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Fantasies of A Babysitter

Chapter 2

Powerone

Copyright 2005

One of my best jobs is to house sit.  No kids to take care of just stay at someone’s house for a couple of days.  And these are not just ordinary homes, most are multi-million dollar homes at the beach.  Last week I was house sitting one of my favorite places.

Let's just call him Bill; I wouldn't use his real name.  Bill used to be a movie star about ten years ago.  Very famous.  He did quite well and just retired from entertainment, having been very successful in business.  He travels a lot for business, so I get to house sit for him quite a bit.  He pays well and I get to work on my tan.

And by the way, Bill is the most gorgeous man I have ever seen.  He's only about mid forties, a deep tan, works out in his own gym and takes great care of himself.  I've seen him with a lot of women, sports stars, movie stars, socialites, all gorgeous.  But Bill is still single, not sure why.  I would let him in my panties in a second!  Okay, maybe I wouldn't.  I told you, I don't date much, but masturbate a lot.  Shy thing I guess. But back to the story.

I stay in one of his guest rooms.  It's a massive room the size of my parent’s whole house, one glass wall overlooking the Pacific Ocean.  And the bed.  A massive bed, overstuffed mattress, satin sheets and comforter.  The only way to sleep in satin sheets is naked.  So I do.  This week was finals, a tough week of studying to the wee hours of the morning, finishing the last one this morning.  Bill was to be home tomorrow morning, so I climbed into bed early, my naked body sliding along the satin sheets.  God, I almost came as I got in.  Now I've been extremely horny this week, not having much time to masturbate.  I lay on my stomach and rubbed on the satin sheets, feeling my hard nipples slide along the material, rubbing them so sensuously.  I could probably cum just by rubbing them, but I was just too tired tonight.  Even as horny as I was, I fell into a quick deep sleep as soon as I touched the pillow.

Bill walked quietly into the house, noticing that all the lights were out, hoping that she was asleep.  While Cindy wasn't as beautiful or sophisticated as the women he dated, there was just something about her that always drew her to him.  He had finally figured it out.  It was her lips.  His cock seemed to spring to life each time she opened her mouth.  The only thoughts that raced through his head was what it would be like to feel her hot breath blowing on his cock, her wet tongue racing over the head or her silky lips wrapped tightly around the head of his cock.  He could hardly think of anything else when he saw her.  He had seen the way she looked at him, hoping that he was right, hoping that she would do anything for him.  His cock throbbed at the thought of her sucking his cock.  He crept toward the guest room, quietly opening the door.  The room was partly lit by the full moon, the drapes open.  He could see neatly tucked under the comforter as he moved closer towards her.

His cock jumped in his pants when he saw her.  Her head was on the pillow, her mouth open as she slept so quietly.  He could hear her gentle breathing, her lips slightly moistened.  He watched her for about ten minutes, seeing her tongue come out and swipe at her lips, her lips glistening in the moonlight.  He couldn't wait any longer.  He slowly slipped out of his clothes, his breath ragged as he indulged in his fantasy.  His hand went down to his cock, gripping it tightly as he stroked it up and down.  God, he had to have her mouth soon, before he came all over the bed.  His naked body moved quietly to the bed, kneeling on the edge, holding his breath as he waited to see if her body moved.  She didn't stir, so he slid over towards her.

He moved his hand closed to her face, only inches from her moistened lips.  He held his breath as his finger lightly ran over her lips, her eyes seem to flutter but not open.  His cock jerked in excitement as he felt her soft lips for the first time, the thought of them touching his cock exciting him.  He ran his finger around her lips, pushing into her open mouth, her tongue touching his finger in reflex.  He let his finger slide inside her mouth, Cindy still sound asleep as he moved deeper into the hot recesses of her mouth.  God, he couldn't wait much longer.  She still didn't stir.  He moved next to her head, kneeling only inches from it.  He stroked his cock as he lowered his throbbing member until he felt her lips touch his cock.  "GGODDD," he moaned too loudly as he felt her lips touching his cock. He saw the head of his cock leak out pre-cum, eager to pump his cock in her mouth and fill it to overfilling.  His cum glistened in the light on her lips as if it were a lipstick.  His cock jerked in pleasure, her head turning slightly as it bounced on her lips.

Cindy was having one of her erotic dreams.  This one even more vivid then the others.  She was dreaming of the time when she was younger and had sex with the two older boys.  It was one of her most reoccurring dreams.  The difference in this one was that one of the boys was trying to get her to suck his cock.  One was between her legs, his hard cock sliding in and out of her recently violated pussy, the other was rubbing his slippery cock all over her face, a trail of his cum clinging to her skin as me moved it back and forth.  Hands tilted her head back, Cindy submissively opening her mouth in response to the strong hands urging her to perform the task.  She had always been afraid of perform such a loathsome act, needing to be forced to accommodate the act that she thought was so degrading.  The dream was so real, licking her lips, the salty taste quickly basting her mouth.

Bill could see her eyes beginning to flutter as she moved.  Her mouth seemed to be opening, Bill not wasting any time, taking advantage of the situation to let his cock rub around her lips, his cock jerking in pleasure as he did.  He saw her stir, knowing that she was wakening, the moment of truth upon him.

"Don't open your eyes," he said in a deep, demanding voice.

