Streaming Simon
(From the blog of
"Spymaster34")
=====
Introduction
I'm sure that by now,
you and most of the
internet know about my
little... pet project.
He's the adorable young
boy whose sexy "secret"
exploits have been
getting leaked online
for millions to see.
I've gotten a lot of
emails and requests to
reveal the entire
backstory of the
operation.
Well, firstly I'm sorry to
disappoint the
conspiracy theorists who
seem to think the most
of this. There's no
secret organization, no
sinister ring. I'm one
guy, responsible for it
all.
I don't want to reveal
too much, only that it
all started simply. I
was introduced to the
house in question during
a misadventure in job
stress. Well, it's hard
to explain. Thankfully,
I've dug up my old blog
posts to do the talking
for me. Read and weep.
=====
Entry 1
Hi blog. I'm disgruntled.
I've been called over to
the east side of town
for maintenance at least
four days a week, for
almost half a year. All
I can say is: what a
pain. The young Ms. Ashley
Leighton is the owner of the estate I
have to manage. She's a
prolific "socialite", with
a perfunctory
modeling/acting career,
well-bred and beautiful,
bailed out of all her
problems for all her
life by her Fortune 500
family. Fuck her.
Every time I show up, she
always finds something
ridiculous for me to do,
claiming the fiber-optic
setup "is getting slow
again" or that it
"occasionally cuts out".
Her little brother
probably just downloads
too many movies, and
there's nothing anyone
can do about that. I
learned after a week
that just looking busy
for an hour is good
enough to "fix" all these
imaginary problems - I
just have to role-play a
placebo. Then I walk
around, pocket something
nice and shake her
dainty hand
as I leave. Repeated
theft is helping me
live with my misogyny,
and it took only a few
weeks to learn the
layout of the
house as well as my
own.
Now, any other a
maintenance guy would
just tell her there was
nothing to do, and that
would be that. But there's a reason I
go back
so often...
To be honest, she is a
beautiful girl. She has
a slim tight body and
looked like Katrina
Bowden. So admiring her
body is one thing, but that's not
really what gets me
visiting all the time...
I drive back there, all
those times, because of
her kid brother!
Her brother... Simon
Meyers Leighton. I just
can't help staring at
his tight body and those
big green eyes. That boy
got all the looks in his
family, and he could
steal any man from
little miss Ashley in a
heartbeat. Simon is this
slender angel with
cropped blonde hair, an
infectious smile and a
tight perky ass. He's blessed with fantastic
genes for sexiness, and despite being
clearly a boy Simon
would fool anyone
into thinking he was a
girl if he really wanted
to.
His sister though, holy
shit. What a spoiled
bitch. Does she really
think she can talk to me
like trash just because
I work for a living?
Surely there's a man who
will set her straight...
someday. It sure as hell
won't be me, though.
I have my eyes on Simon.
I see Simon every visit
when I pretend to fix
the internet in his
room. Well... his
"room". The entire home
is a palace, and that
means even his "room" has
two stories and a
stairway. Simon's
surround sound, giant HD
monitor and TV screen
are amazing. It's as
much of a theatre as it
is a bedroom, and the
room got so decked out
with media swag that the developers
soundproofed his room.
Soundproofed... every
visit I could simply
close Simon's door and
rape him for hours. I
wouldn't hurt him, but
oh yes I would rape him
- I'd break him in
before his prime, make
him cum and cum, curl
his toes and lose his
mind. I'd make him
scream and moan and beg
for more at the top of
his lungs, and nobody
would hear a peep beyond
his door
while I fucked him raw
inside.
At least, I like to
imagine I could do this.
Instead, I chose the
slow seduction.
We talked a lot over the
first weeks, about
life, family, his
interests. Simon had a
charmed life, despite
distant parents who just
wanted him for a trophy.
They certainly made it
up to him and his sister
with the full upper
echelon perks. Turns out
he's even been in a
couple of blockbuster
movies, with a small
speaking part in an
action movie and some
other family movies with
animals. He is
certainly double-take-cute enough to play any
Hollywood part. But
whenever I probed subtly
about sex, I could just
tell he was the type to
get filled up by a
man... all of the signs
were there alongside the
obvious physical
indicators. In time I
got to know Simon better
than his shallow sister
Ashley knew him, and I
did it just by giving
the slightest sign of
interest.
I had even earned enough
of Simon's trust for him
to sit in my lap, and
I'd leave my hand on his
skinny leg while we
talked. From the first
time I did that, it was
all I needed to rouse an
instant Simon stiffy. I'd trace a path
along his inner thigh
and just barely stroke
my thumb along his
balls, pleasuring him
through the sheer
fabric. I'd hold him
tight and tease his
ribs, his nipples. I
knew how to make him
moan. I'd talk into his
ear too, whispering
subtle sexual things and
telling him he was
beautiful.
