All
I know is what I have been told about my early life. I am the youngest in my family of seven
children and the only boy. My sisters
are about 18 months apart and are Margaret, Catherine,
Ann, Sara, Mary and Joan, my name is Matt, short for Matthew. I was born in 1966. I grew up in a small,
middle class southern town. When I could
remember, I remember I did not have a father.
My mother told me my father left, and that was that. My family was my sisters, my mother and her
sister. My mother was the administrator
of a small hospital. She provided well
for our family. My aunt worked in real
estate and helped to pay the utility bills and provide for some of the extras
that a family needed.
My
first memory as a boy was standing in the bathtub. I must have been four years
old, my youngest sister Joan was around six.
We were standing in the tube waiting for the bubble bath to bubble
up. I was standing there naked with my
wee-wee showing. My wee-wee was not big,
but it stood out causing me to noticed I had one and Joan did not have a wee-wee.
Noticing the difference, I asked my mommy why.
She told my I was a boy and boys had wee-wees and girls did not. That is all she said on the subject. I tucked my wee-wee between my legs trying to
look like Joan. I told my mommy that I was a girl, Joan giggled, mommy laughed
and so did I. I did the tucking trick a
lot. Every time I was naked and one of my sisters could see me, I would tuck
and pretend to be a girl. I wanted to be
like them. All my sisters got a big
laugh out of my tucking trick.
They
would say, “Oh I see your wee-wee.” I would turn around tuck my wee-wee between
my legs and then show that I was like them.
I would say, “Look I am a girl” and I would prance round emulating my sister.
The
next thing I remembered was my Aunt yelling at me for leaving the toilet set
up. I do not remember who taught me to
pee standing up like most boys. Like most boys, I did not pay attention where
the pee was going and sometime missed the pot. I did not remember ever told to put the lid
down after every use. Well I guess one
morning my aunt went in and sat on the porcelain rim and was very upset. My mommy told me to
always to sit down to pee thinking this would be the best way to make sure that
it did not happen again. That little
advice was surly useful because I did not have to worry about leaving the
toilet seat up, I still do not know what the big deal about the toilet
seat. Half the time it is up or halt it
is down, I have to lift it up to pee, or it is just as easy to have her lower
it to pee. Today when I go to a public restroom, I use the stalls and not the
urinal.
Sunday
was laundry day, and I remember watching my mother fold all the clothes of my
five sisters. I remember seeing white
panties, pink panties, white bra and some colorful bra and panties that belong
to my aunt. When my mother was not
watching I would fall into the fresh out of the dryer clothing and felt the
warmth surrounding me the smell of clean cloths. I would feel the silky touch of my aunt’s
undergarments. The warmth of the clothes felt like when my mother would hold me
in her arms, and I felt safe and secure.
My
family was large leading to some challenges growing up. Every year our cloths
passed to the next younger child, from one sister to sister to me. For the first years of my life, what I got
was Joan’s clothing, panties, her girl jeans and tee shirts in pink, purple or
green. From an early age, I was given
girls underwear to wear. It did not matter; I did not know the difference in
the underwear. I always sat down to pee not need the opening that boys
underwear had. The panties were the
standard white cotton panties with bows. Some of the panties were pink from
washed with something red. Wearing pink girls'
panties was never an issue in kindergarten. No one noticed, if someone did, I
do not remember anyone making an issue.
My
family was casual when it came to our personal habits. The bathroom door remained open unless when
one of the girls was getting ready for a date then she would spend hours in the
bathroom making the rest of us wait until they were pretty for their date. Therefore, I have visions of my sisters in
various state of dressed and undressed and can remember comparing the
differences in breast size and pubic hair. I started to notice my sisters'
breasts when I started the first grade, my oldest sister Margaret was fifteen. I
was walking down the hall the door to the bathroom was open, naturally, and I looked in. Margaret my oldest sister was standing in
front of the mirror looking at her breasts.
I watched as she put on her bra, backwards and twisted it around
slipping her arms through the straps and adjusting each breast. I remembered that each year before the start
of the school year the big event would be one of the girls would be given her
first training bra. Ann who was about 12 received her first training bra. It
was a big deal with much giggling. I remember thinking that when I was older, I
too would receive a training bra.
I
had curly hair, and it was kept long, up to my first year in school when it was
all shaved off. I cried that night
because I missed my shoulder length hair that made me look like my sisters, now
I look not like them... When I was in
first grade Margaret was starting so far, and she was using make up. I would sit there watching her take this
brush and put it on the eyes and this tube on her lips and would see my sister
transformed into a young woman. She
would play a game with me and put lipstick on me, and I would go around the
house displaying to my sisters that I was like Margaret and making faces and
sticking my tongue out. Margaret once did my entire face, and I looked like a raggedy
Andy doll with bright red cheeks. That
got many laughs.
