Date: Wed, 1 Sep 2004 07:31:16 EDT
From: Justin0398@aol.com
Subject: Chester the Molester: Tyrone Goes Anal by Justin Davis (M/t,mast,oral)

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 Second Generation: Tyrone Goes Anal
By
Justin Davis

Chester Davidson, "Chester the Molester," went about his business as
usual on Tuesday afternoon. On Tuesdays, he usually devoted his time to
browsing the Internet in search of some new pictures to add to his
collection. It was just when he had come upon a collection of pictures of
young boys engaged in an orgy that the phone rang, knocking him off line.

"Fucking damn!" Chester exclaimed, having tried three times to connect to
the web site, and having finally having connected, being knocked off
line.

Chester was pissed at himself that he had forgotten to disable the
call-waiting feature on his phone so he wasn't in a pleasant mood when he
picked up the handset to the phone.

"Hello!" Chester said loudly, in a gruff tone.

"Uh, sir. This is Tyrone. Did I call at a bad time?" the young African
American genius with the beautiful mocha-colored skin asked.

"Ty! It's good to hear from you. It's been weeks. I suppose you've been
busy with that little item I gave you," Chester said, and grinned,
wondering if Ty had worn the batteries out yet on the anal stimulator.

"Uh, yes, occasionally. However, my parents insisted that I take the PSAT
early and I had to study for that and all. It seems they are going to
jump me to the 12th grade next Fall. I will so miss what friends I have
in 9th grade.

"Yes, I can see how you would. Yet, that is a good thing for a boy as
bright as you are, Ty. You should do well!" Chester replied.

"Yes, I imagine I will. However, that is not what I called you about,
sir." Tyrone replied.

"I see. Then how can I help you?" Chester asked, wondering what Tyrone
had on his mind.

"Well, sir, the anal stimulator has been very much fun and I have had the
best of orgasmic sensations. However, I have been researching on the
Internet and I understand that males actually copulate anally and achieve
the same results," Ty responded, a questionable tone in his voice.

"Yes, it does happen. But, not that often."

"So, it is possible then, during anal intercourse, that one might
actually have an orgasm without even touching one's self? Ty asked.

"Yes. It does happen."

"I see, sir."

"Ty, don't call me sir."

"I'm sorry. I see, Chester."

"That's better."

"So, if I would endeavor to experiment in such areas would you be willing
to oblige my somewhat deviate inclinations?"

"What!  For fucking sakes, Ty, talk where I can understand what the fuck
you are saying!" Chester exclaimed.

"I wan you to fuck my black az!" Tyrone replied, prompting Chester to
burst out laughing as he had done times before when the kid just seemed
to shift gears into ghetto lingo.

"Okay, how much do you wanna earn?"

"Earn? Well, nothing of course. I assume, since it would be a tutorial
role, that I would be paying you," Ty responded, prompting Chester to
roar with laughter. In all the years, it was the only time someone had
offered to pay him.

"Tell you what, Ty. Come over and we'll talk about it."

"Fine, that should be fair."

"When can you come over?"

"In the next fifteen minutes."

"Fine, I'll be waiting."

Chester hung up the handset to the phone and the shut down his computer.
As he got up from the computer desk, Chester closed his terry cloth
bathrobe and tied the sash. As he did so, he wondered what Ty's reaction
would be when he saw his cock for the first time. Naturally, Chester
couldn't help but chuckle to himself when he thought about how quickly Ty
would change his mind about anal intercourse once he laid eyes on the
eleven-inch monster cock.

Sure enough, within the next half-hour the front doorbell rang and
Chester went to the front door, unlocked the deadbolt lock, and opened
the door.

"Ty, nice to see you again! Come in! Come in!" Chester said as he
unlocked the screen door and stood aside so that Ty could enter.

As he had twice before, the lanky, mocha-colored, fourteen-year-old
entered the cottage and promptly plopped himself down upon the leather
couch in the living room and waited.

"Well, Ty, I must say it's highly unusual for a boy to call me and
suggest what you are suggesting. Oh, I do have a few every now and then
who earn two hundred dollars on a regular basis by letting me fuck them,"
Chester said, as he entered the living room then seated himself in his
stuffed chair.

