The Babysitter: Part II

Story by Texleo on SoFurry

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The third installment of The Babysitter series: a series that follows the normal boy Connor and his dominant, Cleo.

Remember to check out the previous stories so you can get the gist.


The lithe bodied black furred tiger collapsed against the tiles of the bathroom floor. It was like lying on a bed of ice! Cleo had well... destroyed him? Abused him? Violated him...? Only dark verbs seemed to describe what had just happened to him, so why did it feel so god damn good. He felt exhausted, every muscle strained and his heart pumping but, he felt really good.

Pulsing with energy, electrified; like stepping into the cold night air after a really good gym workout. His body dripped with a dozen different substances and his mouth was still salivating. He felt he had left his mind back in the room and that it was still sluggishly trying to catch up with him... so THAT had been Domination...

"W-w-what's this r-r-room?" It was all he could manage.

Cleo smirked and pushed open the door. "Well, you've made friends with the kitchen, the den and my room. Now it's time to get comfortable... in the playroom."

Cleo the wolfess stepped inside, lingering in the doorway. Conn followed carefully, anxiety churning his stomach. His hostess was dressed in quite a dark fashion.

She wore tight black leather shorts, with a solid silver buckle; that and a purple latex jacket that clung tightly to her arms, shoulders and her back. It seemed to have no front, leaving the chest completely exposed were she not wearing a grey sleeveless top underneath... Stencilled in black were the words Rogue Bitch, something she seemed all too pleased to advertise. Her dark navy fur was complemented by the icy bright blue splotches of fur on her thighs and neck, a few spots under her right eye. Her lengthy hair fluffed up on top, almost reaching as high as her pointed ears. The back was once again pulled into a pony tail. She also had laced streaks of her hair with purple highlights

She was a head taller than Conn with chunkier hips and a belly, breasts and booty to match. And now that she had stepped to the left, he could see the room ahead. It was very spacious with a low ceiling, black shag carpeting and warm wooden walls. Red curtains were drawn across the far wall and golden lamp brackets along lit up the room in a cosy orange glow.

There was a slab in the middle of the room with blankets drawn neatly over it. Conn guessed it was a bed, just with no headboard or bedposts. But of course, his eyes were drawn to the two sets of shelves stacked up against the walls. They were like ornate bookshelves; one however was filled with sex toys, apparatuses and objects that one could only fantasize about. Dildos of various sizes and shapes, from little nubby anal plugs to arm-length equine shaped silicon cocks. Strap-on harnesses hung from pegs in the wall, beside lengths of rope, chain, whips and collars. The other shelf had rows of boxes, all shut and sealed.

Conn drank in the sight, filling ill. He had been expecting a vibrator and pair of furry hand-cuffs at best. Maybe forced to lick her out for the hour, or rub his face in her foot. This... this was different. He made to leave but as if she had read his mind, Cleo shut the door behind him, grinning wide.

She was looking at him hungrily. She even licked her lips, as if he was a meal. Swallowing the queasy build up in his throat, Conn backed away and raised his paws.

"I think I'm a little out of my league here." He tried to laugh, as if he was pulling a joke but ended up choking on his own tongue. Cleo's grin did not fade, rather it softened.

"I can see I'm going to have to go slow with my new boy," she teased. Cleo reached forward, running the curve of her index finger up Conn's throat and under his chin, flicking it softly. It tickled and his heart skipped a beat.

"Cleo, I-"

"Shush-shhussh..." She said quietly before cupping his jawline in both paws and planting a strong firm kiss on his mouth. Conn's eyes fluttered shut. His fur stood on end; his stomach flipped and his heart throbbed... well, not JUST his heart.

Cleo's mouth felt so warm and soft, Conn pushed forward, wanting to get "in" more, to be engulfed in those full pouty lips that seemed to steal away every doubt and every dread in his mind. Whatever decisions he had ever made, whatever screw ups he had been forced to endure, had led him here and this mind numbing kiss. Cleo gave him a gentle push down on the bed, straddling his lap and gripping the back of his head with one paw, stroking his chest with the other. With that soft, roguish smile she spoke volumes; she had complete confidence and control.

