Date: Mon, 26 Jul 2004 09:41:10 EDT
From: Justin0398@aol.com
Subject: Chester the Molester: Billy 02 by Justin Davis (M/t,mast,oral, anal)

The following story contains graphic sexual scenes between a young male
and an older male. If material of this nature offends you then you should
not read this story. Additionally, if you are under 18 years of age in
most states you are not allowed to read this story by law.

This story is purely a work of fiction. Any resemblance to person's
living or dead, or to events that may have occurred, is purely
coincidental. Additionally, the actions of the characters in this story
are in no way intended to show approval of, or give sanction to, their
actions.

The author claims all copyrights to this story and no duplication or
publication of this story is allowed, except by the web sites to which it
has been posted, without the consent of the author.

Positive comments are always welcome and you may e-mail them to
Justin0398@aol.com

Chester the Molester the Next Generation: Billy
By
Justin Davis

Chapter Two


Sure enough, at four o'clock the next afternoon Billy showed up at the
front door of Chester's cottage and was guickly ushered in where he
plopped himself down on his usual position upon the couch.

"So, you need two hundred dollars for a new bike?" Chester asked, as he
sat down in his stuffed chair.

"Uh yeah. Can I suck yah four days in a row?" Billy asked.

"Well, like I said yesterday it's too soon for that. However, there is a
way you can earn the rest of the money you need for the bike," Chester
replied, and smiled.

"How?"

"Well, it's going to be a pretty tough thing and it's gonna hurt some at
first. You might not want to even try."

"Try what?"

"Tell you what. Come back in a week and you can earn another fifty."

"No! I need the money this week. What do I need to do?"

"Well, you're going to have to sit on my cock and then I'm going to fuck
you with it," Chester replied, and smiled.

"Fuck no! No way! It's too big! You'll kill me!" Billy exclaimed.

"I can assure you it won't kill you. Other boys have survived the
experience. In fact, Jacob comes by once a month and earns two hundred
dollars," Chester replied, and smiled again.

"Jacob sits on your dick?" Billy exclaimed.

"Yep! Every month for two hundred dollars."

"Uh, who else?" Billy asked.

"Oh, a couple of older boys you wouldn't know. They come by once a
month, too."

"Uh, it's gonna hurt too much!"

"Some, at first. You can quit when you want, then try again."

"I done it before, you know," Billy said, and cast his eyes downward.

"Done what?" Chester asked.

"Had a dick in my butt."

"You have! Whose?"

"Uh, my cousin David. He's seventeen now."

"So, how old were you?"

"I was ten."

"And David?"

"He was fourteen, I think."

"Did you enjoy it?

"No! It hurt! He had me get down on my hands and knees and he told me
the same thing like you just did about stopping and he didn't. He put it
in my butt and just kept puttin in more and started fucking me and I was
crying!" Billy said, casting his eyes downward again.

"That was wrong of him to do that. Did he cum in your butt?"

"Yeah!"

"Well, I'm sorry you had that bad experience, Billy. Let's just forget
about what I said earlier."

"No! No! I gotta have the money for the bike. I put it in layaway and if
I don't get it out this week they are gonna put it back!" Billy wailed.

"Really, I think we should just forget about it."

"Please! Let me try!"

"Billy, are you sure?

"Yeah!"

"Okay, take off your clothes while I get things ready," Chester said, and
got up from his stuffed chair.

As Billy began to disrobe, Chester went to the kitchen where he got one
of the chairs from the breakfast table and brought it into the living
room and sat it in the middle of the carpeted floor.

"What's that for?" Billy asked, removing his last article of clothing
which were his boxers.

"We're gonna need this later," Chester replied. "Now come with me,"
Chester added, held out his hand for Billy to take hold of.

As the headed toward the bathroom Billy wondered why they were going
there. However, he soon found out.

"Okay, get down on your hands and knees and lean over the toilet. I need
to clean you out a bit," Chester said.

Billy did as he was told and watched as Chester filled the red enema bag
with water then connected the hose and greased up the white douche nozzle
with Vaseline.

"Okay, this is gonna feel a little funny when it goes in your butt. Try
as hard as you can to hold it all in until I tell you it's okay to sit on
the pot," Chester said.

"Uh!" Billy exclaimed as Chester inserted the nozzle into his butt. "Oh
gosh! He then exclaimed as Chester released the clamp on the hose and the
warm water began to flow in him.

"That's fine. You're doing fine," Chester said, noticing that Billy's
tummy was beginning to swell just a little.

"Oh, I'm so full. I gotta go! I can't wait!" Billy exclaimed.

Quickly, Billy jumped up, the nozzle popping out of his rectum as he did
so, and seated himself upon the toilet. Instantly, the bathroom was
filled with the sounds of water gushing into the toilet from Billy's
bowels.

