This story contains graphic descriptions of sexual acts between a man and a minor boy. The story is not true; the sexual acts described herein derive solely from imagination. It is not intended to promote illegal acts with/to/by minors, nor does it condone child abuse of any sort. If you object to the subject matter, stop reading. If you are legally under age to be reading this, or if your reading of this material otherwise violates laws in your place of residence or where you are currently located, stop reading. Thank you.
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My stories are pure fantasy. If they do nothing else, they ask, "What if..." Those who wish to comment, may email me at email@example.com.
Before this, the concluding chapter of Island Boy, I'd like to take a moment to thank Richard for his generous and invaluable assistance as an editor. (Thanks, Richard!) I'd also like to thank Nifty's readers for their patience. In addition, to those who have emailed me with their encouragement and suggestions, I offer my heartfelt gratitude.
- Will S
Chapter 13 of 13FROM SEAN'S JOURNAL
Randy was at my door exactly on time the next day and the next and the next. And I was ready for him. It was odd. It was not an obsession - nothing like that - but I've found myself taking a lot of time figuring out how to do what I need to do to prepare him. Jason and I have talked for hours about child sexuality, and Randy in particular. "You're the one he's putting all his trust in," Jason had said at one point. "He thinks it's all about sex, but you and I know there's more: It's about building trust, teaching him about relationships, giving him an experience that affirms him. For so many of the boys on this island, all of that is entirely new." I nodded, and again hoped I was worthy of the Jason's trust in me.
"On a less "lofty note," I'd gotten the impression Randy liked the plug, and on the fourth day, he proudly showed me how easily he could slip it in and out.
"Maybe it's time to move on to something bigger? I've trimmed my fingernails." I said. In our times together, he'd expressed a quiet concern that his insides might be scratched by my fingernails. I wanted to let him know I listened to him, took his concerns seriously, and wanted to do nothing that would injure him.JOURNAL ENTRY ENDS
The lewd little boy, lying naked on Sean's bed lifted his legs and stretched them out so he was almost doing a split. The effect was to expose his anus and the plug firmly in place. He smiled a really lascivious smile and raised his eyebrows questioningly while glancing down at the older boy's cock. (It was usually boned up pretty good whenever Randy was around.)
"No...I don't think so...a long way to go yet, sport. I'm sure you'll agree," Sean said, reminding him of the difficulty he had with his finger a few days ago.
"Here," Sean said, "Let's see." The child's mentor leaned in and grasped the handle of the butt plug and pulled. His asshole seemed to want to keep it for itself, but eventually, it did pop out. Randy was right; it was easier.
Sean lay down on the bed, with his back kind of propped up by a couple of pillows and the wall.
In an instant, the naked little sprite was nestling himself down onto his mentor's cock. Not that he was trying to impale himself; rather, he was simply enjoying the feel of the large, erect penis between the furrow of his two beautiful hillocks of boy butt. He'd discovered the he liked the feel of that, and Sean figured it was a good way of getting him used to their special closeness.
The older boy reached for the KY.
"You feeling brave?"
Randy focused on his mentor and grew more serious. "Yes," he said expectantly.
"We're going to work a little harder today," Sean announced.
Randy nodded and Sean could see just a hint of uncertainty in that boyish face.
"First things first," the older boy said as he reached out and shifted him backward, so his legs were on either side of Sean's face and his crotch was at his mouth.
"Assume the position," Sean grinned. Instantly Randy complied, his legs folded, back and out.
The older boy effortlessly pulled his charge to him.
"I love the fragrance of your butt," Sean whispered, and now he leaned in and planted a kiss on his little pink spot.
He pressed himself against Sean, so he kissed him again.
"Oooo," he breathed.
"Mmmmmm," he moaned. The sound eased, becoming a sigh straight from the heart.FROM SEAN'S JOURNAL
I'd never done what I was about to, but hell, I'd gone this far. I slid my tongue out through my lips and ran it around his hole.
"Ahhh," the boy moaned. "What did you do?"
"Was it nice?"
"Yessss," he sighed.
"I wanted a little taste."
"Do it again. Please."
I couldn't refuse such a sweet boy. I reached in again. A shiver passed through him. Again he pressed himself on me.
I pulled back. "Yeah?"
"Sean, put it in."
I hesitated. Ralph loved doing that, but I never could - or wanted to. But here was my little boy, asking in his most angelic tones.
I extended my tongue again, and found the right spot.
"I'll push out now," Randy said, with all the enthusiasm of an eager student.
I felt him push and I entered. He actually squealed with delight. Then he clamped down, I worried I might never get out, but slowly, I discovered I could actually push in a bit and pull out.
"Ooooo, Sean....it feels so cool."
I got in as deep as I could go, and finally, pulled out.
"Ohh," he said sadly.
"Hey, sport, we got'ta be careful, or we'll strain my tongue muscles," I joked.
"What's it taste like?" he asked with typical boyish curiosity.
"Like Randy-ass. Not bad." In truth, it wasn't bad.JOURNAL ENTRY ENDS
"I bet you're ready for something more, now." The little boy looked expectantly up at Sean. Those eyes were killers. They said, "Ye-s-s-s, I want it - whatever it is."
Sean slid up on the bed and patted his lap. Randy scrambled up into it in a flash. In the most natural way, his butt crack settled on his mentor's throbbing meat. He looked up and smiled, always looking for approval. "Nice," Sean purred and the little boy beamed. Sean wanted him to know that sex was about mutuality: things that made you feel good also made your partner feel good.