She slowly pushed Conn down onto his back, angling both his paws up high over his head, never breaking the kiss. The wolfess started exploring his mouth; her tongue had parted Conn's lips, slipping along his own slimy muscle and probing his teeth. Her boobs squished against his chest and she forcefully ground her crotch right down onto his own trapped bulge, her shorts burning into his denim jeans.

She moved both paws to one of his wrists, still keeping her tongue locked in a wrestling match with Conn's. Her spittle and saliva tasted amazing, mixing with his own and coating the inside of his mouth. The black tiger felt something close around his wrist, tightening hard. Then she moved with quick skill to his other wrist, breaking the kiss to work faster and before Conn had realised what had happened he had been tied down to the bed.

His arms stretched in a wide vee formation, his wrists bound in a nylon stretchy rope, a sensual smooth touch against the skin under his fur. Conn smirked sheepishly and looked down his chest as Cleo straightened up. Her soft smile had been replaced with a cold glare and as she marched over to one of the shelves Conn felt that coldness seep through his pores. Cleo returned clutching a scalpel. Conn's breath froze in chest and he immediately feared the worst, but Cleo simply pulled on the neck line of his shirt and sliced through it, cutting away the fabric and leaving him bare chested.

"Much better," she breathed across his pectorals, blowing a channel of air over one of his nipples. Conn shuddered and squirmed in his bonds. "Klee-klee-Cleo, I-I don't know about th-this?"

"What's to know?"

"It's just... this is all a bit much."

Cleo sighed dramatically, cupping his cheeks in the palm of her paws and squishing them together. "Conn, do you want me?"

Well THAT was an easy answer! "Yes! So much, you're amazi-"

"Well I want THIS, so shut the fuck up and stop turning me off," Cleo snapped harshly, slapping his belly. Conn yelped and whimpered through closed lips. He must have looked pathetic because Cleo caught sight of him and groaned again. She walked around, crouching low behind his head and looked upside down at him, two paws on his curved ears; she thumbed along the rim of his ears, as she showed that very well hidden sensitive side she so rarely advertised to the world.

"Little feisty feline, you don't know what you want."

She spoke so softly, Conn had to strain his caressed ears to hear her.

"Boys don't know what they want... your mind screams in protest as it fights the flutter in your chest, the squirming in your tummy, the throb of your dick," Cleo was almost nose to nose with him now, staring into his eyes, "I can see what you want, so just trust me... you gonna trust me?" She finished on a louder cocky, condescending tone that Conn was so familiar with.

The tiger was taken aback. He KNEW what he wanted... didn't he? Thinking back to the times with Kate his ex, seemed boring. Even when he was "getting boob," or letting her jerk him off, he had always been a little disappointed, thinking "Is this it?" He remembered the half-hearted romp'n'stomp in his bedroom that afternoon where he had lost his virginity and wondered what all the fuss was about.

So the question Cleo had asked was, well, eye-opening. DID he know what he wanted? Cleo's little bouts of kindness instilled a new sense of safety stirring in him and Conn licked his dry mouth. "Sure... I trust you."

"Not that you have a choice," Cleo said, only half-joking. With that, she popped the button and unzipped the fly and then she stuck her paws into the sides of his jeans and yanked them off, leaving him only in his underwear. And then she got her paws on those too.

"Let's see what I have to work with..."

Cleo did not sound disappointed at all, judging by her sigh of satisfaction. Conn's genital was human shaped cock, black like his fur, smooth with shiny cut flesh that smelled of pepper. It was stubby, but very thick. Cleo sat on the corner of the bed, leaning down and resting her chin on her paw.

"Not bad my little boy, not bad at all."

Conn strained against the ropes tying him down as Cleo curled her fingers with patience around the flesh of his cock, pushing the flat of her palm right into the shaft so she could practically feel Conn's pulse. Placing a thumb on his sensitive rounded tip, she moved her paw back and forth, jerking it slowly as if she was playing with a joystick.

Conn arched his back, his sensitive glands filling his brain with pleasure. Her paw was so soft, so warm and so tickly as it hugged his dick in a firm grip, jerking it up and down and occasionally sliding up and down from the base to the tip. His groin, at the base of his dick felt odd with an excited buzzing in his balls. He found himself looking at his dominant.