"Not again!" Billy exclaimed, and Chester began to refill the bag.

"Yeah, only got about half of it that time. We gotta do it until the
water is clear when you shit it out," Chester replied, and re-attached
the hose to the enema bottle.

The second time, even though he moaned a lot, Billy managed to get the
entire contents of the bag in him before he hopped up and set on the pot
and let go. Then he moaned loudly again as Chester told him they needed
to do it one more time. The third time was enough and eventually Billy
had spewed out all the water.

"Wipe your butt and come back into the living room and sit on the couch.
I need to put some stuff in your butt," Chester said, and headed for the
living room.

Once there, Chester went over to one of the lamp tables opened the drawer
and retrieved the tube of lube he always kept there.

"What's that for?" Billy asked as he re-entered the living room.

"It's some stuff to grease up your butt and my dick. Go sit on the
couch," Chester said.

Billy sat upon the couch and watched the man as he opened up his terry
cloth bathrobe, revealing his huge flaccid cock, and walked toward where
he was seated upon the couch.

"Okay, I'm gonna put some of this stuff in your butt and then on my
dick. You remember when I ate your hole on the couch that time?" Chester
asked.

"Uh huh!"

"Okay, spread your legs back like that," Chester said, and began to
remove the cap from the tube of lube.

Billy grabbed hold of his legs and pulled them back toward his chest so
that his butt hole was exposed and watched as Chester squirted a liberal
amount of the stuff on two of his fingers.

"Now just relax," Chester said, as he knelt down and moved his fingers
toward Billy's exposed hole.

"Uh! Oh gosh!" Billy exclaimed, as Chester began to slowly work his
lubed fingers into his butt.

"Just relax, Billy! Relax!" Chester said, his two fingers in the boy's
bum up to the first knuckle.

"Oh! Uh! Billy exclaimed, as the fingers of the older man slid into his
butt all the way.

Chester began to slowly fuck Billy's hole with his fingers making sure it
was well lubed while Billy moaned.

"There, that should do it!" Chester said, as he removed his fingers from
Billy's butt and rose up off of his knees.

"Can't you just fuck me with your fingers? That didn't feel that bad!"
Billy said, looking up at the man.

"Not for two hundred dollars," Chester replied, and squirted some more of
the lube on his fingers.

Billy lowered his legs and watched as the older man began to lube up his
now semi-flaccid cock with the lube and got butterflies in his stomach as
the thing began to grow and lengthen. Then, when it was at its full
eleven inches and jutting out from the man's body like a giant torpedo,
he thought about all that in his butt and emitted a low groan.

"Okay, Billy. Here's the drill," Chester said, laying down the tube of
lube. "I'm gonna sit in that chair over there. You climb up in my lap
and put your feet on my legs. I'll tell you what to do next," Chester
said, and walked over toward the chair and sat down. "You still sure you
wanna do this?" Chester then asked.

"Uh, I guess so," Billy replied, a little less eager as he looked at the
gleaming monster cock.

"Okay, come get up here," Chester replied, patting his thighs.

Slowly, like he was being led to the execution table, Billy's feet
plodded toward the man sitting in the chair, his huge cock gleaming with
lube and his lime sized balls hanging low and resting upon the seat of
the chair. Once there, Billy climbed up into the man's lap, his feet
resting upon the older man's thighs.

"Okay, now raise your butt up and grab hold of my dick. You're gonna put
it in your butt yourself. Remember you stop whenever you want. We can
try again tomorrow."

"Uh, okay," Billy replied, a slight tremble in his voice.

Billy did as he was told and grabbed hold of the man's massive meat and
raised his butt up. Then he guided the head toward his hole.

"Oh gee! It feels so big!" Billy exclaimed, as he felt the plum-sized
head kiss his hole.

"Take your time!" Chester warned.

Slowly, and carefully, Billy lowered his butt and bit his lower lip as
the pressure on his hole intensified.

"Oh shit! Ow!" Billy exclaimed, as half of the head lodged itself in his
anus.

"Your too tense. Relax. Take you're time."

"Oh! Uh! It's starting to hurt!" Billy exclaimed, as the pressure of the
head to penetrate his anus all the way increased.

"Relax! Here let me help," Chester said, and reached for Billy's peter
with his hand and began to twirl his fingers over the head and jerk on
it.

Instantly, Billy's mind was split between the gooey feelings in his
peter, which was instantly beginning to harden, and the pain in his butt
that was now considerably reduced by the gooey feelings. As a result,
his anus opened up and the plum-sized head of the monster cock popped
into his rectum.

"Oh fuck! Ow! Ow!" Billy wailed, and raised himself up off of the huge
tool.