Cindy was suddenly brought back to reality by the familiar voice of Bill.  She was awake, her eyes still shut, quickly realizing that the dream of hot, hard flesh on her lips wasn’t a dream, she could feel it sitting on her lips.  She heard his command, not wanting to open them, afraid of confronting the reality of the situation.  Did he really have his cock on her lips?  She squeezed her eyes tighter, her only response to his command.

"Do you know what I want you to do?"  He moved his cock from her lips, letting it rest on her cheek, the cock jerking against her silky skin.

"I've never done that before," was the only thing she could answer.

His cock leaped in joy at her response.  It wasn't a denial, more of a statement of her intentions to perform.

"I'll teach you."

"Yes Sir," she muttered.

Bill picked up the black mask that be brought.  "I'm going to put this mask to cover your eyes so you don't have to squeeze your eyes tight.  Lean your head forward so I can put it around your head."  It was an order, not a request.

So he'd planned it, the mask ready.  How did he know she would submit?  She shivered when his fingers touched her neck, sliding the mask down until it covered her eyes.  She opened her eyes, confronted by the darkness of the mask.  She waited, not sure what to do.  She felt the hot flesh touch her cheek again, his hand pushing her face softly towards it.  She could feel it throbbing against her skin, almost feeling as if it were burning her flesh.  She kept her lips closed as he slid it across her lips, her tongue instinctively coming out, startling her as she suddenly came in contact with it.

"No, don't stop.  Open your mouth and stick out your tongue.  Your lips are so inviting, my cock is throbbing to feel your lips wrapped tightly around my hot flesh."

She couldn't believe that Bill desired her.  He had often looked at her, but not like she looked at him.  She had even imagined him taking her body one night, but the thought of him taking her in her mouth was something she could never have fathomed.  She was always disgusted by the thought of taking someone's cock in her mouth.  Even worse the thought of having it fill her mouth with cum and being forced to swallow it.

"Are you going to cum in my mouth?"  She had to know.

"Yes.  And you're going to swallow it."

"Yes Sir."  She didn't know if she could do it with choking, but she knew she wouldn’t have a choice.

"You're going to have to take my cock deep in your mouth. Once you get use to it, I going to push it into your throat where your throat muscles will give me a very enjoyable fuck."

"I'm afraid I'll choke and gag if you do that?"

"I'm counting on you doing that.  That's what makes it so enjoyable.  If you are a good girl, I'll let you masturbate while I fuck your mouth."

The thought of him making her take it in her throat sent a shiver down between her legs.  The thought of his hands on her head, forcing his cock into her throat while she gagged and choked excited her.  Now he wanted her to masturbate while he fucked her mouth.  "Under the covers Sir?"

"No, I want to see your naked body and watch your fingers play with your pussy.  The thought of watching you cum is appealing to me, to see the expression on your face as you orgasm for me, your mouth filled with my cock.  Hopefully I can cum at the same time, seeing your cheeks bulge out as I fill your mouth with my cum."

"I don't know if I can do that Sir."  Her mind quickly filled with pictures of her legs spread, her pussy wet as her fingers played up and down her slit, Bill instructing her what to do as she sucked his cock eagerly, holding her breath as she waited for the inevitable time when he would cum in her mouth.

"It wasn't a question, Cindy.  You will masturbate your pretty little pussy while you suck my cock.  I wouldn't tell you again."

She felt his hand tighter on her head.  She could only murmur, "yes Sir".  She opened her mouth; her tongue slowly began to stick out, almost afraid of what she would find.  Suddenly she felt it, the hard, rubbery head of a cock.  She pulled her tongue back, then pushed it out again.  She could already taste the salty flavor, knowing that it was his cum.

He liked the way her tongue moved tentatively, barely touching his cock, his throbbing member jumping in appreciation at her wet tongue finally reached out and touched it, then shooting back into her mouth.  "Yes, good girl," he complimented her as her tongue moved back out again.

It felt strange, his cock so hot.  It was hard, yet rubbery, a different texture then she had expected.  Her tongue moved again, this time not pulling back, lightly rubbing along the thick head.  She felt it jerk as her tongue moved in a circle, feeling the hole in the center, resting the tip of her tongue on it.  She could taste the fluids that her tongue had coaxed out, a thick texture, salty, not all together unpleasant but just a small amount seemed to spread quickly inside her mouth.  She let her tongue run down the side until she felt the ridge around the head, imagining the large red helmet that was the head, running her tongue all around the edge, the tip of the cock rubbing against her cheeks as she did.

He enjoyed the way she seemed to be exploring his cock with her tongue.  Would she be so willing once she started sucking his cock, taking it in her mouth?  "While I am enjoying your tongue Cindy, it is time for you to wrap your lips around my cock."

She opened her mouth wide, his hand under her chin, lifting her head up until she felt his cock touch her lips again.  She waited until she felt it, his cock sliding along her lips, slowly and sensuously entering her mouth.

"What a lovely hot mouth Cindy, your hot breath is almost making me cum."  He pulled her forward more, eager to feel her lips around his cock.  "Close your lips on my cock.  Make it nice and tight, just like your pussy."

