This is fiction, don't read this if you shouldn't legally be doing so but otherwise enjoy. Everything is consensual and fantasy in this story.

I love email!   royalredsheets@yahoo.com (royalredsheets@yahoo.com)

 

-Royal Red

 


Streaming Simon

 

 

(From the blog of "Spymaster34")

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Introduction

  

     I'm sure that by now, you and most of the internet know about my little... pet project. He's the adorable young boy whose sexy "secret" exploits have been getting leaked online for millions to see. I've gotten a lot of emails and requests to reveal the entire backstory of the operation. 

     Well, firstly I'm sorry to disappoint the conspiracy theorists who seem to think the most of this. There's no secret organization, no sinister ring. I'm one guy, responsible for it all. 

     I don't want to reveal too much, only that it all started simply. I was introduced to the house in question during a misadventure in job stress. Well, it's hard to explain. Thankfully, I've dug up my old blog posts to do the talking for me. Read and weep.

 

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Entry 1  

 

     Hi blog. I'm disgruntled.

     I've been called over to the east side of town for maintenance at least four days a week, for almost half a year. All I can say is: what a pain. The young Ms. Ashley Leighton is the owner of the estate I have to manage. She's a prolific "socialite", with a perfunctory modeling/acting career, well-bred and beautiful, bailed out of all her problems for all her life by her Fortune 500 family. Fuck her.

     Every time I show up, she always finds something ridiculous for me to do, claiming the fiber-optic setup "is getting slow again" or that it "occasionally cuts out". Her little brother probably just downloads too many movies, and there's nothing anyone can do about that. I learned after a week that just looking busy for an hour is good enough to "fix" all these imaginary problems - I just have to role-play a placebo. Then I walk around, pocket something nice and shake her dainty hand as I leave. Repeated theft is helping me live with my misogyny, and it took only a few weeks to learn the layout of the house as well as my own. 

     Now, any other a maintenance guy would just tell her there was nothing to do, and that would be that. But there's a reason I go back so often... To be honest, she is a beautiful girl. She has a slim tight body and looked like Katrina Bowden. So admiring her body is one thing, but that's not really what gets me visiting all the time...

     I drive back there, all those times, because of her kid brother! 

     Her brother... Simon Meyers Leighton. I just can't help staring at his tight body and those big green eyes. That boy got all the looks in his family, and he could steal any man from little miss Ashley in a heartbeat. Simon is this slender angel with cropped blonde hair, an infectious smile and a tight perky ass. He's blessed with fantastic genes for sexiness, and despite being clearly a boy Simon would fool anyone into thinking he was a girl if he really wanted to.   

     His sister though, holy shit. What a spoiled bitch. Does she really think she can talk to me like trash just because I work for a living? Surely there's a man who will set her straight... someday. It sure as hell won't be me, though. I have my eyes on Simon.

     I see Simon every visit when I pretend to fix the internet in his room. Well... his "room". The entire home is a palace, and that means even his "room" has two stories and a stairway. Simon's surround sound, giant HD monitor and TV screen are amazing. It's as much of a theatre as it is a bedroom, and the room got so decked out with media swag that the developers soundproofed his room. 

     Soundproofed... every visit I could simply close Simon's door and rape him for hours. I wouldn't hurt him, but oh yes I would rape him - I'd break him in before his prime, make him cum and cum, curl his toes and lose his mind. I'd make him scream and moan and beg for more at the top of his lungs, and nobody would hear a peep beyond his door while I fucked him raw inside. At least, I like to imagine I could do this.

     Instead, I chose the slow seduction.

     We talked a lot over the first weeks, about life, family, his interests. Simon had a charmed life, despite distant parents who just wanted him for a trophy. They certainly made it up to him and his sister with the full upper echelon perks. Turns out he's even been in a couple of blockbuster movies, with a small speaking part in an action movie and some other family movies with animals. He is certainly double-take-cute enough to play any Hollywood part. But whenever I probed subtly about sex, I could just tell he was the type to get filled up by a man... all of the signs were there alongside the obvious physical indicators. In time I got to know Simon better than his shallow sister Ashley knew him, and I did it just by giving the slightest sign of interest. 

     I had even earned enough of Simon's trust for him to sit in my lap, and I'd leave my hand on his skinny leg while we talked. From the first time I did that, it was all I needed to rouse an instant Simon stiffy. I'd trace a path along his inner thigh and just barely stroke my thumb along his balls, pleasuring him through the sheer fabric. I'd hold him tight and tease his ribs, his nipples. I knew how to make him moan. I'd talk into his ear too, whispering subtle sexual things and telling him he was beautiful. 