"It's okay. Try it again. You did fine," Chester said reassuringly, and
began to wank Billy's now hard peter for him again.

Again, Billy raised his butt up and guided the huge cock toward his
hole. This time his brow furrowed as the head slid more easily into his
anus and he only gasped a little as the head popped into his rectum.

"Okay, I'm in you. Now, take a much time as you need and stop when you
want."

Biting his lower lip again, and with furrowed brow and eyes closed, Billy
nodded his head that he understood.

For a little more than a minute, Billy hovered with just the head of the
huge tool in his butt. Then he moaned, as the gooey feelings in his cock
got stronger, and lowered his butt just a little bit more.

"Ahhhhhh! Ow!" Billy exclaimed, as two inches of the thing slid into him
stretching his rectum to accommodate the width.

For awhile, Billy remained motionless, his legs beginning to tremble a
bit. Then, he lowered his butt a bit more at about the same moment a
huge wave of gooey feelings traveled from his peter down to his toes.

"Oh fuck! OWWWWWWWWW!" Billy shrieked, and leaned his head upon
Chester's chest.

Billy sat motionless for awhile, panting loudly, for almost half of the
huge monster was now inside him.

"I can't! I can't! I can't do anymore! It's too big!" Billy panted,
shaking his head from side to side.

"It's okay. We can stop now. Let's try again tomorrow," Chester said,
letting go of Billy's still hard penis.

"Wait! Just give me a second," Billy panted.

Chester couldn't believe the kid was still gonna try to take more. He
had to be hurting a lot.

"Wank me again!" Billy panted.

Chester reached for Billy's hard, four-inch, peter and began to jerk him
off again.

"Mmmmmmm!" Billy moaned, as the gooey feelings came back, considerably
overriding the pain in his butt.

Billy tried to lower his butt some more on the huge pole and again he
cried out in pain. Chester noticed tears were beginning to form in the
boy's eyes and he decided to call a halt to it all.

"That's enough, Billy. We're gonna stop right now!" Chester said, and
reached for the boy's waist to pull the boy off of him.

"No! No! Don't!" Billy hollered in a panicked voice.

What happened, then, Chester had never seen before, and he doubted if he
would ever see again.

In a panic, Billy quickly moved his feet off of Chester's thighs and
emitted a loud squeal. There was no where for Billy's legs to go but to
dangle over the side of Chester's legs. Instantly, Billy lost all of the
support his feet had given him and the remaining half of the huge cock
slid into slid rapidly all the way into his rectum, his butt crashing
down upon the grown man's pubes.

Billy was now impaled on the huge sausage and immediately a gurgling
sound came from his wide-open mouth. Then, a piercing scream filled the
room as Billy collapsed on the man's chest and began to sob. Quickly,
Chester grabbed Billy's waist again in an attempt to pull him off of him.

"No! Don't move me! It's in me! I did it! Oh God it hurts bad!" Billy
sobbed.

For five minutes Chester held onto Billy. Slowly, the young teen's sobs
turned to sniffles as his butt adjusted to the intrusion of the huge
penis. In spite of the fact that Billy's tight rectum felt so good
Chester could have shot his load with only a couple of hunches up into
the kid's butt, Chester remained motionless and waited.

"You okay now?" Chester asked, running his hand through the kid's hair.

"Yeah, kinda. It don't hurt as much as it did," Billy replied and
sniffed, his head still lying upon the man's chest.

"You're one heck of a kid, Billy. No one's been able to do that the
first time," Chester replied, and patted the boy's head and then began to
stroke the nape of his neck again.

For another few minutes the two set still. Then, Billy wiggled his butt
a little.

"Mmmmm!" Billy moaned softly.

Chester continued to stroke the boy's neck and couldn't help but smile.
Instinctively, the kid was figuring out how to ride the huge piece of
meat that was up his butt. Then, Chester's face broke into a huge grin
as Billy reached for his own penis and began wank it and slowly rock his
butt in a steady motion, moaning softly all the time.

As Chester succumbed to the wonderful sensations Billy's ass was giving
to his cock, he instantly hoped that his investment account would
continue its rapid growth. The kid was a natural, and Chester had a
hunch, that when Billy's butt stopped being sore he was going to be back
for many more two hundred dollar payments.

Chester certainly hoped so, and he groaned loudly as he took hold of
Billy's hips and began to fuck his huge stalk up into Billy's rectum
while Billy rocked his butt back and forth and wanked his own peter.

Billy whimpered loudly for a bit as Chester began to fuck him and the
giant tool slithered back and forth along the walls of his insides.
Then, he began to coo. As for Chester, he was in all the heaven that two
hundred dollars could buy.

The End