She let her lips close, grasping the hard cock in her mouth, her lips capturing it just below the rim, the thick helmet of his cock inside her mouth.  It felt strange and exciting, being forced to take his cock in her mouth.  Not like she thought it would be like, not as distasteful as she remembered.  Maybe it was the slow buildup, his teasing her as she lay there, the darkness of the blindfold making it as if she had no choice but to submit to him, laying there unable to know what he was doing until she felt it.  She let her tongue run over the head, feeling it jerk, her lips tightening on it, holding it firm.  Her tongue continued to explore the hot flesh, running over the head, feeling it leak out when she ran across the slit, tasting his juices.  The taste seemed to grow on her, the thought of it filling her mouth exciting her.  Would she be able to swallow it all?

"Oh yes Cindy.  You have a God given talent for sucking cock.  You just needed lessons on how to perform.  OHHH GGGGODDDD," he screamed, sliding his cock forward into her mouth, fighting the urge to cum.

She felt it, the jerking of his cock, his body pushing his thick cock through her tightly clenched lips and then his body grew rigid.  She felt the jet of cum shoot from his cock into her waiting mouth, her tongue suddenly bathed with the thick, salty fluid.  She froze, not sure of what to do, afraid she had made him cum too soon.

His hands gripped her head hard, holding her still as he fought the urge to cum, unloading a short ropey burst of cum into her mouth before he could control himself, pleased that she stopped moving her tongue.  "Sorry Cindy, but your mouth is just too good.  Don't worry just a little shot.  My cock is still hard.  There is so much more for you.  You still have to take my cock in your throat.  Now hold the cum in your mouth, don't swallow it until I tell you.  Tongue my cock again."

She felt the thick cum sitting on her tongue.  It slowly spread, filling her mouth, the salty taste permeating her taste buds.  It was no longer unpleasant, just different.  She held it inside her mouth, using her tongue to coat his cock with his cum, taking the thick cr?me and lathering his head with it.

He began to slide his hips back and forth in a gentle fucking motion, holding her head firmly as he used her mouth. He had to fight the urge to cum.  "Let me see your tits Cindy.  Slip the comforter down to your waist."

He wanted to see her naked body, or at least half of it.  But she knew that it was only the beginning, he had already told her that he wanted to watch her masturbate until she came.  At least she was blindfolded; she wouldn't have to see his eyes raping her naked body.  Her hands trembled as she gripped the top of the comforter, his cock beginning to slide in and out of her mouth, aided by the cum that coated the thick member.  She felt her nipples harden suddenly when the comforter slid over the tips, the cool air seemed to rush over them, signaling to her that she was half-naked.

"What a lovely set of tits Cindy.  Big, pink nipples, nice dark areolas, nice firm flesh.  Arch your back and stick out your tits for me Cindy."  He teased her.

She thought the darkness would prevent the embarrassment, but he enjoyed describing her naked body, making her pose for him as she arched her back, a mental image in her mind of how she must look posing her naked body for him.  "GGGODDD," she cried out when she felt a wet finger touch her nipple, feeling the tip almost burst in pleasure.  She felt the finger return, this time slapping one hard tip back and forth until she felt a strange stinging in the end of her nipple.  It felt as if it would explode.  His hips continued to rock back and forth, shoving his cock in and out of her mouth.

"Play with your tits for me Cindy.  Show me how hard you can make them.  And keep your tongue running over my cock.  I'm going to fuck your face now."  He watched as her hands moved to her breasts, cupping the twin globes, her fingers plucking at her hard nipples.  He heard her moan, not sure if it was because of her fingers or his cock as he began to take deep thrusts into her willing mouth.  "Yes, suck hard Cindy," he moaned in pleasure as his cock banged against the back of her throat, his hips driving his cock with pounding thrusts, her sweet lips wrapped so tightly around his cock.  He gripped her head tighter, enjoying her lips as they pressed tightly around his cock as if it were her pussy encasing his cock.

His cock drove in and out of her mouth, his balls slapping hard against her chin as he fucked her face, her hands plucking at her nipples, deriving so much pleasure as she pinched them hard.  She felt so degraded, yet so excited as he used her mouth as if it were her vagina, fucking her with deep strokes that each time threatened to race down her throat at the same time, forcing her to play with her body as she imagined him watching her.  It seemed that she was deriving as much pleasure from the oral copulation as he was.  She decided to get brave, her hands sliding down from her breasts, over the flat plane of her stomach to push the comforter off of her abdomen.  His cock slowed down, Cindy imagining him gazing down at her.

"Yes, I like that.  Show me how you can play with your pussy.  Masturbate for me."  Bill began to slow his thrusts in her mouth, his cock feeling like he would cum soon.  He wanted to wait as long as possible; he wanted to get her aroused so she would cum when he did. "All the way down, kick the comforter off of you.  Then spread those lovely legs for me.  Show me that sweet pussy."

She sucked hard on the cock in her mouth, dragging it deep into the hot confines, her tongue running back and forth over the shaft, feeling the bumps and ridges, wanting to please him.  She felt the cool air on her naked body, slowly spreading her legs, feeling her wet pussy lips separate, the cool air of the morning blowing on her wet sex.  She could only imagine how she must look, Bill poised over her naked body, the bright morning light shining on her naked body as she sucked his cock.  She let her hands move down to her spread legs, pulling her pussy lips back even farther, realizing how brazenly she was revealing her inner sex, her inner pink pussy dripping wet with desire.

