Babysitter Supreme

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#1 of Babysitter Supreme

My first successful short story!


Kyle was sitting on the wrap-around sofa in the basement of his house. At age thirteen, he was constantly in trouble. Being that he was a wolf, it was difficult to find a more obstinate species at that age. Grey fur? Dyed black. Clothes? When he wore them, they were only the darkest he could find, some even depicting gods or angels of death. And now, because he literally blew up the microwave for fun, he was on another one of his two week groundings where his parents hired a babysitter to watch him when they left.

"Kyle!" he heard his father yell down the stairs. "The babysitter's here and I think you'll want to meet this one!"

"Why bother!" Kyle yelled back, bored and frustrated. "She's just gonna quit after the first night like the others!"

After that he heard a few mumbles before an unfamiliar voice yelled down the stairs, "Just get up here you little shit!"

For a moment, Kyle thought he was going to piss himself. That voice had been so loud that he could have sworn it was right next to him. So, with his legs shaking, he threw on a pair of shorts, and ran for the stairs. The second he stepped around the corner to the front door, he thought for sure he was going to die. His father was wearing a specially tailored suit that almost matched his black fur, his mother wearing a blue dress that showed off her pure white fur, but behind them was a creature that dwarfed them both. A very muscular white tiger, maybe his age by what he knew of them from school, stood holding what appeared to be a coffin, just slung over her shoulder.

"Kyle," his mother said in her usual sadistic tone. "This is your babysitter for the next week, while were gone."

"A pleasure, brat," the tiger growled at him.

"I have a strong feeling that Evelyn might just be able to keep you out of trouble while we're gone," his father added, looking at his watch. "As your mother said, we'll see you in a week. Try to stay out of trouble this time."

Then they walked out the door while Kyle panicked thinking, Oh shit, oh shit, OH SHIT! You are not leaving me alone with this thing! Meanwhile, his heart beat harder and harder as the door closed, and with each further step that he watched his parents take on the other side of the glass. When he heard a loud thud, and felt the floor give a little beneath his feet, Kyle whipped around to face the tiger that was his babysitter. The coffin was now standing upright on the floor.

"Now, your parents left two rules for me to follow, directly pertaining to you," Evelyn said as he stared up into her icy eyes. "No video games, and no computer, unless you need the internet for your homework." They both stopped as they heard the car doors close, sealing Kyle's fate. "I have plans beyond just watching you though, brat. Let's see how long you last."

Kyle finally found something that could unglue his fear-stricken feet from the floor. With only fear driving him, he bolted down the stairs, jumped over the back of the couch, and hid behind the gargantuan TV stand and bookshelf. After a moment, he heard footsteps coming down the stairs and began to shiver in terror, just before he felt a warmth spreading down his thighs that he recognized but didn't care about.

Another loud thud from the coffin, sounding like it came from the bottom of the stairs, made him stop and think, and the realization that he was now trapped in the basement made him want to slap himself. Then a large hand ripped him out from his hiding spot and threw him to middle of floor, almost fifteen feet from where he was. "Now listen well, brat," Evelyn said firmly. "When I say to do something, you do it, and you will either call me ma'am or mistress from this point forward. Finally, if you want to do anything, you will ask permission first, unless I instruct otherwise. Understood?!"

Kyle flinched at the ferocity in both Evelyn's eyes and tone, nodding quickly. The next moment, Evelyn only smiled, which made the teen flinch again, seeing the pearly white, razor sharp teeth. She walked over to the coffin, opening the lid and revealing a treasure trove of sex toys. The wolf cub was no stranger to porn, or masturbation, and could name most of what was in the coffin, but what terrified him was that she was already looking at ones on the lid that were hidden from view, behind her body.

"Strip," she ordered, grabbing something and closing the coffin. Kyle didn't want her pissed off at him and complied. "And another perfect match," the tiger said with pride clear in her voice as she looked him over. "That's three in a row."

"What's three in a row... mistress?" he asked fearfully, almost forgetting one of her orders.

The tiger silently walked over, looking at him hungrily. "Just this," she said reaching down and expertly massaging his sheath. It only took a moment for him to start getting hard as he leaned his head back in pleasure, but then he felt something slide over his shaft and looked down and saw a rubber cock ring. "A little gift. We're going to save that up for three days. You will get to take that off once before school, and once when you get back, just long enough to take a piss. And Kyle. I'll be watching."

It was three very nerve wracking days, but he had no idea what Evelyn had in store for him. Most of day one was spent fighting his raging hard-on, and day two wasn't much better. He had tried getting the cock ring off himself when no one was looking, but failed. He hadn't even bothered trying to masturbate, and his thoughts flooded with sex by the time he went to bed that night. So at the end of his third day of school like that, Kyle decided he wanted a friend with him to make sure nothing happened to him. Marcus, the football quarter back had said he could help with the "babysitter problem" and followed Kyle home.

