Date: Tue, 3 Aug 2004 17:25:07 EDT
From: Justin0398@aol.com
Subject: Chester the Molester: Timmy's Dilemma by Justin Davis (M/t,mast,anal)

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, or encourage similar actions by others.

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: Timmy's Dilemma
By
Justin Davis


Chester Davidson, Chester the Molester, grocery list in hand, gathered
his car keys off of the kitchen counter and turned to head toward the
back of the cottage toward the garage when the doorbell rang.

"Shit!" Chester exclaimed, in a frustrated tone, and then laid the car
keys and grocery list down upon the kitchen counter and headed for the
front door.

Somewhat upset that his trip to the grocery store had been interrupted,
Chester quickly unlocked the deadbolt and pulled open the door quicker
than he normally would have causing startling the sandy-haired kid
standing on the front porch.

"Timmy! I'm surprised to see you at this hour. Shouldn't you be in
school?" Chester said.

"Nah! We got out early today, " the thirteen year old replied.

"Well, I was just headed to the grocery store. I'm afraid you'll have to
come back another time," Chester replied, sort of wishing that he gone
earlier in the day.

"Can I come in for just a minute? I need to talk to yah about
something," Timmy said in a serious tone.

From his tone of voice and the serious look on Timmy's face Chester
decided the trip to the store could wait awhile.

"Okay, come on in. But, just for a minute," Chester said, then unlocked
the screen door and stood aside so Timmy could enter.

As Chester re-locked the screen door, and then closed and looked the
front door, Timmy went to the living room and plopped himself down upon
the black leather couch in his usual spot.

"How's Tyrone? I haven't seen him since last month?" Chester asked as he
headed into the living room.

"He's okay. He's been kinda busy with some science project he's working
on," Timmy replied as Chester seated himself in his stuffed chair.

"I see. Well, what's so serious that you need to talk to me about it?"
Chester asked.

"Uh, well, I was wondering if you could loan me three hundred dollars,"
Timmy replied, in somewhat of a meek tone.

"Three hundred dollars? That's a lot of money, Timmy!" Chester replied.

"I'll pay it back. In fact I'll come over as many times as you want and
you can suck my peter and eat my hole and I won't take any money," Timmy
said, with a hopeful tone in his voice.

"Uh, well, that would take a lot of times. What do you need the money
for?" Chester asked.

"Well, there's this real neat Laker's jacket and mom says we don't have
the money and I told the guys I was gonna get it and now I can't and I
want it so bad and they're gonna know I lied and everything!" Timmy
gushed.

"I see. Well, I really make it a practice not to loan money, Timmy. I'm
sorry."

"Please. Just this once! I mean I thought you might do it since I've
sent some guys to yah and stuff. I'll pay you back. Honest!"

"I'm sorry Timmy. I do appreciate you bringing Tyrone and Billy by, but
I don't loan money.

"Please, just this once!" Timmy begged, his voice full of desperation.

"I'm sorry Timmy. I can't make an exception even for you," Chester
replied, shaking his head no.

For a moment, Timmy sat and looked at the older man.

"You can fuck me," Timmy then said, his voice so soft that Chester
couldn't hear what he said.

"Uh, I didn't hear you Timmy. What did you say?" Chester replied.

"I said, you can fuck me if you want," Timmy responded, and cast his eyes
downward toward his feet.

Chester was stunned, not that he hadn't thought about putting his big,
thick, cock in the kid's butt. However, Timmy was one of those kids that
Chester had figured would just come to get his peter sucked and his hole
eaten and that would be all he would ever do.

"Uh, what makes you think I'd want to do that?" Chester asked.

"I talked to Billy," Timmy replied meekly, looking up at Chester and then
casting his eyes back down toward his feet.

"I see. And just what did Billy tell you?" Chester asked.

"He told me that you put your dick in his butt and that you paid him two
hundred dollars," Timmy replied softly, his head cast downward at his
feet.

"Is that all he told you?" Chester asked.

"No, he told me you had a really big dick and his butt was sore for
almost a week," Timmy replied, looking up at Chester.

"Did he tell you anything else?" Chester asked.

"Uh, yeah. He said he comes by once a month and you fuck him and pay him
two hundred dollars and it doesn't hurt much anymore," Timmy replied,
looking up at Chester and then looking back down at his feet.