As
a boy, I did not realize there were two genders. There was no man around the
house. I did not know to stand to pee but acted like my sisters. I laughed like them in a girly giggle. I
pranced round like them walking and swaying my hips. I hid my wee-wee from my
sister's site because I wanted to be like them. I adored my older sisters and wanted to be look
them, walk like them, talk like them.
I
had long curly hair when I was young. In
our early family portraits, you could not tell I was a boy. As in life,
everything changes. Prior I started first grade my mother took me to the
barbershop and had cut off my curls. I cried that night because I did not look
like my sisters. When I started first
grade I was still wearing Joan's hand me down panties and girl jeans, which
zipped differently the other boy's jeans.
I was not aware of the different in how girl's jeans and boy jeans
fasten. My mother did have to buy me boy's
shoes. My feet were bigger than my sisters were, and there was no hand me downs
that would fit.
I
remember when Mary got her first period and how embarrassed she was to have
stained her panties. I overheard my
mommy tell Mary that this was normal that all women will bleed and that it is a
curse, but it allows you someday are a mother, so it is worth the trouble. Mary was instructed how to use a pad and to
be sure that when it was her time of the mount to remember carry them in her
purse. I now realized why my sisters
carried purses.
When
I was in first grade I started to hang out with what I was comfortable, and
that was with the girls. I played hopscotch, did the jump rope, and the hand
clapping and chanting with the girls. I
had the chance to play softball, tag, or other boy's games, but I preferred to
sit with the girls and watch. When I did
play softball, I through the ball like a sissy and everyone laughed. As I advanced through the grades, I became
aware that I was different from the other guys.
I did not talk like a guy, I did not walk like a guy. My clothing was
different the other guys. I remember
telling my mother when I was in third grade that I was differed from the other
boys because I was not dressed like them.
My mother took me out shopping for my first boy jeans, but I still wore
panties. I was nine.
Going
into the fourth grade, I was being teased by the guys for playing with girls. It
did not take me long to understand that it was better to be alone not playing
with the girls, or not playing with the guys. The teasing was reduced. Starting the fourth grade, I found my best
friend, Billy an older boy who was left back a grade. The school he was from was not as advanced as
ours was. Billy's reading was not good causing him to have to repeat the fourth
grade. He was new at our school, and I was alone, so we became friends. I was ten and Billy was 11 and half. Another reason we became friends, Billy
protected me from the others because the way I talked and acted. I helped Billy to read. What I did was to read to him, so he could
answer the questions in class the next day.
Every day after school we would spend time playing in the woods in an
undeveloped part of town. We found a pond and sat there in the early spring
reading about history and science. The
first day in the woods, Billy said he need to take a leak, I did not know what
this meant as Billy stood up and walked to a tree. He was in plain sight, and I watched him pee
on the tree. I never saw man or boy do that
before, and it is something I remember to this day. Billy asked me if I needed to take a leak, I
said no. The next day the same thing
happened, this time I decided to do what Billy did. For the first time in my life I stood, like a man, to pee. It was wonderful. We both stood there pissing on the same tree,
our streams crossing and seeing who could pee higher. Of course, Billy could because he was taller
than I was.
It
was when I was standing next to Billy peeing, Billy noted that my underpants
were pink and did not have the opening where you would slide your wee-wee
through to pee. I had to lower my
panties and hold them down below my balls in order to pee. When we were finished, peeing Billy asked to
see my underpants and not know why, but without hesitation, I dropped my jeans
to reveal my panties with lace around the legs and the waist. Billy showed me his underwear, for the first
time I realized there is a difference. I joked with Billy and said that if he
wanted I could give him a pair of panties and he could look like me. We both laugh at the joke. The next day Billy gave me a paper bag with
some of his old underwear. I was excited and please that I would be dressed
like him. I wore Billy's underwear
during the week, but there was not enough to go the week so by the weekend I wore
panties again.
Billy
noted that I tossed the ball like my sisters.
One day down by the pond, he brought two gloves and a baseball. We spent the afternoon playing catch, it was
not long that I had a good arm in throwing the ball.
In
the woods, we did guy things played cowboy and Indians, cop and robbers and
army. I made sure that we did our
reading assignments, so Billy would not get in trouble at school. We even skinny-dipped in the pond where the
water was cold and out wee-wee, and balls would shrink. Then as we lay in the sun drying off allow
our wee-wee to return to normal size.
Billy being about 18 months older than me was taller than I was. He started
have some pubic hair start growing around the top and sides of his wee-wee.