At first I only did this
once every few visits.
But by now it's become part of the
routine, and the petting
gets heavier and heavier
each time. Sometimes I
do my delicate dance
with his body for over
an hour, letting all of
my innocuous touches and
breathy whispers build
up until it brings him
to the edge of orgasm...
and then I keep him
there. I let him recover
a bit... then I bring
him right back to that
teetering helplessness.
Again, and again.
Those are my favorite
moments, when I get to
hold his innocent sex
completely at my mercy.
I love watching him
blush and stutter and
try to hide his boner
from me. He knows
something was off, but
he blames himself. In
fact, Simon is always
so pre-occupied trying
to hide
his wet stiffy, he
doesn't even realize
that I fully intend to
cause it!
But dear god was that
boy shy. I knew he was the type that would be
clinging to you if you
could worm your way in,
but christ almighty he
was just so shy. As soon
as I left, I knew he
would do nothing but sit
at his computer - doing
nothing - playing
games he barely enjoyed
and wasting his rare
beauty.
The impasse was obvious
- he would never let
himself talk to me
openly about sex until I
eventually died of old
age and boredom. I
was manipulating him
into feeling good, but I
never hear him say
a word about it. His
feelings, his
preferences. That made
escalating my touches
too risky. And trust me,
I used all the tricks in
the book, but I just
wasn't the right guy and
eventually I accepted
the fact. He was raised
on a culture fearing all
things sex and "stranger
danger".
Pity that Simon had to
be beautiful and an
iron-clad vice at the
same time. He would need
a different approach,
and well, that's why I
put his entire life
under surveillance.
It started simply - I
just rigged his webcam
at first. I installed
remote access software
to his desktop, and for
almost a month I would see
everything his trusted
webcam saw. I learned
that the boy slept naked
and barely understood
his own body. I learned
his favorite underwear
(a cute yellow Pikachu
pair with a face on the
front and a tail on the
back). I learned how,
whenever Simon was in
school, his hot big
sister liked to stuff
herself with a vibrator
while snuggled in his
bed. She liked to squeal
out for "Daddy". I
recorded everything of
value (some in a
blackmail folder) and I
was certain that Simon
would one day share his
sister's proclivities.
Oh yeah, there'd be
another Leighton
screaming out for
"Daddy" soon enough.
Eventually, my
web-peeping snowballed
into more - Simon's
whole house was state of
the art, and that made
my job so easy. I
installed remote access
to the TiVo, to the
security panels,
everything. And then I
installed more cameras,
microphones, the
she-bang. I turned an
innocent kid's sanctuary
into a panopticon, where
everything he did could
be monitored at any time
without his knowledge.
I also rigged everything I
could think of. His iPod,
his laptop, desktop, TV.
Any time he watched a
show, listened to music,
surfed the web, I would
know exactly what he was
seeing and hearing.
And most importantly,
the software let me
control all the
functions... its
power was amazingly
useful. Was he sleeping too late? I'd
crank that alarm clock.
Was he wearing too much? I
would turn off the AC
and watch him strip down
to his sweaty young
nakedness.
All from a
simple program on my
laptop.
My favorite though? The
"ass-cam". I bought a
couple of novelty spy
buttons, and sewed them
into the seats of his
pants. No way it
wouldn't be fun to see
the appreciative glances
towards his bum. His
clothes are even audio wired too -
I would hear everything
he said and heard.
I
was able to watch him
from cameras everywhere,
in the fancy
glass doorknobs, the
walls, the bathrooms,
inside and outside the
house. There were even
underwater cameras in
their pool - lots of
them. As long as Simon
was home, I could watch
and hear him from at
least four different
angles at any given
moment. I bugged his
sister's cars for good
measure - it would be
useful to know where she
was.
Yes this cost a lot, but
I funded it easily with
the fortune I lifted
from their home.
=====
Entry 2
A few days ago, Simon woke up slowly,
like he always did on a
lazy summer morning. He
was naked, like always,
and he was erect.
Uncircumcised. It was a
normal day, but also his
umpteenth to be watched
remotely by a stranger -
me. Simon yawned,
stretched, and walked to
the bathroom. A crusty
path of precum trailed
up his flat stomach, and
even though he didn't
notice that detail, his
HD cameras sure did.
Simon walked over to the
sink, brushed his teeth
then stepped into the
shower. There, another
camera was rolling. The
naked boy relieved his
urine in the tub, like
always, and like always
his erection was still
there after he
finished.
Simon rubbed at his
penis, grinding a finger
along the head of it.
His finger was slick
with precum, so it
didn't feel
uncomfortable when he
rubbed around his
opening in constant,
steady circles. It felt
good... like always.