"Well, sir, I do admit I do have reservations about it," Ty responded,
and shifted his position on the couch a bit.

"Surely, there is someone your own age you could experiment with, and
quit calling me sir!" Chester replied, trying to dissuade the boy.

"Yes, Chester, I thought about that. However, one doesn't learn calculus
from a third grader. One goes to someone with experience that can teach
him or her. I figure if I am going to have my curiosity satisfied I might
as well go to an expert," Ty responded.

"I see," Chester replied. "Have you given any serious thought about the
fact that it might hurt?" he then asked.

"Uh, yes. I did assume that that would be a possibility. However, I can
work the anal stimulator you gave me in and out of my rectum with ease
now. I figure that any discomfort would be considerably reduced because
of that fact." Ty replied.

"Well, maybe and maybe not. Let me show you something, Ty," Chester said,
and rose from his chair, undid the sash from his robe, and then opened
the robe up wide.

Naturally, Ty's eyes widened and his mouth hung open slightly at the
sight of Chester's impressive, flaccid, cock and his huge lemon sized
balls.

"Uh, you certainly have huge genitalia.  I hadn't assumed that would be
the case," Ty eventually said.

"Well, as you can see. Your curiosity might not be satisfied with as much
ease as you had hoped," Chester said, closing his robe, then re-tying the
sash and sitting back down in his stuffed chair.

"Yes, you are quite right."

"So, now you understand why I suggested someone your own age?"

"Yes, I do understand and appreciate your concern. However, if I am
indeed going to experience anal copulation I must accept the fact that
there will be some unpleasantness the first time. Naturally, I had
assumed there would be a little discomfort. Now, however, I'm confronted
with the fact that there will most certainly be more discomfort than I
had planned on," Ty responded, an air of uncertainty in his voice.

"Good! I'm glad to see you've changed your mind," Chester responded,
relieved that the boy had backed out.

"Oh, I haven't changed my mind. It will just be more than what I had
expected, much like the time I signed up for geometry the summer I was
eleven. However, I made an "A" by working hard. I will just have to take
what comes as you put that huge penis of yours in my rectum."

"Ty, I really don't think you should consider it. It's going to hurt and
you are going to cry, all the boys do the first few times. Of course,
they get paid for it. You can't be serious about going through all that
just because you're curious," Chester replied.

"Indeed, sir, I want you to put it all in my rectum."

"If I do, I'm going to fuck you very long and very hard. You will beg me
to stop but I won't. Your hole will be sore for a week afterward."
Chester warned, hoping to scare the boy.

Chester's words prompted a small gulp from Ty.

"I still want to do it," Ty said, his voice more certain than it had
been.

"Very well, We'll need to clean you out first," Chester said, and rose
from his chair.

"Uh, that won't be necessary, sir. I gave myself a warm water enema
before I called you," Ty replied.

"I see. That's a bit unusual isn't it?" Chester replied.

"I always do that before I use the anal stimulator you gave me to keep
things sanitary. Therefore, I assumed the same would be necessary if you
were going to put your penis into my rectum," Ty responded.

"Well, I guess there's nothing to do but get on with it, then. Follow me
to the bedroom and get naked and get up on the middle of my bed on all
fours," Chester replied.

Ty followed Chester to the master bedroom and did as he had been
instructed to do. Soon, he was naked in the middle of the king sized and
he made a small, almost inaudible, groan when Chester took off his
bathrobe and he saw the huge flaccid tube again.

Once he had removed his bathrobe, Chester opened the drawer of the
nightstand by the bed and retrieved the tube of lube and then escalated
himself onto the bed and positioned his body so that he was behind Ty.

"Okay, I'm gonna lube up your butt now and then my cock," Chester said,
and popped open the cap on the tube of lube.

"Oh!" Ty soon exclaimed, as Chester's fingers began to lube up his hole.

Chester inserted two fingers into Ty's hole, eliciting a small grunt from
the teen, then worked them in, out, and around just inside the boy's
rectum.  Then, he inserted a third finger, causing Ty to yelp a bit.
Finally, once Chester was satisfied that Ty's hole was as lubed as well
as he could get it, he squirted a liberal amount of the lube into the
palm of his hand and began to work it all over his hardening cock as Ty
turned his head and looked on.