Being
older Billy had and a sex discussion with his father and he shared some of the
sex details with me. I did not
understand all that he told me especially about how the wee-wee would slip inside
the girl and nine months later, she has a baby. Billy had an older bother and
no sisters. I told Billy all I know
about my sisters, how I saw them naked and knew that they had a period every
month. Between the two of use, we had a
good understand of the differences between a girl and a boy.
I
was in the fifth grade, eleven years old when I woke up and thought I had wet
the bed because I was wet between my legs and there was a wet spot on the
sheet. I must have woken my mother up,
and she came in to clean me up and change the sheets. I was to embarrass to ask what happen and
went back to sleep. The next night it happens
again, and I asked my mother what was happening. She said I was growing up and that my body
was changing. I got the sex speech that
Billy had told me a year early, he left out about wet dreams. My mother had
some advice for me. My mother told me
that before bed if I did not want to have a wet dream to play with my wee-wee
and I would cum where I cold avoid having a wet dream. I tried that a few times and it took a long
time to get off. I did not have anything
to help me visualize about jacking off. I did not know how to have sex with a
woman. I did not look woman as sex
objects. The next morning at breakfast,
I told my mother that it had taken me a long time to “ejaculate”. My aunt was standing there and reached under
her skirt, pulled off her red panties and tossed them to me. Her panties were warm, smelled of perfume and
were silky with lace and bows. She said
to rub this on your wee-wee, and I would come faster. I put the panties in my draw with my hand me
down panties, next to my boy underwear and now my first pair of woman
panties. My mother just looked at her
sister with a look like, "why did you do that".
I
thought of my aunts panties all day and could not wait to go to bed. That night as I lay in my bed, I wrapped my wee-wee
in the silky panties and started to stroke my little wee-wee. It was an amazing feeling, much better than with
my hand. In five minutes, I had exploded
in the panties keeping the mess contained and not wetting the sheets. The next morning I washed the panties out and
hung them up in the shower just like my sisters. When I arrived home after school, I went in
the bathroom to recover my frottage, but it was not there. I thought that one of my sisters took my
panties, I was angry. I went into my
room, open my drawer to find the panties folded, and place next to my other
panties and there was a second pair just like the fist but black.
I
went to bed early just so I could cum and feel so relaxed after my climax. I had loads of cum in the panties. Instead of
waiting to wash them in the morning, I did it that night. The next morning they were dry, returning to
my drawer.
If
the weather was bad, we went to Billy's house or to the library. It was a few days after my first wet dream, I
told Billy about it. I told him what my mother told me to do. Billy got a smile on his face and told me
that he had been jacking off for over a year.
He asked if I wanted to see his brother's jack off magazines. I said sure.
We went into his bother room and under the bed were several magazines
such as Hustler. The pictures were as
graphic as you could want to see. I could see what a pussy looked like. Up to this time, all I saw of my sisters was
a slit and their pubic hair. Now I saw everything. We sat on the floor looking at every picture
and every ad for sex.
Billy
was rubbing his crotch looking at the photos, I was aware that I was hard and
felt the need to rubbing my wee-wee. I
had seen Billy's cock many times in the woods when we pissed or when
swimming. Billy said, "You have a wee-wee
because you are small. I have a cock
because I am big." I felt embarrass
because he kept referring to my wee-wee as small wee-wee or little wee-wee. We
sat there looking at the magazine commenting on the size of these breasts and
look at that pussy. Billy unzipped his
pants and pulled out his cock. I was surprise, Billy's cock was erect and huge. It was three times as large as mine was and
very thick. I measure my wee-wee, and it
was one inch when I was ten, two inches when I was eleven. One day I knew I
would be as large as Billy. His cock was
thick too with the head exposed being bright pink. He said he was “circumcised”. Billy said that
some boys had the extra skin that slides over the end of their cock. He said that they Jewish boys when they are
thirteen, the extra skin would be cut off.
We looked at each other and said “ohooooo” at the same time. I took out
my little wee-wee, felt a little ashamed but Billy said that in a year, I would
be as big as him. As we looked at the pictures we Billy rubbed his cocks, I
rubbed my wee-wee. I watched Billy touching
his cock, I would do the same with my wee-wee.
I was being a copycat to his every move.
He started to cum. He squirted a long squirt of white liquid a good
three feet that landed on my arm. It
felt warm, wet and was sticky gooey. The
next squirt was off to one side and landed on my leg, the third squirt did not
go as far and landed on my feet. The
sight of seeing Billy come was so erotic that I came and my cum shot all over
the hustler magazine, causing Billy to say “shit”, got up and found some
tissues to clean up the mess. The one picture was ruined,
Billy he tore it out of the magazine. He
gave it to me and told me to toss it out on my way home. We cleaned up the room, our mess and went to
Billy's room. We did not say much about
what we did in his brother's room. I read to him out the next day's reading
assignment.
