Date: Thu, 9 Oct 2008 19:10:20 +0000
From: criedfornoone (at) hotmail (dot) com
Subject: Babysiting Billy (gay/young friends)

Copyright 2008 Derek W. all rights reserved. This
copyrighted work may not be distributed for commercial use
without express written consent of the author. This work may
be copied or archived on any non-profit website.

DISCLAIMER READ FIRST: WARNING this work contains graphic
descriptions of sexual acts of homosexual nature. If that
sort of thing offends you stop reading now. Although this
story is entirely fictional and all characters are portrayed
by adults 18 years or older, the story is about a sexual
relationship between a teen and a preteen boy.


This is my first post of a story on nifty Email me at
criedfornoone (at) hotmail (dot) com


Jack had just turned 14. His next store neighbor Julie was a
single mother raising two children. She decided to start
going back to school so she could provide a better life for
her 10 year old daughter Gina and 9 year old son Billy. She
worked days and was going to be going to school at night,
two nights a week and she needed a cheap babysitter. Of
course when Jack was asked he didn't pass up the chance.
Having just turned 14, five dollars an hour for 10 hours a
week seemed like a pretty good deal. Of course, money wasn't
the only reason he was more then happy to watch her kids.
Since jack started puberty over a year ago, he had always
had a strong attraction to younger kids. Boys age 8-12 were
where his interests lied. So far though his sexual
experiences with guys were limited to mutual masturbation.

Jack was to Watch Billy and Gina Monday and Tuesday from 7pm
until 12pm while their mother was at School. The first day
when he knocked on the door he was greeted by Billy. Billy
had medium length blond hair, blue eyes. He was skinny and
about 4' 4". Billy smiled at him and led him inside. Gina
was sitting on the couch watching TV. Julie was in the
kitchen getting ready to leave. She Gave Jack some final
instructions, told him dinner was in the microwave and left.

The first two nights were fairly uneventful. He watched TV
with the kids; played video games with them on their XBOX,
Micro waved them dinner and sent them to bed. Billy and Gina
were both somewhat shy kids who were excited to have the
attention of a babysitter and were eager to please. On the
second night he had gotten in a playful wrestling match with
Billy. They wrestled around on the couch and even though
jack was much taller and stronger, he let Billy get the
upper hand every now then to make the match a bit more fun
for him. Jack found himself getting very excited by the
close contact with Billy's smooth little body. By the time
they were half way through the match Jack had developed a
strong erection that was straining against his boxers. Jack
tried not to let his throbbing boner press against Billy but
at one point he was on top of him and found his hard cock
pressed against Billy's arm. Billy gave Jack a funny look at
first but then the match went on.

That night after Julie came home, Jack went home and
immediately to his room to relieve himself. He pulled out
his long slender erection and jacked himself to a powerful
orgasm. His cum sprayed everywhere and some even landed up
on his chin. It was then that Jack decided that he had to
get Billy in to bed if was willing and he began to come up
with a plan.

The following Monday. When jack came over things went as
usual at first. They played video games, Billy and Jack
wrestled. At around 10pm Gina went to bed. This was what
Jack had been waiting for. Jack waited about 15 minutes
until he was satisfied Gina wasn't going to get back up and
he made his move.

"Hey Billy you wanna see something neat on the computer?"

"Sure."

"Come on ill show ya."

They went into the other room where the computer was and
Jack opened an internet browser.

"Have you ever seen a naked girl before?"

Billy said nothing at first then answered "no"

"Do you wanna?"

Billy thought for a moment. He had never seen naked girls
before but the thought made him very curious despite the
fact that he was extremely nervous about it. "I guess so" he
answered

Jack pulled up a website that had picture of young women in
various states of undress. Most of them were alone but some
were performing sexual acts with guys.

"Are they having sex?" Billy asked

"Yeah, see that guy has his dick in that girl's pussy?
They're having sex." Then Jack clicked on one of the free
preview videos. A girl appeared on screen. At first she was
touching her self then the scene changed to her giving a guy
a blowjob. The guy moaned as he shot his load all over the
girls face.

"What are they doing?" Billy asked

"She was giving him a blowjob. Sucking his dick. At the end
when the white stuff came out of it, that was sperm. When
you get a few years older like me you'll make sperm too. And
when it comes out of you it's the best feeling a boy can
have. At the end he shot his sperm on the girls face, but
usually a girl will let the guy shoot it in there mouth and
then the girl swallows it because it feels better for the
guy that way"

"Does it taste bad?"

