Date: Tue, 11 Aug 2015 13:01:35 -0400
From: Andi <SissyAndi@Safe-mail.net>
Subject: Neighborhod Sissy 03 (Transgendered 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.  You cam Email me at
SissyAndi@safe-Mail.net .

Please consider making a donation to the nifty archives so that this great
site can remain free and available to all on the Internet.

Neighborhood Sissy 03

I am Eric and I am 12.  I cant believe how my life has changed over the
last couple of weeks.  My friend Teddy has began referring to me as a cock
slut.

Yes I was kind of forced the first time when I got caught spying on my
neighbors and their friends, But after the first couple of tastes of cum I
was hooked.

A lot of the neighborhood guys as well as other guys from school meet in
the shed behind the neighbors house and the day I got caught looking in the
window I was made to undress and get on my knees, the first day at the shed
I sucked 6 different cocks.

After that I had been back at the shed a couple of times and sucked
anywhere from 4 to 9 cocks in one visit.  Besides my trip to the shed I had
been fooling around with Teddy.

Teddy is 14 and 5'10" tall and weighed around 160 pounds.  short brown hair
and brown eyes.  He was slim and in shape but not very muscular.

He had what I learned was an average size cock at around 6 1/2 inches long
but I thought it was delicious and loved sucking it.  Teddy was the only
guy I had done something with that had returned the favor.

Teddy was also the first guy who fucked me.  I have since been with another
guy named Trent who is 19 and in college.  Trent actually called later and
asked Me for a real date.

I said yes but had no idea how we were going to make it happen.  I had only
worn my sisters panties and lingerie so far.  To go on our date I was going
to dress up completely like a girl and go out in public.  The idea both
excited me and scared the hell out of me.

A couple of days before my date with Trent was suppose to happen, Teddy was
over at my house.  We had just blown each other and we were laying around
in bra and panties enjoying the feeling of wearing our girlie things when I
told Teddy about my upcoming date with Trent and confessed to him that I
had no idea how I was going to sneak out of the house dressed as a girl and
for that matter I was not sure what I was going to wear.

Our date was on a Friday night so Teddy told me to just tell my Mom I was
spending the night at his house and that he and his brother would cover for
me.

So the day of my date I headed over to Teddy's house to get ready.  I was
shaking like a leaf I was so excited and scared.  I had "borrowed" a short
blue dress along with white bra and beige panties from my sister to wear.

After I had dress I looked in the mirror and knew I was not passable and
that my debut and our date was going to be a disaster.

I was so upset I was on the verge of tears.  Teddy was trying to calm me
down and he said that he had an idea but that he would have to bring in
someone else.  I asked who and he said his older sister Kara.

I tried to say no but he calmed me down and said for me not to worry that
she had helped him and she could keep a secret.  I finally agreed to let
Kara help so I text ed Trent and told him to give me another hour, he
reluctantly agreed.

I felt so humiliated when Teddy called his sister into the room since all I
was wearing was the white bra and beige panties.  She was the first girl to
see me wearing panties.

Kara looked me up and down and started laughing, embarrassing me even more.
then she started giving orders.  First she lead us to her room where she
handed me a pink woman's razor and told me to take a quick shower and shave
all of the hair below my neck.

When I returned she inspected my body saying I did a pretty good job.  Then
she handed me the bra and panties and ordered me to put them back on.

I was horrified when I started getting hard.  Yes I was small but it was
still noticeable in the panties I was wearing.  She handed me a pair of tan
pantyhose to put on.  The material felt incredible as I pull the hose up my
legs.  My small cock got even harder.

Next came a thin white blouse, good thing I was wearing a white bra because
any other color and you would be able to make out my bra through the thin
material.  After I had the shirt buttoned up I was given a short gray skirt
with pleats.

Finally I was giving a pair of sandals with two inch heels.  Thank God the
heels were no higher or I would have been stumbling all over the place.

My feet looked ok in the open toe sandals, I just wish we had thought about
painting my toenails before I put the pantyhose on.  Oh well Kara was in
the process of painting my fingernails a light pink.

