Punishing the Babysitter

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Carly absolutely loved babysitting for Debbie Anderson’s three year old son. Not only did she have free reign of what she considered the mansion that Debbie lived in, but Brad was a breeze to watch and went to sleep very early, and soundly. Not a bad way to make a few bucks for the twenty year old college student.

Not that Carly wished bad luck on anybody, but when Debbie got divorced the year before, it opened up this opportunity for Carly and she was quick to jump on it. Carly knew very little about Debbie, except that Carly’s parents were friends with Debbie and that Debbie paid very well.

Carly hated the thought of losing this job and normally went out of her way to avoid doing anything to upset Debbie. But one night after Brad was in bed, Carly took an uncustomary ‘tour’ of parts of the house she rarely visited. One wing, in particular, had always piqued her interest.

Debbie had seemingly steered Carly away from the area during their initial walk-through to acquaint Carly with the interior of the house. Ever since, Carly had wondered about the three doors and what they concealed. She decided now was the time to find out.

Walking barefoot to reduce the chance of Brad hearing her, despite the great distance from his room to the mysterious hallway, Carly sneaked toward the first room on the left. A gentle turning of the doorknob allowed it to open without a sound.

Carly pushed the door open just a crack and peeked inside. There was just enough light to let her make out the furnishings of a guest bedroom. Certainly not as exciting as something she imagined from a scary movie, which is what it felt like to her.

She closed the door and moved down the hall to the next room, passing a door on the opposite side in the process. She’d stop there on the way back, she reasoned.

The second room was a den or library. In either case, nothing to run away from screaming.

Carly turned the knob on the third door. It was locked. She hadn’t anticipated this and turned the doorknob two more times to confirm the fact it was locked.

Carly stood in the dimly lit hallway and thought for a second. Normally, she wasn’t the type of person to even consider finding some way to get inside. But something within Carly took over and ostensibly forced her to consider options. The most obvious was a key. But where was it?

She tried to think like Debbie, or any owner of the house. Where would she put the key? The first thought that came to her mind was—the master bedroom. On the dresser, or inside the dresser, of the master bedroom.

Carly knew it was a long shot. Maybe more than a long shot. But she headed for Debbie’s bedroom, entered it, and walked right over to the biggest dresser. Carly studied every object, especially the little jewelry boxes and tiny glass saucer-shaped cups. When she was done, she held four keys in her palm.

With keys in hand, Carly swiftly returned to the locked door. The second key fit and miraculously unlocked the door. Carly was holding her breath as she pushed it open.

She saw no bed. No bookcases or couches. What she DID see caused her breath to finally flow out in a muffled gasp.

Even in the shadows she could clearly make out the manacles hanging from one wall. Hugging the wall under the shackles was what looked like a gymnastic pommel horse without the handles and with a shiny, smooth leather surface.

Carly inched her way into the room, letting her eyes adjust to the dim light. Then she saw the chains hanging from the ceiling with soft handcuffs at the ends. Finally, at the opposite end of the huge room was a bed. But not your typical guest bed. Carly quickly noticed the rope and leather cuffs at the four corners, neatly aligned as if waiting for the next ‘victim.’

Along one wall was a massive dresser that appeared to Carly to be at least one hundred years old. The beauty of the woodwork drew her to it. When she pulled open the double doors, another gasp filled the room.

Inside were multiples styles of whips, masks, dildos and mechanical devices Carly could not imagine the uses for. She stared at the collection in awe.

“See one that interests you?”

Carly yelped with fear and spun around. Debbie stood in the doorway.

“Mrs. Anderson! I’m…I’m…”

“It’s alright, Carly,” Debbie said calmly. “Isn’t it amazing how quietly I can get into this house when I don’t use the garage door opener?”

Carly nodded nervously, almost unable to speak. But she managed to say, “I’m sorry. I just wanted to…I mean, I’ll never do it again.”

Debbie smiled and walked into the room. “It’s OK, Carly,” she said in her most soothing motherly voice. “I would have done the same thing at your age.”

With some of her fears allayed, Carly considered what to do next. Did she ask about the room? Did she just get out as fast as possible?

“I suppose your wondering what the hell this is?” Debbie said first.

“Kinda,” Carly confirmed.