The two boys lay that way for a few minutes. Unlike a lot of twelve year olds, Randy never seemed to be in a hurry when it came to contact between the two of them. "Let's try the finger again," Sean suggested. He saw a look of uncertainty in the young boy's face. "Hey...remember, it's all exercise. The weightlifter can't lift 600 pounds the first time; he's got to work up to it." Sean moved his hand under Randy's long, shiny hair and found the spot behind his ear and began to work it. He purred.
With a trace of reluctance, he complied. Adjusting himself, so he was sitting up a little more, Sean commanded, "Spread 'em." Tentatively, Randy reached back and pulled at his exquisite hillocks, revealing a valley between them that drew the older boy to the center.
Sean reached for the KY and squeezed some out on his fingers.
"Okay, Rand...here we go." Sean gently reached down and let the lube on his fingertips touch first. There was a perceptible quiver as Randy's chute involuntarily sought to protect itself. Sean lowered his fingers the remaining eighth of an inch to make contact. Again, a contraction. The older boy smiled.
"Okay, now I'm just going to leave it there, okay?"
"Mmm-hmm." The twelve-year-old seemed relieved.
In the past few days, Sean's finger had rested probably a total of 40 minutes on that magic spot. He was prepared to let it rest another 40.
"Do...you want me to try?" Randy asked hesitantly.
"Mmm...not yet...let's just wait."
"Okay," the boy answered, again sounding relieved.
Sean leaned down and kissed one of Randy's sweet butt cheeks. Then he rested his other hand on the place he had just kissed.
"Randy," Sean said softly. "I know it hurt a little bit the other day, and I'm sorry." He offered a reassuring smile.
"Sean?" the youngster asked after a moment of thought.
The older boy could see him working something out. He wondered what it was going to be.
"Umm...it's gonna hurt...isn't it...when you really do it, I mean."
"The truth?" Sean asked. His student nodded tentatively. "The truth is, yes, it'll hurt...but that's why we're going so slow...so you body can learn how to open itself to me...and, Randy, so you can learn what to expect in terms of the pain. If we can work on both of those things, it'll be much better, I promise." He seemed to understand. "And, my goal is not to give you pain, my sweet boy, but to give you pleasure." Sean thought about explaining how the pain actually transforms into pleasure at one point but decided that might be something to talk about later. "Just one more thing, my sweet..." He blushed when I called him that, and then Sean lifted his chin. "...I won't ask you to do anything you can't do, and that's a promise, too!"
Randy sighed deeply. His mentor could feel the young boy's muscles relax. He lay there unmoving, which gave Sean a chance to drink in his beauty once more. Perfectly proportioned, perfectly muscled, perfectly covered with perfect velvety-smooth skin.
He was on the cusp of puberty and his body was losing the soft edges of childhood. In their place were those incredible "more-defined" angles of adolescent boys. From the back, it was easy to see the tapering of his torso from his shoulders to his waist. If Sean hadn't viewed their time together as a lesson - as working - he'd have grabbed him up, pressed the young boy to his body, and run his hands up and down his back to savor the feeling of the exquisite boy's form.
"Okay, Ran...let's try...just the first part. You know you can take that. Okay, bud?"
Slowly, Sean eased his finger inward. "Push out for me now."
The older boy felt him open, and he pressed in.
"Ahhh..." he sighed. He'd gotten his finger in until most of it had disappeared.
"Mmm-hmm," he shuddered. I could tell it was tight.
"Hey, Randy, stay loose for me down there, okay, big guy."
"You know what?"
"I'm in as deep as I've ever been."
He giggled boyishly at that bit of information.
"Okay, now, I'm not going any deeper, just gonna turn it a little."
Sean did exactly that.
"Ahhhh..." The boy's body stiffened and he trembled, sucking in a sharp breath.
A silence. "No."
Sean figured the child's hesitancy said more than his strained, one word answer. Ralph's solution in this would be to push in one massive attack. "Bust that kid's cherry. Make him know he's been fingered!" But that was Ralph; it was not Sean, who now pushed in deeper. Randy panted rapidly, reminding Sean of a woman in labor. Periodically, the boy's body would stiffen and he'd arch his back. His little rectum tried to push me out, but Sean was having none of that.
"Randy, how're ya' doin', buddy?"
There was no response - only the desperate panting. Then finally, a little cry: "okay."
"Hey, bud, you know what?"
He snuffed once, then as he sucked in a breath: "What."
"I'm in all the way."
Now the little trooper drew in a deep breath and held it, trying to regain his composure.
Sean leaned in and kissed him on his right butt cheek. "I'm so proud of you, sweetie. What a trooper."
His breathing eased now.
"All the way?" he repeated timidly.
"All the way."
He seemed to understand this meant the work was done for the moment, and the older boy sensed him relaxing. After a moment Sean also felt his anus relax.
"Randy, I can see you're thinking about something."
"Yeah...like why does it hurt so much? I mean, it's just a finger," he said, truly curious.
"Just 'cuz you're not used to something pushing into you. Usually something is coming out...not in."
It took him a moment before he realized exactly what Sean meant. "Gross!" he squealed, and then he grew quiet. Something else was on his mind. Finally he screwed up enough courage to ask: "How...how old were you - your first time?"
"Fourteen...goin' on sixteen. At that point I was kind'a advanced, I guess."
"Fourteen?" he asked incredulously.
