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 will1599s@yahoo.com.


Island Boy
Will S

Chapter 12 of 13

(Four Years Later)

A knock on the door brought the 18-year-old Sean out of his reverie. Before leaving the island, he had one more task to perform, and the knock signaled the beginning of it. He quickly pulled on a pair of shorts and stepped to the door. Standing there was Jason, and immediately in front of him was a young twelve-year-old boy. The boy wore a look of anticipation, but also a look of concern. It was as if the boy had presented himself, and was desperate to pass Sean's inspection.

"We're here," Jason began. "You all set?"

"I sure am!" Sean reached out and gently lifted the boy's chin and smiled down at him.

This seemed to put the younger boy at ease, and he grinned shyly in return.

"Did you decide where you want to do this, Randy?" Jason asked.

The little boy blushed, twisted around, and looked up at Jason.

"I...I think the restraint room," the little black haired darling said softly.

Jason flashed a look at Sean, then back down to the boy.

"Is...is that okay?" the boy asked, turning to look at Sean.

Sean smiled. The boy's dark eyes seemed almost to suck him in. Over the past few weeks, Sean had come to know the boy in the most intimate ways. "It's your call..." His smile grew. "...but I think that's a perfect place."

The boy was clearly pleased. Sean thought about the little boy who stood before him. In their play together, Sean had quickly discovered that Randy enjoyed being restrained. He loved to feel barriers to his freedom; he loved the fighting against them. It seemed to electrify him even more in his erotic play. From his years of being with Ralph, Sean understood how powerful authoritarian sex could be for some people - little Randy included - and for that reason alone, the restraint room seemed a good choice; that plus the fact that the task that awaited them might very well require the use of restraints. The older boy long ago recognized a part of him sometimes enjoyed the play of authoritarian sex - but only so far (and never as far as Ralph was always wanting to push him). It was, he knew, an "acquired taste"; however, as far as he was concerned, Sean knew absolutely that he much preferred the gentle lovemaking offered by his mentor. Jason was able to give him exactly what he wanted. Each time they had made love, he was overwhelmed by some profound sense of fulfillment, completeness. When he and Ralph had played together, it was just that - play. Oh, it was satisfying to a point - extraordinarily satisfying at times - but both Sean and Ralph knew when they had sex, it was more about the physical act than anything else. Sean would be forever grateful that that was not the case with Jason.

Sean looked down at the young not-so-innocent Randy - a boy who was not much bigger than he was when he first arrived at the island. He smiled reassuringly.

"Okay, then," Jason said, "I'll just be on my way. I'll check in later, if you'd like." He caressed the boy's shoulders and ran his hand through his silky, black hair.

"Can you..." the boy said in reply, "...I mean, if it's okay with Sean."

"Of course it is," Sean answered. Both boys grinned. The fact was, Sean there was as much at stake for him in what was about to happen as for Randy. Over the years, he and Jason had talked a lot about their relationship and their sexuality. When Sean was at a place in his life to think about these sorts of things, Jason talked directly and honestly about man-boy love and the place it had in his life. Always, for Sean, there was the stark distinction between abuse - as with the man from whom Jason had rescued him - and mutual, shared love. And that was exactly what the two had in common - a deep, mutual, shared abiding love.

"I'd like to be able to do what you're doing...for boys," Sean had told Jason one day not so long ago as they'd begun to talk about Sean's future. In the immediate future was college, Sean knew that. But then what? Jason had suggested there would always be a place on the island for him - if that's what he wanted. As they lay in each other's embrace, Jason talked about what that would look like - the sense of responsibility it carried with it. As no other boy on the island had glimpsed, Sean was allowed to see "behind the scenes" of not just the day-to-day operation of the island, but of the philosophy and hopes and dreams Jason espoused.

"You're a boy-lover, too," Jason had told him one day, and Sean knew the truth of that statement. "Society says it's evil," Jason had said, "but it's power-centered abuse that's twisted; it's sick, and it is evil. Pure love for a young boy is something very different. The ancient Greeks understood that, but whether society will ever be able to recapture that or not, I don't know." Sean knew what Jason was saying was true, at least about his love of boys. After all, he'd seen it in himself; he'd seen it all around him. And so the day came when one particular young boy was ready to take his exploration of his sexuality to a different level. Sean had already told Jason the boy was a cutie - as indeed he was - and that he envied Jason's role as mentor for this boy. He'd said it with a grin, teasing the man playfully, and so he was unprepared when Jason suggested perhaps Sean would like to be the one to introduce Randy to sex. "After all," Jason added, "he's made it very clear he'd wish you'd pay more attention to him." Jason's eyes sparkled with a kind of teasing of his own.

What Jason didn't say - but what Sean somehow understood anyway, was that this was a sort of test. Jason would be watching to see how Sean would bring the boy to fulfillment and awaken him to one of the truly grand mysteries of a boy's life. And so, now here they were, having spent weeks preparing and with the culmination of their efforts just moments away.

"Well," Sean said, "Come in for a minute."

The boy stepped into Sean's room.

"I've had my enema," he said with a note of urgency.

"Good," Sean said. He could not suppress a smile at the boy's seriousness. "That'll help."

"And..." Randy said coyly, "feel down there."

Sean smiled and reached down to the boy's genitals. His tiny nuts weren't much bigger than pistachios. His cock was barely discernible.

"No..." Randy said with a grin and a blush. Nevertheless he couldn't help pressing himself against Sean's hand. "Back there."

"Ohhh," Sean said, and with his other hand twisted the boy around while the first hand released the immature genitals and slid around to the boy's shorts-covered bottom. One globe easily fit on Sean's hand. As his fingers explored the cleft between the boy's two luscious globes, he felt a protruding object.

"It's the sixth one..." Randy said with a note of pride. "A full inch across...and I've had it in all day."

