Date: Tue, 12 Nov 2013 20:17:46 -0500
From: Andi <SissyAndi@Safe-mail.net>
Subject: Trailer Park CD 03 (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 cross dresser.
All Stories are the property of the Author.

Any feedback would be greatly appreciated. Thanks.  You cam Email me at
SissyAndi@safe-Mail.net .

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Trailor Park CD RD03

I had dressed up for my friend Art and had given him a hand job a couple of
times.  That all started one weekend when Art, my other friend Robert. and
myself was at my house and they were discussion what costumes they were
going to wear for the upcoming Halloween party that the neighborhood has
every year.

I had mentioned that I was probably not going to the party because I did
not have a costume and we did not have the money to buy or rent one.  That
is when Art and Robert had suggested that I wear some of my mothers clothes
and go dressed as a female.

I had not given the Halloween party any more thought and it was fast
approaching.

Art stopped me in the hall at school one day and asked me about it, I told
him again I was not going to the party, that I did not want to go out
dressed as a girl.  Art gave me one of those smiles that I find very
sexy. I had never told him but I would probably do most anything for Art
when he smiled at me that way.

"Ah come on, Sadie is a very pretty girl and I bet she would be a big hit
at the party, and I think I have the perfect costume for Sadie.

Sadie is the chosen name I use when I am dressed as a female.  I felt my
face start to blush, that seemed to happen a lot when I spent time with
Art.

I had no idea what he had in mind, I figured he just wanted to get me alone
and get me to give him another hand job which I would probably do with
enthusiasm.

Anyway Art asked me again to go home with him, he said we could use the
pool.  While I lived in a trailor park with my mom and brother Art and his
family lived in a nice neighborhood with a big fenced in back yard that had
a pool, to me Art's family was rich.

One good thing about living in the deep south was that it was warm enough
at the end of October that you could still swim.  I know Art had said that
his Moms pool guy was coming over next week to shut down the pool and cover
it for the winter.

I loved going swimming over at Art's house during the summer because he has
a really hot older sister named Kellie.  I knew she would not be there
today since she was away at college and I would not see her sexy body in a
skimpy bikini.

After the last class I met Art in front of the school.  his mom was going
to give us a ride home then go shopping.  So I would be alone with Art, I
was already anticipating playing with Art's hard cock.  I did not have any
feminine clothes with me but Art had a cute Mother and a very hot sister
and I was sure I could find some panties to wear while we played.

My small cock was already rock hard as his Mom dropped us off at the end of
the driveway and we walked to the house.  We entered the house and went to
Art's bedroom.

I asked what idea did he have for my Halloween costume.  He told me to wait
in his room while he went and got it.  A few minutes later Art returned and
dump some clothes onto his bed.  It was a cheerleader's outfit.  It
belonged to his Sister Kellie, she had been a cheerleader back in High
School.  Not just a cheerleader but the head cheerleader her senior year.
I remembered how hot she had looked wearing that outfit.

I told Art that there was no way I could go out dressed in his sisters
cheer uniform.  He told me that it would look good on me and that he wanted
to see me wearing it even if I did not want to wear it as my Halloween
costume.  He looked at the clock and said I could think about it but he
wanted to go for a swim before it got to late or cold.

I asked him if I could borrow a pair of swim trunks and he thought about it
for a few seconds.  "I have a better idea."

With that he left the room again and this time when he returned he had one
of Kellie's Bikini.  It was black outlined in pink with a pink bow between
the cups of the top half of the bikini and another little pink bow on the
front of the bikini bottoms..

I gulped and started to say no but Art stopped me.  "Look there are no one
else here and we have a big privacy fence so no one can see into their back
yard, I am the only one that will be admiring Sadie in that bikini.

I knew I would probably be safe and the idea of wearing that hot bikini for
Art really turned me on so I agreed.  As I headed for the bathroom to
change I told Art to go ahead and I would be out soon.

It did not take me long to change and the bikini fit me OK even if I was
flat chested on top.  Before I left the bathroom I grabbed one of the
oversized towels and wrapped it around my body.

When I joined Art by the pool he stopped swimming and was watching me
close.  I undid the towel and as it dropped to the ground I tried to strike
a pose like a swimsuit model.  Art did not say anything but from the look
he was giving me he must have liked what he saw.

I went to the diving board, dove into the pool and swam over to where Art
was standing.  As I broke the service Art was already reaching out and
cupping my butt through the bikini bottoms.

"Wow Sadie you look even better than Kellie does when she wears that
bikini."  It sounded kind of odd that he would talk about his sister that
way but I knew that he had a crush on her and that it was meant as a
compliment.

