Date: Fri, 27 Dec 2013 11:14:46 -0500
From: Andi <SissyAndi@Safe-mail.net>
Subject: Trailer Park CD 05 (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 can Email me at
SissyAndi@safe-Mail.net .

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Background Information

I am Scott, at 13 I lived 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 were a lot of kids in the trailer park ranging from 6 to 17.  Some
were very pretty girls.  My half brother David was 17.  Mom had him from a
previous marriage and then married my Dad, My dad left Mom when I was 6.

Mom was a single woman but worked hard trying to support two growing boys.
She had 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 found 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.

********

Trailer Park CD 05

It was now a couple of weeks after Halloween and looking back I could not
help but to think about that day and remember what a sissy slut I had
turned into.  I had sex in one form or another with four different guys,
one of them being my older half brother David.

Since that day things had settled down somewhat.  In the last three weeks I
have given David an occasional quickie blow job when he had demanded it,
one while our mom and her new boyfriend was setting in the living room.

Besides the oral sex with my half brother, I thought of as my friend Art as
my"boyfriend" and I continued to service him orally and sometimes he would
fuck my sissy butt.

I was sitting on the couch in the living room re living the antics of
Halloween and my small sissy cock was hard as a rock.  Under my male
clothes I was wearing a pair of teal green satin panties that had lace
around the leg openings.

I was considering going to my room and jacking off.  The phone ringing
jolted me from my memories so I answered it.  It was Clay, a very cute guy
who was my brother's best friend.

I told him that David was not at home and he said that it was ok because he
had called wanting to talk to Sadie.  Sadie was the feminine name I had
chosen to go by when I cross dressed.

Without thinking about it I started using my most feminine (and what I
hoped) was my sexiest voice.

Clay was one of the four guys who I had fooled around with that faithful
night but I had not seen him around much since Halloween and I had begun to
wonder if he had regrets and he was avoiding me.

Clay asked me how I had been and tried to make small talk but I had a
feeling there was more to this call.  Clay eventually got around to the
main reason he had called.

"Sadie, I really enjoyed what we did Halloween night and I was ....well I
wanted to ask you, would you like to go on a date with me?"

I was shocked, no guy had ever asked me out before.  Even though I
considered my friend Art as my boyfriend, he insisted that every thing we
did, we did in private.

I was please and a little excited when I told Clay that "I would love to go
out with you.  But I have to ask just what do you have in mind."

He explained that his parents were going to be out of town this weekend and
that maybe we could go out to eat then get a movie to bring back to his
house and watch it.

It was not exactly what I had wanted for my first date but it was better
than anything I had been offered up to this point.  Like I said earlier,
Clay was a very cute boy and I know from experience that he had a nice
cock, at least 7 inches long and not to thin.  My mind was filled with the
things we might do when he had me all alone at his house.

Clay said it would be best if we could go out on Friday night.  David was
on the basketball team and they had a game on Friday so he would be busy.
My mom would not be a problem since she left early every afternoon to go to
work at the strip club.

He told me that I should be dressed sexy and ready for him by 6:30 and he
would be by to pick me up.  I was already having butterflies in my stomach
in anticipation.  My first date with an older boy.  Every girls dream.

After we had ended the call I went to my room and stripped down to my
panties and laid on the bed.  I was having visions of cuddling up on the
couch next to Clay as I furiously stroked my cock with one hand while I
reached up to pinch and twist my nipples with the other.

I was caught up in my little fantasy and extremely excited when I heard the
front door to our trailer slam shut.  I figured it was David and at the
moment I was so horny that I did not even care that it was my half
brother. I was craving a nice hard cock and I figured any cock would do.  I
considered running out to meet David wearing just panties and see if he
wanted to fool around.

I grabbed a short silk robe I had borrowed from my Mom's closet and wrapped
it around my feminine body, applied some dark red lipstick and lightly
sprayed my body with cheap girly smelling perfume I had managed to buy on
sale at the local drug store.

I was shaking thinking of what was going to happen between me and my half
brother as I paused at the bedroom door.  I took several deep breathes
trying to calm my nerves.  Finally I built up the courage and went to find
and seduce my brother.

Imagine my shock and humiliation when I ran head long into my Mom's new
boyfriend coming out of my Mom's bedroom carry a pill bottle that contained
medicine that my Mom took for migraines..

He gave me a grin as he said "Well, well what do we have here?"

I could not say anything and felt like I was going to start crying when he
put his hand on my shoulder and started directing me to my mom's bedroom.

"I knew there was something "special" about you Scotty, tell me does your
Mom know you are a pretty little sissy boy?"

I refused to meet his stare and all I could do was shake my head no.

When we were in my Moms bedroom He reached out and untied the sash holding
my robe together.  Sliding it over my shoulders he let it fall to the floor
leaving me standing there in nothing but panties.  He laughed as he spun me
around to get a good look at my panty clad butt.