     At first I only did this once every few visits. But by now it's become part of the routine, and the petting gets heavier and heavier each time. Sometimes I do my delicate dance with his body for over an hour, letting all of my innocuous touches and breathy whispers build up until it brings him to the edge of orgasm... and then I keep him there. I let him recover a bit... then I bring him right back to that teetering helplessness. Again, and again. 

     Those are my favorite moments, when I get to hold his innocent sex completely at my mercy. I love watching him blush and stutter and try to hide his boner from me. He knows something was off, but he blames himself. In fact, Simon is always so pre-occupied trying to hide his wet stiffy, he doesn't even realize that I fully intend to cause it! 

     But dear god was that boy shy. I knew he was the type that would be clinging to you if you could worm your way in, but christ almighty he was just so shy. As soon as I left, I knew he would do nothing but sit at his computer - doing nothing - playing games he barely enjoyed and wasting his rare beauty. 

     The impasse was obvious - he would never let himself talk to me openly about sex until I eventually died of old age and boredom. I was manipulating him into feeling good, but I never hear him say a word about it. His feelings, his preferences. That made escalating my touches too risky. And trust me, I used all the tricks in the book, but I just wasn't the right guy and eventually I accepted the fact. He was raised on a culture fearing all things sex and "stranger danger".

     Pity that Simon had to be beautiful and an iron-clad vice at the same time. He would need a different approach, and well, that's why I put his entire life under surveillance. 

     It started simply - I just rigged his webcam at first. I installed remote access software to his desktop, and for almost a month I would see everything his trusted webcam saw. I learned that the boy slept naked and barely understood his own body. I learned his favorite underwear (a cute yellow Pikachu pair with a face on the front and a tail on the back). I learned how, whenever Simon was in school, his hot big sister liked to stuff herself with a vibrator while snuggled in his bed. She liked to squeal out for "Daddy". I recorded everything of value (some in a blackmail folder) and I was certain that Simon would one day share his sister's proclivities. Oh yeah, there'd be another Leighton screaming out for "Daddy" soon enough.

     Eventually, my web-peeping snowballed into more - Simon's whole house was state of the art, and that made my job so easy. I installed remote access to the TiVo, to the security panels, everything. And then I installed more cameras, microphones, the she-bang. I turned an innocent kid's sanctuary into a panopticon, where everything he did could be monitored at any time without his knowledge.

     I also rigged everything I could think of. His iPod, his laptop, desktop, TV. Any time he watched a show, listened to music, surfed the web, I would know exactly what he was seeing and hearing.

     And most importantly, the software let me control all the functions... its power was amazingly useful. Was he sleeping too late? I'd crank that alarm clock. Was he wearing too much? I would turn off the AC and watch him strip down to his sweaty young nakedness. All from a simple program on my laptop. 

     My favorite though? The "ass-cam". I bought a couple of novelty spy buttons, and sewed them into the seats of his pants. No way it wouldn't be fun to see the appreciative glances towards his bum. His clothes are even audio wired too - I would hear everything he said and heard.

     I was able to watch him from cameras everywhere, in the fancy glass doorknobs, the walls, the bathrooms, inside and outside the house. There were even underwater cameras in their pool - lots of them. As long as Simon was home, I could watch and hear him from at least four different angles at any given moment. I bugged his sister's cars for good measure - it would be useful to know where she was. 

     Yes this cost a lot, but I funded it easily with the fortune I lifted from their home. 






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Entry 2
 


     A few days ago, Simon woke up slowly, like he always did on a lazy summer morning. He was naked, like always, and he was erect. Uncircumcised. It was a normal day, but also his umpteenth to be watched remotely by a stranger - me. Simon yawned, stretched, and walked to the bathroom. A crusty path of precum trailed up his flat stomach, and even though he didn't notice that detail, his HD cameras sure did. 

     Simon walked over to the sink, brushed his teeth then stepped into the shower. There, another camera was rolling. The naked boy relieved his urine in the tub, like always, and like always his erection was still there after he finished. 

     Simon rubbed at his penis, grinding a finger along the head of it. His finger was slick with precum, so it didn't feel uncomfortable when he rubbed around his opening in constant, steady circles. It felt good... like always. 

     I, the maintenance man had visited again just the day before, and the boy always felt the urge to recreate my touches in the horny, confusing days after. He clearly didn't know how to masturbate. Simon touched his inner thigh, rubbing it. He traced a thumb over to his balls, and tried to tease it tenderly like I would do. He played with his nipples and ran a hand across his ribs.

