feel more
sexy. For the first time I felt the soft satin rubbing on my nipples. I
stopped to play with my nipples in my bra. I ran one finger around the
outside of my nipple than slowly touched it. I moved my other hand up so
that I was now touching both nipples at the same time. It was like
electricity running trough my body as I felt my nipples slowly grow and
push against my satin bra. I looked in the mirror and it excited me to see
how sexy my hard nipples looked in my white bra along with a semi-hard
cock in my panties.
I sat on her bed and stated to pull the white tights up my legs.
When I had them pulled up to my waist I slowly ran my hands up my legs
and pulled up the loose slack in each leg so they fit tight on my legs.
I loved the way they felt so snug on my legs and how sexy they felt as I
rubbed my legs together. I could feel the heat as I rubbed them together
and they made that sexy ripping sound. I sat back down on the bed and
slipped both my feet into the skirt. I stood up and pulled the skirt slowly
up to my waist then reached around the back and pulled up the zipper and
felt the skirt get snug on my waist and hips. I slipped my arms into the
sleeves of the blouse and buttoned it in the back and tucked it into my
skirt. I looked in the mirror and could not believe the transformation. As I
looked a little longer I realized that something was missing, I had no tits.
I found two balloons in the house and filled them with water then filled
my bra cups with them. I looked again and saw a young girl with small
teenage breasts. I found the matching blue shoes that went with the outfit
and slipped them on my feet and snapped the straps in front. They had a
small heel on them but it still was a little hard for me to walk in them.
They seemed to make my ass wiggle a little more as I walked and my new
tits bounce in my bra. I slipped on the matching jacket and started to walk
out of the room.
Just before leaving the room I saw on her dresser top the make-
up that she used, and I knew I was not done. I sat down at the mirror and
tried to copy the routine that I had watched my sister do a million times. I
started with some Cover Girl base on my whole face. Then I put shadow
on my eyelids, putting the lighter color up high and the darker color down
low. I slowly brushed black mascara on my lashes till they looked as long
as possible. I put a little pink blush on my cheeks to highlight my
cheekbones. I outlined my lips with a red pencil then finished them with a
pink lipstick and a lipgloss. I looked at my face in the mirror and for the
first time doing full make-up, I did not look half bad. I looked like the
typical teenage girl, a little too much make-up but still pretty.
I spent the next hour looking in the mirror and walking around the
house feeling the soft and feminine clothes on my body. I learned how to
walk in the heels in a sexy way with a wiggle and a bounce in my step not
awkward like a boy. I learned how to sit like a girl and not let my skirt
run up or get folded under me. It was so much more complex being a girl
because of all the things to do and remember but I loved the rewards. I sat
and watched TV and had a coke and it was so funny when I noticed the
lipstick on the edge of my glass. As I got more comfortable in my female
role I started to fantasize and pretend I was a girl, and I was dressed and
waiting for my boyfriend to pick me up for our first date. What would we
do, go to a movie? Would he kiss me at the movie? Would he want more
than a kiss? Would he take me parking? Would he want some kind of sex?
Would he want me to suck his cock? I started to get a hard-on in my
panties as I thought of myself dressed like I was on my knees sucking a
boys cock. I went back to my sisters room to look for something that I
had seen before.
I was to learn later in life that it was called a vibrator. To me it just
looked like a large cock, a very large cock. It was at least twice the size of
my cock. As I looked at it all I could think was this must be what a mans
cock looked like. I knew that I wanted to try to suck it but I wanted to
make this as real as possible. I went to my bedroom and got a pair of my
jeans and stuffed them with a pillow in the crotch and blankets in the legs
to make them look life like. I also got one of my T-shirts and did the same
thing as I did with the pants. I sat both the pants and shirt on the couch
and put the vibrator in the open zipper of the pants so it all looked like a
man with a large cock sticking out of his pants. I slowly got down on my
knees in front of my make believe boyfriend. I was so excited that my
hand was shaking and I moved it to the base of the cock. I bent my head
down and opened my glossed covered lips as the cock invaded my virgin
mouth. I was so stimulated at this point because the pants and vibrator
looked life like that I began to fantasize. I really felt like some femmy fag
boy dressed in his sisters clothes for a mans pleasure with his large cock
in my mouth. I started to act like a sexy girl giving a blowjob as I licked
the cock and sucked on the head. I slowly worked more of the cock in my
mouth not wanting my boyfriend to cum too fast. As I got about half of the
cock in my mouth, I started to gag so I had to pull a little bit out and start
over. I so wanted to please my boyfriend that I kept working at taking all
his cock in my mouth. After 4 or 5 minutes I was able to take the whole
cock with only a little bit of gagging. I loved the way the cock slowly
spread my wet lips and filled my mouth till I felt the tip hit the back of my
throat. As I got more comfortable sucking the cock I slowly sped up till
my head was bobbing up and down on it and my face was deep in his
crotch. I was pretending that I was working my boyfriend to a hot
climax, as I was thinking how nice it must feel for a girl to have a guy
cum in her mouth
I was so excited that I started to rub the front of my skirt with one
hand as I still held the cock with the other and kept bobbing my head up
and down. My excitement seemed to make my whole body hot and caused
me to feel my satin panties on my cock, my satin bra on my nipples, my
nylon covered legs, the soft material of the dress rubbing on my
pantyhose covered ass. When I filled my panties with cum I did one final
thrust down on the cock and let it fill my mouth so that my final loud
moan and whimper was muffed. I must have laid with that cock in my
mouth for 5 minuets till I found the energy to lift my head up. My whole
body ached and my mouth was sore from the work-out I gave myself.
What was funny was that I had a feeling of being proud of what a great
blowjob I had completed. I only wished that it had been a real boyfriend
that could hold me tight and slowly stroke my body and kiss me and tell
me what a great lover I was. I slowly cleaned all the clothes and put them
in the correct place so my sister would never know. I cleaned all the make-
up off my face put all my clothes back on. I walked into the livingroom and
turned on the TV and laid on the couch. As I watched TV I started to think
of my experience. I could start to feel my cock in my pants get hard. Just
then my mom and dad walked in the front door and my dad said " so is
that all you been doing all night, watching TV. "Thats about it" I said with
a smile as I moved my hand off my zipper.

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