Date: Tue, 29 Oct 2013 20:57:24 -0400
From: Andi <SissyAndi@Safe-mail.net>
Subject: Trailor Park CD 01 (Transgender -Teen)

Disclaimer: My stories contain explicit descriptions of consensual and
Non-Consensual sexual activities and are not suitable for reading by anyone
under the age of 18, or anyone offended by reading such material. These
acts include bisexual activity, cross-dressing and other fetishes and
perversions. All characters and events are complete and total fiction and
comes from the twisted and perverted mind of a long time crossdresser.  All
Stories are the property of the Author.  Any feedback would be greatly
appreciated. Thanks.

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Trailer Park CD 01

I am Scott, a 13 year old boy who lives with my mom and my half brother in
a run down trailer at the edge of town.  We live in a fairly large trailer
park.  There are a lot of kids in the trailer park ranging from 6 to 17.
Some are very pretty girls.  My half brother David was 17.  Mom had him
from a previous marriage and then married my Dad, He left Mom when I was 6.

Mom was a single woman but worked hard trying to support two growing boys.
She recently took a job at a run down strip club in a bad neighborhood.
She tried to convince us that she was not dancing but waiting tables.  I
knew better after I fould some of her dance costumes one night while
exploring her bedroom.

She left every afternoon around 6 and never got home before 2 in the
morning, sometimes even later.  She left David and me alone to fend for
ourselves.

I had heard some of the girls in the trailer park talk about how hot David
was.  He was 6'2", still a little thin but he had started to grow a
mustache to match the black hair on his head.  I felt so small beside of
him, then I was just under 5 feet tall, barely 100 pounds.  I had blonde
hair and blue eyes.

David never seemed to have trouble getting a date and I am not sure why.
From what I seen, he was always rude to the girls and treated them like
dirt but the worse he treated them the more they liked him.

I was still pretty naieve when it came to sex, I had not even started
masturbating yet.  All that would change and change in a big way.

It was the weekend before a week before Halloween and Mom said I could have
some of my friends over on Friday night.

So there I was, watching some horror/cheap sci-fi movie with my friends,
Robert who was 13 like me and Art who was already 14.  The community always
had a big party at the local Baptist church and They were discussing what
costume they were going to wear for the party the following week.  They
asked me what my costume was going to be and I told them I had not thought
about it and that I would probably not go to the party.

They told me I had to go because half the town would probably be there.
That is when I told them I did not have anything to wear and that I could
not afford to buy or rent something.

Art got a wild look in his eyes.  "You know you look a lot like your Mom
and she is HOT!!!!  Maybe you could wear some of her clothes and go as a
female."

It was true that my Mom and I were about the same size but most of her
stuff would be tight on me and a shiver went through my body at Art's
comment, I had been thinking about trying on some of my mothers clothes,
especially after I found the dance costumes hidden at the back of her
closet, but I had always chickened out and never went through with it.

Robert decided to add his thoughts to the conversation by saying that My
Mom looked really hot in her sexy little black dress.  I knew the dress he
was talking about and he was right, Mom looked hot when she wore it.

I tried to change the subject but they keep insisting, I finally flat out
refused and I thought they had finally let the subject drop.

At some point during our sleepovers Robert would bring out a dexk of cards
and we would play poker.  We usually played for pennies and I always seemed
to win the majority of hands.

After about 30 minutes of playing for pennies I was down to less than 20
pennies.  Art decided to raise the pot to something I could not afford but
I had a full house,two aces and three tens, and did not want to fold.

So Art suggested that if he won I would dress up and we could see if I made
a passable female.  I wanted to say no but my hand was so good I accepted
the offer. I just knew that I was going to win a huge pot of pennies and
was smiling from ear to ear when I laid my cards on the table.  That smile
disappeared in a hurry when Art showed his hand, how in hell did he get
four kings?

