Date: Mon, 27 Jul 2015 12:05:47 -0400
From: Andi <SissyAndi@Safe-mail.net>
Subject: Neighborhood Sissy 02 (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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Neighborhood Sissy 002

My name is Eric and I can't believe what has happened to me over the last
couple of weeks.

I had been caught spying on the neighborhood guys and had been forced to
suck several cocks including my two neighbors Ted and his older brother
Rick.

Ted had even visited me one day and convinced me to let him fuck me in the
ass.

When Ted had visited me that day he had planted the idea of me wearing my
sisters clothes and dressing like a girl while we fooled around.  Since
that day I had been wearing her panties and had wanted to try more but had
been afraid to go through my sisters stuff.

Since I had gotten caught spying on the guys that day I had been back to
the shed a number of times and one hot afternoon I had sucked off 8
different guys, swallowing most of their loads.

I was home alone one Saturday morning when Ted called me asking what I was
up to.  When I told him nothing and that I was alone he said he was coming
over.  He said maybe we could have some fun like the last time which I knew
meant that he would want to fuck me again.

I guess you could say I had a small crush on Teddy, he was 5'10" tall and
weighed around 160 pounds.  short brown hair and brown eyes.  He was slim
and in shape but not very muscular.

At the time I was only 5'4" and 135 pounds, short blonde hair and blue
eyes.  Luckily I could wear most of my sisters clothes.

Yes it hurt the first time we had sex but the pain turned to pleasure
before he came in my ass.  I had been fantasizing about getting fucked when
I jacked off late at night and I definitely wanted to try it again but I
was embarrassed and I would not be the one to bring it up.

I decided I would take a quick shower before Ted came over.  When I emerged
from the shower I started to put my shorts and a T-shirt back on then I got
a naughty idea.

I quickly went to Stacy's room.  I wanted to wear panties for Ted and
decided that I should wear clean ones and not the ones I had been stealing
from the dirty clothes.

It was the first time I went to Stacy's room and went through her stuff.  I
was always tempted but was to chicken to do it but "having a date" with Ted
gave me the courage to go through her underwear drawer.

What I found surprised me.  I knew my sister was hot and figured that she
was having sex with her boyfriend but I never knew she had such sexy
lingerie.

I found a red lacy bra,panty and garter belt set, I was already hard when I
got back to my room to put them on. I thought to myself that I wanted Ted
to be happy with the little surprise I had in store for him.

I quickly called Ted and told him to give me 20 minutes then come over and
to not even knock, I was alone in the house and I would leave the back door
unlocked and for him to just come up to my room, I would be waiting on him.

I had been watching porn and "how to cross dress" videos on the Internet so
I knew how to hook the bra in front and slide it around.  I also knew how
to put the garter belt on and attach the stockings to the garters and to do
that before I put the panties on last.

After I had every thing on including the smokey black stockings I could not
help but squeeze the head of my cock as I fixed the panties into place and
adjust them for the small but growing erection that I had.

I had only worn panties before so when I put the bra on I was disappointed
that the cups were not filled out.  So I used a pair of old socks to pad my
bra.

I caught a glimpse of myself in the mirror and thought that while I was not
knock out gorgeous that I looked sexy.  I just wished that my hair was
longer.

After I was dressed I laid down on my bed and tried different positions
trying to decide how I wanted to pose for Teddy.  I could not believe I was
doing what I was doing, I was dressed like a slut and waiting for the
neighbor to come over and fuck me.

I was so ready to cum but wanted to wait until Teddy arrived.  I tried to
be a good girl but I caught myself running my hands up and down my hose
encased legs and squeezing the head of my cock.

I jerked my hand away and my heart skipped a beat when I heard a knock at
my bedroom door.  I relaxed a little when I heard Teddy's voice asking if
it was ok to come in.

I positioned myself in what I hoped was my sexiest pose and told Ted come
in.  I thought I was going to surprise Ted but I was the one that was
surprised because Ted was not alone.

He was with a guy that I did not know.  They laughed at me when I reached
for the sheet to cover myself up.

Ted introduced the other guy as Trent, and went on to explain that he had
been one of the originals who started the fun in the shed next door but now
that he was a sophomore in college he had not been over in a while.

Trent was in town and wanted to have some fun before he had to go back to
college and was disappointed when he dropped by and no one was in the shed
playing.

Ted had told Trent that I might be willing to provide a service for them
but he was even shocked to see how eager I was for cock.

I looked Trent up and down, he was cute.  Just over 6 feet tall and 180
pounds.  a slightly muscled upper body and a noticeable bulge growing in
his jeans.

Trent reached out and pulled the sheet off of me and then complimented me
on my outfit.  And before I could protest they both were running their
hands over my mostly naked body.

Ted pulled me off of the bed and I landed on my knees.  I was kneeling
before them and as I looked up They both were unsnapping their jeans and
pulling down their zippers.

Teddy put his hand in my hair and pulled my face to his cock.  I knew what
he wanted and to be honest I wanted it too.  I opened my mouth and took his
cock past my lips.  Out of the corner of my eye I seen Ted reach over to
slowly stroke Trent's cock.

Ted's cock was not small but it was kind of thin.  Trent's cock was about 7
1/2 inches long but OMG it was thick.  After sucking on Teddy's cock for a
few minutes he passed me over to Trent and I took his cock into my mouth.
I had to stretch to get the mushroom shaped head passed my lips and I
wondered how much it would hurt if Trent decided he wanted to fuck me.

