Fantasies of a Babysitter Ch. 01

Hi, my name is Cindy. I'm a twenty year old college student living in Southern California. Now you might think that it is odd that someone as old as I am still babysitting. The truth is I'm good at it. I'm dependable, take good care of the kids and am usually always available, even with short notice. I could get a job at school, fast food or retail, but I find that I make more money babysitting (and tax free). I end up making considerably more then minimum wage; my tips are pretty good, especially when I take a job on short notice. Most of the people I baby-sit for are wealthy so their time is a lot more valuable then mine, so they tend to tip and pay better.

I guess you can say that I'm pretty, just not beautiful. I have brown hair, where most in Southern California are blonde. My breasts are rather small, where bikini's and abundant cleavage are the norm. You could stay that I don't stand out. I guess my best asset (a play on words) is my ass. I do work out; most of the people I baby-sit for have gym equipment. My cheeks are firm and tight. If I had more nerve I would look great in a pair of short shorts.

I don't date much, hardly at all. My problem is I am shy, really shy. Especially with boys. I'm not a virgin, having lost it when I was sixteen. I'm sure you will be surprised to learn that it was with two boys at once. Hardly the romantic way you would think. They were both older, 20 year old college students. Not what you would have expected from me? That is another story. Let's say that I still have fond memories, bringing about a delicious orgasm each time I think about it while masturbating.

Yes, I masturbate. Masturbate a lot. I have a very vivid imagination and as I blossomed into girlhood, my imagination became more sexual. So I masturbate, there is nothing else to do unless you want me to run around horny. Now I know you boys would love that. But you don't have a 4.0 average in college if you're perpetually horny. It's tough to masturbate when you live in a dorm, so my babysitting jobs also have an added incentive for me. Once the kids are asleep at night I have lots of time to let my imagination run wild, my hand in my jeans rubbing my pussy until I cum.

Now to my story. I have been reading Powerone stories for a long time, loving his tales of submissive girls. One day I sent him an e-mail which he answered. We sent back e-mails a couple of times until I started telling him of my fantasies. He liked them and thought they would make a good story. I would tell him one of them and then he would write it. He is much better then I am and much more perverted. Since he put them down on paper, my orgasms have been much better. Only he could have thought of the things that were done to me in the fantasies. None of these really happened; they are just figments of my very fertile imagination. So here it goes.

Chapter One Naughty Girls Get Spanked

Mr. Johnston, Michael as he asked me to call him lived in Rancho Santa Fe. He has a five year old daughter and a very attractive wife. They are very wealthy. I baby-sit for him often, Michael appreciating it with very large tips, especially when I do it on short notice, which is often. Their house is always immaculate, I'm sure they have a maid that does it, but he is very picky about it. I make sure that I leave it that way, spending about the last half hour before they get home picking up and cleaning.

I was babysitting them last Friday night. It was about ten o'clock when I heard a noise. It scared me because the Johnston's were not supposed to be home until after one. I was laying on the couch, a drink and some potatoes chips on the table, reading one of my textbooks. I jumped up when I head the click of the door and a noise in the front hallway. Now this is a big house, so it took me a while before I managed to get to the door. And I was peeking around the corner when I saw Michael. He looked a little angry and he was alone. I was relieved. At least it wasn't a burglar.

"You scared me Michael," I said as I peered out from around the corner. "Is everything okay?"

"Everything's fine," he said gruffly. "I came home early; Lillian decided to stay for a couple of more hours. Is the baby okay?"

"She's sleeping. Let me get my things and I will go." I remembered the mess in the living room. I would just clean it up real quick and get out of there. He didn't look very happy. Maybe he had a fight with Lillian.

"What is this?" He stared at the mess on the table, potatoes chip crumbs on the floor. His voice seemed even angrier.

"I was just going to clean it up. I didn't know you were coming home early." His rage seemed to be directed at me. I had never seen him like that. "I'm sorry," I quickly added.

"Being sorry wouldn't cut it today. You know how much I like my house clean. I didn't mean for you to mess it up and clean it up before I come home. I expected you to keep it clean all the time. I expected much more from you Cindy."

He was looking at me a bit strange now. It was a mixture of angry and something else; I wasn't sure what it was. "I understand Sir. It wouldn't happen again."