"I see. Well, I can tell he's told you just about everything."

"Please, Chester! I really want that jacket. I told the guys I was
getting it and everything! I know it's gonna kill me and hurt awful but
I'll let you fuck my butt twice if you'll give me the three hundred
dollars," Timmy said, his voice filled with desperation.

"Timmy, two hundred is what I usually pay for that. However, since
you've brought some guys by I'll consider paying you three hundred. By
the way it's not going to kill you. But, I want you to know what you're
getting in for if you agree to do it," Chester said, a serious tone in
his voice.

"Uh, wadda mean?" Timmy asked.

"I mean, Timmy, if I fuck your butt I'm gonna put all my dick in you and
I'm gonna fuck you with it. It's gonna hurt and your probably gonna
cry. In fact, you're probably gonna cry worse than the last time you got
spanked," Chester warned, in hopes of scaring the kid because he really
didn't want to fuck Timmy just yet since he was physically the smallest
of all the kids that came by.

"I know. Billy told me." Timmy replied his voice barely audible.

"Timmy, I want to show you something," Chester said, and rose from his
stuffed chair.

Timmy watched as Chester unbuckled his belt, pulled his slacks down, and
then pulled down his boxer shorts.

"Oh gosh!" Timmy exclaimed under his breath, seeing Chester's long,
thick, flaccid, cock that was almost eight inches in its current state.

"It gets bigger when its hard, Timmy!" Chester warned.

"Oh damn!" Timmy exclaimed softly, wondering not only how big the thing
really got but how Billy could possibly take it all up his butt.

"So, why don't we just forget about it. Okay?" Chester said.

For a moment, Timmy stared at the man's huge penis. He wanted the jacket
really bad. Did he forget about the jacket or did he take the huge cock
up his butt and get the jacket? It was a dilemma for sure.

"Oh God!" Timmy moaned, trying to decide what to do.

"Well, I really need to get to the store," Chester said, and pulled up
his boxers and proceeded to pull up his pants.

"I gotta do it. I gotta have the jacket!" Timmy said, the tone of his
voice mixed with both desperation and uncertainty.

"Timmy, it's all gonna go in your butt!" Chester warned.

"I know," Timmy replied, and cast his head downward again. "If Billy can
do it I can too," he said, looking up at Chester.

"Okay, I've got to get going to the store. Tell you what, you think
about. Think about it really really hard. If you decide you still want
to do it then come by after you get out of school tomorrow. Remember,
though, it's gonna be tough," Chester said, hoping that the kid would
decide the jacket was that important.

"Okay, I'll go."

"Fine, and you can still come by anytime you want to get your peter
sucked," Chester said, buckling his belt again.

As Chester ushered Billy out and closed and locked the front door behind,
he was certain that Timmy would think more and more about having all his
cock up his tiny butt and the subject of the jacket wouldn't come up
again.

The next day, four o'clock came, then four thirty, then five, and no
Timmy. Chester halfway smiled to himself and turned off the television
and went to the kitchen in order to begin fixing his dinner. Then, just
as he removed the package of chicken breasts from the freezer the
doorbell rang. Chester replaced the package back into the freezer,
closed the door, and headed to the front door to see who was there.

"Timmy! I thought you'd decided to forget about the jacket," Chester
said, actually surprised that the kid was standing there on the porch.

"I want the jacket!" Timmy replied.

"You sure?" Chester asked.

"Yeah, I gotta have it!" Timmy replied.

"Okay, come on in," Chester said, and unlocked the screen door and opened
it, standing aside so Timmy could enter.

Timmy entered and went over to the living room couch and plopped himself
down in the usual place and waited while Chester locked the door and
walked into the living room.

"Timmy, I really think you should forget about the jacket," Chester said,
as he seated himself in his stuffed chair.

"I gotta have it," Timmy replied, his voice whining.

"Okay, it's your decision. When's the last time you took a crap?"
Chester asked.

"Uh, yesterday," Timmy replied, wondering why the man wanted to know.

"Well, we're gonna have to clean you out then before we get started. Do
you know what an enema is?" Chester asked.

"Uh, no!" Timmy replied, having never heard the term.