When Randy and Jason had first knocked on Sean's door nearly three weeks ago now, Sean was almost as nervous as Randy was now.

"Sean, you know Randy."

"Of course." Just that acknowledgement alone made the boy beam, and when Sean added playfully, "I've had my eye on you, young man," Randy blushed deeply.

"Well," Jason continued, "Randy's been here for almost 10 months, and he's become quite skilled at so much of sex...but there's still one thing that he's dreaming about."

Randy looked up at Jason.

"Go on," Jason urged the boy, "Tell him."

"I..." the sexual neophyte reddened slightly and dipped his head, shyly. "I want to be fucked."

He looked quickly up at Sean. For his part, the older boy had known this was coming, of course, from his discussions with Jason, but suddenly he felt all the burdens of responsibility to make this a wonderful and fulfilling experience for the young boy. At every step of the process, he'd be consulting with Jason, but in the end, it would be entirely up to him to give the boy what he so desperately wanted.

"And..." Jason was saying, prompting the little boy.

Again Randy blushed delightfully as he added, "And, I want you to do it."

Sean flashed a quick glance at Jason. It would be impossible to refuse this beautiful child. He reached down and took the boy by the hand and together they moved to Sean's bed. Sean sat, and gently tapped on the bed beside him. Randy sat as well.

Jason watched for a moment, smiling in the knowledge that Sean would give this boy everything he, himself, could have and perhaps even more. His protégé would treat the youngster with kindness, and gentleness, and respect.

"That's kind of an important thing, I think, Randy. I'm very, very pleased that you'd want me to be your partner for this." He patted the boy on his bare leg. His skin was smooth as polished marble, and soft and warm as a cuddly puppy. "So...you really want to do this, huh?"

Randy nodded. His eyes widened; he actually seemed in awe of Sean.

"I think there are some things we need to be sure of, first, don't you?"

"Yeah," Randy dared to breath. "'Cuz I'm really small back there, an'..." The boy reddened again. "...well...an' I bet you're really big."

Sean smiled, with another glance to Jason.

"I see you two have some things to work out," Jason said from the doorway. He shut the door, and the two boys were alone.

"Randy," Sean said, turning to his young pupil, "sounds like you've got something on your mind."

Randy's almost black eyes shot down to Sean's crotch. The little boy actually licked his lips, and then he looked quickly back up to Sean's deep blue eyes and their hypnotic gaze. "Can I?" he breathed.

"Can you what, Randy?"

The boy blushed delightfully. "Ummm...see your...um...your cock...er...penis, I mean."

Sean smiled at the boy's intensity, but also at the echo of Jason's instruction to the boys to always use the proper terminology.

"Well," Sean replied, "If you really want me to have sex with you, then I think we need to at least get to know each other, don't you?"


"Well, then, what do you want to know, first?"

Randy's eyes shot back down to Sean's lap, then back up to his eyes.

"Go ahead, then," Sean said, leaning back to make it easier for the child.

Tentatively, Randy reached out and tugged at Sean's shorts. Twisting around a little more, he started to pull more aggressively. Sean lifted and the shorts slid down. Randy grinned when he saw the thong. He'd heard other kids say Sean liked to wear thongs, but now he knew for himself, and he could already see that Sean, even soft, was big.

Greedily now, Randy reached for the thong, drew it downward, and in an instant exposed the youth's nakedness.

Sean's penis was already growing, and now Randy's soft, but aggressive handling was rapidly increasing the organ's rate of change. In a flash, one of the boy's hands cupped the pendulous balls hidden in the dark, wrinkled sac. With his other hand, he gently grasped Sean's cock at the base. Sean could not help but grin as his young friend eyed his penis with what could only be described as pure lust.

As Sean watched, the boy licked his lips and lowered his delicate mouth to the object of his attention. The boy lodged the hardening cock head in his mouth and then assaulted the rim of the glans with his tongue. Immediately, Sean sucked in a breath, astounded that the 12-year-old could be so lascivious - and so good.

In the next instant, Randy was taking in even more of him, and unbelievably, in just seconds had swallowed nearly half of his adult-sized cock. Sean had indeed "had his eye" on the boy for some time, but as was typical, the littler kids tended to hang out with other little kids. Somewhere, this little boy had acquired truly prodigious skills as a cocksucker.

Sean glanced down at the boy who was working so hard to do it just right. It was almost as if his jaw had dislocated to accommodate him. His thin little red lips were stretched even thinner, and his delicate cheeks hollowed out, testifying to the strong seal around his penis. Now Randy backed off enough to take in a breath, and then went back down. The boy's throat contracted and loosened around Sean's cock, and Sean felt himself growing to his full length and breadth, but still Randy held him, and then began in earnest to bob up and down like an oil derrick.

"Whoa...whoa...Randy," Sean breathed, summoning all the will-power he had and placing a hand on the boy's thick soft hair. "If you want to see me hard, you better pull off, 'cusp if you keep that up, I'll blow my wad, and shrink back to nothing." Sean knew that wasn't exactly true. He might shoot off, no, he WOULD shoot off, but with that kid's action, he'd probably stay hard as an iron pipe.

Reluctantly, Randy pulled off, staring at what he had created.

"Wow!" the little boy said unabashedly. "You are big."

"Seven inches, the last time Jason measured."

"Seven..." Randy paused, and glanced quickly down at his own shorts. Sean thought back to when he first came to the island and knew exactly what Randy was thinking. After a moment, Sean realized that Randy was waiting for him.

"Can I finish you off? Please?" the boy pleaded.

"How can I say no, Randy? You are such a great cocksucker. Do you know that?"

The boy looked suddenly shy again. Great dimples appeared on either side of that wonderful mouth.

"Really?" he asked.

