Jessica's Live-In Babysitter - Part 1 free porn video

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Jessica's Live-In Babysitter - Part 1 by CutePatti ________________________________________ Sam had doubts about Becky's idea when she had broached it to him over lunch at the office. Sam and Becky had known each other for many years and had even had a serious relationship at one time. But that was long over and they were able to remain friends since they worked for the same company. "I have a problem," she said, "and I think you're the perfect solution!" She went on to explain that she had accepted the position of manager of the customer service department. She had agreed to take on managing the night shift, from 5 PM to 1 AM because it paid almost twice the daytime shift. Money was tight these days, she said. Her problem was that she didn't feel right about leaving her daughter alone so much of the time, especially at night. In addition to that, it made it difficult for her to have a social life. She had a steady boyfriend now, and whenever they wanted to spend some time together, it necessarily involved getting someone lined up to look after her. "So," she said after explaining this all to him, "I got to thinking that things would be a lot better if I had a roommate, someone I could trust who would keep an eye on Jessica when I wasn't there, someone whose work hours weren't as crazy as mine, a sort of live-in babysitter, someone like you, Sam." He had resisted at first, but she was very persistent. She pointed out that the lease at his apartment was about to expire, and she would charge him practically nothing for the room, exactly nothing, in fact. And Jessica knew him, she would feel comfortable with him. "And," she added, "we both know you're a real home-body, Sam. You always preferred staying home rather than going out." That was true, he had to admit, and it still was. In fact, it was one of the reasons they had drifted apart, since Becky liked going out and having fun. In the end he agreed. He would move in and share Becky's condo with her and her fourteen-year-old daughter Jessica. He would not be her babysitter exactly, but a sort of surrogate step-father. The impact on the rest of his life would be minimal. He was free to go into work during the day, or work from the condo via his computer. He only needed to be at the office a couple of days a week, to have meetings with the group of technicians he supervised, so he would in fact be home most of the time. In short, his only responsibility would be to watch Jessica, to keep her company, and keep her safe. Contrary to Becky's original offer, he insisted that he pay her for the room, half her mortgage payment, in fact. She protested, and insisted that half would be too much. They finally settled on a one-third contribution from him. A great deal for both of them. They discussed the details and ground-rules. He would prepare dinner for Jessica. "That's another reason I chose you," Becky said, "You're such a great cook!" And he would make sure she did her chores and got to bed at a decent hour and help her with her homework. If either of them, Becky or Sam, had dates, they would not bring their partners home. Truth was, Sam hadn't dated anybody for a long time anyway. "Good!" Becky said finally, obviously happy with their arrangement. "I'm going to make sure your room is ready so you can move in right away. So make yourself at home, roomie!" She gave him a brief hug, and went out of the room. Sam sipped his coffee for a few minutes, then looked up as the kitchen door suddenly opened. The door led to a deck at the rear of the condo, and there, framed in the doorway, was Jessica. It had been four years since he had seen her. She was ten when he and her mother had last dated, and he remembered her as a sweet and pretty little girl, with long tresses of wavy blond hair. The three of them had been a close little family during the months he and Becky were together. He wondered if she would remember him now. But, the Jessica standing before him now he hardly recognized since she was taller and much more grown up. In fact, she was as tall as him. He had always been slight of build and was amazed that this girl was now basically the same size as him. Her hair was the same mass of blond radiance, but it was pulled straight back from her forehead and gathered into a big ponytail. She was wearing a short, loose sundress, white with a pattern of yellow flowers, and was carrying a beach bag in which a towel and a swim suit were visible. Flip-flop sandals were on her feet. But that wasn't what first caught his attention. He noticed her toenails were painted a sparkly pink color and had tiny little white flowers painted on them. Unbeknownst to her...or anyone, for that matter, Sam was a man with a foot fetish, so this was quite a lovely sight for him. He momentarily forgot whose feet he was gazing at. The morning sun was behind Jessica as she stood in the doorway, and the light streaming through the thin dress made it virtually transparent from where Sam sat at the table. He was able to see the outline of her slim figure, descending down her sides to her waist and curving out over her hips, then down to the sweep of her long legs. The bright sun provided enough illumination to partially reveal a cute bra which showed only a slight protrusion of yet-to-be developed breasts. Also revealed were the panties she wore under the dress, a brief bikini style. Sam stared, momentarily speechless. He was also fascinated with panties...and bras....and even pretty dresses. Yes, he had a lot of 'special' interests which he kept hidden. After a few seconds Jessica broke the silence. "Uh, HELLO......earth to Sam!" she said. "So, you're gonna be my babysitter, huh? Well, do you recognize me? So are you going to look at my face or just keep gawking at my feet?" She rolled her eyes. Sam blinked and found his voice. He quickly averted his gaze from her feet, smiled and got up to greet her. "Yes, I remember you, Jessica," he said. "But think of me as a roommate, not a babysitter. Besides, we're old friends." Jessica looked at him dubiously. Then she brightened a bit and said, "OK, roomie. But please call me Jessie since that's what all my friends call me now. Only Mom still calls me Jessica." Jessie walked to the table and plopped herself into a chair, dropping her bag on the floor. "I was headed over to my friend Amy's house and we're going swimming in her pool, but I thought I'd come in and say 'Hi' first. So, Hi." She splayed her legs out in front of her, looking intently at Sam. She started working her flip-flops with her toes as she watched Sam looking at her. It was like she was purposely