"No it's just a little salty"

"Can you do that?" Billy asked

"Yeah I can." He answered. "Have you every jacked off before
Billy?" Jack asked. So far everything was going perfect

Billy had heard the term jack off before, but he wasn't sure
what it meant, he knew it was something dirty though. "What
does that mean?"

"Well when boys look at pictures like this it makes their
dicks get hard, is your hard now Billy?"

"Yeah," Billy answered shyly

"So is mine, when you're my age and you look at stuff like
this your dick gets hard and you have to make it shoot sperm
to get it to go away. Here look" jack said pointing to the
noticeable bulge in his shorts.

Billy's eyes widened at the sight. He had never seen one
that big and hard before. Then jack pulled his short and
underpants down and his rock hard cock sprang into view.
Jacks dick was nearly 5 inches long and over an inch wide,
above average for a boy his age but to Billy it looked huge.
Jacked slowly stroked himself a few times and bead of precum
leaked out of the tip.

Let me see yours Billy

"I don't know if I should" Billy had been warned about doing
things like this.

"It's okay were both boys and we wont get into trouble if
neither of say anything"

Reluctantly Billy pulled his pants down and his little 2 «
inch stiffy popped out. Jack grabbed it between his thumb
and forefinger and stroked it up and down.

"Does that feel good?"

Billy felt like he had a million butterflies in his stomach
and croaked out a "yeah" Jack continued to masturbate Billy
until he began to squirm under him. After a couple minuets
Billy said

"I gotta pee"

"Relax its okay you won't pee"

Jack continued to masturbate the little boy as his first
orgasm approached. Billy squirmed and grabbed Jack has hand
as his little boy dick twitched in his hand. Then Billy
relaxed breathing heavy.

See Billy you had an orgasm, when you get older and that
happens sperm will come out. Did you like it?"

"Yeah"

Now that I did it for you, you should the same thing for me.

Billy though that was only fair, he did like the way it had
felt. Billy tentatively reached out and took hold of jack
dripping erection and stroked it up and down

That feel really good Billy, but I want you to take it into
you mouth like the girl did on the computer.

"I don't know" Billy said

Please Billy, it will me feel really good and I promise I'll
do it on you after."

Billy was eager to please Jack, and wanted to make him feel
good, but was unsure about putting the older boy's dick in
his mouth. "You promise it won't taste bad when you make
sperm?"

"I promise"

"You have to promise you won't tell"

I promise Billy"

"Okay, tell me what to do"

"Get on your knees in front of me and take the bottom of my
dick in your hand" Billy did as instructed  "Now open your
mouth and put it inside and close your lips over it. Be
careful not touch it with your teeth."

Billy looked at Jack's dick. It felt steely hard and yet
velvety smooth in his hand Billy could see jack had a small
amount of hair growing around the base of it like had seen
on some guys in the shower around the pool. Slowly Billy
lowered his mouth on Jack's hard young cock and closed his
pink soft lips around it. Jack let out a soft sigh as his 14
year old cock felt its first ever blow job.

"Now slide you lips up and down like you saw the girl do"

Billy did so. It didn't taste too bad so far. Jack was in
heaven as he watched the 9 year old little blond boy give
his first blowjob. Billy looked up at him and the sight of
that cute little 9 year old face with his lips wrapped
around the teens cock was the hottest thing he had ever
seen. His little mouth was so warm and wet jack was dripping
precum. Jack had never been this excited before. Jack rubbed
the boy's head and gently pushed his head down on his cock a
little further each time until the boy nose was touching
jacks sparse pubes. Jack felt the pressure build and was
moaning. Billy was amazed at how good he seemed to be making
jack feel. Even though he was gagging slightly each time he
went all the way down on jack's dick, he kept going because
he wanted to make jack feel good.