"Yeah, you got a problem with that, bud?"
"No...I guess not...but...how could you wait that long!" the boy asked genuinely mystified.
"I guess I wasn't as advanced as you are, you little horn toad!"
Randy giggled a small laugh and Sean felt a tightening around his finger.
"No...no really...I dunno exactly, kind'a makes my penis feel...I dunno...maybe stronger."
Sean smiled. He knew exactly what he meant.
"You just wait, Ran. You just wait."
"If you were fourteen, your...um...your hole must have been bigger."
"Than yours? I'm sure."
"An' it still hurt?"
"At first. Randy, it's just that for your whole life, your body has trained itself to keep your anus shut tight. But now all of a sudden, you're telling it to open up...and it's all confused. We have to kind of retrain it. And it's learning...but it just takes time. I think you're doin' great."
Sean felt a tiny spasm around his finger, and he realized just how tight the little boy was - and not just his anus. The entire chute was in contact with his finger. It was warm and slick. Sean felt his cock pulse at the mere thought of filling the boy with his manhood. Suddenly Sean had an overwhelming sense of love for this little guy.
"Hey...scoot down for a second," Sean instructed. His free hand guided him downward and his other hand, still engulfed by the sweet boy butt, lowered him like an elevator until they were eye to eye.
"What?" Randy asked curiosity.
"Just this," Sean said, and with his left hand at the back of his head, fingers running through his glorious, silky black hair, he guided the boy's mouth to his.FROM SEAN'S JOURNAL
We had kissed before, but now we seemed to discover a desperate need in the other, and drew our breath from the other. It seemed as if whole minutes passed as my lips kneaded his, and his, mine. My tongue explored his warm, hungry mouth, his soft, undulating tongue...his pearly perfect teeth, and then as he tongue-assaulted me, I finally yielded so he could achieve victory and reconnoiter my equally hungry maw. When our tongues seemed to need a break, we'd just go back to kissing and nibbling.
In the midst of this, the little tyke began grinding his cock into my belly. I reminded myself of our assignment, and focused on the tight chute which impaled my finger. His anus was definitely more relaxed.
I wondered if I would be able to find his miniature prostate, but I didn't want to waste that first virginal contact. I broke away.
"Wait..." there was a desperate quality to his pleading. Clearly he wanted the oral contact to continue.
"Tell you what, bud. I'm not going to pull out, but I am gonna' move around inside a little bit. Tell me what you're feeling. An' I bet you'd like some attention a little lower than your mouth."
"Right, you twerp!" I sucked his beautiful little chin into my mouth. It was about as big as some of the cock heads I'd sucked, but he would have none of it.
"Eeeoooww....I didn't think you'd do it," he said with a tone of indignation.
"Well...give me something else to suck on, if anything comes to mind." Slowly he pulled himself upward, and I again assisted.
I must have looked cross-eyed doing it, but I glanced down to check out his little cock. It was standing there, all straight and proud.
Ever-so-gently, I pressed my finger against the side of his rectum, and he squealed in delight. At the same time, he virtually drove his cock into my waiting mouth.
"Mmmm," I moaned, and began to work in earnest, stopping only momentarily to draw in his tiny balls and sac as well.
In no time, he was ready to explode. With my left hand supporting him on his back, I could feel his breathing change. Little preview quivers spread across his body. All this time, I was pressing about inside him, and it was only adding to his pleasure. With each breath, there was a tiny, almost mouse-like squeak that came from his throat. His small hands clamped down on my head almost as tightly as his anus clamped on my finger.
Now, expecting him to orgasm at any second, I sucked and tongued his genitals with renewed effect. I was rewarded with the first orgasmic quake. His anus opened, and I withdrew some.
"Aaaahhh." He stiffened all over, and arched his back.
"Mooorrre," he moaned...."P...put...it...baacck."
Again he quaked, I shoved it back home."
"Aaaahhhh." Again, and almost violent pulse of orgasmic energy: amazing power unleashed in a twelve year old.
Now, I began to probe. He was close, so I knew I didn't have much time. I pressed in....forward...a bit deeper...then back, and then...I found that sweet nugget of gold deep inside a boy. Randy actually screamed out one of those high-pitched boy screams you hear on the beach or on the playground when a man-child is in a place of complete ecstasy.
Suddenly his little penis seemed to stretch even tauter and was overpowering my tongue as it angled up toward the roof of my mouth. I kept my tongue at the slit at the tip, and I swear I felt a tiny drop of something emerge. The pulsing continued. And as I touched his prostate - the magic spot deep inside him - again and again massive quakes emanating from his cock spread throughout his entire being. I surveyed his little body, and every muscle seemed stretched to the limit. His back arched backward, and his head was rolling wildly; he was whimpering like a puppy overcome with happiness.JOURNAL ENTRY ENDS
It was enough to make Sean worry that maybe they were going too far, and he began to ease off. It seemed like the boy's orgasm could go on for minutes, but now, slowly, his waves of orgasm slowed and finally stopped. The tremors eased, and his soft hands slipped from Sean's head, down his neck and shoulders, and lower to his back. Randy was completely limp now, and his breathing eased back to something approaching normal.
Slowly, Sean pulled out of Randy's rectum. Any resistance had disappeared.