That
night I reached into my pocket and pulled out the hustler picture that I was to
toss. I now had panties and a picture to jack off to and came quickly. Before it had taken me over a 15 min to come
and now with the photo and panties, I could shoot my load into my silken
panties in two minutes.
The
weather was bad the next day as we ended up at Billy's house and in his brother
room looking at the jack off magazines.
This time there was one magazine called SheMale and had a photo of woman
with cocks. This was confusing to me. Billy
said some people were neither men nor woman but were shemale. The pictures were exciting and still confusing. The SheMale did not seem to have a slit like
a woman just a cock and balls with big breasts. Billy started to jack his cock.
I started to jack mine. I notice that his cock was all shiny and that
some white fluid was dripping out of his piss hole. He said it was pre-cum and that he used it to
lube his cock. Being younger, I did not
have any pre-cum yet. Sensing that I needed
something to help me jack, Billy said I could have some of his. He moved closer as I held out my hand. Billy
squeezed a drop or two of pre-cum out of his cock. I rubbed it on the head of my cock. With a few stokes, I started to cum. I had a tissue in my hand so did not create a
mess as I did the day before. The touch
of Billy’s pre-cum in my hand, and lubing my cock with it was sensual. Billy gave me his pre-cum, I accepted it as
something special. After I cam quickly, Billy continues to jack sitting
directly across from me. I did not think
was in the line of fire until he exploded and this time it was not on my leg,
or arm. The first squirt hit my face, it was warm, wet gooey cum. The second squirt
was on my chin and neck and the third squirt on my chest. I was a surprise at how quick it happened. Billy
was watching to see my reaction. Billy
said he did not mean to cum on my face and smiled. I remember the look in his eyes, it was the
look of pleasure or satisfaction having hit my face. I smiled back with a look
of acceptance and giggle like a girl. In
a strange way, I felt I should be the one to receive Billy’s cum. We were the best
friend and having him squirt his load on me was just a benefit of our
friendship.
It
was the weekend, and all my boy underwear was dirty. I could wear my pink
cotton panties or could try on my silk panties.
I selected the black lace panties. They felt sensual touching my wee-wee,
my wee-wee sliding up and down inside my panties, my wee-wee was semi erect all
the time. I knew I was aroused all the time and knew if I touch my wee-wee I
would cum quickly and would be rewarded with that wave of sexual feeling. It was Saturday I had finished my chores. I
hurried over to Billy house, so we could play again.
Billy
greeted me with a big smile on his face; we got a couple of Cokes out of the
refrigerator and sat in the den. We were
watching TV, nothing special, flicking the channel seeing if there was anything
interesting to watch. It was Saturday and many cartoons but nothing
interesting. Billy asked, “What do you
want to do?’
I
was hoping that we would go to his brother’s room but did not want to suggest
that so said, “I do not know what you want to do?”
Billy suggest that we go to his bother room. When we were not in his brother’s room looking
at the magazine and playing with our cocks, Billy did not talk about what we
did. It was as he was a different guy. When we were in his bother room and looking at
the magazine, we always were jacking. He would joke with me, would tell me
fantasies about how nice it would feel to slide his cock in a real pussy. He
would tease me and said, “Matt you have a tiny wee-wee it would never slide
into a pussy. You are going to have to
use your hand until you have a real cock.”
I
would laugh and say, “Oh This time when started to play I took off my pants to
show Billy my black lace panties. He
just stared at them and said, “Cool, cool, so cool”. He even reached out and touched my panties to
feel how smooth they were. I was sure
this was the first time he every saw woman panties before, I smiled and was a
little excited about showing off my secret. Billy was looked at me dressed in
black lace panties and asked me to take everything off but the panties. I had a very white and thin body, not a boy
shape but more on the feminine side. He
said, "Matt you look very sexy, I want to come on you again."
I
protested by saying, “Oh, that is yucky.”
Billy
replied, “Come on your little pussy, you can wipe it off. I want to see how far I can shoot and hit a
target. Smile you are my target.”
I
could tell that Billy was not going to take no for an answer. His cum would not be on my face long. I could
wipe his cream off my face. It was something for me, I could not say no. Besides, I did not know why but I wanted to
see him squirt again. I wanted to watch
him play with his cock and then wanted to see him cum. I agreed, “OK, but only this one time and I
will wipe it off, ok”.
Billy
said, "Lie down and rub your panties.
Pretend you are a girl. Pretend you have a pussy, rubbing your pussy."
I
reclined on the floor looking up at Billy, "like this?" I tucked my wee-wee
between my legs and rubbed the area. I
was naked except for my black panties, at my age was flat chested, skinny, and
looked like my sister. All I needed was
my long hair. I am sure that Billy saw me the same way. Billy stood over me jacking his cock as I
looked up watching. I had a fascination
in watching Billy for several months we played with our cock, with me copying
his hand action finding the best way to come.