     It wasn't the same - Simon didn't have my magic touch. I smiled, knowing he needed me. Simon got out of the shower, and dried up in his room. He stood in front of his full-length mirror and closed his eyes, touching his body again. Simon was hunched over like an awkward duckling, trying to enjoy these dirty feelings. A well-placed camera behind the mirror captured everything he did in real time.

     Simon was frustrated. The boy didn't have any idea what to do, but felt such a strong urge to do it. He went to his nightstand and took out a thermometer, dipped it in some vaseline, and placed it in his bum. He twisted it around, then went on touching himself in front of the mirror. The thermometer turned him on a lot. But he had no clue what he was doing. 

     Like all boys, he was fascinated with his young cock. But my goal was to steer him towards the deviant side of his curiosity... the one that drives boys like him to put thermometers in their bum. Simon wanted to recreate the naughty feelings he got from an innocent experience of penetration.

     But I was going to take it to another level... I was going to push him towards that dark side of boyhood, and mold him with those indecent feelings until they defined his sexual character.  I decided to let Simon continue on his own while I picked out a good porn file for his upcoming anal pleasure education.

     Once I found it, I turned on the TV and let my selected video interrupt Simon's moment. In the clip, a slim and gorgeous boy was playing with himself in front of a mirror, standing much like he was. Blushing, Simon's first reaction was to turn it off right away. He was afraid of getting caught, but I turned the TV back on and disabled his remote. This time Simon couldn't do anything about it, and he was very interested to see something very peculiar - the adorable boy on the TV wet one of his fingers... with his mouth! And slipped it into his pretty, pink asshole!

     Simon was intrigued, and after watching for a few minutes he tried it for himself. Meanwhile on TV the young teenager was graduating up to a dildo, and Simon heard the cameraman tell the boy to relax his muscles and push against the thick toy. Simon did this for his finger, and it felt exquisite. 

     "Mr. Lynde, it's so th-thick," cried out the slender child on TV. Simon repeated the boy's words, relishing in simply a finger. "Mr. Lynde, it's s-so thick!" 

     I laughed at the exchange. How ironic for a boy named Simon to be a mimicker. 'Simon Says', indeed.

     I queued up a few more videos of cute boys fingering themselves, and I made sure to filter all clips where they touched their dicks. If I play my cards right, Simon will know only what I want him to know, and he will never even learn to jack off for at least the next four years. It will be cruel, but exquisite - pure, refined and unadulterated thought control.

     Simon's going to think the only way to get off is by playing with his sensitive ass, and teasing his erogenous zones. A helpless horny lamb, this boy is only going to have orgasms if he plays by my rules. Bit by bit, I'll make his hotspot shift away from his penis to his bum. Eventually it will shape who he is, and his cock alone would never satisfy him. I'm going to train this little boy to develop a genuine anal fixation. 

     I even topped it off with some peer pressure. Just yesterday, I set up a fake IM name - petermaeb10 - and pretended to be a boy he met at the mall (got to love that audio clothes-wire). I told him that playing with his dick was bad! That this would make it grow smaller, and that it makes his future orgasms "feel less good". Simon believed it, especially after I tampered with a few google search results to twist the facts. "Playing with your penis stunts your growth!" My fake websites also claimed that anal orgasms caused boys to secrete a pheromone that made girls go crazy. 

     All of this false sex ed is ridiculous, of course, but naive little Simon just eats it all up. I'm filling his pretty young head with carefully selected half-truths and lies. And with the conservative school board in his district, I doubt he would ever learn about sex from public education.

     What a blessing this is, blog. I now have full control over Simon's self exploration. This was supposed to be a deeply private and individualistic process of innocent discovery... but instead I unlocked the forbidden reins to manipulate Simon's sexual development as I pleased. Even a parent doesn't have the kind of power I have, and Simon barely has real parents to begin with. He and his sister are crossed off boxes in life's checklist, left to their own devices.

     The shy boy has no real friends either. Turns out Simon is isolated by his wealth, and his rare petite beauty makes him a bully magnet - though I'm sure those boys all wanted to fuck him if they understood their own sexual feelings. I am in the perfect position to fill the emotional vacuum in Simon's life and mold him into a perfect and sensual boy.

    

 

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Entry 3



     Sorry guys, it's been a while!

     By the time of my maintenance visit... hrm, about the week after my last post, Simon was completely obsessed with fingering his hole. It was the closest thing he knew to real masturbation and every day Simon's skinny little fingers plowed his pink entrance with a frenzy.