Cleo's eyes were practically glowing in eager energy.

Conn meowed weakly, his breath quickening as she jerked him. Cleo was skilled, changing her technique just as the tiger was getting used to the adult attention. She stopped jerking and started stroking her paw up and down from tip to base. Every time she reached the base she stretched her pinkie finger out to tickle the little spot between both Conn's furry little orbs. Then she started jerking him in wide sweeping circles. The wolfess started tickling his feet with her fluffy tail, so soft that Conn wanted nothing more than to let the tail sweep over and engulf him.

Conn was starting to sweat, beads squeezing through his fur follicles and sliding down his skin, his fur becoming damp and matted. He was close, so close. He wondered would she let him have his "release." That was a big thing wasn't it, denial of an orgasm or teasing to the point of sexual frustration.

But Cleo kept going, right up until Conn screamed a surprisingly girlish squeal and arched his back in climax. His balls shrunk a little, his urethra stung as Conn pumped out three thick streams of cum. His dick felt so good, he wanted to keep going, harder and harder! Until the climatic bliss suddenly wore off. Now it was beginning to hurt, his flesh sensitive and tired. Cleo mercifully stopped and Conn could breathe happily. She had angled his cock so had coated his own belly and chest in a thick white spray that was mixing into his sweaty fur.

The wolfess shook her paw clean of the sweat that slicked her palm and then dragged to fingers up Conn's middle, scooping up a mouthful-sized blob of thick goopy cum. She got to her feet.

"You're a little pleasure-pet aren't you, barely lasted five minutes." Her cum covered paw hovered dangerously close to Conn's mouth. "Open."

The command was simple and sincere, so much so that Conn only hesitated a split second before opening his mouth and muttering a drawn out "Ah-!" Having never even considered what he tasted like, he was anxious and ready for the worst. It was in Kate's personal codex to stop blowing him a least a minute before Conn ever came, so he assumed he must taste rotten; but it wasn't that bad.

Salty.

That was it, salty and a little stale. Cleo pushed her free paw against Conn's mouth to close around her cum stained fingers. Conn sucked, not even on command. Cleo withdraw her fingers but wasn't satisfied at all.

After Conn had swallowed the mouthful of his own sticky cum with a grimace, she slipped her delicate digits back into his mouth so he could suck them completely clean. Cleo then used her sheets to wipe Conn's chest dry so she could straddle him, her knees on either side of his ribs.

Heat seemed to be steaming off the crotch of her leather shorts, so tight they left nothing to the imagination. Cleo's camel toe was practically teasing him to be touched and the little tiger found himself squirming in his bonds again; something that Cleo was all too happy to tease about.

"Aww, is my little bitch boy getting uncomfortable?"

"N-no... it's just, you're so-"

"We need to fix that," she growled, cutting across him. With a sharp slap to the cheek, Conn shouted out in surprise. "What are you going to call me from now on?"

"W-what?"

"Hmmm, seems my bitch is stupid as he is spineless. You will call me only in the third person as Mistress, or Mistress Cleo. Anything else, even accidentally will result in painful punishment." Conn couldn't help but smile cheekily.

"Heh, you gonna spank me then? 'Cause that doesn't sound like-ARAAGH!"

He roared in pain, blind lights filling his vision and flooding his brain. Cleo had gripped both his little ears and pulled, so hard that Conn was sure she was going to tear them from his head.

"EXACTLY!" she roared, terrifying him. "Spanking is not a punishment. It is turn on for most, a pathetic cliché that sticks itself to the art of domination. No, you will fear my fucking punishment, pet. That I assure you." She released the vice grip on his ears, only to slap him hard in the face and leaving him dazed.

"And now," she said with leer, leaning back to sit down on his groin, forcing his erect cock to bend painfully at the base. As she leaned back she dragged her canine claws softly down his neck, over his collar bone and along his chest, "It's time to truly make you mine."

Conn's ears were still ringing and he blinked back the tears filling his eyes.

"Y-you're going to give me a collar? Mistress!" he added quickly at the end of his sentence. Cleo looked like she approved his quick correction.

"Oh no, that's a given," the wolfess stated. "To truly make you mine I'm going to have mount you and fucking. take. you." Conn's chest swelled, his heart beating faster.