While my nails were drying Kara sat me down at her makeup table and told me
to watch close because there would come a time when I was going to be doing
my own makeup.

I watched as she did my eyes, added some blush to my cheeks then capped
everything off by applying an almost blood red color to my lips.

When she had finished, she stood me in front of a full length mirror.  I
looked hot.  I looked like a very pretty teen girl except for one problem.
Kara noticed it about the same time I did.

I had a bulge in my skirt that would not go away on its own.  Kara told me
that we needed to take care of that problem.  Before I could say or do
anything she was calling Teddy back into the room.

When Teddy seen me he stopped and stared, "Oh God you are gorgeous!!"

I blushed at the compliment.  Kara told Teddy we had a problem and since I
was his friend he could take care of it for me.  He looked at me unsure of
what she meant but when she lifted the front of my skirt he laughed.

He did not seem embarrassed when he reached over and freed my cock from my
panties.  He started stroking me and it was apparent that he did not care
that his sister was watching.

Kara approached him and whispered something in his ear.  He just shook his
head and fell to his knees in front of me.  Kara stopped him and applied a
coat or red lipstick to his mouth.  It was a deeper shade of red than the
one I was wearing at the time.

She told Teddy that he could proceed and he leaned forward to take my cock
into his mouth.  He bobbed his head up and down on my small cock and I was
so hard that it hurt.

When Kara seen I was close to shooting my load she made him stop.  I was so
eager to cum in Teddy's hot warm mouth that I all but cried when she made
him stop.

Kara had another idea.  She held a glass at the head of my cock and told
Teddy to finish me off with his hand.  It did not take long before I was
shooting jet after jet of cum into the glass.

As soon as I was finished Kara held the glass to my lips and I knew what
she wanted.  I swallowed my own load of cum without being told to do so.

After I was done Kara showed me how to fix my makeup and then handed me a
pocketbook.  She told me a girl had to be prepared so she filled it with
tissues, the tube of lipstick she had used on me, some breath mints, a
twenty dollar bill, she said the money was in case my date dumped me and I
needed a way home. She also put a piece of paper with her cell phone number
and said to call her if I ran into any trouble.  She gave me a wicked grin
and said "I have also included several condoms but i doubt if Trent will
want to use them."

We heard someone drive up and a horn blow.  I checked myself in the mirror,
took a deep breath and went out to meet my date.

Trent actually whistled when he seen how good I looked.

I could not help but tease him a little when I slide into the passenger
seat of his pick up truck, I let my skirt slide up my legs to show off a
little more skin and to give him a glimpse of the sexy panties I was
wearing.

Trent told me that we were going to the college town not far from where we
lived and that we were going to the movies.  On the way Trent pulled off
the road and adjusted his seat back a little.

I was not sure why he had pulled off of the road until he unzipped his
jeans and pulled out his cock.  he put his hand behind my head and pulled
it to his lap.

I did not fight him and took his semi hard cock into my mouth.  I worked my
lips up and down the shaft and I could feel it getting hard in my mouth.

I figured we were going to set there until he came but to my surprise Trent
pulled back on the road and was driving while I sucked his cock.  I prayed
that he would cum soon and that he would not get distracted and have a
wreck while I was giving him a blow job.

I was worried that others could see into the truck and knew what I was
doing but I was too afraid to look up and see for sure.  I did hear an
occasional horn though and figures someone had seen.

I am just grateful that we were stopped at a stoplight when I felt his cock
throb and he started shooting his load of cum into my eager mouth.

When he was done I wiped my mouth with one of the tissues from my
pocketbook and used the mirror to touch up my makeup and reapply my
lipstick.

Trent chose a movie that had not gotten good reviews and the place was all
but deserted.  I wondered why he made such a bad choice when they were
other movies that I really wanted to see.  I would find out why soon after
the movie started.

While we set there in the dark I felt his hand on my hose encased thigh.
he slowly worked his hand up my leg until he was teasing the tip of my cock
through the hose and panties that I was wearing.