"Well, it's not that big a deal. When you get your clothes off come on
back to the bathroom," Chester said, and headed for the bathroom in order
to make the preparations necessary to clean out Timmy's insides.

When he got to the bathroom, Chester retrieved the enema bag, hose, and
douche nozzle from one of the cabinets and began to fill the bag with
warm water for the bathtub faucet.

:"What's that thing?" Timmy asked, standing naked in the bathroom doorway
watching Chester.

"It's an enema bag. Now go over to the toilet and bend over it. I'm gonna
clean you out," Chester replied, and began to screw the hose onto the
bag.

Timmy did as he was told and watched as Chester smeared Vaseline all over
the douche nozzle and then came toward the toilet.

"Now, I'm gonna put the nozzle in your butt. It'll slide right in. Try
to hold the water in as long as you can. We'll probably have to do this
two or three times until you shit out clear water," Chester said, and
began to insert the nozzle into Timmy's rectum.

"Oh gosh!" Timmy exclaimed, as the nozzle slipped into his butt.

"Okay, here goes! Remember to hold it as long as you can," Chester said,
and released the clamp on the hose.

"Oh! Mmmmm!" Timmy exclaimed, as the warm water began to flow into him.

Chester watched as the bag began to slowly flatten as the water was
emptied from it and Timmy's tummy began to swell.

"Oh gosh! I gotta shit!" Timmy soon exclaimed.

"Hold on just a little longer. It's over half empty," Chester replied,
hoping the kid could get the entire contents of the enema bag in his
bowels.

"Ohhhhh! My stomach is beginning to hurt!" Timmy exclaimed, as his
stomach began to cramp.

"Hang on! Just a bit more!" Chester replied.

"Uhhhhh! Unnhhhh!" Timmy exclaimed as the cramps got more severe.

Chester noticed that Timmy's tummy was beginning to heave, and since the
contents of the enema bag were almost all gone, he closed the clamp on
the hose and removed the nozzle from Timmy's butt.

"Okay, shit it out!" Chester said.

Quickly, Timmy jumped to his feet and sat himself upon the commode.
Instantly, water began to spew from his butt into the toilet and Timmy
let out a big sigh of relief. Two more times, Chester repeated the
process, and when he was satisfied Timmy was thoroughly cleaned out, he
told him to wipe his butt and go back and get on his bed and wait.

"What's that?" Timmy asked, as Chester entered the bedroom holding a tube
of lube.

"It's for slicking up your butt and my dick. Now, get in the middle of
the bed on your hands and knees. I'm gonna put some of this in your
butt," Chester said, and began to unscrew the cap on the tube of lube.

Timmy made a small moaning sound as Chester escalated himself onto the
bed, the reality of what was about to happen setting in.

"Now, just relax. I'm gonna put my fingers in your butt and make sure
it's good and slick," Chester said, and squirted a liberal amount of the
goop onto the first two fingers of his right hand.

"Oh! Ahhh!" Timmy exclaimed as the tips of Chester's two fingers entered
his bum.

Slowly, Chester both rotated and fucked his fingers into Timmy's bottom
both to grease his hole up and loosen him up as much as possible, which
wouldn't be much since Chester had never even fucked him with his fingers
while he sucked his peter.

"Mmmmmm!" Timmy moaned, when Chester's fingers were all the way in his
behind.

When Chester was satisfied that the boy's hole was as lubed as it was
going to get, having applied more lube twice, he removed his fingers from
his hole.

"Okay, that ought to do it. You sure you wanna do this?" Chester asked.

"yesssssss!" Timmy replied meekly.

"Okay!" Chester replied, and got off of the bed to take off his bathrobe.

"Oh God!" Timmy moaned, when Chester opened his robe and he got a look at
Chester's now semi-flaccid penis, for it was already bigger than when he
had seen it totally flaccid the day before.

Chester dropped his robe to the floor and escalated himself back up onto
the bed, picked up the tube of lube, squirted some into the palm of his
right hand, and then began to slick up his cock with the stuff.

"It'll be easier if you put your head down on the bed," Chester said, as
he lubed up his hardening cock.

Timmy did as he was told and he was soon head down and butt up in the
middle of the bed, his ass crack splayed open and his pink hole totally
exposed.