"I think you need to be taught a lesson. If you don't want to accept, you are free to leave and I will find someone else to do your job. Somewhere more willing to take responsibility."

Cindy started thinking quickly. She was making over $800 a month babysitting for them. A quick calculation showed that her tips were often very big, earning her about $20.00 an hour. God, how could she ever replace that? She also got two other jobs because of Michael. Would he tell them about her? Would she lose them also? Taught a lesson. What did he plan to do? She looked at him, his anger seemed to be going away quickly, but there was a different glint in his eyes. He was looking at her strangely, eyeing her body uncomfortably. Could he mean something sexually? She began to feel dampness between her legs. "No sir. I'm willing to take responsibility." There, she said it, almost feeling a relief.

He smiled at her. "That's much better." He moved over to one of the chairs, sitting down on the straight back chair. "Do you know how naughty girls are punished?"

"No Sir," but she knew she was about to find out. He beckoned her over to him. She let her hands slide down to her side, clutching her short skirt to her hips.

"I think a spanking is in order. Maybe if your lovely ass cheeks are sore it will remind you to obey."

"Spanking! You're going to spank me. I'm too old for that." But she saw in his eyes that he wouldn't take no for an answer. She trembled as she moved closer to him, his hands already outstretched to touch.

"Turn around." His voice was firm and demanding, making sure that Cindy would submit. His cock jerked in excitement as her cute ass turned towards him, her head hung in shame. He felt her body tremble when his hand touched her hips, jerking forward as if she were burned.

"No!" She cried out when she felt him touch her. She tried to jerk away, but his hands became more insistent, pressing harder into her hips, pulling her back towards him. Her hands went back to protect herself.

"Don't you dare! Put your hands in front of you." He pulled one hand free and slapped her hard on her upper leg, the sound of his hand hitting her naked flesh ringing out in the room. "Stand still!"

Her leg stung from the blow, catching her off guard. It still felt as if his hand was still touching her there, the skin hot and aching. She moved her hands forward, but not before she touched the spot he had hit, feeling the hot, tender skin. "Please," she could only beg. But she obeyed him, her hands hanging submissively at her side, waiting. Waiting for the touch of his hands on her body again. She didn't have to wait long, the hands returning to her hips, firm, strong hands that pulled her back towards him. At least she didn't have to see his face.

He enjoyed the way she obeyed, standing, waiting for him to make his next move. He let his hand begin to slide down her hips, her short skirt highlighting the long tanned, naked legs. She shivered when he touched her skin, his hands clenched motionless as she grew accustom to his touch. He slid back up, his hand sliding under her skirt, caressing her naked flanks. Her skin was so silky smooth. She didn't even flinch when his hands slid under her skirt, reconciled to the fact of his power over her.

She couldn't believe it when his hand slid under her skirt, her body frozen as he ran up her naked hips. His hands slid up high, her thong doing little to cover her naked body, his hands freely exploring her body. She almost forgot that her ass cheeks would be bare, not even flimsy panties would stop any of the pain of the spanking. She felt a sense of relief when he moved his hands from under her skirt, but they returned, this time on her skirt, but starting at her waist and moving down the gentle slope of her butt until both hands gripped her cheeks. He squeezed the taut cheeks, Cindy tightening her buttocks in response, his hands powerful, gripping her flesh tightly. He clenched and unclenched her cheeks in his hands.

He loved the feel of her naked skin, pleased that she was wearing a thong; her lovely cheeks would be naked when he pulled up her skirt before spanking her. Her delicate flesh would feel the entire brunt of his large hands spanking her cheeks. He gripped her cheeks with his hands, loving the way she fought the intrusion, her cheeks tightening in response. He would use that against her; let her feel what happens when she tightened her cheeks later, a surprise that she could never have expected. "Your ass is built for punishment Cindy. Nice, full round cheeks. I'm going to turn them a delightful red." He released her cheeks. "Over my lap now. It's time to begin your punishment."

Her face was already red in shame at his fondling of her flesh, but she was unable to stop him. He touched her as if he owned her and she let him have his way with her. That is what scared her so much. How far would she let him? How far would he go? She hesitantly moved closer to him, blushing as she saw the bulge in his pants. She was exciting him. His arms came out and gripped her waist, pulling her until she was standing to the side of him, his arm pushing down on her back as he bent her over him. She could feel her breasts hanging down; glad he at least couldn't see down the front of her open blouse.

