Date: Fri, 15 Jun 2007 08:38:15 +1000 (EST)
From: jack rabbit <looseboy_girl@yahoo.com.au>
Subject: Loose Ends: Part 1

The following story is one of the horny encounters that i have
experienced over the last 7 years or so. Everything in this story apart
from the names is true. The following story is from before i turned 18
years old. All of the following stories will be when 18 years and older.
I hope you enjoy.


When i was about 13 i became fascinated by womens clothing. Ladies
lingerie to be more precise. Whenever my parents went out i would always
raid my sisters panty draw and wear her panties around the house. This
was the beginning of my journey. Over time i added more womens clothes
and eventually make-up to my little dress ups.

When i was about 15 i found a vibrator in my sisters draw. This was where
my fun really began. Initially i would just turn it on and feel it
against my cock and balls. The tingle that i felt was amazing and after a
while curiosity got the better of my and one day i smothered my tight ass
with vasoline and pushed the plastic vibrator into my virgin ass. It was
not a particularly large vibrator, only about 6 inches and not real thick
so while it hurt a little at first, my ass quickly adjusted to it sliding
in and out of me. Damn it felt good.

By the age of 16 i had never been with another person, Male or female.
Physically i was still more attracted to girls but when my hormones got
the better of me i had more of a craving for cock than pussy even though
i was not really attracted to guys. This was about to change.

My family lived in a small apartment building containing only 4
apartments. Ours was on the ground level. There was two apartments on the
ground level, one larger apartment upstairs and a small garden flat out
the back.Upstairs lived a middle age couple with their daughter who must
have been about 21. I was not sure of her real age i just knew that she
was out of school. All i know was that she was damn sexy and for a 16
year old boy she would get my blood pumping. In the other ground floor
apartment was an elderly woman. She pretty much just stuck to her self
and bothered no-one. The garden flat had been empty for a while but one
day we noticed someone moving in. It was a couple of men moving in. They
would have been in their 50's I'd say. One maybe a bit older in his 60's.
I was still a bit naive and it took me a while to realize that they were
a gay couple. They were nice enough and never bothered anyone so no-one
in the building seemed to care.

My bedroom was on the side of the building. The window was at about head
height to a six foot person. There was no path down that side of the
building but i would often hear the guys in the back flat walk through
there when they came home at night. It was not loud footsteps but over
the years my ears had become accustomed to hearing anyone that may be out
there. One night it was real hot and i was laying in my bed wearing just
my boxer shorts. I was watching my television which was located at the
end of my bed in a cabinet that had glass doors where the VCR and stereo
sat. I had the window open and the blind pulled most of the way down bar
about 10 inches at the bottom so that the breeze would come through. As
per usual about 9:00pm i heard the footsteps up the side. Once again they
were not loud and if it were you walking you may think that no-one could
hear you but my ears had become sensitive to hearing people out there so
i very rarely missed anything. The footsteps approached but on this
occasion they seemed to stop much sooner than usual. I had a feeling that
someone was looking in my window at me. Without turning around to look
over my shoulder i used the glass window on my television cabinet to try
and catch a reflection. To my surprise i could just see the a reflection
of a mans head from about the nose up looking in my window. It became
evident to me that it was one of the men in the back flat as the man had
glasses on that appeared to be the same as the guy out back. I didn't
know how to react so i just kept looking at the reflection out of the
corner of my eye while it appeared i was watching television. Eventually
i was convinced that it was my neighbor and i actually started to get
aroused. I flicked through the channels on cable and found Baywatch on
one of them. Baywatch was heaven to most teenage boys. I reached down and
grabbed myself on the crotch. I didn't pull out my cock just yet i just
rubbed myself. After a while i eventually pulled out my now hard cock and
started stroking it. This stroking eventually became more frantic and it
wasn't long before i shot cum all over my stomach. Just after that had
happened i heard the faint footsteps walk away. Over the next few weeks i
would leave my window open on hot nights and the blind slightly up. On
about 3 more nights i heard the footsteps stop and once again i put on a
show for my new peeping tom friend.

AS i have mentioned the girl in the apartment upstairs was hot. Just
looking at her made me hard. My sister was about to move out of home and
i had to find another way to get womens panties to wear. One afternoon i
noticed that the upstairs neighbors had left some washing on the line. I
noticed one of the rows had about 5 pairs of panties on there, several
thongs and some bikinis. My folks were out that night as were the guys in
the back flat. I snuck out to the clothes line and took 2 thongs and one
full bikini from the line, both the top and the bottoms. I felt guilty
about this but my hormones were in control of me and they took what they
needed.