     He often told his new confidant Petermaeb10 about the frustrating erotic agony, often describing the anal lust as a "hot, really deep itch" that he felt "all the time now". I let him know that it meant he was physically gifted... of course, if my plan falls into place his "gift" would involve a tight little present for my cock as well.

     As Petermaeb10, I also suggested he start wearing some... tighter clothing. While he was resistant to the idea at first, Simon eventually picked out some thin tight tops and shorts from his expansive walk-in closet.

     Better yet, it was obvious that Simon enjoyed it. My erection almost tore itself from my jeans when I saw the boy reach under his tight half-thigh shorts and finger himself under the fabric. He sat down impaled on a finger, typing with only one hand... what a hornball.

     When I sent him messages asking if he felt "hot n sexy", I saw little Simon blush and giggle before typing yes. I asked him for pictures, and to my surprise he actually sent them! Simon must have had a bit of a boy-crush on his new cyber friend.

   

     Petermaeb10:    woww you look relli relli smokin... lol

     Simonatorzz:     lol... thanks peter :)

     Petermaeb10:    you should dress like this all the time...

     Petermaeb10:    i bet it would make you feel soo horny 

     Petermaeb10:    wouldnt that be cool?

     Simonatorzz:     idk, i think it would be embarassing >.>

     Petermaeb10:    but that's the point lol, plus...

     Petermaeb10:    nobody else knows how sexy you feel, only you do

     Simonatorzz:     you mean, only you and me ;)

 

     It was official - Simon Leighton had a crush on my fake internet boy. And I was going to see how far I could push him. Being able to manipulate Simon's feelings is another big perk of electronic control that I am really growing to love.

 

     Petermaeb10:    btw, are you still... you know... fingering your butt?

     Simonatorzz:     yeah... i'm doin it rite now >.<

     Petermaeb10:    turn on your webcam :P

     Petermaeb10:    i wanna see your sweet bod on video!

     Simonatorzz:     uhh i dunno.. lol

     Petermaeb10:    come onnn... dont be lame!!! you already sent a pic

     Simonatorzz:     FINE!

 

     Simon clicked the video button, and for the first time (to his knowledge), he let another person watch him over the internet. Except this time, I had something even better in mind. After all, it was time for my weekly maintenance visit...

     I got into my car and made a quick drive over to his home. I texted him from my iPhone to keep him busy with banter, and to make sure he was still by the computer.

 

     Petermaeb10:    damn simon your ass is relli nice...

     Simonatorzz:     hehehe :P it feels extra good when you're watching!

     Petermaeb10:    i bet, lol i could watch you forever

 

     I punched in his home security code and walked in without being noticed. Ashley wasn't home, and it was about to be just Simon and myself... I sent a last line of small talk from my phone and walked towards his room.

     Armed with the knowledge of his sluttish vulnerability, I made sure to be quick. My grand entrance was abrupt and I was obviously interrupting something important. Simon was blushing and frazzled, hastily closing windows on his computer.

     "Um-uhh hi! I didn't hear you- didn't hear you come in today," Simon stammered. His face was glowing red, and he was so flustered by his shame that he didn't even think about my rude entrance. "I-I uh, I was just talking to my- my sister, on the, online."

     "Oh, really?" I replied in feigned surprise. I decided to call his bluff. "I just talked to her at the supermarket... she left her laptop at home, you know?"

     I whisked Simon into my lap while he stammered and strained to think of an excuse. I wrapped my arms around him and teased him about an online "girlfriend", mockingly asking him if he liked her. When my playground-style jabbing looked like it was going to bring little Simon to tears of embarrassment, I decided to change the subject out of mercy.

     I chatted him up about video games and started teasing his body again, as part of our ritual. I rubbed his responsive nipples until they poked achingly through his threadbare shirt. I drew the subject towards girls and kissing and how his body felt at night. My steamy whispers breathed intimately against his neck, and other times against his ears. I let the electric charges build, build, and build in his nerves until finally I kissed him, right behind his ear at his most sensitive spot, and he moaned. I licked him there and he moaned even louder. I caressed his flat belly and soft chest from under his shirt, and I slipped his shorts off from under him. I ran a hand down his smooth inner legs to make him whimper, shake, then clutch at his hair and practically scream with pent-up frustration. 

     Try and cry as he might, however, there was little that Simon could do to escape the plans I had for him. Especially not in his soundproofed luxury cocoon of a room. Even now I had the option to drop every pretense, fuck Simon raw and spray his tight little body with my cum. And I laughed to think that every boy's room is supposed to be a sanctuary - it was a happy place, a safe zone. 