"Oh my!" It is certainly getting much bigger than I expected," the young
genius replied, as Chester's cock began to grow and lengthen.

"Yes, and it's all going in your butt. You can still back out," Chester
warned.

"I know. But, sir, if I do I will regret it. I want the experience," Ty
responded, his eyes widening again as Chester took his hand off of his
now hard, slicked up, two and one half inch wide, eleven-inch long, cock.

"Okay, you want the experience you're gonna get it. Roll over on your
back," Chester instructed.

Ty rolled over onto his back and Chester repositioned himself upon the
bed, his massive missile wagging from side to side as he did so.

"I'm gonna grab hold of your legs and pull um back like I did when I ate
your hole," Chester said.

Chester grabbed hold of Ty's legs and bent them backward totally opening
up the teen's butt crack and exposing his virgin hole.  As he did so, Ty
gulped and swallowed hard as he looked down between his legs at the wide
head of Chester's cock and the huge balls that dangled beneath the
massive tube.

"I'm gonna fuck you this way so you can see it all go in your butt. You
wanted the experience kiddo well you're gonna be able to watch it all.
So, get ready. I'm gonna fuck you now!" Chester said, grabbing hold of
his cock and maneuvering into position so that the massive head was just
an inch from Ty's virgin pucker.

"Oh! Ahhh! Ty exclaimed, as he saw the massive missile move forward and
he felt the huge head kiss his virgin pucker.

Chester moved his hips forward and immediately pressure began to be
exerted on Ty's anus as the head of Chester's cock tried to spread it
wide enough to gain entry to the boy's rectum.

"Ahhhh! Oh sir! I never knew it would feel like my anus was expanding
this way. I will try not to cry but it is beginning to hurt worse than I
thought!" Ty exclaimed, laying his head back upon the pillow, then
whimpering.

"Relax! Let it in! Relax damn it!" Chester replied and continued to push.

"I'm trying! Ahhhh! Ow!" Tyrone exclaimed.

From past experience, Chester knew the only thing to do was pop the head
into the boy's butt and let him adjust to it.  So, he pushed forward very
hard and Ty's anus yielded.

"Ow---Ow---Oh God---Ow!" Ty wailed, once the huge head popped into his
butt.

"I'm in you now," Chester said, and waited a few moments for Ty's butt to
adjust to the intrusion.

"Yes, I know. There is more discomfort than I thought there would be," Ty
whimpered in response, then panted as he looked downward between his legs
and confirmed what his butt hole felt.  Indeed, some of the massive tube
was in his butt.

"Okay, I'm going to slowly fuck it all into you now," Chester warned, and
pulled back a little and started making small thrusts into Ty's butt with
his cock.

"Ow---Uhhhh---Ow---Ow! It's more than I thought! Ouch---Ow!" Ty began to
wail, and threw his head back upon the pillow as Chester began to slowly
fuck him.

Needless to say, any intellectual thoughts Ty may have had, or comments
he might have wanted to make, went by the wayside as the massive tube
began its unrelenting journey into his insides.  As a result, the bedroom
walls echoed with his grunts and cries of desperation as more and more of
Chester's huge sausage disappeared inch by inch into this rectum.

Somewhere, at about the point when about half of Chester's massive meat
was in him, and Chester began to long-dick him, Ty lost it and began to
emit a continuous sound halfway between whimpering and crying.

"Oh please! I'm full! No more!" Ty whimpered, as he raised his head from
the pillow and saw half of the slick, thick, tube working its way in and
out of his rectum.

"No way baby! You wanted the experience you're gonna have it. It's all
going up your butt!" Chester said, and shoved even more inches into Ty's
rectum.

In response, Ty threw his head back, squealed, and grabbed the sheets
with his hands. If he could have, he would have given a verbal discourse
on what it felt like to have a giant Anaconda writhe into your intestines
destined for what seemed like your stomach. Yet, all he could do was
whimper and babble incoherent gibberish.