I tried not to dwell on how bad the would be for the time being and tried
to do a good job sucking Trent's cock.  While I was sucking Trent, Ted took
my hand and placed it on his cock.  I sucked Trent for several minutes then
switched back to Ted's cock.  I was going back and forth sucking one while
stroking the other.

Finally Ted just sat down on the bed and pulled my mouth down into his lap.
I took the whole length of his cock into my mouth and throat.  His pubic
hair was tickling my nose as he fucked my mouth.

He held my head in place as he shot jet after jet of white hot cum into my
mouth.  I swallowed as fast as I could but when there was so much cum that
it ran out of the corner of my mouth.

As soon as Ted's cock started going soft I moved to Trent's cock.  It only
took a couple of minutes before he came and I was swallowing my second load
of cum for the day.

After I had swallowed both of their loads I was afraid they were done and
that I was not going to get fucked.

Trent sat in my computer chair and told me to get up onto the bed on all
fours.  I was eager to get fucked so I quickly complied.  Trent told Teddy
that he wanted to watch us fool around while he rested and recharged.

I thought Teddy was going to just fuck me but after he joined me on the bed
Trent told Teddy to get me ready for his cock.  Teddy quickly pulled my
panties down and off.  When he spread my ass cheeks I was prepared to feel
his cock enter me.

I was surprised when he started licking my butt and teasing it with his
tongue.  I gasped when he pushed the tip of his tongue past my anal ring.

Teddy started rimming my ass with his tongue and while he did that he
reached around and started stroking my small cock.  When Teddy started
basically fucking me with his tongue I came hard shooting cum all over
Teddy's hand and the bed.  When I had finished cumming

Teddy took the cum he had caught in his hand and started working it into my
ass with his fingers.  Before he was done he had worked 3 fingers into me.

Trent was rock hard now and he climbed onto the bed pushing Ted out of the
way.  I took a deep breath and readied myself.  Even knowing what was
coming it was a shock when he forced the big head of his cock passed my
anal ring.

He grunted as he shoved the entire length of his cock into me.  Good thing
I was stretched and well lubed or I would have pasted out from the pain.

I was begging him to go slow and to be gentle but Trent could not care less
about my feelings, he was wanting to cum again and he was using my body to
do it.  He was making me feel like a cheap whore.

Trent was fucking me hard and rough and I was starting to love it.  As he
drove into me he would grunt and I would let out a squeal like a little
girl.

As he fucked me he started slapping my ass calling me dirty names.  I was
not shocked when I realized that it turned me on even more and I was hard
again.  Actually I had never gone completely soft.

As Trent was thrusting forward I started pushing back to meet his thrusts.
I wanted his cock as deep inside of me as it could get.  Before it was over
I had switched from begging him to quit to begging Trent to fuck me deeper
and harder.  I had turned into a real slut and I did not care all I wanted
was to be fucked.

While Trent continued to fuck me Teddy moved to the head of the bed and I
took his cock back into my mouth and sucked him back to full erection.

Teddy said he did not want to cum in my mouth again and pulled out to let
his cock settle down.  I leaned forward to kiss and start licking his
balls.

Soon Trent grabbed me by the hips and pulled me back hard driving his cock
even deeper than before and held it there.  He filled my ass with a hot
load of cum.  I felt empty when he pulled his cock from my ass.

Trent moved around and sat at the head of the bed with his back against the
head board.  He pulled my head down and told me to clean his cock.  It was
disturbing to me that I did not find the taste unpleasant.  I was kissing
and sucking his balls, running my tongue up and down the length of his
shaft.

While I was cleaning Trent's cock Teddy got behind me and took his turn
using my well fucked ass.  After taking Trent's thick cock I barely felt
Teddy's but he seemed to be enjoying fucking me because he kept telling me
how tight and hot my ass was.

I was swirling my tongue around the head of Trent's cock when Teddy added
his load to Trent's in my ass.  All the attention I had paid to tents cock
while I was cleaning it got him hard again.

When Teddy pulled out Trent took his second turn fucking me and this time
he lasted a lot longer.  He fucked me long and hard and before he was
through I came a second time.  This time I came without even touching my
cock.

I had been well fucked and I laid there exhausted and covered in sweat as I
watched them dress.  They both thanked me for a great time before they
left.

All I wanted was to take a nap but knew I needed to wash my Sisters
lingerie so it could dry and I could put them back in their place before
she came home.

While I was waiting for the clothes to dry I took a shower.  As I soaped up
my body I realized that my ass was sore from the hard fucking that had
taking place.

As the water ran over my naked body I reached behind me and started working
a soapy finger into my but trying to ease the pain.  I stroked my small
cock as I fingered my stretched ass.  As I played with my cock and ass I
fantasized about being group fucked by not just two but a large group of
guys.  The boys taking me one after the other.  I came again in the shower.

That night I wore a fresh pair of lacy pink panties to bed.  I was on the
verge of falling into a deep sleep when the phone rang and I answered it.
It was Trent.  He thanked me again for a great time and surprised me when
he said he wanted to see me again before he headed back to college.

Trent was actually asking me out on a date.  I had no idea how we were
going to make it work but being the slut I had become of course I said yes.

********

To be continued......