I, the maintenance man
had visited again
just the day before, and the boy
always felt the urge to
recreate my touches in
the horny, confusing
days after. He clearly
didn't know how to
masturbate. Simon
touched his inner thigh,
rubbing it. He traced a
thumb over to his balls,
and tried to tease it
tenderly like I would
do. He played with his
nipples and ran a hand
across his ribs.
It wasn't the same -
Simon didn't have my
magic touch. I smiled,
knowing he needed me.
Simon got out of the
shower, and dried up in
his room. He stood in
front of his full-length
mirror and closed his
eyes, touching his body
again. Simon was hunched
over like an awkward
duckling, trying
to enjoy these dirty
feelings. A well-placed
camera behind the mirror
captured everything he
did in real time.
Simon was frustrated.
The boy didn't have any
idea what to do, but
felt such a strong urge
to do it. He went to his
nightstand and took out
a thermometer, dipped it
in some vaseline, and
placed it in his bum. He
twisted it around, then
went on touching himself
in front of the mirror.
The thermometer turned
him on a lot. But he had
no clue what he was
doing.
Like all boys, he was
fascinated with his
young cock. But my goal
was to steer him towards
the deviant side of his curiosity...
the one that drives boys
like him
to put thermometers
in their bum. Simon
wanted to recreate the
naughty feelings he got
from an innocent
experience of
penetration.
But I was going to take
it to another level... I
was going to push him
towards that dark side
of boyhood, and mold him
with those indecent
feelings until they
defined his sexual
character. I decided
to let Simon continue on
his own while I picked
out a good porn file for
his upcoming anal
pleasure education.
Once I found it, I
turned on the TV and let
my selected video
interrupt Simon's
moment. In the clip, a slim
and gorgeous boy was playing
with himself in front of
a mirror, standing much
like he was. Blushing,
Simon's first reaction
was to turn it off right
away. He was afraid of
getting caught, but I
turned the TV back on
and disabled his remote.
This time Simon couldn't
do anything about it, and he was very
interested to see
something very peculiar
- the adorable boy on the
TV wet one of his
fingers... with his mouth!
And slipped it into his
pretty, pink asshole!
Simon was intrigued, and
after watching for a few
minutes he tried it for
himself. Meanwhile on TV
the young teenager was
graduating up to a
dildo, and Simon heard
the cameraman tell the
boy to relax his muscles
and push against the
thick toy. Simon did
this for his finger, and
it felt exquisite.
"Mr. Lynde, it's so
th-thick," cried
out the slender child on
TV. Simon repeated the
boy's words, relishing
in simply a finger. "Mr.
Lynde, it's s-so
thick!"
I laughed at the
exchange. How ironic for
a boy named Simon to be
a mimicker. 'Simon
Says', indeed.
I queued up a few more
videos of cute boys
fingering themselves,
and I made sure to
filter all clips where
they touched their
dicks. If I play my
cards right, Simon will
know only what I want
him to know, and he will
never even learn to jack
off for at least the
next four years. It will
be cruel, but exquisite
- pure, refined and
unadulterated thought
control.
Simon's going
to think the only way to
get off is by playing
with his sensitive ass,
and teasing his
erogenous zones. A
helpless horny lamb, this
boy is only going to
have orgasms if he plays
by my rules. Bit by bit,
I'll make his hotspot
shift away from his
penis to his bum.
Eventually it will shape
who he is, and his cock
alone would never
satisfy him. I'm going
to train this little boy
to develop a genuine anal
fixation.
I even topped it off
with some peer pressure.
Just yesterday, I set up a
fake IM name -
petermaeb10 - and
pretended to be a boy he
met at the mall (got to
love that audio
clothes-wire). I told
him that playing with
his dick was bad! That
this would make it grow
smaller, and that it
makes his future orgasms
"feel less good". Simon
believed it, especially
after I tampered with a
few google search
results to twist the
facts. "Playing with
your penis stunts your
growth!" My fake
websites also claimed
that anal orgasms caused
boys to secrete a
pheromone that made
girls go crazy.
All of this false sex ed
is
ridiculous, of course, but naive
little Simon just eats it all
up. I'm filling his
pretty young head with
carefully selected
half-truths and lies. And
with the conservative
school board in his
district, I doubt he
would ever learn about
sex from public
education.
What a blessing this is,
blog. I now have full control
over Simon's self
exploration. This was
supposed to be a deeply private
and individualistic
process of innocent discovery...
but instead I unlocked
the forbidden reins to
manipulate Simon's
sexual development as I
pleased. Even a parent
doesn't have the kind
of power I have, and
Simon barely has real parents to begin with. He
and his sister are
crossed off boxes in
life's checklist, left
to their own devices.
The shy boy has no real
friends either. Turns
out Simon is isolated
by his wealth, and his
rare petite beauty makes him a bully magnet
- though I'm sure those
boys all wanted to fuck
him if they understood
their own sexual
feelings. I am in the
perfect position to fill
the emotional vacuum in
Simon's life and mold
him into a perfect and
sensual boy.
