How I became a transvestite

My life as a youngster was a troubled one...

My troubles started when my sister came home from the hospital.
I was about three.
My parents toled me I am getting a brother and I was over the moon about having a little brother to play with...

When my mother took of her nappy for the first time... my mind fractured... I was expecting my brother to look like me! the only words I could muster was, "Where is his to-lie!?"
Some where deep inside the back of my mind something bad happened: I couldn't understand why my brother didn't look like me, Did it come later? was his dick still at the hospital?

My parents just laughed and explained that this was my sister... She has a flower...
That simple... she had a flower and I had this thing I have to pee with...
why couldn't I have a flower too... I mean like she has a flower, something beautiful and fragile, I had this dirty tittle to-lie that the fore skin didn't look quite right and it made an unsightly bulge in my pants, especially when I didn't whore underpants.

I began wearing her diapers... I supposed in my little mind I figured that if I took myself back to being a baby, I could somehow make a different decision and also have a flower.
I wet my bed a couple of times hoping my mother would buy me my own diapers and spend the same amount of time pampering my bum with baby oil and powder.
Somehow I felt cheated, I didn't remember being treated with such care...

As time progressed my sister was always treated different than me... I got hidings, my sister got new frilly pink dresses and pretty make-up...
I would sneak into her room from time to time to try on her new dress and panties, I was always a bit bigger, but took care not to stretch or tear anything.
We played together, dolls and lego... I never really took to cars and my first friend was the girl across the road.

She was just as much a girl as my sister, but I never got the chance to get into get panties... like wearing them ;) or other wise...
When I got to 1st grade she introduced me to her boyfriend... I was so mad. I just wanted to fight with him, but he was kind enough to suggest we be friends rather... so we became friends... If I couldn't be her friend then he'll have to do I figured.

Me and him played together all the time, he also had a pretty little sister one year older than my sister... and to my delight they became friends too. She took a fancy to me and one day pulled me under my sisters bed and suggested we kiss... ;) my fist kiss... under my sister's bed.

Me and my friend use to cycle in the bush quite a bit and one day we stopped on a hill deep in the bush. He said we should make a friendship pact... We had to touch dicks and bump asses... It seemed a bit odd, but we were only like seven so I agreed and there in the bush I had my first experience with another man... It felt considerably more pivotal than the kiss under the bed, but my dad made a point of it to educate his only son not to like other boys more than girls.

Needles to say I regressed the thought of having a sexual experience with another boy and forgot about it... till now I suppose.

When I was about eleven a new boy came to school.
He was a good looking lad and he had all the girls running after him within weeks...
I felt something awaken in me... the key to having a girlfriend for real was in site and this boy had it.

We became friends... we spoke about girls and sex all the time ;0 our hormones was to blame.
One hot summers night we pitched a tent in his back yard.
We skinny dipped that night.
Later in the tent I asked him if he wondered how it would be to be with a girl...
I suggested we try out each others bums to feel how it would be...
So there I was, gently placing my dick between his ass cheeks...
We lied like that dead still for about thirty seconds, then it was his turn...

Later that year we received sex education. The teacher explained to all the twelve year olds, girls and boys separate, what sex was all about... eventually the teacher came to homosexuality and explained to us what it was all about... Me and my friend took one look at each other... we were just experimenting... but we had sex with each other at the age of twelve... My second sexual experience was with another boy as well... This time I made a casual joke about it with him. I even toled another friend that he suggested we do it like that, but deep inside I was getting worried...

Then my sister got her first training bra...
I looked at my mothers bra's and panties often when they were in the wash, but they were old fashioned and way to big for me at that point... besides, what boy wears his mother's underweare... your sister's underwear is ok, but not your mother's...
I was ecstatic... I couldn't get enough of my sisters cloths and they were really interesting now...

At the age of 14 I had many erections... the first one was when I wore my sisters diaper, I was three at the time, but I haven't had an orgasm yet...
I confided in another friend since I didn't see the point of masturbation...
He looked at me in shock for a second then smiled and said: just carry on doing it till it happens...
Till what happens I asked. He just smiled and shook his head...

So that after noon I raced my bicycle home... I was going to be alone for one and a half hours since my sister had netball and my mother had lectures.
I made a bee-line for my sisters room and slipped into a light brown training bra a pretty pink shirt and a white pantie...
I completed my attire with a pretty bracelet on mu right wrist.

Rock hard as I went down on my knees, I started stroking my dick...
at first it was nothing, then I got the feeling I wanted to pee...
I fought of the urge to stop and kept going...
Then it happened: the fracture in my mind cracked again.
I came for the first time looking down at the bracelet on my right arm, scared as hell that I was going to pie all over the place...

Little did I know then what happened to me, but after that it became a ritual.
Night after night I would take "extended" showers.
First dressing in my sisters cloths from the wash basket and then whacking off...

I toled my friend, the one I slept with in the tent that I came hard and if he wants I will show him. hehehe he was all to willing to watch me as I undressed and started to stroke my self...
There I was, naked on my knees in front of my best friend cumming just for him...

Once I asked him if he would ever wear panties under his pants and go out...
He replied he would be to scared his pants fell down ;)