He let his hand stroke down over her outthrust butt, his other hand on her back, forcing her to bend over onto his lap. "Yes," he moaned in pleasure as her body touched his throbbing cock, feeling the flesh quiver in lust. He let his hand roam over her ass cheeks, her skirt riding up as he forced her into position. He enjoyed her squirming, his cock receiving such a delightful rubbing. He couldn't believe how submissive she had become, resigned to the fate of a spanking, or more. His hands enjoyed her tight ass, massaging the firm flesh while she squirmed beneath him, not even fully understanding the delightful masturbation her squirming was giving his hard cock. He made his cock jerk twice; her body stopping as she fully understood what she was doing to his cock. He slapped her one cheek hard, the sound of his hand hitting her tight ass ringing out in the room. "Don't stop squirming!" His voice was firm.

She felt the cock jerk against her, suddenly the realization of what she was doing to him dawning on her. Not only was she masturbating him with her body, but also herself, her pussy getting wet as she rubbed against the hard cock. She was almost humping him as if she were a dog in heat; all the while his hands were molesting her flesh. She stopped instantly, ashamed at the way she was acting. "EEEEHH," the slap of her ass stung. She could feel the pain even after he removed his hand. He wanted her to continue, to masturbate his cock with her pussy by rubbing up and down. How humiliating to be treated as just a sex toy, but she couldn't deny the tingling she felt between her legs, the way her clit seemed to rub against his cock. She began to rub against him again, squirming her lower body back and forth over his cock, feeling it jerk in pleasure as she began the gentle masturbation of his cock again.

"You learn well Cindy. You just need a little physical pain as encouragement to make you perform." His cock jerked again from her artful squirming, noticing a change in her. She seemed to be enjoying the movement of their bodies rubbing against each other. Even his cock jerking didn't slow her down; in fact it made her move quicker. His hands ran freely over her luscious cheeks pushed out on his lap, his other hand on her back keeping her pinned down. Her skirt had ridden up high on her legs, barely covering anything now. He began to lightly slap her naked legs, moving from her knees up her inner thighs, pushing out on them, forcing her legs to part slightly. While his slaps weren't very hard, they were consistent, moving up and down the same tender inner skin, turning the skin pink. He couldn't wait any longer, eager to see the taut naked ass that lay beneath her tiny skirt. "Reach back and pull up your skirt. It is time to spank your ass. Your naked ass."

It was humiliating enough to be forced to masturbate him all the while he slapped her tender inner thighs, the burning increasing as he continued to slap the same spots over and over. Now he wanted her to uncover her naked ass so he could spank her. The thought of him seeing her naked body, afraid of where it would go from there. Afraid of where she might allow him to go. Her pussy was drenched, his hard cock bringing such a delightful sensation as she rode her slit up and down the throbbing member.

"Now!" She seemed to be daydreaming, a sharp slap to her ass bringing her back to reality. She stopped moving as her hand reached back and submissively began to draw the tiny skirt above her waist, letting it fall onto her back, her hand returning to prop herself on the floor, her lower body beginning again the gentle masturbation.

She felt the cool air of the room on her ass, knowing how exposed she must look. She closed her eyes, her fantasies clouding her mind as she rubbed against him again. She tightened her thighs and cheeks, hoping to keep him from seeing her naked sex. She felt the rush of air before she even felt it. A sharp slap sounding in the room, then the rush of pain as it shot to her brain. God, it stung so badly, much more then she remembered as a child. Another to her other cheek, the skin feeling so hot and tingling. She tightened her cheeks even harder as his hands began to explore her naked ass, a finger trying to slide between her tightly clenched cheeks, moving up and down her crack. She wouldn't allow him access to her most guarded treasures.

Each time he spanked her, her masturbation became more urgent. She was enjoying the pain or the submission, not caring which, just enjoying her enthusiastic masturbation of his cock. But he needed to have her submit to inspection of her most private treasures, her clenching thighs and cheeks preventing it. "Get up and go to the kitchen. In the refrigerator crisper you will find a ginger root. Do you know what a ginger root looks like?" He was counting on her nativity, hoping she wouldn't realize the purpose.