"Okay, I'm gonna fuck you now! I'll go slow, we've got plenty of time,"
Chester said, and began to position himself behind Timmy's upturned butt.

Chester's words, and the movement on the bed, prompted Timmy to raise his
head up and look behind him. Instantly, he wished he hadn't. There in
all its glory, gleaming with lube, was Chester's, hard, thick,
eleven-inch cock aimed directly at his bottom.

"Ohhhh! Noooo!" Timmy whimpered, as he turned his head and lay it back
down upon the mattress.

"Okay, Try to relax. If you don't It'll make it hurt more," Chester
said, and took hold of his cock with his right hand and aimed it at
Timmy's pink hole.

"Ohhhhhh!" Timmy exclaimed, when he felt the plum-sized head of Chester's
cock kiss his ass lips.

Then, as he felt the pressure build, Timmy began to whimper loudly.

"Ohhhhh! Ouch!" Timmy wailed, as his ass lips began to part in order to
accommodate the huge cock head.

"Don't fight it, Timmy! Try to relax! Pretend like you're on the toilet
shitting out the water again.

Whimpering loudly, Timmy did as he was told. Slowly, his ass lips opened
up wider and wider and there was almost no pain at all. Then, the head
of Chester's cock popped into his butt.

Instantly, it felt as if the biggest turd in the world was in his butt,
trying to go the opposite direction, and Timmy made a huge gasp for air
and grabbed hold of the bed sheets with his hands.

"Owwwwww! Owwwwww! Stop! Stop!" Timmy wailed, then started to cry.

Chester removed the head of his cock from Timmy's bum, prompting him to
gasp at the sudden emptiness. Then, he began to work his fingers into
Timmy's hole, again prompting Timmy to gasp and whimper more than cry.

"Okay, Timmy. I'm gonna do this for awhile to loosen you up some more,"
Chester said, and began to fuck his two fingers in and out of Timmy's
butt.

From years of experience, Chester knew that a kid as physically small as
Timmy, and as scared, was going to have a tough time taking his monster
cock in his tiny behind. However, Chester also knew that if he could
loosen Timmy up enough so that he was getting fucked with three fingers
he could slip the head of his cock in before Timmy almost even knew it
was there.

"Unh! Uh! Ow!" Timmy exclaimed as Chester began to add the third finger.

"Just relax, Timmy. Relax! You're doing fine!" Chester said, and patted
his bottom gently.

Slowly, Chester rotated his fingers around in Timmy's butt, and after a
few minutes, he had all three fingers in the boy's bottom up to the
knuckles and he fucked him with the awhile. Then, satisfied that the
head of his cock would now go in much easier, he grabbed hold of his hard
pole, guided it toward Timmy's hole, then quickly replaced his fingers
with the head of his cock.

"Uhhhh! Ahhhhhh! Ow!" Timmy exclaimed, then whimpered.

"It's okay. I'm in you now. Just try to relax and tell me when it
doesn't hurt. There's no hurry," Chester said, the boy's ass muscles
strangling the head of his cock so tightly that it hurt.

For several minutes, Chester held still in order to let Timmy adjust and
slowly Timmy's ass muscles began to relax so they weren't squeezing the
head of Chester's cock to death.

"It still hurt?" Chester eventually asked.

"Some, but not really bad!" Timmy replied, his voice quivering.

"Okay, I'm gonna put more in your butt. Tell me when you want me to
stop," Chester said, and pushed his hips forward slowly.

"Oh shit! It hurts! It hurts! Stop! Stop!" Timmy wailed, grabbing the
sheets again and panting.

"It's okay. You're doing fine. I got about three inches in your butt
now. Just let me know when you're ready," Chester replied, holding
perfectly still.

It took almost ten minutes more for Chester to get over half of his cock
into Timmy's behind, having to stop frequently to let the young teen get
used to the massive tube.

"Okay, I'm gonna start fucking the rest of it in you. It's already over
half in," Chester said, grabbing hold of Timmy's hips when Timmy told him
he was ready again.

Slowly, Chester began making small, slow, strokes in and out of Timmy's
butt, slowly putting more and more of his cock into his rectum.

"Oh! Unh! Arrgggggh! Unh!" Timmy wailed as the cock went deeper into his
behind.

Then, all resistance seemed to disappear and Chester was in balls deep.