"Get ready Billy I'm going to cum in your mouth"
Jack's erection swelled as his orgasm approached. He held
his hand firmly on the back of Billy's head in case the boy
had second thoughts about letting Jack come in his mouth.
Billy looked up at jack as his he the first shot of cum
sprayed that back of the little boy's throat. Jack pushed
Billy's head down all the way as his cock swelled in the
boy's mouth. After the second shot Billy had no choice but
to start swallowing the sticky goo. Jack moaned as he shot a
third fourth and fifth volley into the little kids' virgin
mouth. Jack shuddered as a few more pulses sent the last of
his cum into the kid. After about 30 seconds he pulled the
boy off his cock and bent down and French kissed him. As his
tongue explored Billy's mouth jack could taste the remnants
of his cum. He hugged Billy tight and said

"Thank you so much that was amazing" Jack looked into
Billy's eyes and smiled. "You did a really good job and made
me feel so good." Billy smiled back at him shyly.

Then jack took Billy by the hand and led him to his bedroom.
Jack undressed the boy and lied him down on the bed on his
back. He rubbed Billy's still hard little boy dick and then
as promised he took the boys little erection into his mouth.
Jack bobbed his head up and down eliciting moans from the 9
year old. After just a few minuets he felt the boy tense as
his dick twitched in the teen's mouth. Afterward Jack hugged
and kissed Billy and lied there to cuddle with him for a
half hour before his mom got home.

"Did you like that Billy?"

"Yeah"

"Good well do it again tomorrow night." Jack said "when I
shot my cum into your mouth and you swallowed it, it was the
best feeling I've ever had. You did a good job."

"Really?"

"Yeah, and tomorrow night we can try something else too"

"What?"

"You'll see"

The next night after Gina had gone to bed, Jack made like he
was putting Billy to sleep. He slowly undressed Billy and
had him lie down on the bed and began to suck the kid. After
a couple minuets he had the kid panting and he reached into
his bag and pulled out a jar of Vaseline and smeared some
his finger.

"Tonight I'm going to fuck your ass Billy."

"Wont that hurt? Your dick is really big."

"Nah it won't hurt too bad, it will feel good after a
while."

Billy didn't say anything, he was scared about the idea of
getting his little butt fucked by Jack's big dick, but he
wanted to make Jack feel good again. Jack rubbed his lubed
finger along the boys puckered little hole and slowly
inserted it has he sucked the boy. Billy let out a soft
groan but made no move to stop him. Jack slid his finger in
and out for a minute and the inserted his thumb into the boy
ass. When he felt Billy getter ready to cum he would back
off on his sucking. When Billy got used to the thumb Jack
decided it was time

"Okay turn over on you stomach and put your head down on the
pillow, it's gunna hurt at first but you can't wake your
sister.

Jack then lubed his nearly 5 inch prick up real good and
crouched over Billy. He lined his rock hard cock up with the
boys little opening and slowly pressed it into the kid. As
the head slipped in Billy felt a sharp stab of pain and
suppressed a scream. It hurt a lot. Jack rested a moment
then continued to push his cock into the boy's virgin ass.
Billy was in a lot of pain and even though it hurt more then
a little bit like Jack had said, Billy knew Jack needed to
cum badly and Billy wanted him to be able to finish inside
him. Jack couldn't believe how good it felt as he lost his
virginity to the 9 year old little boy. He knew he was
hurting the kid and had to try his hardest not slam his dick
all the way up the kids ass. As more of his erection
disappeared up Billy's ass he started to pull beck and
fourth gently as he went deeper and deeper until he had his
whole cock inside of the boy.

"Okay Billy I'm going to start fucking you now."

With that the teen started pumping in out of the tight
little ass, slowly at first but he started to pick up speed.
Billy was still in some pain but it was subsiding. Billy
just lied there waiting fir jack to finish. He was looking
forward to see how it felt when the teen pumped his sperm up
his ass. Jack started stroking Billy's cock and Billy felt
his own little orgasm building

"Oh god your ass is so tight, I'm going to fill you up with
my cum." He whispered in the boy's ear.

"Oh god here it comes kid."

Jacks cock expanded as he started shooting into the little
boy's ass. Jack thrust one last time as he squirted inside
the boy. He pumped about five good shots into him. As jack
was cumming Billy could feel it inside him and started to
cum as well. Both their orgasms finally subsided and he
pulled out and kissed the boy on the check.

"That was wonderful Billy"

"I liked it too jack, even though it hurt at first."

Jack cleaned up Billy in the bathroom and then they cuddled
for a while until Billy fell asleep. Jack tucked him in and
waited for Julie to come home. Today is payday he thought to
him self

"Best job ever" Jack said out loud as he sighed.