Art was grinning as he scooped up his winnings and he asked me if I had
decided what I was going to try on.  I tried to refuse but they both
reminded me that I had agreed to Art's terms.

I put up a good fight, but secretly I was already hard with excitement at
the thought of wearing Moms clothes.  Even more excited at the idea of my
friends seeing me dressed up.

I finally relented and excused myself.  I easily found the black spandex
dress that they had talked about.  If I was going to do this I was going to
do it right.

I search through Moms drawers until I fould a pair of blacklace panties and
some black panty hose.  I quickly stripped and my hands were shaking as I
slide the sexy panties up my legs.  I sat down on the bed and worked the
hose up my legs like I had seen women do in movies.  The material felt
incredible as I pulled the pantyhose over my hips

I glanced over to see my reflection in the full legnth mirror on the closet
door. I thought that I made a cute maybe even sexy girl dressed the was I
was.  When I stood up there was the slight hint at a bulge in my panties as
my small cock was rock hard and throbbing.

I knew what masturbation was even though I had not tried it before.  I
squeez my cock a few times but stopped afraid of the feeling that was
developing.  It felt incredible but it scared me.

I stopped playing with myself and picked up the dress and slipped it over
my head and smoothed it down over my butt and hips.  As I was checking out
myself in the mirror again I seen the pair of black 3 inch heels that Mom
always wore with this dress.  I thought what the hell, if I was going to do
this I was going to go all the way.

It took me a few minutes to figure out hot to fasten the strap around my
ankle but finally got it right.  I was very unsteady on my feet as I tried
to stand up.  It took me a few minutes to get my balance.  I learned it was
easier to walk by walking on the balls of my feet and taking small steps.

I walked over to my Moms vanity, found a rubber band, my mom had said I
needed to get my hair cut and it was just long enough to put into a pony
tail.

While I was standing at the vanity I looked over her makeup, I had no idea
how to apply it but I did find a tube of dark red lipstick and applied a
thick coat on my lips.

I was not sure how to explain it but I felt sexy and it felt right.  I was
so nervous walking back to my friends in the living room, I just knew that
they would make fun of me.

Robert did make a few crude remarks but Art gave me a wolf's whistle and
said that I looked even hotter in that dress than my mom did.

I smiled at Art and thanked him.  He motioned for me to come set on the
couch between him and Robert.  Part of me wanted to run back to the bedroom
and take the dress off but part of me liked the attention I was getting
from Art, he was so much nicer to me then Robert was.

As I sat down on the couch my tight dress slide up showing off more of my
legs.  As I went to pull down the hem of my dress Art stopped me ans said
"Leave it like it is, your legs look sexy in hose."

Art then reach over to squeeze my knee.  His touch sent tremors through me.

He started to run his hand up and down my right thigh."Your legs feel even
better than they look."

Art told Robert to see how my hose covered leg felt like, he hesitated at
first but the his hand started carressing my left thigh.

Their hands were driving me crazy and my small cock throbbed ever time
their hand got close to the lacy edges of my panties.

Robert said that things were getting weird and that he thought we should
stop.  Art laughed at him and said he was having to much fun to stop.  I
wasn't sure what Art meant and what he had in mind.

Robert said he needed to go to the bathroom and stood up to leave.  Art
laughed at him and said he did not have to go to the bathroom to jack off.
Robert made a very rude jesture at Art as he left.

While Robert was gone, Art scooted even closer to me.  I was confused by
the feelings I was experiencing but I liked Art's warm body next to mine.

Art asked me if I ever jerked off to porn.  I admitted to Art that I had
never jerked off before.  He surprised me by moving his hand ever further
up my leg to squeeze my cock through the panties and hose.  It was the
first time anyone besides myself had touched my cock and it jerked when he
did.

I had never jerkled off before but I knew enough to know that if Art kept
doing what he was doing that I would cum soon.  I told Art that he had
better stop or I would have an "accident".

He laughed at me and said "That is the idea isn't it?"