Trent leaned over to me and told me to go to the ladies room and take off
my hose, that he wanted to feel the bare skin of my shaved legs.

I wanted Trent to like me and for the date to go well so off to the ladies
room I went.  I was so nervous but I must have looked ok because non of the
women in there gave me a second look and accepted me as one of them.

I went into one of the stalls and shut the door.  I had to take off my
sandals to get the hose off but I accomplished my goal and stuffed the
pantyhose into the pocketbook I was carrying.

When I returned to my seat I noticed that we had the back section all to
ourselves, the few people that were there were setting up front.

As I set down Trent's hand went under my skirt again as he groped me.
Trent felt me up for several minutes, he actually had me on the verge of
cumming when He stopped and I could hear him unzip his jeans again.  I was
not surprised when he pulled my face back to his crotch and I was sucking
his cock a second time so soon on our date.

I had been sucking him for several minutes when he pulled my hair lifting
me off of his cock.  He whispered for me to stand up and when I did he
pulled me in front of him.

I did as I was told and Trent pull my panties down to my knees.  He told me
to reach behind me and to spread my ass cheeks.  I was terrified someone
would see but I did what Trent told me to do.

I felt his hands on my waist and He pulled me down onto his lap.  It was a
tight fit but I felt his hard cock enter me.  I bite my bottom lip to keep
from screaming in pain when the big head of his cock pushed past my anal
ring.

He let me set there for a couple of minutes getting use to feeling his cock
inside of me.  As I sat there Trent reached around and started jacking me
off.

I held out as long as I could but soon I shot a load all over his hand and
the seat in front of us.  He held his hand to my lips and I licked the cum
off of it.

When I was done he placed his hands around my waist again and started
lifting me up and down causing his hard cock to go in and out of me.

I could not believe I was letting Trent fuck me in a movie theater where
anyone could possibly walk by and see us.  Suddenly the idea of being
watched just added to the excitement.

He pumped in and out of me for several minutes and soon he was shooting a
second load of cum into me.  I used my ass muscles to milk every last drop
from his cock and he finally lifted me off of him and placed me in the seat
beside of him.

By now we both had lost track of what was happening in the movie so we
agreed to leave early.

I could feel the cum running out of my ass and down my thigh so I stopped
by the ladies room on the way out to clean up a bit.

After we left the movie we went to a drive in and got milkshakes.  Mine was
vanilla and except for being cold it reminded me of the delicious cum I had
swallowed earlier.

On the way home Trent pulled into a deserted and somewhat abandoned
shopping mall parking lot.  he pulled around back so no one could see us
from the road.

We got out and he helped me up into the bed of his truck.  Before I knew it
He was leaning against the cab and I was on my knees with his cock in my
mouth yet again.  I could still taste the remnants of his cum and the funky
taste of my ass on his cock.

I had already cum twice but I was hard and horny again so while I sucked
Trent I had my hand between my legs working it up and down the shaft of my
cock.

Before I could get off again Trent made me stop sucking him, he turned me
around and got into position behind me.  This time there was no pain as he
entered me.

He had cum twice before so this time he fucked me long and hard.  I
continued to stroke my small cock and after a while I came hard while being
fucked.  That sent Trent over the edge again and I felt his warm cum
filling my ass again.  There was not as much cum as the other times.

After he pulled out I was made to clean his cock one last time before he
drove me home.  Kara met me at the door and lead me to Teddy's room making
sure no one seen me in the process.  I had to tell Teddy and Kara all of
the details of my date.

After Kara left Teddy pulled his cock from his shorts and told me he was
hard from hearing everything I had did on my date and besides I owed him
for earlier when he had sucked my cock.

I took his cock into my mouth and worked my magic.  I had been fucked twice
and this was the second load of cum I had swallowed.  I was exhausted.

Teddy kissed me on the forehead and I fell asleep in his arms.  I was still
wearing the bra and panties that I had worn on my date.

********

To be Continued