=====
Entry
3
Sorry guys, it's been a
while!
By the time of my maintenance visit...
hrm, about the week after
my last post,
Simon was completely
obsessed with fingering
his hole. It was the
closest thing he knew to
real masturbation and
every day Simon's skinny little
fingers plowed his pink
entrance with a frenzy.
He
often told his new
confidant
Petermaeb10 about the
frustrating erotic
agony, often describing
the anal lust as a "hot,
really deep itch" that
he felt "all the time
now". I let him know
that it meant he was
physically gifted... of
course, if my plan falls
into place his "gift"
would involve a tight
little present for my
cock as well.
As Petermaeb10, I also
suggested he start
wearing some... tighter
clothing. While he was
resistant to the idea at
first, Simon eventually
picked out some thin
tight tops and shorts
from his expansive
walk-in closet.
Better yet, it was
obvious that Simon
enjoyed it. My erection
almost tore itself from
my jeans when I saw the
boy reach under his
tight half-thigh shorts
and finger himself under
the fabric. He sat down
impaled on a finger,
typing with only one
hand... what a hornball.
When I sent him messages
asking if he felt "hot n
sexy", I saw little
Simon blush and giggle
before typing yes. I
asked him for pictures,
and to my surprise he
actually sent them!
Simon must have had a
bit of a boy-crush on
his new cyber friend.
Petermaeb10: woww you look relli
relli smokin... lol
Simonatorzz: lol... thanks peter
:)
Petermaeb10:
you should dress
like this all the
time...
Petermaeb10: i bet it would make
you feel soo horny
Petermaeb10: wouldnt that be
cool?
Simonatorzz: idk, i think it
would be embarassing
>.>
Petermaeb10:
but that's the point lol, plus...
Petermaeb10:
nobody else knows
how sexy you feel,
only you do
Simonatorzz:
you mean, only you
and me ;)
It was official - Simon
Leighton had a crush on
my fake internet boy.
And I was going to see
how far I could push
him. Being able to
manipulate Simon's
feelings is another big
perk of electronic
control that I am really
growing to love.
Petermaeb10:
btw, are you still...
you know... fingering
your butt?
Simonatorzz: yeah... i'm doin it rite
now >.<
Petermaeb10:
turn on your webcam :P
Petermaeb10: i wanna see your sweet
bod on video!
Simonatorzz: uhh
i dunno.. lol
Petermaeb10:
come onnn... dont be
lame!!! you already sent
a pic
Simonatorzz:
FINE!
Simon clicked the video
button, and for the
first time (to his
knowledge), he let
another person watch him
over the internet.
Except this time, I had
something even better in
mind. After all, it
was time for my
weekly maintenance
visit...
I got into my car and
made a quick drive over
to his home. I texted
him from my iPhone to
keep him busy with
banter, and to make sure
he was still by the
computer.
Petermaeb10:
damn simon your ass is
relli nice...
Simonatorzz: hehehe :P it feels extra
good when you're
watching!
Petermaeb10: i bet, lol i could watch
you forever
I punched in his home
security code and walked
in without being
noticed. Ashley wasn't
home, and it was about
to be just Simon and
myself... I sent a last
line of small talk from
my phone and walked
towards his room.
Armed with the
knowledge of his
sluttish vulnerability, I
made sure to be quick. My
grand entrance was
abrupt and I was
obviously interrupting
something important. Simon was
blushing and frazzled,
hastily closing windows
on his computer.
"Um-uhh hi! I didn't
hear you- didn't hear
you come in today,"
Simon stammered. His
face was glowing red,
and he was so flustered
by his shame that he
didn't even think about
my rude entrance. "I-I
uh, I was just talking
to my- my sister, on
the, online."
"Oh, really?" I replied
in feigned surprise. I
decided to call his
bluff. "I just talked to
her at the
supermarket... she left
her laptop at home, you
know?"
I whisked
Simon into
my lap while he
stammered and strained
to think of an excuse. I
wrapped my arms around
him and teased him about
an online
"girlfriend", mockingly
asking him if he liked
her. When my
playground-style jabbing
looked like it was going
to bring little Simon to
tears of embarrassment,
I decided to change the
subject out of mercy.
I chatted him up about
video games and started
teasing his body again,
as part of our ritual. I
rubbed his responsive
nipples until they poked
achingly through his
threadbare shirt. I drew
the subject towards
girls and kissing and
how his body felt at
night. My steamy
whispers breathed
intimately against his
neck, and other times
against his ears. I let
the electric charges
build, build, and build
in his nerves until
finally I kissed him,
right behind his ear at
his most sensitive spot,
and he moaned. I licked
him there and he moaned
even louder. I caressed
his flat belly and soft
chest from under his
shirt, and I slipped his
shorts off from under
him. I ran a hand down
his smooth inner legs to
make him whimper, shake,
then clutch at his hair
and practically scream
with pent-up
frustration.