displaying her cute toes to him. He wondered if she somehow guessed the effect that had on him....after all, she had noticed him staring at her feet a few minutes earlier. "I'm glad you did," said Sam, trying to act normally. "I've been looking forward to meeting you again." "Yeah, me too, I guess," she said. "But it's kinda weird Mom asking you and all. I mean, you guys were going out, right? Back when you knew us before?" "Yes, we were," Sam said. "But things just didn't work out. That doesn't mean we can't be friends, though, right?" She twisted her mouth to the side and frowned skeptically. "I guess. If you say so. But I still think it's strange." "Unusual, maybe," said Sam, "but not strange. I don't think so anyway." Jessie was silent for a few moments. "Do you have a girlfriend?" she asked suddenly. "Not at the moment," said Sam, raising his eyebrows. "Why?" "No reason," she said, "just curious. Mom does, you know. I mean she has a boyfriend." "Yes, I know," he replied, "she told me." "And it doesn't bother you?" Jessie asked. "I mean, if you thought maybe you were going to get back together and all..." Sam smiled. "No, it doesn't bother me. I told you, we're just friends now, good friends. Anyway, you're the reason I'm here, not her. You know what I mean?" Jessie shrugged. "I guess so, but it seems strange you don't have a girlfriend. You do still like GIRLS don't you?" and she grinned devilishly as she said it, emphasizing the word 'girls'. Sam just smiled at her and thought about the implication of what she just said. Yeah, he certainly did like girls. Especially the cute clothes they wear. Then before he could answer she twitched her right foot and her flip-flop fell to the floor right in front of him. "Wow, I am so clumsy sometimes. Could you please pick that up for me?" As he bent down, his face almost touched her outstretched foot and he again wondered if she was purposely teasing him. No, she's too young to understand about those kind of things, he thought to himself. As he handed it to her she slowly raised up her foot and sort of wiggled her toes as she put it back on. "Do you like the way my toes look? I just had them done a couple of days ago. Aren't they awesome?" She was definitely teasing him, or maybe even testing him to see his reaction. Sam was trying not to watch too intently but was mesmerized by what he was seeing. He said, "they look very nice and, yes, I like the way they look." She smiled a sort of 'got-cha' smile and then stood up. "Well, I gotta get over to Amy's," she said, scooping up her bag and heading for the door. "Guess I'll see you later." She opened the door to go out, then stopped and turned back to him. "It's nice to see you again, Sam" she said. "I guess I'm glad you're here." Then she bounced out the door. "See ya!" she said brightly, and was gone. Sam stood for a few moments, watching her through the window as she traipsed off to meet her friend. As he watched her he remembered the cute bra and panties she was wearing, and how he had seen them through her sheer dress. Wow, how he loved bras and panties. Especially the cute kind that young girls wore. And now he was going to be living with one. Becky came back into the kitchen a minute later and saw him looking out the window. "I heard you talking with Jessica," she said. "You two get reacquainted? Things go okay?" "Great," he said. "I was worried, I admit, but she seems fine. She has certainly grown up since I last saw her. She's as big as I am." "Good," Becky said, "I was worried too -- but only a little. Yes, she has gotten a lot bigger, but she still seems like a little girl in a lot of ways." "What do you mean," Sam asked. "Well, she is very mature and has grown a lot, but she still likes to dress very femmy. You saw how she was dressed." Yes, Sam thought to himself.....I saw how she was dressed! She took her purse and went to the door. "I've got a few errands to run. Why don't you get settled in, and I'll see you later. Jessica should be back about four or five, then maybe we can all go out to eat and celebrate. Why don't you go upstairs and check-out your room while I'm gone. It's right next to Jessica's. Oh...and you will have to share a bathroom with her. I hope you won't mind." "Sounds good, No, I won't mind at all." he said, "see you later." After Becky left Sam sat down at the table and sipped his cold coffee, deep in thought. Nobody knew about this hidden side of him, nobody. It was one of the main reasons he had tried to talk Becky out of this arrangement. But, perhaps, also the reason he finally agreed. The thrill he had experienced a few minutes ago when he saw through Jessie's dress was something he couldn't control. Seeing her wearing such a girly outfit aroused him, and literally made his knees weak. For as long as he could remember he had been irresistibly attracted to young girls, girls like Jessie. The fact troubled him, but girls around her age excited him terribly, especially on those occasions when a careless gesture or a gust of wind afforded him a view of cute panties under the girl's skirt. Or the sight of a girl wearing cute shoes and socks, or sandals exposing pretty feet and toes. Whenever that happened his heart raced and his penis stirred. Becky saying that Jessie dressed 'femmy' made him tingle hearing just that word.....femmy! And he would be staying in a room right next to hers. Before you get the wrong idea, Sam was NOT a pedophile. No, not in any way. He had no sexual attraction or desires for young girls. Their sweet innocence was what attracted him to them....well that, and their clothes! That explains why he loved seeing Jessie's bra, panties and her cute sandals. Those items are what makes his penis drool. Especially when he can see a girl wearing them and innocently displaying them to him. So why the fixation with feet and toes? He had no real answer for that. Fetishes are hard to explain or even understand. It just was the way it was. So here he was, about to move into a condo where he would be keeping constant company with a fourteen-year-old girl. And a femmy one, who had lots of cute clothes, no less. On the one hand, he wanted to be a responsible adult, protecting the child of a friend who trusted him and he knew he would do that without fail. But, on the other hand, he felt like a kid who had just been put in charge of a candy store. As he headed up the stairs to see his new room he passed by Jessie's. He peeked in and saw how feminine it was and his penis reacted. And, as he surveyed the room, he realized that her dresser drawers and her closet were filled with those articles of clothing that aroused him so much. Yes, this was definately a good decision to live here! End of Part 1