"Randy, my man," Sean said seriously. "You are the best." He stroked the back of the young boy's neck. The skin was satiny soft and warm.

Randy reddened, truly humbled by the praise. He looked up, anticipating.

Sean smiled and nodded. "Go ahead," he said softly. "You, know of course, that I'll cum in no time, the way you go down on a cock. Is that okay?"

"Mmmm," the boy nodded. "You..." Again that shyness returned. It was endearing, and drew Sean closer to the boy's heart every time. He continued to play his fingers over the boy's neck and shoulders.

"It's okay, Randy, you can say anything on your mind when you're with me. Anything." Sean heard those words coming out of his mouth, and he had to smile. Suddenly he was in a different place...well, a different time, at least. Those words triggered a memory: He was the little boy, and the words had come from Jason's mouth. Now his smile faded, and he understood the importance of what he was going to be doing with the young, hungry boy before him. In a way, it seemed as if the cycle of the island had suddenly been completed. Sean was about to give to this boy what Jason had given to him. Every boy had come to the island desperately needy in some way. And miraculously, when each left, they had been reborn. Some were now in their late twenties, and were by every measure, successful human beings. The island - and Jason - had changed so many lives for the better. Now a wave of uncertainty flooded over Sean. Would he, he wondered, ever be able to give this small, needy boy, what his mentor had given him?

In the years he'd been on the island, he'd become confident, sure, gentle, caring, trusting, and yes, even loving. It embarrassed him sometimes, but he knew that he was one of the leaders among the residents of the island; even the adults seemed to defer to him. But it was because of the island - and Jason, of course...always Jason - that he was who he was today. That moment in that dark, vile alleyway (which now seemed a lifetime away) was a special moment in time, and Sean had come to believe something divine had been in that moment. He chose to believe that, that for some reason somehow he'd been in the divine spotlight in that moment. It was as if his life had been in the balance...teetering at a critical point and it could have tipped in any number of directions. But with Jason's arrival at just that moment, his life had tipped in this direction...and he could not imagine any life more perfect.

A little boy's voice refocused him, and he looked down at Randy who was smiling almost girlishly. "You taste good - even without your semen. I can hardly wait."

"Well...me, too, pup." Sean replied, and tickled the boy in the ribs.

The boy grinned and launched himself back onto Sean's cock. In no time at all, little Randy was bobbing up and down, reveling in the hard member he worked on in his mouth.

Sean was almost beyond caring. The child's mouth and throat were incredible. Using every technique known to men, the boy pulled, squeezed, stroked, sucked, tongued, flicked, and blew. Randy seemed to know as soon as Sean did, that the man's balls were about to explode. The boy pulled back and with a wild fluttering action with his tongue, went to work on Sean's glans. It was the trigger. A groan of pure ecstasy wrenched from Sean's throat as bolt after bolt of thick, rich juice rocketed into Randy's mouth. The kid took all of it and the only indication of any trouble whatsoever was the slightest moistening of his eyes.

When it was over, Sean settled back onto the bed, and slowly Randy eased his action. Reluctantly, he released the big meat from his mouth, and grinning shyly, looked up at Sean. "You cum so much. I couldn't swallow fast enough...and..." He looked up as Sean's nodding urged him to continue. "...well, I really couldn't think about how good it tastes.

Sean smiled at his new best little friend. "Oh, Randy...Man, you wore me out."

Randy grinned, proud of his hard work, thrilled that he was with someone he idealized, and pleased that he was so appreciated. The young man dropped his head back on the bed, and he felt the boy lay down next to him. He felt Randy slowly let go of his penis. The boy's soft, delicate hand rested on his groin.

Sean reached down and stroked the scruff of the boy's neck. His fingers entwined in the ends of the smooth hair and traced along the creases where his little ears joined his scalp. He was rewarded with little shivers of pleasure he felt coming from the boy.

"Hey," Sean said softly, "come up here." Sean patted his chest, and in a flash the little boy was sitting on a gently heaving set of nipples. The child looked down and smiled. Sean's hands moved across the boy's shirt, down his arms, back up again, down along his sides, down past his little shorts, down to his legs. The boy's shyness returned.

Slowly, always looking for any uncertainty, Sean lifted the shirt off the boy. The twelve year old was perfectly proportioned - lean, sinewy, all muscle, but slim, and as Sean could now feel, indescribably smooth.

"Here," Sean whispered. "Shift around a little." He guided the boy so he was lying, his full length on top of Sean. With his soft, shiny hair pressed up against Sean's chin, the boy's thighs fell naturally on either side of Sean's cock. The boy realized that too, and squeezed his legs together around the meat.

"Hey," Sean said, tickling the boy. "What d'you think you're doing?" He was rewarded with a high-pitched giggle that was nothing less than a squeal of pure boyish delight.

"It feels great," Sean said gently, but your shorts are a little scratchy on my skin.

Sean felt the shivers of laughter cease, and Randy lay motionless. Sean's hands slid down to the boy's hips.

"Is it okay to take care of that?" Sean asked quietly. Randy was still; Sean could almost feel him thinking. Sean remembered all too well the feelings of little boys when they around bigger boys. Those feelings all centered in their groins, and Sean knew this was a crucial time in their budding relationship. He would not look at Randy's naked body until the boy wanted him to, but he wanted to feel his body - skin to skin - and as much of it as possible.

Slowly Sean felt him nod the slightest nod. "Okay," the boy whispered with a note of uncertainty.

Randy had just taken a big step in building the all-important trust that would have to exist between them if this task was to be a rewarding one for both of them.

"Lift," Sean whispered in the boy's dark hair. Randy lifted his butt, and Sean instantly slipped his thumbs around the waistband and in a slow, deliberate movement, slid the shorts down. The boy wore no underpants. In a few more moments, Randy had kicked the shorts off his legs.