Try and cry as he might,
however, there was
little that Simon could do to
escape the plans I had
for him. Especially not
in his soundproofed
luxury cocoon of a room.
Even now I had the
option to drop every
pretense, fuck Simon raw
and spray his tight
little body with my cum.
And I laughed to think
that every boy's room is
supposed to be a
sanctuary - it was a
happy place, a safe
zone.
I laughed because even
in the space of his
safest zone in the
world, this kid was
mine. Exposed, without
the safety or comfort of
the tiniest secret.
I kissed Simon's tender
skin and tongued him
deep in the ear, which
drove him wild... seems
little Simon was a
squealer. I bit his neck
and dragged my teeth on
his skin, letting my hot
breath do its magic.
Simon was crying in
confused ecstasy, but
with state-of-the-art
soundproofing he could
yell as loud as he
wanted. I casually
lifted his right hand to
my face... his guilty
hand. A few of the small
fingers were moist with
spit and they carried a
soft young musk.
"Mmh... I wonder where
these little fellas have
been," I smirked. Simon
tensed up and froze, a
look of genuine
humiliation creeping
onto his delicate face.
How could I possibly
have known about his
bum-fingering marathons?
How indeed...
"Wh-what do you mean?"
Simon asked in a weak
voice, feigning
ignorance. He was
glowing red, mortified
to even think that I was
on to his dirty secret.
"Don't pretend with me,
you little pervert," I
whispered back. Simon
groaned adorably - the
boy knew he was busted.
Did he really think I
could tell just by
sniffing the soft musk
on his fingers?
Nonetheless Simon tried
to cover his face in
deep, earnest
humiliation. But I
didn't let him have the
comfort of hiding his
face. Whispering that
nothing he told me would
surprise me, I looked
Simon straight in the
mirror. I put his thin
fingers in my mouth and
sucked on them, making
them wet. I lifted his
legs up with an arm,
exposing his little
package and pink,
still-wet hole to the
mirror.
I exposed his freshly
fingered ass to my
hidden mirror camera. It
winked a few times in
reflex, a drop of
Simon's spit dripping
out of the ripe
entrance.
"Why don't you show me
what you've been doing
with your little
girlfriend,
hmm? Then maybe I won't
tell your sister about
the little slut she has
for a brother," I said,
taunting his reflection.
Simon hesitated, but I
guided his hand towards
his quivering hole.
"Make yourself cum... if
you can," I crooned. I
doubt if Simon even knew
what "cumming" was,
exactly - he had surely
never experienced it to
my knowledge. I pressed
his fingers against his
snatch and his inner boy
slut did the rest,
slipping two fingers
inside of his delicious
anus.
"Auhhhwwhh, jeeezuss,"
Simon moaned. He swayed
his lithe young limbs
and I couldn't help
pleasuring his body with
him. I cupped a hand on
his ass, spreading it
open. Another hand
grinded his hard little
nipples while I licked
and dragged my teeth on
his earlobe.
"Ahh... you're so
enthusiastic, baby
boy... but you just
can't hit that perfect
spot, can you," I
teased. "I bet it's just
driving you crazy."
Agreeing subconsciously,
Simon pushed his fingers
deeper, twisting them
and moaning with
frustration. It was a
real stroke of genius
not to let him learn
about "proper" jacking
off - watching him work
up his hole in person
was a real treat. I
grabbed his arm and
pulled him away from
himself, relieving him
of his futile attempts.
"Why don't you let me
help you out?" I
offered, with smug
condescension. I put
well-manicured my
fingers in his mouth,
and he sucked on them
instinctively. "I'm
going to give you just a
tiny taste of what a man
can do... especially to
a hot little cunt like
yours."
"Get ready," I smiled. I
rubbed Simon's pretty
sphincter with my thumb
and relished how much I
was going to blow his
mind once I really got a
chance to fuck him good.
"This is gonna feel a
whole lot bigger than
the best you've got, and
I promise it's not even
close compared to what I
can really do to you.
You'll see soon
enough... yeah open up
there, nice and easy."
I pressed against
Simon's tight virgin
entrance, and I slipped
in my middle finger to
the first knuckle. He
grunted. Then I passed
my second knuckle, and
that's when I wiggled
"come hither" against
Simon Leighton's
precious and hungry
prostate. He nearly
combusted.
"Ooohh... yeahh that's
good isn't it? That hits
the spot," I cooed in a
lilting voice. "Your
little boy fingers were
just too short to get
there, weren't they? Hm,
weren't they?"
"Y-yes! OhhHH my goddd,"
Simon squealed in
writhing awe. "N-no
mmore, oh g--... ohhh..."