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The Punishment of the Babysitter

Jenny was almost 16 and had never had a boyfriend or even kissed a boy not even held a boys hand. She was the daughter of a single mother who had become very obsessed with her church after getting pregnant very young. Her mother would not divulge the name of her father and Jenny had even snuck a peek at her birth certificate and under father it said None. After getting involved heavily in her church her mother never dated another man and she intended to isolate her daughter in the same manner...

3 years ago
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Bobby Becomes Pussy the Babysitter

Bobby Becomes Pussy, the Babysitter Part I By Tammie Latte "Bobby, how would you like a job working as a babysitter for a week or two?" my mom asked as I entered the kitchen wondering what kind of cereal I was going to have for breakfast. "Aunt Julie has a friend who has to go away unexpectedly on business and needs someone reliable to watch her little boy until she returns. It pays big bucks and Aunt Julie is willing to help out whenever she can. The job is yours if you want...

2 years ago
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Sunbathing Babysitter

Introduction: Our babysitter seeks answers about sex One of the things my wife and I loved about our house, the first time we saw it, was the neighborhood. There were kids playing outside, and everyone seemed to know each other. Since the house was also best of all we had looked at, we bought it immediately. While the house does have its issues, it has a lot going for it, too. First, it sits on a huge lot. Its actually nearly two full lots, meaning we have a huge backyard. It also has a great...

3 years ago
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The Babysitter

Introduction: Cute babysitter seduces a single mother The Babysitter She gave a light tap on the door, knowing that there was a baby in the house probably trying to sleep. The tapping was loud enough to alert the childs mother who was sat in her living room. The house had been silent so the sound startled the young mother who, up to now, had been playing through the infinite possibilities of the night ahead in her mind. The more she thought about it, the more nervous and edgy she made...

2 years ago
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The Babysitter Chapter Two

Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women of the neighbourhood. Some I would wash and return, others I kept as souvenirs. It began to grow beyond just panties, babydolls, bras and basques. I began completely to dress in a feminine fashion...