"Mistress, I-I really don't think my cock can take it," he grinned sheepishly. He was only half-joking; his glands were swollen and his balls empty from just the one go, but the idea of feeling the soft wetness of Cleo's sex... he had only even had sex once and the last time he was not a fraction excited as he was now.

"Well then, it's a good thing we'll be using mine," Cleo grinned, hopping off him and stretching out, heading for the shelf of dildos. Conn's heart skipped a quickened beat.

"Wait, whut?"

"Oh my little bitch, to truly take a lesser pet, one must fuck them into submission. Claim them, make them theirs... I'm going to fuck you raw, my little kitten." Cleo's voice practically dripped with vibrant pleasure. Her whole body seemed to be glowing, quivering with anticipation as she paced back and forth the shelfs, searching for toy.

"B-but Cleo-I mean Mistress, I've never had anything um," Conn struggled to explain, "I've never had anything back there...."

"Yeah, a figured you were half a virgin," she said, casually. She seemed to have settled on a sex toy. Cleo turned around, walking back to the Conn, one paw on the base of the toy, the other cradling the tip.

It was light icy blue, the same colour as the splotches on her fur. It looked semi-soft, not rock hard but not at all floppy. It matched Conn's girth and it seemed to be even longer than his, a good seven inches in length. Cleo was looking at him with a reinvigorated life in her energetic eyes.

She laid the dildo down on the black sheets by Conn's ribs, along with what must have been the strap-on harness, a tangle of studded black stretchy straps. Cleo had to position his head awkwardly to get a good look at it.

Despite being a plainly inanimate simple object, it was quite intimidating... the way light caught on its shiny surface; Conn found himself at a loss as he imagined sucking on it, playing with it, sticking it in well, places...

Cleo meanwhile, was changing in the far corner of the room, behind Conn. It was out of his line of sight unless he arched his back and craned his head upside-down; he was light-headed enough without aggravating his condition.

It felt like an hour before she returned. Conn thought he heard the gentle brush of fabric and something dry creaking; a zip being pulled closed; a box being opened. It was impossible to tell, his heartbeat pounding in his ears.

And then she emerged from the shadows to his right.

Cleo the wolfess had stripped her clothing; her shorts and t-shirt were gone but she had kept her the latex jacket, yet all it really did was cover the upper half of her back, her shoulders and arms, and her chest, but barely. The jacket was open and Conn could see the curvature of each fat breast, the nipples hiding underneath the lapels of the jacket.

A latex fingerless glove in black, matching the jacket clung to each of her paws. A pair of thick latex high-heeled boots came up her calves, stopped just below the knee. Finally, she completed the look with a black BDSM styled cap, her eyes just hidden under the shiny brim of the headdress.

She wore that confident smirk that Conn had finally accepted he was falling in love with. It was so breath-taking that Conn barely noticed she was not wearing any pants, anything at all and his heart palpated.

Her legs were standing shut together, shielding her groin but her waist and thighs were pitch black fur with like flecks of bright blue.

"Do you like what you see kitten?" she said so softly, her dry voice cutting the air.

Conn only managed to nod, his dry mouth unable to speak. Cleo didn't chastise him for not answering, in fact she seemed to relish in his reaction. She scooped up the harness in one paw, the toy in the other and slipped it headfirst into a small stiff rubber ring hiding amidst the tangled mess of straps. Then she shook out the harness, finding the leg loops and stepping into them, one high-heeled boot at a time.

Conn watched with a melting mind as she slowly dragged the straps up his thighs, around her crotch and over her behind, buttoning one loop around the base of her tail. She buttoned up other straps, adjusting the tightness around the thighs and waist until it fitted her perfectly.

It was as if it had been made for her, he couldn't tell with the strap-on ended and her groin began. Then suddenly, she was behind him. He was starring upside-down, up her body, trying to look past the stiff silicon dick swaying just above his eyes.

"Open..."

His new mistress didn't need to ask twice. Conn's eyes shut slowly and he opened his mouth, tongue curling out over his dry lower lip to brush his chin. Cleo gripped the shaft of strap-on dick in one paw, holding Conn's cheek in the other and slipped the smooth round tip into his hot mouth.