Sean could feel the tiny pin-point nipples pressed against him. He could also feel an outcropping lower down pressing into his belly. Sean smiled gently as he savored the feeling of a tiny cock growing harder as it was pressed between two bodies. With one hand, he cradled Randy's head, holding it against his chin and neck. His other hand, in the lightest of touches, explored Randy's shoulders, back and finally, butt. The youth marveled at the exquisite smoothness of an unblemished body - and its heat. His one hand, opened wide, nearly covered the boy's ass. As he stroked the skin, the boy pressed up against him, bringing another smile to both of them.

Randy seemed completely relaxed. And he was; he was especially relieved that Sean hadn't demanded to examine him. The truth was he was a little embarrassed by his tiny organs, even though Jason had explained it was simply the way nature worked.

The boy reached down with his own hands and, squeezing underneath Sean's, pulled his ass cheeks apart.

"You want to feel my hole?"

Sean smiled. The boy was trying so hard to please...and, Sean did not fail to detect - was so desperate to get on with the task.

"Sure," Sean said casually.

Slowly, he dipped his middle finger down along the boy's cleft. As he did so, Randy let his cheeks return to their natural state, enfolding Sean's finger. The youth reveled in the warmth. Slowly, ever so slowly, Sean let his finger settle over the tiny pucker. It was hardly a pucker at all, since it, too, was smooth and soft. Only the slightest depression hinted at its location. But Sean had other signals that he had found it. Randy sighed and his whole body quaked. How am I ever going to enter him, Sean wondered, without tearing him apart?

Sean pressed gently down on the spot. A soft "mmmm" drifted from the boy's mouth.

"You want to put it in?" Randy asked anxiously.

"Randy," Sean began, conscious of the boy's desire to please and not wishing to make the boy feel uncertain about anything. "Let's talk, for a little bit, okay?"

"All right."

Sean let his hands wander up to the boy's hips. He felt the tiny penis pulse once. Gently he lifted the boy so eventually he was kneeling, straddling Sean's chest. The immature genitals were just inches from Sean's face, but the young man kept his eyes on the boy's luscious face. The countenance showed the uncertainty he'd heard in the boy's question. The boy was afraid he was going to be rejected by the youth he idealized.

"First, Randy," Sean began. "I really want to fuck you."

Instantly, any look of doubt faded and a great, unchecked smile spread across the boy's face. But almost instantly, another look of doubt spoiled the joy in the boy's eyes as he processed the man's words.

"But," Randy said uncertainly.

"But, if I were to try that today, it would hurt you so bad, and I'd feel really terrible, and you might even end up in the infirmary."

Randy's eyes widened. "Why?"

Sean grinned. "And I thought you were a smart kid," he said poking him between the ribs, bringing laughter from the boy. "Here." Sean took Randy's right hand and led it down to the boy's bottom. "Stick your finger up your asshole."

Randy looked momentarily shy, and then attempted to comply. Even with his tiny finger, he winced.

"Okay, you know how that feels. Keep it there." Reaching for Randy's left hand, he led him back to his massive, throbbing hard on. Randy grasped it and held it firmly as it pulsed in his hand. "Okay, genius, you figure it out."

"I'm too small." The tone of disappointment almost brought tears to Sean's eyes.

"That's tight...er...right." Sean grinned at his intentional mistake and hoped Randy would respond to the humor, but this was obviously too serious for the boy. "Randy," Sean continued. "You are too tight. Right now, today, you are too tight." He carefully avoided the word, "small."

He could see the boy thinking. Finally Randy looked into his eyes. "Today?"

Sean grinned. "You really want to do this, don't you?" He watched as some of the boy's anticipation returned.

"Yeah," Randy breathed, daring again to hope.

"Are you willing to work to get yourself ready?"

The boy nodded enthusiastically. "Anything."

"Okay, then. I'm sure you've heard Jason say sex is like anything. You have to start from the beginning. You also have to get yourself ready in other ways...like exercising."


"Right. We're going to slowly get your beautiful bottom ready for me."


"Have you had anything in there ever?"

Randy reddened. "My finger...." Sean could see the boy wanted to say more. He waited. "...and a pen once. An' it's easier with KY."

Sean smiled. "Yes it is...and it will be easier if we help you learn how to stretch down there."

"Can we start now!" the suddenly re-energized boy exclaimed.

"I think I want to talk with Jason, first. See if he has any ideas. How about tomorrow?"

"Tomorrow!" Randy said, sounding as if it were two years away.

"Yes, tomorrow," Sean said, suddenly breaking into a bout of tickling. The boy was beside himself. Sean's hands moved everywhere, tickling, touching, sensitizing. The boy bucked and swayed and twisted as if he were on a bucking bronco. With peals of laughter coming almost non-stop from the boy, he was having trouble catching his breath. The two boys' eyes had locked onto each other, and Sean could see the transformation happening...changing from sheer exuberant boy-fun, to something else, something bordering on lust. So he was prepared when Randy almost violently thrust his body forward, pressing his genitals into his mentor's mouth. Sean took all of him immediately - cock and balls. The rigid little penis was barely two and a half inches. Sean's tongue went to work immediately.

The boy, straddling Sean's chest, arched his back and thrust his head back in abandon. Randy's eyes widened and to keep from falling, pressed both his hands on Sean's head. He panted rapidly, and his body glistened with sweat. Every muscle was stretched taut. With a squeal, an almost endless series of tiny shudders spread throughout his body from his cock. As is often the case with properly aroused little boys, Randy's dry orgasm seemed capable of going on forever. The little penis stretched and pulsed up and down inside Sean's mouth. It seemed to be a little pump handle that pumped the orgasm throughout the little boy's entire body.

Finally, when the shudders weakened, the boy's body eased its incredible straining.

