Sylvia's Boy Toy Ch. 01-02

She had lead him literally by his dick into being her bitch, and he wasn't sure how she had done it. He usually displayed much more resolve than he had shown tonight - how had she managed to make him fall to pieces like that? And how the hell had he stayed hard for so long without the aid of a viagra? He was certain he hadn't taken any.

He pulled into the driveway, looking at his dark and empty home. He gloomily looked at the dark windows. Even in his current haze, his eyes did their habitual glance to his bedroom window to see if the light was on - but of course the light was out. The light had been out upon his return home for the last five years. He knew he should stop looking, but old habits die hard. With another sigh, he clambered out of the truck and up the walk to his front door. He was so dazed that he didn't realize he had left his keys in the ignition until he reached into his pockets for his keys. He had also left the truck's lights on.

He returned to the truck, turned off the lights, and grabbed his keys. He slowly walked up the pathway a second time to his door, his body sore and his head still dizzy.

With a twist of the lock he let himself inside. He didn't even bother to turn on kitchen light, as he knew his way through so well he didn't need it. Walking like a zombie, he made his way through the dark house to his bedroom on the first floor. In all technicality it was his living room that he had transformed into his bedroom 5 years ago. He tried to avoid going upstairs for anything if he could avoid it. Josh fell into his bed fully dressed, stopping only to kick off his shoes. All he wanted now was to sleep. In the morning, he would turn his mind to the situation he had found himself in, when he would be able to think clearly. It was time to drop off into dreamland.

As he drifted off, Josh had a random thought of surprising clarity. The thought made him uneasy...She knew my real name. He had never shared this with Sylvia - how did she figure it out? But before he could think about it any more, he fell asleep.

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Chapter 2 - The Beast

Click clack click clack

The young woman's bountiful breasts jiggled sweetly in rhythm with every step of her stilettos. Her booty swung entrancingly with the steady movement of her hips, but for now there were no eyes staring at her round backside. The rooms on both sides of her were full of whores and their horny clients, but the hallway between the rooms was currently empty.

Everything had gone according to plan. Everything.

As Sylvia passed from door to door, she could hear gasping and moaning from clients inside her rooms, women being serviced. Women being licked and sucked. Women having orgasms. She also noted that she did not hear any shaking beds or the steady clapping of flesh on flesh. No moaning from any of the men. None of them were currently fucking at the moment, which meant none of them were breaking her rules. And that was good.

Yes, everything was going her way.

At the ripe age of 21, Sylvia O'Neal was living her best life. She had become filthy rich when she turned 18 as well as extremely beautiful, and now was fulfilling almost all of her deepest and darkest sexual desires. She had it made. And now, she would soon have a new man to bend to her will, to break.

Sylvia thrived on the breaking of men. Nothing got her motor going quite like making a man suffer for her pleasure. Joshua was strong willed - he would not break easily, but after 3 years of this lifestyle she considered herself a pro. Bending and breaking Joshua did not make her anxious, rather she was excited and looking forward to the challenge. Sylvia believed that every man could be broken in, you just had to properly lead them by their dick. And Josh had proven that true, just two minutes ago.

And what a great dick he has, thought Sylvia, thinking dreamily of Josh's thick cock. It had looked so damn yummy, she had to restrain herself from shoving it all the way down her throat while in the room with him. She also had to restrain herself from licking up the tasty cum he had blasted all over himself. She had hired a man to slip some drugs into his drink at dinner earlier that evening, to make sure he was hard and horny when she arrived, plus a little dazed and confused. And hard he certainly was. Thinking of his dick made her pussy quiver with excitement. Little did Josh know that when she rubbed the bottom of his dick against the outside of her vagina, it has taken all of her resolve not to allow his cock to enter her. It was a relief that he had came so quickly. He had no idea that she desperately had wanted his cock to plunge deep into her womb quite as much as he did, but that she couldn't do it. She had made a promise, and even if she hasn't made that promise, she wouldn't allow him to enter her that easily. She also had guessed correctly that it would take more than a shit ton of money to convince Joshua to become her slave, and so she had taken the risk. She had tried just offering money first, but when he turned her down, she turned up the heat. All she needed to do was tweak the circumstances and seduce him. And it worked. He was as good as hers now.

Josh was an incredibly good-looking man, with his handsome face and sexy body. Yes, breaking in Joshua Cardone is going to be a real treat.

She couldn't wait to get started with her new boy toy tomorrow. But for tonight, it was her last night with Harold, her 39th slave. He didn't know yet that it was his last night with her, but she was firing him tonight after she was done with him. After one last hard fuck in the ass.

He will be alright, Sylvia told herself. He will land on his feet. Or on his knees in front of someone else.

Yes, Harold had been a good slave. A little too good. A little too behaved, a little too submissive. And a little too boring. She preferred men that tried to resist first. But Harold never did. He was always willing to do exactly everything she said without hesitation. But it was time for him to move on, to become a slave for someone else. After all, why would she still want to use and abuse poor Harold when she would soon have Josh? Harold was a bore that took out all of the fun out of being a dom. He submitted to her will without hesitation from the word go, never squealed in any pain. The only reason she had been able to cum a few minutes ago when he ate her out was because she had been looking at Josh's killer body and his magnificent cock. He also had talked smack and had given her attitude. Most guys didn't do that and only fawned over her. His body and attitude had aroused her, and so Harold had finally managed to make her cum. But the night was young...she would try to squeeze at least one or two more orgasms from him tonight before she threw him to the curb.