     I laughed because even in the space of his safest zone in the world, this kid was mine. Exposed, without the safety or comfort of the tiniest secret. 

     I kissed Simon's tender skin and tongued him deep in the ear, which drove him wild... seems little Simon was a squealer. I bit his neck and dragged my teeth on his skin, letting my hot breath do its magic. Simon was crying in confused ecstasy, but with state-of-the-art soundproofing he could yell as loud as he wanted. I casually lifted his right hand to my face... his guilty hand. A few of the small fingers were moist with spit and they carried a soft young musk. 

     "Mmh... I wonder where these little fellas have been," I smirked. Simon tensed up and froze, a look of genuine humiliation creeping onto his delicate face. How could I possibly have known about his bum-fingering marathons? How indeed...

     "Wh-what do you mean?" Simon asked in a weak voice, feigning ignorance. He was glowing red, mortified to even think that I was on to his dirty secret. 

     "Don't pretend with me, you little pervert," I whispered back. Simon groaned adorably - the boy knew he was busted. Did he really think I could tell just by sniffing the soft musk on his fingers? Nonetheless Simon tried to cover his face in deep, earnest humiliation. But I didn't let him have the comfort of hiding his face. Whispering that nothing he told me would surprise me, I looked Simon straight in the mirror. I put his thin fingers in my mouth and sucked on them, making them wet. I lifted his legs up with an arm, exposing his little package and pink, still-wet hole to the mirror. 

     I exposed his freshly fingered ass to my hidden mirror camera. It winked a few times in reflex, a drop of Simon's spit dripping out of the ripe entrance.

     "Why don't you show me what you've been doing with your little girlfriend, hmm? Then maybe I won't tell your sister about the little slut she has for a brother," I said, taunting his reflection. Simon hesitated, but I guided his hand towards his quivering hole. 

     "Make yourself cum... if you can," I crooned. I doubt if Simon even knew what "cumming" was, exactly - he had surely never experienced it to my knowledge. I pressed his fingers against his snatch and his inner boy slut did the rest, slipping two fingers inside of his delicious anus.

     "Auhhhwwhh, jeeezuss," Simon moaned. He swayed his lithe young limbs and I couldn't help pleasuring his body with him. I cupped a hand on his ass, spreading it open. Another hand grinded his hard little nipples while I licked and dragged my teeth on his earlobe. 

     "Ahh... you're so enthusiastic, baby boy... but you just can't hit that perfect spot, can you," I teased. "I bet it's just driving you crazy."

     Agreeing subconsciously, Simon pushed his fingers deeper, twisting them and moaning with frustration. It was a real stroke of genius not to let him learn about "proper" jacking off - watching him work up his hole in person was a real treat. I grabbed his arm and pulled him away from himself, relieving him of his futile attempts.

     "Why don't you let me help you out?" I offered, with smug condescension. I put well-manicured my fingers in his mouth, and he sucked on them instinctively. "I'm going to give you just a tiny taste of what a man can do... especially to a hot little cunt like yours."

     "Get ready," I smiled. I rubbed Simon's pretty sphincter with my thumb and relished how much I was going to blow his mind once I really got a chance to fuck him good. "This is gonna feel a whole lot bigger than the best you've got, and I promise it's not even close compared to what I can really do to you. You'll see soon enough... yeah open up there, nice and easy."

     I pressed against Simon's tight virgin entrance, and I slipped in my middle finger to the first knuckle. He grunted. Then I passed my second knuckle, and that's when I wiggled "come hither" against Simon Leighton's precious and hungry prostate. He nearly combusted.

     "Ooohh... yeahh that's good isn't it? That hits the spot," I cooed in a lilting voice. "Your little boy fingers were just too short to get there, weren't they? Hm, weren't they?"

     "Y-yes! OhhHH my goddd," Simon squealed in writhing awe. "N-no mmore, oh g--... ohhh..."

     "But Simon that wasn't even the whole finger," I bantered. "What I push the rest of my middle finger into your beautiful little spit-lubed hole, like this... oh, you're squealing so good... I bet I'm already further up your snatch than you've ever been yourself. What are you even doing without a man like me around..."

     "No m-more," Simon begged, slightly drooling. "I can't ta... ohh jesus ohh my god..."

     "What do you think about the second finger, huh champ?" 