"Oh...h....h..." Randy seemed barely conscious of where he was. Slowly Sean let the tiny sac and balls and cock ease from his mouth. He gently slid the boy back and stretched him out so he was again laying his full length on top of him. Almost without thinking, Randy cuddled against his mentor's body and fell into a restful sleep. Sean smiled.


At their second session, Randy was like a child possessed. Whatever was required, he was ready.

Sean was sitting on the bed, waiting for him, when the boy arrived. A box sat on the bed next to him.

Randy, always the observant one, glanced down at the bed.

"What's in the box?"

Sean smiled. "All in good time, Randy."

"Did you talk to Jason?" the boy asked with an unmistakable sense of urgency.

"Mhmm, I did."


"Well...basically, it's like I said...one step at a time...ready to start?"


"Okay, well, get over here, then. What're you waiting for?" Sean grinned.

The boy was standing between Sean's legs in a flash.

"I want you to get used to being naked with me," Sean explained, "Okay?"

The boy nodded.

Slowly Sean began what would become a ritual undressing. He first removed the boy's shirt. Then he stopped.

"Here's what I see," Sean said to the boy. "I see a handsome boy, about 4 feet, 4 inches tall. 85 pounds. "

"Five and a half inches, 87 pounds." Randy corrected.

"Five and a half, 87 pounds." Sean said with a smile. "His beautiful hair is jet black, smooth, not too long, though long enough to hang a bit over two inviting ears." Sean's hands brushed gently up under the hair and around the ears. A little shiver waved across the boy's body. "The hair is shiny and healthy...like the boy's dark eyes." Sean leaned in, and gently kissed each eyelid as they fluttered shut.

"The boy's skin is as smooth and soft as the finest satin, and warm. It is dark from the sun's magic, and I could explore it forever." Here Sean leaned in a lightly kissed the boy's shoulder. "The skin covers incredible muscles, and I can see..." Sean gently turned the boy around, before continuing, "only hints of the bones that form his perfect skeleton." For fully six minutes, Sean's fingers and lips delicately explored the boy's upper body. At first, Randy grinned self-consciously, clearly unused to all the attention he was getting. With Sean's initial touches, he giggled, but then, as his arousal became more advanced, his responses grew more...serious. Sean's hands explored without reservation: the soft, beautiful face, starting with the wisps of eyebrows, the tiny button nose, the soft cheeks, the little valley that ran from the nose down to the center of his upper lip. Everywhere was deliciously smooth. The lips, full and soft. The teeth, visible with the smile. The strong, muscled neck sweeping down to broad, straight shoulders. There Sean felt the first real evidence of bone, and he allowed his fingers to trace back along each shoulder blade. The fingers continued out along each arm and back again.

For his part, Randy understood - and felt - that something was different here. He certainly been aroused before since being on the island; in fact, he'd gotten off countless times, but this wasn't like those times. Before it was like a switch being turned on - off one moment, fully aroused and ready for sex the next. Now, it was if his arousal were controlled by a dimmer, not a switch. Slowly, he was being brought to life, and someone else - his mentor - was making the adjustments. The boy's skin seemed to come alive as Sean's hands did their work - and that was just one indicator of dimmer being slowly cranked up more.

When Sean's hands reached the boy's tiny nipples, they instantly rose like nail points. Sean could see the change in the boy. His breathing changed, becoming more shallow and faster.

As Jason monitored the activity from his office, his heart surged with pride. Sean was being so gentle, so thorough; he was committed to fulfilling Randy's wishes. If the boy were truly aroused, his body would automatically be more receptive, not to mention the boy was learning that unhurried, unchecked sex could lead to a very different experience than the less "finessed" sex he'd shared with other boys on the island.

In addition, an undeniable bond of trust was growing between Sean and Randy with each passing moment.

As Sean played with the tiny nips, a quiet whimper escaped from the boy's throat. It was more a sigh. Then Sean moved onto the muscled tummy. His finger explored the slightly indented navel, and then his hands drifted around to the boys back and rested momentarily on each side of his rib cage. He could feel the boy's excited breathing. All the while he'd been describing what he was seeing and feeling to the boy in words barely above a whisper.

Now Sean eased his hands down to the boy's shorts. He let his hands slip in behind and they felt the smooth firmness of the boy's two perfect globes. They were smooth beyond imagining and muscled.

Withdrawing his hands, he grasped the cloth and lowered the pants to the floor. Randy, without prompting, stepped out of them, then realizing he was naked before the youth, he dropped his gaze downward.

"Hey..." Sean said gently. "Suddenly a little shy, huh?"

A small smile formed on the boy's face. "I see..." Sean began, then paused and gently lifted the boy's chin to bring each of their gazes to the other's. There was a note of uncertainly in the younger boy's expression. "I see...the most perfect boy I could imagine. The gods of ancient Greece could not have created a more perfect boy."

Randy glowed with that special sense of self-worth that only comes when one person begins to bring true and profound pleasure to another.

Again, Sean's hands moved back to the boy's sweet bottom, then shifting himself off the bed, he knelt before Randy, making the boy feel even more like a creation of the gods. Sean's hands moved down the child's legs. Here he found the very slightest hint of the softest down.

Then, never hurrying, he worked his fingers back to the tiny sac. Gently he stroked and stretched and probed. The two small marbles inside felt smooth and firm. He could feel the structures of tubes leading back into the boy's body. And again, all the time, describing everything.

"Ahh...now for the penis. Perfection. Rigid, outstretched. Circumcised to show the proud pink head: the smoothest skin anywhere on a boy's body. I would think it a statue, if it weren't for the gentle pulsing of this beautiful organ. It is lifting up to an angle almost straight up." Sean looked up to the boy's eyes, like two black holes, pulling everything within their field of view into them. Randy smiled a relaxed smile, and as Sean reached out with the backs of his fingers, and drew them across the boy's member.