"What a lovely pussy Cindy.  So nice and pink.  Pull your lips apart more, until they hurt a bit.  You'd been surprised that a bit of pain feels good."  He watched as her fingertips gripped her lips, digging into the slick lips, pulling them, stretching them wide, a moan on his cock that she was pulling them hard.  "Yes, now bring your legs up, then bow your knees out.  Show me all of your treasures."  He gave his hips a powerful thrust, driving his cock forcefully to the back of her throat.  But he didn’t stop until her heard her choke, his cockhead banging against her tonsils.

"GGGHH," she gagged as his cock pushed farther then it had ever, slamming into her mouth until she almost swallowed it, the thick head making her choke, his cock taking advantage of the situation and push deeper, deeper into her opened throat.  She felt his hands tighten on her head, knowing that he was getting to the point where he would drive his cock into her throat.  She didn't know where she would be able to stand it, but she wasn't sure she had much choice.  She began to rub her clit, hoping the increased arousal would somehow make the inevitable throat fucking more pleasurable.

"Yes, play with that big clit.  Look how aroused you are.  Stick two fingers in your pussy.  Fingerfuck yourself.  Imagine my cock driving between your legs."  Her mouth seemed to take a renewed interest, her lips so tight that it was getting difficult to drive it back and forth.  And her tongue seemed to be everywhere, lathering up his cock from the tip down the shaft, the raspy surface of her tongue bringing such pleasures to his cock.  He couldn't help himself any longer, his cock continually leaking into her hot mouth, his balls tingling as they banged against her chin with each thrust.

She was going crazy with lust, finger fucking herself brazenly as he fucked her face, his hands pinning her head to the pillow, driving his hips back and forth.  She had never been taken so ruthlessly before, her mouth serving to please him, her hands having to derive her own pleasure.  She took a deep breath as he drove into her mouth, gagging as he breached her throat.  She knew it was time as he held his cock in the breach, his hands gripping her head until Cindy felt like it was in a vice.  "GGGHH," she gagged again, her throat opening as she choked her stomach turning as she fought the urge to vomit.   He yanked off the blindfold, tears streaming from her eyes, but she knew that there would be no turning back.  He was determined to force her to take his cock in her throat and she was unwilling to stop him.  She jammed three fingers in her pussy, two fingers twisting her clit harshly, hoping the pain in her loins would take away the fear she felt.

It was time, his cock poised in her throat, her body clenched and tight.  He shoved, feeling her choke, the muscles of her throat opening up and then clenching down on his rigid cockhead as he began the gradual ascent into her throat.  It felt like a warm gloved hand gripping his cock.  "God, your throat is eating my cock alive."  He pushed deeper, another gag coming from her muffled mouth, tears running down from her wide open eyes, searching for some relief.  "Take it deep Cindy.  Take my cock in your throat."  He gave her a couple of staccotto jerks of his cock, harshly pushing in and out of her throat, her muscles beginning to spasm on his hard flesh.  He placed a hand under her chin, pulling her head up so he could see the look on her face as he throat fucked her.  The mask no longer hid her from what was happening, her eyes only inches from his stomach, feeling his balls on her chin, as she was slowly pulled onto the hard cock, the thick member sliding deeper and deeper into her clenching throat.

"Such a good cocksucker.  Can you cum for me Cindy? Play with that sweet pussy and cum for me.  If you do, I'll pull my cock from your throat.  Then I'm going to empty my balls in your mouth, filling you with my cum."

He was using her throat as if it were her pussy, pulling her on and off of his raging cock.  She felt her throat rubbed raw, the choking making her stomach turn.  She rubbed her pussy faster, running three fingers in and out, spreading her fingers when they were inside her, feeling her insides stretching.  Her other hand pinched her clit, her ass raising up from the bed, the pain and pleasure mixing together, Cindy not even able to comprehend what was happening.  All she knew was she had the urgent need to cum.  Even worse, she looked forward to when Bill would cum in her mouth, wanting to experience the complete surrender of her body to him.  It came on her quickly, her pussy clenching uncontrollably on her fingers, yanking hard on her clit, stretching it out.  It hit her like a freight train, her body shuddering and shaking as she came, her fingers drenched in her own juices.  She took a deep breath, long enough to fill her lungs before Bill blasted a thick load of cum into her mouth. It wasn't anything like the last one.  This one seemed to make her cheeks bulge out with the thick cr?me as he unloaded gallons of cum into her willing mouth.  It seemed like gallons, cum dripping from the corner of her mouth as she attempted to swallow the thick cum.  She coughed, choking on the thick cr?me as she tried to swallow the abundant cr?me bulging out her cheeks.  As soon as she swallowed, a second load spilled from his cock into her waiting mouth, his hips pumping in and out of her tightly clenched lips, her tongue lapping at the head like a cat.

Bill couldn't wait any longer.  He saw her cumming, her fingers moving so fast as she fingerfucked herself into an orgasmic frenzy, her hips moving up and down as her fingers raced over her pussy.  He pulled his cock from her throat, her eyes open in relief at being able to breathe.  He let her tongue run over the head as he felt the tingling race up from his balls to shoot a load of cum into her waiting mouth.  Her eyes opened wide in surprise as she scrambled to contain the copious fluid that bulged her cheeks out.  He let his hand rest on her neck, feeling her beginning to swallow, another load of cum shooting out before she could finish, her choking exciting him.  One more load filled her mouth as he watched her hand slow down her masturbation, her fingers glistening from her juices, her throat swallowing, a river of cum dripping from the corner of her mouth.

