Storyteller
- 2 years ago
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My Story free porn video
A little about myself: Me and "Brittany"
Hi, my name is Brian and I am 16 years old. Since puberty I have had
interest in girl's clothing. At first I just thought I was enjoying the
girl inside of the clothes. When I reached 8th grade I realized that
this was not the case. I began experimenting with my older sister's
clothes at the beginning of my 8th grade year. First it started off with
just sweaters and shirts but it eventually got "out of hand" but before
I divulge my escapades, perhaps you should get to know me a little
better.
As I said earlier, I'm Brian and I am currently 16 years old and in the
10th grade. I am a bigger kid, I matured at a young age compared to my
male peers, Weighing in at 180 lbs and 6 feet tall, its obvious that I
don't appear wussy at all. That coupled with my Italian-Polish heritage,
I have pale skin and a lot of hair on my face and rest of my body. I
have brown curly hair that is usually in a mess, I keep it short for the
most part so it doesn't become an afro, but I digress. I have never been
good with the ladies, I rarely ever have decent conversations with them
beyond school work. I am an average student, my parents say I could do
better if I didn't spend so much time hanging out with my guy friends
and playing video games. Anyways, I have never been athletic despite my
size advantage. I wrestled in middle school but that was a little too
aggressive for me. See, I don't like hurting people and I feel bad when
I do. This feeling will have a major impact on me later on in this
story. So, now that you know a little about me we can begin this tale.
Like I said, I realized that I was interested in girl's clothing shortly
after puberty. I was always curious as to what the girls felt like in
their short skirts and high heels with makeup all over their face. Since
I have never really been a "looker" by male standards I suppose, I
envied the way they seemed to attract people. After countless rejections
in middle school for dates, I became lonely. I somehow came to the
conclusion that since I could not get a girlfriend, I would become my
own in a sense. Instead of having a girl to talk to, I just began
thinking to myself, imagining what it would be like to be a girl. So,
this ultimately led me to start experimenting with crossdressing, at
first it was innocent stuff, I would just wear my sister's sweater or t-
shirt over mine. It was simple stuff.
As I got older, I got more into it, eventually wearing the dresses and
skirts that my sister possessed. Fortunately for me at the time, I
hadn't really put on a lot of weight, I was still in the 180 lb range,
but it was spread out, so I could easily fit into my sister's clothes,
albeit they were short on me. This carried on for a while, then I
started getting into the makeup, oh dear that was a mess. I stole away
some of her less "important" makeup one day and tried it all out. I kept
poking myself in the eye with the eyeliner, and mascara was tricky
because I didn't want a member of my family to return home and notice. I
was good with lipstick and eyeshadow though, so when I would get dressed
up, I would stick with that. After a certain point, I decided to try the
underwear. I was a little apprehensive at first because I thought my
sister would notice that her bras and undies were misplaced. However, I
did it anyways, kind of excited about the possibility of her finding
out. My favorite pair of undies were pink with a cute bow on the front.
I like these because they were bigger and concealed my manhood better.
The bras were trickier, but I was able to get them on with no problem.
In the middle of 9th grade I evaluated my situation and realized what I
was doing. I started brooding over my choices and was ashamed of myself.
I had even gone as far to make up a fake name for myself, Brittany. Up
until this point I wasn't really a religious boy, but this really made
me break away from god forever. At first I was concerned that God would
cast me to hell forever with all of the heathens and sinners. But then I
came to denounce my faith. I became obsessed with crossdressing at that
point now that there was no moral conflict, which later my doctors would
tell me that I suffer from OCD (Obsessive Compulsive Disorder) but more
on that later.
As I grew increasingly ashamed of myself but could not put a stop to it,
I finally snapped one day in class. I started shaking violently and
sweating. The girl sitting next to me yelled that I was having a seizure
and I quickly quieted her concern. The teacher noticed my behavior and
sent me to the clinic. I called my mom, not knowing what to tell her. I
simply told her I had a panic attack. At that point I had decided to
come clean with my mom (I will NEVER tell my dad, it would kill him to
know that his son was/is a "pussy"). I told her we needed to talk in
private. She sent my older brother to come get me. On the way home I
told him everything. By the time we got home I was sobbing
uncontrollably. Later that evening I talked to my mom. I told her the
same stuff that I told my brother.
I could tell that it was killing her on the inside. I felt so ashamed of
myself and didn't know what to do. I turned to drinking over the next
few months to try and escape the issues. After confessing to my mom, I
started going to a psychiatrist and psychologist. They both diagnosed me
with OCD and said that my reasons for crossdressing was that my
overactive brain was telling me to crossdress for some reason. At first
I believed them, but then I realized it was a lot of bullshit, since
there was no reason for my brain to be telling me to do something as
random as crossdressing. I concluded that it was a personal choice but I
continued taking my meds over the next few months. They obviously didn't
help because I eventually went as far as to shave myself hairless
(except the head of course) and steal an outfit from my sister.
This was the most extreme thing I had done. The outfit entailed black
stockings, a short jean skirt, the pink panties, a pink bra and a white
button up blouse. I had acquired a few hair clips over the months from
random places my sister left them. At this point my hair was long and
poofy, but when wetted or gelled it was about halfway down my neck. I
hid all of these things in a brown paper bag underneath my bed. I kept
these things there for several weeks. I wore the panties under my jeans
a few days to school and I wore the bra (not stuffed) to a hockey game.
Eventually the panties got dirty and I couldn't wash them any more
without my mom noticing.
I took one night they were gone, got completely dressed up, but the
clips in my hair to keep it from getting all poofy again and put on a
headband. I put on some blush, lipstick and eyeshadow. I didn't have any
shoes to wear since I wear a size 12 in mens. I paraded around the house
acting like a proper young lady, crossing my legs and repeating whatever
I saw on TV in my most feminine voice, which sounded good, in my
opinion. I caught a glimpse of myself in the mirror, and at first I
thought I looked like a pretty girl (albeit a few inches taller than a
normal girl.) but then I immediately thought to myself "What are you
doing Brian? You're a guy, your supposed to be wearing a t-shirt and
jeans and playing video games and rough housing with your friends.
I started crying as I walked to the bathroom and got undressed. I took
off the clothes and put them in the bag. I put my boxers and t-shirt
back on and looked at myself again. I still had my hair and makeup done,
and I figured I did look like a girl, and as I took off the make up and
fixed my hair back into its poofy normal style, I wondered if I would be
happier as a girl. Since that night I have not crossdressed again. I
have maintained a balanced life now, blending my feminine tendencies
with my social life. Even though I am still unlucky with girls, I
continue to treat them well and am chivalrous on a daily basis. I used
to try to forget the entire experience, but now I know that it has been
a chapter in my life that has helped shape who I am. There is no longer
any concern in my house about it, my mom and siblings think me "cured"
and I lead a normal life. My friends always tell me to be more masculine
and act like a man, but I don't have it in me. For the rest of my life,
Brittany (my chosen female name) will be a part of me.
Note: This story is 100% accurate. This is not a piece of fiction or
fantasy, it is an autobiography of my crossdressing challenge. I had not
taken pictures, otherwise I would have included them in here. However, I
will soon be writing my fantasy, which you can look out for under my
author's name. Comments/Questions/Concerns are always welcome!
Latisha
- 03.09.2022
- 20
- 0