My parents were to visit my aunt out west on the coming weekend. They had
asked if i wanted to go but i had to play rugby on the Saturday so i
couldn't go. What a pity. I was a responsible kid so my folks had no
problems leaving me home alone. My sister was due to move out the
following weekend but she was away with her boyfriend on this weekend so
it was just me for the Saturday night. During the afternoon i had watched
a few videos from my dads porno collection and i was feeling real horny.
I must have masturbated 5 times that day but within an hour i was horny
again. I pretty much spent the whole afternoon with my sisters vibrator
up my ass and my hand on my cock.

That night i was laying in bed with my window open again.AS i was home
alone i was really hoping that my voyeur friend would make another visit
but this time i had a surprise for him. Little was i to know that he
would have a big surprise for me later that night. I dressed myself in
one of the black thongs that i had taken from the line and i also put on
the black bikini top i had also taken. I put one of dads pornos in the
VCR and laid there eagerly hoping that i would get a visit. To my delight
i heard the footsteps right on cue at about 9 o'clock. I looked into the
glass door of the cabinet and i could see his reflection. I was really
horny but also very nervous. How far was i to take this session? AS usual
i pulled my cock out and started to gradually pull on it. Fuck i was so
horny by now. It was then that i went even further. From under the covers
next to me i pulled out my sisters vibrator. I reached onto my bed-side
table and grabbed the vasoline and applied some to my asshole. I stuck
one finger up my ass and massaged the lube all around. kept my finger in
there for about a minute, rotating it around and rubbing the lubricant
all around my tight hole. Pulling my finger out I slowly pushed the
vibrator into my loosening ass. It felt amazing as the vibration went
straight through me and i could feel my balls tingling. I kept going with
this for a few minutes until i felt like i would explode so i pulled the
vibrator out of my wet ass. I swung my body around on the bed so that my
feet were facing the window and positioned myself on my knees facing away
from the window. I lent forward so that i was leaning on the bed end and
shoved the vibrator up my ass again. The position i was in i was fucking
myself doggy style. Due to the change of angle i couldn't see my voyeur
in the reflection anymore but i knew he was still there.

At this age i still hadn't been with anyone yet but i knew that tonight
would change that. Tonight i would lose my virginity. Not the way most
guys do though.

After fucking my ass from behind for about 5 minutes i pulled the
vibrator out of me again and laid back on the bed. I was real nervous
now. I was about to confront my voyeur. How would he react. In a spring
like motion i sprung up and spun around to face the window. He looked
shocked when i saw his face. I didn't say anything at first. I just
grabbed the vibrator and stuck it in my mouth and sucked it like a
lollipop. He just stared at me for about a minute. I pulled out the
vibrator.

"The front door's unlocked" Was all i said.

Within moments he was gone from the window. He seemed to take a bit
longer than i thought but i waited on the bed for his arrival.

I was still nervous. I had always thought that my first sexual encounter
would be with some fat chick or the local slut but not like this. John
was probably about 55-60 years old. He was slightly overweight and had a
pretty dark tan and short dark brown hair that was balding slightly at
the back. In no way was he a good looking man but it was at this moment
that i realized that i was attracted to average looking middle age to
older men. It must be some sort of father figure type thing that turns me
on. I guess i wanted someone to take control of me.

Entering the room John just stood there watching me for a moment. I just
laid there rubbing myself up. Eventually he came and sat on the bed with
me. I had no idea what to do next. I was hoping that he would take
control. I just wanted to be his little bitch. He put his hand on my leg
and started rubbing up my thigh. What a strange feeling. Here i was in
the girl upstairs underwear and a vibrator in my hand being felt up by a
middle aged man in my parents house. I strange feeling but real fucking
arousing.

He worked his hand up my leg eventually placing his hand on my panties
over my now throbbing cock. Gently he started rubbing my cock. I don't
have a massive cock only about 5 and a half inches when erect but the tip
was sticking just out of the panties as he slowly motioned up and down my
cock with his hand. With his other hand he placed it under my bikini top
and started to tweak my left nipple. I had never felt this but damn it
was good. He started to tweak it harder and while it hurt a bit it felt
so good i pleaded for more.

It wasn't long before John unbuckled his jeans and pulled his cock out. I
had never seen another erect cock up close and i was in awe. While i had
a small little cock, John's was not huge but a very inviting 7 to 8
inches long and about another half as thick as mine.

He grabbed my hand and placed it around his rod. Naturally i started to
pull it slowly up and down. He was so damn hard. I stroked him for a
little longer before he stood up right in front of me. I knew right then
that i was about to suck a real cock for the first time.

"Suck it just like you did the vibrator" He told me.

