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