I let him take me into his arms and hug me close.  His cock was already
hard and poking me in the belly.  I giggled and reached down to squeeze it.
We fondled each other in the pool until I broke away and swam to the other
end of the pool.

Art started doing some laps in the pool showing off his swimming ability
while I just played in the shallow end and watched him.  I could not keep
from admiring his body as he finally got out of the pool.

Art was 5'10" with short blonde hair and blue eyes.  He was a little chubby
but not fat and man the way his cock was straining the front of his swim
trunks made his cock look bigger than the 7 inches I knew it to be.  As Art
laid down on a lounge chair by the pool to dry off and enjoy the warmth of
the sun I swam a few laps of my own.

As I exited the pool I felt Art's eyes on me and I tried to look sexy as I
stood there and let the water run from my bikini clad body.  I am not sure
how I looked to Art but I felt incredibly sexy at that moment.  I walked
over to Art and knelt by the side of his chair, he was stretched out and
relaxing but he was also watching every move I made.

I knew what he wanted, what we both wanted, and I reach over and started to
work his swim trunks down his legs.  He had to lift his butt to allow me to
remove them and when I did his rock hard cock came into view.

I reached over and started stroking his cock.  It felt even harder than it
had in the past when I had given him hand jobs.  I was leaning over him
looking down at his cock and working my hand up and down the shaft.

I had an idea so I asked, "Art are you Sadie's boy friend?"

He smiled at me and replied, "well I guess I am and to be honest with you I
never thought I would have such an incredibly sexy girlfriend."

Oh how sweet.  The compliment made my small cock throb in my bikini.

Art let out a sigh then said, "Why do you ask Sweetheart?"

I replied, "I just wanted to make sure you were my boyfriend before I did
this."

I leaned down and took the head of his cock into my warm wet mouth.

"Oh Sadie, that feels so freaking good."

With that encouragement from Art, I started working my mouth up and down
the shaft of his cock and each time I went down I took more and more of it
into my mouth until I felt his pubic hair tickle my nose.  I was surprised
that I was able to take the entire length into my mouth.  Surprised and
proud.

I continued to work my mouth up and down for a few minutes the I removed
his cock from my mouth.  I started to lick and suck on his balls then I
licked his entire cock from the balls to the head.

Art was moaning and breathing heavier now and I knew he was getting close.
I was excited by the prospects of Art shooting his load of cum into my
mouth.  And being the good slut that I am I wanted to swallowing it all.

I was on my knees and as I sucked the head of Art's cock I was cupping his
balls with one hand and stroking my small cock with the other.  I was
getting close also and it was just a question who would cum first.

Art beat me to it.  He had his hand on the back of my head and when he
started to cum he pushed my mouth down onto his cock as far as he could.
When He flooded my mouth with his cum, even if I had not been so
enthusiastic to swallow I had no choice.  It was swallow or choke.

I was savoring the taste of a fresh load of cum as I felt my orgasm hit.
My cock throbbed and I started shooting my load onto the deck beside Art's
chair.

After we both finished cumming and had started settling down I could not
resist leaning down again and kissing the tip of Art's deflating cock.

Art had a very big smile on his face as he stretched out and started dozing
off.  I laid in a chair beside of him and had almost drifted off myself
then it hit me that I should be careful and not get a sunburn, developing
feminine tan lines would be hard to explain.

I let Art sleep as I went inside to change clothes.  I took off the bikini
and hung it up in Kellies bathroom, I had to remind Art to put it back in
the drawer after it dried or someone might get suspicious.

As I dressed I kept glancing at Kellie's cheerleading uniform laying on
Art's bed.  I thought what the heck, I would take it home with me and maybe
try it on later so I stuffed it into my back pack and headed out.

********

It was late and I knew Mom would be at work and I figured that David would
be out with his friends.  I was disappointed to see David's car in are
short driveway and realized that I would not have the house to myself.

I was hoping that I could slip in unnoticed and head to my room.  Of course
things did not go as planned.

David stopped me as I came through the door.  "Where the hell have you
been?"

I could smell alcohol on his breath.

"I was over at Art's house."

"Oh you were with your boyfriend.  Did you dress like a slut for him?  Did
you give him another hand job?"

"Uh no we just went swimming."  I hoped I was not acting funny and he would
not notice that I was lying to him.

David just smirked.  As I tried to get by him and go to my bedroom He
grabbed my back pack.  "Lets see which outfit of Mom's you took over to
Art's."