     He practically raised the dead in protest but I slipped in my spit-lubed ring finger to the hilt and felt it stretch Simon's hole further. Now there were two of my thick, long adult fingers snaking into his innocent body. As tight as his cunt was, it naturally sucked my fingers in as though hungry for more. And funnier still, Simon's mind seemed to think it was too much! 

     I was aching to fuck the boy silly with my sizable cock, but just the fingers in Simon's ass seemed to be more than the hyper-sensitive youth could handle for now. To think - I'd already started turning this perfect boy into a bona fide anal slut, born to cum not by a woman's body, or even by his own hand, but by the irreverent and sinful abuse of his perfectly formed rump.

     "Are you imagining my fingers are a cock, Simon?" I taunted him, giving his nipple a good squeeze. Simon didn't have much of a poker face, and it was obvious I was right. Planting my fingers as deep in as they would go, I continued my verbal assault on my mewling, addled boy. 

     "Mmmh, yeah Simon, go ahead and pretend it's my cock... I like hearing you moan like that. And I know you don't even mean to make sexy little noises like this... you're normally so quiet and private! Oh there it is, I can see it on your face - this is all so embarrassing for you, hm?"

     By the third finger, Simon was more than ready to blow to kingdom come. But the sadistic man of patience that I am, I decided instead to take it nice and slow. While I fingered his helpless virgin hole, I kindly asked Simon to turn on his Blu-Ray player. It was voice-activated.

     As I expected, his TV started to play my pre-picked montage of erotic videos and pictures. They all depicted boys his age getting fucked, fingered, bound and teased. Some of the pictures were Japanese "shota" art, and he responded especially well to those. I interviewed him extensively on every video and picture, making sure his innocent mind soaked in every sensual detail, and that he was fully imagining himself in their positions. 

     Pretty young boys like him are so easy to read and manipulate.


 

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Entry 4



     I kept Simon squealing like that for an entire afternoon. I made sure to figure out exactly what he was thinking during each second of my prepared footage. Every time I learned something new about my slutty young consult, the grin on my face grew wider and my cock grew harder. I was exhilarated to be tainting his mind with lust.

     "So tell me Simon, how do hot little boys like you get to feel good?"

     "Auhhnnnh," he moaned. I was just winding him back up towards orgasm again, and his face was glowing red from the intense edging. "L-little boys like me... have to play with their ass?"

     "Very good, Simon! You won't even think about touching your little dicky like a bad boy, isn't that right? We can't even call what you have a cock. You'll only play with yourself in the bum!"

     Simon nodded and panted helplessly in pleasure. His O-faced mouth curled with a smile when I kissed his neck, happy to receive the praise. 

     "Now Simon, I have to go soon. So I won't have time to give you what you really deserve... but I do know how you can make yourself feel good while I'm gone."

     I pulled out a few items from my work bag. One was a cell phone with my number programmed into it. Next, I pulled out a very expensive, very uniquely designed butt plug designed to get any boy's ass boiling with pleasure. It was baby blue in color, and built to target the prostate while its length would prepare a virgin ass to be deeply fucked. The base of the toy narrowed around a discreet flare knob, which would keep the plug inside of Simon's bum for extended periods of time. 

     "This is Big Bill... he's gonna be your new best friend from now on, okay? And this phone is what you'll use to call me while you're putting him inside you for the first time. You can even do it tonight, right after I leave."

    "It's... He's... so big," Simon replied huskily. The boy was still impaled on my fingers, and I rubbed the length of the plug along his inner thighs to let him know how much would be inside him.

     "Yeah he's big," I teased reassuringly. "But you're going to give him a try, I know you will. You're a natural born boy-slut and you'll never turn down the chance to make your ass feel this unbelievably good. You're too curious!"

     "I don't know about that," he moaned. My fingers were wiggling deep in his ass, and I could feel him tense up whenever he even looked at Big Bill. His button nose scrunched up, full of hesitation and concern. 

     "I don't think I'll really use it... it's way too big."

     I smiled at him, and pulled out my fingers. He let out a needy gasp of pleasure when I pulled out, and that was enough to let me know what was sure to come next.
 


 

 
=====

Entry 5

 

     It took Simon all of fifteen minutes to call me on my phone, spilling his guts to me while he pushed the fancy dildo further and further inside his hole. As kinky as ever, Simon was in his sister Ashley's room. He was squatting down on the ground, resting the base of Big Bill on the floor while he lowered his ass onto the impaling toy. It was dripping with his sister's lube.