Conn shuddered as he closed his mouth to seal around the tip of the toy, sucking eagerly. It didn't taste like much, it tasted rubbery and dry. But it was the principle, the idea of it all. Tied down at the mercy of this woman as she held his face and forced her fake cock into his wanting muzzle. She slipped an inch and a half inside, a good quarter of the toy and started to point it different directions.

Playing with his tongue, filling and stretching the insides of his cheeks, tapping his teeth, curiously probing the back of his throat. She pushed her hips forward, forcing him to deep-throat. It took him by surprise, gulping down half the silicon cock as it brushed his throat, triggering a gag reflex.

He panicked momentarily, gagging violently but listened to sound of her shushing him, telling him to relax. Then she pulled away, taking the spittle covered cock with her. Conn couldn't help but be disappointed; thought he knew what was coming next.

Cleo stood between his knees at the end of the bed, watching him with inquisitive eyes. Conn's legs were bent at an angle, his feet-paws on the floor, his bottom just stuck on over the edge of the bed. Cleo took a bottle of lubricant from the shelf, squirting a generous amount to coat the entire shaft of her cock, with so much that it dripped.

With the excess lube, she reached down with two curled fingers, sliding along Conn's sensitive crevice looking for... for THAT!

Conn sucked in a gasp as her fingers found the little raised flesh of his asshole, virgin tight and sealed up. Cleo didn't waste a second, pushing a lube covered fingertip inside without mercy. It stung.

He yelped as she slid the finger it a fraction, feeling up the sensitive untouched flesh of anal cavity. Then she wiggled her digit around, teasing him. Conn groaned, his dick becoming painfully distracting as she fingered his little behind for the first time. Soon she would take him, soon he would be hers!

Cleo seemed to be thinking this too.

She pulled out her finger, most of the lube coating Conn's tight pucker. In a second she had gripped both of his ankles and lifted his legs, like an infant being changed, and rested the backs of his legs against her shoulders. His ass felt exposed and Conn's lower back stretched from his position. But he felt it, he felt her cock sliding up and down between his butt cheeks until finally, Cleo had had enough teasing.

The dominant started probing between Conn's cheeks once again, gauging by his reaction once she had his hole.

The wolfess positioned the tip of the cock right into his anal opening and pushed with pause. Resistance was met of course: Conn squirmed, trying to kick out with discomfort. Cleo simply dug one claw into his thigh, using the other to squeeze her dildo into his ass.

It was slow work. Conn's little tail hole had enjoyed it's last seventeen years, with an easy comfortable lifestyle void of anything the least bit penetrative. And here Cleo came along, thinking she could just waltz in and shove whatever she wanted, wherever she wanted. Well, Conn's tight ring didn't put up much of a fight.

Cleo only had to buck her hips once, twice and three times in quick succession before the rounded lube soaked tip pushed its inside. And once the tip was in... Cleo gave a satisfied humourless giggle as she sunk all seven inches into Conn's rectum.

Conn screamed out in pain and discomfort.

Lube squelched from his asshole when it could, but it was closed so tightly around the thick dildo, hugging the shaft. Cleo put both hands on Conn's hips, keeping his legs up and her shoulders and proceeded to take him, fucking him hard.

She pulled her hips back and forth, bucking like a relentless bronco, in and out. In and out. The pain was intense, his anal fleshly walls swelling to add to the tightness, the once cold lubricant now so hot inside him it felt like it was bubbling.

Apart from the pain, Conn felt very... full?

It was difficult to describe. Even in his heated melting mind, he felt his stomach churning as his digestive system flip-sided with itself, its bowels now full of thick rubbery silicon pumping around half a bottle worth of lubricant.

He strained against the ropes pinning his arms to bed.

He cried out, whimpering again and again until Conn felt Cleo release his right hip only to deliver a painful slap across his muzzle.

"Silence bitch!" She roared, louder than Conn was screaming. He felt somewhat silent, quiet moans of discomfort sounding from sealed lips. Cleo continued to make him her bitch. She fucked hard and fast, her thighs and groin battering against the underside of Conn's backside. Hot lube trickled down his crevice, over the base of his tail and into the sheets.