He sat me on the edge of the bed.  I was looking down at the floor dreading
what Mr. Stevens might make me do.  I knew he was to strong for me to fight
off.

He slapped me hard across the face.  "Little slut, look at Daddy as I
undress.  See what a real man's body looks like."

I looked up and watched Mr. Stevens undress.  He was not that bad looking
for a man in his 40's, but for some reason he gave me the creeps.  He was
6'3" 175 pounds, short blonde hair blue eyes.  His body was lean from
working out every day.  When he was down to his boxers, Mr. Stevens ordered
me to my knees.

"Lets see if you can suck cock as good as your pretty mother.  Take it out
for me."

Knowing I could not deny him what he wanted, I reached into his boxers and
fished out his hard cock.  I slide his boxers down and he stepped out of
them.  As I kneeled before him he thrust out his hips and started smacking
me in the face with his hard cock.  It was the first adult cock I had seen
up close and it had to be 8 1/2 inches long.

He took his cock into his hand and started rubbing the tip across my
painted lips.  I opened my lips and took the head into my warm mouth.

He was moaning as I worked my mouth up and down the shaft of his cock.

"Good Lord, you are a sexy sissy bitch and you can suck cock almost as good
as your mom.  We know she has had a lot more practice.  One of these days I
am going to have you both kneel before me and share my cock."

I cringed at his crude remark.  I wanted to get this over with as quick as
possible but Mr. Stevens had other ideas.  When I felt the head get even
larger and start to throb he pulled out and sat on the bed.  He ordered me
to crawl to him and I obeyed.

While I was kneeling there in front of him, Mr. Stevens reached out and ran
his hand through my blonde hair.

"Tell me sweetie, are you a virgin?"

I acted like I did not hear his question.  He ran his hand down my cheek,
"its ok sweetie, you can tell Daddy if you have been a bad girl."

I still did not answer.

SLAP!!!!!

"Now tell Daddy that you have been a very bad girl."

I blurted out, "No Daddy I am not a virgin.  I have been a very bad girl"

He pulled me to my feet and across his lap.  I could feel his very hard
cock press against my tummy.  He started running his had over my butt and
then he raised his had and brought it down hard against my ass.

"You have been bad and Daddy needs to punish you.

He landed blow after blow on my butt and when he stopped he eased my
panties down exposing my hard sissy cock and my red stinging butt.

"Tell me you understand why Daddy had to punish his pretty little girl."

Not wanting to make him mad I said, "Yes Daddy I understand I have been bad
and you need to punish me."

He slapped my bare ass one more time before pushing me off of his lap and
onto the floor.

"Tell Daddy that you want to suck his cock.  Beg me to let you suck it"

"Please Daddy may I suck your hard manly cock?"  "I want to please you so
bad please let me suck it until you cum for me."

He smiled down at me and told me "good girl" and motioned to his cock.

I leaned in and started to suck it.  Again when it was throbbing and he was
on the edge of cumming he pulled out and let his cock settle down.

"You know your Mom does not like to have anal sex.  On the other hand I bet
you love it."

I refused to look at him when he was talking dirty to me.  He got off of
the bed and pulled me to my feet.  he told me to lie down on the bed.  I
thought he meant face down to give him access to my butt.

He slapped my butt again and told me to turn over.  I rolled over and was
looking up at him as he positioned himself between my legs.  He pushed my
legs back over my head and told me to reach down and spread my ass cheeks
for him.

I was holding my ass cheeks apart exposing my tiny opening, when he pressed
the head of his cock against it.  I knew that it was going to hurt very
badly.  He gave a violent thrust forward and forced the entire length of
his cock into me.  I let out a very load scream and he slapped me hard
telling me to shut up.

He started fucking me hard and deep as he looked into my eyes.


"MMMMM Your sissy pussy is so tight and snug...That's it, milk my cock with
your ass."

My butt was burning and the pain was incredible.  I was on the verge of
passing out from the pain.  He ordered me to stroke my cock as he fucked
me.

"Daddy is going to cum in his sweet little girls ass.  Tell me you want
that sweetie."

I knew I had to play along, "Please Daddy fuck my tight ass, cum in me
PLEASE!!!!"

His thrusts became faster and more violent and that caused me to cum hard.
He finally thrust his cock as far into me as he could and held it there
filling my ass with his cum.

He laid there on top of me as he recovered.  His cock shrunk and came out
of my ass.  He rolled over and ordered me to clean his nasty cock.  I
leaned down to lick the cock head and the shaft clean.

He got up and started dressing.

"Now you know this has to stay between us, your mom can never know what we
did."

I agreed that no one should know what happened.

Before he left he leaned down and kissed me on top of the head while
reached out and twisted my right nipple.

 "I am already looking forward to the next time."

I was hoping that this was going to be a one time thing but I knew better.

My mind wandered back to the call from Clay, I decided to spend my time
looking forward to my upcoming date and not dwell on having sex with my
Mom's boyfriend.