She opened the door to find him kneeled obediently at the foot of the bed, just where he was supposed to be. His eyes lit up with happiness at the sight of her.

"My mistress, you've returned."

"So I have, 39. I have a surprise for you. On the bed, on your knees."

He obeyed without any hesitation, his bottom sticking up in the air. Pure obedience and submission. Boring. Well, she hoped to get some sounds of resistance or pain out of him tonight. Time to put on the beast.

Sylvia strode to her massive box full of sex toys. It took a minute or so of rummaging before finding what she wanted. It was been buried deep likely because she didn't use it often. The beast was a gigantic strap on dildo, 12 inches long and nearly as thick as a soda can. She hurriedly buckled it around her waist, only pausing to take off her shoes again. Then she made her way to the bed where Harold was on his knees, his face buried in the mattress.

Sylvia climbed on the bed and came up behind him. She swiftly smacked his ass hard. He jumped slightly, but there was no cry of pain. She tried again, even harder. Nothing. A third smack with all the force she could muster. His ass was turning crimson and she could see the imprint of her palm on his cheek. Why won't he show any sign of being in pain?! Well, if the spanking didn't work, the beast will. She had yet to fuck someone up the ass with the beast that didn't cry.

She reached for the butt plug she had shoved inside him this morning. She had never shoved a butt plug up his rear end before, but she knew that he knew the reason why. It was unspoken between them, but they both understood. She wanted anal tonight, and not in her ass, but in his. And she had wanted to prepare him for it by stretching him out. Yet there has been no fear in his eyes, no anxiety at the prospect of being pegged. And that was not good, it was disappointing. He was too comfortable, too content with their arrangement.

She heard a sharp intake of breath as she began to twist the butt plug around his ass like a doorknob. But otherwise, silence.

"How does that feel, 39?"

"It...it feels good my mistress," he replied.

She pushed the plug as far as it would go.

"How about now?"

A moments pause...

"Still - still feels good, mistress."

She twisted it some more. His body tensed slightly, but otherwise no sign of pain.

"Really? It wasn't painful having something this large shoved up your ass all day? Didn't make you feel any discomfort? It's alright if it did - It is my biggest plug."

"N..no, my mistress. It felt fine." He was beginning to breathe heavily now, and he gave another sharp intake of breath as she popped out the plug, stretching his anus. It had to have hurt, but he did not give her so much as an inch. She continued,

"You know why I put this in today, don't you?"

Another pause...

"To...to prepare me for getting fucked in the ass, mistress." He relied barely above a whisper.

Sylvia smiled.

"Yes, I am going to fuck your ass."

She bent down and reached around his middle.

"Wh...what are you doing, mistress?"

"Removing the cage. You've been such a good boy for your mistress. You may get hard, if you wish. And if you are super good for me, my slave, I will let you cum."

The cage was unlocked and tossed aside, setting his dick free. She reached down to grab hold of him. Small and soft. Well, maybe he is a grower instead of a show-er. She certainly hoped so. After the beautiful stud of a cock on Josh, this was a definite downgrade.

She tugged on his penis for a while, hearing him pant, sweat glistening his shiny bald head. After a minute or two of persistent tugs from behind him, he finally gained an erection. Turns out he is a show-er after all, he just didn't have that much too show. It couldn't have been more than 4 inches fully erect. She frowned with dissatisfaction.

She kept pumping him though until he was on the brink of coming. Then when she felt him coming close to the edge, she removed her hand. He groaned. Finally, some resistance. She smiled. Maybe I should have removed the cage way before this. But she knew that would have been a bad idea, because even with a small dick, she may have been tempted to break the promise she made to...well, perhaps it was better this way.

She grabbed some lube from the stand on the side of the bed, and applied it liberally along the first 6 or 7 inches of the beast. Then she lined up the enormous dildo head with his asshole. He froze.

"That butt plug you've been wearing today should have loosened you up a little, but it's still going to be a stretch. It is probably going to hurt a little, maybe a lot. Prepare yourself, 39."

He tensed up - one of the worst things to do. She smirked satisfactorily. And then she thrusted forward with full force. With a small pop she had squeezed the massive head through his sphincter. He gasped. She frowned in annoyance. She was hoping for a scream. He was nearly as silent as the grave.

The gigantic dildo must have been splitting his asshole nearly in two - his anus torn to shreds. Yet Sylvia plunged on, pumping the cock roughly and deeply into his asshole. As he turned his head to the side, she got a glimpse of his face. His eyes were shut and he was gritting his teeth into a grimace. So it did hurt, but he didn't want her to know it hurt. She picked up speed and fucked him even harder, trying to make him squeal. Yet he did not make a sound.

Smack smack smack smack smack.