She almost hated for his cock to leave, tightening her lips on the shrinking cock as he pulled it out, her body exhausted from the orgasm that raced through her body.  She had never been so completely taken by one individual, her body used solely for the purpose of pleasuring him, her mouth taken as a substitute for her pussy, forced to orally satisfy him until he discharged his semen deep into her stomach.  He pushed her hair from her face as he got up.

"Go back to sleep.  I have to go to work.  There is no hurry for you to leave.  I hope to see you again soon.  I enjoyed taking you so completely."  He looked down at her naked body.  "And a beautiful creature you are."  He got up and left, but not before he left some money on the table.

"I've never been so sexually overcome by one person before.  You saw that I enjoyed it," looking down at her naked body, not even ashamed of him seeing her that way.

She sat up on the bed when she heard the door close.  She leaned over the table and counted the money he left.  She smiled, pleased.  It was exactly the same amount that he always paid her.  She was glad.

Coming soon:  Handcuffs Found, Key Lost

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Engaging The Babysitter

I walked towards the door and saw her through the small window. 'Oh, there she is the barely legal dazzling brunette I have babysitting my son. What I wouldn't do to give a ride, and I don't mean in my car. Shit, she is wearing a dress like that to a babysitting gig? Is she trying to turn me on now?'I opened the door and saw her through the glass storm door. She just smiled and waved for a few seconds, and I had to return the favor.I opened the storm door too. "Hello, Alli, you are looking...

Taboo
2 years ago
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BlondieDennis The Menace The New Babysitter

Blondie/Dennis The Menace: The New Babysitter (Or When Dennis Meets Blondie)by Sniper32One Friday night Dennis was introduced to his new babysitter, a nice younglady named Blondie Bumsted. She was a 35 years old friend of his mother, shewas a stunning 5'9, slimmed hipped, long legs, a nice ass and a perfect setof 38c breasts.Denise's parents Henry and Alice were going out for dinner and dancing fortheir anniversary and would be gone most of the night.Now as everybody knows Dennis is a handful...

2 years ago
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Michelles New Babysitter

       I love my wife.  One of her best qualities is how she let’s me treat her thirteen year old daughter, Michelle.  My first treat was when she informed me that I should be the one spanking her, and that she would be stripped first.  I went along and spanked her thinking it was just the way they did things in their family; the fact that I was enjoying myself I kept to myself.  Than one day I came home to see that my wife had invited all of her friends over and had Michelle in diapers on the...

3 years ago
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B Is for Babysitter

It's never easy for a child when his parents split up. Circumstances affect circumstances and usually for the worse. In Billy Bonds' case, his parents' impending divorce was all the harder because he knew deep down that, despite what they always say, he was the cause of it all. He wasn't, of course. But what's a 14 year-old boy on the edge of puberty and teenage defiance, painfully self-aware and utterly confused about everything supposed to know about life? You could say Billy was a...

2 years ago
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Naughty Babysitter

Instead of taking their daughter to a daycare, they have a babysitter come in to watch her during the day. They had just recently hired a new babysitter, Jennifer, an 18 year old freshman at the local university. Jennifer only took afternoon and evening classes, so she was able to babysit until Tina or Paul got home. Jennifer stands average height, with an average build. She did play sports in high school, along with being a cheerleader. She was excited about finding the babysitting job so...

3 years ago
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Abigail the Babysitter

This is my first try… Leave comments to what you think could be improved! * * * It was six oclock on Friday night when Abigail began to make her way down the street towards the OLachlan house. She grumbled under her breath. There were plenty of things that she would rather be doing on a Friday night that didnt involve babysitting two teenage brats. Her mother had pressured her into babysitting the OLachlans kids, though Abigail didnt see why they needed babysitting. The oldest, Jacob, was...

4 years ago
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Naughty Babysitter

Paul and Tina have been married for about 6 years, and have a 3 year old.Instead of taking their daughter to a daycare, they have a babysitter come in to watch her during the day. They had just recently hired a new babysitter, Jennifer, an 18 year old freshman at the local university. Jennifer only took afternoon and evening classes, so she was able to babysit until Tina or Paul got home.Jennifer stands average height, with an average build. She did play sports in high school, along with being...

4 years ago
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Taken By The Babysitter

Chapter 1Chelsea, our regular babysitter for the last five years had recently left for college but recommended her younger sister, Angela, for the job. Chelsea told us that Angela had graduated high school a year early with honors but was taking a year off before she went to college on a full academic scholarship and would welcome the income, and she also loved kids.So, about a week ago, my wife Janice arranged for Angela to watch our five-year-old son for a couple of hours so that we could go...

Teen
4 years ago
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My new babysitter

When I was a little boy, mom had just been mom, but recently I had begun to notice that she was also a gorgeous female and I checked out her amazing body whenever I figured I could do so unnoticed. Since my parents really weren’t really very prude, I had even managed to get a couple of glimpses of my mom in partial or full state of undress, in the bathroom for instance. Being a horny young teenage boy, I of course jacked off all the time and the images that were burned in my mind of my nude mom...

1 year ago
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Cosplayer babysitter

You're sitting in class paying close attention to the clock as it ticks down to the final bell. You were just seconds away from becoming free from High school. Everyone else in the classroom now seemed to be doing the same thing you were doing as you start to hear the class shout 10! 9! 8! 7! 6! 5! 4! 3! 2! 1! RIIINNNGGG! The entire class of seniors stands up and cheers as their 4 long years of High School were finally over. You get and smile as you walk out of class with your friend Joe. You...