Sometimes he would grab his cock in his hand and touching his forefinger
and thumb together making a ring and with the other three fingers, he called
his pussy hand. Sometimes he would rub his
cock with one finger around the head of his cock, then tickling the area under
the head. Sometime he would put both
hands together and move his hips in and out and he would hump his hand. Billy
would start jacking his cock faster it would get very hard, and the head would
turn from pink to purple. He would yell, shooting his cream all over me. The first few times his cum went all over and
did not land on my face, but with some practice, he could aim and hit my
face. He took such pleasure in seeing
his cream on my face and dripping down my chin. When we were in his brother's room,
he would call me Cindy. I asked him why
and he pulled out one of the shemale magazine and opened it to a page where the
girl was named Cindy. Billy said I
reminded him of her. When we were
playing, he called me Cindy and I enjoy my feminism name. When we were not jacking our cocks we were
just two normal guys and Billy would remind me to sit with my legs open and not
together. He would tell me that I needed
to walk like a guy and even told me to talk like guy. I developed two different
ways to act around Billy, straight acting Matt and girly acting Cindy. I was Matt most of the time when around
Billy. I did look forward to be Cindy. I
enjoyed my guy time with Billy. I liked my Cindy time with Billy, so I could climax.
Billy
asked me if I could bring next time a training bar to wear. He told me, he
wanted me to be dressed more as he wanted a girl. I know that I could find a training bra
somewhere and bring it the next day. It was Saturday again, I put on my red
silk panties and the training bra, next my outer clothes. No one could see I was Cindy underneath and
Matt on the outside.
I
took my Matt clothes off and show Billy my red panties and my white training
bra. He said, "Cindy you fucking
bitch. Here is something I got for
you," as he handed me a paper bag.
I opened it up and saw hair, Billy had found a cheap costume wig for
me. It was shoulder length, blonde and
had curls. I put it on and looked in a mirror;
I looked just like I did before my first haircut. I looked like one of my sisters with the
curly blonde wig, the training bra and the red silk panties. Billy said, "Damn, Cindy you are looking
good." Billy patted my rear.
"Walk around for me," as he took out his cock and started to
stroke his erection. I pranced around
the room, swaying my hips and using my arms to talk, my wrists were limped. I said, "Oh Billy, you are so silly. Do
you like my outfit? I got it just for you. Oh my, Billy that is a big cock you
have. Are you going to cum for Cindy?
Billy my man."
Billy
said as he stood up, "Get on the floor you fucking bitch, lie on your back"
I did as Billy told me. With that, Billy
straddled my body with his legs, knelt down, he was sitting on my chest. In
this position, I could not move and felt helpless. Billy's cock was just inches
in from of my face. He leaned forward rubbing his cock on my face, slapping my
face with his hard on. It hurt a little,
and I wanted him to stop, but I did not say anything. Billy in a low voice, "Oh Cindy you are
so pertly, and your skin is so soft. Do you like feeling my cock rubbing your
face you? Cindy you are my bitch?"
With that being said, he shot his wad on my face and did not miss, I was
covered from forehead to chin. Billy was
off of me, looked at my face with his cum all over, he smiled with pleasure and
told me to go are cleaned up. I returned,
the magazines were put away, Billy was not in the room. I still had a hard on and wanted to cum but
got my Matt cloths. I put the wig back in the bag and went to
find Billy in the den watching TV. I
handed him the bag with the wig, and he told me to keep it, bring it when you again
come tomorrow.
That
night I went to bed, and with the lights off and alone I rubbing my cock with my
panties and had a great big load and a warm feeling of well being. As I closed my eyes thinking about Billy with
his cum all over my face, I felt satisfied. I also enjoyed Billy calling me his
fucking bitch. I liked that.
Each
day of the week, I would go to Billy's house.
We would grab something to eat, watch TV and Billy would lean over and
tell me to go up stairs. That was my
clue to get dressed as Cindy. Billy
quite watching me get undressed only entering the room when I was dressed as Cindy. He would enter
his brother's room and say, "Cindy so nice that you could visit me. You look hot today." Today I had a surprise for Billy; I have
stuff the training bra with tissues to give me the looks of breasts. Billy responded by saying, "Wow, Cindy
you have tits. You look better every
day." With that, he reached out and
touched my fake tit, rubbing his hand on my chest and then holding me close to
him. I could feel his hard cock against
my body. Billy said, "What do you
want baby, you want my cock?"
I
responded in a frail, feminism voice, "Oh yes Billy."