Debbie looked around the spacious room, took a deep Beylikdüzü escort sigh, and said, “You know, Richard was a successful business man who only kept me around as some type of trophy,” she said, referring to her ex-husband. “He displayed me at functions, then totally ignored me when we got home. After he left, I had a few opportunities to meet some…uh…interesting women.”

She watched for Carly’s reaction, and then continued.

“They taught me a lot, Carly. They taught me what sex could REALLY be like.”

Carly felt her heart pounding. All of her first impressions of the room were true, and she couldn’t believe it. This stuff happened in movies and books, but not to her.

“It looks a little weird to me,” Carly said weakly.

Debbie laughed.

“It did to me at first, too,” Debbie admitted. “Then they showed me how it all works and I may never have sex with a man again. At least, not without these aids involved.”

Carly looked into the dresser she had opened with a new understanding of the contents.

Debbie said, “But we have your disobedience to resolve first, don’t we?”

Carly quickly looked up at Debbie. “Please don’t fire me, Mrs. Anderson. Please!”

With a grin on her face, Debbie said, “It’s Debbie from now on. And I won’t.”

“Do anything, but PLEASE don’t fire me.”

Debbie walked over to the dresser. She looked in for a second, and then pulled out a lash with at least a dozen slender pieces of leather hanging from it.

“Maybe I’ll keep you,” Debbie said, sliding the leather across the palm of her hand. “But you need punished.”

Before Carly could react, Debbie hit her lightly in the ass with the whip.

Carly jumped and squealed, “Hey!”

“Shhhhhh. You’ll wake up Brad,” Debbie said. “Now take off those jeans.”

Carly knew better than to refuse, but she wasn’t at all comfortable unbuttoning and unzipping the pants in front of Debbie, or any other woman. Especially one holding a potentially painful weapon. But she slid the jeans down her long legs and kicked them off.

Debbie stared at the small panties tightly wrapping around Carly’s ass and hips and pussy. She gazed longingly at the perfect legs.

“Pull down your panties, Carly,” Debbie said.

“Don’t hurt me.”

“I’ll fire you.”

Carly put her thumbs inside the waistband of the panties and yanked them half way down her thighs, looking at Debbie for some clue she could stop. Debbie was closing the doors to the dresser and continuing to stare at Carly’s half naked body.

“Lean against the dresser, Carly.”

Carly put both palms on the front of the doors, bent over at the waist. She looked back over her shoulder and saw Debbie move up behind her, just off to her side. The whip swung forward and the leather straps hit Carly’s ass all at once.

“Ughhhhhh,” Carly moaned, stifling it the best she could.

Debbie hit her again. And again. The strikes were not violent in the least, but to Carly they felt like a thousand hands coming down on her bare skin. She felt the heat building up inside her body.

“Spread your legs,” Debbie demanded.

Carly was almost glad to be able to steady herself a little more. Then she felt the whip again, with more power behind it with each smack. She was groaning louder and beginning to feel a new reaction—deep inside her pussy.

Then Carly felt Debbie pushing the panties down until they were around Carly’s ankles. Carly lifted a foot and the panties were swept aside.

“You’ll want to be able to move in a few minutes,” Debbie said quietly.

Carly didn’t respond. She watched Debbie get in position again and hit her once more. This time the leather straps hit the inside of her ass and wrapped around until barely scraping against her pussy. Debbie let the straps linger there before pulling the whip back. Each blow brought more contact with her pussy and lasted a fraction of a second longer until Debbie was hitting Carly between the legs from behind and pulling the rubber across Carly’s clit and pussy.

“Oh my God, Debbie. Stop!”

With a knowing smile, Debbie pulled harder after each strike. Carly arched her back and stood on her toes in an agonizing combination of pain and pleasure.

“Stop! Please. I’m gonna…oh God!”

“Your going to what, Carly?” Debbie asked.

Carly could feel the orgasm welling up inside her body as if ten men were licking her clit. She tried to avoid the whip, but Debbie had the answer to every move she made.

“Tell me,” Debbie said.

“You’re going…to make me…cum.”

“So maybe your punishment should be having me stop.”

Debbie held the whip at her side. Carly glanced over her shoulder with a look of total desperation. Her body was nearly shaking.

“No! I mean…don’t…”


“Don’t stop, Debbie.”

With a smile of contentment, Debbie hit her another half dozen times until she was sure Carly was about to explode. Then Debbie put down the whip, moved up behind Carly, Beylikdüzü escort and put her hand between Carly’s legs. Her fingers rested on the soaking wet pussy.