     I ogled Simon on the video, intently watching his slim body despoil itself. It also made me smug and unbelievably hard whenever I noticed the little micro-expressions of shame, hesitation, and fear. I was witnessing his ultimate vulnerability without his knowledge, and I got to see how his inhibitions were swept aside by the sexual curiosity I so carefully cultivated. 

     And of course, I decided to open up a link on several image boards and livestream. The viewers could toggle between any one of the cameras set on Simon, and they could hear every word I said to him over the phone. My channel exploded to a thousand viewers in the first five minutes, and that's when I knew the fun would begin. 

     "Why is having Big Bill in your ass making you so hard?"

     "I dont know," Simon whispered. How naive. He fidgeted weakly, exhausted but unable to control the rolling shudders of ecstasy. "I want... I wanna take it out. Take him out, I mean."

     "Ok, I'll help you with that," I lied. "Why don't you spread your legs some more, and push your muscles out against Big Bill? Just keep a finger pushing against the hilt."

     "Ohhh!" 

     Simon complied, moaning in surprise - the tapered plug slipped several more inches of itself deep into his hole. It was physics, working against the hapless boy. Simon realized he was tricked and tried to pull out the toy, but his muscles tensed up with the slightest movement. The contractions pulled even more inches of the toy inside him, until it was so deep in Simon's virgin flesh that he could barely move. 

     "Nnnnhh I just need to take him out for a second," Simon whined, moaning helplessly. He tried to pull it out again, but Big Bill was already too deep. Moreover, the bum-clenching was what slipped those extra inches inside him to begin with, and now they were keeping them there. 

     "Feel how deep he is inside you," I cooed. "Tell me what it's like to be Big Bill's pretty little bitch."

     "MMmmnhhmmh... I don't, nnh, I don't know," Simon moaned helplessly. His precum was leaking all over the floor. "I just mmmhh... just want it to s-stop..."

     Simon started to cry, pathetic and confused and horny. 

     As horny as he'd ever been in his life.

     "Oh, Simon baby, it's obvious what's going on in your ass," I dirty talked. "I can tell from just your face that you can feeel every bit of Big Bill, can't you?"

     Simon pressed his hands to his chest and squealed in confirmation.

     "You can just feel him rubbing and dragging against your nasty, naughty sweet spots." I checked the stream, and it was exploding with comments at 12,000 viewers. 

     Simon was too young to be prepared for all these feelings, and he was gritting his teeth from shock. It didn't hurt, in fact he felt intense throbbing pleasure. But it wasn't the pleasure alone that was overwhelming him.... it was the penetration. 

     "Let me tell you what you're feeling, hmm, sweety? You're feeling Big Bill's girth, his length, he's so deeep inside you... and it's all too much for you to understand isn't it baby?"

     "NNnnyhhahhhh!" Simon screamed in sexual overload. "Pl-please!"

     The beautiful young boy couldn't handle it - the subconscious knowledge that this inanimate object was in control of his entire body. That he was at mercy to a simple butt plug. Simon was used to holding the reins of his own penetration, able to withdraw his fingers at will. But now this thick, scary plug was nestled so deep inside him. His body wanted nothing more than sphincter to be granted mercy and safely close his body off in peace. This... this insolent plug was keeping Simon's sacred passageway opened wide and beyond welcome, leaving him defenseless and debased. 

     The channel was at 19,000 views now. Already some people had figured out who the boy was, and a few websites were up to enshrine his sexual exploration. Others were posting stylized photoshops of Simon's bliss. A few were even saying they lived in the same neighborhood - they couldn't believe how big of a slut he was, and they were laughing their asses off to see him played like a fiddle. 

     This all felt completely out of the boy's control, and it was. I set the vibrations to max and had them come and go in waves. Then I turned on the "wiggle" feature, which made the vibrator slither and bend itself against his flesh like a snake trying to push deeper and deeper inside of his body. Simon's hands clutched feebly at the flared base, hoping to keep it out but to no avail - the last few inches left of Big Bill had now "wiggled" itself into his bum along with the rest. 

     With the entire long, lubed toy inside him, a shell-shocked Simon plopped his round perky bum against the ground in resignation. Big Bill was sapping the power from his body and making him legitimately afraid of what his "new best friend" could do to his body.

     Simon wasn't ready to feel this way, and he didn't know how to process the shockwaves of pleasure screaming through his body. And he DEFINITELY didn't know how to process the sudden vibrating inside his ass when I turned it on from remote control. 

     "MMMMMmmmmnnnnnhhhh!! Aawhhh my goddddd!" Simon moaned out loud. "What the hhellll... this is... unnnhhhh!!"