Like a mother - or like the lover that he was, Sean gently laid his 85 pound sweetheart on the bed. He was sleeping peacefully, a broad, easy smile on his face. Sean grabbed a towel and wiped off his hand, then took the opportunity to examine the boy to whom he'd just made love. Clearly, the butt plug had helped, and his little pucker was indeed beginning to look more like a pucker. Some of the initial smoothness was gone; now it remained red, showing the trauma that had been visited on it. Yet it remained slightly open. Sean reached for the next larger plug, lubed it, and gently inserted it. It slipped in relatively easily. Randy stirred slightly during the operation, and the smile grew.
Sean lay down next to the boy and pulled him up on top of his body. As if compelled by nature, the little boy instantly snuggled against his mentor. He surrounded the older boy's neck with his arms, and wrapping as best he could, his legs around Sean's waist.
For most of 20 minutes, Sean had been a throbbing bit of iron, and now it seemed to dawn on him he needed release. He lubed himself, grabbed on, and then began to work.
Some degree of consciousness must have manifested itself in the younger boy, because almost immediately, his body eased downward and he pulled his legs together, enveloping Sean's hand and cock. Once Sean's cock was out of the way, Randy's legs squeezed tighter, and Sean could feel his charge's little sac against his shaft. Randy's body quivered down there, but whether his brain had trouble communicating to his muscles or whether he was simply too exhausted, his little body seemed incapable of moving beyond trembles. Even that was exquisite, but gently placing his hands on either side of the boy's hips, Sean lifted, and then lowered his body. The feeling was electric. Again...up...down...then again....again...soon, Sean could feel his own body responding and whether consciously or by some primeval drive, he began pumping. In barely a minute, the older boy shot. Great bursts shooting high in the air above them, more being trapped between our bodies. Sean's orgasm was no match for Randy's in terms of time, but in intensity...Sean was rapidly approaching the same nirvana Randy had experienced. When the older boy finally could release no more, he gently eased his autonomic movements, and both man and man-cub rested.
In his dream-like and timeless reverie, Sean slowly became aware of a boy's warm, wet lips on his.
"Mmmmm," he moaned, and opening his eyes, Sean saw two jet black eyes, sucking in his very being. The older boy smiled, and the younger boy smiled back.
"I thought you were dying," Sean said softly.
The little boy grinned a boyish smirk. "So did I...Never..." was all he could get out, then he snuggled down and they rested some more.
They slowly revived, and eventually, when Sean suggested it was time to wrap things up, Randy poked him, and naturally, the older boy retaliated.
Soon they were in a good old wrestling match which both knew Sean could win with one hand tied behind his back. It was a sensuous scene: both struggling against the other.
Sean could tell Randy was getting worked up again, and he did nothing to throw cold water on the younger boy's passion. In the middle of this, the small boy rolled him off him, and Sean, in turn, knelt above his student, straddling his chest. Randy looked up at his mentor with those big, black eyes. Sean's cock hung down just about over the boy's small package as the older boy crouched over him. Gently, but firmly, Sean entwined his ankles over the smaller boy's, effectively pinning his legs. Now he reached out, spread Randy's arms somewhat, and pinned them.
The little boy was now more or less immobile. With a huge grin, he realized his predicament. And then he commenced to struggle for his freedom. Sean watched Randy's eyes, sparkling with energy, as he struggled. The older boy could tell he was having fun, but he didn't realize just how much. As he held him immobile, he'd occasionally lower himself to lick one of his charge's little nipples. They stood up like arrow tips and they were the closest in size to Sean's as anything on his little body. Now Sean noticed his breathing had changed, and his grin faded. Sean still wasn't sure exactly what was happening. He thought maybe, just maybe, Randy was tiring of the little game of domination. Sean thought he actually might be getting a little angry as he struggled, and was getting ready to let him get the upper hand, when he realized what he was witnessing was not anger at all.
Suddenly a cry broke from Randy's throat - a cry of ecstasy. He abruptly stopped struggling. His little muscled body stiffened and impossibly arched, lifting his mentor with him. Sean could see and feel the shudders of sexual energy coursing through his body, wave and wave and wave. The older boy started counting the seconds. Randy's beautiful head began thrashing back and forth, and his breathing rasped in desperate ragged breaths. His eyelids fluttered and his eyes lost their focus. Whimpers of exhausted joy came with each breath. 20 seconds...30 seconds...35... Sean finally eased his grip and tried to minimize body-to-body contact. Slowly, the younger boy settled down back onto the bed. It was the most unbelievable orgasm Sean had ever witnessed.
They had made an important discovery. Little Randy got off (really off) on restraints and domination!FROM SEAN'S JOURNAL (Two weeks later)
These past two weeks, we had gone from the smallest butt plug to the largest one in the set. The last one was really tight, but we both knew he would soon be experiencing something even larger. Jason had been very careful selecting the plugs for Randy. He knew Randy could take a larger plug, but he wanted him to be ready for me, without losing the impact of his virginal deflowering.
Now, that moment was at hand. Together Randy and I walked to the office area. He seemed to understand the import of what was about to happen. As we left my room, he took my hand in his and we walked like that all the way to the medical area. Along the way, we saw other kids on the island. Some just looked, knowing what was about to happen; others shouted encouragement: "You can take him, Randy," shouted one boy. "Make him work for it!" Randy smiled quietly, looking amazingly shy all of a sudden. As we neared the offices, one small boy, probably about ten came up to Randy and we slowed.
"Good luck, Randy," the little tow-headed boy offered in breathless, boyish whisper.
"Thanks, Sam," Randy said quietly.