"But Simon that wasn't
even the whole finger,"
I bantered. "What I push
the rest of my middle
finger into your
beautiful little
spit-lubed hole, like
this... oh, you're
squealing so good... I
bet I'm already further
up your snatch than
you've ever been
yourself. What are you
even doing without a man
like me around..."
"No m-more," Simon
begged, slightly
drooling. "I can't ta...
ohh jesus ohh my god..."
"What do you think about
the second finger, huh
champ?"
He practically raised
the dead in protest but
I slipped in my
spit-lubed ring finger
to the hilt and felt it
stretch Simon's hole
further. Now there were
two of my thick, long
adult fingers snaking
into his innocent body.
As tight as his cunt
was, it naturally sucked
my fingers in as though
hungry for more. And
funnier still, Simon's
mind seemed to think it
was too much!
I was aching to fuck the
boy silly with my
sizable cock, but just
the fingers in Simon's
ass seemed to be more
than the hyper-sensitive
youth could handle for
now. To think - I'd
already started turning
this perfect boy into a
bona fide anal slut,
born to cum not by a
woman's body, or even by
his own hand, but by the
irreverent and sinful
abuse of his perfectly
formed rump.
"Are you imagining
my fingers are a
cock, Simon?" I
taunted him, giving
his nipple a good
squeeze. Simon
didn't have much of
a poker face, and it
was obvious I was
right. Planting my
fingers as deep in
as they would go, I
continued my verbal
assault on my
mewling, addled
boy.
"Mmmh, yeah Simon,
go ahead and pretend
it's my cock... I
like hearing you
moan like that. And
I know you don't
even mean to make
sexy little noises
like this... you're
normally so quiet
and private! Oh
there it is, I can
see it on your face
- this is all so
embarrassing for
you, hm?"
By the third finger,
Simon was more than
ready to blow to kingdom
come. But the sadistic
man of patience that I
am, I decided instead to
take it nice and slow.
While I fingered his
helpless virgin hole, I
kindly asked Simon to
turn on his Blu-Ray
player. It was
voice-activated.
As I expected, his TV
started to play my
pre-picked montage of
erotic videos and
pictures. They all
depicted boys his age
getting fucked,
fingered, bound and
teased. Some of the
pictures were Japanese "shota"
art, and he responded
especially well to
those. I interviewed him
extensively on every
video and picture,
making sure his innocent
mind soaked in every
sensual detail, and that
he was fully imagining
himself in their
positions.
Pretty young boys like
him are so easy to read
and manipulate.
=====
Entry
4
I kept Simon squealing
like that for an entire
afternoon. I
made sure to figure out
exactly what he was
thinking during each
second of my prepared
footage. Every time I
learned something new
about my slutty young
consult, the grin on my
face grew wider and my
cock grew harder. I was exhilarated to
be tainting his mind
with lust.
"So tell me Simon, how
do hot little boys like
you get to feel good?"
"Auhhnnnh," he moaned. I
was just winding him
back up towards orgasm
again, and his face was
glowing red from the
intense edging.
"L-little boys like
me... have to play with
their ass?"
"Very good, Simon! You
won't even think about
touching your little
dicky like a bad boy,
isn't that right? We
can't even call what you
have a cock. You'll only
play with yourself in
the bum!"
Simon nodded and panted
helplessly in pleasure.
His O-faced mouth curled
with a smile when I
kissed his neck, happy
to receive the praise.
"Now Simon, I have to go
soon. So I won't have
time to give you what
you really deserve...
but I do know how you
can make yourself feel
good while I'm gone."
I pulled out a few items
from my work bag. One
was a cell phone with my
number programmed into
it. Next, I pulled out a
very expensive, very
uniquely designed butt
plug designed to get any
boy's ass boiling with
pleasure. It was baby
blue in color, and built
to target the prostate
while its length would
prepare a virgin ass to
be deeply fucked. The
base of the toy narrowed
around a discreet flare
knob, which would keep
the plug inside of
Simon's bum for extended
periods of time.
"This is Big Bill...
he's gonna be your new
best friend from now on,
okay? And this phone is
what you'll use to call
me while you're putting
him inside you for the
first time. You can even
do it tonight, right
after I leave."
"It's... He's... so
big," Simon replied
huskily. The boy was
still impaled on my
fingers, and I rubbed
the length of the plug
along his inner thighs
to let him know how much
would be inside him.
"Yeah he's big," I
teased reassuringly.
"But you're going to
give him a try, I know
you will. You're a
natural born boy-slut
and you'll never turn
down the chance to make
your ass feel this
unbelievably good.
You're too curious!"
"I don't know about
that," he moaned. My
fingers were wiggling
deep in his ass, and I
could feel him tense up
whenever he even looked
at Big Bill. His button
nose scrunched up, full
of hesitation and
concern.
"I don't think I'll
really use it... it's
way too big."
I smiled at him, and
pulled out my fingers.