I tried to get it back but David is taller than me, bigger than me and
stronger than me.  He pushed me away and I fell onto the couch.  I was
horrified as I watched David open my back pack.  He started laughing hard
as he found Kellie's cheerleading uniform and pulled it out.

"Where the hell did you get this?"

I could not look David in the eyes as I mumbled that it belonged to Art's
sister.

"Did you model that for your boyfriend?"  I know he was just harassing me
but for him to be doing this not long after I had asked Art if he was my
boyfriend was a little un nerving.

"No I have not worn it yet, I told Art I did not have a costume for the
Halloween party and Art suggested I go as a cheerleader."

David gave me a strange look.

"I know you will never be as hot as Kellie was when she wore that but why
don't you go put it on and lets see how you look wearing it.

I refused but then David slapped me across the face and reminded me that he
had been nice to me so far and had not told our Mom that he had caught me
in her dress but that could all change if I did not do what he asked me to
do.

"Remember I have Clay to back me up so it would not just be my word against
yours.  Plus I have some football player friends who would like nothing
better than to pound on a sissy like you.  You know how you LOVE pain."

"No please, I will put it on.  Just do not tell anyone Please!!"

He handed me my back pack and the cheerleading uniform and ordered me to go
get dressed.  It was just after 7 and Mom was at work and would not be home
any time soon.

I went to my bedroom and thought about just locking the door and hope for
the best but I was soon undressing.  I slid the shiny brown tights then the
cheerleading panties up my leg and tucked my small but growing cock back so
it was all but un noticeable.  I quickly put on the top and the skirt.

I was scared but knew I did not have a choice.  Before I left my bedroom I
brushed out my blonde hair and painted my lips with the tube of pink
lipstick that I had also taken from Kellie's bedroom earlier.

As I entered the living room, David said, "MMMM you know Scott you look
like a cute and innocent little freshman cheerleader."

His comment made me blush.

He motioned for me to come closer.  I hesitated then did as he said.

When I got within arms length he reached out and grabbed my arm pulling me
to him and down across his lap.  I struggled to get free but he was to
strong for me.

As I struggled to get free I was squirming on David's lap.  He was
fidgeting and I thought he might (Actually I was hoping he would) cum from
the friction we were creating.

I was face down across my brothers lap and I felt him raise my skirt.  I
was shocked when the he slapped my panty clad butt the first time and let
out a scream.

David told me to be quiet or he would put something in my mouth to shut me
up.  I was afraid what that might be.  Afraid and excited at the same time.
My small sissy cock was rack hard also and each time David swatted my butt
I would thrust forward.  The sensation was growing and I feared I would cum
on my brothers lap..

David would land a hard slap to my butt then he would grope me.  As I
squirmed it caused my cheer panties to creep up between the cheeks of my
ass giving me a wedgie.

David slide a finger under my the waist band of my panties and tights
pushing a finger into me.  Causing me to squirm even more and I each time
he pushed his finger into my ass I would lurch forward and to anyone
watching they would think I was dry humping David's crotch.

As he continued to spank my ass and work a finger in and out of my butt
David asked me, "So did you give Art another hand job today while you were
over there?"

I shook my head and answered "No."

"Oh?  Then what did you two do?"

"We just went swimming."  There was no way I was going to tell my brother
about the blow job by the pool while I was wearing Kellie's bikini.

As he continued to molest my ass he mumbled that he would love to get a
hand job right now, that it had been awhile since Amy, his girlfriend, had
made him cum and he needed to cum so bad.

The more he talked the harder he was spanking me.  I was trying to get away
and I was begging him to stop.

"what will you do for me if I stop?"

The spanking was getting really painful and I was ready to do almost
anything to get him to stop, even if that meant giving my brother a hand
job or something even more naughty.

"Please David I will make you cum just stop hitting me."

He let out a laugh and pushed me off of his lap.  He told me to stand up
and to take my top off.  I quickly unbuttoned my blouse and slide it off of
my shoulders and folded it up then laid it on the coffee table.

I was not wearing a bra and for some reason it made me feel self conscious.
I was standing there with my right arm across my chest as David gave me my
next "order'.

"Now take off that sexy skirt."

I turned my back to David.  I unzipped the skirt.  I thought I would give
my brother a little show so I wiggled my ass as I worked the skirt over my
hips and down my legs.

I folded the skirt and placed it with the top on the coffee table.  When I
turned around, David had undone his jeans and had his cock out.  As he
stroked it, it had grown to its full length. and was throbbing and leaking
pre cum.

I felt the overwhelming urge to drop to my knees right then and there and
suck it like the cross dressing slut I was quickly becoming.  Yet I
resisted the urge.

"Now the panties!!"