With a big smile on his face, Kyle walked into the house, Marcus following suit. "Oh, you brought a friend!" Evelyn yelled from the lounge chair, holding a book against her chest. "And how are you today, Marcus?"

Kyle's smile faded as he looked back to the lion who had suddenly grown very pale. "I'm sorry, Kyle, but I have to go, now!" Marcus said as he bolted out the door, leaving the wolf cub to shake under the predatory gaze of the tiger as the tip her tail flicked lazily from side to side.

"What a shame," she said mockingly. "And here I was, hoping he and I could have some more fun together."

Kyle dropped his backpack, utter shock setting in. In the next few minutes, he soullessly went about his new routine, his new mistress watching the whole time as he pissed, ate dinner, did his homework and watched TV by her side. At sunset, things changed. His balls already felt like bursting, after just three days, and his mistress ordered, "Strip."

Kyle stood up, stripping down naked before turning to the tiger with his hard-on still painfully at full mast. Evelyn stood up, stripping down herself, and revealing that she had both a dick, and a cunt. She was sporting a sizable hard-on, much larger than Kyle's, which made him shake in fear all over again. "Let's go down to your room," said, guiding him down with a tight grip on his shoulder.

Once there, she briefly motioned to the bed. Kyle got the picture, following her order as his ears drummed, but before he could lie down, the tiger ordered, "Stop, right there," almost whispering.

Disobeying her would be suicide, but surely that had to be better than what was about to happen. "No," Kyle said defiantly as he rolled over and pulled his blankets up over himself.

Evelyn walked over to his closet with a smile, silently opening the door, reaching in, and dragging out her coffin of toys. Oh shit! Kyle thought to himself in terror. How the hell did I forget about that!?

The tiger pulled out a dog knot dildo, easily the size of her dick, and said, "Chester, I still love you the most!"

Pulling the covers off of him, Evelyn moved quickly to uncover Kyle, roll him over, and pin him to the bed. From where he was, Kyle couldn't see what Evelyn was doing as she sucked on the dildo getting it nice and wet before pulling the wolf cub's tight ass cheeks apart and spitting on his virgin pucker.

Pressing the dildo into the wolf's ass, she giggled as he moaned in pain and pleasure. What he didn't know was that she had picked her largest canine dildo, and it was sliding in, inch by painful inch. "Please, stop," the wolf whimpered, feeling the dildo stretching his pucker. "Please, I'll let you do whatever else you want to me, but-"

"Oh, just be quiet!" Evelyn grunted, quickly pushing the last two inches to the knot, causing the wolf cub to gasp. "Now just deal with it one more second."

A moment later, the wolf screamed in agony as the knot at the end was forced into his ass, which quickly tightened around the base. He shook for a few moments as the pain subsided some, just feeling where the dildo sat, inside his ass. Then, the tiger let him go and rolled him over.

As the wolf cub looked up at her crooked smile she said, "That's for disobeying an order. Now just sit still and let me work."

After that last moment of pain, there wasn't a thought in Kyle's head about listening to her. As he panted, she climbed onto the bed, positioning herself over his dick, which was now harder than ever. "Now, to complete my plans for you," she said coldly, as she slowly came and began to ride his cock.

For a few moments, it felt amazing, and just when Kyle thought he was about to cum, the cock ring stopped him, the pressure building behind the blockage before he started to whimper. "Please," he whined, pain and fear that his cock might explode causing his head to hurt too. "Please, I need to cum so bad! Please, mistress, let me cum!"

"Do you promise you'll listen to your parents from now on?" she demanded as she continued to ride his cock.

"Yes!" Kyle said, tears starting to stream from his eyes.

"You won't break anything for fun anymore?"

"No!" the boy cried.

"And you realize that if I find out you lied to me tonight your punishment will be worse than that doggy dick up your ass, right?"

"Yes!!" he screamed in reply, the pain building excessively as a second climax got blocked by the cock ring.

As she continued riding the wolf cub's cock, she quickly sliced the cock ring with one of her claws, and braced for the cum that would push her over the edge, into her own climax. The boy's cock erupted, dumping more cum into her than she thought he could, and as she screamed in ecstasy she felt the rush of fluid from her pussy, onto the boy below her and the bed sheets below him. When she came down from her pleasure high, Evelyn rolled to lie beside the boy, noticing that he had fainted. Briefly kissing him on the cheek she said, "Goodnight Kyle. We'll remove that toy from you in the morning. And then, we still have four more days until your parents get home."