I know I was blushing a deep red.  My whole body stiffened as I felt my
orgasm starting to hit.  My cock throbbed and got even harder as Art
squeezed it once again.

To my embarrassment I gave a girlish squeal as I startred to shoot cum into
my Moms black panties.

As I watched Art, he undid his jeans and freed his cock.  I had only seen
other guys cocks in the shower and most were not much bigger than mine but
Art's cock looked huge to me, I latter learned that it was just under 7
inches while mine was hardly over 5 inches.

His cock was semi hard but it was getting harder and bigger as he stroked
it a couple of times.  "Now its my turn."

I thought he meant he was going to jack off on his own but Art reached over
to take my right hand an place it around the base of his cock.

It felt hard and soft at the same time.  As I ran my hand up and down the
shaft of his cock I could feel it throb in my hand.  I wanted to protest
and remove my hand but having a throbbing cock in my hand felt right plus
he had made me cum and something in my brain was telling me it was only
right that I returned the favor.

Art started moaning as I varied the speed with which I was stroking his
cock.  By the way it throbbed I knew he was probably pretty close to
shooting.

Robert returned just in time to see Art's cock erupt in my hand, the first
shot landed on the TV screen and the next several shots landed on the floor
between the TV and us making small puddles.

I ran to the bathroom to get a towel and when I returned there was a
noticeable tension in the room and I had no idea what to say to end the
uneasiness between us all.

That is when we heard the car door out front.  I looked out the window to
see that my brother David had returned.  When I looked back, Art had zipped
his pants and was standing up, they made their escape out the back door
before David could enter.

I am not sure what I was thinking but the main concern for me was wiping up
the puddles of cum on the floor and not changing clothes.

That is why when David and his friend Clay entered the front door they
found me on my knees in the living room wearing Mom's little black dress.

They both just stopped and stared at me.  David asked me what the hell was
going on and what was all over the TV screen.  Clay made a sniffing sound
and asked what that smell was.

I just hung my head becasue I did not want to face either of them.  I knew
I had been caught and was not sure how things were going to turn out.

I could heard the nervousness and the excitement in David's voice.  "Oh Man
wait until I tell Mom that I caught you wearing her clothes, I bet she will
not hesitate to tell your Dad and he will beat the shit out of you."

"Please no, you can't tell anyone."

"Why not? I am sure Clay will back me up."

I was desperate, I was still on my knees and I was pleading for them not to
say anything.

"Well David I think your little brother is cute like that and I think we
should give him a chance to convince us to keep quiet."

I knew I was grasping at straws but I found myselp saying, "Thanks Clay.  I
will do anything just please don't tell."

Clay laughed at my situation, then asked "Anything?"

"Yes please I will do anything...."

David and Clay smiled at each other.  They went and sat at the couch.
David told me to crawl over to them and kneel at their feet.  I felt
humiliated and I did not like the evil smirk on David's face.  I had no
idea what all I was going to be made to do to buy their silence but knew I
would do it because I did not want my parents to know.

I was kneeling in front of the couch looking up at them when David asked me
how often did I wear moms clothes, and where was my friends.

I had to try and explain to them that this was the first time I had tried
on any feminine clothes and how Art had talked me into it as a Halloween
joke.

Clay spoke up, "Well you do make a cute girl, maybe a young flat chested
girl but a pretty one none the less."

I just looked at Clay and felt my face blushing.

David reached out with his foot and nudged me.  "I think you should thank
Clay for the compliment little sissy."

"Um, thank you Clay."

David commanded me to stand up, I did as I was ordered.

I was told to turn around slowly and had to endure comments about my "sexy
butt".

While I was facing away from the guys Clay asked me if I was wearing sexy
panties under my dress and I meekly told them I was.

Clay told me to lift the hem of my dress and show them.  I reached down to
grasp the hem of the short dress I was wearing. I slowly raised it up
little by little until my blacklace panties were showing.