Sylvia pounded into him again and again with all the force she could manage, trying to make him scream. Then she would be able to cum. But he didn't make any sounds. She began to taunt him, to get a reaction out of him.

"How does that feel, having this big cock fucking your ass? Does it make you feel like a real man?"

"Yes, yes it does."

She reached down and twisted his balls. A cry out in pain.

"I mean no, no it doesn't!"

She twisted them again.

"So which is it? Yes or no?"

"N...n...no! Gah, that fucking hurts!"

His admission of pain did not make her slow down - if anything she began to fuck him even harder. Faster. She reached down and began to stroke her clit furiously.

"Cry out for your mistress! Cry out for being the little bitch that you are!"

He had begun to whimper. But when she reached down with her other hand (the other one still busy with her clit) she found him to be rock hard.

"Wow you are hard! Are you enjoying this? Do you like being my bitch? You are enjoying this pain I am giving you, aren't you?"

"Y...yes!"

"Cum for me now, cum for me, my slave!"

Sylvia then shoved the strap-on dildo as far into his ass possible and held it there. She began to stroke him while rubbing herself.

Then she heard hit - a sob.

Fucking finally! That one sob was all she needed to hear to get her to home plate. She quickened the pacing of both of her hands, the one on her pussy and the other on hand around his tiny dick, and then they both came at the same time. He didn't produce much seed, not even a quarter the volume of Josh,but a small amount of semen did spill out onto the sheets. He moaned loudly, whether in pain or pleasure she could not tell. But she barely noticed, so wrapped up in her own orgasm. She felt waves of pleasure fill her brain and body. She continued to pump his dick until he had spilled whatever dribbles of cum he had left. She continued to pump it even after he was finished and hyper sensitive. He tried to buck her hand away but she only gripped him tighter.

Slave and mistress remained stationary for a moment in limbo, with a dildo deep into Harold's ass and her hand still yanking his over-stimulated dick. He had stopped trying to buck her away and let her continue to tug on it, even as it went immediately flaccid. He also had tears in his eyes. Finally, she removed the dildo from his anus. He was bleeding. A satisfying whimper escaped his lips. Music to my ears. It was time to say goodbye to this excuse of a man named Harold.

"Get off the bed, 39."

He whimpered again. She grabbed his balls again and twisted. The whimper turned into a scream.

"I said, get off the bed!"

This time he hurried to obey, scrambling off the bed and hurriedly to his feet before her.

"I am sorry for not listening the first time. Thank you so much for my orgasm, my mistress."

"You're welcome, 39. You've been a good and faithful servant. A good slave. But unfortunately I have to sadly inform you that this was our last night together. Think of your orgasm from me as a goodbye-present."

"You're...you're firing me?"

"Yes. You must leave. Now."

He stared at her, disbelief etched into his face.

"But...but I let you fuck me in the ass!" He sounded half exasperated, half pleading.

She looked back at him without a smile.

"Life fucks all of us in the ass from time to time, 39." She was still frowning. "I am going home now. When I come back here in the morning, you will be gone. I will mail you for final check. Understood?"

Harold's mouth gaped at her, but she took his silence for affirmation.

"Goodbye, Harold."

He looked shocked at her actual use of his name, but she barely took notice. She wouldn't look at him anymore. It was easier this way, to move on and look towards the future. And after only pausing to grab her shoes and trench coat, she left the room.

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She passed like a ghost through the dark hallway. Her brothel was truly empty now. Without the crisp click clack of her heels on the hardwood as well as the absence of noise happening behind the doors, it was dead quiet. All of the clients and all of the prostitutes were gone.

Correction. Most of the prostitutes.

A light was still blazing in the final room - she could see the light filtering through the bottom of the door.

Josh's room.

She glanced out of the window. Only two cars left in the lot - her BMW and a his Dodge. Which could mean only one thing...he was alone. She tiptoed silently and pressed her ear gently against the door. The sound of grunting and a soft rhythm. The rhythm of a cock being stroked. His cock.

He is jerking off! She couldn't believe it!

After all the cum he produced earlier, two hours later, he is still jerking off! Perhaps the man she had hired had given him a little too much viagra! The thought exhilarated her.

Then she heard a moan, louder than ever. She listened harder at the door, and then he spoke.

"Oh, Sylvia..."

She softly gasped. He is fantasizing about me! She began to rub herself, picturing herself in the room with him, feeing the length of his magnificent shaft envelop into her juicy folds...we could do it right now. I could open this door and we could fuck. All night long. She reached for the doorknob. Suddenly she heard him cry out. He must have came! The thought excited her even further - she wondered how much he had cum this time? If she opened the door, she could find out...

But she didn't find out. All at once a memory swam into focus, a memory of a promise she had made to someone....And then she stopped herself in her tracks, horrified at what she had nearly done. She removed her hand from the doorknob as if it had burned red hot. She quietly removed the other hand from her crotch. She paused, listening hard. She heard a groan and the squeak of the bed. He was up and moving around. It was time to go. As quietly as she could, she picked up her things, and walked silently to the door.

There would be plenty of time for them together tomorrow. Tomorrow, when the real fun would begin.