     "There's only a few more inches left," I beckoned. "Just sit yourself down on the rest of him and tell me about how it feels to have Big Bill completely inside you."

     "Annhh! Ahhnnh! It f-feels... mmnh? So warm, an-and deep, and there's so so much, ohmygod there's so much!"

     Simon's body started to spasm uncontrollably, and he clutched his stomach as though he were cramping. But there was no pain - only overwhelming sexual stimulation. 

     "It's too goood," he moaned. I could tell this was the time to push Simon to the breaking point, so I turned the remote control's dial to the setting in black - the one labeled 'boybuster'. I could only imagine what combination of writhing, rotating, pulsing and vibrating was being used to bring Simon's tender pink ass over its limit. 

     "You're going to cum now, Simon. You don't even know what that is, to cum, but Big Bill is gonna make you cum so, so hard. Just look at you, you're only a little boy but you're already the biggest slut I've ever seen, stuffing such a big thick rubber cock in your hole so you can feel what it's like to have a man..."

     "UUNNnnnhhh-nnnooo... annh... annhh!" Simon became incoherent as he neared the first orgasm of his life. His pert bubble butt was grinding against his sister's floor now, mashing his pink hole against the base of the toy. Simon's lithe young frame shook uncontrollably, the boy clutching at his stomach and reverting almost to the fetal position as I manipulated his body to an explosive anal climax for tens of thousands of viewers to see. 

     "Annhh! Annhh! I c-can't...there's t-too much... ohmygod ohmyg...anh... annNnhh... aaAAnNNHH!"

     "You're cumming now," I whispered along with his screaming orgasm. "You're coming because it's the first time you've been fucked so deep in your ass, and let me tell you - Big Bill ain't going nowhere, and I'm making sure it's only going to get better with every... single.. day."

     "W-w-waai-ooooohhhhHH! FFfffuuuuuuuckkkk!! AAAnnNNNhhHH! AAUuGGghhhH! " Simon cried. Tears of confusion and joy streamed down his model-worthy face as he lost himself in orgasm. I never stopped dirty-talking him deeper and deeper towards ecstasy, and it caused his innocent body to roll in pleasure longer than any I had ever seen. 

     Simon had over 43,000 viewers by the time his orgasm was complete. He wasn't old enough to produce sperm, but he still managed to leave a shamefully large pool of precum in his wake. Men, women, girls and boys alike were watching as Simon Leighton slowly came down to earth, all of them knowing that an obscenely large sex toy hidden in his ass had just brought him to climax. Thousands demanded more, and a handful even claimed to go to his school, and that they would film him as well from a distance. My dummy inbox was filling up with requests, ideas, and praise - this boy was now the center of an entire voyeuristic community. 

     I picked out the more interesting comments and decided to go with a more daring suggestion - I instructed Simon to keep the plug inside him for the next 5 days, and to only remove it when he needed to. In his state of weakness, he agreed without even realizing he could say 'no'. I told him to put his Pikachu panties back on and go to bed - without cleaning up the stain in his sister's room. Again, he agreed. Simon was on autopilot, riding waves of shame as well as a sexual high. 

     I decided to leave the stream on indefinitely. The community deserved to see what I got to see, and they had proven to have some good ideas as well. A few viewers offered to set up cameras at his school classrooms and even in the boy's room he preferred to go to. With constant knowledge of his whereabouts, I planned to abuse Big Bill's 'boybusting' abilities at the worst of times for my stuffed little nymph.

    But not of course, without leaving Simon a good night message as I went to sleep.

     Petermaeb10:    btw simon, you left your webcam on

     Petermaeb10:    and you left your door open

     Petermaeb10:    while you were at your sister's room :P

     Petermaeb10:    i could hear you cumming all the way from here

     Petermaeb10:    you've gotta let me watch you play with big bill!!

 


 

 

-----------------------------------

Hi Readers!

I'm working on some other series as well. I could use feedback and ideas!

royalredsheets@yahoo.com

 

 

 

My other stories on Nifty are:

 

  "The 'To-Do Robbie' List"  (young-friends) Link

 

  "The Magic Words"  (adult-youth) Link

 

  "Summer Camp To-Do List" (young friends) Link

     *note to self: need to edit this one

 

  "Guardian Stalker" (adult-youth) Link

 

  "Little Red Riding Hood" (adult-youth) Link

 

  "Post Abduction Therapy" (adult-youth) Link

 

  "Englishman's China Minx" (adult-youth) Link

 

 

My ASSTR Dump