Whenever he started howling again, Cleo simply slapped him.

Conn reckoned this would have felt a lot better if she had not been so fast, so hard. He was a virgin in this sense; he would have liked a little softness. Perhaps girls felt this way when they lost "it."

Conn continued to squirm, catching little pulses of pleasure every once in a while between the painful throbs wracking his swollen ass. And then... he heard it. Hidden in the deep thuds and thwacks from furry muscle beating on furry muscle, was moaning.

Cleo herself was breathing faster and shorter, gasping every now and again as she threw her groin into Conn's behind. He reckoned the base of the strap-on must be grinding pretty hard against Cleo's bare pussy.

Suddenly the wolfess shook badly, screeching out a wail of ecstasy. She was shaking from head to toe, her face leaning against Conn's ankle as she finally stopped bucking. And now that she had stopped, it didn't felt so bad. In fact, the black tiger found this feeling of fullness to be sensation. The tickle in his anal cavity sent shocks of pleasure up his spine.

With a rest, Conn wanted her to continue. But he was quickly learning once he wanted something, Cleo did the opposite. She slowly stuck her ass out behind her, pulling her groin away and with that, sliding the strap-on out of her newly claimed bitch.

She did it slowly at least, not pulling out half of Conn's insides in the process.

With a wet splattered, Conn's ass dribbled hot lube down into the sheets before sealing up, painful and swollen. Cleo walked over to the shelves of boxes, dripping lubricant from her dildo. She opened one of the lids, peering inside, seemed to think but then shook her head and closed it, moving onto the next one.

Conn just laid there, his insides tickling him and shifting to get comfortable again. So THAT was pegging...

His cock was still as stiff as the dildo that had fucked him, his balls sweating and full, ready to blow again.

"S-so... am I yours?" the boy asked in a throaty cough.

Cleo did not reply immediately. Instead she came over holding an empty box in one paw, the other holding its contents, a green collar with silver studs.

Conn blinked. He didn't know why, maybe it was instinct but he lifted his head so that Cleo could fasten the collar around his neck. It was tight, not to the point of choking but he was very aware it was there.

So, it was official. He was hers.

The clean-up process was a little less fun.

Conn had to use an old rag to clean up the lube puddles on the floor, had to change the sheets on the bed and wash Cleo's dildo off in the sink. He was battered, bruised and tired. He was looking forward to curling up beside her in bed.

Once finished, he leaned against the hallway wall outside the playroom, panting. His ass was still swollen and wet with lube. He was still naked too, Cleo taking his clothes away as he cleaned up.

Conn found Cleo downstairs, waiting by the front door.

"Hey. Mistress!" he added quickly, "Have you seen my clothes?"

"Yes, they're out there." Cleo pointed outside the front door, opening it up out into the night. Conn walked over, nodding and had reached the doorway where his clothes were lying in a heap on the marble porch. He didn't even question what they were doing here...

"Goodnight."

Just as he turned around, the bundle of wrinkled clothing in his arms Cleo slammed the door in his face. Conn stepped back in surprise, his mouth falling open.

"Uh..."

He put the clothes down and knocked, the cold biting at his flesh through his fur.

His knuckle rapped on the hard wooden surface again. No answer. Conn wondered if had made a mistake, done something to upset her. Clearly something had been lost in translation. He waited another fifteen minutes, changing into his jeans and tattered t-shirt and trembling from both the cold and confusion.

When his last knocks went unanswered, Conn sniffled sadly and left the premises. His feelings were hurt; he'd wanted so badly to curl up beside her and she had literally thrown him out. All of sudden his phone buzzed in his jean's pocket.

Conn fished it out, scrolling through Furbook updates and a missed call from his aunt to find a message. He didn't have the contact saved, but he recognised Cleo's number. The text simply said: I'll call you when I want you.

Conn blinked back a tear. Was she so stoic, so cold-hearted? Was she at all normal? Conn had been used before, by Kate but well, Cleo had sparked feelings he never understood. Perhaps he just wished they were mutual. Resisting the urge to throw the phone into the darkness, he set off down the hill to go back home...

To be continued in: The Babysitter: Part III. The Club of Ice and Stone