3 years ago
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The Hot Babysitter

(It is implied that all characters in the story are atleast 18, and at no point am I implying that any characters are under 18) https://youtu.be/zNtBUerpNcE ======================================= It was hot Saturday night in the fall, and your parents wanted to go out on a nice date. They wanted to get dinner and then go watch a show in the city, which meant you had a good 4-5 hours at home alone. You got really excited when you heard that. You just thought of all the porn you could watch in 4...

Teen
3 years ago
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An Unexpected Threesome With The Babysitter

My husband and I were celebrating our wedding anniversary and we asked our babysitter to come over. Sandy is a young woman who’s nineteen, very reliable and always available to make some money. She’s so good with our children and we’ve had her babysit our children for the last few years. Our children just love her to death. Rex and I were celebrating our twentieth wedding anniversary. We always go to the same restaurant when we're celebrating special events. We both love Italian food and...

Group Sex
1 year ago
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The Babysitter

Falling victim to the fashion trend of the tight black leggins, left almost nothing to the imagination, as her legs, small hips, and the tiny gap between her thighs, were open-season for anyone who dared to view them for more than two seconds. She was not the first babysitter Mister I would have chosen to watch his k**s, since Teagan was just a k** herself, yet he also didn't dare to tell his wife that he found her to be somewhat of a distraction as well."The k**s love her," she always said,...

2 years ago
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The Babysitter

My wife, Amy, had left to go see her sister for a few days, apparently her and her husband were having some marriage troubles and she wanted to be there to support her. That left me at home to watch our two little girls Sarah, who was three and Paula, who was five. They were good girls and helped Daddy as much as three and five-year old girls can. My wife was supposed to be gone for a week but maybe longer, it would depend on what happened with her sister.  I didn't mind her going, I try to be...

Taboo
3 years ago
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Dusky Babysitter

I woke up in the middle of the night amidst all the shouting , I rolled over and looked at the time , I was 3am in the morning , I cursed my neighbors , they were always fighting , I put the pillow over my head and slept . next morning I got up and went for a run as usual , it was a beautiful morning , I stay on the fourth floor of a huge apartment building , its a sort of colony , my flat is the last one in the corner so I have to pass all the other flats , my neighbors front door was open a...

4 years ago
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Dusky Babysitter

I woke up in the middle of the night amidst all the shouting , I rolled over and looked at the time , I was 3am in the morning , I cursed my neighbors , they were always fighting , I put the pillow over my head and slept . next morning I got up and went for a run as usual , it was a beautiful morning , I stay on the fourth floor of a huge apartment building , its a sort of colony , my flat is the last one in the corner so I have to pass all the other flats , my neighbors front door was open a...

1 year ago
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My favorite Babysitter

The babysitter used to cover what we called our split, the time my wife would go to work until the time I got home from work. It usually was no more than a couple of hours. I never really got a chance to spend time with the babysitter because as soon as I showed up she needed to head out the door to go to her college class. She was 18 years old and the neighbor’s daughter; it was a really convenient situation for all of us. She was definitely a site to see, about 5’6 with a slender build and...

First Time
3 years ago
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Babysitter

This was so embarrassing… He would be here in nearly an hour. I am 18 after all, why on earth did my parents have to call a babysitter on me for the night. I am no baby! Just because last summer when they were away I had a party and had the cops called on me, was no reason to put me through having a babysitter for just one night. They were going to be gone only ONE NIGHT! This was ridiculous. I was in my room, pouting of course. What could I do to make my parents feel stupid for this? There had...

3 years ago
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Ditz the Babysitter

In a sudden delusion caused by two simultaneous synapses crossing each other, I thought, "Gee, wouldn't it be keen to tell the story of how I, Harvey Marcus, got started with all of this screwing around. I mean, it didn't just happen out of nothing. Everything has a cause, a spark, an ignition. So, here's my first Official Retrospective. Appropriately, it is my Origin Episode, how I involuntarily got sucked into a campaign of accidental sex with all of the world's eighteen-year and older...

2 years ago
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Spanked By The Babysitter

I had just turned sixteen but my parents still insisted I have a babysitter. I wasn't the most mature sixteen year old so I guess you could understand it. My babysitter was a nineteen year old girl called Rosie. She was in the sixth form at my school and was a was an incredibly sexy girl who always wore sexy clothes and was very popular with boys and girls alike. She was tall and slim with long blond hair. All my friends fancied her so I was kind of happy she was my babysitter I guess. One...

Spanking
3 years ago
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Loving My Slutty Babysitter

It was like nothing I’ve ever felt, but it still didn’t compare to what came after, when I pinned her supple and innocent body beneath me. “Oh, my-” “Don’t talk,” I told her. “You don’t need to tell me how much you want this.” Goosebumps shot across her skin and a cry of sheer pleasure escaped her lips, the very moment my head brushed her soaking wet entrance. “Your body will take care of that, all on its own.” I couldn’t have possibly imagined that that was how my day would end, but as I...

2 years ago
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Whos Watching the Babysitter

As it turned out, she wasn’t even mine. My ex-wife had screwed a guy, got pregnant, had the baby and never let on that she wasn’t even my child. I’d still be in the dark if my Maggie hadn’t come down with this rare blood problem and they wanted a blood transfusion from me. But after checking my blood type they said that I wasn’t her daddy so they had to get the blood somewhere else. She’s fine now, a beautiful little second grader that’s full of herself but needless to say, I was shocked...