I removed the panties and placed then on the stack of clothes on the coffee
table, leaving me in just the shiny brown tights.

David patted the couch beside of him and told me to take a seat.

David reached out and took my hand and placed it onto his cock.  I knew
what was expected of me so I squeezed the head then started working my hand
up and down the shaft.  His cock was longer than Art's though Art's cock
was thicker.

If I was to be honest I could not help but wonder what it tasted like but I
was not about to make it look like I was eager to do anything.  If he
decided to "force Me" to suck him I would put up token resistance then do
what I was told.

As I was stroking his hard throbbing cock, David started to run his hands
over my body.  He began by running his hand up and down my thigh feeling my
hose encased legs, then he ran his hands over my tummy and sought out my
non existent breasts and found my very hard nipples.

I let a moan slip past my lips as David found my left nipple and started
rubbing it.  When he pinched it I almost shot my load.  I let go of his
cock as He pulled my hair and lifted my face to look at him.

He handed me the panties and said. "Here use these."

I took the panties and wrapped them around David's cock and resumed the
hand job I was giving him.  I was looking into his eyes when they took on
this glassy look, That and the fact that he was starting to breath very
hard, I knew he was about to cum.

As David shot the first stream of cum he twisted my nipple hard causing me
to scream out and cum at the same time.  We both shot our load and created
a mingled mess on his thighs.

I tried hard not to get cum on Kellie's panties but some did get on them.

We were both breathing hard and covered with sweat as we finished coming.
We were looking into each others eyes and that is when David surprised me
by pulling me to him and kissing me softly.


"You need to go get a wash cloth and clean this up."

I took the panties with me to the bathroom.  I had planned on washing them
out so they would not get stained or ruined.

I turned on the water but instead of washing them I caught myself bringing
them to my nose and inhaling.  Before I realized what I was doing I stuck
out my tongue and tasted the mixture of mine and David's cum.  It tasted
saltier than Art's cum but it was not bad tasting.  I wondered what David's
cum tasted like on its own.

I went back to the living room with a wash cloth.  After I cleaned the cum
from his thigh David pulled me into an embrace and kissed me again.

This was not an innocent kiss, it was full of erotic passion as he kissed
me like I presumed he kissed his girlfriend.  As he continued to kiss me I
started kissing him back.  It was my first true kiss and though I did not
have any thing to compare it to I decided that David was a very good
kisser.

He had resumed playing with my nipples and when I let out a moan, David
took the opportunity to push his tongue passed my lips.

As his tongue explored my mouth I reach down and started stroking his cock
again.

I was disappointed when he broke the kiss but when I felt his lips on my
right nipple I was overcome from the feelings it was causing in me. His
cock was already starting to show signs of life and was getting hard again.
We both were getting hard..

David said he had a kinky idea.  The way he said that suggested that what
we had done so far was just your average inter-action between brothers.

He pushed me away and told me to get onto my hands and knees.

I started shaking my head no as I said, "Please David you cant do that to
me, please lets stop."

He smiled at me and said "Don't worry baby girl, I am not going to take
your virginity tonight. Just do what I say."

Looking into his eyes I felt certain that David was being honest with me
and had no intention of hurting me so I got onto my hands and knees on the
couch.

David got behind me.  I shivered as he ran his cock up and down between my
butt cheeks.

He told me to press my thighs tightly together.  As I did I felt David push
his cock between my thighs.  He started pushing forward then back.  He
worked himself into a rhythm and was using my thighs to masturbate.

As he was "fucking" my thighs he slapped my butt and told me to start
jacking off.  I started matching David's rhythm and imagined that maybe it
would not be so bad if David actually wanted to fuck my sissy ass.

I would make him work for it at first but I would probably give in quickly.

We were both starting to breathe heavily as we both neared our second
orgasm.  The idea of being fucked like a girl sent me ahead of David and I
came first.  I grabbed the wash cloth and cleaned my self up as best as I
could.

When David started to cum again he pulled back and shot his load onto my
butt and bare back.  I felt so dirty having my brother deposit his load of
cum onto my body.

I felt David's fingers on my ass and wondered what he was up to now.  When
I looked back to see what he was doing he reach up and ran his cum coated
fingers across my lips.  He scooped up more of his cum and forced his
fingers into my mouth and made me suck the cum off of them.

He repeated his actions until there was no cum left and I was allowed to go
to my room.

On the way to my room I stopped by my moms room and opened her lingerie and
panty drawer.  I got a pair of sheer pink panties and took them with me to
my room.

I put on the panties and crawled into bed.  I fell to sleep with the taste
of David's cum still on my lips.

To be continued......