“Do you want to cum, Carly?”

Carly nodded vigorously. “Yes.”

Debbie’s fingers began searching out the swollen clit and wet pussy. She pressed against Carly’s body and frantically rubbed the clit until Carly began panting loudly and moaning unintelligibly. Debbie rammed two fingers inside Carly’s cunt for a moment, then returned to the clit.

“Yes! Yes! Ohhhhhh God, yessss!”

Debbie pinned Carly against the dresser and masturbated her into the longest, loudest, most intense orgasm Carly ever had. Carly’s fingers grasped at anything they could find to steady her as the orgasm swelled, faded, and started over again with renewed attention by Debbie. The dresser rocked as the women pushed against it and Carly came over and over again.

Finally, it was over and Debbie backed away from her ‘victim.’

“You’re a naughty girl, Carly,” Debbie said. Carly leaned her head against her arms and didn’t look back. Debbie watched Carly’s heavy breathing and felt her pussy react to the sight. “Your punishment will have to continue the next time you’re here.”

Carly slowly turned to face Debbie.

“What do you mean?”

Debbie paused and seemed to think for a second. “The next time you babysit for me, when I get home I want you in this room. You can choose any item you want. The bed. Anything in the dresser. You decide. Just be ready for me when I get here.”

Carly nodded, unsure whether to cry or cheer at the options.

“Oh. And you must be naked,” Debbie added as she left the room.


The next couple days left lots of time for Carly to contemplate what happened in Debbie’s secret room. In fact, it was ALL she thought about. Every time she tried to condemn herself for allowing it to take place, she ended up dwelling solely on the intense pleasure she enjoyed.

Carly recalled each slap of the leather lash and the shockwaves they sent through her body. She could feel the straps dragging across her pussy like a thousand fingers, clutching at her clit and causing her to get wetter and wetter.

She remembered the overwhelming desire for a man’s cock inside her pussy. But it wasn’t a cock that got her off. It was Debbie’s magic hand. It was a woman’s fingers that made her cum and a woman’s voice that added to the delight.

Carly could still feel Debbie’s tits pressed against her back and how it excited her.

‘What is wrong with me?’ Carly thought to herself.

She wondered what would happen the next time she babysat for Debbie. Would there be a next time? Could she do it? Could she make herself say ‘No’?

She knew, deep down, that she couldn’t refuse and when the phone rang one night and Debbie asked her to sit the following Saturday evening, Carly said ‘Yes’ without hesitation. Debbie only reminded Carly of the agreement one time. She hardly needed to.

The mixture of fear and anticipation was something Carly had never experienced before. It was better than drugs. This was real. And it frightened her in an addictive manner.

Saturday came quickly and Carly found herself alone with Brad in Debbie’s house before she had any more time to reconsider. Once he was in bed and seemingly asleep for the night, it struck Carly that any moment could be the one she’d spent so much time thinking about. She paced aimlessly and flopped on the couch. But she never paid attention to the TV. Her mind was on the room…the dresser…and the bed. Images of the leather horse flashed through her mind. She felt her panties getting wet and her nipples hardening.

Carly rose to walk into the kitchen. Then, she heard it.

The garage door was opening.

With a gasp, she ran down the hallway and entered the room. She left the door halfway open and quickly started to undress. Tossing her clothes into the corner, she moved to the bed. Taking only a few seconds to move the handcuffs aside, she fell into the bed. Then, she nervously fastened one set of the padded cuffs on her left wrist. Minimal dexterity was required to fasten the cuffs on her second wrist, and Carly was almost ready.

She squirmed her naked body on the covers to center herself on the bed and looked over at the door. She couldn’t hear anything, nor see any shadows in the hallway. She tugged on the cuffs to make sure they were secure and peered down the length of her nude body. Carly felt incredibly vulnerable, and sexy.

The sound of steps in the hallway finally convinced her there was no getting out of this.

Debbie appeared in the doorway, a devilish grin on her face. She was wearing a red dress with spaghetti straps and a plunging neckline. Carly’s pulse quickened and she unconsciously pulled her legs a little closer together.

Debbie stepped into the room and pushed the door shut, never taking her eyes off the nude woman on the bed.

“You really must want this job,” Debbie said. Escort Beylikdüzü “Very nice.”

She walked to the end of the bed, staring down at Carly’s legs.