To Ty, it was as if the massive cock was possessing his entire insides.
Seemingly, there were miles of endless cock that just kept trying to go
deeper and deeper into him.  Frightened, he screamed, afraid that the
huge tube would rupture his insides. Then, he began to sob, like many
boys had done before him, as the thick, massive, sausage went deeper and
deeper into him as if it were trying to possess his very soul.

"I'm all in you!" Chester said, as his balls began to bump Ty's butt
cheeks.

"Oh God! Uhhhhh! Noooo!" Ty whimpered and then continued to sob, this
time with relief that the thing was all in him and there would be no
more.

"Look at it Ty!  Look at it!" Chester exclaimed.

"Oh no---Uh---Ow---Oh my God---Ow! Ty exclaimed as he raised his head
from the pillow and briefly watched as the entire massive piece of meat
disappeared into him and re-appeared again, all slick with lube and his
ass juices.

Then, Ty groaned loudly and lay his head back up the pillow and
whimpered, for he could swear he felt the head of the thing sliding back
and forth underneath his navel as Chester slowly fucked him.

Content that Ty was loosened up enough for the real fuck, Chester grabbed
Ty's ankles and pushed his legs backward toward his ears so that his ass
was high in the air.  Then, he really began to fuck the boy's butt.

In response, Ty yelped, and then cried out as his body was wracked with
the first of what would be one anal shock wave after another as the head
of Chester's cock began to pound his prostate without mercy.

"Arrrrrghh---Yes---Arrrggghhh---Uh---Yes!" Ty screamed at the top of his
lungs and began to flail his arms up and down on the bed sheets.

Immediately, Chester realized that that was the feeling the boy had been
looking for all along, and in response, began to pile drive him as hard
as he could. Needless to say, Ty lost his mind.

"This is what you wanted isn't it?" Chester grunted, as he pounded away.

"Uh---Oh---Yes---Argggghh---Argggghh---Uh!" Ty chanted loudly, as
Chester's groin slammed into his butt cheeks and his teen cock began to
inflate.

"How about this? You like this?" Chester asked, as he began to pound his
groin into Ty's butt cheeks so hard that the teen's entire body shook
with each thrust.

"Arrrrrgggggh-Arrrrrrrggggghh--- Yes---Ow---Ow!" Ty wailed, his cock now
rock hard and bobbing up and down with Chester's every thrust into his
bottom.

For some minutes the fierce pounding continued. Then, Ty gasped loudly
and his eyes flew open wide in disbelief.

"Oh my God! I'm gonna cum! " Ty cried out.

Then, the young teen screamed and grabbed the sheets with all his might,
his toes curling almost to the point of breaking as he cock began to
quake and spew his white goo all over his mocha- colored upper chest and
face.

As Ty blew his load, Chester yelped loudly, for never in his life had any
boy's anal muscles contracted and milked his dick so hard when they had
had an orgasm.  Needless to say, Chester rapidly went over the top.

"Oh yeah! Fuck yeah!" Chester hollered, as he began to spew his hot load
of sperm all over Ty's insides.

Later, after it was all over and Chester was showing Ty to the front
door, he secretly hoped the boy would return. It had been one of the
greatest fucks he had had in a long time.

"I must say, sir, that my rear end is quite sore and I feel all open down
there," Ty said, as Chester opened the front door to let him out.

"Well, in a few days it will be back to normal," Chester responded.

"Indeed, I should hope so. Would it be proper for me to arrange another
session with you at this time or shall I just call?" Ty asked.

"You're interested in coming back?" Chester asked, somewhat astounded.

"Oh yes! Indeed, I believe it will be extremely pleasant to earn two
hundred dollars and have such unusual and strong sensations at the same
time," Ty remarked, then smiled.

In response, Chester just burst out laughing.

"Just give me a call, Ty. Anytime will be fine," Chester replied shaking
his head.

As Chester watched the boy walk down the front sidewalk and head toward
home, he noticed that Ty's gait seemed noticeably different and he also
noticed the lad adjust the seat of his shorts several times. Then,
Chester chuckled a bit, closed the door, and wondered how soon Ty would
change into a fresh pair of underwear after he arrived at home, since,
most assuredly, the teen's still open and dilated hole would be oozing
sperm all the way there.

The End