"I'll be waiting...You got'ta tell me everything"
Randy smiled and nodded. I knew Sam had more than just a passing interest. He had already told Jason, he wanted to see how Randy managed, because he had been dreaming about getting fucked for the past couple of weeks - ever since Randy had started his training. I smiled, and rubbed my hand in Sam's hair. If I followed my impulse at that exact moment, I might never leave the island.JOURNAL ENTRY ENDS
The two boys entered the office area, proceeded immediately to the stairway, and descended to the medical level. Sean remembered the area well, especially the restraint room. It was where Jason did the biopsy of his testicles. He would forever associate this room with pain.
Both Randy and Sean knew that what was about to happen would only reinforce that.
With the door closed, safe inside the padded exam room, they stood facing each other. Sean gently moved in and kissed Randy on the forehead, then the eyes, the nose and finally the mouth. He did this slowly, lowering himself to come closer eye-to-eye. Little Randy stood still as if a virgin sacrifice.
When the electricity of our warm lips touching flowed into the little boy, he responded. As if starved for contact, he greedily thrust his sharp-pointed tongue into his mentor's mouth and explored it. When he was satisfied, they reversed roles, and the older boy probed with his tongue. Sean's hands drifted downward, exploring Randy's firm body. One of Sean's hands covered the entire right side of the small boy's chest. I could feel his heart pounding, already reacting to our brief time together.
Sean's hands moved around his student's beautiful torso. And finally, not satisfied with the cotton that was between them, he slipped his hands under the shirt. He was instantly rewarded with the exquisite softness of a small boy's smooth, soft skin. Again, Sean sensed a change in the boy's breathing. In something of a ritual, Sean gathered the T-shirt and lifted it over Randy's head. The boy raised his arms to facilitate its removal.
Quickly Randy unbuttoned Sean's shirt and it slipped off his shoulders.
Now their hands joined in a slow, sensual game of exploration. For his part, Sean was rewarded with the rising of two nail-point nipples. He lowered his mouth to first the left one and bit gently and pulled. Randy rose right up onto his toes and squealed with delight, anxious to get on with his initiation. He tugged at his mentor's shorts, and he let him remove them, but held his thong in place.
"Uh-uh," Sean breathed, wagging his finger to warn him off. He looked quizzically at Sean's swelling basket hidden - barely - under the thin material.
Now Sean's hands slowly began the first tentative forays downward, both in front and in back. As his fingers became bolder, Randy began to push himself against the older boy's hand. Little moaning puppy sounds slipped from his throat.FROM SEAN'S JOURNAL
I'll never forget what happened next. Jason had been coaching me every step of the way, and now what we were about to do filled me with awe. This moment was huge for this little, desperate boy, and I slowly proceeded to get him ready.
I slid my thumbs into the familiar terrain around at his hips, hooked his shorts and eased them down over his rigid pole. His tiny white briefs stood out like a circus tent. He stepped out of his shorts and grabbed my hands in his, trying to spur me on.
"What!" I cried. "Trying to make me hurry...why you..."
I gathered him up in my arms and held him tight. He struggled to pull away. He knew the game had begun.
With his legs locked around my waist and his arms strangling me around my neck, he buried his tongue once again in my mouth. We worked at that for a while longer.
Then, panting like a dog, he begged me, "Please don't hurt me."
"Hurt you?" I exclaimed. "You don't know hurt!"
His eyes sparkled and I could feel his heart pounding against my own chest. He wriggled to free himself from my grasp, but it was futile.
I stepped to the exam table and leaned down so that the boy was trapped between me and the table. Only then did I release my grip of him, and reached on either side to find the straps that would bind his chest.
"No...no...please..." he cried, breathless with anticipation.
In the past week, our little S&M games had become more explicit, but I had studiously avoided really hurting him in any way. There were times when he was on the edge of pain, but it was always linked to pleasure. Today, even if I wanted otherwise, the pain would be there; it would be real not matter how much we'd try to avoid it. At some level, my sweet, pure Randy knew that, but I doubt he could really know what was in store for him.
In a flash, I had the chest restraint in place. He struggled under me, trying futilely to free his legs. His little poker pressed into me, and I purposefully adjusted myself, so the cloth-covered organ pressed into my navel. I stretched his right arm out along a board and strapped it down. Then I did the same to his left arm. Now I reached lower and drew the pubic straps up and around his hips. Holding his legs firmly in my hands, I folded them, then slipped the left one in the stirrup and locked it, then repeated it on the right side. He was immobile now, and despite how he strained, he could not free himself.
The little tiger had actually worked up a bit of a sweat with all his efforts, so I got an ice-cold wet cloth and wiped him down. Even that he railed against...though he was at my mercy and he knew it - savored it, even.
What a vision: black straight, glistening hair...eyes like pools of black gold...cheeks of the smoothest skin...a cute little button nose, as yet unspoiled by the typical deformation of puberty's growth spurt...red, swelling lips caressing perfect white teeth...a strong, proud, extended neck...heaving chest...straining muscles in two outstretched arms...tiny spikes of nipples...the musculature of a boyish tummy...legs straining in the stirrups...and the rest of his treasures cruelly hidden from me.
But that was about to change.
I reached for a pair of medical scissors - the kind with the blunted tips and used for cutting bandages - and turned to him. Light glinted off the shining hard steel, and he was immediately focused.
"What are you going to do?"