"You know David, your little sister has a sexy ass, I would say it is
better than a lot of girls at school."

I was trying to figure out a way to get out of my perdicument so I could go
change and put tonight and all the craziness behind me.

David asked me if I had fooled around with Art and Robert and I tried to
tell them no but some how they knew I was lying.

David reached out and smacked my ass hard.  "You are trying to lie to us.
Now tell us what happened tonight.  What did you do for them?"

Tears started rolling down my cheeks as I confessed about the hand job I
gave Art.  David asked me how often did I fool around with my friends and I
told them that it was the first time I had ever done anything like that.

David and Clay shared a knowing look as Clay said he bet it would not be
the last time I would do something like that.

Clay looked at the clock and said he hated to leave before he seen how all
of this turned out but he needed to get home before curfew so he would not
get grounded.  He slapped me on the butt before he left me alone with my
brother.

I told David I was going to change back into my own clothes.  He follwed me
as I went into our moms bedroom where I had left my male clothes when I had
put on the dress.

David sat on Moms bed and said he wanted to watch me strip.

I slipped the dress over my shoulders and started to slide it down, I was
very self concious knowing that David was watching me

I stll had on panties, black pantyhose and the heels.  I walked to the bed
to sit down and remove the high heels and as I sat down David stood up and
told me to watch him undress.

I watched him remove the red T-shirt then he kicked off his tennis shoes,
next he slide his jeans down and off leaving him standing in front of me in
just boxer shorts.

I had seen David naked many times but had never paid any attention to his
cock.  My stomach fluttered as David hooked his fungers into his boxers and
slide them down and off.

His cock was already hard and it was even longer than Art's.  Maybe not
quite as thick but definitely longer.

I stood up so I could remove the pantyhose and panties but David come up
behind me and stopped me.

He reached around and hugged me from behind.  I could feel his hard cock
pressing against my pantyhose clad ass.  David cupped my small nonexistent
breasts and started to pinch my nipples as he ground his cock against my
butt.

I was hard again.  David kissed the back of my neck as he ground harder
against me.

"Baby girl, you make such a hot little slut.  You are going to make me
shoot my load.

I did not know what possessed me to do it but I started pushing back
against David's cock.

David reched down and slide my pantyhose and panties down to my knees, I
felt his cock start to slide up and down between my butt cheeks.  He had
not entered me but was using my butt cheeks to jack off with.  I caught
myself wondering what it would be like to be fucked in the ass like a girl
and was not paying close attention until David moaned and said He was going
to cum.

He let out a loud moan and I felt Davids hot cum hit my exposed butt.
David held me tight until he stopped cumming.  By then cum was running down
my thighs soaking into the pantyhose.

Finally David let go off me and pushed me away mumbling about needing a
shower.

After he left Mom's bedroom I finished undressing, the Panties and
pantyhose I had been wearing were soaked in cum and I knew I could not just
return them to the drawer that I had gotten them from.

After I had replaced the heels and the dress to Mom's closet, I wadded up
the panties and pantyhose and took them back to my room and hid them under
my mattress.

The trailer we lived in had three bedrooms so I had a room to myself.  I
shared a bathroom with David but mostly had privacy.

I laid in bed listening to the shower running, thinking about what all had
happened to me tonight and caught myself imagining what David's naked body
looked like with the water running over it.  I did not want to admit it but
I had enjoyed every thing I was made to do and was hard again.

I remembered how great it felt when Art had played with my cock and I
started to rub and stroke it.  Something just did not feel right and was
not sure what it was until I remembered the feel of the satin material of
the panties rubbing against my cock.

I reached under the mattress and got the panties I had hid there earlier.
I thought about just wrapping them around my cock but I wanted to feel them
around my waist again.

I slipped them up my legs again and smoothed the material into place.  I
started mimicking what Art had done and while I wanted the pleasure to
last, I came quickly.

I dozed off still wearing the panties and nothing else.

To be continued........