Billy
said in a demanding voice, "Well go ahead take out my cock you little cock
bitch." I got on my knees, keeling
in front of Billy, I unzipped his jeans and fumbled with is cock and finally
freed it. This was the first time that I
had touched Billy's cock. I felt strange
and different. I could feel that his
cock was warm, that his cock was hard and that his cock was silky smooth,
almost as smooth as my panties. My
fumbling with his cock must have been a turn on for him because as soon as I
got his cock out he shot his load on my face. I looked up at Billy and could
see a smile on his face as he wiped his cock across my face getting cum all
over his cock and my face. Billy said,
"Go get cleaned up your fucking cock bitch. You did well today."
I
went to the bathroom, looked in the mirror, and saw my face. I loved the wig and curls. When I saw all of that cum on my face, I
smiled. I rubbed it on my face and not
know why I licked my hand tasting Billy's come for the first time. It was salty and not unpleasant at all. I smile at the girl in the mirror and said to
myself, "Cindy you are lucky to have a friend like Billy."
When
I return Billy was gone, I dressed as Matt and went down stairs. Billy got me a
coke from the refrigerator and asked, "What do you want to do?"
I
responded, "I do not know what you want to do?"
Billy
said, "Let's go the Mall."
Walking
in front of a dress store Billy stopped. Seldom did he say anything about our
dress up activity but this time he did.
Billy said, "Tomorrow I want you fully dress like that," as he
nodded to the mannequin in the window dress in a blouse and skirt.
I
responded, "Sure Billy anything you say." I knew that I could borrow some of my
sister's clothing. I went home that night, and while my sisters were cleaning
up after dinner, I went into Joan's rooms. I went into her closet, and quickly
found a skirt and a blouse. I tried to find one that I did not remember seeing wearing.
I hoped she would not notice they were missing.
The
next day I went to Billy house, he told me to go on upstairs he would be up in
a minute. I got dress as Cindy. This was the first time for me to be fully
dress. I enjoy looking into the mirror admiring my legs, the skirt and blouse
and of course my curly blonde wig. I
looked like my sister Joan only taller.
Billy entered the room and immediately got a smile on his face. Billy
said, "Cindy you are so sexy fully dress, I want to see you like this
every time." I stuffed my training bra again with tissues and with the
blouse I borrow, it was somewhat tight.
The blouse stretch over my training bra giving me the illusion of nice
tits. Billy said, “Cindy get on your knees.” He moved, so he was standing in front of
me. “Take my cock out,” he ordered. I did as ordered. “Now, play with my cock
Cindy.” This was only the second time that I touched Billy and was not sure
what to do. I know how to play with my wee-wee,
and I have watched Billy play with his cock but to touch his cock was different.
I grabbed his cock with one hand and slid my hand up and down. Billy moaned softly, “Yea baby, just like
that, you are doing fine.” I was amazed
at feeling Billy’s cock in my hand how warm, smooth and hard he was. I stopped and rubbed with my finger the area
under the head and got a response that I was tickling Billy, I giggled like a
girl. Billy started to moan again and
started to move back and forth in my hand until in a second, he exploded. I aimed his cock to my face and got a face
full of his wet hot cream. Billy looked
down seeing my face covered with cream said, “Oh Sweet Cindy that was the best ever.”
“Now go clean up.” I went to the bathroom,
looked in the mirror, and enjoy seeing Cindy looking back with Billy’s cream on
my face.
We
did not meet in the woods any more; I could not dress as Cindy there. Billy and I continued to meet after school
and on Saturday. Each time we met in his
brother's room, Billy would think of something new or different to try. I was now all about Billy and Billy
coming. Billy did not want to see my wee-wee,
I hid it just like when I was at home. I
did not think our playing was odd or wrong. It was like when we played cops and
robbers, or cowboy and Indians. I was
pretending to be a woman, and Billy was playing himself, a horny teenager. We continued to play the rest of the fifth
grade. Now I would give Billy a hand job
while dressed as Cindy. Each time he
wanted to see is cream on my body. I did
not think this was a gay activity. We were just playing.
Beginning
the six grade, I was now 12 and Billy was thirteen and a half. His had fully developed pubic hair and
bragged that he was saving at least once a week. His cock got larger and thicker, I enjoyed
feeling him get hard in my hands and coming when I jacked him off. I got a reward when I did a good job. I did not cum when I was with Billy but had
to wait until I got home. I could
visualize Billy, his cock and cum all over my face and that help me when I used
my silk panties. Over the summer, I grew
three inches taller, my wee-wee got bigger.
At
the start, of the sixth grade and one day when I was Cindy playing with Billy’s
cock I said, “Billy, can I show you my wee-wee?”