I lowered the tip of the scissors to his tummy, and he sucked in a desperate breath. The scissors were cold and hard and smooth. His belly tightened in a sort of spasm where the instrument touched down. Now I lightly dragged them over his tight cotton briefs and around his tented maleness. I could feel the organ throb under the touch of the instrument. I smiled at him.
"I'm going to cut something off."
His eyes widened, and he struggled even more. Deliberately I lowered the scissors to the left side of his white underpants. In a flash, I had cut from the elastic waistband down to the seam at his leg opening. Immediately, his penis stretched skyward even more, pulling the left side of the freed garment along with it. Now I cut the right side. Then putting the scissors down, I carefully lifted the garment, now more like a thin, form-fitting diaper, up away from his body and laid it down between his legs, exposing both his genitals and the stretched crease between his taut buttocks.
He was stiff and hard all over. Our little game seemingly had sensitized every part of the boy and he breathed shallow breaths in anticipation. I pressed some buttons, and immediately the exam table lowered overall while raising the end under his butt, bringing it just to the optimum level and angle for entry.
Then, slowly I leaned over to begin a slow tongue bath. Whether due to his being bound or by his anticipation, he was desperate for contact. Keeping him as immobile as possible seemed to drive him wild. Little whimpers came with every breath. Finally, when my mouth found his, he ferociously assaulted my hot, wet maw. We greedily devoured each other, and I marveled at the insatiable appetite of the little black-eyed catamite.
I reached down under the table to a small shelf. It held a bowl filled with KY. I dipped my finger in it and moved to his rosebud. It quavered when I touched it, and Randy immediately quieted, seemingly understanding his time was at hand. As gently as possible, I entered the boy who had become so skilled in the past days. My finger slid in easily, and I moved it about, loosening him, preparing him. His eyes seemed to sparkle in anticipation.
Always a talker, now, he suddenly he grew silent and still. Only his chest and tummy heaved up and down with the irregular breaths of anticipation. I withdrew my one finger and slid two in. I could see Randy bare down with concentration, working to relax and be open to my probing. His insides were soft and firm and hot. His own natural lube began to meld with the KY, and his tummy muscles began to tense in anticipation.
With my other hand, I slathered my seven inches with lube and waited for the right moment.
I leaned over him, positioned so my slick cock played with his tiny ramrod. I leaned down and kissed him on the mouth.
"You ready for this?"
Words still eluded him and he simply nodded.
"It's gonna' hurt, you know...for real."
"I know, Sean."
"Tell me if you want me to stop."
"I won't." He managed a smile. "Do it, Sean. Please. Now." I could see his heart pounding below his smooth, luscious chest.
My dripping penis throbbed in anticipation. I looked him in his dark eyes one more time, then took my cock and let him feel the taut terrain around the boy's hole. The tiny pucker contracted predictably, but the mere touch of my dick there caused a visible arousal in the boy and all his muscles stiffened once more. I guided my cock head to its mark, and glanced up. It was as if my oozing slit were kissing his sweet, tight hole.
Randy forced a smile. I knew it was meant to be reassuring to me; he wanted it to mask his sense of uncertainty, and even - perhaps - fear. I looked at his taut face, and offered a smile in return and hoped it was indeed more reassuring to him than his was for me.
I pressed in, letting him feel the firmness of my smooth head against his hole.
The pretense of the smile faded, and in its place came a look of utter concentration.
"All right, now...open up...I'll wait 'til you're ready..."
I watched him summon all his willpower.
The pucker that had clamped shut, eased. I stayed still, and miraculously felt him open more. I hadn't even got in him, and he was sending bolts of erotic electricity throughout my body, my spear acting like a lightning rod. Through my glans, which pressed against him, I could feel even the subtlest of movements of Randy's virgin anus.
Those clear, black pools of his eyes bore in on mine. I nodded slightly and then began to press in earnest.
"Push out now," I whispered.
Despite all our work, and all my fingering, I met resistance. The little boy sucked in a sharp breath and held it as I pressed. He seemed to understand I was not to be denied.
His anus clamped down again and squeezed the very tip. He shuddered once. Immediately a look of concern filled his face.
"I'm sor..." the boy began to say, but I put my hand to his lips and stopped him.
"Shhhhh..." I said gently. "It's okay, Randy. We both know this is going to take some time. We'll wait just a bit. You'll loosen up." I smiled; now it was my turn to be reassuring. While I waited I could feel the boy's tight hole working on the tip of my glans, and so, while he worked to relax, so did I. It wouldn't take much of his exquisite movement to send me over the edge.
"You better relax," I grinned, "'cuz if your asshole keeps nipping at me, I'm gonna cum even before I get inside."
He grinned a great, broad smile, then, as if settling down to take a test, grew more serious, and after a few more seconds, I felt him open a bit. I knew what I had to do. There was a point in every deflowering (I remember that moment only too well when I was initiated) when the kindest thing is also the cruelest.
I leaned down, struggling to cover his torso with my body without moving my cock from its position. Leaning on my forearms, I let my fingernails scrape over his b-b-like nipples. Contorting my back and neck, I managed to lower my lips to his, as he stretched upward. As I thrust my tongue into his hungry mouth, I stiffened the muscles of my buttocks and rammed into the boy's resistant hole. Instantly his mouth clamped down on my tongue. I thought he was going to bite it off. At the same time, he began to breathe with short, sharp, desperate breaths through his nose.
I felt my head move deeper into him, stretching him, forcing its way past that incredible ring of muscle. The pressure on that smoothest part of me was like nothing I'd felt before, and involuntarily, every muscle in my body tightened, as his squeeze triggered some primal response.