Randy's entire body became rigid as if it were an extension of the tiny prick, and he sucked in a violent breath, followed by a rapid series of shorter breaths. Now Sean grasped the organ with his thumb and forefinger and began to masturbate the little boy, and he could tell Randy would soon be climaxing.

With both boys holding the other in their gaze, the younger boy suddenly gave in to the building pressure. It was an orgasm that had no rival in his short life. As Jason watched on the closed circuit TV, he thought if the boy were producing semen, it would have shot across the room.

Sean continued his action, though now he slipped a few fingers and his thumb around the penis. Shudder and shudder of orgiastic energy flowed through the boy. Finally, when he had no more energy to release, he began to sway, and teeter. He reached out to steady himself, and Sean, in one move, swept him up in his arms and laid him out on the bed.

While the boy rested, Sean stripped. The efforts he had expended on the boy had also had their effect on him. His cock was seven inches of iron. Carefully, he straddled the boy, who was lying on his back, stretched out fully, and completely relaxed.

"Thank you," the little boy squeaked, the words catching in his throat. It seemed to take an effort to put two thoughts together. He smiled when he realized Sean was naked and kneeling above him. With effort, he lifted his head and gazed at the youth's pulsing organ. He reached down to grasp it.

Sean smiled at his little friend. "Not today, Randy. This is all about you, today." Slowly the little boy let his arm fall easily at his naked side. He sighed a long slow sigh of utter contentment.

"Think you can roll over for me?" Sean asked as he moved backward slightly, back toward the boy's out-stretched feet.

"Yeah," Randy said dreamily.

"Okay, then." Sean reached down to help the boy roll over.

What perfection. Slim, but firmly muscled arms and legs, endless, smooth, richly tanned skin from the exquisite ears to the delightful little toes. Virtually hairless. His torso tapered nicely from his shoulders to his waist even at this tender age. His hips widened slightly to provide the foundation for two incredible mounds of boy butt.

Sean glanced up to Randy's head. The boy had twisted it so he rested on his right cheek. His eyes remained closed.

"Okay, Randy, I'm just going to explore a little bit. All right?"

"Mmmm-hmm," came the barely audible reply.

Gently, Sean let his hands rest on the sides of the boy's rib cage. As if giving artificial respiration in slow motion, Sean felt the rib cage compress ever-so-slightly, then slowly expand once more.

How, thought the older boy, can such a simple thing be so arousing? The sense of touch is an incredible thing. In that instant, he thought he'd rather be blind or deaf than lose his sense of touch.

Working to keep from trembling, Sean drew his fingers downward toward the object of his exploration. The little boy was motionless, save for his breathing.

When Sean's hands came to rest just above the boy's hips, he realized with little effort he could stretch his hands and almost encircle the boy's slim waist. But he decided he should continue on. And with utmost delicacy, his hands found the two small hillocks rising invitingly above the small of the boy's back. Almost imperceptibly they flexed at his touch.

"Just try to relax, Randy," Sean urged gently. Jason had suggested that the best way to begin his work would be to get the boy completely relaxed. And both Jason and Sean knew the best way to completely relax a boy was to bring him to the absolute zenith of orgasm. Sean was confident he had done just that. And now the soft, relaxed muscle within the mounds of the boy's ass proved he was right.

Slowly, Sean's right hand shifted so that he could, with just one hand, spread the two cheeks. It took little effort to accomplish that. As they parted, a pure, tiny, pink indent was revealed. Sean gazed at it in awe. His first thought was that he could do nothing to violate that incredible entrance. It showed no signs of use. Virginal. And although what he was about to do was something he never found especially appealing, suddenly he had an almost overwhelming urge.

He lowered his face so that his nose brushed against the stretched cheeks and he breathed in a surprisingly sweet fragrance. Tilting his head up brought his lips to the pinkness centered between the mounds. He had to purse his lips together to make them small enough to seal the space around the tight little entrance. He closed his eyes and kissed the spot that drew him like a magnet.

That first thought - that he couldn't do damage to such a virginal place - now gave way to another. He wanted in this moment to be joined with the boy at this place of sublime perfection. It was a drive that would build over the next two weeks, as together they prepared the initiate for his deflowering.

When his lips first touched that soft, but firm rim of muscle, the boy's body instinctively pulled in, attempting to clamp the entrance even tighter. Sean lifted away and smiled, surprised at the gentle taste left on his lips.

He glanced up to find that the boy had opened his eyes and was gazing down at him.

"You going to do it now?" he asked breathlessly.

Sean smiled. "No, Randy. It's going to take a couple of weeks to get you ready."

"Two weeks!"

"That's what Jason seemed to think."

"But why?"

"We need to get your bottom used to stretching. Here." Sean shifted his position so he could reach the drawer of the bedside table. He removed some KY. He glanced up at Randy and the boy grinned lewdly.

Quickly, Sean squeezed some gel onto his fingers. He rubbed the cool stuff around on his fingertips until it had warmed, then he carefully moved to the cleft between the twin hillocks. Again he spread them. Randy twisted to watch as best he could. Then Sean gently began a slow massage of the boy's entrance. He made no attempt to enter; he simply lathered the area completely with gel.

Randy's breathing had momentarily quickened, but as Sean gently ran his fingers around and over the spot, the breathing slowed.

"How's that feel?" Sean asked.

"Nice," the black-haired beauty sighed.

"Good. You're pretty relaxed down there, Randy, so let's see if you can stay that way...You ready?"

The boy nodded.


Under his middle digit, Sean felt the little pucker adjust itself and then gently roll open.

"Pffft." A tiny fart emerged from the boy and bubbled up through the KY.

"Oops!" Randy said and reddened. "I'm...sorry!" Sean could hear the doubt that suddenly filled the boy's voice. He tried so hard to do things perfectly.