Billy
looked at me wired and said, “Sure Cindy show me your clitty. That was the first time he had referred to my
wee-wee as a clitty. So I pulled up my skirt, pulled down my panties and revealed
my wee-wee. Billy smiled and said,
“Cindy I can officially say that you do not have a wee-wee anymore. Matt you now have a cock, and as Cindy, you
have a clitty. Now make me feel good and
slide your hands up and down my cock. I
did as I was told having a big smile on my face. I have finally grown up and now had a cock and
Billy was my friend who helped me be Matt when in public and helped me be Cindy
when we were in private.
It
was around Christmas time, I had dressed up as Cindy for Billy. Billy entered
the room and said, "I have a surprise for you. I found this porn tape that you need to
see." Billy turned on the TV and
started the VHS play. The porn movie
started where Billy had left off. It
showed a guy sitting down who was very naked and that a woman fully dressed was
kneeling. The man's cock was in her
mouth. The camera angle changed to show
a close up of her taking the head of his cock into her mouth. Then half of the shaft
and finally he pushed her head down and all of his cock disappeared. The woman gagged and was let up but then
pushed down again gagging. The action continued showing her licking his balls,
sucking his cock until he shot his load into your mouth. She kept her mouth open until he was through
coming. The video showed a closed up of her mouth. She swallowed; open her
mouth to show that all the cream was gone.
I
looked at Billy and said, "You want me to do that?"
Billy
nodded his head and smiled, "You would enjoy it Cindy."
I
protested, "Billy that is gay to for a guy to suck a guy's cock."
Billy
said, "No it not, the video showed a man and a woman having oral sex that
was not gay. That is normal when a man
and woman have sex, she sucks his cock, and it is expected."
I
responded, "But Billy, I am not a woman, I am a guy and a guy sucking a cock
make me gay and I am not gay."
Billy
looked at me and said, "Cindy you are dressed as a woman, when you suck my
cock think of your self as a woman, then it is not gay." "Cindy you are my girl and when we are
together you need to do certain things for me.""Besides no one will
know and if no one knows they will not call you gay."
But
Billy, "I pleaded." Billy looked at me straight in the eyes put his
hands on each side of my face and pulled me close and kissed me on the
lips. His lips were warm, soft and felt
like something I have never experienced.
I
said with a surprise, "Billy."
Billy
put his finger to my lips and said, "Shush." He unzipped his pants
took out his cock and said, "Cindy kiss my cock as I kissed you."
My
mouth was open from the surprise kissed. I was not sure what to think about
seeing my first porn video of oral sex.
I did not want to be gay or do gay things. I had to make a decision and fast. Billy was right, when I was dressed as Cindy
I pretended to be a girl and a girl can suck a cock, and it was not bad. It did not seem to be wrong, and Billy has
been good to me. I said, “OK,
Billy. Just so, you do not tell anyone.
I will do it today, but if I do not like it, I do not want to do it again, OK”
Billy
said, “Sure baby, just try it today. It
will be OK. You can stop at any time if you do not like.”
I
got on my knees, and kissed the tip of his cock. He moaned a little, I
continued to kiss his cock, up and down his shaft, then his balls. I knew I was
teasing Billy, he deserved it for asking me to suck his cock. I kissed the head of his cock and remembering
the video, I opened my mouth looking up at Billy. Billy guided his cock into my mouth as I
closed my lips around his cock. Billy
said, “Ohoooooo my Cindy that feels so good, do not stop.” Billy urged me on by
saying, “Oh you are a good cock sucker.
Use your tongue and thickly may cock.
Yes Cindy just like that.” I was encouraged
by his words. The more he told me what
to do the more I wanted to do it. It did
not feel wrong for what I was doing. I now moved my head back and forth
allowing Billy’s cock to slide in and out of my mouth just like in the porn
video. Billy said, “Oh man, I
coming.” Billy came in my mouth, at
first I felt his cock get very hard and that the head filled my mouth. Billy cum filled my mouth and tasted salty at
first, it was warm, it was thick his cum was all mine. I opened my mouth to show him his cum in my
mouth and then swallow just like the porn movie. I open my mouth to show him that I swallow his
cum then looked at him and smiled. The
taste in my mouth changed to something bitter but still was not unpleasant. I was very pleased with my actions, sucking
my first cock and making a man come. It
was a turn on for me. Just by using my mouth,
I could make a person cum. It was
exciting for me to know that I had this power. I also knew I would do this
again for Billy. I realize I was the one with control over
Billy climax. I could make it last a
long time or move my head faster and get him to cum sooner. I would decide if he would cum on my face or
in my mouth. I was in control, and if I
said no, Billy would not cum at all.