He let out a needy gasp of
pleasure when I pulled
out, and that was enough to
let me know what was
sure to come next.
It took Simon all of
fifteen minutes to call me on my
phone, spilling his guts
to me while he pushed
the fancy dildo further
and further inside his
hole. As kinky as ever,
Simon was in his sister
Ashley's room. He was
squatting down on the
ground, resting the base
of Big Bill on the floor
while he lowered his ass
onto the impaling toy.
It was dripping with his
sister's lube.
I ogled Simon on the
video, intently watching
his slim body despoil
itself. It also made me
smug and unbelievably
hard whenever I noticed
the little
micro-expressions of
shame, hesitation, and
fear. I was witnessing
his ultimate
vulnerability without
his knowledge, and I got
to see how his
inhibitions were swept
aside by the sexual
curiosity I so carefully
cultivated.
And of course, I decided
to open up a link on
several image boards and
livestream. The viewers
could toggle between any
one of the cameras set
on Simon, and they could
hear every word I said
to him over the phone.
My channel exploded to a
thousand viewers in the
first five minutes, and
that's when I knew the
fun would begin.
"Why is having Big Bill
in your ass making you
so hard?"
"I dont know," Simon
whispered. How naive. He
fidgeted weakly,
exhausted but unable to
control the rolling
shudders of ecstasy. "I
want... I wanna take it
out. Take him out, I
mean."
"Ok, I'll help you with
that," I lied. "Why
don't you spread your
legs some more, and push
your muscles out against
Big Bill? Just keep a
finger pushing against
the hilt."
"Ohhh!"
Simon complied, moaning
in surprise - the
tapered plug slipped
several more inches of
itself deep into his
hole. It was physics,
working against the
hapless boy. Simon
realized he was tricked
and tried to pull out
the toy, but his muscles
tensed up with the
slightest movement. The
contractions pulled even
more inches of the toy
inside him, until it was
so deep in Simon's
virgin flesh that he
could barely move.
"Nnnnhh I just need to
take him out for a
second," Simon whined,
moaning helplessly. He
tried to pull it out
again, but Big Bill was
already too deep.
Moreover, the
bum-clenching was what
slipped those extra
inches inside him to
begin with, and now they
were keeping them
there.
"Feel how deep he is
inside you," I cooed.
"Tell me what it's like
to be Big Bill's pretty
little bitch."
"MMmmnhhmmh... I don't,
nnh, I don't know,"
Simon moaned helplessly.
His precum was leaking
all over the floor. "I
just mmmhh... just want
it to s-stop..."
Simon started to cry,
pathetic and confused
and horny.
As horny as he'd ever
been in his life.
"Oh, Simon baby, it's
obvious what's going on
in your ass," I dirty
talked. "I can tell from
just your face that you
can feeel every
bit of Big Bill, can't
you?"
Simon pressed his hands
to his chest and squealed in
confirmation.
"You can just feel him
rubbing and dragging
against your nasty,
naughty sweet spots." I
checked the stream, and
it was exploding with
comments at 12,000
viewers.
Simon was too young to
be prepared for all
these feelings, and he
was gritting his teeth
from shock. It didn't
hurt, in fact he felt
intense throbbing
pleasure. But it wasn't
the pleasure alone that
was overwhelming him....
it was the penetration.
"Let me tell you what
you're feeling, hmm,
sweety? You're feeling
Big Bill's girth, his
length, he's so deeep inside
you... and it's all too
much for you to
understand isn't it
baby?"
"NNnnyhhahhhh!"
Simon screamed in sexual
overload. "Pl-please!"
The beautiful young boy
couldn't handle it - the
subconscious knowledge
that this inanimate
object was in control of
his entire body. That he
was at mercy to a simple
butt plug. Simon was
used to holding the
reins of his own
penetration, able to
withdraw his fingers at
will. But now this
thick, scary plug was
nestled so deep inside
him. His body wanted
nothing more than
sphincter to be granted
mercy and safely close
his body off in peace.
This... this insolent
plug was keeping Simon's
sacred passageway opened
wide and beyond welcome,
leaving him defenseless
and debased.
The channel was at
19,000 views now.
Already some people had
figured out who the boy
was, and a few websites
were up to enshrine his
sexual exploration.
Others were posting
stylized photoshops of
Simon's bliss. A few
were even saying they
lived in the same
neighborhood - they
couldn't believe how big
of a slut he was, and
they were laughing their
asses off to see him
played like a fiddle.
This all felt completely
out of the boy's
control, and it was. I
set the vibrations to
max and had them come
and go in waves. Then I
turned on the "wiggle"
feature, which made the
vibrator slither and
bend itself against his
flesh like a snake
trying to push deeper
and deeper inside of his
body. Simon's hands
clutched feebly at the
flared base, hoping to
keep it out but to no
avail - the last few
inches left of Big Bill
had now "wiggled" itself
into his bum along with
the rest.