4 years ago
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The Angel Babysitter

------ Shifting his position on the couch, Shane re-adjusted his laptop on his legs. Laying his head back on the arm of the couch, Shane sighed happily. In just fifteen minutes, his parents would be out of the house, and away for a week. He’d been planning what to do for months, and was looking forward to it. As soon as they were at the end of the road, he was calling a bunch of mates to come round and stay over. It would be utter bliss to just have a week where he had to do absolutely...

4 years ago
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Spanked By The Babysitter

I had just turned sixteen but my parents still insisted I have a babysitter. I wasn’t the most mature sixteen year old so I guess you could understand it. My babysitter was a nineteen year old girl called Rosie. She was in the sixth form at my school and was a was an incredibly sexy girl who always wore sexy clothes and was very popular with boys and girls alike. She was tall and slim with long blond hair. All my friends fancied her so I was kind of happy she was my babysitter I guess. One...

2 years ago
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The Babysitter

My wife, Amy, had left to go see her sister for a few days, apparently her and her husband were having some marriage troubles and she wanted to be there to support her. That left me at home to watch our two little girls Sarah, who was three and Paula, who was five. They were good girls and helped Daddy as much as three and five-year old girls can. My wife was supposed to be gone for a week but maybe longer, it would depend on what happened with her sister.   I didn’t mind her going, I try to...

4 years ago
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Punishing the Babysitter

I hate working on Saturdays but you can’t have everything in life. It was 2.30 pm and surprisingly I was able to finish my work which was supposed to go until night, so I rushed out of my office to be with my k**s. I didn’t have to worry because of Nina, my babysitter, who has been with me for a while and even does some household work. She didn’t complain about my many demands because I paid her generously. She was 21 years old but looked a bit younger and very devoted to looking after my two...

3 years ago
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The babysitter

A babysitter story with a twist.Let me start by telling you that I am a divorced man in my fifties and I never expected this to happen to me. It was a rare Saturday that I had off my work, the day was warm so I decided I’d wash the car, something I enjoy doing, making it look good again.My neighbour Pete was also out doing the same and we got chatting. He told me it was his wedding anniversary and he and Cathy, his wife, were going out for a posh meal this evening, they’d got their regular...

1 year ago
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The New Babysitter

It was a Friday night which means that the Jacksons would want to go out to eat by themselves, but their longtime babysitter had moved away. Desperately they called their friends daughter Sarah who was 18 years old had the night free so she agreed to come over and watch their eight year old daughter for the night. When she arrived at the Jacksons the two of them were had their coats on and about to leave.“Jenna is asleep and you shouldn’t have any problems with her.” Mrs. Jackson told...

2 years ago
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Taking The Babysitter

"You know dear," I blurted, "if you’re going to ogle my husband like he's a piece of meat, you may as well get a closer look." Debbie, our babysitter for the last two years, blushed scarlet and averted her gaze. Granted, Michael was looking just fantastic tonight, flashing his white teeth and dark eyes in a grin that lit his face with burning sexual desire. That probably had something to do with me saying what I’d said. That, on top of the fact that we'd been teasing each other about her crush...

Taboo
3 years ago
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caught babysitter

As a middle aged salesman and father of two, I rarely have time for dating. I usually get by on random hookups, but recently I experienced a drought. After a couple of rough months, I was dying for release. I arranged for the babysitter to watch my daughters and headed to the bars in a last ditch effort to get laid. Unfortunately, I suffered a night of strikeouts and returned in defeat. As soon as I got in the door, I headed straight for my living room. My plan was to promptly pay the...

4 years ago
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Wife Dominated by the Babysitter

Fiction...blah blah blah… Usual disclaimers, you know the stuff by now…Well, me and my wife Kim were on the way home from a night out with friends, the usual shit, restaurant, couple of drinks, me driving. As ever, she’s bending my ear about some nonsense that must only be important to women because I’m really not getting any of it, I’ve got bigger things on my mind…You see, I’ve been shagging the babysitter for months now. She’s called Danielle, she’s 18, only short but with a frame to die...

2 years ago
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Rachel My Amazing Babysitter

This is a true story. “But MOM!” I pleaded. “I don’t NEED a babysitter! Can’t I just stay by myself this once?” But she wasn’t budging. For Pete’s sake, I was f******n. Just because my parents had to go out of town for the weekend, why did I have to have somebody staying with me like I was some little k**! “Look Jeff, I’ve heard all I’m going to hear from you. I’m getting Mrs. Walker’s daughter, Rachel to stay with you, and that’s all there is to it.” Then her voice softened somewhat. “Listen...

4 years ago
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Phone Sex and The Babysitter

I’d planned to work late but various meetings were cancelled so I caught an earlier train. On the walk from the station, as usual, I called in to The Bull and Bush pub for a quick drink, then made my way home – only a 5 minute walk.There was a strange car in the drive so I walked round the side of the house. It was dark so I knew I wouldn’t be seen. When I looked in through the patio windows, there was Laura, our 18-year old babysitter, on her knees giving a boy a blowjob. She seemed quite...