"You did it, Timmy! I'm all in you Timmy! Look!" Chester said, as his
pubes began to brush Timmy's bottom.

Whimpering somewhat less, because the pain was considerably reduced, but
still feeling terribly full inside, Timmy raised his head and looked back
toward his butt.

"Oh God! The whole thing!" Timmy moaned in disbelief.

The sight of the long, gleaming, tool completely disappearing and
reappearing between his tiny buns was just too much, and Timmy whimpered
loudly again and lay his head back down upon the mattress.

"Okay, I'm gonna wank your peter! It'll make it feel better!" Chester
said, and reached under Timmy and grabbed hold of his peter and began to
twirl the head in his fingers and jack it.

"Oh Shit! ! Unh! Unh!" Timmy exclaimed, and grabbed the bed sheets for
all he was worth as Chester began to long-dick him.

For some time, Chester fucked Timmy on all fours, Timmy alternately
moaning and whimpering, until Timmy's butt began to loosen up enough so
that his cock slid in out with ease, although it was still very tight.
Then, Chester removed his cock, quickly flipped Timmy over on his back,
tucked his legs over his arms in order to raise his butt up a bit, then
swiftly put his cock back in balls deep.

"Ohhhhhh! Arrrrrrrrghhhh!" Timmy hollered, then bit his lower lip and
furrowed his brow as the thick monster cock rushed back into his insides.

"Okay kid, here's where you earn the jacket. I'm gonna fuck you so hard
you cute thing!" Chester said.

Timmy saw the look in the man's eyes and squealed and almost
involuntarily threw his hands around the man's neck as if to grab for
safety. Soon, the bedroom was full of the sounds of Chester's groin
smacking into Timmy's upturned butt and Timmy's grunts and whimpers. As
the pace of the sodomy increased, Timmy's legs began to bounce up and
down in time to the thrusts into his bottom.

After a bit, Chester again removed his cock from Timmy's butt, grabbed
hold of the kid's legs and bent them back to his ears, elevating his butt
as much as possible so that his cock would rub against Timmy's tiny
prostate with every stroke. Then, he again rapidly entered Timmy balls
deep. In response, Timmy yelped loudly, not only because of the sudden
rush of fullness but also because of the electric tingles that shot
through his body as the huge head of Chester's cock poked at and slid
across his tiny prostate.

"Uh---Uh---Argggggghh---Argggggh--Uh--Uh!" Timmy wailed, as Chester began
to fuck him so hard that the man's groin smacked loudly against his tiny
butt cheeks and his whole body shook with every stroke into his behind.

Then, somewhere just inside Timmy's butt, the electric shocks began to
grow and grow in intensity and take over his entire body until they
welled up so much Timmy thought he would die.

"Ohhhhhhhhhhhhhhhh!" Timmy eventually exclaimed in a crescendo, his eyes
flying open wide in disbelief.

Then, his eyes rolled back into his head and he squealed loudly, like a
little girl, and began to shoot cum pellets all over his tummy, while his
whole tiny body quivered and his toes curled to the breaking point, from
the intensity of his first "hands free" orgasm.

"Oh fuck!" Chester hollered, as the kid's anal spasms started milking his
cock.

Needless to say, Chester had hoped to have a much longer fuck for three
hundred dollars. However, the tightness of the kid's ass, which was
already about to make him pop his load anyway, coupled with the anal
spasms, were just too much.

"Ohhhh--Shittttt---Yeah!" Chester hollered, and blew his load into
Timmy's rectum, causing Timmy to grunt, then moan, as the warm blast
flooded his insides.

"Oh my butt hurts!" Timmy said later, after it was all over and he was
probing at his dilated and leaking hole with his fingers.

"It'll be okay in a few days. You did great!" Chester said, and pulled
the kid to him and kissed him on the forehead.

"Do I get the jacket?" Timmy asked.

"Sure! Uh, you wouldn't want two jackets would you?" Chester asked.

"No way! " Timmy exclaimed, prompting Chester to burst out laughing in
response, and Timmy to quickly think of how good that two hundred-dollar
pair of tennis shoes he wanted would look with his new jacket.

Indeed, both the jacket and tennis shoes did look good on Timmy and he
was really proud that he had earned both, although at the expense of a
VERY sore hole.

The End