With the entire long,
lubed toy inside him, a
shell-shocked Simon
plopped his round perky
bum against the ground
in resignation. Big Bill
was sapping the power
from his body and making
him legitimately afraid
of what his "new best
friend" could do to his
body.
Simon wasn't ready to
feel this way, and he
didn't know how to
process the shockwaves
of pleasure screaming
through his body. And he
DEFINITELY didn't know
how to process the
sudden vibrating inside
his ass when I turned it
on from remote control.
"MMMMMmmmmnnnnnhhhh!!
Aawhhh my goddddd!"
Simon moaned out loud.
"What the hhellll...
this is... unnnhhhh!!"
"There's only a few more
inches left," I
beckoned. "Just sit
yourself down on the
rest of him and tell me
about how it feels to
have Big Bill completely
inside you."
"Annhh! Ahhnnh! It
f-feels... mmnh? So
warm, an-and deep, and
there's so so much,
ohmygod there's so
much!"
Simon's body started to
spasm uncontrollably,
and he clutched his
stomach as though he
were cramping. But there
was no pain - only
overwhelming sexual
stimulation.
"It's too goood," he
moaned. I could tell
this was the time to
push Simon to the
breaking point, so I
turned the remote
control's dial to the
setting in black - the
one labeled 'boybuster'.
I could only imagine
what combination of
writhing, rotating,
pulsing and vibrating
was being used to bring
Simon's tender pink ass
over its limit.
"You're going to cum
now, Simon. You don't
even know what that is,
to cum,
but Big Bill is gonna
make you cum so, so
hard. Just look at
you, you're only a
little boy but you're
already the biggest slut
I've ever seen, stuffing
such a big thick rubber
cock in your hole so you
can feel what it's like
to have a man..."
"UUNNnnnhhh-nnnooo...
annh... annhh!" Simon
became incoherent as he
neared the first orgasm
of his life. His pert
bubble butt was grinding
against his sister's
floor now, mashing his
pink hole against the
base of the toy. Simon's
lithe young frame shook
uncontrollably, the boy
clutching at his stomach
and reverting almost to
the fetal position as I
manipulated his body to
an explosive anal climax
for tens of thousands of
viewers to see.
"Annhh! Annhh! I
c-can't...there's t-too
much... ohmygod ohmyg...anh...
annNnhh... aaAAnNNHH!"
"You're cumming now," I
whispered along with his
screaming orgasm.
"You're coming because
it's the first time
you've been fucked so
deep in your ass, and
let me tell you - Big
Bill ain't going
nowhere, and I'm making
sure it's only going to
get better with every...
single.. day."
"W-w-waai-ooooohhhhHH! FFfffuuuuuuuckkkk!!
AAAnnNNNhhHH!
AAUuGGghhhH! " Simon
cried. Tears of
confusion and joy
streamed down his
model-worthy face as he
lost himself in
orgasm. I never stopped
dirty-talking him deeper
and deeper towards
ecstasy, and it caused
his innocent body to
roll in pleasure longer
than any I had ever
seen.
Simon had over 43,000
viewers by the time his
orgasm was complete. He
wasn't old enough to
produce sperm, but he
still managed to leave a
shamefully large pool of
precum in his wake. Men,
women, girls and boys
alike were watching as
Simon Leighton slowly
came down to earth, all
of them knowing that an
obscenely large sex toy
hidden in his ass had
just brought him to
climax. Thousands
demanded more, and a
handful even claimed to
go to his school, and
that they would film him
as well from a distance.
My dummy inbox was
filling up with
requests, ideas, and
praise - this boy was
now the center of an
entire voyeuristic
community.
I picked out the more
interesting comments and
decided to go with a
more daring suggestion -
I instructed Simon to
keep the plug inside him
for the next 5 days, and
to only remove it when
he needed to. In his
state of weakness, he
agreed without even
realizing he could say
'no'. I told him to put
his Pikachu panties back
on and go to bed -
without cleaning up the
stain in his sister's
room. Again, he agreed.
Simon was on autopilot,
riding waves of shame as
well as a sexual high.
I decided to leave the
stream on indefinitely.
The community deserved
to see what I got to
see, and they had proven
to have some good ideas
as well. A few viewers
offered to set up
cameras at his school
classrooms and even in
the boy's room he
preferred to go to. With
constant knowledge of
his whereabouts, I
planned to abuse Big
Bill's 'boybusting'
abilities at the worst
of times for my stuffed
little nymph.
But not of course,
without leaving Simon a
good night message as I
went to sleep.
Petermaeb10:
btw simon, you left your
webcam on
Petermaeb10:
and you left your door
open
Petermaeb10:
while you were at your
sister's room :P
Petermaeb10: i could hear you cumming
all the way from here
Petermaeb10:
you've gotta let me
watch you play with big
bill!!