Straight Sex
1 year ago
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The New Babysitter

It was a Friday night which means that the Jacksons would want to go out to eat by themselves, but their longtime babysitter had moved away. Desperately they called their friends daughter Sarah who was 18 years old had the night free so she agreed to come over and watch their eight year old daughter for the night. When she arrived at the Jacksons the two of them were had their coats on and about to leave. “Jenna is asleep and you shouldn’t have any problems with her.” Mrs. Jackson told Sarah....

Erotic
2 years ago
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Horny Babysitter

Talk about the worst date night ever. Marie, my wife, started drinking from the get-go way too early, and by dessert, she was smashed. I mean, I get it. We have triplets and they are a handful, but this was supposed to be our anniversary and she drank it away. I was slightly drunk but nowhere near her level, nor could I get there as now I was paying a babysitter to watch triplets while I babysat my wife. She stumbled out of the taxi door and almost face-planted into the snow. I sighed and...

4 years ago
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My favorite Babysitter

The babysitter used to cover what we called our split, the time my wife would go to work until the time I got home from work. It usually was no more than a couple of hours. I never really got a chance to spend time with the babysitter because as soon as I showed up she needed to head out the door to go to her college class. She was 18 years old and the neighbor’s daughter, it was a really convenient situation for all of us. She was definitely a site to see, about 5’6 with a slender build and...

4 years ago
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Isabella Part 0 Babysitter

The source of the awkwardness was none other than Mrs. Blancher herself, who had allowed herself to become more drunk than she intended. She was an active drunk, the type that hit on anything male. As it so happened, their host's fifteen year old son had noticed and tried to get her to rest in a room upstairs. That proved to be a big mistake. No sooner had he gotten her onto the bed then she had started stripping both herself and him. Luckily it was Adam who noticed his wife's absence from...

4 years ago
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Bailey Our Babysitter

Bailey was our very vivacious seventeen-year-old babysitter and from the moment I first laid eyes on her, I knew I wanted to experience a little private one-on-one time with her. Bailey was an elusive catch, but one that was worth pursuing.Our relationship was very casual at first and very businesslike, but the more she took on babysitting duties for Ally and me, the more desirous I became. I loved Ally, but our marriage had become a little rocky. I was pretty sure Ally was seeing someone on...

Cheating
2 years ago
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Drunken Babysitter

Drunken Babysitter My wife knew that I was going to be working late so she got Stacey the girl down the street to baby sit our four-year-old. Stacey was sixteen and supposedly mature enough to do the job. When I pulled into the driveway and got out of my car I heard my back door slam and I saw a boy go running across my backyard. I went into the house just a little hot under the collar. I looked around and found Stacey hiding behind a chair down in the family room. She was naked...

1 year ago
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I Fucked The Babysitter

and a movie. It was pretty late, and the babysitter was asleep on the couch. The kids were sleeping in their rooms, perfectly safe. I wasn’t sure if I wanted to wake the babysitter or not. I told my wife to go on to bed and I would stay up a little longer to see if she wakes up and then take her home. I turned on the tv, keeping the volume low. Every once in a while, she would shift her position on the couch and I looked over at her to see if she was waking up. What I saw...

3 years ago
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The chubby babysitter

Since the first night george stayed at sarahs he decided to crash there for a little while since it was winter break and right across the street from 7-11. He would still hang out with his buddies during the day but at night he was usaully getting fucked by sarah, his little brothers old babysitter. They would usually ask questions afterwards about eachother, and then go to sleep. During the day on time zack came over to sarahs apartment to play xbox with george while sarah was working her day...

2 years ago
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The curvy babysitter

38 year old Sarah and 17 year old george re met at a pool and hooked up in part 1, in part 2 george decides sarah needs more then just himself. Since the first night george stayed at sarahs he decided to crash there for a little while since it was winter break and right across the street from 7-11. He would still hang out with his buddies during the day but at night he was usaully getting fucked by sarah, his little brothers old babysitter. They would usually ask questions afterwards about...

2 years ago
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Sexy New Babysitter

Looking at the text from my wife I felt a combination of emotions. I smiled reading that she was excited for our date night, my cock throbbed in my slacks as I thought about what that meant, and I felt shame that instead of thinking about my wife, my thoughts were full our latest babysitter. Kat was twenty years old, a sophomore in college, and sexy as hell. A few months previous we had posted an ad for a new babysitter after my sister-in-law moved to California to go to USC. Kat had called...

2 years ago
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Adam and the babysitter

Introduction: Little Adam gets to fuck the babysitter. This is my first story ive wrote, leave your pheedbacks and tell me what you think. All pheedbacks, corrections, ciritisizm and suggestions will be appreciated. This is not a true story, its just a fantasy of mine. Enjoy! ———————————– I put up a babysitting ad on craigslist. Its not that i needed the money but i guess id like the extra cash. My name is kristen, im 16, 52 brunette, brown eyes, i have pretty firm round ass and i wear a C...

3 years ago
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Adam and the babysitter

Introduction: Adam gets to fuck the babysitter. Note: Ive posted this story on another account but it got deleted so im posting it a second time. Im the original author of it. This is my first story ive wrote, leave your pheedbacks and tell me what you think. All pheedbacks, corrections, ciritisizm and suggestions will be appreciated. This is not a true story, its just a fantasy of mine. Enjoy! ———————————– I put up a babysitting ad on craigslist. Its not that i needed the money but i guess...

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