4 years ago
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The Babysitter and the Nudist Campers Chapters 1 3

Little Dolly Packer hadn’t been a babysitter very long. In fact, she had only started to babysit for money the previous month. Her father was away on a long sea cruise earning much needed cash for the family of five. She and her three other younger sisters were a burden on their sickly mother’s shoulders and Dolly did her best to help out with the earning of income to put food in their mouths and the rent inside her mother’s purse for the dreaded first Friday of every month.Dolly was still a...

Group Sex
1 year ago
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When The Babysitter Came

"Andrea, Susan, can you two come down here for a minute?"I heard mum calling us and felt my cheeks flush angrily. I know Susan was still young but I wasn't a child anymore and didn't want to be treated like one."Andrea, don't start young lady, my taxi's here." The neutral tone couldn't hide her impatience and I could picture her looking at her watch whilst standing at the door, waiting for me to show myself. Knowing she wouldn't leave until I'd done as asked, I resignedly sauntered to the top...

Voyeur
3 years ago
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An Unexpected Threesome With The Babysitter Part Two

A month passed since my wife and I had sex with our babysitter. I couldn’t stop thinking about that amazing night. I know it’s very wrong, but I have to be with the babysitter again. I haven’t told my wife about these thoughts. I don’t want to cheat on my wife, but I cannot forget the feeling of fucking Sandy’s young pussy. I have had dreams about her body and how it felt to be inside of her pussy. I don’t want to share Sandy with my wife ever again. I want to have sex with her all by myself....

Group Sex
4 years ago
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The Babysitter Chapter Two

Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women of the neighbourhood. Some I would wash and return, others I kept as souvenirs.It began to grow beyond just panties, babydolls, bras and basques. I began completely to dress in a feminine fashion...

2 years ago
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Engaging The Babysitter

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 well." "Hi, Mr. Fonpolous, thank you," she replied, strolling into the house. "How are you doing? Has the dating life been decent since the divorce?" "It has been okay, Alli. It is tough out there though, and please, call me, Rex," I corrected her, failing to part my eyes from her while...

3 years ago
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Our Babysitter Watches Us

I met Tracy my senior year at The University of Texas in Austin, what we all considered to be the 'real' U of T. She was a year behind me and was also a business major though she was headed to finance and I was aimed toward marketing and advertising. So, she was a numbers drone and I was a 'flack.' Obviously, we immediately kidded each other unmercifully then proceeded to fall in love. One thing about Tracy that wasn't immediately apparent was that she loved sex, she just couldn't get...

2 years ago
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Propositioning the Babysitter

Jack Niles was married for the last twenty years. He and his wife were best friends. They were each other’s soul mates. They had a healthy sexual relationship and pleased one another. Jack also had secret desires which he didn’t share with his wife. Jack was obsessed with breasts. His wife had a small chest. He begged her to get implants, however she was scared about her health. She would get real mad at her husband for ever suggesting that she needed implants. Jack’s obsession with breasts...

4 years ago
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Blonde Mom Fucks Black Babysitter Pt 1

Introduction: This series will include the babysitter fucking mom with a strapon. Like so many times before Loren Wright had picked up Alex her babysitter. Loren was a 32 year old single mom, but still gorgeous with shoulder length blonde hair, a slim tight body and a perky ass that didnt show a hint of sag. She also had firm breasts that were small still firm and round. Loren was also a lesbian so didnt mind giving her babysitter a ride as the fourteen year old was so hot Loren got a thrill...

2 years ago
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Babysitter Makes Her Move

Ashley chose her outfit carefully. She wore a simple white blouse with buttons. It was tight, but Mr. Brenner couldn't tell since she kept her sweater on till after he left. Her skirt was loose and short--well above the knees. She decided against a plaid, thinking it was cliché and, instead, went for bright blue. She completed the outfit with a pair of pink ankle socks. She was going for a look that was both innocent and sexy--just short of slutty.And she succeeded beautifully.At the same time,...

4 years ago
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my babysitter my teenage whore

My wife and I had been married for five years and had some good sex before our twin daughters were born, then our life in the bedroom began to taper off some.It wasn't that Lisa wasn't attractive any more; she was hotter than ever with the few extra curves she put on after she had the girls.I don't know if she was self-conscious about the ten extra pounds she had on herself or worn out from the girls, but she didn't seem as interested in sex as she used to be.On a good month, I may have gotten...