I brought my head towards it and stuck my tongue out to lick the top of
his cock. Just like the vibrator he said, so here goes nothing. With that
i wrapped my lips around the head of his cock. I had to open my mouth
wider than i did for the vibrator, but it was still comfortable. I took
more of it into my mouth until i was about half way down his shaft. If i
took anymore i would start to choke. That clearly didn't bother him as he
put his hands behind my head and pushed his cock even further down my
throat. I started gagging but he told me to just relax my throat. I tried
and it took me awhile to adjust but eventually i had him about 3 quarters
of the way into my mouth without gagging. I think he realized that i
couldn't take any more at this early stage so he stopped pushing further.

So this was sucking cock? I could now safely say that i had given a blow
job. I kept sucking real hard on his throbbing member until he pulled
away from me.

" How far are you prepared to go?" He asked
" How much do you want to teach me?" was my reply.

I knew that he wanted to fuck me. He had seen me stuff my sisters
vibrator up my ass. He knew that i wasn't baby tight.

" I'm going to teach you everything a good little girl needs to know" He
said to me with a devilish grin.

With that, he told laid me on my back and held me under the knees. He
wasn't going to fuck me yet. He grabbed my sisters vibrator and slowly
pushed it into my already wet ass. Slowly he pushed it in and took it all
the way out. He kept going with this motion. Pushing it all the way in
and then pulling it all the way out for me to look at. One time he pushed
it in and left it there. He grabbed the vasoline and rubbed some onto the
tip of his cock. I knew that it was time for me to feel a real cock in my
ass for the first time.

Pulling the vibrator out of my ass he positioned his hard cock on the rim
of my wet and ready love hole. Leaning towards me he pushed firmly until
the head popped just inside. I grimaced a little as this was bigger than
the vibrator and my young ass had never felt something this size. Slowly
he pushed more until he was about half way in. I was hurting yet in
heaven at the same time. He started to slowly motion in and out of me.
Never going beyond halfway into me.I must have felt tight to him as he
tried to go further but had trouble. He fucked me while staring at my
face for about 10 minutes. I became more relaxed and eventually took
about three quarters of his cock in me.

"Get on you hands and knees and face the window" He demanded.

"OH FUCK!!" I yelped.

To my surprise as i faced the window i was looking straight at Johns
boyfriend Brad who was looking through the opening. I went to jump up but
John held me there.

"It's ok" John assured me.

At that point John put his cock against my now red sphincter and pushed
himself into me again. In this position he seemed to slide into me easier
as he started to fuck me quite hard now. His rhythm really increased as i
could feel his balls slap into my balls. John kept fucking me like the
little whore that i was soon to become, thrusting his hard cock in and
out of my young but eager asshole.

Brad was still watching through the window. He didn't join us. John
handed him my sisters vibrator. Brad shoved it into my mouth. I was being
fucked up the ass doggy style with my sisters vibrator being shoved in
and out of my mouth by my new lovers man friend.

After about another 10 minutes John pulled out of me and forcefully threw
me over onto my back. Straddling my chest he proceeded to jerk off in my
face.

"You ready?" He asked
"For what?" I naively replied.

Then without warning one shot of cum rocketed out of his cock onto my
face, followed by about 5 more shots. He pressed his cock against my lips
and told me to lick it. I did and i must say that i hated the taste that
first time. Not anymore though!

I laid there with my face covered in cum. John collapsed onto the bed
next to me.

"Well aren't you the little slut" Brad degradingly said to me through the
window. And then walked off after throwing the vibrator at me.

I laid there a bit confused. Was i gay now? How could i be i still liked
girls but i couldn't imagine fucking a girl would be as much fun as this.

"You had better go and have a shower" John said.

I did just that. When i came out of the shower he was gone.

John and Brad lived in that flat for about 2 years, until just before my
18th birthday. Brad never liked me. He never said anything to me he just
gave me awkward looks when i saw him. I probably fucked John about 20
more times over the next few years. These were my only sexual encounters.
I still hadn't been with a girl yet i still wanted to. That time would
come. I could only fuck John if my parents were out. Each time i would be
dressed in girls underwear. I'd even put on a skirt a lot of the times. I
really must apologize to the girl that lived upstairs as she must have
lost a lot of underwear over this period. AS i said i felt guilty but
when my hormones are raging i can't control myself.

When John moved i had a bit of a dry spell for a while. Until about 3
weeks after my 18th birthday. But more about that next time. My
adventures have only just begun.


I really hope you enjoyed hearing my story. AS i said this is the only
story i will write where i was under the age of 18 as they were my only
sexual encounters at that age. I promise to write more soon when you will
see what a real slut i have become. If you wish to give me some feedback
on my story or ask me a question you can write to me at
looseboy_girl@yahoo.com.au