I could feel Randy stretching despite his body's best efforts to remain closed, and with one more final push, I pressed past the ring just a bit more so my head was fully encased. His whole body shook and a whimper tore from his throat.
I pulled back from his mouth, and kissed him everywhere I could reach.
"There, there, there," I murmured softly, not, I thought, unlike a mother comforting her child. "That's the worst, Randy. The worst is over. Just relax. Don't try to talk..." Tears welled up in his eyes, making them even brighter, and I struggled with a twinge of guilt, again, remembering my own initiation, knowing his - because of his tiny body - would be worse.
I struggled to temper my movements. My body was on autopilot; it was as if it knew its destination, and it would not be denied. My brain shouted, wait! Wait. I knew I had to. A sheen of sweat spread across the boy's forehead and his arms felt almost clammy - damp and cool, yet betraying a deeper warmth of hot blood. If I pressed on now, it could be too much for him. I knew - if he was like I had been - he would be afire with a thousand relentless pin pricks, tearing at him down there.
Now, miraculously, his breathing began to ease, and holding myself as still as possible, I let my hands massage his taut body.
Now, another hand caressed the boy, and then a hand on my ass as well. I looked up. It was Jason. He smiled, and I smiled. Somehow it was perfect, having him there. He'd been my guide for the best years of my life. He'd guide me through this as well. Jason was naked, and as I bent over little Randy, I felt Jason's meat press against my back door. I gasped, and took a breath and opened myself. Jason rammed into me, and I whimpered even as my little boyfriend was doing.
"What's wrong?" Randy said, not realizing what had just happened.
"Nothing, son," Jason whispered. "Sean just has a penis in his bottom just like you're going to." Now Jason whispered in my ear: "Rub his tummy, Sean, help him to relax." I felt Jason's hand on my belly, modeling the behavior he was suggesting, and I felt his manhood pulse deep inside me. It hit my spot, and my own tool flexed. The little boy winced.
I did as Jason instructed, feeling the little boy's soft, smooth skin. He was exquisite perfection. I felt Jason's arm snake under mine, and then Randy moaned. I knew Jason had wrapped his fingers around the boy's tiny cock. "Take him," Jason whispered in my ear. I felt like I was about to explode. Jason was buried all the way in my ass, and now I felt him pressing me forward, forcing me into Randy's tight little hole. It gripped my meat like a vise. The little boy's face was screwed up like he was dealing with the worst pain in his life, and quite likely he was. I locked my hips, putting a halt to Jason's thrust. I had a good six inches left to go. "Try to relax, honey," I whispered. "Try. Open up to me. Let me feel you open up." I rubbed my hand in swirling little circles on his tummy. Now Jason drew his cock out of me, and I felt the familiar emptiness before he shoved it back into me. I gasped, and jerked another inch into the little boy under me. He whimpered, but then, unbelievably it was as if the flood gates had been pierced, and I felt him relax. I grasped his hips and pressed in, all the time with Jason humping my ass with his throbbing cock. He was driving me wild, and I really wanted to be able to focus on Randy, but I was losing that battle. With every thrust of Jason's hardness, Randy's frame shook. Each thrust of Jason's meant my penis would assault the boy with a sort of aftershock. And each time that happened, Randy would grunt.
Finally, it was as if something let go deep inside him, and I bucked the last two inches deep into him while at the same time pulling away from Jason. It set me on fire.
"I'm all the way inside you, Randy," I gasped.
The little boy could only whimper in response. Now I felt Jason's hands on my hips, and he pulled me back. Just my head was held by the little boy's pucker, and then I felt Jason pulling out of me. He held for a moment and then shoved back into me. I groaned loudly and thrust into Randy. He cried out, and then gasped as I again pulled out. After half a dozen thrusts, we'd established a rhythm. Suddenly, the little boy cried out again, but not in pain this time. It was like a switch had gone off, and he was now suddenly in ecstasy. For the first time since I'd first gotten my head past his rim, his eyes seemed to focus on mine. He managed a smile. "Fuck me hard, Sean, please," he murmured.
"You heard the lad," Jason whispered. "Just like I'm gonna do you!" he snarled.
What ensued was an incredible, frenzied bout of mad fucking. There was no finesse, just muscle working on muscle. The little boy strained at the restraints, muscles popping as he desperately tried to break free. Wave after wave of violent shudders flowed across his small body. His head slashed back and forth like a trapped wild animal. He was barely aware of where he was. All he knew was that he was being assaulted by the most incredible sensations his young body had ever felt.
Jason came first, flooding me with bolt after bolt of hot cum. That sent me over the edge, and now I shot harder than I had in years of incredible sex. Randy's little poker was hard as iron. I grasped the tiny organ, and got off half a dozen quick strokes just before I came. And then he was screaming like a little boy on rollercoaster. His whole body convulsed in a grand mal seizure of sexual release. Shudder after shudder assaulted him. And only after I'd finished spending, did his contractions ease. I was exhausted, but Jason kept me pinned to the boy, even as he kept himself pinned to me. I breathed in a deep breath and swallowed hard. "Oh God," I breathed. Now Jason pulled his softening tool out of my ass. He slapped me hard on my butt, and Randy stirred in his deep state of resolution. He breathed in long, slow breaths, completely relaxed.
I started to pull out.