3 years ago
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Our Babysitter Julia

“So what time does she get here?” I asked, my wife then checked her watch and then looked up at the clock. “In about an hour.” she replied. “Why check your watch and then the clock?” I asked her, “Didn't know that was the time.” she answered. I continued tapping keys at my laptop while she got dressed. She was a beautiful woman, with short curly black hair and a size 8 figure. Her breasts were natural, which some people didn't believe because they were so pert. Sitting like two half...

3 years ago
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Sara The Bad Babysitter

Mr. and Mrs. Crudele were going to have a much needed night out. Since the arrival of their little bundle of joy four months ago they hadn’t had a night out together and in fact they rarely had a few hours sleep in a row. But tonight they had plans for a quick supper followed by an evening at their favorite club. Mr. Crudele had obtained the name of a young woman from a subordinate at his company who said that she was very reliable and came highly recommended. He had called her and she was...

2 years ago
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The Babysitter

The Babysitter She gave a light tap on the door, knowing that there was a baby in the house probably trying to sleep. The tapping was loud enough to alert the child’s mother who was sat in her living room. The house had been silent so the sound startled the young mother who, up to now, had been playing through the infinite possibilities of the night ahead in her mind. The more she thought about it, the more nervous and edgy she made herself. At least her 3 year old son, Callum, had drifted off...

2 years ago
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Babysitter Gets Caught Then Gets Schooled

Introduction: Kayleen is one that likes to be in everyones business- like booze. But after Jimmy and Beth Lawson catches their babysitter in the act, they teach her a painful & valuable lesson. But its the lesson that will forever stick with her for the rest of her life. Beth and I have been married now for twenty years, and still going strong. You could say that were a loving, warm-hearted, deeply passionate couple. We couldnt have asked for anything more, a nice home, three beautiful kids. In...

4 years ago
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The Babysitter

Introduction: A fifteen-year-old gets to babysit two incredibly hot twin boys My name is Mark. Im fifteen, with light brown hair and brown eyes. Im just an average kid, 57, 150 lbs. I think Im into guys, but Im not sure. I mean, I dont want to be gay, but sometimes I catch myself staring at some guys ass, and I think I might be. I know that younger boys turn me on. Theres one family across the street that has two of the hottest boys Ive ever seen. Theyre twins, and they look about ten or...

4 years ago
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Babysitter Gets Dismissed Then The Anniversary BreedingTaboo Begins

Introduction: After Kayleen got schooled and dismissed, Jimmy & Beth teaches the twins how to fuck a REAL woman. FROM THE AUTHOR: This is really the fourth & final installment of Babysitter Gets Caught, Babysitter Gets Schooledseries. After Kayleen leaves, thats when the twins decided to help breed their mom. So their dad teaches the pm a lesson on how to seduce an older woman. Be sure you read the EPILOGE at the end of this story. There might be a spinoff, depending on the reviews. Thanks and...

2 years ago
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Our Babysitter and Her Mother

Our Babysitter and Her Mother By Wonder_Dad - Story #11 - Downgraded AgainThroughout our marriage, the wife was getting restless wanting time alone, either with me or with her girlfriends. I placed an ad in the local newspaper seeking a babysitter. I thought we would be swamped with responses, but after two weeks, there had been only one call. We had decided to interview all candidates in person, before making a choice. We met with the young lady, but she was really way too young, barely a year...

1 year ago
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Babysitter Worth Keeping 12

Babysitter Worth KeepingBy Wonder_Dad - Story #12It was quite a stroke of luck after attempting to find a babysitter that would satisfy our requirements for our two k1ds for so long. The girl, Justine, a young girl of 17, whose jet-black hair complimented lily-white skin, was finally hired. I knew little of her, but was learning quickly thanks to advice of her mother, Tatyana. Justine was truly a carbon copy of her mother in looks, but not in actions. I will not digress and re-tell my previous...

3 years ago
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The Busty Babysitter

Rachel was just pulling her coat on when John came down the stairs. He handed Rachel her payment in cash."Thank you, Mr. Greene." Rachel smiled in gratitude."You're welcome," he replied. "You deserve every penny. Kathy and I are very happy with you. There is no one that we trust the k**s with more than you.""Thank you, that means a lot. I love them like they're my own. I would do anything for you guys." Rachel was starting to blush and was having a hard time meeting John's gaze. For his part,...

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