“But you missed two of the cuffs.”

Debbie ran her hand down the shin of Carly’s left leg, slowly caressing the ankle before sliding her fingers over the top of the foot. Then she fastened the cuff from the end of the bed around Carly’s ankle. A minute later, the other leg was secured and Carly began to understand the potential consequences of her position. She was completely spread open for Debbie to do whatever she pleased and Carly had no means of stopping her.

The contents of the dresser flashed through Carly’s mind, but Debbie quickly answered as if she knew what the woman was thinking.

“I think this first time,” Debbie said unhurriedly, “we should forget the toys and simply enjoy your luscious body. What do you think?”

Carly nodded, her throat too dry to speak.

Debbie walked to the side of the bed, not touching Carly but inspecting her with her eyes. After what seemed like an eternity, Debbie removed her shoes. Carly watched as Debbie’s tits pressed against the inside of the dress, apparently unrestrained by a bra.

Then Debbie stood up and ran her fingers over her dress from the side of her tits all the way down her body until the dress stopped just above the knees. Every incredible curve was highlighted and Carly felt her pussy start to react.

Debbie was looking Carly right in the eye when she reached back and pulled down the zipper. As if in slow motion, Debbie took the two straps and inched them over her shoulders. She let the dress dangle with both nipples barely covered by material. Then she allowed each tit to slowly uncover until Debbie was holding the dress up at the waist.

Carly couldn’t take her eyes off the gorgeous tits. They were smaller than Carly had envisioned, but the perfect shape and erect nipples made up for it. She only had a few seconds to appreciate them before Debbie began to lower the dress, revealing a lacy pair of panties. Finally, she let the dress fall to the floor.

Carly watched her step out of it and adjust the panties with a graceful movement of her hands. The thin material did little to hide what was underneath and Debbie didn’t make Carly wait long to reveal the neatly trimmed pussy. Debbie bent over to remove the panties, giving Carly another lovely view of her tits and ass.

Debbie knew from her own experience that somebody new to this type of sexual pleasure needed as many visual stimulants as possible to help ease them into action. She provided Carly with many, lingering after each one before proceeding to the next level. Now, it was time to see if Carly was ready.

Debbie leaned over the bed and said, “You look incredible, Carly. Good enough to eat.”

Debbie’s hands moved up to Carly’s tits. She caressed them lovingly and ran her palms over the nipples. Her fingers slowly wrapped around the youthful flesh and faintly squeezed the tits. Only when Debbie pinched the nipples did Carly show any reaction. Debbie saw her entire body tense up and gradually relax again.

After a minute of this manipulation, Debbie bent over and ran her tongue over the nearest nipple. She heard the straps holding the handcuffs clatter as Carly responded once more. Debbie sucked on the tit a little harder and bit the nipple with her lips. Carly’s eyes were closed. She winced and arched her back. She thought her pussy would explode with each bite.

Debbie began kissing her way down Carly’s body, past her navel and stomach. She had the answer to her question of whether Carly was ready or not even before reaching the pussy. She could smell Carly’s body preparing for whatever Debbie had in mind. Debbie smiled to herself and teasingly kissed all around Carly’s clit without ever touching it.

“Since this is still part of your punishment, I think you’ll have to wait,” Debbie said. Carly thought twice about begging, deciding she was in no position to barter.

Without saying anything else, Debbie started to climb onto the bed. Carly watched her swing a leg over and straddle Carly’s body at about the waist, facing the captive young woman.

“Since your hands seemed to be a little, uh, ‘tied up’, I guess you’ll have to use your mouth,” Debbie said.

With that, Debbie leaned down and put a tit just above Carly’s lips, which parted without further orders being necessary. All of this was new to Carly and not exactly solicited. But she found herself somewhat anxious to taste another woman’s breast for the first time. When she felt the nipple on her tongue, she closed her mouth around the soft skin.

Debbie closed her eyes, tilted her head back, and just enjoyed it. With each passing second, Carly sucked on her tit with a little more energy until Debbie felt her pussy tingle. Debbie waited for Carly to take a breath before switching to the other tit. At the same time, Debbie reached down and began massaging Carly’s breasts.

After a couple minutes, Debbie slid backwards and leaned down to kiss the young babysitter. Carly accepted it and their tongues fought for space. Soft moans filled the room by the time they were done.

“I think it’s time,” Debbie said softly.

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