"No," whispered my mentor. "Here's a secret, Sean. For as rough as you are when you take their virginity, you must be equally gentle afterward. Wait until you are completely soft before you pull out. It will be better for him. Now I heard Jason getting something out of a cabinet. He had a tube and some other things. He saw my questioning look. "Basically," he said quietly, "we're going to douche his hole with an anesthetic. He'll still be sore, but it won't be as bad."
Carefully we filled the little boy with a soothing enema. Jason had a tiny speculum, which he gently inserted into the boy's anus and held it open as the fluid laved his insides and then drained, bringing much of my spunk with him.JOURNAL ENTRY ENDS
"You came hard," Jason observed as they watched the small figure in restraints. He was breathing slow, easy breaths, completely relaxed.
"Yeah," Sean replied, "thanks to a little help." They both smirked. "Jason," Sean began, "How come you made me attack him so hard? You didn't do that with me when you took me for the first time."
The doctor smiled. "Every boy is different, Sean. You will learn what each boy needs. Randy needed to feel that pain - in order to feel the other side of it later on. When we fucked for the first time, you were a very different boy. Your needs were not Randy's."
Sean knew his mentor was correct, and he nodded his agreement. Together, they unstrapped the little boy, lifted his legs out of the stirrups, and Sean lifted him up. They carried him to the bedroom where Sean had lost his virginity all those years ago. They laid Randy down in the bed and they watched as the nude child stretched and twisted to find what was most comfortable for him.
"Look at him, Jason," Sean said. Jason could hear the tender love the eighteen-year-old had for the little boy.
"He's a beauty," Jason sighed. He reached down and fondled Sean's butt. "But then, in one way or another, every child on this island is beautiful." He stroked Sean's ass lovingly. "For me, however, there's only one I truly gave my whole heart to." He looked over at Sean and faint smiles of understanding eased across their lips.
"I don't want to go," Sean said.
Now Jason turned to him and they embraced, their tongues seeking each other out. When they broke, Jason offered, "There's a place for you here, Sean. There always will be. If you want to stay, you can. It's your decision - just as it was your decision to come here in the first place. You need to weigh the options. You'll be an important part of the island no matter what, but if you complete your college and medical training, you'll be able to make a different contribution. Someday you might find yourself is some desolate alleyway and come across a small, desperate child about to be abused by some sick molester...and you'll be able to help that boy find a better life."
In that moment - as in countless other moments - Sean considered how different his life might have been had Jason not found him that day. More than once, he thought, he'd probably have been dead years ago. Now, he was a productive and positive member of society - the society of the island, but his story was by no means unique; already dozens of "graduates" of the island were living similarly productive and fulfilled lives back in the world beyond the island. There were young entrepreneurs, artists, executives, carpenters, police officers, doctors, scientists, teachers, lawyers, even a clergy person or two. Some were happily fulfilled in heterosexual relationships, married and had families, some were happily fulfilled in homosexual relationships, married and had families; whoever they were, Jason could feel - should feel - a great sense of fulfillment himself, for the wholeness of their being - their emotional and spiritual health, to use those terms - was due, in no small measure to their time on the island.
"Each and every one of you," Jason had said time and time again, "has inside of you what you need to be; what you want to be." In the years young boys had been coming to island - and leaving as grown men - the truth of those words was evident. Evident, too, was the gratitude of these "graduates", for Jack returned often from a flight to the mainland, with mail containing generous donations to Jason's work.
Tears welled up in Sean's eyes. He was about to leave the place he loved most in the world; there was no avoiding it. "I know what I have to do," he murmured.
"I know you do, my love," Jason said tearfully. "I'll miss you so much...but it's not like you won't be coming back here for breaks."
"I know," the boy whispered. They held each other for the longest while, then Jason, knowing he had to help the boy move on, spoke again. "You're work isn't done with Randy. He needs you to be with him when he wakes up. That's what this place is all about, Sean. Giving boy's what they need most - love...not sex, not lust, but love - sweet, gentle, pure love wherein you share equally with one another - yes, at times in a physical way, where the sharing is profoundly tangible, but always in a way where two spirits can share the same space."
Sean nodded, and lifted away from Jason. He lowered himself into the bed next to the little boy. When their skin brushed against each other, the little boy turned in his sleep, bringing his body close to Sean's and they cuddled. Sean looked up at Jason, and the man nodded his approval. He was so proud of the young man, who was so lovingly comforting the small naked boy beside him. Jason picked up the sheet, and carefully covered both of them.
The doctor knew this was the beginning of the transformation. He knew Sean understood Jason was a boylover, just as the young man was coming to discover that about himself as well. They would always love one another - they'd even have sex on occasion - and in time, they'd live on the island as a couple, but for both of them, their true love would always be the Randy's - and the Sean's - of the world.
Sean heard the door latch, and he knew Jason had left. As he lay there with the young love of his life, Sean found a hundred thoughts percolating in his brain. He thought about how his life had changed since that day Jason had found him all those years ago. He was so grateful. He sighed and gently stroked Randy's small, firm butt. So, he thought, as his thumb ran lightly across the smooth skin, one story has come to an end...but there will be others. He sighed again, and felt the first stirrings of his manhood. The island was his home, and the people here were his family. Jason's mission would become his. He smiled and bent down, and kissed the little boy on his soft silky hair. A soft, warm, tear spilled onto the boy's head, and the child stirred just a bit. Sean held the boy tightly, and felt a welcome, awesome wholeness surging throughout his body. Slowly he drifted off to a blissful sleep.