"Hey," Sean said, looking directly into the boy's beautiful eyes, "that's okay. It's perfectly natural, and it'll happen more than once while we're giving this little thing the attention it's looking for." Sean grinned at the boy and suddenly, seeing the vulnerability in the boy's face, leaned up to the boy's face and brought his lips to the boy's lips. The kiss was light and fleeting, and that only made Sean want more. After a brief break, his kissed him again, pausing momentarily to draw his soft lower lip in between his teeth.

"You're wonderful, Randy. You really are."

Sean lifted up slightly and stared down at the boy beneath him. His hand continued to work over the pucker.

"Ready to try it again?"

The boy stared into Sean's eyes and nodded.

"Okay...I'll wait until I feel you really relaxed."

Again Sean felt the tiny muscled opening spasm, then after a moment, miraculously open. The youth was ready and gently pressed his fingertip into the opening. Instantly it clamped shut again, and the boy winced.

"Does it hurt?" Sean asked.

Randy breathed short shallow breaths. "A little...but...nah...mostly...it...just...feels different."

Sean knew the boy was a bit uncomfortable - not necessarily physically, but from the newness of what he was experiencing.

With his fingertip just barely resting within the rim, Sean spoke again. "We'll just rest for a minute." Neither moved, and slowly, Sean felt the tight ring begin to relax.

"Want to try more," Sean asked after another minute had passed.

"Okay," Randy said, though not without a little doubt in his tone.

"All right, Randy."

In the next instant, Sean pressed his finger in further. Again, instinctively, the asshole clamped shut. His finger was in to the first knuckle. When he had pushed it in, Randy's whole body responded, as if trying to help the sphincter clamp down and squeeze out the intruder. Randy was panting quickly now, almost like a woman in labor. Sean knew the boy was probably feeling some discomfort now, and he let the mounds close in to surround his impaled hand.

"I know it feels...strange," Sean whispered. Randy, the brave little hero, trembled at the new sensation - a tightness that hinted at the discomfort that would come with larger objects. "It's okay," Sean said and leaned down beside the boy. As carefully as possible, he lifted the child over him, and together, they lay like that, holding each other, eyes locked on the other.

Sean understood this was the first step of a journey that would lead to the goal the boy had set for himself, and remembering his own journey, Sean understood the feelings that now overwhelmed the boy. "I know, Randy, it's okay. I have to leave it in there if you really want to do this. Okay?"

Between his panting, the boy whispered, "okay."

"Should I take it out?" Sean asked, wanting to be sure the boy knew he had a choice.

A few more pants, then "No."

"Okay, Randy. Just try to relax. It will get better soon. You'll see."

With his free hand, Sean rubbed the boy's warm, smooth bottom, the way a mother would soothe a child. Slowly, Randy's breathing eased. Sean had been feeling small contractions in the rim of the boy's pucker all along. Now they eased, too.

"It's...it's okay now," Randy said finally, and there was just a hint of pride in his tone.

"I'm glad," Sean said.

"You can put more in," the boy said tentatively.

Sean smiled. "You're a pretty brave kid. I'm impressed."

Randy smiled in response, pleased that his mentor would say that.

"But," continued Sean, "I think I'll just leave it this way and let you get used to the feeling down there."

They pressed against each other for another five minutes. Then, gently, Sean moved his buried finger just slightly. The sphincter clamped shut, and another wave of uncertainly flowed across the boy's face. This time when the muscle tried to push the foreign body out, Sean allowed it to. After two spasms, his finger popped free.

"There, Randy," Sean said. "Almost done for today." He leaned down and kissed the boy on the forehead. He thought about how dependent the boy had become on him - how trusting he'd become. His determination was astounding.

"How did that feel?"

"It kind'a hurt when you wiggled your finger, but it's okay now."

"Want to try something else?"

"Like what?"

"Well, first, roll over." Randy complied and in a flash was on his back. Only then did Sean see that his little prick was as hard as a poker. The youth brushed across it with his hand. "When did that get stiff?"

A look of confusion spread across the boy's face. "I think it started when you first stuck it in. It felt so...full...and my penis seemed like it was going to explode. That's why I didn't want you to take it out."

Sean smiled.

Then the boy asked, "What are we gonna do now?"

"Well, there are a lot of positions for fucking..."


"Yeah. For instance, the most common ones are, you can be laying down on your tummy, sort'a like you just were...or...you can be laying on your back...or we can sort of spoon together - you can be on your side, and I can sort of snuggle up behind you." Randy's mind raced as he pictured each position as Sean described it. "Which one do you think you'd like when we do it?"

With the words, "do it," Randy's eyes flashed with a look of forbidden pleasures.

"It kind of makes me feel...better...when I can look at you, and it was kind of hard the way we were just now. I think on my back."

Sean smiled as he knelt on the bed between the boy's legs. "Good choice, Randy. Okay, then, here's the position." He reached out and grasped Randy's legs just below the knees. He thought about the hundreds of times over the years, Jason had helped him into that same position as he gently bent the little boy's legs at the knee, folding the lower legs up against the backs of the boy's upper legs, then folding them at the groin backward and out. The effect was to expose the boy's gel-covered asshole again.

Sean lifted the boy up at the waist, pulled him toward him, and then let the small, tight butt settle down in his lap. Randy's bottom, splayed wide open, pressed against Sean's testicles, and Sean's pulsing cock, dripping with pre-cum, was thrust up beside the boy's tiny one.

"Now..." Sean began, "how far out can you open your legs?"

"Like this?" the boy asked as he moved his folded legs out on both sides.

"That's good," Sean said. "Another way is like this." Again Sean took the boy's legs and unfolded them, then lifted them up to hook over his shoulders.

Randy pressed against Sean's upper body with his legs and grinned. "I like this way," he breathed.