About
Easter break, I was dress in my sister short skirt and white knee-high
stockings and white school blouse. I
could have passed for any girl in the six grade. Billy gave me a bag that has some pantie
hose. I have seen them many time hanging
in the shower, have touched them but never had I put them one. Today Billy gave me a pair and told me to try
them on. I did and enjoyed how smooth they felt against my body. I pulled them
all the way up my legs and wiggled my bottom to get into the pantie hose. I turned around showing off my legs and rear to
Billy who just smile and rubbed my legs and my rear. He showed me another VHS tape and said that I
will enjoy this action. This time it
showed a man and a woman, she was on her hands and knees. He was kneeling
behind her. He was moving forward and back
as she was moaning. Billy said,
"Cindy she is in the doggy position and he is fucking her.
I
responded, "Billy I do not want to do this. I do not want you to fuck me."
Billy
smiled and said, "Silly Cindy, I do not want to fuck you, I just want to
slide my cock between your legs, so I can feel how smooth the pantie hose are. You keep the pantie hose on and will be
safe." "So Cindy get on your
knees bitch."
I
was not sure about this, but if I kept the pantie hose on, I guess it was
safe. Billy always got his way. I would say no, then he would convince me
different. Knowing that Billy would get
his way, I said, "OK Billy, but no fucking me." I got on my hands and knees, looking up at
Billy. I said, "You mean like this?" As I assumed the position. Billy moved to behind me.
Billy
said, "Cindy, put your legs together, so I can slide my cock between your
legs." I did as told and
waited. Billy rubbed his cock up and
down my crack and finally sipped it between my legs. He then proceeds to move his cock in and out,
sliding between my legs. His cock was
rubbing against my balls and my cock, exciting me. I knew that he was not fucking me, but it
felt good anyway. Billy was holding my hips pulling me back on his cock. I wondered what a woman felt when she was
fucked by a guy.
Billy
fucked me faster and then came all over my pantie hose. I knew I was going to have to wash them
before the next day. Billy patted me on my backside and said, "Cindy you
are such a good girl and you have such sweet legs." I was glad we
pretended to fuck, and pretending was exciting for me. I did feel like a woman in the porn
video. Over the next few weeks, Billy
would put me in different positions trying to find one that would excite him
the most. He had me on my back and put
my legs on his shoulders. He told me to lie
on my stomach, allowing Billy to get on top.
He did it standing up and even allows me to sit on top of him. I like that position a lot because I could
decide how much of his cock would slide between my legs. Some time it was just a little, gut the head
of his cock. Other times I would slide up and down to stimulate his entire cock
shaft. He bent me over the couch, the kitchen table; he fucked me in every room
of the house.
It
was near the end of the school year and the six grade that Billy told me that
his Father got a job in another town and that he would be moving when school
was out. I could not believe what Billy
was saying, my very best friend, the one that protected me from the other guys,
my friend that told me about the birds and bees, my friend that I let come in
my mouth. That night I cried, cried for
my lost of my best friend. I did not
know what I would do that summer and did not want to think about going to Jr.
High School without someone to protect me.
On
the last day of school, I shook Billy's had and stood tall as he told me. He called me Matt, leaned forward, and said,
"Cindy, I will never forget you and you keep being Cindy when you
can." He winks at me and said
goodbye. It was years before we saw each
other again.
I
was not in the seventh grade 13 year old and had to make some decision. First,
I decided that I was not gay and that need to be Matt. I decided to quit wearing my silk panties and
my mother had bought me boys underwear.
I was a smart guy, always had good grades and knowing I would figure out
what I was going to do.
In
the seventh grade, you had gym class and had to take showers with the other
boys. I did not mind because I had a respectful size cock. I did compare with the other boys, and I was
one of the larger one there. I also
started to get my pubic hair my voice lowered, and I learned not to giggle like
a girl but like a boy. I pissed at the
urinals but at home had to remember to sit down to pee. I did not jack off every night and did not
have any more wet dreams.
I
was still a loaner at school, but no one picked on me, Billy taught me to stand
up tall, and not to take crap from anyone. I got through seventh grade without
any incident. Billy would send me a letter now and then said that school was
not same, but he found a girl to read to him and put a smiley face.
I
developed into a young man. Graduated high school and had a scholarship to a
college a couple of hundred miles away from home. I had complete freedom but had a
responsibility to keep my grades up. To make a little extra I had a job in the
local bookstore where I met and knew many of my classmates. One day I over heard two freshmen girls talk
about makeup and about putting on lipstick.
I could not help myself and told them to forget the lipstick and to use
your blush and then clear lip-gloss.
They looked at me and said what I knew; I smiled and said, six sisters. From that time on, I would give out advice on
clothing, makeup and dating. While I did
not have a steady girl to date, I did meet a few my first year at school. I
found them to be very dull and not able to carry on an intelligent conservation
or so stuck on them selves that I considered them high maintenance.