She felt his hands pulling her up. Why did he want a ginger root now? She was confused, but she obeyed, her skirt falling back down to cover her naked buttocks. "Yes Sir."

"And bring a paring knife. Now hurry back. You still have your punishment coming." He watched her ass sway so sensuously as she left the room, unaware of what lay ahead for her. He heard her in the kitchen, quickly bringing back what he requested, her face red in embarrassment at having to face him. "Good girl." He had arranged the coffee table in front of the chair, a few pillows for cushioning on top of it.

She handed him the ginger root, a large root about an inch in diameter. She knew it was used in gourmet cook, not understanding why he wanted it. But that is what she feared.

"Turn, your back to me," he ordered her. She obeyed instantly, his hands reaching out to grab her hips. "Move back," pulling her backwards. "Spread your legs," he ordered when she bumped into him.

She was afraid of the last order. Spread your legs, her face red in shame as she slowly did as he requested. She felt her body being moved back until she was straddling him, her legs on either side of his hips. She almost had to bow her legs out to accommodate his request. She felt his hand on her back, pushing her down again. Now she understood. Her ass rose up as she was pushed down, down towards the cushioned coffee table. His hands were on her naked hips, having slipped under her skirt again.

"Put your hands on the table. I'm going to lift your legs up. Spread out on the table." His hands eagerly slid lower down on her legs when her body touched the table, supporting her. He pulled her up until her body was positioned on his lap, her legs now hanging uselessly behind him. She looked back, her face red in shame as she finally realized how vulnerable of a position she was in.

How did she get in such a position? She was almost lying on top of him, her lower body supported on him, his hard cock pressing into her sex again, this time with her legs spread, she was so much more vulnerable. She felt his hands returning to her legs, sliding underneath her skirt, moving up to her naked ass. "Please no," she begged as she felt her skirt pushed up higher and higher, moving up until she felt his hands on her naked ass cheeks, knowing the view that she was affording him.

He let his hands slide up her inner thighs, feeling her muscles tighten, as he got closer and closer to her sex. With her legs straddling his body, she couldn't stop him from exploring her sex. He pushed her skirt until it was on her back, her luscious ass revealed in all her naked glory. His hands began to explore her lovely flesh, moving back and forth her cheeks, feeling her tighten when he moved closer to her crack, teasing her by sliding one finger up and down the moist opening, her cheeks pinned tightly together as she sought to hide her treasures from him. His fingers moved to her crack, his thumbs on each side, digging in and pushing out. He heard her moan as she tried to prevent him from pulling her cheeks apart, his fingers too powerful, finally relenting with a grunt. The string from her thong still hid her asshole, but he could make out the edges of the dark brown wrinkled opening, his finger sliding so close to it that he saw the edges pucker in and out. He slapped her ass hard, her body jerking up in pain. His hands moved to her hips, making her body move, making her masturbate his cock again with her pussy. "Continue."

He was going too far now, teasing her too close to her asshole. Why would he want to touch her there? His powerful slap stung fiercely, his hands urging her to squirm on his cock again. She knew it must look as if she were a two dollar whore, humping him with her pussy, but she obeyed, her pussy wet with desire. His hands stopped touching her, her eyes closed as she heard movement behind her, too scared to look back.

Michael began to prepare the ginger root. What Cindy didn't realize is that the ginger root produces a burning sensation when introduced into the anus. It is used to humiliate and chastise the victim, as well as preventing the victim from clutching her buttocks during spankings, the pain increasing when the ginger root is squeezed by the sphincter. The burning sensation is also known to induce intense pleasure. He used the paring knife to skin the root so it was smooth. He carved a concavity around the finger of the root about two thirds of the way down. This acts as a retention device, similar to the way the tapering portion of a butt plug is locked by the sphincter. Cindy would be experiencing some very new and uncomfortable feelings in her anus, hopefully adding to the squirming she was doing on his cock. He didn't need any lubrication, the natural juices of the root more then sufficient. First he had to prepare her, knowing that she would fight any intrusion into her anus. A brief spanking and then a gentle masturbation would suffice.