"So do I," Sean said and smiled. "Your skin is sooooo incredible and smooth." Sean ran his hands along both of the boy's legs and Randy grin stretched every bit as much as his bottom.

"Are we done?"

"Not quite. One more thing." Sean reached for the box beside them on the bed. He opened the lid, reached in and removed a three-inch long, smooth plastic rod about 3/8" in diameter, the size of Sean's baby finger. It was flexible and at one end had a slightly larger rounded bulb. At the other, there was a kind of long, narrow handle running perpendicular to the rod. The handle was slightly curved.

"What's that?" Randy asked, his eyes the size of saucers. Sean smiled, suspecting the boy could easily figure out its use.

"It's called a butt plug. See, there's a whole bunch of them." Sean lifted the box and showed Randy a half a dozen plugs of various diameters, the biggest being an inch and a quarter.

"You're going to put it in me!" There was an obvious sense of anticipation in Randy's question.

"Mhmm. Ready to try?"


Sean carefully lathered the thing with KY.


Randy nodded.

Sean reached down, placed the bulb end against the boy's entrance.

"Okay, when you feel it press against you, you may want to push out gently."

"Push," the boy repeated. Almost instantly, Sean felt movement down there, and pressed. The bulb slipped in and Sean stopped with the plug about a quarter of the way in.

"Ahhh." Randy sucked in a breath.

"Does it hurt?"

"Just tight," the boy whispered, "A little bit."

They waited a moment, as Sean explained they had to get all of it inside the boy.

"All of it!" Randy said with amazement. "Will it fit?"

"Let's see," Sean said and smiled. "How's it feel now? Better?"

Randy nodded.

"Okay. See, your relaxing back there. Now we can try to get more in. Ready?"

"Uh-huh, I think so," Randy said with a note of excitement. He pushed out and Sean pressed the plug deeper.

"Ahh...I can feel it going in!" Randy squealed with delight.

"Does it hurt?"

"No!" The boy seemed barely able to catch his breath.

Sean kept sliding it in until the handle fit up against the boy's cleft.

"How does it feel?" Sean asked as he shifted his position and began to lift the boy's legs off him. Randy stretched out his full length with Sean kneeling next to him.

"Awesome...." the boy answered.

"I want you to keep it in you for as long as you can. Course take it out when you've got to go to the bathroom, then grease it up and put it back in. You want to try doing it yourself?"


Without any further instruction, Randy pulled his legs up and out. He reached down and grabbed the handle and pulled. All kinds of expression flooded across the boy's face as he felt the device sliding out of his asshole. He only winced slightly as the bulb met the resistance of his tight anal rim.

"Good, now try putting it back."

Randy, after taking a close look at the plug (and, like any small boy, taking a quick whiff), repositioned the tip at his hole. He had to try a couple of times to get it in the right place.

"Now..." Randy said aloud, as if reciting the instructions he'd gotten from his mentor, "...push."

Sean studied the boy's responses as he eased the plug back in. It seemed to slip in easier this time, and Sean marveled at the body's ability to adjust. It would be making a lot more adjustments in the coming weeks.

Randy's eyes grew wider as the full length of the plug rushed home. He sucked in a long breath as he felt it move deeper into him. Suddenly his body shuddered, his eyes lost their focus and his entire body became rigid, as wave after wave of orgasm washed across him.

Sean grinned when he realized what was happening, and without even thinking about it, let his hand drift down to his own shaft, soaked in his pre-cum, and began tugging on it. In the past, he'd been so busy bringing the boy off, that he hadn't been able to step away to view the wonder of the child's orgasm. It was amazing as it seemed to go on forever. Still, he felt a little cheated that he hadn't had a more active role.

Almost at the same time, Sean realized that this incredible beginning - the budding relationship - would be the last relationship he would be a part of on the island, at least for some time, perhaps even forever. And yet, the rewards were undeniable. Just these few sessions with Randy had given him so much. Now he felt a strange poignancy when realized he would probably not be present in the boy's life when he had matured enough to have his first wet orgasm. It made him a little sad. It would be incredible to be present when the boy ejaculated for the first time.

Jason had said as much. His mentor and lover had told him his relationship with this boy would be different - different from all the other times Jason had had sex with boys (and even a few girls) on the island. At first, he did not understand why that should be so, but now he did. It boiled down to just a few words: caring...responsibility. This was perhaps one of the great lessons of the island. This little boy was putting his trust in him - trusting him to guide him safely through a very special time in his life. This was about more than simply pleasuring each other. Oh, on one level, of course it was; sex is always about pleasuring one another, but Sean now felt the weight of caring for the small boy in the same way - Sean now realized - that Jason must have cared for him. He would protect the boy. For all these years, Jason had done the same thing for him, had felt the same thing for him. Sean was not just a partner now, he was a mentor - as Jason was mentor to him, and it made the 18-year-old feel a particular obligation to ensure Randy's sexual awakening would be something the boy would cherish for the rest of his life.

Sean smiled at this somewhat unexpected revelation. He now saw the legacy the island leaves for each of the boys who pass one of the most formative times of their lives here. A shudder passed through him. As the enormity of what Jason has accomplished here settled in on him as it had never done before, he felt truly humbled to be a part of it. It was an awesome responsibility, and tears welled up in his eyes as he understood just how much trust Jason had placed in him. He gazed back down at the boy. He'd been given a charge to care for this boy; it was nothing less than a sacred bond between the two. He felt a surge of genuine love - not lust - flood over him.

After several minutes of silent stillness passed, the boy stirred.

"Hey," Sean said softly, "It's time you get on your way, I think. See you tomorrow?"

"Yeah," the boy said dreamily. "But first I have to say thanks." He reached out, drew Sean down to him, and their lips lightly brushed against the other's sealing their unspoken vows to each other.